Where it happened: Hotel Room in Wisconsin
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first sex was gay sex. He and I had been dating for the summer. We both knew in the back of our minds that we weren’t going to last much farther than that. I had just graduated from high school and he was one of my (now former) best friend’s college friends. I thought he was cute, and there was something oddly fun about dating a Jewish boy.
Anyway, I had just discovered the band O.A.R. and saw that they were playing at Summerfest in Wisconsin. It was about an 8 hour drive from my house in southern Iowa and I decided I was going. No one wanted to go with me, even He didn’t want to go all that much, but he decided that he would just because I wanted to go so badly.
When we got to summerfest, I was relatively enjoying myself wandering around, listening to the bands playing before O.A.R. When it finally came to hear the band I came to see, we could barely see them, they started 45 minutes late, and we were being pushed around by drunken, high people just generally being irritating. After not hearing, seeing, or even having a good time, we decided to go back to the hotel room.
When we got there, we immediately got to the bed and got busy. We were making out, tongues lashing in and out of each other, grasping at each other’s clothes and cocks through our jeans. I started to go down on his rather small cock. Whenever we would be naked with each other, I would comment on how I was the big man of the relationship. He told me to shut up usually.
I suckled his balls and taint and dick as he writhed and moaned and played with my hair. Finally I came up for a bit, looked at him and asked him if he wanted to fuck. He said yes so I got off the bed and went to grab a condom from my overnight back. He did the same thing. We clearly had the same idea about coming on this trip.
Then we both realized that we forgot the most essential thing for gay anal sex: lube. He said not to worry and began spitting in his hand and rubbing it against his hole. I did the same thing, only applied it to the condom on my cock. He was on his hands and knees on the bed and told me he was ready. So, I put my basically dry cock into his ass. It was a slow process and probably didn’t feel good for him. He told me to just wait a second so that he could readjust and feel good about it. I started to pump my pelvis into his a bit but he said it didn’t feel good. He flipped over to his back and threw his legs in the air to let me re-enter him and try it at that angle. Still didn’t feel good.
We decided that that night just wasn’t the time for us to fuck each other. He ended up giving me pretty decent head, with me screaming his name and lapping up my cum from my stomach.
When we got back to Iowa, he didn’t call me for three weeks. Our birthday was three days apart. I bought him a present, which I kept. I ended up breaking up with him via MySpace because he wouldn’t take my phone calls, text messages or IM’s.
He’s dating a “nice Jewish girl” now. I hope she enjoys his small penis and his taking forever to cum.
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