First Gay Anal Sex - Sex Stories

First Gay Anal Sex

So after my first time with a man on here, I was a little hesitant to think about trying anal for the first time. Bill was pretty rough with me during the blow i gave him, not that I didn't like it just if that was my first time having anal too well I don't think I would ever walk straight again afterwards.... But I was so ready to find someone to bottom with, just not him for the first time. So my search began again online, and oh yes there were more than a few suitors, just wanted to keep my virgin ass working after the first time. Oh and believe me I started getting ready well in advanced, I bought some really big dildo's so nothing would be too big for me.I would like to add that having anal with my girlfriend turned me on to having gay sex. She was really curvy, huge tits... Totally willing to try new things, got her asshole nice and ready for me to fuck. I put a condom on at first, once i started going I pulled out and noticed the condom totally broke, felt so fucking good I just ripped it off and fucked her bareback. Didn't have to worry about her getting pregnant so I came in that ass good. Afterwards she asked if I would be into fucking a guy since it would have felt the same, totally BC it felt amazing. And seeing how much she loved it, I wanted to try it as well...Found a daddy more than willing for the job. Lived in a nice neighborhood, married with k**s and the works. But another with the wife not giving him any. He had a few....odd requests. But it ended out being loads of fun."Tom" didn't want to do names, or even faces. But he did want to record. He gave me his home address. Nobody would be home, just him inside waiting. Was a really nice neighborhood, talking million dollar houses. Lots of space between them, which would come into play because he told me to come to the back door completely naked. I was to wear a mask thou, both of us would. I pulled up outside the house. No lights were on. It was about 2am. Nobody around, a little foggy, a little cold. I casually walked into the back yard and unzipped my duffel bag. Stripped all my cloths off and put them away. Put on my little ski mask, grabbed a big bottle of lube, and walked up to the back door. I made sure to shave every hair off my cock, around my ass and even off my but. I was so smooth, and walking up to the back door with that cool breeze hitting my smooth balls and ass.... I was so ready to get fucked. My ass actually hurt a little bit already, I worked myself over with my dildo's already before I got there. Oh I was ready, asshole already lubed up, even leaking a little lube as a walked. The door opened for me. And there he was, "Tom" was ready for me. Totally naked too, overweight, big beer gut, hairy....cock was semi hard, it must have been about 6 inches and cut. White guy wearing a Luchador mask of all things, told me "upstairs, first door on the left". I remember the bed, huge california king with lame silk sheets on it, only the bottom sheet was left on the bed. ...