It turned out that way

Since early youth, I've been fascinated by dressing in women's clothing. I don't do it often, but sometimes the desire arises. I transform myself, put on makeup, and twirl in front of the mirror, admiring myself, as my figure is decent enough. Women's clothes look quite good on me. I have a slender build, legs that are also slender and long, narrow shoulders, and my own dark, curly hair that falls below my shoulders. I used to be into push-ups, which left me with a chest around a size 1.5. Otherwise, in everyday life, I'm just a regular guy. I've never had any relations with men, although I'll be honest, such thoughts have crossed my mind more than once.

Once, my older brother came to visit for a couple of days. He's a couple of years older than me. We rarely see each other since we live in different cities. He had some business in our city, finished it in a day, and decided to stay for the weekend to look around. My family was away, so there were no issues with accommodation.

We hadn't seen each other for a long time. For his arrival, I bought some drinks and snacks. He came in the evening, we sat down at the kitchen table, started chatting about this and that, about life, about girls and what to do with them, and drinking in the process. I don't drink hard liquor, so I stuck to champagne, while my brother drank cognac. Along the way, out of boredom, we started playing cards. After a while, it got dark outside, and we were already quite drunk.

Gradually, we started playing for dares—like drinking in one gulp, calling someone we know and pranking them, and so on. I lost again.

And then my brother made a wish:

"It's kind of boring without girls, no one to flirt with. But you seem to have a figure. Why don't you dress up as a girl? At least there'll be some semblance of a girl's presence."

I started to refuse, but my brother began to persuade me. I imagined myself in a feminine guise in front of a man, and the thought started to excite me. In the end, I gave in and went to the wardrobe to pick out clothes.

I picked out some clothes, lingerie, took high-heeled sandals, makeup, and went to the bathroom to shower and get into character. The thought crossed my mind—what if casual flirting turns into something more? I washed myself thoroughly everywhere, shaved, and began my transformation.

I came out to my brother looking like that. Seeing me, he whistled in surprise and visibly perked up. He said he didn't expect me to make such a pretty girl and asked me to twirl in front of him so he could get a better look. First, I slowly turned my back to him, then, leaning forward a bit, I arched my back and stuck out my butt. I had never heard so many compliments about my butt and legs before. After that, I sat on my chair, turned halfway towards him, and crossed my legs. My dress slid up a bit, revealing the edge of my stockings. My brother sat opposite on the sofa, devouring me with his eyes, looking me up and down. It was noticeable that he wasn't indifferent to my appearance. There was a certain spark in his eyes.

"Do you mind if I call you Olya?" my brother asked.

I didn't mind. He poured me some champagne and suggested a toast to our acquaintance. We drank. My brother put on some slow music and invited me to dance.

No, I told myself. This needs to stop before something irreversible happens. I pulled myself together and pushed away from my brother.

"We need to have a smoke and come to our senses," I said, "because we're getting a bit carried away."

We went into the kitchen. He sat on a chair, and I sat on top of him, facing him. I took his cock and guided it into my ass. It went in "like butter," and I started moving slowly on him. I liked it so much that I didn't want him to finish quickly. My brother caressed my butt and breasts. Then he lifted me up without pulling his cock out of me, laid me on the table, spread my legs apart, and started fucking me again. I completely relaxed and felt his cock going in all the way and his balls slapping against my butt. It didn't last long, and my brother came inside me with a powerful stream.

A few minutes later, we were standing on the balcony smoking. My brother hugged me from behind and said he'd never had sex like that before, that he really enjoyed it, and he wouldn't mind if I stayed as Olya until he left. I had no desire to refuse him because I'd never had sex like that either and really wanted to try a lot of things.