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Author Topic: My First Sissy Training Session – A Raw Femdom Experience  (Read 140 times)

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My First Sissy Training Session – A Raw Femdom Experience
« on: February 05, 2026, 03:12:04 PM »

I never thought I’d be here, kneeling in my ex’s living room,穿着 a lace-up sissy dress and garter belt. But here I am, legs spread, cock hard in the garter straps, waiting for Mia to decide what she wants to do to me next. She’s always been the bossy type – the kind of woman who could make you feel like a useless kid just by narrowing her eyes. Now she’s my trainer, my dominatrix, and every second I spend in this role makes me want to sink into the floor.

Mia leans against the wall, sipping her beer, watching me like a hawk. Her tank top is tight across her chest, her short hair buzzed low enough to show the line of hair curling down her neck. She’s 23 and I’m 21, and we met at a mutual friend’s party last week. She asked me if I’d ever “pretended to be a girl for her,” and I lied and said no. Now I know why she invited me over “to talk.” Her living room is converted into a sex dungeon – black leather cuffs hang from the bed, a wooden paddle rests on the coffee table, and a strapon hangs from the wall like a weapon.

“You’re nervous, aren’t you?” she says, her voice low. She drops the beer can and steps closer, her flip-flops slapping the floor. I nod, cheeks burning. She grips my chin and forces me to look up. “Don’t be. You’re a sissy now. You don’t get to feel proud or ashamed. You just do what you’re told.”

She pushes me toward the coffee table, where a strapon is laid out with lube. I stare at it, my cock already aching behind the garter belt. Mia unclips the strapon, its shaft thick and curved unnaturally. “Take it,” she growls. I fumble, gripping the shaft and positioning it over my stiff cock. The silicone slides over me slowly, cold at first, then warming against my skin. Mia fastens the harness around my chest, the metal buckles digging into my collarbones.

“What’s my name?” she says. “I’m your sissy,” I whisper. “Good. Now prove it. Crawl to the bedroom. I want you to beg me to let you touch yourself. But if I say no, you don’t move. You just cry like a little girl.” I scramble forward, hands on the floor. The strapon rubs against the carpet, each inch of it pressing into my cock. Mia follows me, her footsteps loud in my ears. Once inside the bedroom, she slams the door shut and locks it. I kneel, hands on my thighs, heart pounding.

“Say it,” she says, crouching to level with my face. “Say you want me to let you touch yourself.” My fingers twitch toward my crotch, but the strapon is in the way. I’m so hard I feel like I could come just from being trapped in this thing. “Please,” I beg. “Let me… oh God, let me touch myself.” Mia grins, her thumb swiping across my lips. “You’re a good sissy. Now don’t move. Watch me.” She stands, stripping off her clothes. I blink at her, the strapon bouncing against my thigh. Her thighs are covered in light hair, her clit peeking between them as she straddles a chair. I’m supposed to watch, supposed to be humiliated by how much I want her.

“Do you like my pussy?” she taunts. “Do you want to stick your toy cock inside it?” I nod, unable to speak. Mia slaps me hard across the face. “No. You’re not allowed to cum unless I say so.” She leans down, pressing the strapon’s tip to her entrance. I’m shaking, the straps of the garter belt cutting into my legs as I grip the floor. She shoves herself onto me in one smooth motion, the strapon groaning inside her. I can’t feel it – all I feel is the ache in my real cock, trapped beneath the strapon.

“You can’t come,” she repeats, rocking slowly. “You’re just my stupid sissy, and this thing inside me is your punishment.” I whine, tears slipping down my cheeks. Mia slaps me again, harder this time. “Shh. Cry harder. I want to hear you whimper like the girl you’re pretending to be.” She fucks herself onto the strapon for what feels like hours, her moans filling the room. I can’t move, can’t speak, can only stare at her bouncing breasts and the way the strapon disappears into her. When she finally cums, she slams her thighs into my face, forcing me to smell her cum. I gag, the scent thick and overwhelming. She yanks it away and stands, laughing.

“You’re so pathetic,” she says, yanking my hair. “But I like you. You want more?” I can only nod. She drags me to the living room, where her friends are at a house party. They’re chatting, drinking beers, and I’m a wreck in my dress and strapon. Mia pushes me toward the couch. “Sit,” she orders. I drop onto it, legs spread, strapon rubbing against the cushions.

One of her friends, a woman with dyed-pink hair, eyes me up. “What’s this?” “A sissy,” Mia says, tightening the strapon’s harness. “He’s my new pet. Watch him for me.” She leaves the room, and the pink-haired woman crouches before me, her lips brushing the strapon’s tip. I freeze. “You like being a girl?” she whispers. “You like getting punished for being bad?” I swallow hard, nodding. She slaps my thighs, then laughs. “You’d make a cute cumslut, baby.”

Mia returns, smirking at the scene. “You’re late,” she tells her friend, yanking me up by the hair. “Remember your punishment. You don’t get to come unless I say so.” She slaps me across the ass, her hand leaving a red handprint against the dress. The strapon jabs into my cock again, and I cry out, tears streaming down my face. I don’t care who sees me now – I just want to feel her approval.

Later, after Mia lets me cum (only after she says “Good sissy” and strokes my hair like a child), I lie on the floor in the dark, still wearing the dress and garter belt. She’s gone, but her voice is in my head, sharp and commanding. I check my reflection in the mirror – my face is red, my eyes puffy, my hair a mess. I look… different. Smaller. But I also feel lighter, like a weight has been lifted.

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