The Transvestite Carlos Didn’t Expect to Take Home

There are times when life forces me to go disguised as something I’m not. Not out of shame, but for convenience: certain business meetings require me to show up as the man listed on my documents, without a wig, without makeup, without the heels that make the way I walk completely different. That day I’d had one of those meetings and, when it ended, my friend Héctor and I decided to have dinner at a restaurant I’d been going to for years, a few blocks from my apartment.

We got there around nine. The place had dark wood tables, soft music that didn’t interfere with conversation, and a menu with decent dishes at reasonable prices. We ordered beers and something to eat, and while we waited, I noticed a man sitting alone two tables away.

He must have been about fifty-five, maybe a little older. Broad build, graying hair, a jacket that suited him well. He wasn’t the kind of man who needs to attract attention because he already has it. He looked at me a couple of times without insisting, without it ever becoming completely clear whether he was looking at Héctor or me, and went back to his plate.

After the third beer, I started looking back at him. Héctor told me later, laughing, that I don’t know how to look any other way except flirtatiously. He’s right, and I see no reason why I should change.

A while later the waiter came over with two more beers and pointed toward the man’s table.

“These are from Mr. Carlos,” he said.

We thanked him with a nod and invited him to come over. He accepted without hesitation. His name was Carlos, he worked in imports, and he’d been single for a long time. He said it all with the ease of someone used to lonely restaurants and brief conversations with strangers. We talked about unimportant things: the heat over the last few days, traffic downtown, a soccer match they’d broadcast that week.

Carlos spoke more with me than with Héctor. We both noticed. Héctor took it humorously. I took it attentively.

At one point, the subject drifted toward fashion and bodies. Carlos made a comment about women who were too thin, said he didn’t understand that obsession, that he preferred real curves, and as he said it his eyes dropped for a moment to my chest. It wasn’t a rude gesture. It was a quick look, almost involuntary, followed by a slight unease he didn’t quite know how to hide.

What Carlos couldn’t know is that my breasts are hard to conceal. I wear a 40C, and no men’s shirt can completely neutralize that volume. Some people notice and look away. Carlos noticed and kept looking.

Héctor finished his beer, checked his watch, and announced that he had to go. It was a lie, and we both knew it, but I was grateful. We hugged, he shook Carlos’s hand, and left us alone.

When Héctor disappeared through the door, there were a few seconds of silence that Carlos broke by asking if I lived nearby.

“Three blocks away,” I told him.

“Would you mind if I asked you an indiscreet question?” he said.

“Depends on the question.”

He asked me if I had ever been with a man. I told him yes, quite often. He kept looking at me with an expression that mixed surprise with something more interested.

“Would you like to have a drink at my apartment?” I offered. “I’ve got brandy.”

He accepted.

***

We walked up. Carlos walked beside me unhurriedly, with that calm of men a certain age who no longer need to prove anything. In the elevator we were silent. I could feel him watching me from the corner of his eye, as if trying to guess what was beneath the clothes that still clung tightly to my body.

At the apartment I poured him a glass of brandy and put on music. I wondered how long it would take him to ask the question that had been hovering since the restaurant.

It didn’t take long.

“Do you have another name?” he said, glass in hand. “One you use... in other contexts.”

“My name is Valentina,” I replied. “But only when I’m really myself.”

He was silent for a few seconds, looking first at my face, then at my mouth, then at the defined outline of my breasts beneath the fabric.

“I’d like to meet Valentina.”

Who in their right mind says no to that?

“Give me ten minutes,” I told him. “Make yourself comfortable.”

I locked myself in the bedroom. I took off my clothes, changed, and did my makeup quickly but carefully: foundation, red lips, mascara. The chestnut wig that falls to my shoulders, slightly wavy. I put on the set I kept for occasions like this: red lingerie, black lace stockings, satin garter belt. Over it, a short black silk robe that covered everything without hiding anything. I looked at myself in the mirror, lifted my bust a little with my fingers, adjusted the neckline so it sat exactly where it should, and perfumed my neck, my chest, and the insides of my wrists.

I went out into the living room without warning.

Carlos had his back to me, looking at the window. He turned when he heard the heel on the parquet floor and completely lost his composure. He stood up. Opened his mouth. Closed it. His eyes dropped shamelessly to my legs, lingered a second too long on the stockings, and then rose slowly, as if he didn’t know whether to keep looking or kneel.

“Is that you?” he said.

“I’m Valentina,” I told him. “Did you want to meet me?”

It took him a few more seconds to react. Then he let out a short laugh, almost relieved, and said yes, he did. I came closer, took his glass from the side table, and put another one in his hand. We toasted. When his fingers brushed mine, I noticed the slight tremor in his hand, and that excited me more than I would have liked to admit.

I changed the music for something slower. I took his hand and we began to dance. He was quite a bit taller than me even in heels, and his arms circled my waist with a firmness I hadn’t expected. I felt his breathing change the moment I pressed myself against his body. My chest brushed his torso with every turn and he began breathing through his mouth, with an evident tension in his crotch that he didn’t need to confess to me.

And I felt, too, that I was not indifferent to him.

***

I kissed him first. I caught his mouth hungrily, opening his lips with my tongue until I could taste the brandy and beer mixed in his breath. Carlos responded with a pressure that said more than he probably would have wanted to admit. His hands moved from my waist to my hips, and I undid the first button of his shirt while he explored the curve of my back, the line of the garter belt, the narrow waist beneath the silk.

I slipped my hand between us. I found him hard, pretty hard, and thick too. I lowered the zipper slowly and took him over the fabric, massaging his cock with my palm until I felt it swell even more against my hand. The bulge was hot, tense, and the fabric of his pants could no longer hide how soaked the head was.

“Sit down,” I told him.

He sat on the sofa. I knelt before him, gathering the skirt of my robe so I wouldn’t get tangled up, and undid his pants unhurriedly, enjoying the eager tug of his hips toward me. I lowered the fly, opened his underwear, and revealed that thick, compact cock, with a slight curve and a pink tip shining with moisture. I took it in my hand, squeezing at the base, and stroked it up and down a couple of times before bringing the head to my mouth.

I wrapped my lips around it slowly, sucking the head first, then gradually sliding my tongue underneath the frenulum. Carlos let out a low moan and put a hand in my hair, not pushing me at first, as if he needed permission to touch me. I gave it by opening wider, taking him as far as my throat would allow and setting the rhythm with my tongue on every pull back.

I worked without rushing. He breathed faster and faster. I ran my mouth along the shaft, sucking hard at the tip, licking the throbbing vein underneath and squeezing the base with one hand so it wouldn’t slip from me. When he tried to warn me, I changed the rhythm on purpose, alternating slow sucks with short, wet movements, letting him grind against my tongue until he began to lose control.

“Valentina,” he said, his voice tight. “You’re going to make me... wait...”

I didn’t wait in time. I sucked harder, deeper, and he came with a spasm he couldn’t control, hips lifting off the sofa and fingers tangled in my wig. I felt the hot load burst in my mouth and swallowed almost all of it, using my tongue to gather what remained at the tip so nothing would go to waste. Carlos was left leaning back, speechless, eyes closed and chest rising and falling as if he had just run a marathon.

“I thought we were going to make it to the bed,” I told him.

“Me too,” he answered, still without opening his eyes.

I wiped the last drop with my thumb and sucked it slowly, looking at him so he would understand he had nothing to be ashamed of. When he finally opened his eyes, he was hard again already, faster than I would have expected. I smiled and gave his thigh a soft pat.

***

I took him to the bedroom. I took off his shirt slowly, kissing his neck, his chest, his stomach. He had the body of a man who once worked with his hands: broad shoulders, plenty of chest hair that I tangled my fingers in as I went down. I ran my tongue over one nipple, then the other, and felt him tense under my mouth. His skin smelled of soap, alcohol, and hot man.

When I reached his crotch again, I found him recovering. I gave him attention until he was ready again, sucking his cock patiently, using more tongue, sealing my mouth around the head until I drew another deep groan out of him. I licked his balls, stroked them with my hand, brought him to the edge and then pulled away, just to watch him tremble with frustration and desire at the same time.

I lay down on top of him. We kissed for a long time while I took off his pants and he searched for the tie on my robe. When he pulled it off me and saw the full lingerie —the sheer bra, the garter belt, the stockings— he murmured something I couldn’t understand but that sounded like approval. His fingers traveled along my thighs, the edge of the stockings, the curve of my hips, until they reached the wet center of my panties.

He sucked my nipples. They’re very sensitive, and I had to bite my lip not to make too much noise. His hands held me by the waist and his fingers explored downward, backward, until they found what they were looking for. He parted my ass cheeks carefully, rubbed around my hole, and when he realized I was already open and hot he slid a finger in slowly, then two. I arched over him, clutching his shoulders, and kept kissing him so I wouldn’t lose my mind while he prepared me.

When I felt I was ready, I had him lie back and climbed on top of him. I guided his cock with my hand, setting the tip against my wet entrance. I lowered myself slowly, pausing, letting my body adjust to the thickness of that head before continuing. Carlos had his teeth clenched. So did I. Every centimeter that went in stretched me inside with a mixture of pleasure and burning that made me let out a long moan.

I stopped halfway. I breathed. I dug my nails into his chest and he looked at me as if he didn’t want to break the moment.

Then I let myself down the rest of the way.

The sound Carlos made was involuntary and honest. I stayed still for a few seconds, feeling how my cunt readjusted around that thick, hot, throbbing cock, and then I started moving. Slowly at first. Then more decisively. Carlos had his hands on my hips, gripping me hard enough to leave marks, but I set the pace, and he was smart enough to understand and let himself be carried along. I leaned forward, braced my hands on his chest, and found the angle I needed to feel him rubbing inside me with every descent.

It was long. Intense. I lost myself in it completely. He thrust up from below with short, deep drives, and I answered by moving my hips, rising and falling on his soaked cock, feeling pleasure fill my pelvis, my belly, my throat. He kissed my breasts, bit one nipple, and I took his face in my hands to force him to look at me while I told him to keep going, not to hold back, that I wanted to feel every inch of that man inside me.

***

When I changed positions it was because I wanted to feel him closer. I turned onto my side, he settled behind me, and we kept going for a while with his hips hitting mine in a slow rhythm that sped up on its own. His lips on my neck. His hand around my waist from the front. His other hand sliding up my thigh to open me wider, searching for more depth, more friction, more of that wet rubbing that had us both on the edge already. Every thrust made his cock rub inside me with delicious pressure, and every time he brushed my most sensitive spot I trembled from head to toe.

I felt myself getting close and asked him to stop.

“Did I hurt you?” he asked, stopping abruptly.

“No,” I told him. “I want another position.”

I got up, had him lie back down again, and gave him a few minutes of oral attention to keep him where I needed him to be. I sucked his cock hungrily, alternating mouth and hand, taking him all the way down on every descent and letting the wet sound fill the room. Then I got on all fours on the bed, knees apart and ass offered up, feeling the cool air on my skin and the heat between my thighs.

I didn’t say anything. There was no need.

Carlos positioned himself behind me, took my waist with both hands, and entered in one motion. Deep. Decisive. Without hesitation. The first thrust tore a clean cry from me, because he opened me all at once and filled me completely, the head of his cock driving all the way in and leaving me trembling on the sheets.

I rested my head on the pillow and closed my eyes. I felt him holding my ass hard, opening my cheeks to get in better, the brush of his pelvis against me making everything slippery and urgent again. He fucked me from behind without restraint, with firm movements that made the bed creak, and I answered by pushing my ass back against him to ask for more. Faster. Harder. Deeper.

What came after that I have no way of describing in an orderly fashion. I only know that at some point I screamed, that Carlos didn’t stop, that I reached the limit and stayed there for a time I couldn’t measure, and that when he finally came too I felt him inside me exactly as I wanted to feel him: completely, without reservations. His body went rigid all at once, his breathing turned into broken panting, and he filled me with a hot load that made me clamp my thighs together and stay still for a moment, savoring the sensation of having him still buried in me.

We stayed still. He let his weight fall on me without crushing me. We breathed together for a few minutes before moving. When he finally came out, I felt the wet, sensitive emptiness left by a good fucking, and I had to turn to kiss his mouth again, still trembling.

***

We fell asleep late. Before dawn we started again, slower this time, unhurried, as if we had both tacitly agreed there was nowhere to get to. I straddled him and rode him again, letting him fill me while I stroked his chest and kissed his throat. We changed rhythm, angle, breath, until the room was once again filled with our low moans and the wet sound of our bodies colliding.

Carlos left shortly after daylight broke. At the door he told me he wanted to see me again.

“I can put you on the list,” I told him. “But fair warning: it’s a long one.”

He laughed. He kissed me once more.

I’ll never forget that night in the restaurant, the beer he sent over without knowing anything about me, and the look on his face when Valentina appeared in the living room.

Some surprises are worth it.