Author: DetachedAmusement

[MM]Throwing caution to the wind: Giving a blowjob to a random stranger

I’m probably what you would consider bi. I’m very open-minded and I’ve experimented sexually many times. The first time I had sex with another male was with a close friend of mine, who I could consider straight, but he was going through a long period sexual frustration and I helped to get him off in more ways than one. I won’t go into detail on that one, because we were in high school (tee hee), but it expanded my horizons as to what I enjoyed sexually, primarily that I really get off on pleasing others.

A few years ago, I found myself bored and feeling adventurous one weekend, when I decided to visit a local porn/sex toy store. This place has an adult theater, which I’d never explored, but today I got curious about seeing what it was like. I made my way down the dark, seedy hall that led to the theater, checking out the doors of each of the booths, until I found one that was obviously empty, and I quickly ducked into it, closing the door behind me and locking it. Read more »

Going to the limit with an anal toy 28[M]

I learned early on that I had a thing for anal play when I was young and accidentally slipped a soapy finger up my own ass in the shower. I was shocked that it happened and more shocked that I enjoyed the way it felt. I was even more surprised, years later, at how much I enjoyed it when a friend I’d been experimenting with asked me if he could fuck me. After a disastrous first try, we did it again and I couldn’t believe how much I loved it (no details on that here, as we were in high school–hee hee).

So a few years ago, I decided to indulge my own love of anal penetration privately and set out to buy a butt plug to play with on my own. Admittedly, I got greedy with my first purchase and bought one that was way too big. At it’s base, it was probably six inches wide. The first time I lubed it up and started to slide it inside me, I could tell I’d been overly ambitious. Read more »

My journey to wanna be sissy cumslut 28[MM]

I had always been curious about having sex with another man in my younger years, to be honest. I was straight and mostly thought about women, but I occasionally had fantasies about what it would be like to try gay sex. One day, it happened with my friend Brian.

I have to preface all this by saying that I’ve always been very effeminate in appearance. I have long brown hair that’s very soft to the touch, big green eyes, and full lips. I was mistaken for a girl many, many times in my youth.

I don’t fully recall how it came up. We’d been smoking a joint together and Brian was complaining about how long it’d been since he’d hooked up with a girl. Somehow, we started talking about whether either of us would be open to experimenting sexually with another man. I could feel myself blush a little as we talked about it, perhaps giving myself away. He suggested that maybe we could give each other blowjobs, so long as we kept it our secret. I was hesitant, but curiosity overtook me and I agreed. We both stripped naked and proceeded to give each other head. Read more »