100%

My young life

51 yr old crossdresser thinking back upon his introduction to sex

It all started when I was in third grade. That is when I started to crossdress. I would strip down and put on my mom’s bra and panties. Even though they were too big for me it was exciting. I was thrilled. My heart beat faster, my breathing increased, and I reveled in the pure joy of dressing up. My little cock would jump at every movement of the silky fabric of the panties. I would walk around in front of the mirror and admire how I looked. I ran my hands up and down my body. Feeling my hard cock push against the fabric making a tent of the panties. I would also slip on a pair of heels. I liked how they forced my ass up in the air.

One day I was walking around dressed up when my older brother caught me. He told me in order to be a true girl I had to climb on top of him and get him off. He disrobed to his underwear. I was still dressed so I climbed on top of him and started grinding my hips into his body. I felt his cock getting hard. I continued to work my hips rubbing my cock on his through the panties. Suddenly he thrust his hips up in the air. He came in a big moan and shot his cum all over his underwear that also soaked into the panties that I was wearing. I had many emotions running through my mind. I was elated that I made him cum. I was scared. I felt dirty. I wanted more. I wanted to make other guys cum. I knew the power of being a woman.

I continued to dress up in bra and panties in the following years. I met a guy in middle school. His name was Wayne. I would have sleepovers at his house. We would listen to music and talk about the kids we went to school with. We would play with other kids in the neighborhood. I would wear bras and panties while we did these things. I would change in his bathroom when getting ready for bed. I played it off as my being modest. I didn’t know how he would react to me wearing my special clothes.

On one particular sleepover we talked his parents into letting us sleep in their camping trailer. After dinner, Wayne and I went out to the trailer and made it ready for our evening.

To read the rest of this story, you need to support us, over on Patreon, for as little as £1.99

Join here: patreon.com/FantasyFiction_FF

Rate this story

Average Rating: 0 (0 votes)

Leave a comment