This is 100% real and true story as best as I can remember how everything happened. This is my first time writing a story, so please bear with me.

First, about me, I was in my teens at the time, green eyes medium length brown hair, about 5’5 110lbs skinny and fit. Typical horny teenager with access to the internet. I got to see a lot of things and open my interests and curiosities. While scrolling through porn sites I had come across some trans and crossdressing porn that really piqued my interest and turned me on. I didn’t consider myself as gay but I was fascinated by these feminine guys wearing sexy underwear and fishnets and wigs/makeup. It was like the taboo of it made it extra hot to watch. I liked their smooth skin and the way the stockings or fishnets made them look just like a girl. I liked how feminine their ass and legs looked in frilly panties.

Watching these gurls pleasuring a man looking and doing exactly what she's supposed to do but then you see their little cock straining and flopping around just felt so taboo and so naughty. Over the years I’ve learned that’s what I like. I like to please, whether I’m with a girl or guy, I feed off their reaction and how into it and how horny I’m making them. Which is why I like to watch these gurls get that reaction out of a guy. Getting them to lust over them because of their enthusiasm and girlish mannerisms.

This lead to me wanting to try on girly things myself. Luckily I have an older sister only about three years older than me and was taller than me at the time but about the same waist size as me. I ended up sneaking into her room when everyone wasn’t home to go through her underwear. I would purposefully try not to disturb her dresser or anything in her room too much as to not raise suspicion that someone had gone through or touched anything. I would also purposefully try to pick from stuff that was buried deep in the drawer because it was less likely to be a favorite piece of clothes that she wore often. I’d pick some panties and a bra and quickly try them on and check myself in her mirror, sticking my butt out admiring how girly my ass looked. Once I found a pair I liked I'd make sure everything was back in its place before leaving to my room. I’d hide the items deep in my closet and wait till late at night when everyone was asleep.

I would also do the same thing with my mom's dresser drawers and closet but she didn’t really have much of the smaller frillier things that piqued my interest. And a lot of her stuff was too big on me.

Once everyone was asleep I would go grab my dad’s laptop and take it to my room. I'd get the panties and bra out from earlier and slip them on and lay in bed scrolling through porn fantasizing about being the girl or gurl on the screen. I'd spend hours doing this and would cum multiple times until I was exhausted and it was late. Then I'd clean up and make sure I cleared all the history and cookies from the laptop before putting everything away again making sure nothing looked disturbed from where I originally got it.

Over the weeks I kept doing this I found some miscellaneous hair care and mini shampoo bottles that were about the size of a penis that I ended up using as makeshift dildos after figuring out how hard it was to insert them in I ended up riding my bike down to the local Walmart to pick up a bottle of lube.

Sorry, this part is very short, but I wanted to give kinda a background on my curiosities and how they formed before going into the next part of my story where I'll talk about me and my friend James and how he got me to explore my sexuality more with him. Though I did not wear anything girly for him for quite a while, just as an FYI when you read my next story there wont be much dressing until later parts. I didn’t know just how curious he was at first, so I played it cautiously.