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 .


Me and my girlfriend had been dating 2 years when we finally got a flat together. Everything was going good until I met Anna. She was our married neighbour and in her late twenties. She started seducing me when my girl wasn’t around and in no time we started fucking. She was older and she gave me some of the best sex I’d ever experienced. The problem was she was a bit too extreme at times. One day she put my cock in chastity which meant I had to withhold sex with my gf. She just found it funny and made me suck her strap on before her husband got home.

She was crazy but I was hooked. I kept seeing her. One day she said she’d give me the key to my “clitty cage” if I let her dress me up as a girl. At first I refused but I didn’t have much choice to be honest, so I changed my mind and said yes. She made me look so girly then said we were going out! I told her no but then she took pictures of me and said unless I want my girlfriend finding out then I better obey! She dragged me to some dodgy looking video store.

A lot of guys were staring at my crossdressed body. I had a short skirt, huge heels on and so much makeup. I looked like a prostitute. Anna took me into a bathroom stall and forced me to my knees. The next thing I know a cock appears from the bathroom stall next door. I try to escape but Anna starts phoning my girl. “Ok ok I’ll stop escaping!!”. She smiles and and tells me to suck the cock. Reluctantly I take it in my mouth. I hear a moan of pleasure from next door. This is unbelievable. Anna whispers to me that I need to get into the blow job more or she’ll tell the world what a sissy slut I am.

I decide that I have no other choice so I might as well try make him cum faster. I start licking his rock hard cock the best I can. I suck and lick his balls just like Anna had done to me only a few weeks ago. I noticed Anna was video recording the whole thing but it didn’t make a difference. I gave this stranger the best sloppy blow job I could and eventually he started cumming all over my sissified face. I swallowed some of it and it actually tasted quite good. I ended up eating the rest of it that was on my face.

Anna was impressed with me. The guy from next door came round and kissed Anna! It was Alan her husband! He spoke to her, “she was amazing honey, where did you find her?”. Anna responded saying, “I’m glad you think so, she’s from closer than you would think honey! I’ll keep training her until she’s ready to go all the way”… shit

This is like my absolute favourite fantasy 😍😍