My first anal story
When I was in Highschool. I was working as a lifeguard. There was this blond that worked with me that was the same age as me. We started hanging out with each other after work every day and it didn’t take long until we were fucking every day. After us fucking for about a month we started experimenting, trying different positions, we tried fisting and we found some toys and a few other things. Then one day I said let’s try putting it in your ass.
She was up for it. It took a lot of trying different positions and going really slow. At that age it didn’t dawn on me to try lube. She was saying it was too uncomfortable and it hurt I was ready to give up but once I got it all the way in, she started getting into it. She started pushing back and started grunting which she had never done before. I felt her asshole loosen up around my cock and it felt like she was getting wet. I looked down and I could see my cock going in and out very easily. I didn’t want to cum yet so I pulled out and her asshole stayed open. That was the first time I had ever seen a gape. She was saying put it back in, put it back in! I was saying hold on because in my mind I didn’t want it to end if I came. She was almost getting mad at me for taking my dick away.
When I finally got control of myself, I put it back in and she started moaning loud and started bucking up against me. That didn’t take long until I was cuming deep inside her asshole. We went home to our respective houses and I couldn’t stop thinking about it. So, I waited until bedtime and I called her. After some small talk I asked her if she liked it. She said yes but it was painful at first. I asked her if she wanted to do it again and she said yes.
So, the next day we met in the locker room after the pool closed and we were the only ones there. She had brought some KY jelly with her. This time she lubed me up and she put some in her asshole and when I got behind her, doggy style, she said go slow. I just put my cock on the entrance of her asshole and kept still. I let her do all the pushing. She went slow and after the head was in she held real still. She said don’t move. After about a minute she pushed back and she started rocking back on me and I just sat still and she was the one doing all the work. She was fucking herself hard and deep. She started grunting again.
After she came real hard I wanted to take control. We were in the doggy position. I grabbed her without taking my dick out of her and I positioned myself on my back and her back to me and her on top. I reached around and started fingering her pussy as I was fucking her ass. It didn’t take long and I was cumming in her ass. After that summer we went our separate ways. She got married and had children and I moved out of state.
But one time I was visiting in town and we accidentally ran into each other. We talked and agreed to meet at my motel room. As soon as we started fucking, she said lets do anal for old time sake. I was happy to oblige. I asked, did her and her husband do anal and she said yes but the kids kept them from having sex as much as she wanted too. Anyway it is all great memories for me.
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