Growing up i always had a bit of a queer/feminine side, even though i didnt realize it at the time. My two best friends during school were girls, i felt more comfortable with them they were really open and fun, we would play dares, pushing each other to do dumb stuff and what not.
 
So it was during halloween when it all started, we were hanging out at my friends house preparing for a costume party that was taking place that night. I didnt really care too much about parties and all that back then, so i wasnt planning on wearing a costume, my friends on the other hand were super into it, they really liked to cosplay and going to events so it was a big thing for them, i was just there to accompany them.
We were drinking and fooling around, as teens do, and at some point one of them jokingly suggested i should wear one of their costumes since i didnt have one, we laughed and kept joking about it, a few more drinks in between, jokes became a dare and before i knew it they were already deciding what type of dress i should wear. A few moments later they were ushering me inside the bathroom with a sexy maid outfit, stockings, cat ears and everything in my hands.
I didnt mind really, in fact i thought it would be a really fun thing to pull at the party, i mean a guy dressed up in some cutsey girl outfit would certainly look plain silly and i would get a lot of laughs, so i went for it.
But when i was finally done dressing up i realized how wrong i was, the outfit didnt look silly, in fact i was amazed at how well it fitted. I always wore big baggy clothes since i was really petite and even normal size boy clothes would look oversized on me. But this... this felt like it was made for my body.
My friends were super happy with it too, and before i could even say anything they were all over me doing some makeup. I looked at the mirror when they were done and i was stunned, a cute girl was looking right back at me, i was starting to get a weird warm feeling inside of me, then i caught myself and i started to protest, asking them why they had to go so hard on the makeup and what not, it was supossed to be a fun silly joke after all.. not turning me into an actual girl! They laughed and told me they barely did any makeup, it was my small and soft features that were just too girly to begin with, i started blushing and suddenly pushed them out of the bathroom, locking the door telling them i had to pee.
In reality i just realized a big bulge was starting to form in my undies, luckily the frilly skirt of the dress was concealing it. I took another look at the mirror, i still couldnt believe how pretty i looked, i was suddenly aware of my girly shape, my tiny waist and my thin legs. I could feel the fabric of the stockings pressing tight against my skin and the bulge was now a raging boner i had to take care of. It didnt take long, I never before gotten this aroused after all.
A sudden knock on the door took me out of my thoughts, my friends were telling me to hurry up, it was time to go. Without that little distraction under my skirt, plus the support of my friends and maybe a few more sips of alcohol the nerves started to fade away.
We made it to the party and everything went smoothly, the more I moved around in this outfit the more comfortable I felt in it, I loved how it highlighted the shape of my body and I don’t think I was the only one, since I noticed several boys eyeing me up. I even got my butt groped a couple of times when I had to go through the crowd to get a drink or go to the toilet. And even though it was embarrassing I had to admit i really liked it.
My friends were teaching me how to walk and dance in a more feminine way, and they even got a random guy to practice with me. Feeling his hands on my waist, pressing his body close against me as I was trying to awkwardly shake my hips for him was almost too much, I could feel my face burning red and that same warmth starting to rise between my legs.
Nothing much else happened but it was a night I would never forget. 
This sparked so many new feelings inside of me. I never felt so happy and accomplished.
So what started as a joke ended up being a life changing experience for me.