Although this happened a long time ago I'll never forget my first experience so I'll write this as best as I can remember, I hope it invokes memories of your first experiences.

This happened unexpectedly when after a night out on the town with my long time friend I crashed at his place.

I'd sort of known for a while he might have gay feelings, I wasn't sure if he knew that I liked wearing women's clothes but I guess sometimes you just know but too afraid to ask.

So the time when it came to go to bed , he got into his three quarter bed and I had the floor.

We talked a while, perhaps building up the courage to ask, he said I could share the bed with him if it was too cold and uncomfortable on the floor. I took my time in answering but eventually said ok not trying to sound overly keen, " no funny business" he said with a laugh. I got in but hadn't noticed he was wearing a silky chemise,  how the hell did I miss that! He must have slipped it on whilst I was in the bathroom. That had the effect I guess he'd been planning for and things were beginning to stir in my boxers, he did ask if I was ok with him wearing the chemise, I stuttered yes, he just replied thought you would then explained he liked wearing ladies night wear to bed and asked how I felt about it. Blushing, I admitted he looked nice in it and that I'd occasionally worn slips and panties. That was like lifting a weight off my shoulders, being able to share my secret without fear of being outed..

' would you like to feel it on me ' he asked, he rolled over onto his front then I nervously put my hand on his back and slowly stroked up and down his back, it actually felt amazing as my fingers slipped over the shiny material, he made an approving moan and asked me to tickle him as he liked that. I did as asked from his shoulders to his pert satin clad bottom I'd not yet seen as the covers were still covering our lower body

He seemed to be enjoying this attention then he said something I remember word for word which was, ' ok, I'll be the woman, take your boxers off and get on top of me' by now i was Rock hard and ready for anything so pulled back the covers and removed my boxers and laid on top of him with my cock resting on his bottom then started to rub up and down his panties. After few minutes he just said stop, I thought that was it and he was getting cold feet only to say pull my panties down and carry on.

I slid them down his legs then straddling his closed legs got my cock which was now wet with my own juices back onto the crack of his bottom and continued to run up and down 

This went on for a few minutes until I started to feel I was about to cum, he must have  sensed  this as he clenched his bottom cheeks to make a bit more friction for my now slippery cock to slide up and down then it happened, I increased my speed and increased the pressure to get as much sensation as I could on my strokes, then I started cumming just as I was sliding on the down stroke then on the up stroke whilst still spewing out my sperm it stopped dead as I pumped away then slid up again watching the last Spurts shooting up his lower back and bottom , My first time. I got my breath back and he got off the bed and  cleaned himself up with my sperm all over his bottom and lower back , not as much as I normally produce but I guess first time nerves? 

He then went to the bathroom to clean himself up but it seemed to be a while, he came back looking a bit sheepish explaining  that he had to clean up the sperm leaking from his bottom and that's when I realised what I'd done.

Not the best introduction to anal sex but one I'll remember for the rest of my life.

I slept back on the floor not knowing what to do as I guess his cock needed attention but unsure what to do although I soon got over that after a long chat with him  any awkwardness evaporated

We did have a few sessions after that with me going all the way, what an introduction to the world of crossdressing and the many adventures over the years.