Introduction:
Start of an ongoing series of feminization.
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 up 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.