Bottoms Up!

A gay man’s first time bottoming is usually a memorable experience. Sometimes it is a good memory, sometimes it is a bad one, and sometimes that memory is if, well, a very awkward experience! Now, can you guess which category my first experience falls under?
Back in my college days, my friends and I would have to drive an hour to get to the nearest gay bars. So, drive we did, every damn weekend! The bars would allow 18 and up in, so it was a little piece of heaven we would all partake in. We had a rule that anybody hooking up with a stranger had to make sure the group met and got contact info of said stranger first. It was a great system that kept us all safe.

One night, I met a man just a few years older than me who struck my fancy. At this point in my life, I had only been sexually active a short time and could count my partners on one hand. This man was gorgeous and very into me, so I had him meet the gang. I was the one with the car in our group, so had to make arrangements with my roommate to pick me up the next day. 

At the bar, and on our way to this guy’s house, we talked about our sexual tastes. I implied that I was a big time bottom and loved getting fucked. The reality of the situation was that I had never bottomed before, but for some reason I thought that might be a turn off for him (really… 18 year old virgin ass a turn off? I can be so daft).

We made it to his house where we immediately made for the bedroom. We made out for quite a long time, and took our time getting them dressed. The night was still young, and we were just really enjoying every inch of one another. As soon as we got undressed I could not keep my mouth off of his cock! It was so beautiful, and all I could think about was taking it in my ass. We got a condom on, he laid back, and I hopped on top. Not having done this before, I had no idea that I should probably take it slow and that I should probably ease myself down his shaft. Oh, no, not I. I lubed my ass up, grabbed a hold of his cock, and sat all the way down. It was so obvious to him that I sat on more than I can take, the pain was so intense and I tightened up so bad, that he was done with that act. I was so pissed at myself! Things of been going so well we were having so much fun we were enjoying one another so intensely, and then my awkward self screw it all up. I apologized to the man profusely, he just laughed and said “this is really your first time isn’t it” I admitted it was, and he said that he wouldn’t dream of making me go any further, so we ended the night with some mutual masturbation, some oral, and plenty of juices all over one another!

The next morning, we woke up, had some coffee to wake her selves up, and decided we would need some of his friends for brunch while we waited on my friend to pick me up. I honestly still could not get over the awkwardness that I had created the night before, and the fact that I got busted in a really big lie, so I literally just sat there quietly the entire brunch, and was so glad when my roomie showed up to take me home.

You would think that this would have taught me not to tell stories to try to get a man. Right? Well, my friends, by now I’m sure you know that I did not learn such a lesson! There have been other such instances throughout my life. But those are all stories for another time.

Until next time,



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