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My First Anal Experience

First time M/M sex

This is my 2nd submission of my true experiences. My first story is how I experienced my first Contact with men, giving and receiving blowjobs through a gloryhole.

Months had passed since my first experience but that first experience had a great effect on me. I started going every Friday night for some quick action before I headed home from the clubs. I also like going to different bookstores because not knowing the layout and exploring the whole place was exciting.

On one particular night I did try a new bookstore and quickly found a booth with a GH. When I heard someone enter the other booth and saw the fingers through the whole I went into action. I put on my condom and stuck my dick through the hole but nothing happened. I heard a lot of movement and then the sound of his belt being undone and his pants going down. It was normal noise you hear all the time so I thought nothing of it. All of the sudden I feel pressure against my dick. This was not a warm mouth taking me in so I was confused as to what was going on when it hit me. He kept moving in and out and I realized he was trying to get fucked. All of the sudden my juices started to flow really hard. I finally felt my head enter him and slowly little by little my dick was inside him. I did nothing but let him do all the work and about three minutes of this I came. To this day I do not know how I entered him without lube. When I left all I could think about was how it would feel if I had someone do me. After three weeks of attempting to do this then chicken out at the last minute, I went for it.

There was this one bookstore that had some really good holes and action. It was late Saturday morning; I bought some lube and several condoms then headed to the bookstore. The place was packed with guys. My regular booth was being used so I started to walk around. I walk into the movie theater area and while watching the movie I noticed a tall guy in his late 30’s, long blond hair checking me out. After a while you know what certain looks mean and I knew he was looking for action. I decided to go back to the booth area and wait. As I settled against the wall in front of my favorite booth and wait for it to be free when the tall blond came by and settled himself in front of a booth which happened to be next to me. I could see in the corner of my eye the guy looking at me.

Finally! The door opens and I enter the booth, at the same time the guy in the other booth leaves so I know the Blond hair guy is now in the booth next to me. I begin to flip channels until I find a video I like. Looking at the hole I see the guy looking through the hole waiting for some action. Feeling brave all of the sudden I put my fingers through the hole and invite him to put his dick through. When I saw his dick I was shocked. It was big! Too big for me to have him fuck me, this was going to hurt. I start off giving him a blowjob, at the same time I finger myself to try and loosen myself up. I’m ready, so I take the lube and put some on the condom and some in and on my asshole.

The guy begins to insert his dick and I feel pain so I pull away and wait for it to go away. Again he tries but he is slow about it as if he knows he hurt me the first time. Once he is fully in he begins to thrust in and out real slow. Man, I started to enjoy it. This was one of the best feelings I have experienced. I could not believe how good this felt! I kept adding more lube and he kept pumping faster and faster. Looking down I noticed I was cumming! Not once did I touch my self and there was cum dripping from my dick. My whole body was relaxed and enjoying the experience. The guy started to thrust as fast as he could and then he came. He was in me for another 15 – 20 seconds before he pulled out. I did not hang around for the next guy or clean myself up.

I left the bookstore and went straight home to shower. As I was cleaning up I realized I was still horny. Even though I was cumming during the fuck I never really got myself off. As I masturbated I imagined the blond guy fucking me. Three fingers were in my ass as I played with myself. I came very hard and my whole body felt like it was cumming.

To this day I wish I had hung around to talk with the blond hair man. I would have loved to been his fuck buddy. I never saw him again but what he did to me that day left me wanting more. And I did get more but that is another story for another day.

I hope you enjoyed my story. Please contact me and let me know what you thought. I love to hear from everyone.

End of Story