my story of becoming a crossdresser
Here are some stories about my sex life and exploration of who I am.
Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags.
One night when I was reading some mags and my parents were out, I got a bit too excited and realized I had to cum. I looked around every for a place to blow my load without leaving any evidence behind. I grabbed a sexy black high heel and blew my load in that.
After that I found that it was easy to clean so from then on I used high heels to blow my load in, after a while I would slide my cock in them, I loved it! I used a bunch of heels but always loved the black ones.
One night all I could think about was heels, so when my parents went out one night, I decided to wear some. The way they made me feel was amazing! I blew twice as much with heels on.
One night I saw a dress hanging on my mothers side of the wardrobe that looked like one that a girl in the porno mags was wearing, so I decided to dress up like her, slipping on the short white dress, I found some tan thigh-high stockings and a black bra and panties. My cock got so hard and I was so excited that I masturbated to myself in the mirror rather than the porno mags.
Every time they went out I would try on different dresses, bras, and heels. I already had long dark brown hair so when I dressed up, I looked like a hot young sexy girl, but when I wasn't I still looked like a boy.
It was such a thrill and I used to do it every chance I got.
After a few months, I got a job and started buying girls clothes for myself, as well as collecting some for girls I dated or knew. I still loved straight sex with girls A LOT, but loved secretly dressing up like them. I also got myself a laptop so I could look up porn and also buy clothes without anyone finding out.
I remember being dressed up like a sexy girl one night and was watching a porno. I loved old man/girl porn but I also loved all types of porn, especially hardcore stuff. I found a video where a girl was getting ass fucked hard in doggy style.
The guy blew a huge load, balls deep in her tiny asshole. He moaned and groaned, she did too. He slid his huge cock out of her ass, it looked so wet and delicious, my mouth watered, my cock hardened and I nearly blew all over my white Saturn dress I had on.
It throbbed and pumped out the last few drops of cum. They dripped down onto the back of the girls leg, as he held her ass cheeks apart. Her asshole was stretched open, gaped.
He grabbed a peep toe high heel off her foot and held it under her asshole. Hot sticky cum flowed freely out of her asshole, flooding the toe of the shoe. She farted the last few drops out. He gave her the shoe, and she held it above her mouth, pouring the cum out of the peep-toe.
My jaw dropped as she swallowed every drop, her tongue cleaning the inside of the heel of any leftover cum, and polishing the outside to make it clean again. It faded out and I was shocked, my cock throbbing, pre-cum flowing out of my tip. I had to try that. I grabbed my black peep toe shoe and barely even touched my cock and blew a huge load filling the heel. I'd never tasted cum before, but I was lusting after it, I held it up, tipped it forward, my mouth wide open, my tongue stretching out to meet the flood of cum.
It filled my mouth, my taste buds going wild. I held it in my mouth for a while before swallowing it down. I knew then and there I loved the taste of cum. I licked it clean just like the girl in the video.
I slipped it on my foot. it was warm and still sticky. From that moment, I knew I wanted to be a cross-dresser.
One thing I knew I had to do was shave. I was known among my friends as being kinda hairy, so a few weeks late, one night out with some mates, I made a bet that I would shave and wax completely if I lost, so I lost it deliberately.
i waxed regularly from then on to keep myself smooth. Now I could wear only a bra and heels and, with my long hair, I looked like a hot girl. I had shoes, lingerie, dresses and costumes, even some jewelery and accessories. I also bought some toys like a glass butt plug and a 5 string-anal beads.
All I wanted to do now, was find a partner to play with...
More stories to follow.