What That Trans Woman Did to Me Behind the Park

I met her on Instagram toward the end of summer. She had one of those profiles that mixed nighttime selfies with short dancing videos, and in every photo she looked exactly like what she was: a trans woman in her thirties who made no attempt to hide anything. Straight, dark-brown shoulder-length hair, generous curves that clearly owed something to surgery, and the attitude of a woman who knew exactly what she had and used it without asking permission. I followed her without thinking twice.

She replied the next day with a direct message: “I saw you followed me.” Just like that, without any preamble. We started talking that same afternoon. Her name was Valeria, she lived a few blocks from my building, and she was just as direct in the chat as she was in her photos. After three days, she asked me what I was looking for. I told her the truth: I wanted to fuck a trans woman, I wanted to suck her cock, and I wanted to fuck her ass. She told me she felt the same way, that it had been a long time since she’d found a guy who got straight to the point without beating around the bush. Five days in, we agreed to meet.

I was twenty years old. I’d had encounters with girls, one or two without anything particularly memorable coming of them, but never with a trans woman. I didn’t really know what to expect that night as I waited, leaning against the wall of my building, my heart making more noise than I wanted to admit. It was close to eleven, and the street was quiet, with that sleeping-neighborhood stillness Wednesdays had.

I saw her appear at the far end of the block. She walked slowly, with the confidence of someone who knew her own body well. She wore a tight black skirt down to her knees, a light-colored sleeveless blouse that revealed the beginnings of large, firm tits, and heels that clicked against the asphalt with every step. She looked at me from a distance, sketched something that wasn’t quite a smile, and kept coming without hurrying.

“Are you the one who was waiting for me?” she asked when she reached me.

“Yes,” I said. Brilliant answer.

She laughed softly, and that sound was the first thing that relaxed me a little. She smelled good, something warm and floral I couldn’t identify. I pointed toward the side of the building. There was a narrow passage leading to a small vacant lot, shielded by the walls of the neighboring buildings and by the almost total darkness the hour provided. Nobody went through there at that time of night. I’d checked more than once.

She went in first without hesitation. I followed.

***

The lot wasn’t much: uncut grass, dry dirt, a few unplastered brick walls. But the darkness was almost perfect. Valeria turned toward me as soon as we crossed the passage and looked me up and down with a calmness that made me even more nervous. She didn’t say anything. She simply raised an eyebrow and placed an open hand over my fly, measuring the bulge already straining against my jeans.

“You’ve already got it hard,” she said, squeezing me slowly, closing her fingers over the fabric. “Relax. I’m going to suck you good.”

And she knelt.

There was no more preamble than that. She unbuckled my belt with one hand while holding me firmly by the hip with the other, as if to keep me from moving. She lowered the zipper slowly, tugged my pants and underwear down to mid-thigh, and pulled out my cock, already rock-hard and glistening at the tip. For a moment she simply held it, weighing it in her palm, then pressed it twice against her cheek, rubbing the head against her skin as if marking her face with it. Then she stuck out her tongue and licked me from the base to the tip in one long, slow movement.

“What a tasty cock,” she murmured, and opened her mouth.

The first thing I felt was the heat. Then the even pressure of her lips closing around the head, her tongue wrapping underneath it, pressing against the frenulum. There was no hesitation, no tentative exploration: she swallowed me with the confidence of someone who had been sucking cocks for years and enjoyed every second of it. She lowered her head until I felt the back of her throat close around the tip, stayed there for a moment with her nose touching my pubis, and began to rise slowly, dragging her tightly closed lips along the entire shaft.

I didn’t know where to look. I watched her, saw her dark hair moving with every bob of her head, her cheeks hollowing whenever she sucked hard, and had to look away because it was too much. I looked at the brick wall, the starless sky, the shadows. Then I looked back at her. A strand of saliva hung from the corner of her mouth and fell onto her cleavage. I let out a low moan that I tried to control and couldn’t quite.

“Take it all,” I told her, my voice hoarse. “Suck me all the way down.”

She picked up the pace. She started fucking my mouth rapidly, bobbing her head up and down without stopping, making a wet noise each time she pulled my whole cock out and swallowed it again. Every so often she stopped for a second with just the head inside and looked up at me, mouth open, tongue showing, waiting for me to push my hips so she could sink me back in. Those moments when she looked at me were the worst, in the sense that I had to grit my teeth not to come right there. Then she went back down and the pace rose another notch.

She pulled my cock out for a moment, spat on it, gripped it in her hand, and started jerking me off while sucking my balls, one after the other, taking them fully into her mouth. Then she rose again and swallowed me in one single motion, all the way to the back. A short gag escaped her, making her eyes water, but she didn’t pull away: she tightened her lips around the base and held there, swallowing, her throat closing and opening around the tip as if she were milking me from the inside.

I tried to pull her head away with one hand. Not because I wanted her to stop, but because I needed a second so I wouldn’t finish yet. She caught my wrist, gently moved it away, and kept going. As if she knew exactly how much endurance I had left and precisely how far she could take me without making me come too soon.

It turned out she did.

***

When she stopped, it was because she decided to. She stood up slowly, her mouth still shining with saliva, adjusted her hair with one hand, and turned around. Without saying a word, she hiked her skirt up to her waist. The thong was black and barely visible in the half-light, a little cord buried between two large, round ass cheeks that ended up level with my cock. She moved it aside with two fingers, spread one cheek with her other hand, and waited.

“Put it in,” she said, her cheek resting against the brick. “Fuck my ass.”

I understood what she wanted.

I moved closer. I spat on her asshole and ran the head of my cock over it, rubbing against the tight opening until I felt it give slightly. I grabbed her hip with one hand and guided myself with the other, pressing the tip against the ring. I pushed slowly. The head went in with a short thrust and she let out a long moan, pressing her palm against the wall. I kept working it in little by little, inch by inch, feeling her ass close around my shaft as I advanced. When I was fully inside, my balls resting against her cheeks, she exhaled a low, short sound, like someone receiving something she had expected, and which nevertheless surprised her no less for that.

“Oh, you’ve got such a tasty cock,” she said through her teeth. “Fuck me hard, come on.”

I started moving.

Her ass was tight in a way that felt new to me, different from any pussy I’d fucked before. Every thrust required a certain amount of force, a certain deliberation, and at the same time created an intense friction that traveled all along my shaft and made me grit my teeth. I started slowly, pulling almost all the way out and sinking back in to the hilt, and gradually sped up until I was fucking her with hard thrusts that made my thighs slap against her ass with a short, dry smack each time.

Valeria accompanied every thrust with a small backward roll of her hips, as if to take me deeper, and the sound of our bodies in the darkness of the lot mingled with her restrained breathing and the short moans that escaped her whenever I reached the deepest point.

“Harder,” she murmured. “Break my ass, come on.”

I grabbed her hair with one hand and pulled back, forcing her to arch her back. With the other I held her by the hip and started fucking her faster, without stopping, burying myself to the balls with every thrust. She reached one hand down and grabbed herself between the legs, and from the movement of her arm I understood that she was jerking off her hard cock while I fucked her from behind.

I had my hands on her hips and watched her silhouette against the wall, the curve of her back, her hair falling forward with every movement, her ass cheeks bouncing against my pelvis. I lowered one hand and reached around her chest beneath the blouse, squeezing one heavy, full breast, feeling her hard nipple against my palm.

I felt the limit approaching again.

“I want to come in your mouth,” I said. I don’t know where I found the voice to say it.

She didn’t answer with words. She simply straightened up, let my cock slide out of her ass with a wet sound, lowered her skirt with a calm gesture, turned toward me, and knelt in the dirt again.

***

What came next was different from the start. If she had gone slowly and precisely before, now the pace was different from the very beginning. She put my entire cock in her mouth without even cleaning it, held the base with one hand to guide it, and began moving her head at a sustained speed that never let up. Long sucks alternating with quick, steady movements, her tongue always working underneath, her lips closed with perfect pressure. With her other hand she grabbed my balls and began caressing them, gently tugging them downward each time she sank all the way down.

“That’s it, that’s it,” I panted. “Don’t stop, I’m going to come.”

I tried to warn her more clearly. I managed to say her name through my teeth, barely. She sped up even more, looking up at me with her eyes fixed on mine, her mouth filling and emptying with my cock at an increasingly frantic pace. The sensation accumulated with an intensity that was almost impossible to process.

When I reached the point of no return, it was inevitable and sudden. I clenched, my whole body tensed, I grasped at the air without finding anything to hold on to, and sent the first jet of cum straight against her palate. She didn’t retreat a centimeter: she stayed there, her lips tight around the middle of my shaft, and continued sucking slowly while I kept coming. I felt my cock emptying into her mouth in thick spurts, one after another, and she received them all without losing a drop, with a patience that was almost absurd.

When I stopped throbbing inside her mouth, she kept sucking with gentle pressure to milk out whatever remained, dragging her lips from the base to the tip and back again. She stopped and waited a moment with my cock still resting on her tongue, and when she finally pulled away, I saw her open her mouth slightly to show me the pool of semen, close it, and swallow without making any particular expression about it. Then she licked the head one last time, cleaning off the final drop.

As if it were the most natural thing in the world.

I leaned against the wall, my legs somewhat weak and my back against the cold brick. Valeria stood up, ran her thumb over the corner of her lips, adjusted her blouse, brushed off her skirt with an open hand, and ran her fingers through her hair. Everything in the same calm order in which she had arrived, like someone finishing one task and moving on to the next.

“Good night,” she said.

And she left through the passage without looking back.

***

I walked back to my apartment without hurrying. The building was silent, the elevator took a while as always, and when I finally collapsed onto the bed, I could still smell her perfume in my nose and taste her saliva on my skin. I fell asleep within five minutes.

I didn’t write to her on Instagram again until a week later. She replied immediately, in the same direct tone as always, as if nothing had happened and at the same time as if everything that had happened between us were an established fact that didn’t need to be mentioned. No beating around the bush, no drama.

I asked her if she felt like doing it again.

She told me Thursday at eleven worked for her.