He was such a cute girl (Part 1) [MM]

So this happened a few years ago when I was 24, during summer holidays in my country, Italy. I used to spend most of the summer, every summer, at the seaside where my family owns a house – boy I miss those long summer holidays as a college student!

Anyway I had a big crush on this girl Laura, a 20 years old stunner that unsurprisingly worked as a model locally. A tall, athletic brunette with hazel eyes, an angel face and terrific body, she was the wet dream of every male of any age. We went to the same beach and were pretty close as we were part of the same group of friends. I was also somewhat close with her dad Carlo, as we used to play soccer and tennis together during the summer – I also hoped to get closer to Laura this way. With some success actually, as Carlo and Laura invited me to the 18th birthday party of Laura’s little brother Christian. Christian was a bit of a shy kid, he was very polite and well educated though not particularly popular, unlike Laura. He did look a bit like his sister, especially the face, but was a bit short (probably around 1,65 m) and skinny, and generally seemed to lack Laura’s confidence and charisma, almost like he preferred to live in his sister’s shadow.

The party was ready to start as Carlo had rented the beach including bar and restaurant, so everything was good to go, the guests, the drinks, the music, the DJ. As usual I was trying to impress Laura, with limited success. Carlo took the mic and finally introduced the arrival of the birthday boy… except instead of Christian a cute girl in a sexy dress came in to everyone’s surprise. ‘Classic Carlo ‘ I thought as other guests laughed and joked with him. But wait a minute… as I looked more carefully the cute girl in the sexy dress… was actually Christian! For some reason he decided to dress up as a girl – including a wig and make up – for his 18th birthday party and Carlo played along. There was a brief moment of general embarrassment, mostly because Christian looked like a real girl, and a very pretty one too, but soon the crowd was happy to embrace the joke and started clapping, screaming, dancing and the party could begin. At some point I was drinking a glass of wine with Carlo, Laura and Christian among others and Carlo, always the joker, asked me ‘My son is a hottie, isn’t he?’. Following his lead, I pretended to watch carefully both Laura and Christian and said that Christian was way hotter. Carlo laughed hard, while Laura shook her head and Christian had the biggest smile. To be honest I had never seen Christian having such a great time before that day, he was just having a lot of fun and for the first time seemed to enjoy being the center of attention. This was about the end of july.

On the night of august 10th – the night when you’re supposed to see falling stars – our group of friends had a party on the beach, as we did every summer. We would buy all kinds of alcohol – beer, wine, vodka, tequila, gin, rum – and just spend the night drinking on the beach. Of course this was mostly an attempt to get lucky with the girls. And of course Laura was my top target. Who knows maybe the stars, the alcohol… So there were a ton of people that night. Laura also brought her brother Christian (dressed as a boy of course!) though he wasn’t particularly comfortable around our older group – there were a few girls of his age, though most people was around 24-25. Which meant Christian spent most of the time around his sister – and incidentally around me. Laura didn’t drink much, I did though which made my attempts to woo her even more moronic than usual. At some point I managed to tell her that if she kept playing hard to get I might as well put a wig on his brother and fuck him instead. Of course it was supposed to be a joke. Christian was amused. Laura not so much as she went away and spent the rest of the party with her girlfriends. After that Christian mostly hanged out with me as I introduced him to the other guys and basically kept drinking till I got shitfaced. Because Christian was vaguely popular only for his birthday extravaganza, in a very drunk attempt to get him blend with the guys I started yelling things like ‘Christian is the hottest girl of this party’ or ‘Get Christian a wig’ and even ‘I have fucked much uglier girls than Christian’ and ‘Dress him up like his birthday and I’ll fuck him right now’. Pretty heavy stuff but the guys , mostly drunk like me, laughed hard and Christian was also surprisingly amused and happy to play along. After a few hours I didn’t feel like spending the whole night on the beach like most of the group usually did (especially as it was clear that I blew my chance with Laura), so said goodbye to the gang and headed to my scooter, must have been past 2 AM. The guys yelled some final drunk nonsense at me like ‘If you don’t fuck Christian you’re a pussy!’ so I replied directly to him and told him he can come at my home anytime and I’d fuck him but only if he dressed like a girl. Big laughs once again. Finally I managed to start my scooter after a few tries, and left the party completely drunk.

I somehow made my way home, luckily not so far from the beach. I drank a coke which for some reason always helps me overcoming a hangover, then I collapsed on the sofa and fell asleep. I woke up to the sound of the intercom, wtf it was almost 4 AM. I went answering half-drunk, half-asleep. ‘Hey it’s me Christian’. ‘Wait who? Alright come in’. Not even sure I got that right, I opened the gate then the door. It was Christian indeed. And he was dressed like a girl! Now I was half-drunk, half-asleep and fully shocked. I let him in quickly and didn’t really know what to say. Now we’re both standing in the living room in front of each other. He’s wearing a pair of sneakers, some ripped denim shorts and a sleeveless white top. He’s also wearing the same long, dirty blonde wig he had on his birthday, plus some lipstick and light make-up. To be honest he – or should I say she? – looks absolutely cute. Suddenly Christian breaks the silence as he smilingly asks me a very simple question: ‘So… would you fuck me?’.

Source: reddit.com/r/gonewildstories/comments/d3ucpd/he_was_such_a_cute_girl_part_1_mm