My first time dressing up as a girl
Everything started just a few years ago. My 2 best friends during school were girls, i always felt more comfortable hanging out with them instead of boys. We had a really great and open friendship, we were a bit on that crazy side, always playing dares and pushing each other to do silly stuff.
So one day we were hanging at one of their houses preparing for a Halloween party later that night. I never cared much about it, halloween isnt a big deal around here so I didn’t have a costume or anything. My friends on the other hand loved dressing up, they were into cosplay and such, it was really fun for them. So they were giving me a hard time for not joining them.
We were drinking a few beers and fooling around as the night fell, and one of my friends jokingly say that i could borrow one of their outfits for the party, the other one joined and they started to ponder the idea of dressing me up, teasing about how much of a good fit it would be for my small feminine body type and what not. Well, a bit of alcohol here and there, we kept joking about it and before I knew it they were ushering me into the bathroom with a maid dress (like the ones you see on anime or maid cafes in japan), wig, stockings and all. To be honest i didnt mind, I thought it would look plain silly and i would get a lot of laughs at the party so i went for it.
I didn't know what i was getting into. Once i was done changing i was shocked at how well it fitted me. I always wore big baggy clothes since i am a bit on the petite side and even normal sized boy stuff looked oversize on me. But this was completely different, it felt like it was designed for my body.
Of course my firends were super happy with it, and before i could protest they were all over me doing some makeup. I looked at the mirror when they were done and i was stunned at how good i looked, this was not what i was expecting at all and looking back at that cute girl in the mirror i started to get a warm feeling inside. I asked my friends for a moment alone to collect myself. It was sensory overload, i could feel the dress marking the curves of my body, the stockings pressing tight against my legs, even the playful choker around my neck, and everything felt so nice, it felt.... right. I was posing on the mirror, trying to find ways to look more feminine.. more sexy. The skirt of the dress was on the shorter side, if i bended over a little part of my butt would get exposed. Then i caught myself. What was i doing?! I started to get nervous, this was supossed to be a fun dumb joke, but i knew it wasnt anymore, at least not for me. I almost stopped there, even tho my friends reassured me i would pass just fine and there was nothing to worry about, i almost stopped, but i didn't. I couldn't, i really liked this.
So with some more encouragement from my buddies and maybe with some help of more alcohol, i made it to the party with the nerves under control.
At the party i noticed some guys eyeing me up and down and more than one came to flirt before me and my friends would reveal to them i was a boy and laugh it out. It was so much fun.
As the night went on i got a lot more comfortable and confident. I let my friends go do their own thing and went to explore by myself. I could feel the gaze of some guys as i walked past them, were their eyes drifitng to my legs and butt or was it just my hopeful imagination? I found the feeling so thrilling, i couldnt get enough of it, i would put my best effort into moving as feminine and graceful as possible and not long after i reaped my frist reward. As i was walking between the crowd at the dance floor i felt a slap on my butt. I instinctively turned around but between the light show and the amount of people it was impossible to knew who done it. I felt my heart pumping, my adrenaline was trhough the roof, i knew i should feel embarassed or annoyed, but if anything i just felt excited, i wanted more. I wasnt a good dancer but i tried my best to shake my hips and perk my butt to the music in a seductive way. A few songs went on i was about to give up when suddenly a hand firmly grabs one of my butt cheeks. It was so sudden and way more direct than the previous tentative slap that i just froze. I think he took this as approval as he put his hands on my waist and started dancing behind me.
I could feel my face burning red, i didnt know what to do so i let his hands guide my hips wtih the music. My mind was a complete mess, so my body took over almost moving on its own. It was one of those spicy reggaeton beats, so before long i could feel him pressing close, his big hands in full control of my body. And i loved every second of it, submitting myself to this complete stranger felt right. When the song came to an end he slid his hand under my skirt and gave me another squeeze. His fingers digging hard through my stockings, he caught me off guard once more. And just like that he took off. I was still on a bit of a daze. So many things running through my mind. When i got a hold of myself and i looked back he was gone. I was then aware of the bulge in my undies, but thankfully the frilly nature of the skirt didnt make it noticeable.
I went outside to get some air, my breathing fast and heavy, my face warm and legs shaking as i sat there on the grass processing everything that just happened.
The night that started as a simple joke now sparked so many new feelings and desires within me. I felt so vulnerable but accomplished at the same time. Its hard to describe.
So from that point on i would look forward to any opportunity to dress up. Events, costume parties, were the highlight of my year. And in between those i could always sneak into my sis room to play when she wasnt around.
So one day we were hanging at one of their houses preparing for a Halloween party later that night. I never cared much about it, halloween isnt a big deal around here so I didn’t have a costume or anything. My friends on the other hand loved dressing up, they were into cosplay and such, it was really fun for them. So they were giving me a hard time for not joining them.
We were drinking a few beers and fooling around as the night fell, and one of my friends jokingly say that i could borrow one of their outfits for the party, the other one joined and they started to ponder the idea of dressing me up, teasing about how much of a good fit it would be for my small feminine body type and what not. Well, a bit of alcohol here and there, we kept joking about it and before I knew it they were ushering me into the bathroom with a maid dress (like the ones you see on anime or maid cafes in japan), wig, stockings and all. To be honest i didnt mind, I thought it would look plain silly and i would get a lot of laughs at the party so i went for it.
I didn't know what i was getting into. Once i was done changing i was shocked at how well it fitted me. I always wore big baggy clothes since i am a bit on the petite side and even normal sized boy stuff looked oversize on me. But this was completely different, it felt like it was designed for my body.
Of course my firends were super happy with it, and before i could protest they were all over me doing some makeup. I looked at the mirror when they were done and i was stunned at how good i looked, this was not what i was expecting at all and looking back at that cute girl in the mirror i started to get a warm feeling inside. I asked my friends for a moment alone to collect myself. It was sensory overload, i could feel the dress marking the curves of my body, the stockings pressing tight against my legs, even the playful choker around my neck, and everything felt so nice, it felt.... right. I was posing on the mirror, trying to find ways to look more feminine.. more sexy. The skirt of the dress was on the shorter side, if i bended over a little part of my butt would get exposed. Then i caught myself. What was i doing?! I started to get nervous, this was supossed to be a fun dumb joke, but i knew it wasnt anymore, at least not for me. I almost stopped there, even tho my friends reassured me i would pass just fine and there was nothing to worry about, i almost stopped, but i didn't. I couldn't, i really liked this.
So with some more encouragement from my buddies and maybe with some help of more alcohol, i made it to the party with the nerves under control.
At the party i noticed some guys eyeing me up and down and more than one came to flirt before me and my friends would reveal to them i was a boy and laugh it out. It was so much fun.
As the night went on i got a lot more comfortable and confident. I let my friends go do their own thing and went to explore by myself. I could feel the gaze of some guys as i walked past them, were their eyes drifitng to my legs and butt or was it just my hopeful imagination? I found the feeling so thrilling, i couldnt get enough of it, i would put my best effort into moving as feminine and graceful as possible and not long after i reaped my frist reward. As i was walking between the crowd at the dance floor i felt a slap on my butt. I instinctively turned around but between the light show and the amount of people it was impossible to knew who done it. I felt my heart pumping, my adrenaline was trhough the roof, i knew i should feel embarassed or annoyed, but if anything i just felt excited, i wanted more. I wasnt a good dancer but i tried my best to shake my hips and perk my butt to the music in a seductive way. A few songs went on i was about to give up when suddenly a hand firmly grabs one of my butt cheeks. It was so sudden and way more direct than the previous tentative slap that i just froze. I think he took this as approval as he put his hands on my waist and started dancing behind me.
I could feel my face burning red, i didnt know what to do so i let his hands guide my hips wtih the music. My mind was a complete mess, so my body took over almost moving on its own. It was one of those spicy reggaeton beats, so before long i could feel him pressing close, his big hands in full control of my body. And i loved every second of it, submitting myself to this complete stranger felt right. When the song came to an end he slid his hand under my skirt and gave me another squeeze. His fingers digging hard through my stockings, he caught me off guard once more. And just like that he took off. I was still on a bit of a daze. So many things running through my mind. When i got a hold of myself and i looked back he was gone. I was then aware of the bulge in my undies, but thankfully the frilly nature of the skirt didnt make it noticeable.
I went outside to get some air, my breathing fast and heavy, my face warm and legs shaking as i sat there on the grass processing everything that just happened.
The night that started as a simple joke now sparked so many new feelings and desires within me. I felt so vulnerable but accomplished at the same time. Its hard to describe.
So from that point on i would look forward to any opportunity to dress up. Events, costume parties, were the highlight of my year. And in between those i could always sneak into my sis room to play when she wasnt around.
11 months ago
