Dean paused, wondering if there was a punch line in there, or something he was missing. The smirk caught him off guard and he wondered if somehow he'd asked the wrong question. He swallowed, decided not to let it bother him. She was a good distraction, no reason to end the conversation now.
"I'm Dean." He waited a moment before continuing. "What, no backstory on you to finish out the introductions?"
She chuckled, a deep rasp that actually hit him under the collar just right. "Out of college two years now. Had plans to leave like the rest of the kids my age. Got pulled back after I graduated to take care of my mom."
"You're stuck in one place. I'm never in one place for very long," Dean murmured under his breath. Rhonda remained quiet and Dean couldn't tell if she'd heard him or not.
Just as he raised his glass, Rhonda asked, "So which one caught your fancy?"
Dean froze, turned slightly to face her. "What?"
She flicked a hand at the pool tables and repeated, "Which one caught your fancy?"
Dean choked on his most recent sip, raising a hand to cover his mouth. Grabbing the napkin being held in his face, Dean wiped his mouth. A flush rose to his cheeks, eyes darting to the bar top and staying there.
"So?" Swallowing thickly, Dean refused to lift his gaze, fingers biting into his knee and knuckles white around his glass. "Oh come on," she dropped her voice, "You gonna try and tell me you weren't just checking the guys out over there?" She waited and Dean saw her eyes roll. He clenched his jaw. "The whole time I've been talking to you, you haven't once tried to hit on me, look down my shirt, or buy me a drink. You barely took half a second to look at the girls when I was talking about them…Aaand you've spent more time than you probably realize watching the guys down there and almost drooled when I pointed over at the pool table."
Dean would be lucky if he walked out of here breathing tonight. His chest felt so tight he couldn't tell if he was pulling in air. Lifting up slightly from his seat, Dean pulled out his wallet and fumbled out a few bills, shoving it back in his pocket as he slid off his stool.
Before he could take a step, Rhonda put a gentle but firm hand on his wrist. "I've been told on multiple occasions that I have a habit of over-stepping. They're probably right, but well, it's gotten me this far." She shrugged. "Look, I don't know what exactly your situation is, and honestly it's not my business, but would you like to come home with me?"
Again, Dean froze. "What?" He couldn't wrap his head around that one. She'd seen – she'd literally pointed out his interest in men. He stared at her.
Rhonda licked her bottom lip and met his eyes, leaning in close so he could hear her whisper. "You have a thing for cock. I just happen to be a bit kinky. I'm thinking we can work something out."
Dean choked on his next breath. Who the fuck just came out and said stuff like that? He was surprised, but part of him was turned on, the part that must have reacted to her voice earlier in the night.
With the situation from earlier that evening, Dean knew hooking up with men wasn't exactly the safest thing he could do. He'd been lucky with both Aaron and Gavin, but Beard had proven to him that his fears were founded in real possibility and Dean couldn't risk being stuck in a position where he couldn't get out. This might be a good way of figuring out what was possible. It wasn't what he expected out of this night, but there was still a desperation pumping through his veins, a need to be with someone, to be filled. And it sounded like maybe Rhonda could do that for him.
Why the hell not? Dean met her eyes. "Okay," he breathed.
At her apartment, Dean perched on the edge of the couch, sweaty palms pressed to his knees. Rhonda was in the kitchen getting them drinks, an effort to ease them both into what would come next, but Dean wasn't sure anything would help, not with this. He peered around the room, eyes flicking from the crochet blanket bunched on the other end of the couch to the blank TV, to the stack of magazines on the coffee table, to the heap of movie tapes knocked over on the floor.
"Trying to find my super secret stash of kinky porn?"
Dean froze and looked up at Rhonda where she leaned in the kitchen doorway. "Wh-what? No." Dean wasn't sure his answer was convincing. He was a bit taken aback by her forwardness and how uncomfortable he was around her. He was usually so smooth around women that it was discomfiting how much he didn't have figured out about this one.
"Relax Dean," she laughed, coming out to sit with him on the couch, handing him a beer and curling up with hers against the pillows. "I'm kidding hon." She patted his leg. "You sure you wanna do this?"
There were words, words he should be saying, but Dean was again stuck in place, unsure how to proceed.
"How 'bout this. I tell you some ideas I have for how tonight could go and you nod yes or no." She raised an eyebrow at him, an encouraging smile gracing her face.
Breathing deeply, Dean nodded and allowed himself to be pushed back into the cushions. Rhonda gave him an assessing look. "Before I say anything else, I need to know your preference. Are you a top?" Dean inhaled but didn't move, couldn't. "Bottom?" She prompted.
Blushing, Dean gave a short nod. So much for all that confidence Aaron encouraged him to have. He was back to blushing and not meeting people's eyes like nothing had changed.
"Interesting," Rhonda remarked, trailing a finger down his leg. "Nothing to be embarrassed about. I find it…very hot." Dean's cheeks flamed. She smirked, "Let's get to it then. Feelings on a hand-job." Dean nodded.
"Blow-job." Another nod. "Fingering." Dean swallowed thickly, but lowered his chin in a nod.
"Toys." Dean paused, staring at her considering. "Like a dildo or a vibrator." Dean lifted his chin this time, another yes. He was baffled by how straightforward she was about all this, how unashamed.
"Pegging," she offered, this time with a brow raised. Teeth sank into Dean's bottom lip, his mouth suddenly dry. "As in I would –" She was cut off by Dean's nod and grinned. "So you do know what that is. Good. Bondage."
Immediately, Dean shook his head, on guard. Rhonda raised her free hand. "Just a suggestion hon. No biggie. Spanking." Another shake.
She nodded in understanding. "Can I touch your nipples?" Dean couldn't help the laugh that escaped, but he nodded, settling back more easily into the couch.
Rhonda sipped her drink, watching him. She wet her lips. "Panties." Again unsure, Dean froze, eyes flicking up to hers and remaining there, trying to figure out if she was joking with him or making fun somehow. He started to shake his head, then stopped, cocking his head at her. A smile answered him. "I think you'd look fucking hot…and what's this night for if not a little experimentation. You up for it?"
Tongue darting out to wet his lips, Dean looked away, thinking. He was suddenly desperately curious and despite his misgivings, he nodded.
"Wonderful. You want to finish that drink or jump right in?"
Dean looked at the bottle sweating in his hand in surprise. So absorbed by Rhonda's suggestions and his discomfort, he'd barely managed to take more than two sips. He tipped it back and sucked down a few deep swallows before setting it on the coffee table and standing. "Let's go," he managed to rasp out, extending a hand to Rhonda on the couch.
She husked a laugh and allowed him to guide her up, then pulled him along to her bedroom.
Inside the room, Dean was surprised to find a mixture of furniture and decorations that didn't scream mature super confidant intimidating woman like he expected. He'd half expected her room to be a combination of deep reds, blacks, and leather, but what the fuck did he know. Instead her room was painted a light green, gauzy sequined curtains draped over the windows. Her bed cover was cream-colored, plush and far more innocent than he'd imagined with a stuffed rabbit leaning against the pillows. A glance around showed him a dresser, the top drawer hanging open with fabric spilling out, a small pile of clothes pooled in front of the closet.
Dean inhaled deeply, her humanness calming him, allowing him to relax somewhat. Something about seeing her space put him at ease. She seemed to sense the tension leaving him and tugged him further into the room, pushing down on his shoulders so he was seated on the end of her bed.
With him seated Rhonda stepped back and walked around him, bending to open a large drawer built into the frame of her bed. Dean turned to watch and his jaw dropped instantly at the sight of so many panties. "You want to take a look?" Rhonda asked, peering up at him from where she was crouched.
Dean simply nodded, wide-eyed. Rhonda dropped into a cross-legged position and patted the spot next to her. Feeling awkward, Dean slid to the floor and sat next to her putting his hands in his lap. "Here silly, go through them, see if any catch your attention."
There were so many Dean was overwhelmed – lace and satin and silk, mixes of different fabrics, bows, scalloped edges, bikini cuts, briefs, boy shorts, assless, crotchless, and ones with straps going places he didn't understand. The red in his cheeks was starting to feel like a health-hazard. Was it possible for so much blood to be in his face and for the rest of his body to still function?
Rhonda was gliding her hands through the piles alongside him, assessing and discarding as she went. Dean didn't know where to begin. He pulled back and laid his hands on his knees. Noticing how Dean retreated, Rhonda turned to him and smiled. "Maybe I should pick?"
Dean met her eyes. "Please do," he managed, "I've got no…" he fumbled over the words, raising his hands to show his confusion. "There's so many."
Rhonda laughed, her eyes lighting up with humor. "Sure are, and oh the memories attached to some of them! How 'bout you take your clothes off and I'll find a good pair for you." She shooed him away.
Amazingly Dean felt some of the tension ease again, and climbed to his feet. As he shucked his clothes, he couldn't help glancing over and breathed a sigh of relief when he saw a strappy pair fall in the discard pile.
As soon as he was down to his boxers, Rhonda announced, "Got 'em. These'll look perfect on you." Dean turned to find satiny pink panties with black lace sides dangling over her finger.
"Pink?" Dean asked, disbelieving.
Rhonda smirked. "Your cheeks inspired me, hon. Pink looks good on you."
As if to compliment her words, Dean's cheeks lit up once more, heat spreading over his face and down over his chest. Snatching the panties from her hand, Dean dropped his boxers around his feet and stepped into them, amazed to find that the fabric felt fucking awesome gliding over his skin. He drew the waistband up and had to maneuver a bit before he settled his cock into a somewhat comfortable position. He was squished and was convinced he looked ridiculous, but they were on.
Standing by her closet, Rhonda crooked a finger at him, a knowing grin on her face, and going over to stand by her, Dean was spun to face a mirror. He sucked in a breath. Part of him was still scoffing at the idea of him in panties, but the part at the forefront right now was preening, amazed at how good he actually looked in them and how comfortable they were starting to become. A black bow adorned the front as if decorating his cock and even that was strangely enticing. "Fuck me," he murmured, staring at himself.
From behind him, Rhonda chuckled. "Plan to." Dean rubbed a hand over the back of his neck. She laughed again and patted his ass. "Keep admiring yourself. I'm going to get a few things ready."
He heard things shuffling and moving around for a minute and then she was gone. For a few minutes Dean was alone, just him and his reflection. Damn, he looked surprisingly good and definitely not as stupid as he'd feared. His curiosity had been worth it – these looked and felt amazing. He turned to see his ass. His cheeks peeked out of the bottom, the material cut more narrowly just for that effect.
He'd fuck him.
The more he stared, the more enamored he became. His cock twitched and Dean groaned, the feeling of the fabric pressing back on him strangely arousing. He reached a hand down, cupped himself, and moaned at how sensitive he felt through the material. He was getting harder and licked his lips when he saw the wet spot blossoming around the head.
A clatter sounded in the apartment and Dean remembered he wasn't alone. "You coming back?" He called, suddenly feeling stronger and more confident than he had all evening.
"Just a sec!"
As he waited, Dean wandered back over to the bed and sat down, leaning back on a hand. The other settled on his thigh and watching his own lap, Dean trailed his fingertips over his leg, over his belly and up his chest. He pinched a nipple and groaned, cock twitching in the panties, wet spot spreading.
"Fuck," he heard whispered from the doorway. He glanced up lazily, eyes hooded, and grinned crookedly at her.
"Like what you see?" The words came out in a husk, arousal clouding his vocal chords.
"Oh yeah. Goddamn, you look fucking stunning." Rhonda was looking at him with pure lust in her eyes and even though it was a woman, Dean could feel himself responding, felt the arousal heating his blood, making the desperation from earlier come back stronger. She went over to the nightstand and organized whatever she'd brought into the room before coming back and just standing in front of him.
After a moment of admiring him, Rhonda dropped to her knees and situated herself between Dean's legs. She trailed her fingers from his knees up to the crease between his groin and thigh, grinning at the hiss that escaped Dean's lips. She feathered her fingers over his skin and as one hand braced on the inside of his thigh, the other curled around his cock, pressing the smooth fabric into his skin, sending his head rocking back.
The soft pressure was making Dean crazy and the lighter she touched, the more Dean tried to rock his hips forward, desperate for more contact, for harder. Rhonda teased him for endless minutes, drawing back each time Dean sought out more of her touch and pressing harder each time he settled. She laughed throatily, Dean's cheeks reddening even as he again rocked his hips into her palm.
Teeth bit into his bottom lip. And then finally, finally, wet heat was on his cock, Rhonda's mouth sucking in gentle motions over him through the panties. She lapped at the sodden spot in the fabric, teasing him in elongated strokes that both gave him the sensations he needed and denied him the full pleasure of it. As she sucked at the head, her hand moved to cup his balls, rolling them in her palm and triggering another roll of his hips. Dean breathed a moan, amazed by how satisfying this strange experience was becoming.
Hands soothing back down Dean's thighs, Rhonda sucked harder at Dean's tip through the material. Dean's back arched, a soft sound emitting from his throat, a cross between a whine and a whimper. And then Dean was in motion, his hips jerked roughly to the edge of the bed, his ass situated just this side of falling off.
An embarrassing squeak left his lips and Dean felt the blood rush to his cheeks even as more rushed to his cock making it twitch within its confines. Before Dean could voice his – discomfort? surprise? Dean didn't quite know what he was feeling in the moment – Rhonda had followed the first motion with another, tipping him back and pressing his legs wider.
He was still wearing the panties, but he'd never felt so vulnerable while still wearing any sort of clothing – flat on his back, legs bent into his chest, ass in the face of the woman between his legs, Dean was feeling very vulnerable. Not knowing what else to do besides accept whatever Rhonda decided to do with him, Dean closed his eyes and curled his fingers into the fabric of her comforter.
Rhonda dipped back down, sucking softly at his cock through the fabric, tongue tracing in wet circles around the head of his cock and down to the base. She again massaged at his balls through the panties and then she was soothing his legs back down to drop limply over the edge of the bed. She feathered her fingers over Dean's stomach, her mouth still sending bliss through his body until she pulled away and fingered the waistband of the panties, lifting them up and over his cock to settle them below his balls.
The feeling wasn't exactly comfortable, the fabric pulled taut where it was pulled tight against the swell of his ass and now down below where it was supposed to be, but it was still strangely sexy. Dean felt debauched and it was exhilarating. His fingers flexed in the covers.
"I'm gonna suck your cock now," Rhonda's voice husked from between his legs, her hands again pushing his thighs up, situating his heels on the edge of the mattress. He groaned and lost his breath as in one fluid motion she sucked him down.
Between one second and the next, Dean was engulfed in hot wet rapture. What pleasure he was experiencing through the panties, was now magnified, his cock now encased by her mouth, squeezed tight by her throat. He gasped and bit back a shout. Her teeth had just barely grazed him as she'd pulled back, but that too was amazing and Dean felt any and all embarrassment or reservations he'd still had about this night disappear.
He'd had blowjobs before, been with women before. He'd even enjoyed women before, but since realizing his desire for men, that enjoyment had paled and lost its appeal. Dean had been highly skeptical about going home with Rhonda, even more so when she asked him to put on her panties, but it was perhaps because, no it was definitely because of the panties, because his boundaries were being pushed, that this was turning into an awesome experience, one of the best of his life.
Dean groaned as Rhonda again sucked him all the way into her throat, swallowing around him. It had been so long since he'd felt this good. The whole reason he'd gone out tonight was because he'd so desperately needed to feel this way. A woman between his legs or not, Dean was feeling fucking amazing.
As Rhonda sucked him down and bobbed over his cock, her hands rubbed at his thighs, soothing over his skin and adding to the sensations. Goosebumps rose on his skin and then Dean was jerking his hips up, startled when a hand trailed onto his ass and then between his cheeks, massaging at his hole through the silky fabric. One finger pressing firmly against the furled muscle, Dean choked back a whimper, suddenly desperate for more. God, he needed more. Fuck. His hips jerked again and Dean was lucky Rhonda was so into this or he might have an angry chick on his hands for nearly choking her.
With Dean still in her mouth, Rhonda pressed more firmly, the tip of her finger just breaching Dean's hole. "Oh fuck," he gasped.
She pulled off and smirked at him. "Good, huh?"
Dean swallowed thickly and nodded. "Please," he whispered.
"Mm, you got it hon." Rhonda patted Dean's hip and stood, going to the side table and coming back with a tube of lube. She waved it next to her face and grinned. "Let's make this as smooth as possible, huh?"
Dean blushed and closed his eyes, grateful when Rhonda simply knelt back down and didn't say anything else. He heard the click of the lid opening and then a wet squelch. He licked his lips nervously, jumping when he felt her fingers worm their way under the panties and smear over his hole. Without pressing in, Rhonda pulled her hand back and returned to the outside of the fabric.
Cock bobbing against his stomach, Dean was eager to continue, but again, he was feeling a bit nervous. Rhonda rubbed at Dean's hole again through the panties, leaning in to lap at his balls. She pushed a fingertip inside. Dean sucked in a breath. "Won't that ruin them," Dean managed around another gasp.
Rhonda responded with her lips grazing his cock. "Don't you worry about that. Just focus on how good this feels." All Dean could do was nod, hips rocking into the different sensations. "You should see how amazing you look," she whispered, almost not talking to him.
Rhonda pushed in deeper, his ass sucking her finger and the panties inside without a fight. "Oh god, oh god, fuck!" Dean bit his lips and imagined what it must look like as Rhonda's finger disappeared completely inside him, panties puckered around the digit and just as deep in his body. The lube eased the way and without warning, Rhonda pulled out and pushed in again, this time with two fingers. She fingered him until he was breathless and gasping for air, and then kept going, whispering how hot and amazing he was under her breath.
Dean couldn't breathe, his lungs fighting to take in air as his ass clenched around her two fingers. For a brief moment, Rhonda paused and then again she continued, but with three fingers instead of two. A choked cry left his lips and Dean lifted his hips to meet her fingers, rocking against the strokes of her hand, desperate for more, to feel her deeper. "Please," he whispered through bite-swollen lips. "Please."
"I gotcha, Dean," Rhonda soothed, fingering him just a little longer before pulling her fingers out. Staring at the ceiling, Dean waited, anxious to continue. And then there was something else pressing at his hole, something more solid and rounded than Rhonda's fingers, not so warm.
"W-what–" Dean tried to ask.
Lifting it so he could see, Rhonda answered. "It's just a vibe Dean. You still okay with that?" Licking suddenly dry lips, Dean nodded.
Smiling, Rhonda moved the vibe back against his hole and gave it a little pressure. Dean's breath caught in his throat as just the tip slid inside, pushing the panties back into his lube slick hole along with it. As Rhonda pressed it deeper, filling him up, Dean's back arched off the mattress and his fingers clenched tighter in the comforter, curling fabric around his hands.
"You're so hot Dean, doing so well with all this," Rhonda encouraged. Dean's head dropped to the side, unsure but really wanting to believe her.
Then with the vibe situated deep inside, panties still pressed deep, Dean felt it rip to life, vibrations rushing through his body all at once. Dean sobbed, tossing his head, his whole body tensing at how completely engulfing it was. He briefly recalled the intense feeling of the electric toothbrush Sam had retrieved for him, but this – so deep inside, so strong – this was so much more.
Rhonda stroked a hand over Dean's thigh and over his hip, holding him in place as she began fucking him with the vibrator. It wasn't exactly thick or even all that long, but after all the buildup Dean was feeling extremely sensitive and like he could come from just this. He moaned and held back a cry as finally, fucking finally, the little device hit his prostate.
His hips shot off the bed, rocking hard into Rhonda's hand. Dean tried to muffle his shout as Rhonda drove it inside again. Fuck, this was amazing. For endless minutes, Rhonda fucked Dean with the toy, twisting it and angling at different times to add to his pleasure, surprising him into cries of delight when the vibrations hit just the right spot.
"P-please," Dean murmured, head tossing to the side. Eyes rolling back, he couldn't stop the words from spilling out. "God, Rhonda please. I need more."
Rhonda pounded the toy in harder for a few strokes. "Can't take anymore Dean? Does your hole need a big fat cock?" Dean felt his cheeks flare red in embarrassment. He refused to meet Rhonda's eyes even as he lifted his hips to meet her hand. "I've gotcha Dean, don't worry. I'll fill you up real soon."
Dean huffed a breath, panting as Rhonda's pace continued unhindered. His chest was tight, stuck between inhaling and having the air punched out of him on repeat. "Pl-ease," he moaned with what little breath he could manage.
Rhonda smirked and finally, finally switched the vibe off. Dean gasped for air, his thighs trembling as Rhonda slipped the toy free. The lube-soaked panties pulled free as well and Dean made a face at the uncomfortable feeling.
Chest heaving, Dean peered down the length of his body at Rhonda who grinned wickedly. She patted the outside of his thigh as she dropped the toy to the floor. Surprising Dean, she dipped her fingers under the waistband of the panties and tugged, urging him to lift his hips as she pulled down and guided the now soaked and stretched fabric over his still hard cock and free of his legs.
"Scoot up," she said, her eyes dark. Dean swallowed hard and did as she asked, sliding his body backwards until he met the mound of pillows settled against the headboard, dick bobbing with the motion. Feeling an uncomfortable shape at his back, Dean reached behind him and pulled out the stuffed rabbit he'd first noticed when entering the room. Snorting a laugh, Dean perched it on the nightstand, hearing Rhonda chuckle as he angled its face away from the bed. Adjusting so he was leaning comfortably, Dean watched as Rhonda followed him up the mattress and knelt between his legs.
"Comfy?" Rhonda asked, raising an eyebrow.
Feeling a tad bit more confident than earlier in the evening, Dean snorted again and nodded, resting a hand low on his belly, thumb and pointer framing his cock, legs splayed around Rhonda between them. "Wonderful," she leered, settling her hands at the tops of Dean's thighs, her thumbs gently stroking the crease between leg and hip. "Stay just like this," she guided, easing his shoulders further back and adjusting his legs so his hips were settled a little further down the mattress. She feathered her fingers over his chest, grazing over his nipples and then his cock before reaching for the lube.
A slurping suction sound echoed in the room and Dean flinched, again trying to ignore the fact that there was a woman rather than the desired man about to fuck him. He breathed deeply, watching Rhonda through barely opened eyes. Gel on her fingertips, Rhonda watched his face as her hand neared his ass, biting her lip against a grin as cold met heat-warmed skin. Dean hissed and glared mildly at Rhonda, shifting his hips in a pointless attempt to escape the cold.
Still open from the vibrator, Rhonda was able to press right in with one finger, curling the digit and then pulling back to add another. The near immediate increase in size forced a groan from Dean's throat, but the width and pressure felt good and god, it didn't even matter that the fingers belonged to a woman. They moved with practiced ease and in seconds were pressing just right on the sweet spot inside, Dean's shoulders pressing deeper into the pillows as his hips fought to lift into her hand.
With a few more presses and tickling massages over his prostate, Rhonda added another finger, the three now scissoring apart and twisting and curling to send lightning strikes through him. Dean's mouth was dropped in bliss, unable to contain the quiet mewls of pleasure as she continued to hit all the right places in just the right way. It was truly remarkable how good she was at playing his body.
Dean's hips rolled into her hand and he groaned, desperately needing to come. Rhonda hadn't pushed him that far yet, holding back just enough that he hadn't fallen over the edge, but he could feel the need growing.
Dean's hands gripped the comforter, fighting back a surprised groan as Rhonda pressed in a fourth finger. "Holy fuck," Dean bit out, his chest tight with the inability to pull in full breaths. She pumped her hand in quick short motions, spreading her fingers with each thrust inside, flexing them to drag over his sweet spot. A twist of all four fingers sent another bolt of pleasure through his spine and Dean couldn't hold back a whimper. His hips rocked down into her hand in a desperate bid to get her deeper inside.
Seeming to know what he wanted, Rhonda retreated each time he pushed down against her, again keeping him just this side of coming. Even still, Dean could feel the heat building in his lower stomach, felt his abs tensing, jaw dropping as the pleasure built, and then a tight grip wrapped around the base of his cock, a thumb pressed rigidly against the underside.
An embarrassing sobbing sound escaped Dean's throat, his knuckles white where they curled deathly tight in the fabric beneath him. "Not yet Dean," Rhonda whispered, her voice a low rasp in the otherwise quiet room.
"I-I need," Dean shook his head on the pillow, tears pricking the backs of his eyes he so desperately needed to come.
"I know. You still okay with all this?" Dean gave a wide-eyed nod, floored that she was even asking. Wasn't it damn fucking obvious? "I need to hear you say it. It's important Dean."
Dean wet his lips. "Yes, I'm okay with this. Now fucking get on with it."
"You've got quite the mouth," Rhonda smirked, leaning back on her knees. "One last question. Do you mind if I take my clothes off?"
Dean froze, thoughts jarring and suddenly feeling really bad and unsure about how he'd come across to her. "Of course not! I'm just – you're just – I," Dean stumbled. "You're a beautiful woman, I just um I just, you know, like the male body more." By the time he got the final word out, it was a whisper and Dean's face was bright red, the tips of his ears pink.
Rhonda chuckled. "I'm not fishing for compliments hon. I just want you to be comfortable."
Still bright red, Dean managed, "It's fine."
Nodding, Rhonda stood from the bed and undressed, a casual unveiling that was neither clinical nor sexual. Dean liked that this woman was herself no matter what, that she didn't put on masks or do anything to change herself. He could appreciate that, even noted that she was beautiful, curvy in all the right places on a woman and confident in her skin.
As Dean watched, she piled her clothes on the floor and stepped over to the nightstand where she'd earlier placed a few of her supplies. Rhonda picked up the strap-on from the tabletop, Dean's eyes growing wide at the sight. He pushed himself into a seated position, tense against the pillows. Dean hadn't paid Rhonda's supplies any mind until now and though he was still achingly hard, he was suddenly unsure now that he'd seen the toy.
The strap-on was a deep purple, long and realistically ridged with a mushroomed tip on either end. Yeah, he'd fucked himself on his self-made toys before, even been with two male partners by this point, but there was something about being faced with this toy that had him out of sorts.
Rhonda smiled at him, coming to sit on the edge of the bed, resting the toy in her lap. She placed a hand on Dean's thigh, rubbing her thumb over the skin just above his knee. "Dean, hon, it's okay. I know it looks a bit intimidating," she said, lifting the toy and giving it a little shake, "but I promise you it's not that bad." Dean smiled nervously, only one side of his mouth lifting.
Rhonda leaned in and gave him a crooked smile. "You've had cock before Dean. You loved what we were doing earlier. This won't be so different from those things. And Dean," she brought the toy closer to him for him to see better, "remember that one end of this is for me. There's only half of this for you to take. I'll take care of you."
Dean stared at the toy she held in front of him and breathed shakily. Swallowing thickly, he gave a short nod. "Okay."
Rhonda grinned and stood again. "Good. Okay, well I'm going to get this situated, so why don't you give yourself some love while I do that."
Dean blushed bright red again, eyes darting away from her. In his worry and the sudden tension, his erection had waned some, so Dean did what Rhonda said, stroking himself back to full hardness. Unsure if he really wanted to watch or not, Dean shot side-ways glances at Rhonda, watching her as she got herself ready with the toy.
She stepped into the straps until they were just under her hips and then with a little squat to part her legs, lifted one end of the dildo between her lips. Dean swallowed and licked his bottom lip, shifting his eyes away and back again, curious.
Rhonda dropped her head back as she eased the toy inside, groaning softly as it filled her. Adjusting the straps to sit around her waist, Rhonda looked to Dean. "I know this is all a little weird for you. It might be easier if you can't see me when we do this." She climbed back onto the bed, bracing her knees apart on the mattress, purple dick protruding from her groin and looking strange but also enticing.
Dean was suddenly very into this all over again, his need to be filled from earlier in the night returning full force. His hole throbbed and his hips rocked up into his hand. "Fuck," he whispered.
"Go ahead Dean, up on your hands and knees." Dean scrambled up, turning his back to her, settling his palms into the mattress and dropping his head down between his shoulders. Rhonda moved up between his legs and reached out, soothing a hand over his lower back, the other pulling one cheek to the side. She thumbed over his hole and seeming satisfied, pulled her hand away.
A snick echoed in the room and Dean knew that Rhonda was opening the lube again. A finger slicked over his hole and pressed gently inside, easing the way. When Rhonda pulled away again, Dean could hear a slick sliding sound and trembled, recognizing the sound of lube being applied to cock.
Rhonda lightly gripped Dean's hip and with the other hand, positioned the dildo at Dean's entrance. She rubbed the cool tip over his hole. Dean let out a breathy moan, his arms already feeling weaker knowing what was to come. He held his breath, equal parts anxious and excited.
Without further warning, Rhonda shifted her hips forward and the thick plastic cockhead eased its way inside. Dean's breath hissed out of his lungs at the pressure and instant fullness. "Okay?" Rhonda asked, her thumb again rubbing in circles where it rested at the back of his hip.
"Y-yeah," Dean managed, holding perfectly still. At Dean's answer Rhonda continued to press forward, sinking deeper inside at a steady pace. In no time at all the cock was balls deep in his ass and Dean's eyes fluttered closed at the sensation. Finally. Goddamn finally.
Gently, Rhonda pulled back in small increments before rocking in again. Dean's breath caught at each thrust forward, the thick fullness beginning to settle the need he'd felt all night. As he grew more accustomed to the movement and feel of the dildo inside him, Dean began slowly rocking his hips back to meet Rhonda's motions.
One particular thrust backwards of his hips forced a pleasured groan from her mouth. "That's it Dean. Just like that."
They rocked in sync for a short time and then Rhonda surprised him by surging her hips forward and grinding against him. Dean threw his head back on a loud moan. She did it again, and again, and Dean's eyes rolled back as a new angle forced the head of the dildo to graze over his prostate.
Arms too weak to hold him up, Dean dropped to his elbows, his ass lifting higher in the air, again changing the angle. The dildo was now perfectly hitting his prostate every time and it was driving him fucking crazy. He turned his face into the crook of one arm, a sobbed moan muffled into his skin. A breathy punched out "ah" escaped his lips, quickly followed by another with each surge inside, Rhonda's hips now slamming forward on each thrust, her hands clenched tightly around his hips.
Sweat dripped from Dean's hairline and formed a sheen over his back. He felt Rhonda's hands slip over his skin and it somehow only made everything better. He was drowning in pleasure and the feeling of finally being full, so full.
His own toys had stopped cutting it a while ago and it had been so long since he was with someone he thought he'd combust. He'd started to lose hope that he'd get what he needed again, so nervous about being overpowered after how Gavin had been able to manhandle him, how the man from earlier that night had held him immobile.
There wasn't a man behind him, and there wasn't a hot throbbing cock inside him, but he was getting fucked and there was the force of someone's hips behind it. This was far more satisfying than anything he could do to himself.
He whimpered as Rhonda twisted her hips, the drag against his sensitive walls and his prostate sending his pleasure center into overdrive. He didn't know how much more he could take before he fell over the edge. He'd been dangling over it for so long, there wasn't much left of his grip.
"I'm so close," Dean whimpered, the words little more than a whisper. His body rocked with the force of Rhonda's thrusts, back arching, hips rolling, pressing him closer to the cock inside him. It was incredible – long, thick, full.
Face still tucked into his arm, Dean tried to stifle a whine, fingers curling into the comforter. Rhonda was purposely driving her hips forward at the same angle, the dildo brushing his prostate. His skin was flushed hot with pleasure, his skin too warm and beginning to feel oversensitive, prickling and tingling, almost too much for him to handle.
Behind him soft moans spilled from Rhonda. Dean did his best to meet her thrusts, give the pleasure back to her, but from his position, there was only so much he could do. She had the control and fuck, she knew what to do with it.
Rhonda leaned forward, fingers pressed hard into his skin, her hips picking up speed. "Touch yourself hon."
Dean whimpered again into his arm, the new angle even better than the last. Frantic with need, he followed Rhonda's directions, sliding one hand from its hold on the covers to his cock. He pressed his palm against his length, massaging it against his stomach for a moment before wrapping his fingers around it and giving a tug. Slick with pre-come, Dean's hand slid easily over his cock. He was amazed by how wet he'd gotten, even more surprised by how hot he found it. He rocked back against Rhonda and continued jerking his cock, his hand keeping time with her hips.
"So good," he mewled into the comforter, the bubbling heat in his belly about to boil over. Feeling a tingle start low in his spine, Dean slid his hand faster. Rhonda's hips were losing their rhythm and then he felt her shudder over his back, a whimpered groan sounding behind him. Knowing she had let go, Dean allowed himself to fall over the edge, a cry muffled into his arm, vision whiting out.
Dean's hand flew over his cock as his body shook, all of the desire, sensation, and pleasure of the night convalescing into a storm ravaging his body. His hips rolled, continuing to rock him between his palm and the dildo still inside him.
His hand slowed, breaths coming fast, still trembling. He couldn't move, feared that if he did, his body would just shake apart. Behind him he felt Rhonda remove herself from where she had leaned over his back, grazing a hand over his spine as she withdrew her hips, the dildo sliding free of him with one last squelch.
Dean's body shook harder at the sensation, feeling so good but also so suddenly empty. He let himself sink down into the mattress, boneless. "Fuck," he breathed.
Rhonda laughed behind him, the bed shifting under her movement. "Mmm," she seemed to agree with him, "Feelin' pretty good huh?"
Dean could do little more than chuckle back. He was floating. Rhonda let him lay there for a while and then Dean started to notice the drying mess under his belly. He pushed himself onto his knees, brushing a hand over his abdomen. "Shit, sorry 'bout the mess." His cheeks heated.
Rhonda waved a hand at him. "Don't worry about it. You more than made up for it." She gave him a leer. Red rushed to his cheeks again and he ducked away from her gaze.
"Can I help you clean up at all?" Dean climbed off the bed and stood awkwardly next to it. Now that the sex was over, he wasn't exactly sure what to do. This somehow felt different from being at Aaron's or Gavin's.
"Nah, I got it," Rhonda assured him, tugging the comforter from her bed and rolling it into a ball. "The bathroom's across the hall though if you want to clean yourself up. I'm gonna go put this in the wash."
"Yeah, I'll do that." Dean searched the room briefly for his clothes and went to clean up. When he returned, feeling much better without come smeared over his stomach and lube leaking out of his ass, he pulled his clothes back on.
Glancing around the room for any missing items, Dean's eye caught the small pile of pink just to the side of the bed. Checking to see if Rhonda was coming, Dean bent to pick the panties up. They were still damp, but Dean stuffed them into his pocket anyway. As stupid as it was, Dean couldn't resist having the souvenir.
He exited the room and wandered until he found Rhonda. She was just coming out of the laundry room, still naked, seeming completely comfortable. Dean really liked that about her. "I've gotta head out, um, gotta get back to my brother."
Rhonda met his gaze, a half smile quirking her mouth. "It was an absolute pleasure to meet you Dean." It was almost a purr and Dean felt his cheeks turning red once more.
He dropped his gaze to the floor. "You too," Dean replied, "and uh-thank you." He rubbed a hand over the back of his neck.
Rhonda stepped closer, tipping his chin up. "You're more than welcome, hon. I really hope you find what you're looking for, Dean." Dean closed his eyes, swallowing thickly.
"Yeah, me too." Rhonda pulled him into a hug and with a kiss on the cheek, released him, giving his ass a pat as she directed him towards her front door. Dean burst into startled laughter and stepped outside, walking in a slight daze to the Impala.
He slid into the driver's seat and just stared ahead for a few minutes. He grinned, the ache in his ass sharper now that he was sitting. Holy fuck, he hoped that lasted a few days.
AN: So I wanted to work in some canon scenarios of young Dean, and what better way to do that than through Rhonda Hurley? Other authors have written amazing versions of what happened between them and added pegging to the panty-kink. I decided that fit pretty well into what I had here, so there it is. Hope you liked it!