I Dressed as a Woman for My First Time with Him

A couple of days had passed since my last encounter with Darío. I had just turned nineteen, and after discovering so many new things about myself, I felt hungry to keep experimenting. Not a day went by that I didn’t touch myself imagining it was him doing it, his large, slow hands tracing the small of my back.

The days kept passing and Darío still wasn’t contacting me. I called him a couple of times, but he always sent me straight to voicemail. I felt neglected, ignored, and still wanting more. Since I already had some women’s underwear, there were mornings when I went to college wearing a lace thong under my pants. I spent hours in class with a tingling between my legs, ashamed and turned on at the same time by the thrill of knowing no one suspected what I had hidden.

I started watching my classmates, hoping to feel something, but nothing happened. Apparently, my type was older men, the ones who already knew what they wanted.

I started saving money. I was planning to go to a market in a nearby city and buy myself real clothes, something sexier, bolder, something that would let me fully explore the woman inside me. After Darío ignored me all week, the following Saturday I fantasized about putting female clothes under my male clothes and going out to find someone on my own. The idea of finding a mature man willing to do anything to me excited me.

I was ready to leave when the phone rang. It was Darío. He told me he’d had an impossible week and was dying to be with me again.

—This week we’re seeing each other one way or another —he promised—. This time we won’t have to worry about getting caught. Wait for my call.

I told him that was fine, that I’d be waiting eagerly.

I don’t know if it was some kind of loyalty to him, but that Saturday I decided to stay home. Still, I took advantage of the chance to put on some feminine clothes under my regular outfit and went downstairs to spend some time with my family. I sat down to watch a movie with them and felt strangely comfortable. None of them suspected what their supposed son was wearing, and that made me feel like I was one more daughter.

***

Later I went up to my room. I asked my sister if she’d lend me her laptop, since she was heading out, and she said yes. It was an ideal day to browse the internet. Before social media took over, there were chat rooms, where you could talk to hundreds of strangers at once. I set my nickname to CamilaTv and entered a room dedicated to girls like me and the men looking for them.

I just wanted a little dirtiness. I wrote in the main room that I was looking to chat and said what city I was from. Several private messages came in, but the one that caught my attention most was from a guy whose nickname was ElDomador80. He told me he was thirty-seven and from the same city as me. After I told him my age, what I liked, and what I wanted to do, he replied that he’d give me all that and more.

—I’ll do all that to you, little girl, and even things you can’t imagine. You’re going to be thrilled with me —he wrote.

—Yeah? And what exactly are you going to do to me? —I replied.

—First I’ll put you on all fours, eat that little ass of yours, and then I’ll give it to you whole, right down to emptying myself inside you.

The way he talked to me was rough. Darío was much more gentle, but since it was over the internet I assumed it would all stay a fantasy, so I let myself go with it. I have to admit that kind of talk turned me on.

—But I’m a first-timer —I wrote—. It’s going to hurt.

—Don’t worry, I’ll make it feel really good. You’re going to like it so much you’ll end up asking me for more.

—And where would you do all that to me? At your place? A hotel?

—At your place, girl. Right there, in your bed, I’ll make a woman out of you.

I didn’t want to admit it then, but the idea of him coming to my house to turn me into a woman lit me up. That made me bolder in the conversation.

—Sounds tempting —I wrote—. Right now I’m in my room, dressed like a girl, but my parents are here. I don’t think it can happen.

—When they’re asleep, let me know. I’ll come, make you mine, and leave. Nobody has to know. And if they do, let them see they have a very pretty, very bold daughter.

I thought about it. Waiting until everyone was asleep, sneaking him in, letting him have me in my own bed. If I was careful, no one would notice.

—Go on —he insisted—. Are you in or not?

—I don’t know, I’m scared they’ll catch me.

—You’re going to regret not feeling my ten inches in that little ass of yours. I’ll turn you into a real little woman.

I don’t know if the size was true, but what I do know is that imagining myself in that situation left me soaked. I closed the chat, turned off the laptop, and lay down on the bed. With a little baby oil, I started touching myself, imagining ElDomador80 coming into my house and making me his, no matter that my parents were nearby.

***

At college, the semester’s final exams were approaching. Classes were being reduced to taking the test and going home. I usually went off with friends to play pool, but this time I decided to head straight back to keep saving money.

On Friday, after the exam, I traveled to a market in a neighboring city, about forty-five minutes away by bus. I put on a hoodie to go unnoticed and tried to cover my face. The market was huge. I carefully checked the stalls, not only looking for pretty clothes, but also for one staffed by an older woman I wouldn’t feel embarrassed buying from.

I found one full of lovely clothes, run by a woman in her forties or so. She said the clothes had been brought from abroad, perfect for giving to a girlfriend. I wanted to make the purchase quickly: I chose a short black dress with embroidered yellow flowers, a pink silk nightdress with black details, and a set of pink lace underwear that looked beautiful. It all cost almost everything I had on me, but it was worth it.

—Your girlfriend is going to look beautiful in this —the woman told me.

—Yes, absolutely —I answered with a nervous smile.

—Come back soon, I’ve got more lovely things at a good price.

I left almost running and spent much of the night modeling the dress in front of the mirror.

***

The next day, Saturday, I knew Darío would call me, so I was anxious. That morning my parents announced they were going to a wedding with my grandparents, in a town on the outskirts of the city, and that they wouldn’t be back until Sunday night. I was thrilled. When they said my sisters were going too, I nearly jumped for joy. They asked if I wanted to go with them, and I used my exams as an excuse: I said I was exhausted and had essays pending. They accepted without a problem.

All afternoon I called Darío, but he kept sending me to voicemail. It didn’t bother me too much: if he didn’t show up, I could always go back to the chat and look for someone like ElDomador80.

At six in the evening everyone left. As soon as I closed the door, I went to shower. I made myself flawless, using my sister’s scented soaps to feel more feminine. I knew it was a decisive night, so I kept calling. After several tries, Darío finally answered.

—Did you call me a lot? —he asked.

—Just a few times —I lied—. Hey, do you want to come to my house? There’s no one here. I want you to see me in the sexy clothes I bought.

He stayed silent for a few seconds, disbelieving, but when I assured him the house would be empty until the next day, he agreed. He said he’d be here in forty-five minutes.

I started getting ready. I put on the pink lace set that made my hips stand out, then the short dress. Just then he called to say he was outside. I opened the garage so he could pull the pickup in and asked him to wait in the living room, that I wouldn’t be long.

I went to my sister’s room, put on some of her creams, a bit of makeup, and a few drops of her perfume. I adjusted the wig Darío had given me and, at the end, a little bow as an accessory.

When I looked in the mirror, I no longer saw the boy who hid in his sister’s clothes. This time I saw a whole woman. This is the real me, I thought, and went downstairs to surprise him.

***

As soon as he saw me, the first thing Darío said was that I was beautiful, that he couldn’t believe how good I looked. I stood in front of him, turned a couple of times so he could admire me, and sat on his lap. Before he could say anything else, I kissed him. I wanted to devour him with kisses. Feeling his hands moving up my thighs made the urge to take him to bed grow nonstop.

—And your parents? —he asked between kisses—. I want to keep going, but I’m worried they’ll come back and catch us.

—Do I look pretty? —I replied, ignoring him.

—You’re gorgeous, Camila.

—Then I don’t care if they come back. Let them find out they have another daughter.

I slid my hand down to his crotch. He was hard. I tried to unbutton his pants, but he resisted, saying it wasn’t safe. I whispered in his ear that my parents wouldn’t be back until the following night. He only smiled. I opened his pants, pulled out his cock, and bent down to kiss it slowly; it had been a long time since I’d had it in my mouth. It felt harder than other times. Darío was enjoying it like never before.

I paused and stood up so he could look at me again.

—Where did you get that dress, baby? —he asked.

—I went to a market. I wanted to surprise you with something sexier.

I turned around and lifted the dress so he could see the lace lingerie. His gaze fixed on my ass. In his eyes it was clear that tonight he was going to make me his. I sat back down on his lap and, while I stroked him with one hand, I kept kissing him.

—Did you bring a condom? —I asked.

—Yes, I brought several.

—Do you want to come up to my room and make me your woman?

He didn’t say a word. He only smiled, stood up, went to the pickup for the condoms, and came back with a small digital camera. I took his hand and led him toward the stairs, but before that we stopped in front of the hallway mirror.

—Take a picture of me —I asked—. To remember the day I become a woman.

He hugged me from behind and snapped the shot. Then we went upstairs. My room was the room of any college student, but from that night on it would be the place where I gave my virginity to an older man.

I lit some candles, turned off the light, and settled back on the bed. I stretched out my arms for him to come closer. While he kissed me, I opened my legs and tried to trap him between them, to keep him from escaping. He noticed I was wearing a bra and took off the top part of the dress.

—It’s a very pretty set —he said—. I love seeing you wearing this.

I was hypnotized, surrendered. He started touching my chest and all I could think to say was:

—I wish I had breasts, then you’d enjoy my body more.

—Don’t worry —he replied—. Someday you’re going to fill these bras and you’re going to be one of the sexiest women there is.

Just hearing that made me rock hard. He noticed it instantly, and I felt embarrassed.

—Sorry. It’s just that it really turns me on when you say things like that.

—That’s normal, baby. If you want, another day we can do something with that too. You’d look delicious totally flat down there.

I had never imagined what I would look like with nothing between my legs, and I liked the idea. Darío started playing with my nipples and I moaned like a girl, surprised by how natural it came out.

—Do you like the idea? —he asked.

—Yes, it sounds good.

He kept touching me while promising to make me come like the last time. With all the shame in the world, I asked him not to kiss me up front, but to kiss me from behind like he had before. He understood at once. He lifted the rest of the dress, pulled down my underwear, and I was exposed to him again.

I felt like I was in heaven. He started sliding his fingers in while keeping touching me, and I just kept moaning and covering my face, dying of embarrassment at how much I was enjoying it. At another time I would have asked him to keep doing that for hours, but that night I was desperate to feel him inside me.

—Just do it, Darío.

—Do what?

—Make love to me.

—You want me to make you mine that badly?

—I want to be only yours already. I can’t take it anymore.

He stripped completely and put on the condom. I pointed to the baby oil bottle and watched as he spread it along the length of his cock. He positioned me and I felt the tip teasing my entrance. All I could feel was him trying to work his way in. There was a moment when I wanted to pull away, pure reflex, and he held my arms firmly so I wouldn’t move. I endured as much as I could.

—Take it out —I asked.

—No, hold on a little longer.

After a few minutes the pain disappeared. Darío started moving slowly, going in and out.

—Are you okay? —he asked.

—Yes, keep going.

All I could think was that, after so much waiting, he was finally making me his woman. Knowing we were doing it in my bed, in my parents’ house, turned me on even more. I started clenching around him and he noticed. He thrust harder and faster. I touched myself too, on the edge of orgasm, when he asked me:

—Do you like it, Camila?

—Yes.

—Do you like how I make you my woman?

—Yes, I love being your woman.

After several sharp moans, I came. I soaked the bed, the new dress, and him. Right away I felt Darío climax too; I’d never heard him moan so loudly. He was spent and, still inside me, lay down on my chest. I held him with my legs while stroking his back, thinking that from that moment on my life would no longer be the same. My desire to be treated like a woman would only grow.

I felt him pull out of my body. He looked at me and asked if I had liked it. I gave him a long kiss.

—I loved it —I told him.