The Trans Woman Who Made Me Lose All My Fears

I’ve always been attracted to women with pronounced curves. Ever since I was very young, the ones who caught my eye were the ones with generous bodies: big tits, wide hips, that kind of figure that seems designed to take up space. At sixteen I accidentally came across material featuring trans women online, and something inside me stopped. The female body taken to an extreme no woman I had seen could match, plus an element I couldn’t name back then but that stirred something intense and confusing in me.

Over the years I understood it wasn’t so strange. That desire has its own logic, independent of what you tell yourself before falling asleep. That you can spend years jerking off to something and still convince yourself you’ll never act on it, until one summer night, with just the right amount of alcohol and your guard down, the opportunity appears on the right corner.

Valentina was standing on that corner.

***

I was twenty-one. I had gone out with friends, and before I realized it I was alone on a street that wasn’t the one where the bar was. I saw her from a distance: tall, with a dark mane down to her waist and a tight one-piece that left nothing to the imagination. She was wearing platform sandals that made her almost my height, and her hips moved when she walked with that precision that’s hard to fake. Thirty-four years old, though I didn’t know it yet.

I stopped on the sidewalk. I had imagined her many times and never thought I’d actually do anything.

I walked up because my body moved before my head did.

—Hi —I said—. Sorry to bother you. You’re the most beautiful woman I’ve seen in a long time.

She looked me up and down without hurrying. Dark eyes, a smile that knew exactly what it was doing.

—How sweet —she said—. How old are you?

—Twenty-one.

—Oh, baby. —Her smile widened—. I’m working right now, but if you really want to meet me, write down my number and we’ll arrange it.

I wrote it down. I thanked her. And when I walked away as if nothing had happened, my heart was pounding in my chest at a rhythm that wasn’t normal. My cock was already hard against the fabric of my pants, tight, swollen, showing itself with no shame.

***

The next day I called her. I hung up twice before it started ringing. The third time I let it ring until she answered.

—Hello, who is this?

—The guy from last night. The one from the corner.

—Ah. —There was a brief pause—. I thought you weren’t going to call.

We talked for almost half an hour. She asked me what I was looking for. I told her the truth: that it was the first time I’d ever called someone like that, that I’d been attracted from the very first second, and that I was scared but wanted to meet her anyway. She listened without interrupting.

—Want to come over now? —she said when I finished—. I’m free. And in the mood for a hot little guy like you to fuck me good.

Her voice left me speechless for two seconds. I went.

***

Her apartment was twenty minutes away. I buzzed with fingers that still wouldn’t quite obey me. The door opened before I got to the third floor.

Valentina was in the doorway wearing a white silk nightgown: deep neckline, thin straps, the fabric falling just to mid-thigh. Her tits pressed against the fabric with a clarity that left no room for imagination, dark nipples showing under the silk. She wore low sandals and had her nails painted a deep red, the same as the night before.

—Come in —she said—. Close the door.

I sat on the edge of the sofa because I didn’t know where else to sit. She leaned against the piece of furniture in front of me and studied me calmly, with no rush at all.

—You’ve never been with someone like me?

—No.

—And that doesn’t scare you.

It wasn’t a question. It was a precise observation.

—A little —I said—. But I figured I’d regret not coming more than coming.

She came closer slowly. She sat beside me and took my face in both hands. Her fingers were long, the nails that same red as always.

—We’ll take it slow —she said—. And if at any point you don’t want to keep going, you tell me and we stop. Okay?

I nodded.

And then she kissed me.

***

The kiss was long and deep, her tongue sliding into my mouth with a hunger she wasn’t pretending. I put my hands on her waist and pulled her closer. She let herself be guided and started unbuttoning my shirt button by button, slowly, unhurried, while her free hand went straight to the bulge in my pants and squeezed my cock through the fabric.

—Oh —she whispered against my mouth—. You’re already hard, baby.

I slipped the straps of the nightgown off her shoulders. The fabric fell to the floor.

Valentina naked was exactly what I had imagined and more. Big, firm tits, dark, pointed nipples, the narrow waist that contrasted with the width of her hips and huge ass. Flat stomach. Long, well-shaped legs. And below, hanging heavy between her shaved thighs, the cock that confirmed what she was: not very long but thick, with the swollen glans peeking out from the foreskin and the balls tight underneath.

I looked at her. She looked at me. Neither of us looked away.

—You okay? —she asked.

—I’m very okay —I said. And it was true.

I stood up, hugged her, buried my face in her neck. She smelled like something sweet and warm. I went down over her shoulders, over the neckline, and started sucking her tits. Valentina let out a low, steady sound. I took one nipple in my mouth and she responded immediately, hardening against my tongue. She grabbed my hair with one hand and with the other took my hand and brought it down to her cock, closing my fingers around it.

—Touch it —she said—. Don’t be scared. It’s just another one, baby.

I felt it throbbing in my fist. Soft at first, then gradually hardening while I worked it clumsily, my mouth still on her nipple. I moved to the other nipple, bit it slowly, and in my hand her cock finished getting hard, thick and hot, with a clear drop beading at the tip.

—That’s it —she gasped—. Slow.

I kissed my way down her stomach, and before I got any lower, she took me by the shoulders and told me to sit on the sofa.

***

She knelt in front of me and took my pants off with precise movements. When she freed my cock from my underwear, a satisfied smile slipped across her face.

—Look at this cock —she murmured—. All for me.

She took as long as she needed. She started with her tongue, licking from the balls to the tip in a slow path, sucking one ball and then the other, taking them whole into her mouth. Then she moved up and worked the glans with a skill I had never experienced before: her tongue moving in spirals around the head, the exact pressure at the exact moment, the rhythm shifting from slow to firm without warning. She swallowed me whole, deep, until my nose touched her pelvis, and stayed there, gulping, squeezing the base with her throat.

Every so often she lifted her eyes to mine without taking me out of her mouth, and that look was hard to hold. She spat saliva on top, grabbed me with her hand and shook me while sucking my balls, alternating between the two without losing the rhythm.

—Relax —she murmured, and the vibration of her voice went through my entire body—. Let me do it.

When she stopped, it wasn’t because I’d reached my limit. She stopped because she chose to. She stood up, took my hands, and made me lie back on the sofa with my legs raised.

What followed was something I had already experienced before, but never with that intensity. Valentina spread my ass cheeks with both hands and lowered her mouth to my hole. I felt the hot, wet tip circling around it, pushing in little by little, entering. A groan escaped me, one I didn’t recognize as my own.

—What a nice little ass you’ve got —she said, and buried her tongue again.

She climbed with her mouth up to my cock and took it whole again, while the middle finger, soaked with spit, pressed against my hole from the outside. It went in little by little, so gently that I never felt uncomfortable. One finger first, then two, curling them inside and finding a place that made my back arch against the sofa. My cock swelled even more in her mouth.

—There, see? —she said, lifting her head for a second, her left hand slowly jerking me off—. Inside there’s something that’ll make you see stars. You’re going to learn.

And she went back to sucking. Between pauses she would lift her head, her mouth shining with saliva.

—You taste so good —she would say, and go back to it.

I didn’t know how to process what I felt. I only knew I didn’t want her to stop.

***

When she asked if I wanted to return the favor, I said yes before I’d even finished thinking about it.

She lay face down on the sofa with her legs spread. From that angle her ass was a perfect exaggeration: big, round, relaxed, with the slit open and the pink hole visible between her cheeks. I moved closer, took her by the waist, spread her cheeks wide with my thumbs and bent down.

There are things one imagines many times before doing them. This was one of them. The smell of clean skin, the warm texture of her flesh, the immediate response of her body when I ran my tongue over her for the first time. I ate her ass without holding back, my tongue going in and out, circling, sucking her hole like it was a cunt. Valentina leaned against the back of the sofa and pushed back with calm firmness, rubbing my face against her ass.

—Oh, daddy —she panted—. You eat it so good. Put it all the way in. Stick your tongue way inside me.

She kept talking under her breath, dirty phrases turning into moans before they were even fully formed. Between licks I slid my hand underneath and grabbed her cock: it was hard as a rock, leaking pre-cum onto the upholstery. I worked it slowly while I kept eating her ass.

At some point she turned around and took my face in both hands, her eyes shining.

—I want you to taste me —she said—. Want to try?

I understood what she meant. I held her gaze for a moment, my mouth still wet.

—Yes —I said.

She sat on the edge of the sofa, legs open, cock standing up pointing at the ceiling. I knelt between her thighs. I started with a soft kiss on the tip, closed-lipped. Then I opened my mouth, took the glans between my lips, and let my tongue do what felt natural. It was salty, hot, throbbing against my palate. I went a little deeper, took half of it into my mouth, choked, and came back up. Valentina didn’t rush me. She put her hand on my head but didn’t press.

—That’s it —she said—. Slow, baby. Suck it the same way they sucked you. You can feel how it responds, right?

Yes. I could feel it. Her cock swelled more between my lips every time I worked it with my tongue. I grabbed her balls with my left hand, kneaded them slowly, and with my right I jerked her off at the base while the tip filled my mouth. Instead of frightening me, it stirred something in me I couldn’t name at the time but that was, clearly, arousal. My own pulsing between my legs, leaking, harder than it had ever been.

I stayed like that for several minutes, sucking, moving my head up and down, letting her set the pace with her hand in my hair. When I stood up, my mouth swollen and a thread of saliva hanging from my chin, she kissed me slowly and long, not caring about anything.

—You’re incredible —she said—. You’re going to be a machine if you keep this up.

***

I put the condom on with fingers that no longer fully obeyed me. Valentina lay back on the rug with her legs over her shoulder and her eyes fixed on me. She took her cock in one hand, pressed it against her stomach, and with the other opened one ass cheek.

—Put it in —she said—. Break my ass nice and slow.

I spat on my fingers, ran them over her hole, lined up the tip against her little rosebud and pushed. I went in slowly, centimeter by centimeter, controlling the impulse to go faster. The sensation was hard to describe: heat, pressure, a tight ring that sucked me in with every push, her body matching every movement with a precision that seemed rehearsed.

—No fear —she said, teeth clenched—. Like that. All of it. Fuck me.

I let myself go. I pushed all the way in, until my balls hit her ass, and stayed there a second before I started moving. Sliding almost all the way out, then back in to the base, the rhythm gradually building.

She grabbed her tits with both hands, pinched her nipples, threw her head back, shaped her moans with a naturalness that made everything more intense. Her cock bounced against her own stomach with each thrust, leaving a pool of sticky fluid on her skin.

—Harder —she gasped—. Come on, harder, like that, fuck my ass good.

At some point she sat up, made me sit on the sofa, and sat on top of me with her back to me, impaling herself on my cock. The image from behind was unreal: that broad, soft back, the huge ass moving up and down to its own rhythm, swallowing me whole every time she came down, her hands braced on my knees to keep her balance. I wrapped my arms around her from the front, grabbed her tits with both hands, and stayed still for a few seconds so I wouldn’t come too soon, while she kept rising and falling on me, squeezing me inside with her ass every time she reached the bottom.

Then she turned around without taking my cock out. Facing me, with her knees on either side of my thighs. From that position I could see her completely: the concentrated expression, the half-open mouth, the tits moving with each thrust, her hard cock slapping against my stomach, her hips meeting mine in a rhythm we built together. I took her by the waist and helped her move. With one hand I grabbed her cock and jerked her in the same rhythm she was sitting on mine.

—That’s how I like it —she said, and closed her eyes—. Fuck me and make me cum at the same time. Like that, daddy.

I hit my limit with that image. I told her I couldn’t hold on any longer. She stood up slowly, took off the condom with two fingers, and finished with her mouth what she had started with her ass. She took me all the way in, sucked my balls, went up and down three times with her throat clenched, and that was enough. I blasted her mouth full of cum in spurts, a lot of it, shaking my hips against her face because I couldn’t stop. She swallowed part of it and let the rest run down her chin onto her tits.

When I finished, she lifted her head and smiled at me, lips shining, a white thread hanging from the corner of her mouth.

—All of it —she said, running a finger over her chin and sucking it clean, then climbed up to kiss me.

The kiss surprised me. The taste was strange and mine at the same time, salty, thick, my own in her tongue. I didn’t pull away.

***

We stayed silent for a while, her resting against my chest, me with my hand on her back. The room was still. Outside, the night continued.

—Want to stay a little longer? —she asked.

—Yes.

She got up to go to the bathroom. I followed her without exactly knowing why. There was something about her that wouldn’t let me stop. When I should have already been dressed and saying goodbye, I found her leaning with her hands on the sink, ass toward me, looking at me through the mirror with half a smile. I got hard again in two seconds.

I knelt behind her and ate her ass again, without a condom this time, my tongue going clean and direct into her hole. Valentina braced herself against the wall with one palm and let out something that was half laugh, half something else.

—You’re crazy —she said.

—I know.

I stood up, grabbed a condom from the pocket of the shirt lying on the floor, put it on, and took her hips with both hands. I pushed my cock into her slowly again, now standing, and fucked her against the sink with calm, watching both of us in the mirror: her tits swaying, me behind her with my hands sunk into the flesh of her ass. She lowered her head, then raised it, found her eyes in the reflection and guided me with her body, leaning forward, giving me more access.

—Like that, baby —she murmured—. Fuck me hard. So I know you were here.

At some point I pulled out, turned her around, sat her on the marble of the sink and knelt down. I took her cock in my mouth again, worked it calmly, without hurry, until I felt it respond fully. I sucked her deep, pulled it out, jerked her with my hand against her lips, and took it back in. I masturbated her slowly with my mouth until she came. Her thighs went tense, she grabbed my hair, and she filled my mouth with hot cum with a long, deep moan. It was quiet and focused. Almost intimate. I swallowed what I could.

We showered together. She soaped my back and slipped her soapy fingers into my ass without stopping smiling, not pulling them out, playing. I lathered shampoo into her hair, and with my other hand I grabbed her soft cock under the water and worked it slowly until it got hard again, even though we both knew we weren’t going to do anything else. We didn’t talk about anything important. There was something strange in that moment, a closeness I hadn’t anticipated and didn’t know how to classify, but also didn’t want to interrupt.

***

Before I left she asked if I was going to come back.

—Most of them don’t —she said, without bitterness. As if it were a statistical fact she had learned to accept.

—I will —I said.

And I did. It took me three days to call her. After that second time there were no more fears to name and no barriers to cross. There was only continuing to discover what else I wanted to learn, and how far that desire that had always been there would take me, waiting for me to have the courage to follow it.

And Valentina, with that calm patience I never quite understood how she could have, was always willing to teach me.