My first Sissy experience

I thought I’d share some of my first sissy/crossdressing experiences. Never really written anything like this before but thought I’d give it a go anyway.

As a child I always had a fascination with ladies clothing, I remember many different occasions where i would sneak my sister’s, mother’s and family friends panties and clothes to dress up in. I did this from around the age of 8, or at least this is the earliest memory I have.

When I was 9-10 years old, I became friends with a boy from school named Oliver. He was the same age as me however he was very tall. Oliver always seemed very feminine and had interesting hobbies such as sewing and fashion. After a few visits to each other’s houses our parents quickly became close friends. This led to us spending a lot of time together.

We started off very innocent, just topping and tailing (sharing a bed) as friends of that age do. One day for reasons I cannot remember we became fixated on the concept of g-strings, as we were young we of course couldn’t go and buy some, so Oliver decided we should make a pair each. It was disastrous, we essentially chopped up a good pair of satin boxers. Next we move onto to skinny dipping in his pool and spa and then finally nude sunbathing on a tin roof. Throughout all of this we both remained very straight acting and innocent like.

One day Oliver brought out a dress up box that he had been given to use as materials for sewing, it was basically a collection of dresses 👗. We began to try them on and ended up wearing these dresses all the time we were together. When it came to bed time we would both sleep naked, him on the bottom bunk me on the top.

One day Oliver asked me if I had ever played with my ‘diddle’? To which i lied and said no. He suggested that I should try it and described how he liked to play with his. We both decided to play with ourselves and I had my first orgasm. A bit shocked and worried I asked what I should do as I had cummed, he said don’t worry just wipe it on the sheets. That night he asked if I would like to join him in his bed, to which I said yes. We were both laying naked next to each other when he reached over under the blankets and touched my dick. I liked it! I did the same, and soon we were masturbating each other’s dicks. I liked to have him stroke mine while he liked his to be flicked. We finished up with a bit of humping and Rubbing our dicks together.

Form that point on we would always be sneaking off together to play with each other. At age 11 we began to run each other’s dicks over our faces and mouths and eventually began to touch and kiss each other’s ass holes. For some reason we never thought to actually put our dicks in each other’s mouths but I really wish we had. One day Oliver asked if he could rub his dick against my bum, I said yes. He proceeded to rub his dick sensually against my butt crack, and eventually he started to press the top of his penis against the entrance to my ass. At first I really liked it but after a thrust too hard his penis entered my ass, I screamed as it hurt and he suddenly took it out. We unfortunately didn’t ever try penetration again.

At age 12 for reasons I can’t really remember, out parents stopped hanging out and as a result we drifted apart. To this day I haven’t actually seen Oliver but I regularly remember and get horny thinking about our time together.

If for some reason we ever get back in contact I’m going to make sure i sick and take all of his big cock!

Thanks for reading hopefully you enjoyed it .


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