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The original was posted on /r/sex by /u/ordinaryfaze on 2023-06-27 09:34:18+00:00.


My (29f) boyfriend (32m) and I have been together for 3 years. I know that he’s been pegged by a previous situationship from before we started dating and said he liked it. I know he uses anal toys when he masturbates but he doesn’t want me to peg him. I’m very interested in pegging him, I even ordered all the stuff to do it but he says he’s not interested. I’m having a hard time understand how he likes anal toys and has had a good time with pegging before but doesn’t want to do it with me. I can only assume it’s a me issue, do any guys have some insight to this? What can I do to make him more comfortable ?

  • @Guatch
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    11 year ago

    It’s difficult to really speak on your personal experience. Because I’m not in your relationship, or in your S.O. Head. All I can offer is my experience, and recommendations based on that. For me a straight guy pegging I a very emasculating experience. Despite it being very pleasurable. I’m not a femboy, or anything, and I am definitely on the masculine side of being a male so there was a big hill to climb for me. Shit I’m still climbing in some ways. So I would like sneak around, and steal my wife’s toys. Eventually she caught on, and it was an OMG I’ve always wanted to moment lol. She was very sly about it though. I think she understood what something like that would do to the a-typical male physiology. So she helped me find the toys, and let me progress things at my pace. That pace was something like 5 years later, and I started talking about strap ons. Anyways we had one 3 days later, she shipped the kids off to grandmas for the weekend, closed the blinds, and pranced around the house with her new found dickery slapping everything she could with it but the dog lol. Still to this day I think there is something emasculating about pegging to me despite me enjoying it, and openly so in my relationship. For example sometimes for some men getting hard with anal is difficult. Sometimes that’s physiological, but I can’t remember exactly what I read that explained why that is. For me that definitely happens sometimes, and other times I’m hard as a rock, and other times I can’t get it up, but I can tell for some reason it’s not physiological, and likely physiological. It’s weird that I can’t shut that part of me up all the time, but whateve’s I’m not stopping something that feels good because it makes me subconsciously feels less manly. My assumption about your boyfriend is exactly that, and I would recommend many other conversations with other men until you hear something that makes since based on what you know about your S.O. I could very well be way off base, but my assumption is that it’s something inside him physiologically that he’s not comfortable addressing atm. If that is the case just slow your roll towards butt stables for a while. The more you push the issue the faster he’ll run from it. Just drop the topic, and enjoy what you have now. When he’s ready he’ll start dropping hints, or outright bring up the topic. When he does then sprint to the finish line lol. In the meantime he enjoys that on a personal level so support that, and maybe recommend some toys for him, and judge his reaction. Best of luck to ya

  • @Guatch
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    11 year ago

    deleted by creator

  • @Guatch
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    11 year ago

    deleted by creator