What a Transvestite Never Forgets About Her First Time

It was Saturday, and the sun still hadn’t quite finished going down when I got ready. It wasn’t a complicated outfit: sneakers, gray joggers, a dark polo shirt. The clothes of any boy in the neighborhood, nothing to draw attention. The outside was the same as always, what the world expected to see when they ran into me on the street. The inside was another story.

Before dressing, I took the black thong out of the drawer. I held it for a moment between my fingers, feeling how light it was as always. It was a small garment, almost nothing, just a few strips of lace. I put it on carefully, adjusting it well over my hips, and something in me settled too. I’d been wearing that thong for months every time I was going to be with him. It was my secret, the only one that belonged entirely to me, the only one I didn’t need to explain to anyone. With that on I felt like myself: complete, real, in the body I should have always had, even if I had to cover it all with jogger fabric before going out into the street.

I waited seated on the sofa. I looked at the clock twice for no reason. Outside, the neighborhood was making its usual Saturday noises: music from some neighbor, boys’ voices on the sidewalk, the distant hum of the avenue. Everything the same as always. I, however, was more restless than usual, though I didn’t know exactly why.

Ramiro arrived on time. He always arrived on time.

I met him at the door with a quick kiss on the mouth, first glancing to the sides to make sure the hallway was empty. He accepted the kiss without saying anything, with that calm of his that sometimes drove me crazy and other times seemed like the safest place in the world. We went out into the street walking separately, as friends do, with our hands in our pockets and a prudent distance between our bodies.

That was how we were outside. Two neighborhood friends going out for a drink on a Saturday night. Nothing more than that.

***

The beer hall was packed that night. We got a table at the back, one across from the other, with the music and everyone else’s conversations making a bubble around us. No one looked at us. No one ever looked at us, and that was exactly what we needed in order to be together in that strange, secret way we had built over time.

We drank the first beer almost in silence, looking at each other over the rim of the glass. With Ramiro there was no need to fill time with words. He had that way of listening with his eyes, of making you feel like the only important thing in the room even if there were fifty people around. I liked that about him. Among the many things I liked, it was one of the ones that had hooked me from the start.

The music got a little louder. I leaned over the table and brought my mouth to his ear.

“I’ve got something on underneath,” I told him.

He didn’t ask what. He didn’t need to ask. He only smiled slightly, with that slow smile that undid me, and bit his lower lip. Just that gesture. Just that, and I already felt heat in my chest and a warm dampness between my ass cheeks where the lace of the thong stuck to my skin.

He brought his feet together under the table and trapped mine between his. He didn’t take my hands. He made no gesture anyone could misread. But that minimum contact, that silent pressure beneath the table, lit me up in a way I hadn’t expected. It was as if all the desire we couldn’t show outside concentrated itself in that one point of contact, invisible to everyone except the two of us.

I smiled. He smiled too, looking at me.

I spent the next hour and a half thinking about the way back home, about his cock, about how I was going to feel it that night for the first time in other ways.

***

The return trip was short in distance and long in everything else. We walked as we had come: separate, talking about anything that wasn’t what we both had on our minds. About the weekend’s match, about a mutual friend, about nothing in particular. But I felt every step as if I were approaching something I could no longer stop, something that had been building between us for weeks without our naming it yet.

When we shut the door to my apartment, he gave my ass a slap.

I turned around. I looked at him. He was looking at me too, but without the caution of outside, without the calculated distance we used on the street. I was the one who took the step, as always. I put my arms around his neck and pressed my mouth to his, and he answered by pulling me against his chest without the least caution. He shoved his tongue in without asking, deep, searching for me, and I sucked it as if I were already giving him a preview of what I was going to do to him a little later. I felt his hard cock against my stomach, warm and insistent even through the fabric, and I rubbed against it without hiding it, seeking that pressure.

We separated just enough to look at each other.

“You’re the only thing I want,” I told him. It wasn’t a line I’d rehearsed. It came out on its own, without thinking.

“I’ve been wanting you like crazy,” he answered. “I’ve been thinking about you all week. That mouth, that ass.”

He lifted my shirt over my head and let it drop to the floor.

***

I took off my joggers myself, without hurrying, never taking my eyes off him. I was left only in the black thong, standing in the hallway of my apartment, and I felt his gaze travel over me from top to bottom before he said a single word. Ramiro didn’t talk much in those moments. He looked, and that was enough. But that night he spoke.

“Turn around,” he said in a low voice. “Slowly.”

I turned around and stayed with my back to him, my hands on the back of my neck, letting him see the thong biting into the crease of my ass. I heard his breathing change. I felt him come up behind me, two long steps, and his hands took my hips and pressed me hard against his bulge. His cock, still trapped in his pants, settled between my butt cheeks as if it already knew the way. He rubbed it there, slow, up and down, while he bit my shoulder.

“This ass is insane,” he murmured against my skin. “I’m going to fuck it all night.”

I turned slowly in his arms. I was the one who pulled down the zipper of his pants. I was the one who shoved the fabric down, along with the boxer briefs, and freed his cock, which sprang erect and heavy against my hand. And I was the one who knelt in front of him on the cold hallway floor, because I wanted to be there. Because I’d wanted to be there for a long time and that night I had decided nothing was going to stop it.

His cock was erect in front of me, thick, dark, slightly throbbing, with a pronounced vein running underneath and a thick drop of precome showing at the tip. I knew it by sight and by touch from months back, but never like this, never so close, never with the intention I had now. I took it between my fingers first, gently, weighing it, feeling it throb. I grabbed it by the base and moved it slowly, looking up at his face, seeing his eyes narrow.

I brought my tongue to the tip and gathered the drop of precome with the edge. Salty, dense, with a bitter undertone. I tasted it as if I were trying it for the first time, because in a way that was what it was. Then I went over it slowly, from bottom to top, following the vein with my flat tongue, learning him with my mouth.

“That’s it, baby,” he said hoarsely. “Take it all in.”

I opened my lips and started taking him in. First the head, round and hot against my palate. Then a little more, and a little more. I sucked the tip with pressure, cheeks hollowed, while with my hand I stroked the base and with the other squeezed his balls. He exhaled slowly. His hands settled on my head, not pressing, just resting there, playing with my hair.

I went in farther. Learning the weight, the rhythm, the signals of his body. I started moving with my head, up and down, sucking him deeper and deeper, letting saliva spill from the corner of my mouth and run down the shaft. When I made swallowing motions so the base of my tongue pressed against the glans, I felt him shudder. His legs went rigid. His fingers tightened a little on my head, still without pushing, but no longer with that earlier calm.

“Look at me,” he asked.

I lifted my eyes without taking him out of my mouth. I looked at him from below, my lips stretched around his cock, saliva hanging from my chin. He bit his lip and took a deep breath, and I knew in that instant that he was going to remember that image long after the night was over.

When I took him too far in, I gagged and pulled back. I breathed. A strand of saliva was left hanging between my mouth and his cock. I wiped it away with the back of my hand and went back. Now deeper. I felt the tip push against my throat, that hot, blind blow, and I held back tears while I swallowed him. He let out a short, cut-off moan, and his whole belly trembled.

“Fuck,” he said through his teeth. “You suck so well.”

I took him out for a second to catch my breath. I licked his balls, one and then the other, took them into my mouth one at a time, sucked them while I kept jerking him with my hand. Then I went back to the cock, slid up the shaft with my flat tongue, and swallowed him whole again. I started a faster rhythm, without pauses, and he couldn’t hold back anymore: his hips began to move with me, pushing just enough, fucking my mouth carefully but unable to stop himself completely.

“I’m going to come,” he said in a muffled voice. He tried to pull away, to give me room to decide.

I didn’t let him. I clung to his hips with both hands, dug my fingers into his ass cheeks and pulled him toward me, pressing my lips around his cock. I needed it. I’d wanted for a long time to know what that was: his taste, his smell, that surrender no one else was ever going to get.

I stroked the space between his thighs with my fingers, gently, unhurriedly, while I kept sucking him with my mouth full. I slid a finger under his balls, over the perineum, looking for that spot I knew drove him crazy. He said my name once, in a low voice, almost out of breath. And then he came.

The semen filled my mouth in one surge: warm, thick, with a flavor unlike anything I had known before. I felt the first spurt hit the roof of my mouth, then another against my tongue, and another that made me swallow by reflex. He let out a long moan, pushed once more, and emptied what was left inside my mouth. I stayed still, with his cock still in there, holding it all, feeling it throb while he emptied the last drops.

Then I let him go slowly, carefully, and stayed with my mouth closed, full, feeling the hot weight of semen on my tongue. I parted my lips and showed him what I had inside. He looked down at me with something in his eyes I couldn’t quite name: desire, tenderness, something darker. I closed my lips and swallowed, slowly, in two gulps, so he could see me sending his come down my throat.

“All of it,” he murmured. “Good girl.”

I licked the tip one last time, gathering the drop that was left, and gave him a kiss there. I got to my feet with numb knees and a strange feeling of having crossed something that couldn’t be uncrossed. Not of having done something wrong. Quite the opposite: of having finally arrived at a place I had wanted to reach for a long time.

***

He took my hand and led me to the bathroom.

We showered together under the hot water. Me with my back to his chest, wrapped in his arms, my head tipped back to reach his mouth. The water fell on both of us, first very hot and then lukewarm, and I closed my eyes and thought of nothing that wasn’t that pressure, that warmth, that way he held me without my asking him to.

He kissed my neck. My ear. My shoulder. His hands traveled my waist, my hips, unhurried, as if we had the whole night ahead of us. And we did. One of his hands slid down my belly, stroked my pelvis, and took my cock in an open palm. He started jerking me off slowly, with the water and soap as lubricant, while the other hand pinched one nipple between his forefinger and thumb.

“You’re getting hard again already,” he told me in my ear, in that slow-smile voice of his. “You’re such a horny slut.”

“For you,” I answered, pushing my ass back against his pelvis.

I felt his cock starting to recover against my back, swelling again, searching for the crease. It settled there, between my wet ass cheeks, and he moved it up and down, not inserting it, just rubbing it against me while he kept jerking me off. He opened my ass with his free hand and ran the pad of his finger over my hole, barely brushing me. I tensed and relaxed at the same time.

“Let’s go to bed,” he suggested in my ear. “This isn’t enough for me here.”

We dried ourselves with the two towels hanging up. He carried me in his arms from the bathroom door to the bedroom, and I let him carry me, laughing a little, not really knowing why. He set me on the mattress and fell on top of me, crushing me with his weight, immobilizing me in a way that didn’t bother me in the least.

I could do nothing but stroke his back.

He laughed.

“What do you think you’re going to do if I don’t move?” he asked.

“Wait for you,” I answered. And I meant it.

He laughed again, but he moved. He kissed my mouth, my chin, my neck, went down over my chest and stopped for a long while at my nipples, sucking them until they were hard. He kept going down over my belly, licked my navel, and when he got to my cock he took it all the way into his mouth without warning. I arched on the mattress with a muffled cry. He sucked me a few times, calmly, while stroking my balls, and then flipped me face down with ease, with those hands that knew exactly where to go. He spread my hips, lifted my ass with one hand under my pelvis, and lowered his head.

When I felt his tongue on my ass hole, I tensed first, an involuntary reflex, and then I started letting go. He began slowly: long movements, up and down, unhurried, the tip of his tongue tracing circles around the ring. Then he pushed in, just a little, and I felt him working his way inside. I buried my face in the pillow and moaned. He opened my ass with both hands, spreading my cheeks apart, and went in with his whole mouth, licking me, salivating me, leaving me soaked.

The sphincter yielded little by little under that patient attention. When he slipped in the first finger, it felt more like relief than intrusion. He moved it slowly, in and out, searching for the angle. Then the second. He bent them inward, carefully, and hit that spot that made me clench the sheets in my fists until my knuckles went white. I buried my face in the pillow to muffle what came out of my throat.

“You’re wide open already,” he said, in that low voice. “I’m going to put it all the way in.”

“Put it in,” I begged without lifting my face. “Now. Fuck me.”

“Get on your knees.”

I did. I got myself into all fours, back arched, ass high, supported on my elbows. He got behind me. I felt him spit into his hand and spread the saliva over his cock, and then he set the tip at the entrance that was already ready to take him. The hot tip against the hole, that firm, round, insistent pressure. I took it without resistance, slowly at first, feeling myself opening centimeter by centimeter, and he, with his hands on my hips, pushed it in until halfway. Then he waited a second, breathed, and suddenly shoved all the way in. The scream I couldn’t control was muffled against the pillow.

“Damn,” he let out. “You’re so tight, baby.”

He started moving. Hard, steady rhythm, both hands gripping my hips, pulling me back each time he thrust. The bed creaked. His balls hit my skin with every stroke, a wet, rhythmic sound filling the bedroom. I clung to the sheets without knowing which part of my body to attend to first: the spinning head, the trembling knees, the chest that never quite finished breathing.

“Tell me you like it,” he asked without slowing down.

“I like it,” I panted. “I love it. Harder, come on.”

He fucked me harder. He planted a hand between my shoulder blades and pressed me into the mattress, leaving my ass raised, and he took me deeper, each thrust making me see stars. My own cock, forgotten between my legs, let out a thread of fluid without my seeking it, without me being able to do anything, like a body doing what it can when the mind no longer rules it. I felt that long shudder rise up from inside me, from where he was touching me with the tip every time he pushed in, and I came like that, hands-free, spilling onto the sheet in spasms that shook my whole body.

“Oh, God,” I whispered. “Oh, God.”

Then I cried.

I don’t know why. It wasn’t sadness or regret. It was something that still had no name, something that had been building up for a long time in a place I didn’t know existed and that night finally found a way out. He didn’t stop. He kept fucking me, slower now, deeper, and I cried into the pillow while he filled me again and again.

Ramiro gripped my hips with his hands, hard, sinking his fingers in until they left marks, and came inside me with a long moan and a sound only I got to hear from within. I felt each hot spurt hit me inside, one, two, three, while he pushed all the way in and stayed still, pressed against my ass, trembling inside me.

***

We stayed still for a moment, him still inside me, his weight pressing me into the mattress. Then he pulled out slowly, carefully, and I felt a hot thread of his semen escape from my open ass and run down my thigh. He lay down beside me.

He didn’t ask me why I had cried. He just put a hand on my back and left it there, still and warm, while I caught my breath and the world regained its usual edges.

Outside, the neighborhood was still the same. The neighbor’s music, the distant noise of the avenue, some car passing by. The world that knew nothing about us.

Inside, with him by my side and his hand on my back, I was exactly what I had always known I was.

Valentina