I Traveled Three Hours Dressed as a Woman for a Stranger

My name is Dafne, and this is one of those stories I never told anyone. Today I live with Mauro, my partner, and I’m happy in my own way: we argue over nonsense, make up in bed, and he has no idea what I write. I don’t think that’s disrespectful. They’re my memories, from before, from when he didn’t exist yet.

There was a time when I didn’t have anyone steady. One-night stands, two at most, and then silence. I didn’t complain: I needed sex the way you need air, and I got tired of waiting for it to come on its own. So one dawn, without thinking too much, I typed up an ad on one of those contact sites.

Closeted transvestite looking for a mature friend to have a good time with.

I posted it and went to sleep. The next day my inbox was full. Most of them were horny guys who wanted everything for free and yesterday, one-line messages, photos with no context. I deleted almost all of them. But there was one different: a man who introduced himself by name, who wrote in full sentences and, instead of demanding anything, left me his phone number.

I called him that same afternoon. His name was Rodrigo, he had a calm voice, and he owned a small fleet of trucks in a city three hours from Trujillo. He sent me a photo: a forty-eight-year-old man, broad-shouldered, with that kind of confidence you can’t fake. We talked for almost an hour. He didn’t promise me anything impossible, and oddly enough, that was what made me trust him. We agreed on the day and time, and the following Thursday I got on a bus with my heart pounding against my ribs.

***

He was waiting for me at the terminal. I recognized the pickup before I recognized him: double cab, windows so dark you couldn’t see anything inside. I offered him my hand in greeting, formal, and he grabbed my arm and kissed me on the mouth right there, in front of everyone. It startled me so much I went breathless. Then I got embarrassed, and then a warm current ran down my back.

—Get in the back —he said, opening the door—. Dress in peace while I collect from a couple of clients. No one will see you.

And he was right. Behind those windows I was invisible. I took off my travel clothes and slowly transformed myself: the stockings, the black lingerie, the dress I had chosen thinking of that moment. While Rodrigo went in and out of offices and storage rooms, I finished painting my lips in the little mirror on the sun visor. When he came back for the fourth time, I turned to him.

—I’m ready now —I told him.

He looked me over for a long, long second.

—Look at the doll I’m taking home —he murmured.

***

The hotel was large, one of those with an inner courtyard and several cars parked in it. It was two in the afternoon. Rodrigo got out first, opened the door for me as if we were on a formal date, and gave me a slow kiss before walking toward the rooms. It was the first time I had crossed a place like that, in daylight and dressed as a woman. I could feel the employees’ eyes stuck to the back of my neck, to my legs, to every step I took in my heels on the polished floor. I walked in red up to my ears. And at the same time I enjoyed it like few things in life.

As soon as he closed the door he grabbed me by the waist. He didn’t let me say a word. His mouth found mine and our tongues tangled, first slowly, then with urgency. He pushed me onto the bed and climbed on top of me. He wasn’t tall, but he was solid, and he had a strength that turned me over as if I weighed nothing. He took off my dress and left me in black lingerie, running his hands over that white skin that always drove them wild.

He undressed. What he had between his legs made me swallow hard: thick, firm, more than I was used to. I took it in my mouth and at first it was hard; I had to go slowly to get used to it. I ran my tongue over the head, went all the way down, lingered there while I dug my nails into his ass. When I came back up and took it all again, I heard him moan for the first time.

I got bolder and ran my tongue lower still, where no one usually dares to go. I thought he’d get annoyed.

—That feels so good —he said instead, his voice breaking—. No one’s ever done that to me.

That lit me up. I kept going, heard him holding his breath, felt him shiver under my hands. Then he turned me over and it was his turn: he sucked my nipples, my neck, the lobe of my ear, then kept going down until he had me moaning so hard I was startled by the noise myself.

—Lower —I asked, and I didn’t even recognize my own voice.

He put me face down. He kissed my back, my shoulders, left a wet trail until he parted me with his hands and used his tongue where his cock filled me with fear and desire in equal measure. He worked me like that for quite a while, until he heard me relax. Then he pulled a condom from his pants pocket, put it on, and lifted my legs.

—Slowly —I managed to tell him.

—Slowly —he repeated.

And he kept his word. He pushed in little by little, watching my face, asking with his eyes more than with words whether it hurt. It hurt and I liked it at the same time, that mix you can’t explain to someone who doesn’t know it. When he was halfway in, he pulled out, got everything wet again, and on the next push he went all the way to the hilt in one go. He tore a cry out of me. He stayed still, letting me breathe, kissing the nape of my neck while I got used to having him all the way inside me.

Then he really started moving. In and out, hard, nonstop. My moans slipped out from under the door and by then I no longer cared who heard them.

—Tonight you’re mine —he told me in my ear, and I nodded into the sheet.

He changed my position several times. On my knees, face buried in the pillow and hips raised, standing over me looking for another angle, on top of him riding him slowly. He lasted more than an hour, tireless, until I felt him tense all over. He pushed deep, stayed inside, and I could feel him throbbing when he came. With him still inside me, I touched myself until I reached my own orgasm and left marks on his chest.

He pulled me against his body. He kissed my forehead, held me in his arms for a long while, in silence, until he let go and I went to the bathroom with my legs shaking, aching, and absurdly happy.

***

He ordered food and a bottle of wine to the room. I liked that detail, that he remembered I ate too, that I wasn’t just a rented body. We ate in bed, talking about anything, and fell asleep almost without realizing it.

I was woken by his phone ringing. For a second I didn’t know where I was. When I saw him beside me, I got my bearings. He had to leave: work was calling him. But before he went, he asked me for one last thing, in a low voice, almost shy for a man like him. I gave it to him calmly, unhurried, and when he finished he kissed me as if we had all the time in the world.

—There’s no time to shower —he said while getting dressed—. But don’t worry. In a little while one of my trailers is leaving for Trujillo. It’ll take you right to your door.

We left the hotel the same way we had arrived, me dressed as a woman and my head held high this time. On the way to the truck yard, he took several bills from his wallet and put them in my hand.

—Thank you for coming —he said—. I had a better time than I have in years.

I put the money in my purse without counting it. When we reached one of the trailers, he called the driver over.

—Take her to Trujillo, nice and easy —he ordered, and squeezed my hand one last time.

***

It was eleven at night. Already in the cab, in the dark, I took out the bills and counted them: much more than I would ever have asked for. The driver was young, rough around the edges but polite, and he drove with both hands glued to the wheel as if he were afraid to look at me. He offered me a soda. We talked. He asked me about his boss and I told him just a couple of things, the least compromising ones.

I asked him to stop somewhere along the road so I could wash up and change, because I couldn’t get to my neighborhood dressed like that.

—Don’t worry —he said without taking his eyes off the road—. I’ll drop you right at your door.

I lived alone, luckily, and right off the route he took. Halfway there he stopped at a gas station to buy cookies. When he got back in, he handed me one and, doing so, left his hand on mine a second too long. I know what he wants, I thought. But he wasn’t daring to say it. I looked at him until he got nervous.

—Do you like me? —I asked him outright.

—I wanted to kiss you —he confessed, staring ahead.

I kissed him first, long and slow, without him having to ask twice. He put his hand on my thigh and suggested we move to the sleeper cab in back. Before that I asked to get down and wash; I poured water from the jerry can onto myself on the side of the road, in the dark, laughing alone at how absurd the night was. Then I climbed back up.

He was different from Rodrigo: longer, but skinny, and hard as few men I’ve seen. I put a condom on him and he took me in several positions, pounding deep, deeper than my already sore body could stand. I complained, it hurt, and even so I didn’t ask him to stop. He finished inside me; when he pulled out, the condom stayed inside and I had to fish it out myself. We got dressed and the trip continued, now with a new sense of trust between us. He caressed my face, told me I was beautiful, that he hoped it wouldn’t be the last time.

Three hours later he stopped in front of my house, right on the highway. Before I got out, he kissed me and, just before I reached the door, wrote his number down on a piece of paper. I had two more encounters with him after that night, but that, friends, is another story.

I remember this one in full: the ad, the trip, the stranger who ended up treating me like a queen, and the shy guy on the way back. One hundred percent real, like everything I write. In a few days I’ll tell you the next one. Kisses.