My First Date as Myself at Last

Hi, my name is Renata. I’m thirty-one years old, and this is the first time I’ve dared to write here, even though I’ve been reading all of you in silence for a long time. Today I finally gathered the courage to tell you how my first time with a man went, my first boyfriend, and the night I stopped hiding and gave myself over as the woman I always knew I was.

From a very young age I felt there was something different about me. I didn’t look like the other children my age. What really caught my attention was women’s clothing, that softness, those colors, the way it fell over the body. I have a younger sister, barely a year and a half younger than me, and it was with her things that I began to discover all this. I would try on her dresses when no one was home, look at myself in the mirror, and for the first time recognize myself.

That was how I grew up, between fear and desire. I had the occasional encounter with boys from the neighborhood, but it never went beyond a caress or a quick, nervous blowjob, always with guilt nipping at my heels. I turned eighteen and started working driving freight trucks along the southern highways. At last I had my own money and, above all, my own freedom.

I’ll never forget the first time I went into a store alone to buy women’s clothes for myself. My hands were shaking. I felt like everyone passing by me knew what I was doing, like they could read it on my face. I left with a bag full of things: a couple of lingerie sets, a dress, and a chestnut-brown wig that fell a little below my shoulders. I walked back to my parents’ house clutching the bag to my chest as if I were carrying a stolen treasure.

I ran to my room and shut myself in to try everything on. I put on the wig, the dress, looked at myself, and something inside me finally clicked into place. Because of work I was almost never home; I came back on weekends, sometimes not even then. But little by little I started wearing women’s underwear every day, under my men’s clothes, in the truck cab, at roadside stops. It became the most natural thing in the world. No one had seen me transformed yet, and a couple of times they almost caught me at home, but luckily I always managed to hide it in time.

Until one day the message arrived that changed everything.

***

It was strange from the start, because he wrote to my male account, not the other one, the one I used as a woman. He was a guy. The message began with a simple “hi,” nothing more. Before replying I checked his profile carefully. The truth is he was handsome: broad shoulders, a confident smile, that kind of gaze that unmans you. So I worked up my courage and answered him.

After just a few sentences he came right out with it, no beating around the bush. He told me he’d seen me passing through the town several times and that he liked me. I was speechless. It took me a couple of days to know what to say, and when I did I confessed to him that I liked men too. His response was immediate: he wanted to meet me in person.

I told him yes, but that it would take me a while to get there because I was out on the road with the truck. And before going any further, I made the most important thing clear: that I transformed into a woman, that that was my truth, and that I was still a virgin. I blurted it out all at once, heart in my throat, sure that would be the end of it.

He took a while to answer. So long that I thought I had scared him off, that I’d never hear from him again. But after a very long while his message appeared. He told me he had never been with someone like me, that he had only been with men, and that even so he still wanted just as much to meet me. I read those lines three times. I couldn’t believe it.

Several days went by before we could see each other. In that time we wrote to each other every hour, we called each other on the phone until we fell asleep with the cellphone against our ear. Suffice it to say I agreed to be his girlfriend over the phone, like that, without us ever having met in person. Crazy, I know, but by then we told each other everything. His name was Damián, and his voice had worked its way into every corner of my days on the road.

At last I got the news that I’d be off for a few days as soon as I got back from my last trip. As soon as I hung up with the boss, I called my love.

—Hi, baby, guess what? I’ve got amazing news —I said, unable to hold back my smile.

—Let me hear it —he answered.

—I’m finally getting a few days off. And I’m dying to see you in person.

—That’s great, beautiful. At last I’m going to have you right in front of me —he said, and I felt my knees go weak just hearing him.

***

We agreed to meet the day after I arrived, so I’d have time to get ready calmly and prepare everything I was going to bring. I knew that day no one would be at my parents’ house: they were going to a party and would be back late. I went straight to take a long bath, carefully shaved off the little body hair I had, put scented creams all over my body, and sat in front of the mirror to decide what to wear for my first real date.

I chose a black thong, bra, and garter belt set, with sheer stockings that clung to my legs. I borrowed my sister’s heels without asking, brushed the wig, did my makeup, and finally put on a black dress so short it barely covered the top of the stockings. That night I hardly slept from nerves. I tossed and turned in bed imagining what it would be like to have him close.

When I woke up, I already had a message from him. He told me how anxious he was, that he hadn’t been able to sleep either. I didn’t really understand what was happening inside me, but I think I was falling in love, and that even though I hadn’t even seen him in person yet. Then he wrote again: his parents had taken the car and he asked me, if it wasn’t a problem, to come pick him up.

I said yes, delighted, though it changed my plans. I had intended to wait for him already transformed into Renata. So I put on all the lingerie and the dress under my men’s clothes, so I wouldn’t waste time when I got to the hotel and could finish getting ready quickly. We lived in the same town, so the trip was short.

When I got to where he was waiting, I slid into the passenger seat so he could drive and take me wherever he wanted. On the way, from sheer nerves, we barely spoke. He stopped to buy a few beers and we carried on. My stomach was in knots, and I kept glancing at him out of the corner of my eye, thinking that in a little while I was going to be naked in front of a man for the first time in my life.

We got to the hotel and I went straight to the bathroom to finish getting ready. I took off the wig, touched up my makeup, adjusted my dress, and took a deep breath. When I came out, he looked me up and down. I was the one who broke the silence.

—How do I look, love? Do you like me? —I asked, playing with the hem of my dress.

—You’re beautiful —he said, never taking his eyes off me—. If I hadn’t seen you a while ago as a man, I wouldn’t recognize you.

—Are you saying that seriously, or just so I won’t feel bad? —I insisted, still unsure.

—It’s the plain truth. You’re gorgeous. And your body? I won’t even start.

***

I sat on the edge of the bed and he came closer with a beer in his hand. I accepted it and, from nerves, drank it too fast. We laughed. We had a couple more while talking, and little by little the room filled with that tension you feel in your skin before something happens.

Suddenly I saw him lean toward me. He kissed me. It was a slow, deep kiss, so delicious I couldn’t resist and kissed him back, pressing my body against his. Our tongues searched for each other while his hands started roaming over my dress, slowly sliding down to my legs. I didn’t stay still: I pulled off his T-shirt and ran my palms over his defined chest.

He already had one hand under my dress, squeezing my ass. The intensity rose every second. By the time I realized it, he had already taken off my dress and I had opened his pants, feeling his hard erection over his boxer briefs. He lay back without stopping the kiss for even an instant.

I stopped kissing him and started making my way down his body. I kissed his neck, his chest, his stomach, until I reached his boxer briefs. I slid them off very slowly and took his sex into my mouth as best I could, discovering what a man’s desire for me tasted like. I sucked him with eagerness, looking up at him from below, until he stopped me.

—Stop, beautiful, you’re going to make me finish like this —he said, breathless—. And not yet. I want to enjoy you all the way.

He handed me a condom and I put it on him myself. Then he made me turn face down and pulled my thong down with a slowness that drove me crazy. I felt his tongue between my ass cheeks, at my still-virginal entrance, and a moan slipped out of me that I couldn’t hold back. The arousal was so intense I couldn’t take it anymore.

—Please, put it in already —I begged him, trembling.

He settled over me and started entering little by little. It hurt, it hurt terribly, because he was not small at all. I bit my lip and breathed, letting my body get used to that intruder who was taking me over. After a while he managed to get all the way inside me and stayed still, giving me time. Then he began with a gentle, patient back-and-forth until I felt him about to come. He got off me and lay back on the bed, panting.

I, still sore, curled up against his chest. It was only a moment before I kissed him again, whispering in his ear how much I had liked it, how good I felt with him. While I kissed him, I lowered my hand and started stroking him. I felt him harden again beneath my fingers.

—Do you have another condom? —I asked him.

—No, that was the only one —he said.

Lust won out over caution. I climbed on top of him and started sliding him into me myself, slowly, until he went in all the way. I began to move at my own pace, master of my own pleasure for the first time, feeling him breathe harder beneath me. I rode him until I noticed he was about to come again, and this time he filled me inside. I pulled him out slowly and cleaned him with my mouth, looking him in the eyes.

***

We stayed a little longer, wrapped in each other’s arms, kissing without hurry, until reality reminded us that we had to leave. We got dressed in silence, stealing glances, and went out. I dropped him off where I had picked him up. It was already getting dark, and not caring who might see us, we said goodbye with a long kiss I still remember.

I hope I haven’t bored you with this little story. For me it was the night I stopped hiding and finally became myself, completely, without masks. Very soon I’ll tell you about the next time I saw my love, and also another even more intense story: that of that married trucker of whom I was secretly his woman for quite some time. But that, darlings, will be on another occasion.