The Trans Woman Who Taught Me Who Was in Charge

Before I became who I am today, I was an ordinary man, or so I believed. I was a little over twenty, had an on-again, off-again girlfriend, and a life that looked perfectly ordinary from the outside. But inside, something didn’t fit: ever since adolescence, I had been attracted to women’s clothing and, above all, trans women. I never talked about it with anyone. I kept it hidden the way you keep a key to a door you still don’t dare open.

Around that time I started getting into forums and chat rooms, the kind that existed before everything was called an “app.” I spent entire nights reading, looking at photos, writing messages I almost never sent. Until one night, in the early hours of the morning, I came across Renata’s profile.

She was a trans woman in the midst of hormonal treatment, mature, somewhere in her forties. She wasn’t the kind of beauty that appeared in magazines: she had a full figure, pronounced features, and applied her makeup with a generosity that someone else might have considered excessive. It drove me crazy. There was something about her confidence, about the way she wrote without beating around the bush, that made me feel small and curious at the same time.

We started chatting. At first I thought she wasn’t particularly interested in me, that she was only keeping the conversation going out of politeness. I grew a little desperate. I didn’t know how to steer things toward the territory I wanted, so one night I gathered my courage and wrote to her directly, telling her I found her attractive and was dying to invite her out for a drink.

She wasn’t one for long messages.

—I like the idea —she replied—. But you’d better come here. I’ll send you the address.

With very little experience, I took this to mean she wanted me to pick her up so she wouldn’t have to travel to some bar. How innocent I was.

***

I arrived on a Friday night. The moment I rang the bell, she came out to greet me dressed as if she were going to a party: an impossibly voluminous blonde wig, lips painted an intense red, and a short black skirt that opened with every step. She lived on the third floor of a building without an elevator, and I followed her upstairs with my eyes fixed on her ass.

With every step, her skirt lifted just enough to let me see the dark satin fabric of the thong digging between her buttocks. My mouth went dry and my cock grew hard inside my pants. Without daring to say it, I thought that I wanted to bury my face there, lick that black fabric until it stuck to her cunt.

—Come in, don’t be shy —she said, opening the door to her apartment.

Inside, it smelled of sweet perfume and cigarettes. She made me sit on a small sofa, offered me a glass of water, and we began talking about anything and everything—the city, work, nothing in particular. I could barely listen. All my attention was focused on her hands, on the way she gestured, on the way she looked at me from the corner of her eye.

The apartment was small and filled with details that gave her away: old photographs on a piece of furniture, wigs on stands atop the dresser, bottles of makeup lined up like soldiers in the bathroom, which I could see from the sofa. Everything spoke of a woman who had built herself from the ground up, without asking anyone’s permission. I, who wasn’t even brave enough to admit out loud what I wanted, watched her with a mixture of desire and envy.

—Why are you so nervous? —she suddenly asked me, crossing her legs—. I don’t bite. Well, not much.

I laughed without meaning it, betrayed by the tremble in my own voice. She moved a little closer on the sofa, until her thigh brushed mine. I felt the heat of her skin through the skirt and my breath caught.

She didn’t take long to come closer. She kissed me slowly, almost with a teacher’s patience, while I let her do as she pleased, like a new student. Her hands were firm, her tongue possessed the confidence of someone who had done this a thousand times. She put her fingers in my mouth, made me suck them, and smiled when she saw how I licked them without hesitation.

—You’re such a little thing, my love —she murmured against my ear—. I like your beard. I’m going to fuck my whole face with it.

She ran her hand over my pants and squeezed the bulge already showing there. She let out a hoarse little laugh.

—Oh, look how hard you are. And I haven’t even started yet.

She asked whether I had ever been with a woman like her. I told her no, that she was the first. She smiled in a way I didn’t know how to read at the time, but understood very well afterward.

***

We made our way to her bed kissing. I pressed myself against her, held her waist, her broad hips, everything that had obsessed me from behind the screen. I slipped my hand beneath her shirt and grabbed her tits: two warm breasts, still developing from the hormones, with nipples hard as little stones. I pinched them, and she let out a sigh that made me even hotter.

While I lost myself in that, she, far more skillfully, had already undone my belt without my noticing.

She pulled down my pants and underwear with an expert motion. My cock sprang free, hard and throbbing, the tip already wet. Renata smiled, ran her tongue over her painted lips, and took it in both hands.

—What a delicious little cock you have, my love.

She stroked it for only a few seconds, squeezing the base, then lowered her head. She took my entire cock in one go, all the way to the back of her throat, without gagging or pausing. I felt the roof of her mouth, her tongue curling around my glans, saliva running down to my balls.

What came next was unlike anything I had ever experienced. She took it all the way in, wrapped it in those thick lips stained red, and glanced at me from the side as she slowly pulled back, letting me see a string of drool stretching from the tip to her mouth. She stopped right at the head, brought out her broad tongue, and dragged it over me with a slowness that made my legs tremble. Then she sucked my balls one at a time, taking each one completely into her mouth while she slowly jerked me off with her hand. And she swallowed me whole again, until her nose pressed against my pubic bone.

—Mmm, what a delicious cock —she moaned between sucks—. You’re going to come in my mouth if I keep this up, aren’t you, daddy?

I held on to the mattress with both hands, arched back, feeling my orgasm rising inside me. I never wanted it to end. Every time I felt myself getting close, she noticed and slowed down, squeezing the base with her fingers like a ring and forcing me back down. She knew exactly what she was doing. She was preparing me, and I didn’t realize it.

I was so spent that I didn’t notice the exact moment she stopped concentrating there. She began kissing me around my groin, my thighs, my hips. She moved down and up, licking every crease, biting the skin on the insides of my thighs, marking out a path whose destination I didn’t understand.

Until she made me turn around.

Standing at the edge of the bed, I felt her settle behind me, crouching. Then she began kissing my buttocks. Biting them. Squeezing them with both hands while I held myself up, confused and aroused in equal measure. She spread my ass with her thumbs, exposing it completely.

—What a fine ass you have —she said between kisses—. Well, look how nicely you were hiding it. This is a whore’s ass, daddy. An ass made to be pounded.

I said nothing. I didn’t know what to say. And while I was thinking about it, I felt her tongue forcing its way into a place no one had ever touched before. She began licking my asshole slowly, in circles, soaking it with saliva. Then she pressed the tip against it and drove it inside, penetrating me with her tongue, fucking my ass with her mouth. A current of pleasure and fear ran all the way up my back. My knees trembled. A long, high-pitched moan escaped me, one I didn’t recognize as my own.

—That’s it, my love, relax your little ass for mommy —she whispered before spitting between my buttocks and going back to licking.

She inserted one finger. Then two. She moved them inside me patiently, scissoring them to open me up while she continued licking around me. For the first time, the clear and terrifying thought crossed my mind that perhaps she wasn’t expecting me to penetrate her, but the other way around.

My fears were confirmed immediately.

With a movement of her hand, she told me to lean on the bed, to leave my body bent over and exposed. And there, as she removed the satin thong that had aroused me so much, I saw for the first time what she had been hiding beneath her skirt: a hard, thick, veiny cock, long enough to make me swallow. Her balls were drawn tight against her body, and a thick drop hung from the glans, shining in the lamplight.

—Stay still —she said, her voice suddenly sounding deeper and more assured—. Now it’s your turn.

***

I didn’t know how to react. I asked her not to do it. Not with a firm “no,” but in the half-voice of someone who really wants to be persuaded. I told her I wasn’t comfortable because she hadn’t put on a condom.

—Don’t worry, sweetheart, I’m clean —she replied without stopping—. And at my age, if I go looking for one now, I’ll lose my erection. Leave it to me. I’ll take care of you and slip it in nice and easy, you’ll see.

As she spoke, she was already spitting on her cock, coating it with saliva and her own precum. She pressed the hot glans against my asshole and pushed just a little, testing it. She held me by the hips with a strength I hadn’t felt from her before, her painted fingernails digging into my flesh. I was trapped between two things: fear of making her angry and how desperately horny the whole situation made me. In the end, the second one won.

I relaxed. I let her in.

The head of her cock slowly forced its way through my ring, with a burning sensation that made me clench my teeth and bite the sheet. I felt every inch entering, opening me little by little, until I felt her balls bumping against mine. She was inside. All the way inside. I stayed still, panting, my ass impaled on another woman’s cock for the first time in my life.

—Oh, you’re so tight, daddy —she moaned behind me—. You’re a virgin back here, aren’t you? Not anymore. This ass is mine now.

She began to move. She pulled her cock almost all the way out, then drove it back in to the hilt, setting a slow rhythm at first, gauging my response. Every thrust tore a grunt from me. The burning gradually turned into something else, a new, dense sensation rising from my ass to the nape of my neck. I could feel her cock touching something inside me that made me see flashes of light. My own cock hung hard between my legs, leaking, swinging with every thrust.

Renata began fucking me faster. Her breathing grew heavy, her voice deeper and dirtier against the back of my neck. Her thighs slapped against my buttocks with a wet smack that filled the room. She dug her nails into my hips and dragged me backward, driving herself deeper.

—You like it, don’t you? —she said—. Say it. Say you like me putting it in you.

—I like it —I murmured with my mouth against the mattress.

—Louder, slut.

—I like it —I moaned—. I like you putting it in me.

—That’s it, my love. Look how much you like it. You were made for this. This little ass has been waiting for a cock for years, and you didn’t know it.

She reached underneath me and grabbed my cock. She began jerking me off in the same rhythm she used to fuck me, coordinating each thrust with every stroke. I couldn’t take it anymore. I felt everything building up—the pleasure of being filled in the ass and her firm hand working my cock—and seconds later I let go. I came in spurts over the sheet, leaving a broad, thick stain, my whole body trembling and my ass tightening around her cock.

—Oh, the boy came without hardly touching himself —Renata panted—. Now hold on to me, because I’m next.

She thrust faster, without mercy, grabbing me by the hair and pulling my head backward. The bed slammed against the wall. I heard her panting in my ear, saying things I didn’t dare repeat even in my own head. I had come to her house believing I would be the one making the decisions that night, and ended up understanding how wrong I was. Not a trace of control remained in me, and strange as it may seem, that was exactly what I needed to discover.

She came quickly, with a long moan that seemed to empty her completely. I felt her throbbing inside me, swelling one last time, and then the heat: thick spurts of semen filling my ass, one after another, while she squeezed my hips and buried herself to the hilt. She remained still for a few seconds, catching her breath, her cock still buried inside me, then slowly pulled away. I felt a thread of warm milk running down my thigh. She took off her wig, soaked with sweat, and tossed it onto a chair. Without the fake hair and smeared makeup, she looked more human, more real, and somehow I liked her even more that way.

She lay down beside me.

***

We didn’t fall asleep right away that night. We talked for hours. She kissed my nipples, squeezed my buttocks with a tenderness that contrasted with the roughness of a few minutes earlier, and told me stories about her lovers, about her life, about the things she had learned the hard way and the things she had chosen. Every so often she ran a finger over my asshole, still soft and wet with her come, and smiled.

—The first time is always like this —she told me, stroking my chest—. You arrive believing one thing and leave being someone else. You still need to let go, my love. But there’s time.

She was right. It wasn’t the last time I saw her. We continued meeting for a long time after that night. She was the one who gave me my first makeup advice, the one who watched me gradually transform into who I wanted to be. She introduced me to other men, we shared more than one bed with strangers, and she showed me a world I had only ever spied on through a screen.

But all that, as they say, is another story.