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. There wasn’t a day I didn’t touch myself imagining it was him doing it, his large, unhurried hands running over my lower back, sliding down to squeeze my ass and part my cheeks while he pressed a wet finger against my hole. I would slide two fingers into my ass thinking about his cock, moaning softly into the pillow so no one would hear, and I’d come in my hand imagining it was him emptying himself inside me.

The days kept passing and Darío didn’t contact me. I called him a couple of times, but he always sent me straight to voicemail. I felt neglected, ignored, and still desperate for 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 tingle between my legs, ashamed and turned on at the same time by the thrill of knowing no one suspected what I was hiding. The fabric rode between my cheeks, and every time I shifted in my seat the lace rubbed my hole, leaving me half-hard inside my pants all morning.

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, the ones who knew how to grab a novice little slut and do everything to her without asking twice.

I started saving money. I planned to go to a market in a nearby city and buy myself real clothes, something more sensual, more daring, something that would let me explore the woman inside me fully. After Darío ignored me all week, the following Saturday I fantasized about putting on women’s clothes under my men’s clothes and going out to find someone on my own. The idea excited me: finding a mature man willing to do anything to me, to fuck my mouth until I choked, to break me in one go and come inside without pulling out.

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

—This week we’re seeing each other for sure —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. Even so, I took advantage of the chance to put on some feminine clothes under my normal 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 I could borrow her laptop, since she was heading out, and she agreed. It was the perfect day to browse the internet. Before social media took off, there were chat rooms, where you could talk to hundreds of strangers at once. I chose the nickname CamilaTv and entered a room devoted to girls like me and the men who looked for them.

I just wanted a little filth. I wrote in the main room that I was looking to chat and said what city I was in. I got several private messages, 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 my same city. 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, baby, and things you can’t even imagine. You’re going to be delighted with me —he wrote.

—Really? And what exactly are you going to do to me? —I answered.

—First I’ll get you on all fours, eat that little ass of yours, make it really wet with my tongue, put my fingers in you until you open up, and then I’ll shove my whole cock in and empty myself inside. I’ll fuck you until milk comes out of your mouth.

The way he talked to me was rough. Darío was much gentler, but since it was over the internet I assumed it would all stay fantasy, so I let myself go. I admit that kind of talk turned me on. I already had a hard-on pressed against my pants just from reading it.

—But I’m a virgin —I wrote—. It’s going to hurt.

—Don’t worry, I’ll make it feel really good. It’ll sting at first, but once I get into the rhythm you’ll be begging me for more cock. You’ll end up pleading for me to ram it all the way in.

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

—At your house, baby. Right there, in your bed, with your parents sleeping next door, I’ll make you a woman. I’ll cover your mouth so you don’t scream when I bury it in you.

I didn’t want to admit it then, but the idea of him coming to my house to make me into a woman lit me up. A moan slipped out and I squeezed my legs together. That made me bolder in the conversation.

—Tempting —I wrote—. Right now I’m in my room, dressed like a girl, with a pink thong riding up my ass. But my parents are here. I don’t think it can happen.

—Pull down your thong and stick a finger in yourself thinking about my cock, slut. When they’re asleep, let me know. I’ll come, fuck you, fill your ass with cum, and leave. No one will know. And if they do, let them see they’ve got a very pretty and very daring daughter, a very slutty one.

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

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

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

—You’ll regret not feeling my twenty-five centimeters in that little ass of yours. I’ll put it in slowly, all the way, until you feel my balls slapping against your ass. I’ll turn you into a real little woman.

I don’t know whether the size was true, but what I do know is that it left me dripping just imagining the situation. I closed the chat, shut the laptop, and lay down on the bed. With a little baby oil I started touching myself, smearing my ass and balls really well. I licked two fingers and slid them in slowly, feeling the hole give way. I started pumping them hard, imagining ElDomador80 coming into my house, putting me on all fours, and burying his cock in me without giving a damn that my parents were on the other side of the hall. I covered my mouth with the pillow and grabbed my cock with my other hand, jerking myself fast while I kept fingering my ass. I came on my stomach in less than a minute, shaking all over, and stayed there with my fingers still inside, leaking cum and breathing hard.

***

At college, final exams for the semester were approaching. Classes were reduced to taking the test and going home. I used to leave with friends to play pool, but that time I decided to go straight back so I could 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 avoid drawing attention and tried to cover my face. The market was huge. I carefully checked the stalls, not just looking for pretty clothes but for one run by an older woman I wouldn’t be embarrassed to buy from.

I found one full of lovely pieces, run by a woman in her mid-forties. She said the clothes had been brought from abroad, perfect for giving to a girlfriend. I wanted to buy quickly: I chose a short black dress embroidered with yellow flowers, a pink silk nightgown with black details, and a set of pink lace underwear that looked beautiful. Everything cost almost all the money 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 have more pretty things at good prices.

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 village on the outskirts of the city, and wouldn’t be back until Sunday night. I was thrilled. When they said my sisters were going too, I almost jumped for joy. They asked if I wanted to come along, and I used my exams as an excuse: I said I was exhausted and still had papers to finish. They accepted without a problem.

All afternoon I called Darío, but he kept sending me to voicemail. I didn’t really care: 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 they all left. As soon as I closed the door, I went to take a bath. I made myself immaculate and used my sister’s scented soaps to feel more feminine. I soaped my ass carefully, slid two fingers in with foam so I’d be really clean inside, knowing that night something much bigger was going in. I knew it was a decisive night, so I kept trying his number. After several attempts, 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? No one’s here. I want you to see me in the sexy clothes I bought.

He was incredulous for a few seconds, 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 already outside. I opened the garage so he could pull in the truck and asked him to wait for me 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 small bow as decoration.

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

***

The moment 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 sliding up my thighs made the urge to take him to bed grow nonstop. He shoved his tongue down my throat while squeezing my ass with both hands, parting it over my thong, and I sucked his tongue like it was a little preview of what I wanted to do to him downstairs.

—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 answered, ignoring him.

—You’re gorgeous, Camila.

—Then I don’t care if they come back. Let them know they’ve got another daughter.

I lowered my hand to his crotch. I felt him hard, his cock outlined against his pants like a rod. I squeezed it over the fabric and he let out a low grunt. I tried to undo 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 just smiled. I opened his pants, pulled down his boxers, and took out his cock. It was thick, with a vein running underneath and the tip already wet with pre-cum. I licked my lips and bent over the sofa; it had been a long time since I’d had it in my mouth. I held him at the base with my hand, stuck out my tongue, and licked from his balls to the tip in one slow stroke, tasting the salty flavor. Then I took all of it into my mouth, pushing it down my throat until my eyes filled with tears. I started sucking him hard, bobbing my head up and down, helping myself with my hand, while I ran my tongue over the frenulum every time I pulled back. With my other hand I stroked his balls, squeezing them gently. I could tell it was harder than other times, swollen, and he gripped my wig to set the pace. Darío was enjoying it like never before, moaning softly, leaning back into the sofa.

—That’s it, baby, suck it like that —he panted—. You have no idea how much I missed that little mouth.

I spit on the tip and rubbed it with my hand while sucking each ball one by one, taking them into my mouth. Then I took him all the way down again, gagging on purpose so he’d feel my throat closing around the tip. I paused and stood up so he could look at me again, my lips shining and a trail of saliva hanging from my chin down to his cock, which was pointing at the ceiling.

—Where did you get that dress, babe? —he asked, breathing hard.

—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 locked on my ass. He stood up, got behind me, squeezed my cheeks, and gave me a slap that made me moan. Then he pulled my thong aside with a finger and ran his thumb over the hole, barely pressing, and I pushed my tail back to open myself for him. In his eyes I could read that tonight he was going to make me his, that he was going to break me. I sat back on his lap, this time astride him, his cock rubbing against me beneath my thong, and while I ground myself against it I kept kissing him.

—Did you bring a condom? —I asked.

—Yes, I brought several.

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

He didn’t say anything. He just smiled, got up, went to the truck for the condoms, and came back with a small digital camera. I took him by the hand and led him toward the stairs, but first we stopped in front of the hallway mirror.

—Take a picture of me —I asked—. As a keepsake of the day I become a woman.

He hugged me from behind and snapped the photo. Then we went upstairs. My room was the room of any ordinary 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 catch him between them, not letting him escape. He noticed I was wearing a bra and took off the top part of the dress.

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

I was hypnotized, surrendered. He started touching my chest, pinching my nipples through the lace until they were hard, and all I could think to say was:

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

—Don’t worry —he answered, while sucking one nipple and tugging the other with two fingers—. Someday you’ll fill these bras and you’ll be one of the most sensual women there is.

Just hearing that made my cock rock hard. I had it pressed against the thong lace, leaking from the tip, leaving a little wet spot on the fabric. He noticed right away, slipped his hand underneath, and grabbed it over my underwear, squeezing. I felt ashamed and aroused at the same time.

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

—That’s normal, baby. Look how hard you’ve got it, sweetheart. If you want, another day we can do something with that too. You’d look delicious completely flat down there, with nothing in the way.

I had never imagined how I’d look with nothing between my legs, and I liked the idea. Darío pulled my thong down to my knees, took my cock out, and started playing with it with the tips of his fingers, stroking me slowly while his other hand played with my nipples. He bent down and ran his tongue over the tip, licking my pre-cum like it was cream, and I moaned like a girl, surprised at how naturally it came out. He took me all the way into his mouth, to the back, and sucked me for several seconds, squeezing my balls with his hand. I shivered. He stood back up, licking his lips.

—Do you like the idea? —he asked.

—Yes, it sounds good.

He started touching me while promising to make me come like he had the last time. With all the shame in the world, I asked him not to kiss me up front again, but to kiss me from behind like he had before. He understood right away. He lifted what was left of the dress, finished pulling down my underwear, and turned me face down, slipping a pillow under my hips so my ass would lift up, and I was exposed to him again, my cheeks parted and my hole on display.

—What a delicious little ass you have —he murmured.

I felt like I was in heaven. I felt his hands parting my cheeks and then his hot, flat tongue sliding from my balls to my hole in one slow lick. I shuddered all over and moaned into the pillow. He ran it over me once, twice, three times, each time slower, sucking around the little hole, getting me really wet. Then he pressed the tip of his tongue right there, pushing, and I felt it open a little to let him in. He put it in, pulled it out, pushed it in again, while with one hand he kept stroking my cock underneath. I gripped the sheets and bit the pillow so I wouldn’t scream. When I was thoroughly wet and stretched, he started slipping in one finger slowly, all the way, and then the second. He worked them like scissors, opening me up, while still touching me, and I could only let out muffled moans and cover my face, mortified by how much I was enjoying it. I felt pleasure rising in waves every time he bent his fingers and hit something inside me that made me see stars. Any other time I would have asked him to keep going like that for hours, but that night I was desperate to feel it inside.

—Do it already, Darío.

—Do what?

—Put it in me. Make love to me.

—Do you want me that badly to make you mine?

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

He stripped completely and put on the condom. I pointed at the baby oil bottle and watched as he spread it along his shaft, slicking it with his hand, then smeared a good amount on my ass, slipping two oily fingers inside so it would slide. He positioned me on my side with one leg up, and I felt the tip flirting with my opening, pressing, resting there. All I could feel was how it tried to force its way in, how the ring burned as it gave way. He pushed slowly and I felt the head enter all at once, and I let out a muffled cry. There was a moment when I wanted to pull away, pure reflex, and he held my arms firmly so I wouldn’t move, leaning his whole weight over me. I held out as long as I could, grinding my teeth.

—Take it out —I asked, with tears in my eyes.

—No, hang on a little longer. Breathe, baby, I’m almost all the way in.

He kept pushing little by little, one centimeter at a time, until I felt his balls hitting my cheeks. He was all the way inside. He stayed still for a while, giving me time, kissing my neck and whispering in my ear how tight I was, what a delicious ass I had, how I was already his. After a few minutes the pain disappeared and all that remained was the feeling of being full, of being wide open. Darío began moving slowly, in and out, with long thrusts that made me feel every inch.

—Are you okay? —he asked.

—Yes, keep going, harder.

I could only think 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. He flipped me completely face down, lifted my hips, and got on top of me, and from that position he started fucking me harder, pushing me down with every thrust. The mattress creaked, the bed banged against the wall, and I moaned into the pillow like a bitch. I started clenching around him and he noticed. He thrust faster and harder, gripping my hips with both hands, digging his fingers in. Then he told me to get on all fours. I obeyed immediately. I knelt, my face against the mattress and my ass raised, and he went in again, all the way, in one shot. He grabbed my wig, pulling it so I’d lift my face, and he fucked me mercilessly, slapping my ass until one cheek burned red. I was stroking my cock at the same time, jerking it fast beneath me, right on the edge of orgasm, when he asked:

—Do you like it, Camila? Do you like the way I fuck you?

—Yes, I love it.

—Do you like the way I make you my woman? Say it, tell me you’re my slut.

—Yes, I’m your slut, I’m your woman, fuck me with all that cock.

After several high-pitched moans, I came. I felt the load rising from my balls and leaking between my fingers, staining the sheet, the new dress, everything. As I came, my ass clenched all the way around his cock, and right away I felt Darío finish too; he dug his nails into my hips, buried himself to the hilt, and stayed there, trembling, while he emptied the condom inside me with a long, deep groan I had never heard from him before. I felt the cock throbbing inside me, pulsing, cumming. He was spent, and still inside me, he collapsed onto my back. I stayed face down, feeling his weight on top of me, his cock slowly shrinking in my ass, while I stroked his hands, thinking that from that moment on my life would never be the same. My desire to be treated like a woman was only going to grow.

I felt him slip out of my body with a wet little sound, and my hole was left open and throbbing, feeling suddenly empty. He took off the condom, tied in a knot and full to the top with semen, and showed it to me. He looked at me and asked if I liked it. I gave him a long kiss.

—I loved it —I told him.