Femboy Anal Training Novels & Stories

He might be a slut, but he was a responsible one. Taking a shower and cleaning his insides thoroughly, Joe made sure to increase the enema. He wanted everything clean from his rectum to the ends of his large intestines if it were possible. He wasn’t ready for that inflatable toy yet and decided it could be a good opportunity to train his ass more with the anal beads. Calibrating the anal beads with the inflatable plug inside Joe sounded synonymous with death. His ass would rip, and no surgeon could put him back together after.

So quiet. "Promise." Isabella watched. "One hour. Then we begin." --- 7 PM. The training room. The girl sat on the bed. Already shaking. Isabella held up the dildo. Thicker than yesterday. Maybe two inches in diameter. Closer to actual size. The girl stared at it. Breathing rapid. "I can't," she whispered. "That's too—I can't—" "You can," Isabella said firmly. "Because you're stronger than you think. And because you survived last night. You can survive this."

Her tongue slid in my mouth, her hands gripped my ass. "I'm going to have fun training you, having your body, watching all the men and women using you, fucking you, humilliating you. Ummm, and we're going to love watching horses dildo fuck you, their big cocks pounding this well-used cunt of yours," she said as she ran her hands over my cunt, then my red sore ass cheeks, then gave them a slap. "I think I'm going to have fun being trained," I replied and laughed. "Looks as though I'll have to use the whip and paddle on you alot as well. Whip this lovely cunt as we hold your legs apart. See you soon," she said as she rubbed and fingered my clit. I moaned out loud. She laughed and left.

The training went on for hours. They fucked me in every combination: One in my pussy, one in my mouth, one playing with the plug in my ass. They made me ride Luca while Matteo fucked my face and Nico worked the next larger plug into my ass. They bent me over the edge of the bed and took turns pounding my pussy while the plug stayed locked inside me, making me feel impossibly full. Every time I came they praised me. “Good little kidnapped slut.” “Taking training so well.” “Your holes are getting greedy for us.”

“I’m so full… I need you inside me.” “Not yet.” His smile was dark and promising. He spent the next hour training her—making her hold positions while the toys tormented her, teaching her proper kneeling posture, and rewarding her with his fingers or mouth when she pleased him. He edged her twice, bringing her right to the brink before turning the vibrator off, leaving her a dripping, whimpering mess.

"Just being the common fuckboy, babe." "Good morning, students! Are we ready to read some papers?" There was a loud, collective sound of groans, making the teacher laugh. He chose two people to go first, giving everyone else hope that they wouldn't have to read today. As the one person started to read aloud the biography of their partner, Connor chose to continue his fuckboy act. He placed his hand on my thigh, which resulted in me pushing his arm away. Then he went on to scoot his chair closer to mine, and I figured if I did something about this, I'd get in trouble.

“Are you ok with that? I can assure you I’m clean. I send my test results to the agency regularly.” I know that’s part of their criteria, so I nod. “Yes, Sir. That’s fine.” He takes out a big bottle of lube from the drawer. “Don’t look so worried,” he says, “I know what I’m doing.” “Thank you, Sir.” I hope he fucking does. “Ever had an anal orgasm?” he asks, fisting his monster. I’m honest. “Yes, Sir. I love anal.” “I can assure you this is going to be better than you’ve ever had before.”

Her voice echoed through the living room. They took turns for over an hour, eventually moving into double anal training. Both massive cocks stretched her ruined hole obscenely wide at the same time while she screamed and drooled onto the carpet. The pain and pleasure mixed until she couldn’t tell them apart. They made her cum twice from anal alone, something she’d never experienced before. By the end, her ass was gaping wide open, bright red, and leaking their thick cum in heavy streams down her thighs. They finished by covering her back and ass cheeks with fresh, hot loads, marking her completely.