How I learned the pleasures of anal

I knew I was attracted to girls and never really was attracted to boys in the same way I was to girls. I did, however, have curiosity about how they could potentially (or not) fit into a situation that I would find sexually pleasing considering my fondness for anal. This curiosity persisted but it wasn't till I was 17 that it ultimately lead me to trying to find someone (using the internet) that I could explore my anal sexuality with. I knew I was very intrigued by trans-girls, but with the somewhat-small town I lived in, I knew there wasn't going to be any chance of me finding one to get to know and learn from, so I figured a guy to experiment with sexual was just as good, at least for those earliest experiences. I started chatting in adult forums and found a few adult oriented sex sites and ultimately stumbled upon a gay site with guys who were local to try and seek a guy who would explore the phallic sexual experiences with me of which I was so curious.

I found a guy who lived about 10 minutes from me and we chatted for days and days and after a few weeks, I finally decided that I wanted to try it out genuinely, my curiosity and sexual drive outweighed the potential stigma or concern I had about what it actually meant for me to do it…essentially I was too horny to resist. I had been playing with anal insertion a good bit, trying to find phallic shaped “anythings” I could get my hands on to pleasure myself… a few vegetables and bananas suffered a horrific fate as some of those random objects. I arranged to meet a guy, in his late 30s, at his house. His f****y was away on vacation while he worked so he invited me over. I borrowed a few pieces of clothes from my mom and s****r which I wore under some of my regular clothes when I went over to his place.

When I got there I freaked out and was of course nervous about what it meant. I ended up just getting too panicked and went back home and apologized the next day for flaking out. That happened once more that same week and before I finally pulled up to his place 5 days after that original set meet, I decided to actually go through with it.