I am now 58 years old. I have been single 99% of my life. Because of being single all my live I have ended up dating more than 200 women and have had sex with well over 1000 women. Mostly one night stands or multiple fuck buddies at a time. Many of the one night stands I ended up having anal sex with a few.
I did have many relationships though. Over the years I had several women that absolutely loved anal. One of the women I dated I have written about and posted pictures of her here in this forum was one of them. She was a blond with a high sexual apatite. When we first started dating we were having sex every single day and some days two or three times a day. One night we were parked in an ally and I was giving to her doggy style in the front seat of my pick up truck. I stuck my thumb into her asshole and she seemed to like it a lot so I asked her if she wanted me to stick my dick in her ass. She said yes so I did. She got off on it and came hard and I ended up cumming in her ass. The next day I asked her about it and she said it was her first time and she loved it. I said whenever you want it again just tell me. She said I want it right now, so we did. From that day forward I fucked her ass every single day for 2 1/2 weeks and never once stuck it in her pussy. Some days we fucked two or three times a day in her ass.
The sad ending to this is we went out of town on a business trip. We were at a motel and we were getting ready to have sex. She was being a good little trooper and was trying to be creative because we didn't have any lube. She brought some hair conditioner and put it all over my cock and when I stuck it in her ass it started burning her. we had to end it real quick and she jumped into the bathtub to try to stop the burning.
From that day forward anal was a once in a while thing. She said she still loved anal and still wants to do anal every time but it caused here discomfort. We still done anal from time to time but not as much. That was too bad it had to slow down.
fast forward a year or two later. we met some friends at a bed and breakfast. I cannot remember the conversation but we ended up in the other couples room having a foursome. The other girl was on her period so I did not fuck her but my girl licked her pussy and her husband fucked her ass. As he was fucking her ass I was fucking my girl while on my back and her on top with her ass toward them. As he was fucking his girls ass he was fingering my girls asshole. She was whispering in my ear how he was sticking his fingers in her ass while my cock was in her pussy. I asked do you like it? She said yes.
The other guy pulled his cock out his wife's ass and stuck in my girls ass. My girl was now getting double penetration. As she was getting into it and started rocking back on both of us at the same time. We all three had an orgasm at the same time. I came in her pussy and he came in her ass.
I loved that girl and wanted to marry her. But she ended up leaving me for some rich dude. She now lives the life having three houses. One house on the lake and one in the mountains and another in Florida on the coast. I think back to all the wild and crazy fun we had and I still jack off to the memories with her form time to time.
Since then I have had two other girls that I would say they prefer anal sex over vaginal sex. The current woman I am with is that way. I am over twenty years older than her and at my age I am having a hard time keeping up with her sexual needs. But I am enjoying trying. She comes to me almost every day telling me how much she wants my cock in her asshole. When I am at work she will send me videos or pictures of herself fucking her ass with a giant dildo. She will masturbate or should I say she analbates at least two or three times a week on top of me fucking her ass two or three times a week.
I have quite a few more stories about women that enjoy anal. I just wanted to tell about the women that preferred anal over vaginal sex. here are tow pictures. One of the blond from twenty years ago and my current woman.
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