Personalised Story: The Shemale Trainer: Part 2 (Patreon)

Matt remained frozen in place, his entire body locked rigid as Marina’s piercing eyes roamed over him without mercy. The glossy black latex dress clung to her tall frame, accentuating every curve of her big tits and thick ass, while he stood exposed in the skimpy French maid outfit.

His blonde wig framed his heavily made-up face, silicone breasts pushing against the low neckline, stockings stretched over his smooth legs, and the tiny skirt barely covering the damp pink thong that outlined his stiff cock.

Heat flooded his cheeks, spreading down his neck and chest in a deep crimson flush that he couldn’t control. His throat tightened completely, words refusing to form as his older crush—the woman he had secretly ogled for months—stood right there witnessing everything.

Oh god, this can’t be happening. My secret is out. She knows. Marina of all people knows I’m a sissy who dresses like this. The one woman whose ass and tits I stare at every day in the elevator, the one who makes me feel so turned on just by existing—she’s seeing me as a blonde bimbo maid with fake breasts and makeup I didn’t even remove properly. My life is over. She’ll tell everyone. She’ll laugh at me. But fuck, why is my cock throbbing so hard right now?

His legs shook violently in the tall heels, knees wobbling as he struggled to stay upright. Every breath came shallow and quick, his heart hammering against his ribs while anxiety spiraled through his mind in frantic loops.

She noticed the makeup in the elevator. She saw the thong when I bent over. She knows I’m not just curious—she knows I go all the way like this. Transformed completely. Wig, earrings, stockings, the whole slutty look. And now she’s here in my apartment, latex dress creaking as she moves, and I’m completely at her mercy.

Marina’s lips curved into a slow, teasing smile as she stepped closer, the latex stretching tight over her body.

“You look absolutely adorable like this,” she said, her voice low and playful. “I spotted the concealer and foundation you missed around your jawline back in the elevator, and that hint of eyeshadow still on your lids. When you bent down for my bag, that pink thong peeked out so perfectly. But this full transformation?” She gestured at the wig, fake breasts, and maid outfit. “I never expected you’d become such a complete little sissy maid for me.”

Matt’s blush intensified, his mind racing with panicked thoughts. She’s teasing me about it. She knows exactly what I am now. My crush knows I’m a crossdressing slut who gets off on this humiliation. What if she makes me do more? What if she tells the building? But the way she’s looking at me… it’s like she wants to play with her new toy.

His legs continued trembling as Marina moved to the couch, the black latex dress hugging her shapely ass when she sat down. She patted the cushion beside her with a commanding gesture. “Come sit down, sweetheart. We have so much to talk about now that your little secret is out.”

Matt’s knees nearly buckled as he shuffled toward the couch, each step in the tall heels sending a fresh wave of humiliation through him. The tiny maid skirt rode up with every movement, exposing the damp pink thong that barely contained his stiff cock.

His silicone breasts jiggled inside the low-cut top, the straps of the matching bra digging into his shoulders.

He could feel Marina’s eyes devouring every inch of him—the blonde wig, the heavy makeup, the stockings stretched over his smooth legs. She’s seeing all of it. My older crush, the woman whose thick ass and big tits I’ve stared at for months, is watching me dressed like a complete sissy slut. She knows I wear this. She knows I get hard from it. My secret belongs to her now.

He sank down beside her, the couch cushion dipping under his weight. His hands fluttered uselessly in his lap, trying and failing to tug the skirt lower. Words refused to form. His throat worked silently, lips parting but producing nothing but shaky breaths. The fire alarm had stopped, leaving the apartment in thick silence broken only by the creak of Marina’s black latex dress as she shifted closer.

She’s so close. I can smell her perfume. Her latex is stretched tight over those curves I’ve fantasized about. And here I am, a 20-year-old guy in full bimbo maid mode, fake tits pushed up, makeup caked on, thong soaked. She’s nearly twenty years older and she’s looking at me like I’m her new toy.

Marina’s gaze lingered on his trembling form, her lips curving into that slow, teasing smile. She crossed her legs, the latex groaning softly. “Look at you,” she murmured, voice low and warm.

“Sitting here all dressed up like the perfect little sissy maid. I have to say, it suits you far better than I expected. That blonde wig, those big fake breasts, the way the skirt barely covers anything… you’ve clearly been practicing this. Embracing this side of yourself is good, sweetheart. Really good. There’s nothing to be embarrassed about.”

Her hand reached out, fingers brushing lightly over his stockinged thigh. Matt’s breath hitched, but he still couldn’t speak. His mind spun wildly. She’s touching me. Telling me it’s okay. My crush is encouraging me to be this feminized slut. I should be mortified beyond repair, but my cock is throbbing so hard it hurts.

Marina leaned in, her eyes sparkling with amusement and something hotter. “I saw how you looked at me in the elevator, Matt. Those glances at my ass, my tits, my lips. It made me feel desired. And now here you are, transformed completely for me. The makeup you tried to scrub off, the pink thong peeking out when you bent over… I knew there was more to you. And seeing you like this? It’s exciting. You don’t need to hide anymore. This is who you are, and it’s perfectly fine to let it out.”

She shifted again, the movement making her latex dress ride higher on her own thighs. Beneath the tight material, her panties were soaked, her pussy slick with arousal at the sight of the petite, heavily feminized young man frozen beside her.

His deer-in-the-headlights expression, the way his legs shook in the heels, the visible outline of his cock in the damp thong—it all sent a fresh rush of wetness between her legs. She pressed her thighs together subtly, savoring the heat building there while she continued talking in that calm, dominant tone.

“You look adorable trembling like that,” she went on, her fingers tracing a slow circle on his thigh. “The stockings, the heels, the way those fake breasts sit so perfectly… you’ve gone all the way. That’s brave. Most guys your age wouldn’t dare. But you did, and now your secret is out with me. I think that’s a good thing. It means we can explore this together. No need to feel ashamed. You’re embracing your feminine side, and it’s turning you on, isn’t it? I can see it.”

Matt’s face burned hotter. He wanted to speak, to deny or explain or beg, but nothing came out. His thoughts raced faster. She knows I’m hard. She knows this humiliation is making me leak into the thong. My older crush is wet because of how I look right now. She’s telling me it’s good that I’m a sissy maid. I can’t even form words. I’m completely hers in this moment.

Marina’s smile deepened as she watched his silent struggle. Her free hand rested on the back of the couch, close enough that he could feel the warmth of her body. “Don’t worry about talking right now,” she said softly.

“Just sit here with me and let it sink in. Your secret is safe with me, and more than that—it’s something I like. Seeing you like this, all feminized and submissive… it’s quite the turn-on for both of us, I think.”

She let the words hang in the air, her eyes roaming over his made-up face, the jiggling silicone breasts, the tiny skirt that failed to hide his arousal. Matt remained frozen, legs shaking, mind a whirlwind of panic and unwanted excitement, unable to do anything but listen as his older crush gently encouraged the very thing that left him exposed and utterly humiliated.

Marina's fingers stayed on his thigh, tracing slow circles over the sheer stocking as she leaned closer, her latex dress creaking with each shift. Her eyes dropped deliberately to the front of his tiny maid skirt, where the damp pink thong outlined his stiff cock. A soft, knowing laugh escaped her lips.

"Your cock isn't locked up?" she asked, voice low and teasing. "Why not? I thought that was internal to being a sissy maid. And your ass isn't plugged either? How does a little thing like you even call yourself properly dressed without those?"

Matt's throat worked. His lips parted but only a faint, broken sound came out at first. He sat frozen, silicone breasts rising and falling fast, the heavy makeup making his wide eyes look even more startled. Finally a whisper slipped free, barely audible. "I... I never had a keyholder."

Marina's smile widened. She let the silence stretch, watching him squirm in the heels, the skirt riding higher with every nervous twitch of his legs. Her free hand moved to his chin, lifting it so he had to meet her gaze.

"You do now," she said simply.

The words landed like a brand. Matt's cock twitched visibly inside the thong, a fresh bead of precum soaking through the thin fabric. His mind raced. She just claimed me. My older crush, the woman I've jerked off thinking about, is telling me she's my keyholder. I'm sitting here in full sissy maid mode, fake tits out, makeup caked on, and she wants my cock locked and my ass plugged. I can't even speak properly. I'm hers.

Marina's hand slid higher on his thigh, stopping just short of the skirt hem. She pressed her own thighs together, feeling the slick heat between her legs grow stronger at the sight of him—petite, feminized, trembling, completely exposed. The black latex hugged her curves tightly, her big tits straining against the material, her thick ass shifting on the couch as she enjoyed every second of his humiliation.

"We'll fix that right away," she continued, tone calm and dominant. "A proper sissy maid doesn't walk around with a free cock. And that tight little hole of yours needs something filling it. Don't worry, sweetheart. I'll take care of everything. You just sit there looking pretty while I decide how we're going to lock you up and plug you."

She let her fingers drift closer to the bulge in his thong, not quite touching, just hovering. Matt stayed silent, legs shaking, unable to form another word. His thoughts spun faster. She's wet because of this. Because I'm dressed like this. Because I'm not locked or plugged. She's going to change that. I'm going to be her locked, plugged sissy maid.

Marina's eyes sparkled with satisfaction as she watched him. She shifted again, the latex dress riding up her thighs, revealing more smooth skin. Her panties were soaked through, her pussy throbbing with arousal at the power she held over the 20-year-old feminized boy beside her. She kept talking in that steady, teasing voice, describing exactly what she planned to do with his cock and ass, while he sat frozen, unable to do anything but listen and leak into his thong.

Marina rose from the couch with a fluid motion, the black latex dress clinging to every curve as it creaked softly. She smoothed the material over her thick thighs and looked down at the trembling sissy maid still seated beside her. "I've been involved in BDSM for years," she said, her voice calm and matter-of-fact. "Do you know what that is?"

Matt's painted lips parted. He gave a small, shaky nod, eyes wide behind the heavy layers of makeup.

She extended her hand. "Good. Then you understand what happens next." Her fingers closed around his smaller, softer ones and she pulled him upright onto his heels. The sudden shift made the tiny maid skirt ride up, flashing the damp pink thong and the stiff outline of his cock. "It's time to lock that cock up and plug that ass right now."

Heat flooded Matt's face. His throat worked as he tried to speak, voice cracking. "I... I..."

Marina pressed a single finger to his glossy lips, silencing him instantly. "The correct response to what I say is 'Yes, Mistress.'"

He swallowed hard, the words barely audible. "Yes, Mistress."

A satisfied smile curved her mouth. She kept hold of his hand and turned toward the apartment door. "Follow me."

Matt's heart slammed against his ribs as she opened the door and stepped into the hallway, tugging him along behind her. The corridor lights felt blinding. Every step in the tall heels sent a sharp click echoing off the walls.

His blonde wig swayed with each movement, the French maid outfit barely covering anything. The short skirt bounced with his stride, constantly threatening to flip up and expose the soaked thong. Silicone breasts jiggled inside the low-cut top, the fake cleavage on full display. Stockings whispered against each other while the heels forced his hips to sway in an unmistakably feminine way.

Oh god, oh god, someone could open their door any second. I'm dressed like this—full makeup, wig, maid outfit, everything. If anyone sees me they'll know exactly what I am. They'll see my cock straining in this thong. They'll see the fake tits. I'm going to die of embarrassment.

Marina walked with confident strides, her latex dress hugging her big ass and making soft, sticky sounds with every step. She glanced back once, clearly enjoying the sight of him struggling to keep up while trying to tug the skirt lower with his free hand. "The cage and plug are in my apartment," she said casually, as if they were discussing groceries. "We'll have you properly locked and filled in no time."

They reached the elevator. She pressed the button and the doors slid open with a ding that sounded far too loud. Matt's stomach dropped as she pulled him inside. The mirrored walls reflected his feminized form from every angle—blonde hair, heavy eye shadow, glossy lips, the ridiculous little maid dress, the visible bulge in the thong. He tried to stand with his back to the mirrors but there was nowhere to hide.

Please don't stop on another floor. Please don't let anyone get on. My heart is pounding so hard. My cock is leaking again. If the doors open and someone sees me like this I'll never recover.

Marina stood close, one hand still holding his, the other resting lightly on his lower back just above the thong waistband. She leaned in, her breath warm against his ear. "You're shaking, sweetheart. Is it the thought of someone catching you? Or the thought of me locking that little cock away?"

The elevator began its ascent. Each floor number lighting up felt like a countdown to further exposure. Matt's knees felt weak in the heels. The damp thong clung uncomfortably, the fabric rubbing against his sensitive skin with every tiny shift of his hips. A fresh bead of precum soaked through, darkening the pink material even more.

When the doors finally opened on her floor, Marina led him out without hesitation. The hallway here looked identical to his own—long, quiet, lined with closed doors that could open at any moment. His heels clicked loudly on the tile. The short skirt continued its teasing bounce, flashing glimpses of his ass and the thong string between his cheeks. Every step made the silicone breasts shift and bounce, the bra straps digging into his shoulders.

This is insane. I'm walking through the building dressed like a sissy maid. Anyone could come out right now. A neighbor. The maintenance guy. Anyone. They'd see the makeup, the wig, the outfit. They'd see how hard my cock is. They'd know I'm not a real girl. I'm so fucking exposed.

Marina stopped in front of her door and fished out her keys with deliberate slowness, letting him stand there in the open hallway even longer. She turned the lock, pushed the door open, and finally guided him inside. The moment the door closed behind them, the tension in the air shifted but didn't disappear. Matt stood just inside her apartment, breathing fast, cheeks burning crimson beneath the makeup, waiting for whatever came next while the memory of every step in that hallway burned in his mind.

Marina released his hand and turned to face him, her expression equal parts amused and aroused. "There. Safe inside. For now." She let her gaze travel slowly over his trembling form. "But we're just getting started, little maid."

Marina guided Matt deeper into her apartment, the heavy door clicking shut behind them and sealing away the risk of the hallway. Her luxurious space opened up with polished hardwood floors, soft recessed lighting, and a large leather sofa positioned in front of a wide window overlooking the city lights.

She led him straight to it, her hand still firm around his smaller one, and gave a gentle push so he sank down onto the cool leather. The short maid skirt rode up again, exposing the damp pink thong and the obvious bulge of his leaking cock. His stockinged thighs pressed together instinctively, but the movement only made the silicone breasts shift inside the low-cut top.

She released his hand and straightened, looking down at him with a satisfied smile. "Stay right there, little maid."

Matt watched her walk away, the black latex dress clinging to her thick ass and creaking softly with each step. She disappeared through a doorway into what looked like a bedroom or private room. His heart pounded so hard he could feel it in his throat.

He sat frozen on the sofa, legs crossed at the ankles in the tall heels, hands gripping the edge of the cushion. Every second felt stretched out. The apartment was quiet except for the faint hum of the building's ventilation. He kept glancing toward the hallway door, half-expecting it to burst open even though it was locked.

His mind raced with the memory of walking down the corridor and riding the elevator dressed like this. Anyone could have seen. The thought made his cock twitch harder against the thong.

What if someone had stepped out? What if the elevator had stopped on another floor? I was so exposed. My makeup, the wig, the fake tits bouncing, the skirt barely covering anything. My cock was leaking the whole time. If a neighbor had seen me they'd know exactly what I am. I still can't believe she made me do that.

Marina returned a moment later carrying two items in one hand: a flat steel chastity cage and a small pink anal plug. She moved with calm confidence, the latex dress hugging every curve of her tall, slim body. She stopped in front of him and held the items up so he could see them clearly. The cage was compact and unforgiving, the kind that would press everything flat against his body. The plug was smooth, tapered, and already glistening with a thin layer of lube.

She tilted her head, studying his flushed face. "Would you like me to be your Mistress?"

Matt's painted lips parted. His voice came out small and shaky, barely above a whisper. "Yes, Mistress."

Marina's smile widened. She set the cage and plug on the leather cushion beside him, then reached out to cup his chin, tilting his face up so their eyes met. "Good girl. That's exactly the answer I wanted to hear." Her thumb brushed lightly over his glossy lower lip. "Now we can begin."