How I learned the pleasures of anal

When I arrived at his door, I knocked and within a minute he opened the door (felt like a long 5 minutes, but was probably closer to 30 seconds). He was an average looking guy who was about my height, he invited me in. I was so nervous I am not sure I said anything intelligible but just followed him into the house. He asked about 3 times if I was sure I wanted to do this and every time I nodded yes, so we slowly made our way to his bedroom.

It was a very, very nice house and everything reflected that. When we got to his bedroom he had some slow music playing in the back ground and the room was dimly lit. I noticed he had a few things laid out on the bed and so he noticed me checking them out. He gestured towards them and said something to the effect of, “I have a few things here… if anything interests you let me know…”. First thing I recall noticing was a set of lingerie, a silky/lace nightie with matching bra and thong. He said something like “I know you said you like wearing girls clothes so you can wear these if you want…I bought them for my wife, but never gave them to her…”

I had actually already had on the stuff I borrowed from my house so I said, thanks, and that I really liked them but I had already been wearing some. I then began undressing the boy clothes I wore to show him what I had on underneath. I was not sexually attracted to him, but was so sexually excited by the idea of what could happen, I knew I wasn't going to leave until I tried it. As I undressed and stood there in my thong (it was pink and a little too small for me as it was my s****r’s) and bra (which was black and a few cup/bust sizes too big for me), my heart pounded and there was an obvious excitement growing down below. I had just started shaving my face at the time, although I didn't really need to do it much, but I had also shaved off all of the hair from my body with the exception of my arms and legs (again, not all that hairy, but not as feminine as I would have preferred…) because I was uneasy about the social stigma surrounding boys who have shaved bodies and didn't really want to have to deal with that when someone noticed.