Fuckhole's Enslavement

Disclaimer: Everyone is 18+, plus the usual trans people are cool I'm just t4t and horny

Phin awoke groggily in a bed that wasn't his own, chained up in a dark room only lit by a single dim yellow-ish lightbulb hanging from the ceiling. He looked around frantically, was this a nightmare? It seemed to be a basement; gray bricks on the walls, sound proofing, and... Were those whips? Collars? More chains? He instinctively went to squeeze his legs together but he found they were kept apart by a spreader bar on his ankles. In fact, he was completely naked, hips raised on a pillow, and his bare pussy on display. He felt cool air on his sensitive bits, as he tugged against the restraints holding him there.

"Look who's finally awake." A voice sounded from a shadow in the room. A voice Phin recognized.

"Penelope?!" He shouted. "Penelope, is that you?! What the fuck are you doing?!"

Penelope was Phin's estranged sister. She became something of a "glass sister" after Phin was born; him taking all the attention. One day, she cut contact with the whole family, and Phin reached out to talk to her, to apologize, to say her family missed her. She didn't respond; then.

"Ah ah ah." She stepped out from the shadows. She was wearing a latex bodysuit, tight against her perky breasts. The fly was undone, Phin betrayed himself and looked. Her cock was semi-hard, and still big. "That's 'Mistress' to you, Fuckhole."

"Penelope- What are you doing?!" Phin cried. "I'm not a fuckhole- what are you doing?!"

"Oh, that won't do..." Penelope went to a hanging shelf, picking up what looked like a whip, walking back to the bed where he was. "What's my name? I told you, you best remember, you dumb slut."

"I'm not a dum- Ah!" Phin cried out as she struck him on the stomach with the whip. He felt tears prick his eyes, swinging his head from side to side. "Stop!"

"Say my name!" She shouted, striking him again, this time, directly on his sensitive nipple, which had regained sensation after his surgery. Phin screamed, crying fully now, tears streaming down his face. The whip burned, his body was so hot from it. She whipped him again, twice on his thighs for good measure as he wailed.

"Big sis, please!" He cried, struggling against the bonds. This time, she whipped him directly on his little tdick. He shrieked, eyes burning from his own tears.

"Say my name, Fuckhole." She said darkly, setting the whip down on the bed and toying with his little cock. Phin whined loudly from the pain and the sensitivity.

"Yes... Mistress..." He sniffled.

"Good boy!" Mistress beamed. "Very good boy!" She pushed two fingers into his cunt, drawing a gasp from the boy on the bed. "You're so wet just from being whipped... I know you so well."

"Pl-please... Please no more..." Phin pleaded, looking at her with big wet eyes. Mistress instead crawled on top of him, straddling his face, rubbing her hardening dick on his face, as he looked at her with wide eyes.

"I saw your Tumblr, by the way..." She wiped his tears with her cockhead. "You're a little slut, Fuckhole, y'know that?"

"Not... Not for you..." He sobbed again, feeling the hot marks across his body and the reality of just how helpless he was to his older sister raping him began to set in.

"I'll make you be. You kept posting about being kidnapped by an 'evil woman'.... Well, here I am." Mistress laughed, spitting on his face and her own girldick. She pushed the head against his lips, lubed up with her spit and his own tears. "Open."

Phin kept his lips clamped shut, shaking his head defiantly. "I can't... I can't! She'll only want more..." He thought, but he knew full well she'd take more no matter what, as she continued to press her big cock against his mouth.

"Be a good slave, or I'll whip you again." She warned. The word "slave" set him off; did she mean she'd keep him forever? Phin went to protest, but she shoved her meat in his mouth before he even got more than a sob out.

She thrust into his mouth then, filling it up. She didn't even bother to warm up his throat, instead just slamming against and into it. Her hips hit his face roughly as she took his mouth, filling his nostrils with her scent and his tongue with her taste. His tears only made it more slippery as she used him.

"Fuck, good boy, good fucking boy... Run that tongue across me, yes..." Mistress moaned as she fucked his mouth.

In his fantasies, getting his mouth used by a captor was much sweeter than this. He'd imagined they'd treat him nicer; he supposed it was unrealistic, but it was a fantasy! It wasn't meant to happen to him in real life, beyond roleplay with a girlfriend who loved him, of course. But still, even getting his mouth and throat used against his will made his pussy and clit-dick throb as he humped the air pitifully.

She suddenly slowed, pushing all the way down his throat and holding it there. Phin gagged on her length and tried to push away, but he had no room or freedom to do anything besides take it. He looked up at her with teary eyes, in a silent plea for her to get off, but she held him there anyway. He felt himself start to get dizzy, before she pulled off and began roughly fucking his mouth again, all while he sobbed and tried to get more oxygen in. It felt like he was drowning on her cock as she used him mercilessly.

"Is she going to kill me?" He thought as he tried to make protests around her thrusting girlcock, but it didn't come out as anything besides moans and squeaks around her shaft.

Finally, she pulled out, rubbing her meat all over his face, getting his red and tear-stricken face all wet with her precum and his saliva and tears. Phin gasped for air between sobs as she violated him.

"Your name is Fuckhole." Mistress said, sweetly stroking his face as if she didn't just nearly suffocate him on her dick. "Tell me your name."

Phin took in a shuddering breath, and stopped himself from forming a protest. "She'll only hurt me more..." He couldn't get his face fucked that intensely again. Or whipped. Even though a part of him knew she'd do it again tomorrow, maybe even forever, just to hurt him.

"Fuckhole... My name is... Fuckhole..." He whispered defeatedly.

"Good slut." Mistress moved down the bed to sit beside the spreader bar, lifting his legs up over her shoulders. "You wanna make me a baby?" She rubbed her cockhead against his wet slit.

Phin's heart froze. His stomach sank. He couldn't get pregnant! Not by her! Not like this!

"Wh-what? No! You can't! Please!" Even still, he moaned as she rubbed the head of her dick against his tdick, stimulating the sensitive nerves there.

"Aw, come on, you're so wet for it..." She was right. Phin was soaking wet at this whole ordeal. But he couldn't! He didn't WANT to!

"No! Please! Get a condom, please!" Phin began to struggle again, but she held him down.

"Shut up, you stupid boy, it's going in!" And that was the only warning she gave as she impaled him on her bare cock, making him scream as she took him. "Fuck, you're so tight..." She moaned as she picked up the pace, thrusting in and out of his wet hole.

"Uhhh, no! Please no mo-Uhmmmm!" Phin moaned as she pounded into him. She gave him no foreplay or time to adjust to her big cock fucking him. Even though he cried and begged her to stop between his slutty moans, he felt his orgasm fast approaching. She held onto his hips and fucked him up and down onto her cock as he came on it, his pussy clenching around her. "Fuck- No! I'm cumming- No!" He still moaned through his protests, gasping and biting his lip.

"Good boy, cum for me. You're just dying to milk my cock inside you, aren't you? Get pregnant for me?" His Mistress taunted him as she thrusted in and out of him, his pussy making obscene noises on her cock as she took him.

"Fuck- Uhmmm- No! Please! Uhhh-" He moaned, tears free falling from his eyes as he tried to struggle, but she held him in place and he felt weak and dizzy.

"Oh, you sound so convincing right now, you stupid slut." She grunted sarcastically. Phin didn't respond, making little "ah- ah- ah-" noises as she pounded him. "Close again? I'll make you cum so much~"

"AHHH-" Phin screamed as he came again, wailing. "I can't take much more of this..."

"And that's just the beginning." She moved one hand to his throat, gripping it. "I'm gonna keep you forever, Fuckhole..." She threatened, and before he could protest, she leaned down and kissed him, shoving her tongue in his mouth.

"She can't..." He thought as he came again, his screams muffled by his big sister's tongue exploring his mouth. She pulled off, gripping his hips again.

"You're just my stupid little boytoy now, and you fucking love it~" She taunted. "And I'm going to get you so pregnant~"

Phin couldn't even protest anymore, just moaning obscenely as she had her way with him. He lost count of how many times he was being made to cum anymore, just making little "ah- ah- ah-" noises and looking at her with tears in his eyes.

"I'm her slave..." He thought, letting his head fall back limply as he cried out. She kept pounding into him, fucking orgasm after orgasm out of his weak pathetic little body.

"I'm hers to use..." He felt her hips ground against his little tcock as she took him, drawing whines and groans from him.

"I'm hers to abuse..." He felt the tingles of the whip lashings still. On his nipple, on his tummy, on his thick thighs that tried to clench but were forcibly spread apart. His throat felt raw from screaming and being forced to take her cock all the way down. His eyes welled up with tears again as he sobbed between his moans.

"I'm hers to breed..." He felt her thrust in and out, he knew she had to cum at some point. And it'd be inside him. And he'd one day carry her child, or even children. No matter how much he screamed, no matter how much he cried, no matter how much he tried to run.

"Fuck, I'm gonna cum soon, lil bro." She hissed through her teeth as she slapped his thigh with her hand a couple times, drawing a yelp from him. "Get ready for it~"

"Fuck... Ah-" He came again, but didn't even have the energy to scream or struggle anymore. He looked at her with big eyes, silently pleading at her to let him go. Instead, she leaned into him, looking into his eyes.

"I'm going to knock you up, Fuckhole." She hissed.

"No..." He whined, but his eyelids fluttered as he came again.

"Fuck!" She shouted, thrusting into him one more time, and holding her hips there. Her cock erupted into his cunt, sensitive from the rough fucking. Phin cried out defeatedly as he felt her cock twitch as she came in him, sobbing again.

"Fuck..." She whispered, panting. She held her cock inside him, twitching. "Good boy, make sure it takes." She commanded.

"Fuck, I... I hate you..." He whimpered pitifully, tears streaming from his face.

"You'll learn to love this." She whispered, licking his tears from his cheeks. She kissed him again, softly this time. Her cock was still inside him, twitching, and making him moan with fullness. "You'll learn to love me, too."

She pushed in and out a few times, just a couple, before pulling out. She sat and watched the cum leak from his pussy, dipping her fingers in to push it back in.

She zipped up her soft wet cock back into the latex, getting off the bed. "I'm going to bring you dinner and unchain you. If you try to run..." She looked at him with an evil glint in her eyes.

"I understand, Mistress..." Phin lowered his head defeatedly.

"Good boy, I'll be right back." She got off the bed, walking up the stairs.

Fuckhole had lived here and served his Mistress for quite some time now. He didn't know how long; she didn't allow him to count the days, and now he'd lost count.

He had freedom in the house now, he slept in her bed with her, and served her in more domestic ways; and sex, of course. How could he forget? He had his head between her legs right now as she worked at her desk, bobbing up and down on her thick erection.

He had a baby bump now. He didn't get pregnant the first time, he didn't think; but at some point, he did. He didn't know the gender. His Mistress took him to his fertility appointments and all, a dutiful "wife" to him. None of the nurses or doctors knew their relation besides being together, or that she had kidnapped him.

Still, she was right. He had learned to love this. And her.

"Fuck, good boy." She moaned, petting his head. She was much kinder to him now that he was properly broken in. Still, sometimes he caused a fuss just to get beaten a little bit, just for the fun of it. Her hands felt so good no matter what she was doing. Fuck, and that cock. It still drove him just as crazy as it did the first time.

"I'm having some girl friends over after work. Will you be good and let them use you?" Mistress asked. There was only one answer he was allowed to give.

"Yes ma'am." He said as he lifted up off her dick. He knew these friends; they didn't know the truth, either. Neither of them told them. He didn't care, he loved his life now. She jerked her cock a little, cumming on his face and chest. He wasn't allowed to wear clothes, still, unless they went out. When they did, she dressed him up in short shorts and tight shirts, just the way she liked her little boytoy.

"Good slave, they'll make good use of you." His mistress teased. He felt a shot of arousal go straight to his tdick. Only she was allowed to use his pussy, though. They could use his mouth or ass as much and as hard as they wanted, but only his Mistress was allowed to use his pussy.

"I love you, Fuckhole." She said, petting his head softly.

"I love you too, Mistress."