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How I learned the pleasures of anal

This narrative is the journey that lead up to my first experience with anal sex. The details I have here are as accurate as I can recall and any dialog is essentially the best of what I can remember now. It of course gets more sexually explicit and graphic towards the end...

I was born and grew up in what many would probably call an average small suburb. In my early years, while starting puberty I began to explore sex the way I assume many boys across the world did to start. A few times during this period I became curious about girls and what made them so different from boys. One of the obvious differences were in clothes. Bras, thongs, dresses, skirts, and bikini’s vs suits, ties, boxers etc. Girls always seem to have much more variation in styles and I was always curious why. During this exploration, I decided to try on girls clothes a few times and see what some of them were all about. When I did it, it wasn't done as anything “sexual” but I do recall that it did make me feel different in a good way. This is where my appreciation for femininity started, and what ultimately, many years later, lead to my transition.

I was constantly exploring and once I hit puberty, growing to be a hormonal teenager, none of those curiosities died out, rather, they only increased in voracity. Sometime during that time I discovered the pleasures of masturbating and sometime during that time (while also having access to the limited internet at the time) I was able to explore pleasure outside of masturbation and I found anal stimulation to be very exciting. While exploring myself anally I never did think to call into question how that could have possibly related my gender identity nor did I think of what it meant about my sexuality in any way. I was biologically a boy, enjoyed masturbating, very thoroughly enjoyed anal stimulation, and enjoyed dressing like a girl. It wasn't till the mid-teen years of course that I bothered to start to call into question if my appreciation for those things related in some way to my sexual preferences or sexual identity. I certainly didn't reach any conclusions at the time but didn't let the internal exploration of it worry me too much either. I was who I was.

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