Sophie and the Boys
"Hmmpfh, hmmpfh!" Sophie's muffled cries echoed inside of the cramped locker where Samantha had left her.
She struggled against the confines of her metallic cell, pushing herself against the locked door in a desperate attempt to break free. She did blame herself for her new precarious position, but Sophie hadn't been able to take it anymore. It was one thing to stomach Samantha's abuse when they were alone together at Samantha's place, or during recess in one of the empty classrooms; but to walk around school dressed like this? It was humiliating Sophie thought, having to pretend like she didn't notice how people were looking at her now. The other girls whispered and snickered behind her back, and the popular boys had taken to whistle and jeer as she walked past. She didn't want to wear these knee-high white socks, the tight white blouse or this ridiculously small red skirt, and she'd told Samantha as much. Not two hours later she'd found herself here, shoved into this tangy locker that smelt like a gym. Giving up on her futile attempts to break free she resigned herself to her fate, adjusting herself trying to get comfortable. Samantha would probably come for her soon enough, she just had to wait until the popular girl's temper had cooled off.
Having calmed down Sophie paid more attention to her surroundings. She could hear the shrill sharp noise of a whistle accompanied by loud voices in the distance. What had been Samantha's plan? Did she expect the jocks to beat her up when they found her? It wasn't implausible. The last adjectives Sophie would use to describe the young men of the school's football team kind and tolerant, and they had little patience for people breaking the norms. A pit formed in her stomach as she realized a feminine and meek boy dressed in a schoolgirl's outfit probably wasn't what they'd consider within the proper dress code.
The thought of being confronted by a pack of adrenaline-pumped footballers renewed Sophie's will to break free. Maybe if she could just get one hand free she'd be able to get the locker open somehow... Sophie gritted her teeth as she tried pulling herself out of her cuffs. Quickly she realized it wasn't going to happen. Samantha had locked the cuffs so tightly in their place that they chafed against Sophie's milky white skin, reddening it and bruising it lightly. Her heart skipped a beat as she heard the creaking of a door being forcefully pushed open, and the grunting and laughter coming from at least a dozen young men, drunk with the adrenaline-fueled high their sport had given them. A sudden fear overcame her, clutching her heart in a cold grasp as she heard how they started to change, eagerly discussing today's training. The resolve that had filled her melted away, being replaced with a hollow feeling in her guts. If they found her now she'd be in real trouble.
"Coach DiMarco is such a fucking asshole, making us run two extra laps around the field just like that." One of the guys grunted, violently wrenching his locker open.
"Fuck you Chad. If we're going to make any progress this season you know you gotta break a sweat once in awhile. You can't expect just pummeling the enemy to the ground every single match because you're a head taller than most. Eventually you'll be confronted with someone to match your size" Another guy said as the faint light streaming down into the locker through the air-holes were being obscured.
Sophie's heartbeat increased, her heart beating so fast in her chest she almost thought the boys would be able to hear it. Not daring to make a sound Sophie tried to stop herself from breathing, drawing only the minimum amount of air in through her nostrils as she bit down on the ballgag. If only she hadn't mouthed off to Samantha she might have gotten to skip the ballgag. Right now she felt like she couldn't breath. She flinched as something slammed against the locker, but after the first moment of panic she realized someone had just thrown their bag against the base of her metallic hideout. Steps came closer, and once more her packed cell grew dark.
"Holy shit guys, you won't believe this." A voice said, tearing down the note that had been taped onto the front of the locker. "Please take good care of my friend Sophie. She's been a bad girl, and needs a firm hand to straighten her out. PS, don't forget to leave me a message about her performance. XoXo / Samantha" He read out aloud, and to Sophie's horror she could see the silhouettes of the entire team gathering around him as they listened.
Light washed over Sophie where she was huddled up as someone pulled the locker open and a cry of disbelief went through the crowd. For just one moment Sophie thought that the guy who reached down wanted to help her, but her hope was turned to panic as she felt his hand roughly grasp her blonde hair. She landed in a pile on the floor, her limbs shaking as she tried to crawl onto her knees. Those cold fingers around her heart squeezed harder as she realized that they were laughing.
"Look at that, Samantha even wrapped this one up nicely for us." One of them said.
"Where are you going?" Another continued, putting his foot against Sophie's side and pushing hard when she managed to get up onto her knees.
"Oh man, look at those eyes. She's scared." A third voice said as Sophie stared up at the crowd, her green eyes quivering as she cowered.
The guy who had pulled her out of the locker grasped her hair again, hoisting her up as his face got close to hers. "Funny. I don't know of any Sophie in our school." He said, his eyes glittering with malice as he glared at her.
She tried to be avert her eyes, but was given pause as something clicked inside of her. Bruce.His name was Bruce. He'd been in Sophie's class in middle school, constantly teasing and poking fun of Sophie for her dainty build, mild manners and her tendency to prefer the company of the girls of the class. He'd hit her several times, and when she told on him like she was supposed to the teacher had been really progressive, suggesting that Bruce just liked her very much. Maybe even loved her. She'd found solace in those words back then, but she couldn't see any love in Bruce's face right now. There was something else however, a burning animalistic want that made Sophie's heart thump even harder as she finally turned her gaze to the floor.
"Maybe you should explain what you're doing in the men's dressing room. Don't you think so princess?" He laughed, and Sophie felt as rough hands fumbled with the straps to her ballgag from behind.
"Argh!" Sophie gasped as it plopped out of her mouth, drawing sharp breaths of air that was laced with the musky scent of a dozen worked up young athletes.
A glob of saliva drizzled out over Bruce's hand as he grasped her cheeks a bit too hard, pressing them together as he forced Sophie to look at him. "Well?" He demanded, squeezing harder. "Why are you here?"
"I don't - I don't know. Samantha she, I didn't want to-" She stammered in reply, her eyes frantically darting around the room. The young men had formed a circle around her, and she swallowed audibly as she heard the door close in the background.
"Well then, you should stay a while sweetheart. The boys and I could use some entertainment after our workout," he began before squeezing her cheeks so hard it hurt. "You don't mind sucking cock anyways, do you you queer fuck?"
"What!? No, you can't!" Sophie wailed as Bruce let go of her and other, even rougher hands twisted her head to the side.
The mushroom-shaped glans of an eager young man's cock pressed hard against her rosy cheek, her irises dilating with fear as she recognized the owner. It was Chad. The goon of the football team. A guy who was more likely to knock an opposing player over rather than trying to outrun them. He wasn't the best athlete, but the coach kept him on for a very specific reason. A brute such as Chad came in handy when you needed to take out the best player of the enemy team. Chad was good at that. Now he was grinning down at Sophie as he dragged his engorged cockhead from her cheek to her wet lips. She writhed, trying to get away from the brutish young man's member, only to be greeted with another one staring right at her.
"Open up princess." Bruce said, his cold hand clutching at her throat. "Be good and maybe I won't tell Gabriel about this.." He snickered, accompanied by a score of laughter from the other guys.
She closed her eyes. She knew first hand that Bruce was violent, Maybe if she just… Her lips quivered as they slowly came apart, glittering with the pinkish lip-gloss Samantha had forced her to wear. The cock felt warm and sweetish against her tongue as it was already leaking precum. She hesitated, feeling the musky scent of excitement mixing with that of sweat in her nostrils. She swallowed hard, closing her eyes before leaning forward. The footballer let slip a groan of pleasure as Sophie took him into her mouth and her wet tongue pressed up against his member. A single tear trickled down her chin as her cheeks hollowed and she tried her best to suck. She'd only done this once before, and then it had been a lot easier. It's amazing how easy some things are when someone tells you that they love you.Chad's strong fingers clenched her hair, his member sliding deeper into her mouth. She looked up at him with glassy eyes, tears rapidly forming in their corners as he made her mouth bob up and down along his shaft, staining the meaty rod pink. For one moment their eyes locked, and she silently pleaded with him, knowing what was about to happen when she felt how he tensed up. A wide, stupid grin appeared on his face, and moments later thick wads of warm cum splashed out against her tongue. He pulled out with a satisfied grunt, leaving her coughing and panting as his seed ran from her mouth. It dripped down, staining the thin fabric of her pretty white blouse with large dark spots.
"Please…" She whimpered, "There's someone I lo- HMMPFH!??" Her pleading was cut short as someone yanked on her hair, forcing another swollen member into her mouth.
His pungent smell filled her as he pushed deeper inside, groaning with satisfaction as he felt her wet tongue coat his cock with its saliva. Up and down he forced her, ignoring her paroxysms as she started sobbing uncontrollably. She didn't want this. She had never wanted this. All that she had ever wanted was to make Gabriel love her back, and she'd confided her feelings to Samantha. The blonde girl had taken offense for some reason, as if the mere thought of Sophie laying her hands on that one boy was unthinkable.
The very next day she'd invited Sophie back to her house under the pretense of studying together, and before she knew it she'd found herself dressed like a girl. It had all been a joke of course, but it had quickly escalated beyond Sophie's control. Now she was here, feeling the erect cock of the wrong man press against the inside of her cheek. Tears ran down her abused face, carving deep channels in her makeup. Still the guy pressed on, unphased by her crying and pleading.
It wasn't long before his shaft swelled up, stretching her jaw wide open as he delivered his load right into her mouth. For the second time that day Sophie had done the unthinkable and let someone like this use her like a girl. It was one thing to dress up, to look pretty and play and pretend. But this? Sophie spat, desperate to eject his taste from her mouth. The palm of Bruce's hand came down on her cheek with a loud smack, causing Sophie to shriek in pain and fear.
"What the fuck is wrong with you? Here we are giving you what you want, and you can't even swallow? Put some fucking effort into it you stupid whore." He growled, grasping at her hair and roughly pulling her down to the ground.
She sobbed as her cheek scraped against the floor, drops of drool and cum feeling wet against her cheek. Bruce started doing something with the cuffs, but when she tried to look back she felt a foot on top of her head. It hurt something awful, and Sophie found herself weeping meekly. Suddenly the cuffs came loose, and for a moment she thought she was going to faint as the blood rushed back into her hands, leaving her in a dizzy state. The crowd came down upon her, a thousand needles pricking the skin of her hands as the jocks wrenched them upwards. She could hardly move her fingers after being locked up for so long, but they didn't care to wait. Instead their strong, callous hands wrapped themselves around hers, making her petite whitened reddened press against their shafts. Using her like she was some kind of toy they began tugging at her hands, masturbating themselves as they croaked with excitement.
She sobbed, doing her best to keep up with them. Somewhere deep inside she hoped that if she did what they wanted they weren't going to hurt her anymore. And so it was that when she was dragged back up on her knees, and the night's third hard cock towered over her face that she didn't wait for them to force her. The edge of her tongue was lolling outside of her mouth as she leaned forward, lapping carefully at the thick shaft. The boys laughter rang in her ears as she heard them berate her, hearing them call her name with scorn in their voices. She was nothing to them but a piece of meat to sate their primitive lusts.
Lowering herself, Sophie pressed her swollen lips against the man's balls. The sweaty musk permeated her mind as her tongue reached out and touched his sack. "F-fuck. This bitch is good." She heard the young man grunt, spurring her on to trail her tongue up along his shaft.
As she arrived at the swollen tip she paused for a moment, placing a quick peck on it before withdrawing. There she was, just a breath away. Her heart beat even faster as she closed her eyes, imagining that it was Gabriel She engulfed his member in the wet heat of her mouth and almost immediately she could feel him tense up. Fearing that yet another would come in her mouth she flinched, trying to pull herself backwards. But his hands found the back of her head, dragging her back down as he bucked his hips. She gagged, feeling his penis brushing up against the back of her throat. Air became scarce, and her entire body convulsed as she almost wretched. Thrusting into her at a steady pace the man roughly fucked her face, grunting like an animal and shattering any attempt at imagining Gabriel in his place.
The man grunted one last time, tugging harder on her hair, squishing her nose against his groin as he climaxed. His member twitched inside her, making her throat bulge slightly as he delivered load after load of his thick seed right into her gut. As he pulled out, one last rope of white cum splashed over her face, the sight sending the two guys using her hands over the edge as well. Sophie winced as they painted her pretty lips with their love, globs of cum dripping down onto the floor.
"There you go princess, well done. Now make sure to lick your lips." Bruce said, ruffling her hair affectionately.
Sophie gulped, the taste of cock thick in her mouth. "Please Bruce, please let me go…" She whispered, her voice hardly carrying.
He stroked her hair back over her ear, inspecting her battered face where tears, cum and muddled mascara mixed in equal parts. "No." He simply said as he stood back up. "Hold her." He ordered, and Sophie could feel strong hands grab her as she forced onto all fours.
She struggled the best she could, wailing and kicking as Bruce mounted her from behind, positioning himself so that she could feel his pelvis press against her pert butt. His eager hands came down on her rump, caressing the smooth fabric of her skirt.
"You always were girly Sophie, despite not knowing hot to treat your men. I'm going to help you though, and make you a real woman." He said as he hiked her skirt up, revealing her plain white panties.
Sophie's black pumps wiggled in the air as she squirmed, feeling Bruce's fingers wrap around the edges of her panties, pulling them down at an agonizingly slow pace. The calloused skin of his palm met her smooth white butt, and Sophie whined loudly as he squeezed.
"What's the matter darling? Are you going to cry now? I thought you were a big girl." He taunted her as he massaged her behind.
"F-FUCK YOU!" She screamed, anger flaring up inside of her. No. She wasn't going to do this. Not with him.
She struggled the best she could, but wasn't much of a match for the muscled young men of the football team. To them she was little more than a disobedient child.
"Ah, temper temper." Bruce mused as he pulled her thighs apart.
"NO PLEASE, OH GOD NO!" She howled as he aligned himself with her puckered entrance, the first inch starting to press into her. "No no no, please oh God no." She sobbed as Bruce took her innocence.
"Ah fuck me that's good." He sighed, his fingers digging into the doughy flesh of her behind.
At first her insides clenched down, trying to prevent the unwelcome invader's incursion. They remained like that for a while until her body started to relax, and Bruce could gradually sink himself deeper into her. Sophie cried, sobbing so hard that her entire body shook. She didn't want this, she didn't want him. Not him, not him, anyone but him. The thoughts rushed through her head. Had Samantha known about Bruce? He was halfway inside of her when he paused, his breath thick with lust as he spoke.
"I'm your first? I really thought you'd have given yourself to Gabriel at this point." He breathed, chuckling as he brought his hand down on her butt with a loud smack.
"Ouch! Please Bruce… Stop…" She cried, her heart flooding her veins with adrenaline. It had finally happened, she was really having sex.
"Shut the fuck up." He said hoarsely, pushing himself all the way down to bottom out inside of her.
Sophie shrieked with intense pain as she was stretched out beyond all reason, her wet inner walls tightly clinging against Bruce's thick member. With slow, deliberate movements he began pulling back and then thrusting himself forward again, picking up more and more speed as he went. Each time Sophie felt his pelvis crash against her ample butt she yelped, her crying slowing down as his pace quickened. Soon her sobbing was replaced by whimpering, and whimpering was soon replaced by small, reluctant groans of pleasure as the initial pain of her taking melted away. Reaching around in under her skirt Bruce grabbed her between her legs, laughing as he felt how Sophie's little girly cock desperately pressed against the confines of her chastity device. The plastic tube was nowhere near large enough for Sophie to have a proper erection.
Bruce leaned over her and she could feel his warm breath against her ear as he breathed into it. "I wonder what Gabriel would say if he saw you like this. I don't think he'd ever touch a little sissy like you."
He grasped her blonde hair from behind, yanking her head back harshly. "I'm going to cum inside of you Sophie, and you're going to be spent. You'll never be good enough for him now." He said through gritted teeth as he fucked her.
Sophie's resolve left her as she felt Bruce's words echoing through her, his pelvis slapping against her butt, driving the truth of his words into her. Soon his taunts grew infrequent and his voice turned into a mixture of heavy breath and groaning. What did she have left to offer anyone now that Bruce had taken her first time? He'd defile her, and she was never going to share this moment with Gabriel. Her strength failed her and her arms gave out, sending her falling down face first against the floor. The only thing that still kept her butt in the air was Bruce's hands around her waist as he kept pounding away at her.
She wasn't sobbing anymore, her tears depleted from the jocks abuse. Her blank face stared into nothingness as she was rocked back and forth, her cheek scraping against the floor all the while. For a good long while he used her, taking from her that most intimate moment. She'd dreamt about sharing it with Gabriel, but instead it was Bruce mounting her from behind, and it was Bruce's engorged member that suddenly swelled inside of her. Quick blasts of cum shot into her receptive hole, each load splashing against her insides with agonizing clarity. Each time felt like a blow far worse than when he'd struck her.
Bruce pulled himself back out with a satisfied groan, his seed trickling down from her stretched hole down along her thighs to pool at the floor around her knees. She fell as he released her, laying on her back quivering as her heart raced. Bruce laughed, high-fiving one of his friends as he panted.
"Jesus fucking christ, that was so good." He said as he stood over her, looking down at Sophie's petite frame.
When she didn't respond with anything but incoherent mumbling Bruce shook his head. "What's the matter with girls these days, they can't even fuck without going all limp and twitchy?" He jested, drawing more laughter from the boys around him.
Turning his back on Sophie he headed for the showers, leaving Sophie for the crowd to enjoy. He smiled as he heard her rambling voice grow louder, glancing back to see her legs splayed out before another one of the footballers. A sea of cocks surrounded her, more cum splashing out over her body. The young girl squealed happily as the man in front of her forced his member inside of her, her legs wrapping around him and urging him forward. This was going to be a long night for Sophie.
There were steps again. The loud clicking noises punctuating the compact silence, followed by the sound of someone flicking on the locker rooms lights. The fluorescent lights overhead flickered as they came to life. Samantha tilted her head to the side, a smirk appearing on her face as she saw her pet. Sophie's clothes were torn to shreds, hanging off of her beaten and abused body. Her wrists were tethered to the bench that was welded to the floor with the cuffs, the girl herself laying at her stomach, trying grind her pelvis against the dirtied floor. Walking up to her Samantha put her high heel against Sophie's body, turning her to the side. She giggled as she saw Sophie's member, still straining against the confines of its plastic prison. Was it possible that they'd all fucked her without letting her come even once?
"Hey Sophie, how are you doing?" Samantha asked, watching Sophie wince back like she'd been struck. Her eyes were half closed and dreamy, her gaze unfocused and distant.
"I'm talking to you." Samantha sad, irritated that her question had garnered no reply. Deciding to remind Sophie of her manners Samantha put her heel against Sophie's face, frowning as the abused girl's lips immediately wrapped around it and she started sucking.
"Oh my. They did a number on you didn't they?" Samantha said pleased, letting Sophie suckle on her heel for a little short while. "And what's this?" She asked, turning her attention to a note that was stuck to the locker above Sophie.
"Complaints.
- The whining. She whined like a bitch the whole time, forcing us to actually touch that sloppy ballgag of hers when we put it back in. Gross.
- The sucking. We shouldn't have to force her to swallow, it should be a privilege.
- The fucking. Please do something about the leaking. Her thing twitched and leaked the entire time. Gross."
The note finished with a scribbled date at the bottom which Samantha recognized as the date of the team's next game. Closing her eyes she smiled. "Looks like we've got some training to do."
Best Laid Plans
Tap tap tap..
Jamie let out a low groan, rolling over onto his stomache, to face away from his bedroom door, from where the annoying tapping originated.
Tap tap tap..
"Mmmm!" He groaned again in displeasure, dragging his pillow up and over his head, burying his face between the cool fabric of his mattress and the full softness of his pillow. His mind was thick with sleep and fatigue, it was probably just the house settling, he hoped futilely.
"Fuck sake.." came the gentlest of whispers in a frustrated, but feminine tone. His door gently creaked open then clicked shut, a moments peace and respite shattered as a finger poked him gently in the side. "Hey.. Hey dweeb.."
Jamie let out an exasperated sigh, rolling onto his back and displacing his pillow, using a slender bare arm to cover his eyes as he groaned. "Ugh.. Caitlyn.. What time is.. Is.." Jamie's mouth gaped open as he arched his back, yawning out deeply as he raised his arm to see, blinking into the darkness, just making out her silhouette in front of him. "The fuck.."
"It's a quarter past midnight.." she said softly and he could swear he could just make out the edge of a grin on her face.
"So whaaat?" he whined musically, pulling the pillow over his face and smushing it to himself with his hands, confuse and tired.
"Soooo…" she said in a mimicking sing song voice, her hand moving to pat him on his thigh through his duvet "That means technically it's Tuesday.. Happy eighteenth birthday, little brother.."
He squirmed out from under the pillow again to look at his sister. She sat on the edge of his bed, smirking playfully in the almost blackness. As his eyes adjusted to the dark (and to being awake..) he noticed she was just wearing her thick plush bathrobe over what he knew to be a very athletic figure.
While only one year his senior, they couldn't have been more different if they'd come from different families. While she was athletic and sporty, dark haired and dark eyed, an accomplished distance track runner, he was a slender reed of a boy, fair of hair and blue eyed, intelligent, but in his eyes he saw himself as being uncomfortably feminine. "Uhh.. I guess you're right. Thanks?.."
She smirked and raised up her hands, in one hand she held what looked to be a bottle and a pack of soda, in the other she held a game. He looked to her, blinking stupidly. She rolled her eyes, "You're eighteen dumbfuck. Lets drink to celebrate and play an eighteen on your xbox. One of my old favourites."
He stared at her, still half asleep and let his head roll forward in defeat. When she got something into her mind, there was little use trying to dissuade her. Though he didn't really realise just how far this would extend.. "...Fine.." he conceded, sitting up and letting his arms stretch out above his head.
Caitlyn grinned as he gave in to her, watching him intently as he sat up. She loved her little brother dearly. Because of her strength and his meekness she had become very protective of him. Recently, however, as she watched him grow up into the gorgeous young man that he was, she had become very possessive too, seeking to spend her time with him more and more, each day talking and gaming with him, each night laying in her bed, biting her pillow as she stroked her cock thinking about him, stifling moans of his name.
She had corrupted herself through these fantasies. From a loving older sister looking out for her brother into a predator just waiting for her meal to be ripe enough to pluck and sate her desires with, and looking at him now, she knew he was perfect. Like a vulnerable fawn, with a thick ass.
Jamie sat there blinking at her expectantly as he wiped the sleep from his eyes. He was small for his age, slender and nubile, his chest and chin hairless and smooth, his face rounded and feminine, no hard lines, no strong jaw. She bit her lip and felt her cock shift under her robe. For months she had been planning her brother's downfall in her mind. Taking him from being the lanky teen he was to stunning, eager cock sock.
"Come on~.." Caitlyn whispered enticingly as she slipped from the bed, shuffling across the floor and leaving the bottle and the cans behind her as she moved to switch on the tv in her brothers room, biting her lip as she sat with legs crossed, hands turning on her brothers Xbox and undocking the pair of controllers, looking across at him, her beautiful face lit now by the screen as it turned on, she smiled, encouragingly.
Jamie nodded a little as he slid off of his bed, he had the perfect little body for what Catlyn had in mind. She half watched him as he scooted across the carpet to sit besides her, his sleek body outlined in the faint light, wearing nothing but a pair of plain grey boxers.
As Caitlyn set the system up and put the disc in Jamie reached for the cans of soda, grabbing one and popping the tab. Hopefully it was something caffeinated.. He took a swig and a distinct bitterness passed his lips. He turned his head, swallowing, "Bleeeeh! The hell?!" he exclaimed.
Caitlyn having watched him take his first sip of beer held a hand to her mouth to quieten down her laughter, waving a hand at Jamie, "Shhh! It's just beer you dweeb, you're allowed to drink it now."
He poked his tongue out, setting the can down, "Ah.. No thank you, thats disgusting."
She rolled her eyes and picked up the can for herself, taking a hearty swig, feeling the cold carbonated drink slide over her tongue and settle any nerves. "Ahh.. Here.. Try this instead.." she said, pushing the bottle towards him.
He scooped it up and eyed it with no small amount of suspicion, a little less trusting of whatever might be in the bottle now than he had been just a moment ago. He twisted the top and set the cap down carefully besides himself, tucking his legs into one side as he lifted the bottle to his lips, glancing across at Caitlyn as he took a sip.
It was sweet, fizzy, fruity. Caitlyn smirked playfully as she watched him take his first pull at a pink bubblegum alcopop and enjoy it. She shook her head some. It was all too perfect. The way he sat, his choice of drink, he was going to be her bitch.
Jamie took another, longer, pull on the bottle and felt a little better about his abrupt awakening already. He settled in besides his sister, almost leaning on her as he unwound and picked up his controller, setting his bottle down by the cap.
"What're we playing?" he asked curiously as he looked to her with his bright, innocent blue eyes, running his hand through his short blonde hair to straighten it somewhat. She would have to make him grow it out.
"Deadspace three. The one with a co-op campaign." she said with a nod as the title came up and she ran them through the menus to load up the game.
"Ooh." he replied. He knew the franchise but had never played before, not really sure what to expect as they threw themselves into the game.
Over the next hour Caitlyn did everything she could to accomplish two simple goals, get him as scared as possible, get him as drunk as possible. The latter was easy as she constantly urged him on by handing him his pink alcohol, the former took a little bit of finesse, persuading him down corridors she knew to be laden with waiting necromorphs, having him play as Carver so he got some of the more creepy imagery.
By the time two hours had passed her little brother was quite drunk and all but nestled in the crook of her arm, drunk and quite freaked out. Just as she had hoped. Caitlyn herself wasn't exactly sober at this point, sure she had a much higher tolerance for alcohol than her little brother did and she hadn't been drinking anything half as strong as he had, but it was enough to lower any remaining boundaries and boost her confidence for the gentle romancing and seducing she had planned..
As they finished a mission she set her controller down, feeling the warmth of Jamie pressed against the side of her body.
"Well that was fun.. But you should get some sleep.." she said brightly as she shuffled away from him and made to stand.
"W-wait!" Jamie protested, blinking as he suddenly found himself leaning on his own arm and not his sister, feeling more than a little woozy, and more than a little freaked out. "I er.. Um.. Stay for a while? Talk?" he asked, trying not to sound as afraid as he felt.
Caitlyn smirked to herself but pursed her lips, as if questioning. "You sure you want me to stay? I mean it's pretty late.. You must be tired.."
He shook his head and looked at her, his eyes practically pleading with her.
"Hmm.. Alright for a while.." she conceded, sounding reluctant. She switched off the console and the TV. Their eyes having adjusted to the bright vibrant gore of the game made the room seem all the darker and full of shadows.
Jamie blinked, eyes going wide as he looked around, he couldn't see or hear his sister, but in his mind every corner lurked with necromorphs.
"Coming or what?.." Caitlyn asked, and Jamie turned his head towards the voice. As he did he heard the soft rustle of his bed sheets and his matress. Relieved, he moved across to his bed, stumbling as he walked, expecting to find her sitting on it. Instead he found her laying on it.
He bit his lip some, confused but keen to get out of the sudden seeming cold of the room and slid into the bed besides her.
Caitlyn throws the duvet over him, over them both and lay besides him quietly.
They lay there in silence for a few long moments, Jamie feeling a little awkward, laying in bed with his older sister because he's gotten scared of some stupid game, what was he, a coward
He all but jumped out of his skin when he felt a finger tip gently slide down his smooth chest, calming himself as he heard his sister's voice. "Mm.. Now you're a man I suppose you'll be bringing over all sorts of girlfriends and floozys now to occupy your time with.. You won't be needing me anymore.." she let out a soft sigh, loving the feeling his his smooth chest against her sensitive fingertips.
"N-no, of course not Cait.." he admonished, defensively. He might've been the little brother, but now he was a man, he felt some duty of care towards his sister.
"You mean you'll still want me?.." she asked, voice hopeful.
"Of course.. Jeez just because i'm a day older doesn't mean the world's changed.." he said, unsure why his sister was talking like this. Maybe she was as drunk as he felt? Or more so?
"Maybe it should.."
He paused for a few moments. "What do you mean?.."
"I mean I love you.." she said quietly, sounding the part of the quiet, demure sister, while beneathe the covers she lay, nude, her robe discarded in the dark, one hand wrapped around her rock hard length of her throbbing shecock as she threw her brother off by whispering sweet nothings.
Jamie frowned a little, this was very unlike her. "Well.. I mean obviously I love you too sis. We just don't go about saying it.." he responded slowly, feeling his mind muddled and his speech a little slurred, the hand on his chest so distracting.
"Can we cuddle a bit?.." she asked, voice soft and breathy..
"I mean.. Sure? I guess.." he replied, a little embarrassed. He was eighteen, why was she talking to him like a child.. He could hardly keep himself awake, his head spinning worse somehow, now that he was laying down.
Caitlyn smiled and slid forward, laying on her side she pressed her chest to him, her head resting on his shoulder, her body positioned so her ass pressed back, keeping him from feeling her throbbing cock quite yet.
She was nude! He felt her bare breasts pressed against his arm, warm and full, the soft flesh pressing against his body as she snuggled into him, he could feel the warmth of her breathe as it tickled his neck.
"C-cait.."
She pressed her finger to his lips. "Shh sh sh.." she urged, "You're mine.." she said, maybe a bit too soon but having her hard cock so close to his body and feeling him against her was speeding up her plans. She had intended on being all soft and cute, seducing him with warm words and an even warmer touch.
Jamie opened his mouth to object but Caitlyn pressed her finger in between his lips, over the ridge of his perfect teeth to slide across his hot wet tongue. "Mmmm!" he whimpered in objection, but wouldn't hurt his sister by biting down. She was so drunk!
She wasn't sure how the switch in her mind was flicked so easily, but her thoughts were no longer filled with the ideas of slowly seducing and corrupting her brother. She needed him and she needed him now.
She leaned forward and withdrew her finger, pressing her lips to his. He squirmed and whimpered into her mouth in surprise, but god's he was more intoxicating than the beer. His lips full and soft, his mouth hot and wet, he tasted so sweet, tasted so feminine, of bubblegum. She reached around with her hand and roughly gripped his short fair hair, driving her tongue between his lips to work his mouth.
He pushed against her, hands trying to find a perch on her shoulders to shove him off but she was too eager, too aggressive. She kissed him rough and passionately, taking advantage of his weak nature, of his inebriation to sate her own dark lusts and desires that had dominated her mind. He was so weak and beautiful, she couldn't resist.
As she forced herself upon him she reached up with her hand from her cock, gripping one of his hands at her shoulders and forced it down. While he writhed against her grasp she forced him to take the shaft of her cock into the gentle embrace of his hand. She wrapped her hand around his, gripping her cock and started to work her hips forward and back, fucking his hand as she tongue fucked his mouth.
Jamie's mind was swimming, his sister had a cock? How had she hidden that all their lives? And why she was kissing him? Was this a nightmare?.. Or a dream?.. He didn't know, he couldn't think, and she didn't care.
She had had everything laid out in her mind, some kissing, some teasing, maybe even be as generous as to suck his small cock and let him play with her breasts, slowly lower him into depravity before persuading him to touch her cock, urging him to kiss it, maybe getting her dick wet within a week..
She broke the kiss, panting hard. "Lay on your fucking stomache you little bitch.." she growled, not even giving him the chance to comply before she roughly shoved him, one hand pushing the duvets onto the floor as she rolled on top of him, sitting up to straddle him, forcefully tugging down his boxers, his only protection between her cock and his ass.
"C-caitlyn! Wha-"
"Shut up you slut!" she hissed, clasping a hand over his mouth. She watched as he writhed under her, with his slim chest, thin waist and plush girly ass, he reminded her of a young short haired cheerleader she had railed. She grinned. Though perhaps this slut was more girly. Or maybe this girl more slutty.
With her bulk pinning him by her thighs she watched as his small delicate hands tried to pry at the fingers on her mouth, her dark eyes filled with lust as she spat in her free hand, massaging her own spit into the shaft of her cock, taking a few moments to watch the drunk boy wear himself out as she slathered her cock in spit.
His flailing quietened as his muscles grew tired of flailing and she suckled eagerly on one of her own fingers, lavishing the digit with her own tongue before reaching down, feeding the finger between the plush pillowy ass cheeks of her younger fucktoy, biting her lip as she felt the tight ring of his hole against her finger.
She tightened her grip on his mouth and pressed her finger forward, penetrating and violating him, slowly sinking her finger into the yielding ring of his ass, lubed by her spit as she felt the incredible heat and tightness of his virgin hole squeeze down on her finger. It was like the little slut wanted it.
"Yeah you like that don't you.." she sneered as she felt his fight redouble, he was whimpering and squirming, helpless against her as she started to slowly work her finger in and out of his boypussy. She had completely lost control now. All semblance of a plan gone. She just needed a tight slut to sink her cock into and this little girly boy would do just fine, brother or no.
"I'm going to fuck you so good baby.." she purred as she finger fucked her new toy, the boy arching his back under her, to her eyes it looked like he was begging for it, though her perspective was incredibly skewed by her lust.
She drew her finger out, causing the boy to relax back into the bed, she could feel his hot breathe against the side of her hand as he breathed and whimpered hard through his nose. He was so fucking cute.
She spat on her cock and watched as her saliva traced down the lines and veins of her throbbing shaft to leave a trail down her sack where finally it dripped onto the bed sheets. Biting her lip she pushed her cock down, sliding her shaft between his heavenly, pillowy and oh so fuckable ass cheeks to kiss the tip of her slick cockhead to his virgin ass.
"Mm oh my god baby, give me half an hour with this cute little hole and you'll have a beautiful pussy perfect for my cock.." she moaned as she started to lean forward, pushing more and more pressure on the tightness of his slick ring, he let out a loud defeated cry as with some effort the thick tip of her cock pressed into the tight ring of his ass. She moaned feeling the tip nestled inside him, where it belonged.
With her cock now stuck inside him she moved her hand from her own cock and lay her body down on his, feeling the smooth warm skin against her toned body, letting him feel her lush breasts rest on his back as she gently nibbled at his ear, playfully, smelling the feminine scent of his shampoo.
She used her strength to start urging her hips forward. His asshole stretching wide to accommodate her as she fed inch after inch of her shaft into his girlish butt, he groaned and whimpered, letting out soft feminine noises as she dominated him, lost in the sensation of his tight hole hugging her cock.
She whispered now, not even thinking about what she was saying, just venting months of dark fantasies as she finally began to sate her lust, "Oooh fuck.. You're going to be my little fuck toy.. The perfect girlfriend.. I'm going to dress you up like a little slut.. Fuck your pussy till you beg for more.. Mm.. Gonna get you on those hormones, get you the perfect pair of bitch tits to slide my cock between.." she groaned as half her cock now rested inside him.
Tears rolled down his cheeks at the intense pain and fullness that now dominated his senses. He'd never felt like this, felt so violated, felt so intensely intimate. He was so conflicted, this was his sister! His beautiful sister, who he admired and loved, whom he'd wanted to do so much more with, now fucking his ass, saying these lewd things, dominating him, making him feel helpless.
She grunted as she pressed more and more of her cock into him, not letting up, not letting him relax, unsympathetic of his pain and caring only for the amazing sensations now embracing her cock.
Finally, somehow, she hilted inside of him, going limp on top of him as she simply relished the sensations. The ring of his ass kissing the base of her shaft, her full heavy balls resting against his much smaller ones, demonstrating her superiority and just how natural it was for him to get fucked.
She ground her hips into him as he panted and whimpered, loving the sensation of his doughy cheeks pressed against her body. "Fuck you've got such a cute little clit.."
She moved her hand from his mouth down to his neck, squeezing slightly, her other hand moving to roughly grip at his flat chest, catching his nipple between her fingers and pulling.
He let out a loud gasp as his mouth was freed and started to speak, but as he did she squeezed his neck, choking him and stopping his words short. He panted as she relaxed, again trying to speak but again she cut him short with a squeeze. He got the message. No talking.
He panted hard, tongue lolling as he regained his breath and let out a low relieving moan as she slowly drew the length of her cock from him till only the tip remained, the void it left in him was, to his horror, uncomfortable.
She didn't let him experience it for long, the void in his ass was drawing her back in, practically sucking on her cock as she fed it back into him, eliciting a humiliatingly feminine moan from him.
She grinned, "Yeaaah you fucking love it don't you, you little bitch.. You've been waiting your entire fucking life to worship my cock.." she teased as she started to fuck him for true, feeling his tight little hole milking her needy shaft as she pressed in and out him, using him for all he was worth.
Their bodies met again and again, her hips slapping into his plush cheeks as she drove into his tightness again and again, panting lustfully into his ear as the slick noises of his ass and the collision of their bodies echoed through his room, mixed with his girlish whimpers and moans.
When he got too loud she squeezed his throat, when he squirmed too much she squeezed his throat, when she felt he wasn't squeezing her cock hard enough with his boy pussy, she squeezed his throat. She was leaving a bruise she knew, but as she fucked him she couldn't care less.
His hands clawed at the bedsheets as she pounded him, his whole body shaking with the force of her thrusts. Her attitude, he could feel was changing, she was squeezing harder, she was talking less, her thrusts were shorter but harder, only pulling a few inches out before slamming back in.
Her hand tightened around his throat and she bit his ear hard, leaving him gasping, bright blue eyes wide as he squirmed helplessly. "Take my cum you fucking barebacked bitch.." she hissed, grunting as she hilted herself inside him.
He felt the cock throb, felt it pulse and felt a sudden, foreign feeling, a liquid heat surging deep inside his tight little body, he couldn't breathe, even her voice was becoming more distant as he felt her empty herself deep inside him, claiming him. Owning him.
His ass was so perfect, the pleasure coursing through her every nerve as his ass squeezed and milked her cock, like the perfect little cock sleeve.
As his eyes started to roll back she released his neck and let him lay there, hard cock hilted in his bred body, muscled sister laying atop of him as she drained every drop of her thick milky seed into him.
She relaxed on top of him as they both panted to recover, letting her cock slowly deflate still lodged inside of him. Between the hard fucking, the choking and the alcohol she knew he was going to spend the morning learning about hangovers.
She kissed his neck softly, tenderly, feeling a little guilty, but not enough to change the path she had set herself on, she watched him, exhausted, spent and falling asleep under her. "I do not envy the headache you will have when you awake.. In the meantime, dream of my fucking cock, slut.." And she closed her eyes.
Reality Check
Jamie awoke in pain. A lancing, throbbing pain that seemed to echo through every inch of his mind body and soul. A loud piercing beeping which seared into his mind like a hot poker spearing his mind and resonating throughout his whole body. He forced his eyes to open a fraction and the dull rays of scarce light stretching through his room caused the pain to double as they burned into him.
He let out a low,despairing groan and reached his hand out for his smartphone, besides his bed, where he had left it the night before. His hand was uncoordinated, slapping around to find it and after fumbling with it for a few seconds, he pressed the button on the side and cut short his morning alarm before flopping back onto his face and letting out another, more mournful groan as he pulled his head under his pillow, trying to arrange his thoughts now. The beast of noise and light had been slain. His head hurt. Why? Had he been drinking? His console was out, why? Yes.. He had gotten drunk and played a video game.. With.. With Caitlyn? That made sense. But his ass, why did his ass hurt?.. Why would?..
He sat up sharply and looked around him, ignoring the explosion of blossoming, sudden pain in his head as he inspected his immediate surroundings. He was alone. No Caitlyn. He felt himself relax again at that realisation, as he looked around his room through squinted, blinking eyes.
Sitting beside him on his bedside table was a tall glass of water and a few tablets. There was no note but he recognised the tablets as being aspirin. He took the tablets with a mouthful of water, pausing to breathe a little heavy, a wave of nausea sweeping through him at the pain and effort the moving had exerted on him and took a few more mouthfuls of the water before laying back onto his bed, slow and careful, staring at the ceiling as he tried to piece together fragments of the previous night.
His ass was burning, a pain he'd never felt before, a pain he didn't understand. His mind was screaming at him, trying to warn him what it was, but he refused to believe the truth his mind was showing him. That couldn't have happened. Could it?..
He winced a little and felt uncomfortable in his thoughts, absently he reached a hand down. His boxers weren't there, they were down around his knees. He had his duvet, but he cast that aside, leaning up and looking down at himself. His cock was soft but coated in dry cum, he frowned as he looked at himself, boxers half off, covered in his own sticky seed. There was a distinctive stain beside him too. Like he had jerked off and came into the bed. Was that it? Had it all been a wet dream of his? That didn't account for the pain he felt but it was less of a bitter pill to swallow.
He hesitated a little and thought about checking his ass, but no. He wouldn't, he was afraid of what he might find. He lay back down on his side, to relieve the pain from his ass and closed his eyes. What if he had.. What should he.. Why would... Sleep took him from his unanswered questions and he dozed back off into a troubled sleep.
When he next awoke his head wasn't exactly clear, but it was better for the water, aspirin and sleep. He would be tender, but not incapacitated. He sat up and groaned a little, feeling a tenderness in his ass and weirdly at his throat. Still, it didn't bother him. It hadn't been real.
He sighed and swung his legs out of bed and stood on wobbly feet, pulling his boxers back up into place and running a hand through his sandy blonde hair as he gathered up the half full glass of water and drained it, rolling the glass around hesitantly in his hand as he looked towards his bedroom door.
Today was his birthday, he was eighteen today. That should've made him feel like a man but he just couldn't muster that feeling. He felt more a child in need of reassurance than he had in years.
He set the glass down on his side table with a slight clunk and picked up his phone again, standing beside his bed as he unlocked it, checking the time.
One in the afternoon? He'd slept half the day away! He sighed some. "Some birthday.." he muttered to himself and set his phone down, locking it and making for the bathroom.
After brushing his teeth and using the facilities he flipped the shower on and got a towel together, stripping out of his boxers and stepping into the heat of the shower, closing his eyes and letting the hot water stream across his body, washing away his tiredness and the majority of his aches.
He glanced to the side as the water washed over him, cleansing him and noticed a small compact makeup mirror beside the sink, just inside of his arms reach.
He couldn't, what would he see? He swallowed. His hand reaching out, water trickling down his fair unblemished skin as he picked up the mirror, pulling it into the shower and looking at it.
He held in his hand pandora's mirror. If he opened it up he would unleash its contents into his mind. Or maybe it was Schrodinger's mirror. Until he looked into it, he lived in a state in which last night's events had both happened and not happened.
He opened the mirror and brought it up to look at himself. Seeing his soft blue eyes, his familiar and all too feminine face. And to his absolute horror, bruises on his neck in the shape of a hand. It was real. It had all been real. He turned around, all but throwing the compact mirror back down by the sink, in denial about what he had seen.
He froze, the mirror skittering around the bowl of the sink before it came to settle. In the bathroom doorway stood his sister. He hadn't even seen or heard her open the door. But she watched him now, smirking, her expression dark. Caitlyn was athletic by nature, not bulging with muscle but toned and strong, built for a purpose. He knew this, knew it with far too much detail in fact. Before him in all her glory, the purpose she was built for was becoming more and more obvious, transforming him into her plaything.
His eyes trailed down her body, from her beautiful face, across her buxom chest and flat toned abs to her cock. Terrifying in its familiarity to him, it stood proudly out in front of her, erect and pressed forward slightly as if it was leading her to him, a dousing cock.
"Admiring my handy work?" She asked softly, closing the bathroom door behind her and smirking as she locked the door, something he had omitted doing.
"Caitlyn... " he said her name in a tiny, terrified voice. He didn't know what to say. He was overwhelmed with the sudden, undeniable truths of the night before.
She could see the terror and anxiety plain as day on his face and in his voice, her eyes drinking in the sight of his nude, glistening form. He was so beautiful, so svelte. He would fit her needs so nicely.
"You're going to bend over for me right? Offer yourself to me like the good little girl you are?" She teased as she sauntered casually towards him. Watching eagerly as he backed himself into the corner of the shower.
She smirked and stepped inside with him, feeling the water wash over her. She let out a soft sigh of pleasure and looked at her little brother, huddled in the corner. "Don't worry sweetcheeks. I'm not going to fuck you." She said as she tilted her head back, running her fingers through her long dark hair as the hot water saturated her locks.
"You.. You aren't?" came Jamie's quiet voice, sceptical, nervous.
"No.." She paused, opening an eye to look at him with a smirk. "I mean, unless you want me to of course?"
He shook his head meekly and stood again, swallowing anxiously as he started to move to climb out of the shower, his fear obvious.
She reached out a hand and wrapped it around his wrist, vice-like, stopping him in his tracks, leaving him frozen, like a deer in the headlights.
"Wash my back?" she said softly, eying him with a smirk.
He relaxed and just nodded faintly, reluctant but not wanting to prompt a worse fate. Subtly, he rubbed at his reddened wrist as she released her grip on it. She leant forward against the shower wall with one hand, the other gliding down her toned feminine frame to wrap skilled, experienced fingers around her water soaked shaft, slowly starting to work it, relaxing and waiting.
Jamie glanced back towards the door as he stood behind her. Could he be out of the bath and to the door before she had time to react? But what then? Would he run down the street naked? No, she would grab him, throw him on a flat surface and have her way with him, again. The thought alone made a shiver run cold down his spine.
Swallowing, he applied the soap to his hands, warming it before moving to start rubbing his hands against the smoothness of her back. He moved his hands in slow long movements up and down her spine and Caitlyn found herself matching the stroke of her cock to the gentle caresses of his hands on her skin. Each touch was an electric jolt of pleasure up her body as she idly played with herself.
"Wheres… Wheres mom?.."he asked, afraid to raise his voice and spoil her reverie, but he assumed she would've been in today. But if Caitlyn was acting like this, she had to be out.
"Mm at work.." She confirmed, "They're being audited this week and they called her in.. She was sorry to miss you but said she would see you this evening." she glanced over at him and grinned, "so you're all mine until then." she said, a small excited note ringing in her eager voice.
He bit his lip anxiously, all day at her mercy? That wouldn't bode well for him and he knew it. He kept quiet for a while, lathering her back to the point where it was more a massage, albeit an amateur one, just trying to stall for time, though for what he didn't know.
"Mm.. Don't say I never do anything for you, babe.. But I got you a birthday present.." she said, her voice droning with an undercurrent of pleasure.
He paused, causing her to arch her back wistfully, desperate for him to continue touching her with his soft feminine hands.
He continued his actions, but his voice was lined with a sceptical paranoia, "..Like what.."
"Mm.. You'll see.. But it'll take up your entire day.. What's left of it.. " She said, glancing over her shoulder at him, with a smirk, enjoying the mix of expressions on his face. She knew a part of him was enjoying her body. Her skin under his hands, her ass in his sightline as he looked down. His confusion was simply adorable.
"But.. But I'm meeting with my friends later.. We're going to the cinema?" he protested meekly, he had hoped that trip would offer him some respite from this waking nightmare, and maybe even some time on his big eighteenth, where he could make some nice memories.
"You'll enjoy this more. I know it." She said voice assured. "Besides, I already messaged your friends and told them you were sick. They were very sympathetic! You can go with them next week." she mused in a sing-song voice.
Jamie felt his heart sink. There would be no reprieve for him today it seemed.
She let out a soft purr, "Good job on my back. Now kneel down.." she urged, biting her lip as she stood in the heat of the shower, stroking herself and feeling her pets hands running across her back.
He hesitated, but only for a moment before sinking to his knees. His situation was dire, yes, but it would be worse if he tried to fight or flee. He could only submit until an opportunity to gain freedom was presented to him.
With no such avenue of escape here and now, he found himself on his knees, face to face with his sisters round firm butt. Hands trailing up her strong thighs to rest on the enticing piece of his sister. He blushed brightly as he started to rub the soap into her sister's ass, eliciting a moan from her. "Good girl.."
From this angle he could better see the movements of her arms, knew that she was jerking off the cock that had fucked him just last night, but chose to ignore it. If he could pretend that thing didn't exist, he might just be able to enjoy himself for a moment.
For all of his trepidations, the thought that this was his sister he was kneeling behind, whose ass he had fantasised about more than once under his covers, had his dick swelling.
He ran his fingers up and down the firm cheeks of her ass, pressing in and enjoying the warmth of her flesh as it slipped under his soft soapy fingers, eliciting moans from her. He massaged her cheeks, exploring them with a warm blush as his own cock stiffened between his thighs, unable to deny the lust he felt, no matter how wrong this was, or how cruel she was.
His hands roamed across and around her ass, even moving to slip down her thighs, testing the firmness as he did so, biting his lip.
"Kiss it.." Caitlyn said softly, her voice low and breathy as the slick sounds of her hand around her cock grew harder and harder to ignore.
He swallowed, but leant forward, pressing his plush soft lips to her firm ass, leaving soft little angel kisses around the swell of her enticing cheeks.
She giggled and arched her back a little. "Nooo not there sweety.." reached back with both her hands, releasing her throbbing cock and let her fingers grip her cheeks, parting them, revealing her rosebud to him as she looked over her shoulder, down at him. "Here."
He looked up at her, eyes wide, admiring her beauty but recognising a spark in her eyes. He remembered last night how she had gone from kind and loving to… He didn't want to think about it. Or trigger whatever had done that to her.
"O-okay." He stammered and nodded weakly. She smirked and winked at him before turning back to the wall, pressing her spread cheeks towards him, enticingly.
He bit his lip and gathered a drizzle of soap, running his fingertips down the crack of her firm athletic ass, causing her to gasp at the coolness.
"A-ah! Hey~" she chastised playfully, but not too hard, enjoying his fingers rubbing up and down across one of her most sensitive spots, and certainly her most private.
He thoroughly washed her before letting the water, racing down her back and travelling through the crack of her ass, rinse away the suds. He stared at her, hesitating, his own cock throbbing between his thighs, pointing straight up towards her.
"You're making me impati..Oh!" she was interrupted by the feeling of his smooth face nestling between her soft cheeks and those oh so lovely lips meeting her little hole in a kiss.
Her eyes rolled back at the forbidden and oh so infrequently indulged pleasure as she felt his tongue begin to trace circles around her hole. She released her grip on her cheeks, letting them press in on them for a moment before she felt his hands once more on her cheeks, spreading them for himself.
She placed one hand back on the wall for support as the other got back to work on her thick shaft, chewing on her lip as she moaned and squirmed against him.
"Oh.. Fuck you're such a good girl.." she complimented, causing him to blush as his tongue worked in a slow circle around her rosebud.
He lavished her with his tongue, running it over and around her hole, occasionally trying to press it inside but she was too tight, or he wasn't keen enough, whichever it was she didn't seem to notice or mind, enjoying what he was giving her.
He knelt there until his knees started to get sore, he had been so lost in his toying he hadn't heard her heightened moans nor her quickened breath.
She pushed him back and to his surprise, he let out a little regretful noise. She turned, facing him, and as he looked forward his little patch of heaven fell away to reveal the less desirable truth.
Jamie found himself at eye level with her cock, seeing it clearly and close up for the first time in his life. It was terrifying. Long and thick with a dark mushroom tip, flawless in its design, intricately woven with veins, accompanied by two huge smooth balls. He looked up at her, eyes wide, the fear rising again within him.
She cooed softly. "Look at you.. All hard for me and ready to finish me off.." she bit her lip as she reached down and tangled her fingers in his wet hair, pulling him closer so her cock brushed against his cheek, leaving a smear of precum as she moaned a little.
"Put it in your mouth baby girl.. And if you so much as think of even touching it with your teeth, I'm going to kick your balls until they burst and punch your teeth out.." she growled. Jamie genuinely wasn't sure if she would do that to him. Before last night he'd have never believed it, but kicking the shit out of him almost seemed a step down from what she had done the night before.
He looked up at her, at his sister, they'd known each other all their lives, lived together, played together, loved each other as a family. Looking down at him, she had to see that didn't she? Had to see her little brother in need of love and affection? If he could just appeal to her, just get her to see him like that again, maybe he could save himself, get a reprieve, "Caitlyn, we-Mmph!"
The second he opened his mouth she nudged her cock forward, tilting her head back and letting out a victorious little sigh of pleasure as she fed the tip of her cock into his open mouth, "Oooh you slut that feels so good.. Good girl.."
Jamie raised his hands, pressing them against her thighs, which she countered by placing another of her hands on his head, gripping him as her powerful glans filled his mouth. It was massive, hot and firm yet spongy against his tongue. He tried to push against it with his tongue, tried to twist free of her strong grasp!
"A-ah fuck.. Yes.. Yes, use your tongue.. Oh fuck that feels good.." She was holding him in place almost effortlessly as he struggled, she let out a low moan and fed a few inches into his mouth, causing him to whimper in distress. As she pulled back a drop of pre wiped on his fleshy tongue, forcing him to taste the entree of what was to follow.
She settled into a slow rhythm of fucking his mouth, looking down at him over the swell of her breasts to see his girlish lips glide up and down her girl cock, his expression one of fear, panic and revulsion. "Aww poor baby.. You don't like my cock? You'll learn to love it like the cock sock you are.."
He looked up at her and his fear doubled, the tone of her voice was getting darker, more vulgar. This. This he remembered, all too well. He slapped at her thighs, trying to pull free but that only spurred her on, her fingers pulling painfully tight on his hair as she dragged him forward and backwards, jerking her hips as she moved.
"Ooh my fucking god yes.. You know, I was just going to jack off onto your cute little girly face.. But I think I've got a much better idea.." she grinned darkly and angled herself differently so her cock was pointed down, hands gripping his head as she started to work her hips down, sinking her cock into his mouth.
He squeezed her thighs, patting them helplessly as he squeezed his eyes shut, whimpering and squirming under her, as he felt the crown of her cock slip deeper and deeper, pressing under his tongue.
He let out a soft, gagging, wet sound as the tip of her cock poked against his throat for the first time and he realised what she was planning, he coughed and gagged on her, pushing uselessly against her, finding himself once more completely at her mercy.
He looked so fragile, so beautiful, like a supermodel, choking on her cock. So light and feminine. She could hardly wait for tonight, after his birthday present. But he could do better.
"Come on you fucking slut you call that deepthroating me? Just stop gagging and fucking take it!" she snarled, uncaring for his pain and discomfort now, only caring about sheathing her sword. She used her strength to overrule biologies simple 'that doesn't belong in there' manifesto, pulling on his head as she lowered her hips down. "Stop squirming! Fuck!"
He didn't, he couldn't help himself, he moved his hand to her cock, gripping it at the base and squeezing it, trying to pry it free from his mouth or at least deny more of it from entering as it pushed against his throat, but the action only caused her to moan, "Yeah I knew you fucking wanted it! Wanted my cock!"
She bit her lip and drove herself down. Jamie's eyes snapped open in shock and pain as the thick tip of his beloved sister's cock forcefully penetrated his throat, filling it and dominating him fully.
Past the tightest point the force and pressure she was exerting on the boy gave in an instant, the mushroom tip of her thick edging cock plunging down his throat to fill him, his plush angelic lips wrapped tight around the base as he pressed desperately against her, his face turning red at the sharp foreign pain of having a huge thick cock rammed down his virgin throat.
"Oh yesss.. I knew you would be the perfect deepthroating bitch.. You're going to fucking learn to wake me up every morning with my morning wood balls deep in your fucking tight ass throat.." she growled as she gripped him, holding him deep as she ground her balls into his chin, watching him squirm.
"Won't take long slut.. Just suck it up and take it like a bitch.." she grinned as she drew her cock out until only the spongy, saliva coated tip rested on her tongue, giving him the luxury of half a moment's reprieve for him to draw in a breath before she forced herself back in again.
He held onto her thighs, tired of trying to push away and just trying to survive, his mouth was forced open uncomfortably far, stretching his lips around her shaft as the tip pressed over his tongue, delved deep into his tight throat before venturing back up again in a brutal rhythm. He could feel the heat of it, every ridge and line as it penetrated him, never given enough time to truly draw in a breath and recover. Not that she cared in the least at this stage.
She panted hard as she looked down at him taking his cock. From her point of view, ears muted to his chokes gags and whimpers, blind to his colour and inability to draw in a breath, all she saw was a natural born cocksucker, skillfully throating her cock like he was in love with it. "Yeah, I knew you would love this.. So fucking much.."
She tilted her head to one side and was satisfied to see his slender pale neck visibly bulging with her cock with every single thrust, she could almost even make out the distinction of the ridge of her tip in the outline of his tight, cock swallowing throat.
The bathroom was awash with wet noises, the soft pattering of the hot water striking her muscled back, the deeper slicker and more viscous noises of her darling plaything throating her cock, the ragged desperate gasps for air. It spurred her on but she managed to control her tempo, doing everything she could to stave off her climax. She could only rob him of his oral virginity once, she wanted it to be memorable.
Jamie, however, couldn't take it anymore, the pain in his throat was mounting, the burning in his lungs intensifying, he wasn't getting enough air, already the room was spinning and he knew, soon he would black out. And gods only knew what she would do to him if he did that. He had to put a stop to this, end this ordeal. But he couldn't force her off, even at his best, she was just too strong. He could, however, make it end quicker.
One hand slid up her thigh and between her legs without her noticing, her head tilted back as she lavished in the pleasure, he waited, waited until her tempo quickened, her deep brutal thrusts short and desperate, her cock hardening to steel as it prepared to cum, a point where the last few times she had slowed down to delay the inevitable, and he moved, moved to cradled her balls in her hand, lifting and gently squeezing them, trying to urge her to cum.
Caitlyn gasped in surprise as she felt his hand on her, in her mind, in her fantasy, he was already a willing talented little cock slut, but the hand coaxing out her load was no fantasy, she looked down in surprise and saw him looking up at her, with those big blue blowjob eyes. Wide and beautiful, so innocent and tempting.
She was so lost in that delicious gaze that she hadn't sensed her climax approaching until it was too late, she passed through the threshold of no return and felt her balls surge with cum, she gasped and hilted herself inside of him, every thick throbbing inch of her girl cock pressed down his throat, pulsing as his hand massaged her sack, drawing out her thick seed.
Her cock pulsed in his throat and he did his best to maintain the eye contact, so oxygen starved he didn't even realise that with his objective achieved he could stop his extracurricular activities of working her balls. Each pulse of her cock stretched his throat painfully and he felt an odd blossoming heat in the pit of his body. She was depositing her load straight into his stomach, where, in her mind, it belonged.
She looked at her sweet obedient little bitch, her mouth open and her tongue lolling as she panted, cumming down his throat, staring down into his gorgeous eyes, feeling his hand eagerly helping her along. This could only get better, she knew, each time she played with him he would be a little less resistant, a little less prone to rebellion. He would fight and he would lose.
Jamie felt the room spinning, a dizziness sweeping through him as his lungs burned, too long, his face started to turn blue and his eyes started to roll back, his vision twisting, fading as the steely length down his throat denied him any reprieve, just pulsing, pulsing, pulsing…
She drew her cock from his throat, one hand matted in his hair the other around her length stroking it, aiming to land the last few strands on him, painting his pretty little face white with her 'affection' as his head lolled forward limply and his eyes snapped open, drawing in a loud intake of breath as he raised his head, his smooth chest rising and falling rapidly as he pulled in lungful after lungful of sweet, sweet air. He felt the hot streaks against his face and neck, not many, as she had fed most of her load to him.
His eyes focused and he looked up at her, her cock flagging as it drooled a little line of cum down to lay across his chest, his own cock painfully erect, he noted. She was smirking, a smug self-satisfied look as she gave her shaft a few final jerks, savouring the moment, another moment of his defeat and her victory.
She stepped past him casually and from the shower, feeling the enticingly warm and soft mat on the bathroom meet the soles of her feet and toes. She let out a happy sigh, not turning to face him as she collected a towel and wrapped it around herself, sated once more.
"Mm.. I needed that.. Thanks babe." she glanced over her shoulder at him, kneeling in the water, panting as he tried to recover, a couple strands of her cum across his feminine features.
"Clean yourself up cutie.. Your present will be here in half an hour." She winked, voice playful and teasing as she sauntered from the bathroom, hips swaying, shutting the door and leaving him alone.
He paused for some time, just kneeling in the stream of the shower as the water washed off her strands of cum, but did little to wipe away the pain in his throat or the shame for what he had done, let alone the shame for the erection that still stood proudly between his thighs. What was happening to him? Was he enjoying this?
A sharp knock rang out on the bathroom door. "Hey! Hurry up! She'll be here any minute!!"
She? She? What the hell was his birthday present, what was she planning? As afraid as he was as to what it might be, he was more afraid as to what she would do to him if he hid in here. So with pain and reluctance, he stood and switched the shower off, bracing himself mentally for whatever she had coming next.
Lust and Lipstick
Confusion and anxiety dominated Jamie's sore, battered body and mind. It was hard to maintain a positive outlook on things when your positive outlook became, 'I hope it doesn't hurt so bad next time.' There was nothing to look forward to anymore. And the fresh horror that was the mystery of his upcoming birthday present only served to set him even more on edge.
His fear of Caitlyn's wrath, however, now twice experienced, spurred him on to quickly finish his shower and start toweling off, grateful for the steamed up mirrors, allowing him to avoid his own image, something he couldn't bear to even glimpse right now as his mind was dark enough without adding the vision of himself, downtrodden and beaten.
He stepped out onto the landing, the towel wrapped tight, almost guarded, around his waist. He shuffled as stealthily as he could towards his bedroom, hesitating near the top of the stairs, hearing voices. He gently brushed his warm, wet hair away from his ear and bit his lip, trying to listen in.
"...And I just thought you would be better to help with this than me?.." came his sister's voice.
"Oh, the poor little thing. I had no idea!" someone else, though he almost recognised the muffled voice, which paused before continuing, "Well, actually it's not that surprising.. But I would be so happy to help! It's going to be so much fun!"
Jamie blinked as the voice finally rung true in his mind. Kelly, no doubt about it. Kelly was one of Caitlyn's friends from the last few years, she was around the same height as Caitlyn, her eyes and hair the same dusky darkness as his sisters own. She wasn't quite so toned and athletic and while she shared Caitlyn's slenderness and curves, her body lacked the definition of muscle. An aspiring actress, he remembered.
She had also been Jamie's first and longest running crush, the girl of his dreams. She was so similar to Caitlyn, he guessed, who up until recently had been both secretly desired and forbidden fruit, Kelly had offered the budding sexuality of a boy someone to jack off to, guilt-free. That and she had always been sweet on him. Something he desperately needed right now.
He made his way to his bedroom and was quick to dry himself off, his blonde hair was still damp with moisture as he pulled on his clothes but he didn't want to miss her. He found himself having to wiggle as he slid the tight jeans over the curve of his hips and selected a t-shirt from a pile of rather crumpled clothes. It wasn't exactly the perfect ensemble for greeting his crush but he was low on options.
He hurriedly made from his bedroom towards the stairs before stopping for a second, he had to remember that whyever she was here, she was here because of Caitlyn, which made him fear it could only end badly for him.
He quietly stepped down a couple of stairs, trying to see if he could steal any snippets of conversation before they noticed him.
"Mmhm! Back to the house no later than ten. That way our mom will be out again.. Will that be alright?" His sister asked.
"Deal. I'll keep an eye on my phone." Kelly responded, though the context of their conversation still evaded him.
He stepped downstairs and into the living room, finding his sister leaning against one of the coffee tables, nodding and smiling at Kelly who sat in the armchair, leant forward, eyes wide and eager! As he stepped into view, he looked cautious, anxious, maybe even a little afraid, the sight of his sister instilled that in him now.
"Aww! Jamie you poor thing come here." Kelly stood and crossed the room in a flash, wrapping her arms snugly around him and pulling him into her warm embrace, her full C cup breasts pressed close against his face. She'd never really paid him much attention and he wasn't exactly sure what Caitlyn had said to her, but this seemed good at least?
She pulled back and smiled brightly down to him, running her fingers through his damp hair to straighten it into some semblance of decency after he had hurriedly dried it. "You're so incredibly brave. God, we're going to have such an amazing day today! Just you and me!"
He blinked from Kelly to Caitlyn, expression blank and uncomprehending, he could see Caitlyn hiding a smirk.
"I told you, Kelly, that he would be very shy and insecure about it.." she said with faux concern lacing her voice, "But that's no surprise, coming out as trans is a big step for anyone."
His eyes widened at her words. She had told Kelly that he wanted to become a woman? He opened his mouth to protest but stopped just in time to consider his situation and whether or not speaking up would be a smart move. If he went against Caitlyn now it would not bode well for him. And what was it Kelly had said right now? Just him and Kelly all day? That… That sounded like a pretty good birthday present if he was completely honest with himself.
"W-where.. Where are we going?" he asked, looking up to Kelly, voice soft and anxious. He realised he was playing right into Caitlyn's hands. His timid voice, his demure demeanour, Kelly would see a delicate little woman trapped inside the wrong body, afraid and uneasy to reveal this secret to the world, not the truth, that he was afraid of further tyranny and abuse courtesy of his sister.
"To the mall silly. As girlfriends!" she said looking bright and happy. He'd seen her hanging out there occasionally, flitting from shop to shop with a gaggle of girly girls which very seldom included Caitlyn. The two of them seemed to connect over something deeper than shared interests.
"And it's your birthday little sister. So you better have fun. If you don't have fun and open up, Kelly will let me know okay?" she said, voice light and pleasant, though the undercurrents of her words were sinister. Be good and do as you're told or she'll know.
"I'll.. Do my best?" he said, trying his best to smile and overcome his worries, maybe he could actually enjoy himself?
Perceiving this as bravery, Kelly clasped him into another tight hug! She was seemingly giddy with the idea of spending the day with him, which was something he would never have expected but it made him feel secretly hopeful at the same time. A soft blush teased at his cheeks as he felt himself starting to relax.
"Come on Jamie, let's not waste any more time!" she beamed, taking him by the hand and leading him towards the door. He glanced back towards his sister who stood there with an unnerving smirk on her lips, waving towards him. Something in her eyes made his anxieties flutter.
He moved to pull his shoes and coat on. Kelly meanwhile, was already outside the house and heading towards, what he assumed, was her car. He shot his sister one last parting glance but she merely blew him a kiss and shooed him away.
Sighing he closed the door and walked after Kelly, following her down the driveway. As he walked towards the car she opened the door to the passenger side for him, pursing her lips as she seemed to over-critically eye up his choice of clothing, which he couldn't really blame her for, he wasn't exactly dressed up for a date, male or female in his crumpled casual clothing.
He slid into the comfortable passenger seat and she closed the door politely behind him, treating him like the girl she saw him now to be, making her way gracefully around the car to slip in beside him.
She let out a soft happy sigh as she flopped down in the seat, turning her keys in the ignition to set the car humming. She smiled prettily, reaching across and giving his thigh a soft reassuring squeeze as she pulled her seatbelt on. "Your sister's been very generous with her money today for your birthday, between her and me we've got this all planned out for you!"
As she started to drive she tuned the radio into a station playing a score of pop songs that seemed to be selected from the year's most played and oversaturated tunes. She turned the music up till he could feel the beat thumping through his chest and she started to sing along, practically bouncing in her seat as she danced as best she could while driving, singing with her beautiful voice.
"Hey!" she shouted over the lyrics, leaning in towards him while looking forward, only glancing towards him for a moment as she drove. "Come on, you must know the lyrics!"
He shook his head and blushed a little as she continued to sing, she prodded him in the side, sending an electric jolt up his side and causing him to squeak! "Sing!" she prompted again.
She started to sing, looking at him expectantly as they sat at a red light, her dark eyes deep and beautiful, hopeful. As the lights turned from red to green she glanced at him, looking a little disappointed as he remained stoically silent.
Jamie sighed and looked down a little. This was his day, and as bad as it had started it would only stay that way if he let it. He had an opportunity to change that, no point letting it slip through his fingers because of his embarrassment and anxieties. He raised his chin and joined her in song, which seemed to really perk her up.
They sang together for the rest of the journey, the loud music, her beautiful voice, her smile and happiness pulled Jamie from his worries. He no longer felt his fears weighing him down and he barely found himself thinking about Caitlyn. Just Kelly. He was out on a date with Kelly! Albeit as mutual girlfriends, but all the same he found himself genuinely smiling and looking forward to the day ahead.
As they pulled up outside the mall she turned the radio off and laughed breezily, grinning across to Jamie with adoration in her eyes. "Oh my god! You sing like an angel! You're eighteen now, you're definitely becoming one of the girls. We have a karaoke night every couple weeks, you would rock the joint!"
He blushed brightly and laughed too, he wasn't sure if she was kidding, and he wasn't sure if he wanted her to be. The idea of getting to hang out with Kelly as himself and not just occasionally bumping into her while she was with Caitlyn wasn't an unattractive prospect right now.
They climbed from the car and she locked it up with a click of her keys, walking across to him and taking him by the hand, she smiled encouragingly and squeezed it, looking down at him. "Be brave for me okay? You gotta be brave."
He wasn't sure what he hand to be brave about, this was just a dream come true for him. "I'll um. I'll try?"
The look of delight on her face was almost worth what he had endured so far since midnight. Almost.
She led him into the mall, joining the bustling crowds of people as they walked through together, hand in hand. He looked around, hope beyond hope that he might be spotted by some of his friends so he would have someone to witness that this date was really happening.
"Alright first things first." she stopped him in front of a fountain and stepped to the side, putting her fingers to her chin, tapping it as she eyed him over. "You have such beautiful blonde hair.. But it's a bit short.. You'd look a little dyke like.." She pursed her eyes and winked. "Not that there's anything wrong with that of course.. But come on, we can fix that!"
He blushed brightly at her comment, his mind trying to unravel her words and meaning but again he found himself swept away by her eagerness. They passed through the mall, chatting and relaxing, he found himself coming out of his shell a little and he had her almost always smiling and giggling.
He was so engrossed in the conversation that he didn't notice they had stepped into a store until she broke his reverie by waving down a member of staff. As he looked up he noticed, to his surprise that he had walked with Kelly into a hair Salon!
"Hey, Katie!" Kelly said with a smile to the approaching girl, a short brunette with a styled side shave. "Is Gemma about?"
"Mmhm! She's just on her break. If it's just your usual you're after I can help?" Katie replied with a smile.
Kelly laid her arm around the boy's shoulders and brought him closer, smiling as she presented him to Katie like a prize, causing him to blush as he looked at her, uncertain.
"She's having her first makeover, and you just know Gemma is the hair extension queen.." Kelly said in a conspiratorial tone.
"Oooh.." Katie said, smirking some as she eyed Jamie up and down as if seeing him in a new light. "Mm.. She's going to look divine. I'll tell Gemma you're here, take a seat?" she offered with a hand to a few spare waiting chairs, into which Kelly and Jamie sank.
He looked up to her, voice soft and cautious, "Make.. Makeover?"
"Of course! Our birthday present to you on this special day. Hair, clothes, makeup, nails, you know, makeover!" She winked.
"Oh.. Oooh.." Jamie sank back into his chair a little, feeling suddenly glum. Now it made sense. He had known there would be a catch, and here it was. He would be humiliated, made to look like a poor rendition of a girl for his sister's bemusement and worse, for her pleasure.
"Hey now.." Kelly's voice cut in on his dour thoughts, her fingers gently on his chin raising his head, frowning a little, looking at him with concern as she noticed his shift in expression. "You don't have to be afraid okay? I'm here with you and trust me, after this, you are going to look better than I do." she winked and smiled, then hesitated, before leaning in to kiss him on the lips.
An electric shiver raced through his body at her kiss, her full lips pressed against his own, soft and gentle, but with an intimac, he was unused to. He pressed forward slightly into the kiss, keen.
She leant back, breaking the kiss and leaving him wanting so much more. "Be brave, for me okay?.." she said, smiling, a glint in her dark gaze.
"..O-okay.." he stammered, swallowing.
"Hey girlfriend!" a voice came as a tall dark skinned woman with long immaculate braids stepped across to them both, meeting Kelly as she rose from her chair with a tight hug and a giggle. "Katie said you have something special for me?"
Kelly grinned excitedly and nodded, gesturing down towards the flushed and blushing Jamie whom Gemma eyed over curiously. "Hair extensions. She's enjoying her first day of being her if you catch my drift."
Gemma's eyes lit up and she pursed her lips before nodding, "Mm.. I follow you. I got you on this." she smirked and stepped towards one of the salon chairs, patting it and eying Jamie with a friendly, genuine smile.
Jamie looked up to Kelly who nodded reassuringly and ruffled his hair, "Go on sweetness. You're going to look simply amazing.
He returned the nod and made his way over to the chair, sinking down into it slowly and looked at himself in the mirror. "Isn't my hair a little short for hair extensions?.." he asked cautiously not looking for an out so much as genuinely believing his hair to be too short.
Gemma shook her head and ran her fingers through his blonde hair, measuring it with a keen eye, "Mm.. It only needs to be thirteen to sixteen centimetres, you'll do fine sweetness."
And so his fate was sealed. He sat back in the chair and watched as Gemma applied strands of what she called fusion extensions, though he wasn't sure entirely what that meant he was told it would help them last longer.
One set after the other he slowly watched himself transform. He had already been feminine, there was never any denying that, but the long blonde hair that began to adorn him was something new entirely. A few strands of blonde hair hung over his eyes as she worked, he raised a hand almost absentmindedly, brushing them behind one ear as she brushed at his new long hair.
"That turned out better than I thought it would.." Gemma said, self-satisfaction and pride filling her voice.
"Wow.. Gemma I know you're amazing but that's just stunning." Kelly interjected, her voice low but clearly pleased.
Jamie blushed as he looked at himself. He didn't so much look like a feminine boy any more than he did a boyish girl, a girl with a flat chest and a perchance for masculine clothes.
"I'm so jealous of her cheekbones.. She's just gorgeous isn't she?" Gemma again, smirking across to Kelly.
"She sure is. Mm! How much is that?.." she asked curiously, as Gemma led Kelly away towards the till leaving Jamie to stand as he stared at himself, tuning out of their conversation.
He hated to admit it, but he looked.. Cute.
Lost in his own reflection he looked up in surprise when he felt Kelly's hand on his arm, tugging him from the store. He glanced backwards, noticing Gemma giving him a friendly little wave as they departed. He turned his gaze back to Kelly. "W-where now?"
She looked at him and smiled broadly, "Further down the rabbit hole!"
He blinked at her, swallowing anxiously, but nodded all the same. He was already falling, part of him was curious to see just what would come of this.
Kelly by this point was almost brimming with excitement, all but dragging Jamie through the mall, making a beeline straight towards her target.
He stepped into a world of feminine outfits, a trendy clothes store with a perchance towards up to date fashion for women. He blushed as he looked around, knowing what was to come and in a way, resigned to it.
Kelly swept across the shop floor in a well-practised manner, she collected several items of clothing from hangers and shelves, draping them over Jamie's arms and giving him barely a chance to see what they were before new items were added or removed, deciding as she went, picking out the perfect outfit for him in her mind.
He found himself pushed forward towards the changing cubicles before he had a chance to realise what was happening, herded like cattle towards her goal. "Go! Go! I'll be right behind you!" she urged, patting him on the butt and smiling.
He stepped towards the cubicles, confused as he looked back at her, already she had flagged down a girl who smiled brightly at her, a 'Lucy' according to her name tag and started to talk with her, familiar.
He shook his head and stepped forward into the cubicle, leaving the door open for Kelly and laying the clothes out before him. Skirts? Leggings? Heels? What had he gotten himself into?
He had a few moments to consider the array of clothing before him and where he was before he heard the door click behind him. He turned to find Kelly there, standing with her back to the door, eyes glistening with excitement.
"Strip." She commanded, simply.
"W-what?" he stammered, swallowing as he backed himself against a knee high seat that ran the length of the side farthest from the door. From the seat to the ceiling stretched a mirror which he currently had to his back.
"Strip!" she repeated with a smile, moving to put the clothes up on a railing, "Come on we're girlfriends. There's no reason to be shy with each other anymore." Kelly urged.
Absentmindedly as he was thinking Jamie brushed a strand of long blonde hair back, tucking it behind his ear. Kelly couldn't help but smile as he so easily fell into feminine habits. This was a chance, a chance he had to take.
Finding a shred of bravery he spoke, "If there's no reason to be shy with each other ..You first?.." he asked, somewhat meekly.
Kelly blinked, a look of surprise passing across her features before she giggled. "Oh, I should've seen that coming, hm? You've been crushing on me since you first laid eyes on me.. Mm.." she paused, hands on hips. "Well, I did say that didn't I?"
Jamie nodded, keeping quiet as he sat on the small ledge, looking up at her hopefully.
"Well.. Sure, I suppose." she blushed some but smirked playfully.
She hooked her thumbs under the edge of her shirt and pulled it up and off over her head, revealing the smoothness of her hourglass form, her breasts held high in a black bra, her skin lacking the definition of muscles that Caitlyn possessed, but that only served to make her look more feminine, more beautiful than Caitlyn in his mind.
She leant forward a little bit, offering Jamie a view of her lush cleavage as she reached her hands behind her, fingering the clasps on her dark bra, pursing her lips as she struggled to unclasp it.
Jamie bit his lip as he watched, his heart fluttering in his chest as he watched her bra go loose, her hands running over her skin as she brought the straps over her shoulder and let it fall to the ground, her hands moving to her hips, her breasts on full display to him, one perfect eyebrow raised.
Jamie stared at her, eyes wide like a deer caught in the headlights, her breasts were full and heavy, their shape naturally curved.
"Ever seen a real pair before?" she asked demurely, sauntering forward, leaning over slightly so they hung enticingly just before his gaze.
Jamie blinked and shook his head looking up at her. "N-no.. Just on the internet." he lied, not wanting to recount his adventures that morning in the shower with Caitlyn, while it had been his first real experience, he would want to remember this one as his first.
Kelly placed her hand on the mirror behind him, her lips by his ear as she spoke, "They're so much better than online aren't they?" she spoke softly, her voice soothing as she bent over, giving him a view he had fantasised about so many times before.
Tentatively he reached up a hand but found his fingers laced with hers as she moved to hold it. "Mm. You can feel them and help me out of my jeans.. Just as soon as you've gotten changed."
Jamie looked up at her again, her hopeful face, beautiful and kind. He nodded. Eager. He'd have worn anything to see her in all her glory, to touch her was a bonus he'd dreamed of a thousand times but never thought would become a reality.
"Good.. Now.. Strip, please?" She said, standing once more and turning her sleek back to him, not with the intention of providing him with any modesty but so she could start going through the assortment of clothes she had picked out for him.
Blushing he started to strip his clothes off, placing his coat and shoes in a corner before adding his shirt, pants and socks to the heap. Before long he was stood in just his underwear, which, after some prompting from Kelly, he removed too. It was only after that that she started to hand him clothes, her eyes drinking him in.
First, she passed him some dark black leggings which she showed him how to put on correctly, he bit his lip as he rolled the soft fabric up to his thighs where they stopped with a lacy band.
Next, she passed a tight blouse, black and white with vertical stripes, it had a low neckline that would've shown off any cleavage, had he had any, as well as being quite revealing in that it relied on the sleeves and tightness to hold it on, having no shoulder straps.
She followed that up with a knee length black skirt that flared outwards some at the hem and a pair of cute, low-heeled shoes with straps that fastened over the open top. All in all the effect was incredibly feminine, stylish and a bizarrely good fit.
Before he had time to process his new look Kelly was standing over him, makeup kit in hand. She applied foundation, eyeliner and mascara with deft, practised movements. She pursed her lips as she dabbed at his full plush lips with her red tube of lipstick. She had decided not to apply any blush of her own from her makeup kit as Jamie seemed to be flushed with colour enough as it was.
She bit her own lip softly, eying her result and tucked her makeup kit away, nodding keenly. "Yeah.. Yeah, wow.. That's your look.. You look.." she paused, putting her hands on his shoulders and turning him around slowly to face the mirror. "Well.. Just look for yourself."
And he did, turning his heart skipped a beat. There was no doubt as to what he saw. A busty brunette, topless and smirking, standing just behind and off to the side of a slender, gorgeous girl, which had to be him. His outfit cute, stylish and girly, the top clinging to his slim chest. While that served to highlight his obvious flat chest, the full effect was disarmingly feminine. The skirt hung down to his knees, his thigh-high leggings extending down beyond that to his modest heels.
He looked like a college girl, long blonde hair, complementary but not overpowering makeup, kinda showy but not kinda slutty clothing, well, besides from that fact that under his skirt above his dark thigh-highs there was nothing but breeze.
"Well?.." she prodded him, curious as to what he was thinking as he stared at himself.
"I… I look so.. Girly." he said, at a loss for words, his voice soft and uncertain. He'd always maintained that this wasn't him, just a charade to placate Kelly and in turn, Caitlyn. But he looked so natural in his femininity.
Kelly giggled a little and squeezed his shoulders. "I knew you'd look gorgeous but gods.. It suits you so well. You're a perfect little sweetie!" she smiled and turned him back around to face her. "So er.. I guess I owe you the second half of my bargain. Wanna sit down and help me with my pants?.."
He blushed some and let himself be guided down to a sitting position, his face around about at the height of her crotch. He nodded some, he had been so engulfed in the vision of himself he'd forgotten about her promised reward for his good behaviour.
After setting him down she moved her hands to her curved hips and eyed him expectantly, waiting for him to make the move Kelly and she knew Jamie, was waiting for.
Determined not to let this opportunity slip through his fingers he raised them to the front of her tight jeans, his small delicate fingers easily unbuttoning the front, the only sound for a moment the slow run of a zip as he unzipped them. He could see from the smooth skin of her pelvis showing that she too, wasn't wearing any underwear.
He felt himself blush as he ran his hands across her thighs to her waist, fingertips hooking under the edges of her jeans and started to pull them down across her smooth skin.
His heart pounded in his chest, he'd dreamed about this so much.. Fantasised about it.. Desired it above all else. And here she was. Before him. In all her… ...Glory.
"Surprise?.." She giggled a little anxiously as her soft, hefty member was revealed to him, falling free from the tight prison of her jeans to hang between her thighs, her jeans falling to the floor to lay in a bundle around her feet.
She tilted her head and bopped him on the nose with a finger, "Sweety? I know it must be a big surprise… Finding out I'm just like you.. But we're girlfriends? No sense in hiding it?"
Just like me, he thought as he stared at it. Then up at her, fear and worry in his eyes, it started to make sense. This was all just a ploy, to get him looking like a girl so she could fuck him. He half expected Caitlyn to walk into the stall at any moment, laughing.
To his surprise, Kelly just looked just as worried, even ashamed. Embarrassed? Humiliated? What? Her hands moved to gather up her jeans, which she started to work back up her legs.
"W-what are you doing?.." he asked, voice soft and shaky, expressing the confusion that dominated him.
"You hate it! You hate it and you hate me." she said, her voice sounded as weak as his own, as if she were on the verge of tears, tugging her jeans up over her knees.
"What? W-what no!" he said awash with guilt, she'd revealed a secret to him and he'd looked at it in horror, he could only imagine what she was thinking, this girl whom he had crushed on for so long had revealed herself to him and he had looked at her like he looked at Caitlyn.
"N-no?.." she asked, looking at him again, soft and watery eyed, jeans around her thighs, just below her soft member. "You dont.. You don't hate me?.."
He shook his head. "N-no! Of course not! I just.. I just thought you were going to… Going to." he looked down and bit his lip, going silent.
She pursed her own lips, speaking softly now, "Going to what?.. Hurt you?.. With this?"
He simply nodded. Hands clasped in his lap and shoulders hunched he looked so small and vulnerable.
"Oh, gorgeous… We're girlfriends! Remember? I'd never hurt you." she smiled gently and let her jeans fall to the floor. "Let me guess. You had a run in with Caitlyn.. Didn't you?.."
He looked up at her sharply. "You know about her.. Her thing?"
She laughed a little and moved to sit beside him on the small chair, forcing him to scoot up so she would fit. "Well duh.. A fitness freak like her and a girl like me? What did you think we had in common.." she paused and slid a hand gently around his waist, holding him comfortingly, "Well.. Asides from a mutual attraction for you I mean.."
He flushed with colour, looking up at her still as she sat beside him, feeling the reassuring presence of her arm around his waist. "You.. Think I'm attractive?.." he asked, meek and confused.
"More than you know.. This morning when I saw you walk in I thought I'd died and gone to heaven.. A whole day with you! Can you believe that?" she said, practically echoing his own thoughts about her. "But now that I see you like this.. How mistaken I was.. If that was heaven then, now you're a whole choir of angels.." she bit her lip as she eyed Jamie over and he couldn't help but notice her cock throb, swelling slightly as she eyed him.
He looked up to her, his anxiety written across her face.
"Gods.. Caitlyn must really have done a number on you? You're not the first little doll she's turned out.." voice sounding anguished for a moment, "But it's nothing to be afraid of. Girls like us really should stick together, you know?" she said, voice soothing now, a hand giving him a light squeeze.
He sighed a little and looked away from her. Had Caitlyn put her through the same stuff as she was putting him through? As much as he feared Caitlyn he couldn't lie to Kelly, not here and now.. "Kelly.. I'm not.. I'm not a girl like you.. I'm not even a girl. That's just her plan. If I don't behave today and do as you tell me, she'll hurt me worse tonight.. I know she will. I'm not a girl.."
"Aw hun.." she said softly, raising her hand to his chin, turning his face up towards her. "Of course you are.."
He looked a little taken aback, his lips parting about to protest but she cut him off, "Look at you! You're absolutely gorgeous. I'm genuinely jealous of how cute you look.." She smirked slightly, teasing, "And you take it so naturally, did you notice you were swaying your hips a little after you got your hair done?.. And I saw how you looked at yourself in the mirror. You're loving this! You were born to be a girl."
"N-no.. I mean.. I can't.. I mean.. Ah.." he floundered for words as she teased her fingers over his waist through the soft fabric of his top. "That doesn't mean anything.. It certainly doesn't mean I like.. I like that sort of thing.." he said with a dismissive wave towards her tool, now semi hard between her thighs.
"No?.. How would you know if you've never tried?.." She asked.
"You know I've tried it.. Cait-"
"Ah!" she cut him off again, "I bet she fucked you like she would jerk off with her hand. I bet you've never been made love to before by a girl like me.. Hardly the same thing.."
He swallowed. As a matter of fact, he'd never made love to anyone, let alone a girl like her. "Well, no.. But-"
"Then you don't know that you won't like it do you?.."
He pursed his lips, annoyed at the constant interruptions. He opened his mouth to speak, but she beat him to it again.
"How about we make a sort of bet," she said, smiling then. "Let me do whatever I want with you.. And if at any point you want me to stop.. Say stop. If you say stop, I'll let you fuck me.." She winked playfully.
He flushed brightly at that, "W-what would you win?.." He asked, a stupid question he knew, but it was better than just sitting there with his mouth agape.
She giggled a little and nudged him playfully, "If you don't say stop, trust me, we'll both win a prize better than anything else.."
"S-so.. All I have to do. Is say stop. And I can fuck you? Actually, fuck you?.." he asked, his eyes going wide.
"Yup!" she said cheerily, then pouted cutely, "Though I'll be very very upset if you say stop without actually wanting me to.. Just.. Give me a chance, alright?.. I want to make you feel good. Really good."
He frowned a little as he thought. This wasn't like with Caitlyn at all. Worst case scenario, he fucked his crush. Actually, fuck her! Whether she had a dick or not, that wasn't a chance he could pass up, his eyes trailing over her nude, feminine form, her full breasts, her smooth skin. He could fuck Kelly. That one thought ran through his mind, again and again, erasing any suspicions.
"...Fine.. I'll give you a chance.." he said, he wanted to trust her, wanted to have someone in his life at the minute that didn't want to see him hurt.
She let out a delighted little squeak and leant down, kissing him quickly before standing and beckoning for him to stand too.
"Up! And turn around, face the mirror.. Just kneel right there on the edge.. Here.." She scooped up his old clothes, rolling them and placing them on the wooden bench to give him something soft to kneel on.
He followed her directions, a part of him just wanting to scream stop and have her fulfil her bargain. But that sounded like something Caitlyn would do, dishonest and deceiving. And he didn't want to disappoint Kelly, she seemed so invested in actually making him feel good.
He knelt on the edge of the chair, his hands placed against the mirror and his back arched, a blush on his cheeks as he all but realised he was presenting himself to her.
He felt her fingertips sliding up the leggings-clad smoothness of his thighs, under his skirt, flipping it up over his bare rear. With his knees spread as they were, he felt a sudden chill, she could see-
"Oh! Not hating his as much as you thought you were, hm?" Kelly giggled as she moved her hand down between his thighs, her soft fingers wrapping around his hard cock, pointed downwards, throbbing eagerly in her grasp, noting how he arched his back for her, like a girl in heat.
"A-ah! W-what do you expect… You're naked.." He protested weakly, trying to defend himself though even he knew that wasn't the only source of his arousal.
"Mmhm sure sweety.." she smirked and bit her lip, soft hand slowly jerking his cock, slow gentle motions, working him up so he would be more pliable with what was to follow.
As she moved her hand over his cock she glanced down, noting her phone poking out from her jeans pocket on the floor, biting her lip she squeezed and stroked his cock, eliciting a little whimper from the boy who closed his eyes briefly. Moving carefully knelt down behind him and grabbed her phone. Behind him, like she was, even with the mirror he couldn't see her hand below the edge of the chair. She had a text.
"Hows it going? Get your dick wet yet? C x"
"Looks gorj, bout 2 fuck, so ez! Thx 4 his sizes, prfct fit! K x"
She set her phone down and smirked happily, leaning in to kiss his full ass cheeks, soft little angel kisses, making him writhe back for more. It was just all oh so easy! Forget about asking for it, Caitlyn's brother was practically begging for it. She couldn't wait to see what else Caitlyn had planned for him, but so long as Kelly was counted in she was happy. This was heaven.
"Still okay?.." She asked, sounding demure and anxious as if she was afraid that he would say stop at any second. Though part of her, the painfully erect, eager part between her thighs almost hoped for that. Then she could drop this charade and have her fun. But she had to play her part, act the cautious curious lover, all affection and concern.
"S-still okay.." he moaned back a little breathy, a drop of pre forming at the tip of his cock which she massaged into the soft skin of his firm shaft.
"Good.." she purred softly, feigning relief. Though if she had her way it would probably be the last time she touched his dick. As often as she been on the receiving end of Caitlyn's thick cock she doubted she would have much to do with Jamie's. He wasn't exactly the pushy forceful type, which is what it took to make a girl like Kelly put out.
She kissed along his full soft ass cheeks, enjoying the sensation of his warm pliable flesh pressing against her lips and face. Moaning softly, eager and keen, fingers still gently massaging his cock she squirmed her face between his cheeks and let her nimble, experienced tongue lap out over his little star.
"A-ah!" He gasped in shock and surprise, leaning forward a little away from her, but her hand on his cock guided him back into place. "O-oh gods.. Kelly.. Kelly that feels.. Feels good.." he said, shame resonating through his voice, mingling with the pleasure in it.
Kelly rolled her eyes, it better have felt good. Lord knew she'd had enough practice over the last couple years on his dominate, high libido, strong willed and strong bodied sister. She rolled her tongue skillfully between his plush cheeks, teasing around his hole in slow sweeping circles, matching the pace to the slow twisting motion of her hand as it glided up and down his manhood.
As Kelly had planned, as she rimmed his cute little girly butt and stroked his soon to be seldom touched cock Jamie, with his hands pressed against the mirror had nothing much to look at besides himself. He stared into his own eyes, so foreign and strange, masked with pleasure and lined with makeup, he looked unrecognisable, he looked gorgeous. He looked like so many starlets he'd watched in porns, faces a shine of lust and desire. With his mind flooded with what she was doing to him, he could see just how much he really looked the part.
He squeezed down as she pressed her tongue forward firmly, feeling her soft tongue work into the hot embrace of his ass, working it around in rhythm with her fingers. Her other hand pressed and squeezed his ass, cupping and groping the tempting flesh, each little motion causing him to fall further and further into her desires, making the word stop seem oh so far away from him.
She moved her hand towards the crack of his delicious cheeks, one of her slender fingers gently probing at him as she kissed and licked at him, spearing him with her tongue, he writhed back, eager like the slut he still denied to being.
She withdrew her tongue and replaced it in one swift movement with her finger. He tensed, gasping and curling his toes in his heels, eyes going wide, "A-ah! St-"
She interrupted him quickly, her tongue running smoothly across the sack of his nuts, bathing them with her tongue as she squeezed his cock and worked the finger slowly but firmly in and out of his little ass, a new wave of fresh sensations causing his word to falter into a gasp! She had to be careful, that had been close.
He stared at himself, his flushed cheeks, his half-lidded expression of pleasure and lust, he'd never been touched like this before, and by Kelly no less, butt play wasn't exactly what he wanted, but it just felt so fucking good, he couldn't help himself but let out a soft girlish moan.
Kelly worked him in a slow building rhythm, hand around his cock, finger working his sweet little hole, tongue worshipping his smooth balls, stroking, licking, pushing, pulling, primal. She felt her own resistances begin to crumble and began to wonder instead how Caitlyn had waited so long before enacting her plans.
She bit her lip, staring at her finger disappearing between his cheeks, feeling the tight hotness of his ring around her finger, the enticing softness of his pillowy cheeks.
She released his cock and stood up, half breathless from her efforts and from her own lust. She ran both her hands over his smooth pale butt and squeezed, her thick cock landing squarely between his cheeks, gliding it between them and feeling him pleasure her for the first time.
"A-ah.. What?.." he started, breaking from his reverie.
"Shh.. Trust me.. I'll make you cum.. I promise.. I promise okay? Just trust me.." she pleaded, just needing to get in on the heat and intensity of the scene, leaning down to spit on his ass and on the tip of her cock, rubbing it up and down.
"B-but.. I'm not.." he started to stand up too but felt one of her hands settle on his back.
"Don't think, just feel.." She insisted, gripping his hip with one hand, the other gripping her cock on the middle, guiding the tip, lining it up, pushing forward..
He gasped, making eye contact with himself, watching the play of feelings across his face. He wanted to hate it, wanted to say stop, wanted to shove her off, but he couldn't deny what he saw, the face in front of him was one of a beautiful, gorgeous woman driven to lust and loving every second. How could he deny that visage the pleasure it was so clearly receiving?
"G-good girl.." she panted as the thick tip of her cock popped into his hole. He might not have been a virgin thanks to his sister, greedy bitch, but that just made this easier, that and given his initial fear she doubted he'd ever been fucked with lube before, even if it was just spit, it made the world of difference.
With her cock lodged firmly inside him she moved both her hands now to grip his hips, she wanted to say so many reassuring things to keep him placated, but he seemed to be lost in a trance with himself, she didn't want to break that for fear of his realising the situation he was in.
Jamie felt her push forward, for the second time in his life felt a cock push inside his ass, using him for pleasure, but this was different. This felt good. He felt as she sank inch after inch, slow and cautious into him, felt it expand and fill him, felt himself squeeze and hold her, eliciting a moan from her.
He stared at himself in the mirror. This time yesterday he had been Jamie, the slightly girly guy with a sister who doubled as his best friend. He'd had girlfriends sure, but he'd never gotten anywhere with them. That Jamie was less than twenty-four hours ago. Now he was being fucked for the second time. Wearing makeup, feminine clothes and hair extensions, he looked hot. To top it all off the girl currently exploring him was the girl of his dreams Kelly, the curvy brunette who had been the focus of so many of his late nights and early showers.
She stared down at him, eyes fixed on her thick cock sliding between his cheeks, delving deep into him, she didn't stop, couldn't stop, pushing her hips forward and pulling him back until every inch of her cock was buried deep inside him, surrounded and encapsulated by his ass, the pleasure pulsing through her body so extreme, enhanced by the mental dominance. She was the boss of this sweet little sluts ass. And he was getting off on her cock, that much was written across his face as clear as day and that alone almost made her cum then and there.
She pulled back and pushed forward, not shy to start off with a not so slow rhythm, they both needed this now, the more she gave to him the less he could find the room in his thoughts to question what he was doing, to hate himself, to wonder what he'd gotten himself into.
The small stall echoed with the sounds of their lovemaking, her pelvis slapping into his cheeks, his whole body rocking backwards and forwards, his panting little moans, her whimpers of pleasure through gritted teeth, part of her worried that even with having the two stalls either side of her locked by Lucy that people the next stall over would overhear them, but she couldn't care less.
She urged him down slightly and arched up on her toes, so her thrusts angled down into his body, positioning her cock so it would rub against him in a very specific way, she bit her lip as she looked down at him, as much as her own pleasure was her goal, she wanted, if she could, to keep her promise and make him shoot.
He moved as she directed him, parting his legs further to lower himself, not understanding why she was changing position when it had felt so good. This thought lasted until she pushed into him again, fireworks going off in his mind as a whole new pleasure lanced through him. He felt weak and in an instant, Kelly found herself all but holding him up as she fucked him. She might not have been as strong as Caitlyn but this boy toy was a waif, and she knew how to pound a prostate.
She fucked him hard, his head starting to loll from the constant assault, soft painted lips parted, electric jolts of pleasure ravaging his body, her beat was constant and relentless, he wanted to move his hand down and touch himself, but his arms were weak, he needed them to hold himself up. He started to push himself back against her, wanting more, wanting it harder, wanting the pleasure to never end.
Kelly raised a hand to move a few strands of hair that had fallen in front of her face asides, feeling herself drawing closer, every movement threatening to push her past the point of no return, she let out a gasp! He wasn't.. Was he? He was! She stared intently down at him, the little slut was pushing back against her, she bit her lip and slowed a little, watching as he picked up his pace to keep the beat steady.
Jamie closed his eyes, vision was useless to him now, only the pleasure coursing through his body mattered. His body moved on its own, keeping the pace up, pumping her cock in and out of him. He'd been wrong about her, wrong about this, she wasn't fucking him for her pleasure, using him, no, he was using her for his pleasure. He felt her bend down over him, breasts pressed into his back heard her groan as she stretched, then stood back up, but didn't think about it, didn't care about anything other than the sensations powering inside of him.
Kelly stood again, panting and whimpering, one hand on his hip as she stood as still as she could, her other hand again holding her smartphone, this time as she recorded the whole thing, her not moving, him bouncing on her cock like the trained little slut he was becoming. She couldn't believe it, even in her wildest dreams she'd never have thought he'd have come this far so quickly, he really was born for it. She wanted to send this video to Caitlyn, to show off and make her jealous, but this was just for her, her personal collection and maybe her personal blackmail. She made sure to catch his face in the mirror, the pleasure, the lust, but still Jamie, that could be useful.
There was no warning for Jamie, he didn't know what he was feeling, what to expect, what was coming, this was new territory to him. One second he was lost in a mind of bliss as a hard throbbing cock bounced in and out of his delicious tight ass, the next his cock stiffened between his thighs, his mind going white.
His cock pulsed, hot cum shooting out to stain his old clothes that he kneeled on, gasping and moaning out loud and girlish, whimpering, the sudden influx of sensations was soon met by a familiar one, the steely hardening and liquid heat spreading deep inside his ass, Kelly was cumming inside of him, he had made Kelly cum! That alone drove his pleasure to new heights, there and then he didn't care that he'd made her cock cum with his ass, all he knew was that he had given the girl of his dreams pleasure equaling perhaps his own.
She whimpered, struggling to hold her phone steady as she felt the boy cum under her, his ass gripping and squeezing, milking her cock so incredibly good she couldn't believe it, the pleasure engulfing her cock and the lewdness of what he had done and the noises he was making were enough to force her to join him in a single wonderful climax, his body grinding back against her, keeping her hilted as she drained herself deep within him, filling him, claiming him. She could begin to see herself fighting Caitlyn for possession of him, with an ass like that there was no way she would remain a pawn in her games. She wanted this all for herself.
Her cum pulsed in jets into him, painting him white from the inside as his cock dribbled the last of it's much smaller load onto his clothes, ruining them and ensuring he would be walking out dressed as he was.
Still hard inside him she blinked, looking down at him in surprise, he was still pushing backwards and forwards gently, milking every last drop of pleasure from the both of them, she let out a gasping laugh, breathless as she patted him on the ass. "S-stop.. You win.. I give in.." Kelly said with a grin.
He looked over his shoulder at her, panting softly and laughed a little too, soft, feminine, exhausted. He was in such a euphoric state he didn't even notice as she dropped her phone onto her jeans.
Fuck, that just wasn't fair. Even after all that he still looked gorgeous, his makeup still in place, his hair framing his face perfectly. She looked up at herself in the mirror, hair a mess, face shiny and flushed. He looked like he could go for hours and still come out looking pristine.
She started to pull herself slowly from him, eliciting a sigh of pleasure from the boy as her cock popped free, semi-hard, a thin line of cum joining them still as they tried to recover.
"I think.. I think we were… Too loud.." Jamie said, smiling softly.
"N-nah.. Lucy.. Lucy said she would cover us.. But.. But you might owe her a blowjob.. Gemma too.." she said teasingly, smirking softly as her hand caressed over his booty, squeezing it possessively, he still had his back arched for her, showing off.
Gods, was everyone a dickgirl? He didn't even know if she was kidding. He looked down at his old clothes, like his old life, stained with his cum, his cock flagging as he swallowed softly. His mind was a haze of confusion as he again looked at himself in the mirror. Was this look forced upon him a lie? Or had his old life been a lie? Who, or what, was he? Given how much had happened in the last twelve hours alone. He knew in the next few days he would learn who he really was.
Kelly saw the expression on his face, the thoughts sinking in and stood him up on unsteady feet, turning him around slowly and biting her lip. She leant down then to kiss him, pushing her tongue into his mouth, dominating him as she pushed him gently against the wall, her hand running through his long blonde hair, all thoughts were forgotten as he raised his hand to cup and squeeze eagerly at her breast. She wouldn't allow him to regret what he had done. Not if she was going to persuade him to be her girlfriend for real. Caitlyn be damned.
New Horizons
Jamie looked down at his shoes concentrating, they were new, like the rest of his outfit that he now wore, new and unfamiliar, but somehow comfortable, like the whole facade he was now displaying to the world. The slight heels on them demanding focus on walking to save himself from any danger of falling, or twisting his ankle. His old clothes, like his old life, lay discarded back in the changing room, stained with his own cum, his own admission.
He walked alongside Kelly, making his way through rows of clothes wearing his own new style, though they fit him so naturally, Kelly could've sworn he'd been wearing them his entire life.
Meeting with Lucy at the tills she priced the items and they set about removing the tags, Lucy's eyes, wide with curiosity and excitement were drawn to Kelly, despite the immediate attraction of Jamie.
After Kelly had paid she had excused herself rather swiftly, leaving Jamie in Lucy's temporary care, much to Lucy's obvious bemusement. Kelly, bless her, looked a mess. Her makeup was smudged, her hair wouldn't stay straight and her entire outfit looked a little disheveled. She would need to 'freshen up' as she had said, though still seemed perturbed with just how pristine Jamie looked, even with an ass full of her cum he just looked so naturally beautiful, a picture of innocence.
Lucy, obviously taken with curiosity vanished only briefly to speak to her manager, managing to clock out of work early and join Jamie in waiting outside the shop. He still, embarrassed, looked at his new shoes. While he wasn't ashamed of what he had done with Kelly, it had felt so good, he wasn't sure how he felt with Lucy knowing. While he had only known Kelly from a distance, Lucy was a complete stranger to him.
She ushered him to a bench and sat besides him silently, smiling gently, eying him over. He, in turn, looked up at her, a blush on his cheeks. He hadn't paid her much heed before, so swept up in Kelly's rush to get him inside a cubicle his only thoughts had been in the then and there. She was cute, youthful, slender and lithe, quite pale skin, strawberry blonde hair cut short with light green eyes and a smattering of freckles.
"Trying to count them?.." she asked, smirking slightly, her general outlook seemingly innocent but her eyes swam with mischievousness.
He started a little and looked at her uncertainly, "Ex.. Excuse me?.."
"My freckles. You were sorta staring. I figured you were trying to count them." She explained, her smile deepening.
He blushed slightly and shook his head, looking down. "I just sort of spaced out.. Sorry.."
She laughed a little. "Cute. So uh.. How do you know Kelly?"
"She's my…" he hesitated, remembering Caitlyn briefly and quelling those thoughts from his head. "My best friend."
Lucy pursed her lips and clasped her hands together, looking towards the mall's bathrooms where Kelly was likely fixing herself up. "Nah you see, I'm her best friend.. Me and Gems anyway. She never mentioned you before?"
Jamie frowned. That stung a little, had he meant nothing to her before today? Thinking back that honestly wouldn't surprise him, after all he was the younger brother of her, he thought, lover Caitlyn. He sighed a little. "She's just a friend.." he said unsure even of that now. What was he to Kelly?
"Mm.. Lover more like." She replied with a wink. "Or girlfriend? I wish I was that lucky. She always gets the cute ones."
He looked at her, looking and recognizing the desire in her eyes, an expression that was becoming all too familiar and felt himself blush slightly. It was weird, having a girl checking him out like that.
He shrugged a little, feeling embarrassed.
"You're not used to people checking you out are you?"
He looked up at her and shook his head a little, "Sorry this is.. This is all sort of new."
She chuckled a little and waved a hand vaguely out towards the streams of people walking past, going here and there throughout the mall and passing the bench they were seated on. "Look see, half the guys walking past are checking you out."
He looked up, having never considered that, the people passing seemed regular and normal enough, but Lucy was correct. Where the women would glance at her casually, taking in her dress, makeup, style then looking away, the looks from many of the men would linger, trailing up and down her figure, drinking her in before walking past. Some even glancing back over their shoulder to steal another glance at him before moving away.
He felt his cheeks flush brighter at that realization. It was odd enough being eye candy for Lucy to enjoy, but everyone else too?
It only took a few minutes longer before Kelly walked from the bathroom, appearing refreshed and seeming more herself. She smiled as she spotted Lucy and Jamie, making her way towards the two of them.
"Hey! Hope she's looking after you hm?" Kelly asked with a smirk, glancing between them with an amused suspicion, seeing the embarrassment shadowing Jamie's face.
Lucy grinned cheekily and nodded. "Yuh huh. I just pointed out to her how many boys were looking her way." she winked.
Kelly rolled her eyes and laughed too, "Pfff, don't worry about them, you're with us, we'll.." she glanced at Lucy and smirked herself, "We'll look after you.."
Jamie nodded a little and made himself smile a little. It did make him feel better, to be with these two, safety in numbers. He sat up a little straighter and tucked his hair behind his ears, looking between them as they watched him, he broke the silence, "Alright.. So, what now?"
Kelly beamed brightly and didn't so much as hesitate, "Nails!"
Lucy cooed and clapped her hands together standing up, "Usual place?"
Kelly nodded and took Jamie's hand, pulling him to his feet but holding onto his hand all the same.
Lucy nodded, "I'll catch up with you two, I'll go grab Gemma, get the squad together!"
Jamie watched as Lucy walked away, trying to figure her out and all together failing. He looked up to Kelly and found her looking at him with a smile.
"You're so fucking beautiful Jamie.. And that was just.. That was just amazing.. I think I want to keep you all for myself.."
Jamie felt a pang of both amazement and fear at the thought of that. "I.. I would love that.. But.." he trailed off, looking down as Kelly tugged him into walking along side her.
"But Caitlyn, yeah. Don't worry about her too much. I'll try and figure something out." She pursed her lips in thought then looked at him, tilting her head some, "So what did you think of Lucy?.."
"She seems nice, I suppose?" he answered somewhat meekly.
Kelly grinned. "Glad you think so. You owe her a blowjob after all. For watching out for us."
"I.. I thought you were kidding when you said that?" Jamie asked, conflicted. Hadn't she just said he was all hers?
"Mm I thought about denying her you, but that just doesn't seem fair." she shrugged a little, continuing to lead him through the mall.
"But.. I'm all yours? Just yours?"
She smirked playfully. "Well yeah.. But you're one of the girls now. You've got to look out for your girls?"
He looked up at her with worried eyes, this beautiful dark haired vixen that had shown him a new side to himself he didn't know existed was sounding a lot like Caitlyn in her eagerness to pass him around.
Kelly smiled reassuringly, "Hey, don't worry? I'll look after and take care of you. You'll love what you do when you're with me. Just be my good little girl and I promise you'll enjoy every second."
Jamie just nodded a little, unsure how else to respond. He knew it had been too good to be true, him being hers and hers alone. But still, Caitlyn, his own sister had been cruel, he had to do what she said or be hurt. Kelly, his crush, still made sure he did what she told him to, but with the prospect of rewards.
He had the choice between the carrot and the stick, and while he'd prefer not to be the packhorse in either scenario, having to choose between the two wasn't such a hard decision to make. He walked a little closer to Kelly, squeezing her hand.
She smiled and nodded happily, taking his squeeze as a sign that he was okay with the everything, for now at least.
She led him through the mall stopping at a juice bar to get back some much needed bodily fluids. She ordered for the both of them, ordering them the same thing. She paid and handed him his cup, winking playfully as she took a sip, beckoning for him as she started to walk again.
He eyed his drink curiously, a warm yellowish color and took a sip. Pineapple. He blushed and looked up at Kelly.
"For later!" she laughed, grinning broadly.
They arrived together outside the nail salon having finished their drinks and found Lucy and Gemma waiting, talking casually. Lucy spotted them first and raised her hand smiling.
Gemma smiled in greeting, placing her hands on her hips and eying Jamie over. She had been the one to do his hair, but his outfit would be new to her and it seemed well received.
"Damn she's gorgeous.. You did a good job." Gemma observed in her usual reserved manner, nudging Kelly as they moved to stand in a circle.
Lucy scoffed and folded her arms under her breasts. "Yeah, that's not all she did a good job on."
Gemma shifted her gaze from Lucy to Kelly, raising an eyebrow. "Ooh?"
Kelly looked up at the ceiling, innocently.
"Railed him in one of my changing rooms." Lucy filled in helpfully.
Gemma looked to Jamie and raised her eyebrows together! "Oooh?"
He blushed and looked down shyly.
"Well couldn't have hated it, she's still here." Gemma patted him on the arm. "Wasn't so bad huh?"
He blushed and chewed his lip, "Well.. Um.."
"She came like a girl." Kelly said proudly, interrupting Jamie.
Gemma and Lucy both seemed surprised, looking to Jamie as if seeing him in a new light.
"No way? For real? Without being touched?" Lucy asked.
Jamie swallowed and simply nodded, feeling the embarrassment wash over him.
"Oh my god that's so fucking hot." Lucy said eying him up and down, "Where have you been hiding this treasure, Kelly?"
She tapped her nose and shrugged! "Secret!"
Lucy pouted at her and seemed curious still, though the not knowing was clearing bugging them both some, through they seemed content to just enjoy their time with him, for now at least.
"Aw don't look so upset.. Today's on me! After we get our nails done I was thinking we take in a film? My treat?" Kelly said, her arms open wide in a peace offering.
Gemma still seemed a little skeptical but nodded amicably, Lucy seemed far more excited at the idea of a freebie.
Jamie as before didn't get a say in things. Before he could so much as muster the courage to voice his thoughts he was pulled inside the salon, flanked by Kelly and Gemma, Lucy off to the side of Kelly probing her for more information about him, though she was evading her questions masterfully.
As they talked, gossiped and generally made conversation Jamie was sat down opposite a woman, young and pretty she had long black hair which she kept tied back and her features were delicately Asian, she smiled beautifully and he had a sinking feeling in his chest.
He looked to Kelly sitting in the next seat along, her own nails been tended and hesitated, watching her. She looked to him, briefly glancing at his nail expert then back to him, smiling before turning back to her own.
He let out a sigh of relief. This wasn't one of her girls, another such potential woman packing heat.
"Um.. Hi?" he ventured to her, utilizing his disarmingly attractive smile.
"Hi!" she replied, a smirk on her delicate features, "First time?" she asked, holding her hands to his, her own smile warm and genuine.
He nodded and placed his hands in her own, unsure but not afraid or anxious. "Um.. Yes. I'm getting a bit of a makeover, her idea.." he nodded to Kelly who grinned back.
"Yeah, she was a bit stuck in her ways.. New hair, new dress, new nails." Kelly explained to the young woman who nodded along, turning Jamie's hands over in her own.
"Her nails are beautifully looked after, and such soft hands! I wish I had hands like yours." she laughed playfully as she placed his hands down and got her equipment.
Kelly pursed her lip and shot Jamie a jealous look. It wasn't fair how much better he was at being a girl than she was. But at least he was hers to do with as she pleased. Almost.
"Just give him some extensions and paint them red, match the lipstick." she instructed, a little to the point. The young woman looked to Jamie for his approval and he gave a resigned nod.
"Sounds good!" the young woman said as she got to work.
It wasn't at all like he expected. Shy as he was he wasn't much for joining in on the conversational threeway that was Kelly Gemma and Lucy. Instead, he was off in his own little world with this woman, Jin, according to her name tag.
He had done many lewd and crude things for the first time in the last day, but this was a much gentler experience. This girl's expert hands caressed over his own as she worked, gently holding, guiding turning and inspecting. It felt nice and he couldn't deny she was a cute girl.
He looked from her to the other experts, they were all seeing to the giggling girls with a warm professionalism. It seemed to Jamie that Jin's touch was lingering more than theirs. He looked to his hands then up at her her. She was looking at him. She winked.
He blushed brightly and hesitated, he wanted to look down, look away, withdraw shyly. But instead, he smiled just a little brighter and held her gaze.
After a moment had passed between them Jin glanced away towards Kelly, then down, innocently once more towards Jamie's nails.
He looked across to Kelly to find him eying him, with a mounting suspicion.
Jamie smiled brighter at her too, then winked.
It was Kelly's turn to blush, her concerns washing away as she laughed, utterly disarmed by his charms.
With Jin concentrating and carefully painting his nails and the three girls lost in their own little conversation Jamie had a moment to think about everything that had transpired to him in the mall today. He had changed, in more ways than one.
Physically he had been altered virtually beyond recognition, but he knew he could undo all of that within half an hour. What concerned him were the other changes. He was acting like a girl, talking like one, walking like one. And now even, he was using his beauty to his advantage, disarming Kelly with just a wink.
It was with a sudden realization that Jamie realized what he was. He was a hot chick. He thought about all the things in life that had been closed off to him and just how open the world seemed now. A smile and a wink could go a long way, especially if he was as hot as it seemed he was in the eyes of others. It was a powerful weapon, one he could use to get what he wanted. But it seemed every time he used it he drifted further from his masculinity.
"I will get another heater to dry your nails, this one is broken." Jin said softly, interrupting his reverie. He just smiled and nodded, looking down at his lengthened nails with their beautiful red hue.
He watched her curiously as she moved to the reception placing the faulty heater down and sorting something else out. He watched as she picked up the faulty heater and returned, sitting down and smiling plugging it in.
He looked at her with obvious confusion as she positioned the heater to dry his nails, noting his expression and biting her lip. Hiding it with one hand she showed him a piece of paper.
The piece of paper read, 'Jin' followed by a mobile number. She let him see it then folded it in half, slipping it under his right hand, where Kelly on his left wouldn't notice. She smiled again.
"So.. Where are you going after this?" she asked curiously as the red nail polish dried quickly.
"To the films with them." he nodded to the three girls, "Though I don't know what we're going to see."
She nodded some curious and smiled, her voice lowering to a whisper, "Well maybe if you're free later, or tomorrow.. Or the day after, we could grab a cup of coffee somewhere?.."
He blushed and smiled, "I'd like that.." he said back softly, glancing towards Kelly, though she hadn't noticed, fortunately
He felt a little guilty. He was a starving man who had just been invited to a buffet. He was so unused to female attention that even though he was wildly attracted to Kelly, not as put off by her additional assets as he should be, and virtually her lover, he couldn't help but accept the attention of Jin. That, and perhaps Kelly's remarks earlier about him being hers had made him desire for something a little more… Mutual, seeing this as maybe an opportunity to achieve that.
With his and their nails now dry he stood, unsure of where he could possibly hide Jin's number. After a few moments of hesitation, while Kelly's back was turned he tucked it into the lacy band of his thigh highs. He glanced back to Jin who was smirking, she at least had seen.
As they moved to pay Jamie moved to Kelly's side, she looped her arm around his and nudged him, "You're such a flirt.. You can't put out your charm to anyone and everyone you know, you'll be inundated." she chastised lightly.
He shrugged a little, "Sorry, I'm not used to people.. You know.. Looking at me like they are."
She grinned and squeezed him. "No kidding. Hell, sometimes I wish people looked at me like they're looking at you."
He smiled warmly and leaned against her gently as they paid and walked from the shop as a troupe.
He spared a glance back towards the shop and saw Jin, blowing him a kiss even as he hung off of Kelly's arm.
Jamie smiled and looked forward. Today wasn't turning out so bad.
They walked and talked through the mall towards the cinema, admiring each other's nails, inquiring fruitlessly about Jamie and generally just enjoying the company of each other.
Jamie Lucy and Gemma stood around chatting as Kelly purchased the tickets from an automatic machine, returning to the group and proffering four tickets with a smile. "Back row seats!" she said, excitedly, grinning at them.
Lucy grinned and reached out for a ticket but Kelly withdrew her hand, shaking her head, "Nuh-uh, assigned seats.. I've had my fun.. Your turn.." she smirked knowingly as she handed them each a specific ticket.
Jamie took his ticket and looked at the three of them, curiously, "Their turn?"
Lucy raised her hand to her mouth and moved it back and forth, poking the inside of her cheek with her tongue, mimicking a blowjob.
Gemma smirked and rolled her eyes, "Crude but right.. You won't be watching the movie hun.."
Jamie flushed with color, but Lucy took his hand and started pulling him along. "Come on!! I can't wait."
He looked to Kelly, but she simply shrugged, "You'll love it!"
Jamie bit his lip but allowed himself to be pulled along by Lucy, eying her look of hunger with no short measure of hesitation. He had loved his time with Kelly, he couldn't deny that, but now she was so casually passing him off for her friends to use he wasn't sure how that made him feel. She was supposed to be his salvation, albeit not one from this new lifestyle, but at least from Caitlyn. Would he prefer this? Having no less than three gentler lovers to Caitlyn? Would Lucy and Gemma even be that gentle?
They stopped off at concessions, Kelly buying in bottles of pop for everyone and a box of popcorn for herself, Gemma and Lucy passed and it seemed Jamie didn't get an option but to pass.
Before heading into the theater Gemma excused herself to the bathroom, leaving Lucy and Kelly to fawn over how dainty and wonderful Jamie looked. Though they seemingly waited forever for Gemma, the other two didn't seem to mind. They seemed to enjoy the anxiety once more plaguing Jamie as his mind was awash with thoughts and visions of what was to follow.
Once Gemma reappeared, they made their way through the theater to their screen. It wasn't until he was being guided up the stairs towards the back row where their seats were that he realized he wasn't even sure what they were seeing. Not that it mattered to him, he had no doubt their plans would come to fruition and he would see little of the film.
He sat down in his seat with Lucy to his right, Gemma to his left and Kelly to his far left. The seats were comfortable, with an abundance of legroom. He also noticed how the floor seemed relatively clean, his feet not sticking as he had imagined they would.
He watched as the adverts flickered across the screen, his arms folded over his stomach, as he again thought about where he was.
Lucy whispered in his ear, making him jump slightly. "Heey.. You don't need to look so nervous, it's going to be fun!"
"I've.. I've never.."
"You've never sucked a cock before?.." she pressed, whispering, through her excitement bled through in the sparkle in her eyes.
He thought back to his shower that morning with Caitlyn. The face fucking she had given him hardly counted as a blowjob. She'd just used him like a fleshlight, barely any action required on his part. He shook his head.
"Oh my god.. You're going to love it.." she beamed, squeezing his hand.
"I.. I will?" He asked, genuinely confused. This wouldn't be like with Kelly where he would actually cum from it, it would be work for him, pleasure for her?
"Mmhm. If you're anything like Kelly said and anything like I think you are.. You're going to end up looking forward to sucking cock.." She winked playfully and sat back in her chair, winking across to Jamie as she none to subtly adjusted her jeans.
He sank back into his seat, knowing he had a few moments recourse before the lights dimmed and the movie started. He couldn't deny he was curious. What if he would enjoy it like she said? What would that mean for what little resistance to all this remained?
He looked over to Gemma, taking a moment to admire her. She had been quiet, compared to Lucy and Kelly, but he felt his heart fluttering. Her dark skin was exotic and enticing, her lips fuller and her figure a little thicker, she easily had the largest bust of the three and that had always been a weakness of his.
She glanced towards him and caught him looking. She smirked slightly before glancing back towards the screen, patient, waiting. He looked back too and noticed just how empty the theater was, the others who were in it, all couples were sparsely positioned around the outside and dotted together. Jamie realized that there was no one overly near to them to observe or overhear anything that took place.
Looking across to Kelly he noticed in her relieved expression that this hadn't been any play on her part, just sheer luck.
He modestly adjusted the hem of his dress and admired his nails, thoughts of Jin springing to his mind, though only for a moment. It became difficult to make out his nails as the lights dimmed, the adverts transitioning into trailers.
As the thrumming of the bass filled his ears he felt Lucy's hand on his, "Are you excited?.."
"I'm.. I'm a little nervous.." he admitted, whisper sounding shy. "I don't know if I'll enjoy it.. Or even really how to do it.." he paused, looking over at her in the dark, "And I mean.. I don't even know you that well.."
Lucy pouted a little bit and squeezed his hand, "Hey now.. You'll love it.. You'll be amazing and you're practically one of the girls, that makes me like a sister to you.." She smiled, reassuringly.
Jamie winced internally at the comparison but smiled bravely, nodding a little.
In the dark where it was difficult to make out the others, he felt a little less nervous and anxious. With the sound of the bass obscuring all other noises he almost felt alone. At least until he felt Lucy's hand on his, moving it down into her lap, his hand coming to rest across a definite bulge in her jeans.
She leaned close once more, "Hey, you know those people who finish all their popcorn before the trailers are even finished? Those really.. Really impatient people? Yeah.."
He bit his lip as he looked at her lap, as she released his hand. In the almost dark he could just make out her hands moving, pawing at the blue fabric before the faint sound of a zip cut through the noise of the trailers. He saw her hand delve into her jeans and an all too familiar outline appear.
He flushed with color and watched as Lucy leaned back in her seat, arms either side, looking forward at the screen.
Jamie looked up at her and she only briefly glanced at him, winking before looking back to the screen.
He knew what she wanted him to do. But she wasn't going to say it again. It seemed she wasn't even going to force him.
He pursed his lips some and leaned back in his seat. If she wasn't going to force him, why should he do it? He didn't know her, as nice as she seemed he didn't feel he owed her anything, and unlike with Kelly, he didn't think it would feel good, he wouldn't gain any pleasure from it, so why?
He sat there, looking at the screen for a few long moments, pointedly ignoring her cock in the open next to him. He started thinking back to Kelly and Caitlyn, unable to tear his thoughts away from all that had been happening to him.
The biggest injustice in Jamie's mind was just how big the two girls had been. Was that normal? For their, for a better word, kind, to be so well hung?
He glanced towards Lucy. It was hard to make out the size of her cock in the dark, and it seemed to have shrunk a little bit without his attention, though she looked at him, expectant, impatient.
He'd hold it, just figure out how big it is. Then stop.
He reached a hand across between them and let it lay in her lap, hand moving until he felt the fleshy warmth of her semi hard cock under his questing fingertips. It honestly felt quite nice, so smooth and soft.
As his hand rested on her cock he bit his lip, only semi hard it was difficult to figure out how big it would be as he had really only experienced Kelly and Caitlyn at their hardest. Without really thinking about what he was doing he slowly wrapped his fingers around the length of her cock, holding it by the shaft and started to slowly stroke it, waking it up once more, just so he could measure it, of course.
As he felt it begin to harden again between his fingers he heard her let out a little breathy moan and he felt a little thrill. He remembered with Kelly half of his pleasure with her hadn't just been the physical stimulation she provided but the knowing that he was bringing such a beautiful girl to climax.
As he sat there stroking her cock he knew he had been mentally flip-flopping all day, between accepting Kelly and parts of his new self to defiantly and stubbornly hating every moment of it. He was in conflict, he knew.
What Caitlyn had done to him, using his ass and mouth left a painful spot in his memory and a soreness still throughout his body. But when Kelly had fucked his ass, he'd loved it. Maybe if he used his mouth on his own terms he would enjoy it too?
Worst case scenario, he didn't enjoy it, but he brought another beautiful girl to climax? He blushed at the thought, thinking of Lucy and Gemma both. He'd never in his dreams really ever imagined he would do anything adult with anyone like either of them, especially not at his age and with his body.
Lucy sat enjoying the opening scene of the film and the handjob she was receiving. It wasn't the blowjob she had been hoping for, but a handy from this delicate little goddess would more than sate her lusts. The hand gently working up and down her shaft felt magical, Jamie might have been shy, but it just felt so good. She closed her eyes and tilted her head back, briefly enjoying the sensations and the sensations alone, blocking out the film.
She felt the hand tug down and pause, then a sudden, wet warmth engulfed her cock. With a surprised little noise, she opened her eyes and looked down, grinning. She rested her hand on the gorgeous babes long blonde hair, not pushing, just encouraging.
Jamie felt the tip of her hard cock fill his mouth as he wrapped his lips around it, she was smaller than Kelly and Caitlyn, but still bigger than himself, though his thoughts were already straying from any pretense of measuring it. Being in control this time he was more able to actually take in the experience. The cock felt so foreign in his mouth, the tip silky smooth and spongy to his tongue, the length feeling so soft yet so hard at the same time.
He sucked on it gently, experimentally and he felt Lucy's hand tighten slightly in his hair, a sign that he was doing well, he figured. He pressed his shoulders down and let the cock sink between his lips into the wonderful heat of his mouth, his cheeks caving in on her as he sucked, filling his mouth with her cock, starting to bob his head up and down, recreating what he had seen online.
"Oh gods…" Lucy whispered softly, "And you said you didn't know what you were doing.. Fuck.. You're a natural.."
Despite the context of the compliment he felt more than a little proud, he wanted to do a good job, wanted to make her feel good, whether or not he enjoyed it at that point was secondary to her pleasure.
He took as much of her cock he could fit in his mouth, only sparing a couple of inches and sucked her cock as best he could. His head bobbed up and down as he rolled his plush red lips across her, working her with as much skill as he could muster, remembering to use his tongue as often as he could to rub across the sensitive tip.
With his mouth working almost the entire shaft his fingers made an O around the base, squeezing as he gave the pale skinned freckled girl his first blowjob.
To get to her he had ended up kneeling on his seat, facing her, he felt Lucy's hand glide down his back to, at a stretch, sink her fingers into the plushness of his feminine ass through his dress, squeezing and massaging the doughy rear.
"Mm I can't wait to fuck you, babe.." she cooed gently, "Such a shame Kelly found you first.. I'd have wifed you in a second with a mouth like this and an ass like that.."
Jamie briefly saw the mental image of him as a wife, Lucy's wife, and felt a shiver travel down his spine. He was sure she wasn't being serious, but it felt like there were so many options in his future now, if only he embraced this. If he could just get past that first hurdle. Just accept all of this he could do so much with it. He could-..
"F-fuck.." Lucy's voice, strained suddenly, his thoughts interrupted by a sudden pressure on the back of his head, holding him down as he felt something shoot against the back of his throat, pouring back down her cock to pool against his lips.
He wiggled a little, taken by surprise as she bucked her hips, cock head bouncing against his throat as she came in his mouth. He swallowed all he could but a rivulet trickled down out the corner of his mouth to stain her jeans.
The hot fluid coated his tongue as he continued to suck, draining every drop he could as she writhed up against him. It tasted so unique, a little salty, a little bitter, the texture inconsistent and the heat unfamiliar.
In his mind, he made the connection between that taste and her pleasure. It might not taste the best, but it signified he had succeeded, very quickly, in bringing a wonder like Lucy to climax. And he loved it. Loved that power. He had done that to her, without any input from her.
"No way.." Gemma's voice, mirthful. "You came already?.."
"S-shut up.." Lucy said, defensive, even as she spent her last few drops inside Jamie's waiting mouth, "She's a fucking pro.. I've never had head like that before.."
She gently moved her hand from the back of Jamie's head, letting him move up slightly, the already softening cock popping free from his lips, leaving him panting softly as he leaned in, licking her cock without thinking, catching the cum that had escaped on his tongue and swallowing it.
"Mm.. Such a good girl." Lucy observed before reaching down to tuck herself back into her jeans, letting Jamie settle himself back into his chair.
With his mouth tasting like cum, his stomach feeling the heat he felt he should be ashamed, confused, or just embarrassed. But oddly, he only felt worried. Worried his hair might be a ruffled. Worried his makeup might be ruined. He couldn't tell in the light and he didn't want either to be messed up. Though cutting through that a spark of pride brought on with the words, 'good girl' buzzed in his mind like a high.
Sitting back he carefully wiped his lips, straightening his dress and hair as he watched the movie for a couple of minutes, but found himself disinterested, he wasn't really sure who was who or what was going on, having missed the crucial opening.
With his investment in the movie next to nothing, he turned his attention to Gemma. She didn't seem to notice, to engrossed in the film and he found himself looking down, past the swell of her full breasts to where her cock would be.
Swallowing he moved his hand across to her lap and rested his hand on her thigh, unlike Lucy her member wasn't out and waiting for him, he looked back up to her but Gemma still just watched the film.
He'd had fantasies once or twice about ebony girls, but had never realistically thought he'd experience one. At the same time, however, he'd seen his fair share of interracial porn and then males.. Well. Would she be like that?
Surprisingly keen to find out he dipped his hand into her lap and felt her shuffle slightly, parting her thighs and leaning back to give him better access, his hands moving to the button and zip of her jeans, eager fingers moving to swiftly undo both.
Swallowing, excited, he worked his way down the smooth skin of her mons to the base of her soft cock. He let his fingers wrap around it and started to urge it free of its denim confines.
He felt his heart skip a beat as he struggled to pull the mass of ebony flesh from one leg of her pants. It was significantly larger than Kelly and Lucy, while still being soft. He looked up to her, wonder in his eyes.
"H..How big?.." he asked daintily, whispering low.
She shrugged modestly. "Twelve.. Thirteen inches?" she replied gently, without looking away from the film.
He stared at her in disbelief, then down at her member, pulsing gently in the soft grip of his hand. She didn't seem to be kidding. He wanted to experience this properly, give it the attention it deserved.
He slid from his seat and moved to kneel between her thighs, it was cramped, between her legs and the seat at his back but he was comfortable enough, for a while at least.
Kneeling as he was he brought himself to eye level with her beast, the cock pulsing softly in his hands as it started to swell. He moved both his hands to encircle the cock, one above the other and started to slowly stroke. In the darkness of the theater she could see that, as a first for him, she seemed uncut, her cockhead sheathed in her dark foreskin.
He leaned forward and kissed the tip, feeling the odd texture of the wrinkled skin under his lips as it swelled, his hands sliding up and down the length, gripping it tighter and tighter as it swelled.
Biting his lip he pushed his hands down, drawing the tip of her cock out as it swelled. The tip was slightly lighter in color making it stand out against the blackness around it. He leaned in and kissed the exposed tip, taking it into his mouth as he pushed his shoulders forward, rolling the foreskin of her cock back until the mushroom tip was fully exposed, taking it into his mouth where he lavished it with his already renowned tongue.
It was so much more difficult as it hardened fully, the tip of her cock almost entirely filling his mouth, his lips stretched wide around the girth of her shaft and his tongue unable to circle entirely around her tip just due to its sheer size. Unless she was as quick as Lucy had been, he was sure he'd come away with this with a sore jaw.
He employed all his Lucy-tested tricks, taking her cock as deep into his mouth as it would go, which admittedly wasn't much compared to Lucy, sucking hard and working his tongue against the sensitive underside of her tip, lips rolling up and down the ebony pole as his hands massaged, stroked and caressed her length.
Minutes past as he serviced her, doing his best to make her pop but as he paused, taking the cock from his mouth to look up at her, kissing the length as he regained his breath he noticed a passivity in her expression. She wasn't closer, she wasn't edging, she wasn't even breathing that hard. She just seemed to be enjoying the film.
This irked Jamie a little bit. He'd felt pride in his work with Lucy and he felt he should have the same effect on Gemma.
She looked down at him, her thick black shaft resting across one side of his face as he kissed the underside and winked before looking back to the film.
He found himself blushing. This was a personal challenge to him. He would make her cum. Regardless of how stoic she seemed. He would just have to try something new. Or something old? He thought back to that morning, kneeling in the shower as Caitlyn forced her cock down his throat. It had hurt so bad when he had done that and in his panic, he had gagged and wretched. But hadn't he felt the same way about his ass? His time with Caitlyn had been painful, but given patience and the right circumstances it had felt alright with Kelly?
He thought for a few moments before taking the tip of her cock back between his lips and steeling himself mentally, if he was patient and careful, he was sure he could make this work.
He took her cock into his mouth, the hot shaft filling it as the huge mushroom tip bumped against his throat. It was uncomfortable and he felt the urge to gag, but he suppressed it, forcing it back as he bobbed his head up and down, letting the tip of her cock nudge against his throat time and time again, forcing him to acclimatise to the sensation, trying to trick his body into understanding that it was alright.
It took a while but it started to feel okay, her cock was shiny with his spit and his mouth was starting to get sore from being stretched. But with each attempt his confidence was growing, even as his frustration did. She still seemed.. Well, bored! He would make her cum. He would drive her to pleasure, if he was going to suck cock like a pro, he was at least going to make them feel the best they'd ever felt.
He gripped the base of her cock with both hands and pushed himself forward, feeling it bump against his throat once more, only this time he didn't let up. The urge to gag was still there but he could suppress it now, forcing it back as he applied more and more pressure.
With a flare of pain, he felt the tip of her cock press into his throat, his lips sliding down an extra inch or two down her shaft as she delved into him.
He held it there, eyes squeezed shut for as long as he cope before pulling back, freeing the cock entirely from his mouth and panting, looking at her cock, a single line of spit joining it to his plush lower lip.
He swallowed and moved forward again, once more taking her cockhead into his throat and holding it there, taking it easier and holding it longer. He repeated this, time and time again, each time doing better, each time feeling less sharp pain, though the soreness was a constant.
But still, she didn't cum. She pulsed and throbbed, her cock remaining hard as he lavished it but it wasn't enough.
Jamie felt stubborn, he felt he'd lowered himself this far, he couldn't give in and surrender now, couldn't fail. What would be the point if he couldn't even get her off? He would have to go all out. Have to push himself further still.
One hand still gripping the base of her cock he let his tongue run over the entire length of her shaft, from the base to the tip, kissing where he couldn't lick, his other hand sliding down the outside of her thigh to work his fingers under her round ass.
With her cock fully wet and his hand in position he again took her cock between his sore lips and leaned forward, the tip of her cock fitting snugly into his throat. But he didn't stop. Didn't slow. Pushing his head down and pulling up with his hand for leverage he forced her cock into his throat, the bulge of her thick tip visible as it pressed down his throat, filling him.
The pain was like nothing he had never experienced before, sharp and in a place he'd never experienced pain before. But the reward overruled it. He felt his chin press again denim, his nose in the soft flesh of her mons.
He held himself there, forcing himself to deepthroat the entirety of her cock, feeling his lips leave a ring of lipstick around the base of her shaft, his tongue pressed down hard in his mouth, his throat bulging obscenely as the imposing heat filled him.
"Holy fuck.." he heard Lucy whisper in amazement, and he knew it wasn't at the film, but at the show, he even heard Kelly take a sharp intake of breath. They were, it seemed, as astonished as he was.
Slowly, with a lewd, wet noise he drew the cock from his throat, sitting back and panting hard as the cock twitched and throbbed before him. As he looked up to Gemma he saw her biting her lip. The first sign he'd seen in her that she'd even noticed his efforts.
He heard Lucy shift into the seat he had been in and felt her hand on his, guiding it to her own cock.
He wrapped his fingers around her smaller, but still hard shaft and started to stroke it, jerking off the eager redhead even as he focused on Gemma. One hand still under her.
Time passed and the movie played in the background as Jamie varied his techniques, switching from long, deep strokes into his quickly acclimating throat to focusing every iota of effort on the very tip, swirling his tongue around it, kissing and suckling on it. He could see it was having an effect on her, finally, his efforts starting to shine through even as he exhausted himself.
He had been going for it felt like forever before he heard a voice, "H-hey.. I'm almost there.. Swallow it.." He opened his eyes and looked up at Gemma, excited he'd finally accomplished his task. But she just looked bemused. He looked to his side, where he was still stroking Lucy's cock, absentmindedly working her with his soft feminine hands. She was squirming in her seat, face flushed.
With a slight whimper of regret, he moved from the cock he was working to Lucy and with absolutely no effort slid her cock into his mouth and throat, taking her to the base without feeling any urge to gag or discomfort.
She gasped at the sudden pleasure and gripped his hair, he felt her cock pulse, felt her hips twitch and felt a familiar heat in his throat. He swallowed, once, twice, three times, drinking each shot of cum as she gave him it before she once more relaxed, spent far quicker than she had been the first time.
Giving the tip of her again spent cock a parting kiss he switched back to Gemma, taking back to his task without a seconds hesitation.
Sucking, licking, throating, kissing, he tried everything again and again until his mouth, his throat, even his hands and shoulders were sore. He was sure the movie was almost finished and he had spent almost the entire length of it worshipping her entire length. Helplessly he continued, desperate to finish her before the film ended, even as he exhausted himself, giving it his all.
As he started to lose hope he felt her hand on the back of his head, her first participation since he had started, it seemed, forever ago. With this he felt a renewed vigor, redoubling his efforts, sucking harder, bobbing faster.
He felt her guide him, up and down, driving the length of her cock in and out of his mouth and throat, her eyes on him now as he took her from tip to base, lips puffy from the constant attention, his eyes wide as he looked up at her, making eye contact.
She bit her lip and pushed him down hard, hilting him on her massive ebony shaft, dominating him with it. He felt it throb and pulse, harder than it had been. With a surprise he realized she was cumming, so deep inside his sore throat he could barely feel it as she deposited her load directly into his stomach without any need for him to swallow.
Finally, he'd done it, he'd made her cum. He was exhausted, pained and generally sore all over from being in such a cramped space for so long. But none of that mattered. He'd made her cum.
Slowly she pulled him up and off her flagging cock, leaving him, head resting on her thigh, panting with his eyes closed, recovering from the self-imposed ordeal.
"How the fuck did you last so long?.." Lucy asked gently, jealousy teeming in her voice.
Gemma let out a soft little chuckle, "Jerked off before I left work.. Then again in the bathroom, before we came in here.. Wanted to make her work for it. And fuck did she.. Best head of my life, hands down, no contest."
Lucy swore under her breathe, "Aww fuck.. I wish I'd had that idea.." she leaned back in her seat and he felt Gemma's hand gently caressing and unmessing his hair, that she had worked so diligently on just a few hours before.
Jamie breathed an inward sigh of relief. He'd sort of been tricked, sort of been manipulated into spending hours giving head. But he honestly didn't mind. He was just happy that he'd done good, that he hadn't wasted his time or hers.
As the movie came to a close he stayed between her thighs, too tired to move back into his seat for only the last few moments, enjoying the comfort of her fingertips skillfully arranging his blonde locks.
As the credits rolled and the house lights came on Jamie found himself blinking up into the light and into the beautiful faces of Kelly, Lucy and Gemma.
"..For fucks sake.." Kelly sighed, causing Jamie to put on a look of worry. "It's just not fair."
The three of them looked down at Jamie, nestled snugly between Gemma's thighs, his lipstick was all but gone, painted over Lucy's and mainly Gemma's shafts, but other than that, with his hair rearranged, he looked perfect. The makeup on his face and eyes unsmudged, his expression doe-eyed and wide with concern, not understanding what they were looking at.
"W-whats wrong?.." he asked, timidly.
Kelly shook her head and smirked a little, "You're too fucking beautiful for your own good."
He blushed softly and looked to Gemma. He saw an affection in her eyes that hadn't been there before. "Mm.. And you're such a good girl.."
He felt a flush of pride rush through him at those two simple words. Good girl. He wanted to hear them again. Wanted to feel that.
"I.. I did okay?" he said gently, smiling a little.
Gemma grinned, "Girl you just self-taught yourself to deepthroat just to get me off. If you weren't Kellys.."
"Heeey.." Kelly nudged Gemma, albeit playfully, "Mine.."
"Yeah I know I know. Just saying is all. She's a keeper."
Kelly looked down at Jamie and smirked knowingly, "Ooh I know. I'm working that part out.."
Gemma and Lucy spared a glance for each other before looking to Kelly, Lucy speaking first, "Kelly.. Just who is she?.. Where'd you find her?"
Kelly bit her lip and looked down at Jamie. He could see the internal debate in her mind, whether or not to tell them.
"..You know Caitlyn?"
Gemma grunted a little, "The woman who made you her bitch, yeah?"
"I'm not her bitch!" Kelly said defensively, voice a little louder now the other moviegoers were filing out of the theater, "Sometimes a girl just likes it rough you know?"
"I could give you-"
"Without being split in two, Gemma." Kelly smirked.
Lucy rolled her eyes, "Yeah but what's that got to do with her?"
"Alright.. Well." Kelly sighed some, "Alright so Caitlyn's got a little brother, just turned eighteen."
There was a pregnant pause as Kelly left the two of them to make the connection.
"Oooh fuck.." Gemma breathed, hesitating, "Wait, didn't you say this sweetie got turned out?"
Kelly nodded, somber.
"That's just wrong." Lucy chimed in, "You mean your own sister turned you out?"
Jamie just nodded a little, looking so small, innocent and vulnerable between Gemma's thighs it triggered a spark of protection in all three of the girls looking down at him.
"Caitlyn asked if I could take her out for a day, make her up to look really pretty so she could have more fun with her tonight.. I thought why not, would be fun, maybe I'd get to play with her too. I'd known Jamie for long enough anyway.. Always was kinda cute, always sweet to me, always crushing on me.." Kelly explained, causing him to blush a little. "Now I don't want to hand her back, don't want Caitlyn to hurt her.."
