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.
