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So, my wife’s first time with anal was not with me! A little backstory about our relationship. My wife and I have been married for 10 years and have a great sex life. We are both professionals with demanding jobs. My wife is a brunette around 5’6” tall, perky B sized breasts and in great shape. I am around six feet tall with dark hair and an athletic build. We are currently in an open relationship. My wife enjoys the guys she plays with, but they usually don’t last long enough to give her an orgasm. I usually get that honor with reclaim sex. Regarding our sex, my wife takes a very long time to climax. On the other hand, I have trouble finishing so it all works out, and our sex sessions are usually very long. My wife needs both her g-spot and clit stimulated at the same time to climax, and this is usually from penetration. When she finally has an orgasm after a long build, her contractions and spasms are so strong you can feel them on your dick. Her quivering pussy almost always makes me cum and is like the ultimate reward after a long sweaty session of sex.
So, my wife was a software engineer but recently changed to software sales and training for the money. This requires extensive travel. She finds herself very lonely traveling with her job. One of the things we worked out is that she can play but it must be at the hotel for safety reasons, and she must record it. Many times, it is livestreamed, and she enjoys knowing I am there, and we are all are getting off together. She ends up meeting someone around 30% of the time. Many times, the guy has no interest in being part of a livestream.
So, the last time she was in Chicago, she met a guy interested in playing with her. They had a very hot play session fucking in most sex positions. It was a lot of fun to watch. He was a little smaller than me but had incredible endurance and was very athletic. After over 40 minutes of sex while they were in the missionary position, he made her orgasm very hard. When she came, one of her contractions was so strong it forced his cock out of her, and he missed out on her quivering vibrating pussy that probably would have made him cum right away. After her orgasm faded and she caught her breath, she asked him what she could do to get him off. He suggested anal sex. In the afterglow of her climax, she said yes.
Now with my wife, I have never tried anal sex with her. She told me because of what she needs to orgasm, anal sex could never make her climax. Our current sex sessions can last from 15 minutes to an hour to make her cum. They are already so long; we just never went there with anal sex. I have heard other play friends ask her for it and she always says no. To be honest, her pussy feels so good when she gets off, I never had an interest in it and love the connection we have when we mutually climax, which is all the time. When she cums, I cum (partly because I am exhausted and ready for a break).
So, I am watching the livestream with my wife and this guy and all the sudden she rolls over from her back to her stomach, and I see him applying lube to his dick. Then he takes his hard cock and starts working it slowly in her ass. I hear her moaning but can’t tell if it is from pain or pleasure. After about a minute of him working it in, he starts pumping her ass hard and fast. It was one of the most exhilarating things I have ever seen. I take forever to cum myself and started to stroke myself and ended up cumming when I saw his dick go balls deep in her ass and make her moan. My wife’s toes were curling, and her face was buried in the pillow as she moaned. They moved from doggy to prone bone, and he kept pumping away. Finally, after around five minutes, he came in her ass. So, we have 9 years of open marriage videos, and I keep watching this one and it makes me cum every time. I must have watched it a dozen times.
My wife and I talked about it when she got home. She has offered me anal sex and I said no. Not to sound pompous, but with my slightly bigger dick I don’t want to cause her pain. Plus, our dynamic is all about getting orgasms and she said anal just won’t do it. So, I asked her about the moans and if they all were from pain. She said no that she could sometimes feel pressure on her g-spot, and it felt good. Then in prone bone, her clit and g-spot would sometimes get stimulated and that made her moan, and she even had a slight build to another orgasm. I asked her if she would do it again and she said probably not.
So, watching another guy take something she has never given me is kind of driving me crazy and I don’t know what to do about it. I kind of have an itch to scratch and think maybe one session of anal with her might help me with this dilemma, but I kind of hate the idea of doing something that I know my wife will not enjoy. It feels a little selfish. I have never done anal and don’t know anything about it. I mostly like getting other women off, and this has always been with regular fucking if that makes sense. So, do you think we should just do it briefly to get this out of my system, or do you think I should let the idea of doing anal with my wife go?
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