I Asked My Crossdresser to Welcome Me as a Man

All my life I considered myself straight without a single doubt. I liked women: their curves, their scent, the way they moved when they knew you were looking at them. But a couple of years ago something shifted inside me, slowly, almost without my noticing.

I started looking for crossdresser videos and I couldn’t stop. I didn’t see them as men with breasts. I saw them as perfect women with one extra detail: a hard cock bulging under a skirt or straining the fabric of a thong. It turned me on to imagine myself on my knees in front of one of them, with those eyes looking down at me like only a woman who knows she already has you can look at you.

Until Bianca appeared.

I found her on an app, a crossdresser from my own city. Thin as a reed, soft shaved skin, a doll’s face with full lips and eyes that undressed you in two seconds. The first time we met she opened the door fully transformed into a woman: long black wig, flawless makeup, a short burgundy dress that drew her ass, dark stockings, and heels that made her look huge.

I knelt before she even closed the door. I kissed the tops of her feet and slowly lifted her dress, inch by inch. She smelled of sweet perfume and something hotter underneath. When her cock was freed, hard and shining at the tip, I took it into my mouth like I’d been starving for weeks. She grabbed my hair with the calm of a woman who owns you.

—Good girl —she said, in a husky voice that had a bit of both.

I came without touching myself. Just from her hand setting the rhythm and her taste on my tongue.

***

We kept seeing each other many times, and it was always the same: her dressed as a woman, me on my knees. I liked that role; it made me feel light, with nothing to decide. But after a few weeks I started turning over another fantasy, one I was ashamed to even think about at first.

I wanted to know the other half. I wanted her to open the door the way she went out into the street in broad daylight: as a boy. Young, gorgeous, with that same perfect face but without the wig or makeup. Tight jeans, a T-shirt that showed off the slender body, hair cropped and messy. Just him. And on the other side of the door, me. But me as a woman.

I wanted the roles completely reversed: him in charge as a man, me surrendered as his little slut, in stockings, a short skirt, and painted lips. I wanted him to look at me the way a man looks at an easy woman and treat me that way, all the while knowing that under those jeans there was a woman dominating me from the other side of the mirror.

One night, after I came while she fucked me on my back, I blurted it out between gasps, eyes shut so I wouldn’t have to hold her gaze.

—Bianca… next time… could you receive me as a guy? No disguise. And dress me yourself.

She went still for a second. She looked at me with those eyes that seem to know everything and smiled very slowly.

—So you want to feel it for real —she said—. You want me to turn you into my doll while I go as a guy.

I nodded, trembling between shame and desire.

—Then come prepared. I’ll receive you the way I go out on the street. And when you close the door, you’re going to be Lorena. My Lorena. And you’re going to ask me to take you to bed.

I came again just from hearing her.

***

And now I’m here, in front of her door, my heart pounding in my throat. I knock. It opens.

There he is. As a boy. And he’s even hotter than I’d imagined. Jeans that outline a bulge I already know, tight black T-shirt, short tousled hair, bare face with nothing on it and still perfect. Bruno. Same body, same expression, another name for the street. He looks me up and down and smiles with that mouth I’ve kissed a thousand times painted red, and now, bare, it seems more dangerous.

—Come in, Lorena —he says, in a deep, steady voice, without a trace of the huskiness from before.

I close the door behind me. And I know there’s no going back now.

He looks at me for a long moment, unhurried. Then he tilts his chin toward the living room.

—Take off your clothes. All of them. Slowly. I want to watch you do it for me.

My hands tremble as I pull off my T-shirt. Then the shoes, the pants. I’m left in my briefs, and the erection already pushing at the fabric gives me away. Bruno comes closer, takes my chin, and forces me to look him in the eyes.

—Those too —he says—. Girls like you don’t wear men’s briefs.

I obey. He brushes the tip with a finger, takes it to his mouth, and sucks it without taking his eyes off me.

—All ready, Lorena. Good girl.

***

He leads me by the hand to the bedroom. On the bed everything is laid out like an altar: a tiny black lace thong, fishnet stockings, a red garter belt, a very short pleated skirt, and a mesh top that hides nothing. Beside it, an open makeup case and a leather collar with a silver ring.

—Sit down —he orders, pointing at the dressing table chair.

I sit naked, still hard. Bruno stands behind me, rests his hands on my shoulders, and speaks in my ear with that boyish voice that leaves me defenseless.

—Today I’m turning you into mine for real. And when I’m done dressing you, it’s going to be you asking me to keep going.

He starts with the stockings. He rolls them up and pulls them over my legs, grazing my skin with his fingertips. The nylon makes my whole body tingle. Then the garter belt, which he tightens around my waist while pinching one cheek and fastening the straps with a patience that drives me crazy. He saves the thong for last. He slips it over my ankles and slides it up slowly, until the fabric digs in and squeezes my wet tip.

—Look at yourself —he says, turning the chair toward the mirror.

I’m me, and I’m not me. Long legs inside the fishnet, waist cinched by the garter belt, my erection peeking out beneath the lace. He puts the mesh top on me, leaving my nipples visible, and the skirt that barely covers the top of my thighs.

Then comes the face. He paints my lips a dark red, slowly, never taking his eyes off mine. Smoky shadow, lashes, a touch of blush. He makes me watch myself the whole time.

—Say it —he murmurs—. Say who you are now.

—I’m Lorena —I say, my voice breaking—. I’m yours.

He puts the collar on me, closes the clasp, and clips on a short leash.

—On your knees, Lorena.

***

I drop to the floor. The skirt rides up, the thong buries itself into me. Bruno unbuttons his jeans, pulls down the zipper, and takes out his cock, already hard, the head taut and shining. He smells like clean boy and desire, nothing else.

—Open your mouth.

He grabs my short hair and drives in all the way. He fucks my mouth hard, without pause, setting the whole rhythm himself. The fresh makeup runs with my tears, saliva dribbles down my chin and falls onto the mesh top. I can’t breathe properly and still I don’t want him to stop.

—That’s it —he says through clenched teeth—. Good girl.

I come again without anyone touching me, when he goes all the way in and forces me to swallow. I stain the thong, the lace soaking wet against me. Bruno gives a soft laugh, pulls out slowly, and runs his thumb over my mouth to fix the smeared red.

—This was only the beginning, Lorena. Now come to bed.

***

He puts me on all fours on the mattress, the skirt hiked up to my waist, the thong pulled down to mid-thigh. He takes off his T-shirt unhurriedly: flat torso, soft skin, small hard nipples. Then the jeans and underwear. His cock springs up rigid, thicker than I remembered when I used to see it peeking out under a dress.

He positions himself behind me, grips my hips with firm hands, and prepares me with his fingers, first one, then two, opening me with a mix of care and roughness that makes me moan into the pillow.

—Look at how you ask me for more without saying a word —he says—. Easy. I’m going to give you everything you came here for.

I push my hips back, really asking for it. He smacks my ass, leaving my skin burning and his handprint there.

He pulls his fingers out and presses the head against me. At first he pushes slowly; the tip enters and rips a long gasp from me. It hurts and, at the same time, it’s exactly what I wanted. Then he thrusts all the way in, filling me with a heat that pounds deep inside me with every movement.

—Fuck, you’re so tight —he says, his voice rough.

He starts moving hard, deep, pulling on the collar like reins. The leash presses my neck just enough to make me moan louder. Every thrust has its own sound, his hips against my ass, my own sex swinging beneath me, dripping nonstop.

He grabs my hair and forces me to arch my back.

—Look at yourself in the mirror —he orders—. Look at what I made you into.

I turn my head. In the wardrobe mirror I don’t recognize myself: red lips parted, makeup smeared by tears, the mesh top slipping, my whole body surrendered to a gorgeous boy who fucks me with a face concentrated on his own pleasure.

—Tell me who you are —he insists, burying himself to the hilt.

—I’m Lorena —I say through moans—, and I’m yours.

He keeps me like that a little longer, faster and faster. When he’s on the edge he pulls out abruptly, flips me over, and leaves me on my back. He spreads my legs, lifts my skirt, and enters again in one single thrust. Now he looks me in the eyes as he moves, his boyish face a hand’s breadth from mine.

—You’re going to come again without touching yourself —he says—. And then I’m going to come.

He tightens the pace, grips me by the collar, and takes me like an animal. I come again, staining the top and skirt, screaming something even I don’t understand. Bruno groans, drives in to the hilt, and empties himself inside me, one hot pulse after another. When he pulls out, he leaves me trembling and open, with a trickle sliding down my thigh.

He looks at me, panting, still hard, and smiles with that face that has me lost.

—Good girl, Lorena. Now clean up.

***

He brings his cock to my mouth, still tasting like me and him. I suck it obediently, gathering what’s left, while he strokes my hair almost tenderly. And between strokes, he whispers:

—Next time I’ll receive you the same way… and I’ll bring someone else. So you know what another man feels like while I watch you dressed like that.

I moan around him, still full, and I already know I’m going to say yes.

Because I had never felt so surrendered, so loose, so much myself, as I do now: made up, with torn stockings and my head resting on the thigh of this boy who, underneath it all, is the woman who has dominated me from the first day.