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 and 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 bodies 

He seemed to be enjoying this attention then he said something I remember word for word which was, ' ok, pretend  I'm  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 satin panties leaving evidence of my excitement. After a 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 straddled his  legs, now spread wife apart. I got my cock which was now wet with my own juices back onto the crack of his bottom and continued to rub 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 the mattress started to bounce up and down with my now urgent strokes pushing hard down onto him  ,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, this was too much for me and I couldn't hold back any longer, that familiar tingling from my cock as I started to ejaculate on his bottom  just as I was sliding on the down stroke then on the up stroke whilst still spewing out my sperm it unintentionally stopped dead on his hole as I pumped 2 maybe 3 spurts of cum into him 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 with some dripping down his inner thigh, I didn't realise at that time but I'd just inseminated my friend!  What I could see was that I'd not produced as much spunk as I'd normally produce but I guess first time nerves? 

He then went to the bathroom to clean himself up but he 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 I was unsure what to do, my biggest regret was not getting back into bed with him and I still think what could have happened although I soon got over that after he told me not to be ashamed at what I'd just fine and he actually liked it, did I? Well yet again the barriers I'd built up to protect my secret were slowly coming down, I had to choose my reply very carefully, my face burning bright red I replied with one word ‘ yes' from that moment onwards   any awkwardness between us  evaporated.

We did have a few sessions after that with me going all the way before the tables were turned on me!  What an introduction to the world of anal sex and cross-dressing, the start of many adventures over the years