Samantha's sixteenth birthday came along before she knew it and passed just as quickly. The last six months they had bounced around from one state to another so many times Samantha was feeling whiplash from it and she'd gone to seven different schools since she'd started showing the public the real Samantha. She had met a few good friends along the way and had found it hard to leave the budding friendships she'd started, but she'd always had the most important person in her life right there beside her through it all, making things better with just a teasing smirk and a loving kiss.
Three weeks ago they had settled into an old double-wide trailer on the outskirts of a small town on the border of Kansas and Oklahoma. It was falling apart, having seen it's heyday probably around what felt like the turn of the century, but it was better than most of the skeazy motels they had stayed in over the years, so that was something.
Their dad was away again on a hunt, big surprise there, and they had the place to themselves. They were taking advantage of knowing they were truly alone with dad a state away for the first time in a month. Making out with Dean was always a favorite past-time of Samantha's; her brother lips against hers, enjoying the simple pleasure of kissing for kissing's sake. But Samantha was on a mission and was determined to get her way this time.
"You promised." Samantha whispered. "Don't you want me?"
A strangled laugh erupted from Dean as he pressed Samantha onto her back and crawled on top of her, his eyes roving over the small red scrap of lingerie that covered his girl. He settled his body in between her thighs, fitting perfectly between them like she were made only for him. "Baby, that's not it. I want you so much that sometimes it feels like I'm dying if you're not in my arms. I can't stop dreaming about what it will feel like being inside you, hearing you scream my name as you cum… the way you'll clench tight around my cock and milk me. There's nothing in this world I want more than to be inside of you. I just want to make sure we do it right and that it's something that you won't regret later on."
Rolling her eyes, Samantha flipped Dean onto his back and straddled his lap as she glared down at him, angry fire flashing in her eyes.
"Dean, I love you, you idiot and I am ready. I've been ready for a while now and there's no way I would regret this. You don't think that I've dreamed about it too?" Samantha pressed her bottom down against the hard length of his cock, undulating against it with a smirk on her lips as Dean groaned, his hands clenching around her hips. "I wake up panting from dreams where you hold me down and pound me into the mattress. I feel empty… wanting you inside me… I want to know what it feels like to have your dick stretching me open and you cumming inside me. God, I want it so bad," she moaned.
"I just don't want you to regret this," Dean sighed, looking up at her with concerned eyes. "This is your first time, baby, and it needs to be special."
"You don't think this is special?" She asked. "I'm officially sixteen now and we've waited for two years. We've got the house to ourselves; Dad won't be back for at least a week. I bought pretty new sheets and this gorgeous teddy. I did my makeup and hair special for you and laid out candles… and we love each other. What could be more special than that?"
Giving her brother the biggest puppy dog eyes known to man, Samantha leaned down and ghosted her breath over Dean's lips, her breasts pressed heavily against his bare chest. "Please…" she begged softly, her voice taking on a low husky tone.
Dean's pupils widened and his breath came out in heavy pants, his dick going from half-hard to rock-hard in a second flat. 'Score one for my womanly wiles', Samantha thought, suppressing the giggle that wanted to break free. Samantha had a second to think on her burgeoning 'womanly wiles' before Dean surged up and flipped her over onto her back with a low growl. She gasped, taken a little by surprise and a lot whole lot of lust.
"Sammy, god, baby, so fucking beautiful," Dean moaned as he nuzzled down her body, his lips traveling a familiar path… but this time it would end in a place that they'd both been dreaming of for so long. "Gonna make you scream and moan my name… eat you out until you can't take anymore and then I'm gonna fuck you over and over; make you cum on just my cock, nothing else!"
Samantha whimpered, her mind a puddle of mush and her body on fire. She knew he could do everything he'd said and more. Dean's mouth brushed up against a hard nipple, the warmth of his breath muted by the thin sheer red lace covering it. Not even thirty minutes ago she'd nearly creamed her panties as she looked at herself in the mirror and thought of what Dean would do to her in the sheer teddy and loving the way her body looked so womanly in the lingerie… but now she hated it, hated the fact that it separated her from Dean's mouth, his lips, his tongue, his teeth. She wanted to rip the scrap of material off, without a care for the money she'd scrimped and saved for months to buy it; all she wanted was that hot wet mouth to engulf her and never let go.
Dean was of the same mind, maybe a little more careful than she would have been, as he pulled the teddy off her body with a feverish gleam in his eye. Swooping down, his mouth took one of the hard nubs in his mouth, his teeth biting down on the flesh, making her cry out as sensation overtook her.
"Dean!" She screamed as pleasure sparked through her body and down to her groin, lighting her body on fire. She wrapped her arms and legs around him, her thighs clenching around his waist and squeezing tightly as she whimpered at the feel of his hard dick pressing up against her bottom, wishing that he could just slam home inside her. "I… oh god… please…"
"I know, Baby. I'm gonna take you care of you, make you scream my name a couple of times before I take you." Dean grinned up at her from around the hard nub between his lips, letting his tongue circle the hard flesh and enjoying the moan that slipped from his girl's lips.
Dean turned his attention back to Samantha's breasts, closing his eyes and sucking and laving the nipple with a fevered determination. Samantha whimpered and moaned, squirming under the assault from his mouth as he his teeth grazed the side, biting down softly around it and pulling slightly. It was pleasure and torture and heaven all combined.
Ever since she had started the hormone treatment, her breasts had been sensitive, always verging on the precipice between pleasure and pain. Dean had noticed it from the very beginning and hadn't wasted a chance since to make her cum from just his mouth and hands on her nipples.
One of Dean's hands cupped her other breast, squeezing and massaging the flesh; letting his thumb graze back and forth, back and forth, across the nipple… a startling change in sensation from the harsh bites and sucks being administered to the other. Gripping the sheets in her fists, Samantha closed her eyes and let the pleasure overwhelm her.
"Dean… yes!" She clenched her thighs around his waist, pressing herself as close to him as she could get as she grew closer and closer to orgasm.
Samantha felt her body tightening, her moans becoming a pitiful string of pleas for Dean to stop and keep on going at the same time. She gripped his head, her fingers holding on tight to his hair as her body stiffened and she screamed his name as she came.
"So damn beautiful," Dean whispered as he nuzzled her breasts, giving sweet little kisses here and there as he slowly moved his way up her body.
Opening her eyes, Samantha smiled at Dean up above her and grinned as he kept on moving over her, his body straddling her chest.
"Open up, baby girl," Dean murmured as he pressed the tip of his cock against her lips, seeking entrance inside.
Opening her mouth, Samantha sucked the head into her mouth and groaned at the tangy flavor of Dean that she knew so well. Swirling her tongue around his cock, Samantha began bobbing her head up and down, taking more and more of his length with each pass. The whole time she kept her eyes on him, watching as he looked down at her and groaned, his hips giving involuntary thrusts every so often.
Gripping Dean's hips, she pushed them down against her face a couple of times, letting Dean know what she wanted and he caught on quickly. Dean pressed his hands palm down against the wall in front of him and began thrusting inside her mouth, his cock hitting the back of her throat every time.
Samantha moaned around the thick length, loving the feel of how Dean just shoved his cock down her throat, his eyes glazed over with lust as he stared down at her.
"That's it, baby, just take it" he groaned with a deep shove, "… just take what I give you, Sammy. Such a perfect little cocksucker; my little cocksucker. Baby girl you're so perfect..."
She sucked harder as her brother's words hit her ears, the dirtiness of them making her squirm and moan because they were true. She was his, always had been, she'd take anything and everything he gave her and always want more.
Dean started pounding down into her mouth, his cock choking her and making it hard to breath, but she loved it. Even with tears streaming down her cheeks, she gripped him even tighter and silently begged for more, sucking for all she was worth as his balls started tightening up towards his body as he came closer to coming. Pulling back so that just the head of his cock was inside her mouth, Samantha had just enough time to create a little more suction before Dean came down her throat, big globs of spunk filling her mouth and flowing down into her belly.
Dean's groan filled the quiet room as he shook above her, spilling every drop he had inside of her mouth. After a few moments he crawled back down her body and breathed into her chest, his eyes on her the whole time. Samantha grinned at him, sweat and small drops of cum dribbling down her chin. She wiped the cum off her chin and sucked the fingers into her mouth, savoring the flavor a little bit more.
Dean laughed. "Damn, that mouth of yours is something else, baby girl. Needs to be licensed as a lethal weapon… able to make any man a puddle of goo at any moment."
A giggle spilled out from her lips as she wrapped her arms around Dean's back and held on tight. "Only for you though."
"Damn straight!"
They laid there for a while just enjoying the moment before Dean lifted his head as she began squirming under him. Sucking him off had just made her excited about the big finish and she was ready to go again.
Smirking down at her, Dean began kissing a trail down her body, eliciting moans and whimpers as he paid attention to all the special places he knew would make her melt. Samantha felt Dean lean over the edge of the bed and grab the new tube of lube on the night stand, the sound of the cap opening causing an excited squeak to slip past her lips. Dean laughed lowly and positioned himself on his stomach between her spread legs, his breath ghosting wonderfully over her thighs as he breathed.
Samantha gasped at the cold feel of his lubed finger circling her hole before their body temperatures warmed it up. She could hear Dean's soft laugh as he began pushing the finger inside her, the finger sliding inside to the hilt without any trouble. Dean had been fingering her for a year now and her body was used to the feel of Dean's fingers inside of her.
Leaning down, Dean nuzzled into her inner thigh, nipping the delicate flesh lightly as he thrust his finger in and out of her. Samantha mewed and spread her legs wantonly as she gripped Dean's head, her fingers carding through his hair as she gasped and squirmed at the feel.
"Oh god, Dean… another please, I'm ready!"
Dean quickly pulled out the finger and then shoved two back inside, Samantha's hips shooting off of the bed as he pressed against her prostate and fondled the ball of nerves. Samantha cried out, mumbling nonsense as he worked the fingers in and out, shoving roughly just like he knew she liked and bringing her to peak quickly and then backing off before she tumbled over.
"Sammy, baby, you're so hot like this. My fingers inside of you getting you wet and ready for me," Dean groaned as he nipped her hip and licked the head of her penis with a smirk.
It was odd how much she enjoyed the feel of him licking the head, she often ignored the glaring proof of her wrong gender from day to day, but Dean never did. He told her that as long as she had it, it was a part of her, even if an unwanted part and he was going love it and use it to make her cum until it was gone. When he said things like that Samantha was always amazed that he was really hers, that she'd found someone who knew about every little part of her mind and body, and loved it all unconditionally.
A gasp erupted from Samantha as she was pulled from her thoughts, Dean shoving three fingers inside of her without pause. The stretch and burn of it, made her clench her hands around Dean's head, a low throaty moan filling the room as he thrust back and forth inside her body.
"Okay, I'm ready, Dean… get inside me," Samantha gritted as she thrust down onto those amazing fingers, trying to get them farther inside of her then they had ever gone before, "… please, Dean."
"It's alright, baby girl," Dean soothed as he pulled his fingers from her body and crawled up the length of her until his hips were cradled between her thighs, his cock pressing insistently at her opening. "I'm gonna go slow. Tell me if it hurts, okay?"
Samantha nodded as she wrapped her arms around Dean's neck and waited for him to push inside of her for the first time. She felt the head press firmly against the furled muscle of her hole just before it broke through the entrance and probed inside. The stretch and burn of him pushing inside her felt strange and wonderful at the same time and she couldn't believe that it was finally happening. She'd been dreaming about this for years and finally, finally, he was inside her after so long.
"Dean," Samantha sighed, pulling her brother down further, wanting his weight completely on top of her and holding her down.
"I'm here, baby," Dean murmured as he pressed in further, his hands flat against the bed on either side of her head to keep his upper body from crushing her. "Sammy, god, you're pussy's so tight."
Groaning, Dean leaned down and coaxed Samantha's lips open, sliding his tongue inside her mouth and twisting it around hers, their tongues dancing against each other as Dean continued to slowly push farther and farther inside her. Samantha gasped as he bottomed out inside her, the strange fullness felt oddly right and she wanted to take more, take every part of him inside her until they weren't two people anymore… just one entity, one being.
Flexing her hips, Samantha tried to get Dean to start moving, but she cried out as a sharp sting flared inside her taking her by surprise.
"Don't move, baby girl… you have to get used to me being inside you before I start moving, okay?"
Samantha nodded and tried to make her body relax around him.
"You know I love you, Sammy-girl," Dean whispered against her lips as he ran his hands down her body, tweaking her nipples with a practiced flick of his fingers.
Gasping, she couldn't speak as a spasm of pleasure/pain spiked throughout her body, she clenched down around Dean's cock inside her. Dean groaned at that and gave an involuntary shallow thrust, his hands slipping underneath her body to cup her bottom and lift her lower half up for a better angle.
"I'm ready… please say I'm ready." Samantha whimpered as she clutched around Dean and flexed her hips again, another gasp falling from her lips as Dean's cockhead hit her prostate perfectly.
"Good enough," Dean growled and pulled almost all the way out.
Gripping her bottom tightly, Dean slammed back home inside her and Samantha saw stars. The pleasure was like nothing she'd ever known before and instantly became her new obsession, it felt so good. "Dean!"
"Yeah, baby girl," Dean growled as he pounded in and out of her, slowly getting a rhythm going inside of her "… take it, take what I give you, baby!"
"Ugh, yes!"
"So pretty, Sammy… all mine, always been mine, since Dad put you in my arms," his rhythm grew faster as he thrust, his hands holding her so tight that she'd probably have bruises in the morning. "You'll always be my baby girl, my Sammy!"
Clenching her legs around Dean's waist, Samantha held on as Dean pounded down into her, the feel of him moving inside of her quickly taking her higher and higher with each thrust. This had to be heaven… nothing else would ever feel so good again; Dean inside her, around her and telling her she was his.
Slipping a hand between their bodies, Dean pinched one of her nipples and Samantha exploded into a million tiny little pieces, her body stiffening as she came. "Dean!" Samantha screamed, the sound bursting from her lips as she clenched around him, sending him tumbling over the edge, cumming inside of her. The warmth of his cum filling her was everything she'd thought it would be and more; marking and claiming her like no one else ever would.
Dean slumped down onto her, his head resting on her pillowed chest and his warm breath making her shiver as it met her sweat dampened skin. Dean nuzzled her breasts, licking the wet skin with a quiet groan, his softening cock finally slipping out of her as a trickle of his cum quickly followed. The sensation of it dripping out of her hole felt deliciously obscene and she loved it.
One of Dean's hands slipped down between their bodies and circled her wet dripping hole, pushing in slightly as a squelching sound filled their bedroom. He pulled back a little to look at the sight, his breath hitching, and Samantha grinned.
"Pretty little pussy, leaking my cum," Dean whispered as he crawled down her body and settled between her thighs, face pressed close to her groin.
Samantha gasped as she felt Dean's tongue lap at her hole, licking away the slowly dribbling cum as it leaked out of her body, his moans and slurps filling the quiet room. She closed her eyes and squirmed under the assault, her body tingling with a slowly building renewed interest and need. Allowing her fingers to thread through Dean's hair, Samantha laid back and just enjoyed Dean's undivided attention for as long as she could.
Finally, Dean wandered up her body and sighed against her breast before lifting his head and looking up at her. "Goddamn, baby girl, so beautiful… No regrets?"
"Not a one, Dean… it was perfect." Samantha laughed as she threaded her fingers through his hair and gently pressed his head back down onto her breast and closing her eyes, enjoying the afterglow of her official first time with Dean. "Love you, Dean."
"Love you too, baby girl."