Femboy Anal Training Novels & Stories

Stavros' P.O.V. Even though training wasn’t scheduled for today, Analina still wanted to go down to the gym. She walks into the gym wearing a black sports bra with a zipper in front and matching spandex pants. I walked up to her and pull her to me by her waist. “Oh, my love.” I say to her as I leaned in to capture her lips with mine. After separating from the kiss, she asked me. “What about training?” “Cancelled!” Is all I say as I pull the zipper down from her sports bra and exposing her huge breasts. I slip it off her arms and take her full breasts in to my hands and fondle them fiercely, playing with her nipples I pull squeeze and pinch them just so that I can hear her groan and moan in p

Finally, he’d fucking mate her until she couldn’t find her way free of him. “Good little girl. Now, you’re going to enjoy this again. I won’t stop until you’ve orgasmed again. Can you do that for Daddy? Fuck my fingers until you cum again.” This was all part of her training. He wouldn’t share her with anyone else, but he didn’t want her modesty to impede her pleasure. Her hands were on his upper arms, grasping them hard as she panted in his ear. She couldn’t speak anymore but moaned instead as she now worked his fingers into her core.

“Back straighter. Head upand tits out. You’re not some pathetic whore anymore—you’re prize stock. Show it.” She tried. The plug shifted inside her with every crawl, pressing against places that made her pussy clench and drip onto the floor. Drool ran down her chin from the bit. Her face burned with humiliation, but her cunt was soaked, clit throbbing against the cool air. Damien led her around the training ring like that for what felt like hours. Whip cracks punctuated every mistake. When she slowed, the crop licked her tits until they were striped red. When her back dipped, he kicked her legs wider and lashed the sensitive skin where thigh met ass.

“That’s it. Use those hips. You’ve got real power here, Bella. Thick and strong. Don’t fight it.” His voice had dropped lower, rougher than before. Deeper. It sent a shiver straight through me. I pushed up, feeling his grip tighten. Sweat started dripping down my back, making my top stick to my skin. Another rep. His thumbs pressed into the flesh just above my ass. Firm. Commanding. “You’re doing so good,” he murmured right by my ear. “Most women with your curves hide. You? You’re starting to own it. Look at how your body moves for me.”

She was trembling, right on the edge, when they heard the sound of voices in the hallway outside the studio — two other trainers finishing their sessions and chatting. Damien didn’t pull his fingers out. He kept thrusting them deep and slow while they both listened. The voices faded. The second they were gone, Damien pulled his fingers out, breathing hard. He stroked himself furiously and came with a low groan, hot thick ropes of cum splashing across her stomach, her breasts, and her open mouth. He used his fingers to push some of the warm cum inside her pussy, rubbing it over her clit until she whimpered. “Keep me inside you for the rest of the session,” he ordered, voice dark with possessi

When she finally came out, she no longer had that pitiful, calculating demeanor she had before. Instead, she started trailing after me, always going "Lucille this, Lucille that". She dressed it up nicely, saying she wanted to learn from me and strive to transform herself into the heroine of a female empowerment story. I didn't really care either way. After all, no matter how much she studied, she'd never be smarter than me. Emery and Logan, however, were less than thrilled. As soon as I wrapped up a project, they whisked me away for a getaway under the cover of the night.

Her fingers finally pushed inside my hole -two of them, thick and relentless, curling against the spot that made my vision white out. Her other finger stayed on my clit, rubbing hard and fast. Then she shifted lower, one slick fingertip circling my asshole while she fucked my pussy. “Tight little hole,” she murmured, pressing just enough to make me gasp. “We’ll train your pussy, you’ll be begging like a whore for it by the end of the night.” I was shaking. "Oh.....oh...fuck...fuck....oh...." I moaned loudly, mouth open. Mona’s fingers pumped deeper, the wet sounds obscene in the quiet room. She rubbed my asshole roughly in tune with her thrusts.

periods, walking around the room with it inside while he trained her to crawl, kneel, and present herself properly. One afternoon he brought in a fucking machine. The thick dildo attachment was already slick. He strapped her down on a bench, ass up, and set it to pound her hole on medium speed. Then he sat in front of her and fed her his cock while the machine reamed her ass. “Take it all,” he said, voice rough. “You’re gonna learn to cum from your ass like a good pet.” She did. The constant pounding on her prostate-like spot mixed with the humiliation finally pushed her over. She came hard, shaking, drooling around his cock. Diego groaned and filled her mouth.

Alex joined for one final watching session in our soon-to-be-lost apartment, heightening the nostalgic filth. New elements pushed boundaries: light breath play during orgasms, extensive anal fisting training leading to his cock and a toy simultaneously, food insertion with bananas and cream eaten out of both holes. I was a non-stop squirting, cum-dripping wreck, gaping pussy and asshole, body covered in marks, face and tits painted white multiple times. We filmed more private videos, capturing the raw intensity for future use during separation.

Ryan swallowed every drop she squirted, groaning into her, then pushed her off and made her clean both their cocks with her mouth until they were shiny again. Anal training came next. Marcus pulled out a thick, ridged silicone plug with a vibrating base. “This is your new ass. You’re going to take it every single day now. No turning back.” He lubed her generously and pressed the head against her tight ring. Emma whimpered, already sore from the hours of cock and tongue. But she pushed back against it, needing it, needing them. “Tell us how much you need this,” Marcus said, voice low. “I need your cock in my ass. I need it to own me.”