Guys who like pegging: What are some ways to convince a guy to let a girl use a strap-on on him if he seems hesitant?

He said he'd let me rim him once in a while, and "possibly" give him a prostate massage, but he says things going into his butt really seems "too freaky" to him. I'm trying to tell him that these things can be pleasurable, but I'm not sure if I'll convince him. We both want to try anal (him doing me), and I know that not letting him do me until I do him is an option, but I feel like I'd be punishing myself for no reason if I do that. Thoughts? Suggestions?
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Most Helpful Guys

  • Perhaps you could peer deeper into the male psyche and empathize a bit more with your partner. But who knows, things raising eyebrows in an abundant majority of males today might become commonplace in 50 or so years. You are in the vanguard, though, and willing to do old things in new and creative ways. For the past few millennia the females have been on the receiving end and males in the opposite direction. After such glacial time certain behaviors, especially sexual, could have gained a genetic basis.

    Now speaking from your side of the matter, you could decide that he cannot do this sexual prank without your first doing him. I think that would resolve the situation and you'd see how far he is willing to go to please you. This might be a true test of character for all your future bedmates.

    Your fascinating question reaches far beyond my personal experience. However, you are a very hip woman ready to explore new avenues of thinking and being and I congratulate you for it.

    • I've already considered telling him to let me do it to him first, but since I already would like him to do it to me, I feel like it could be punishing me if he doesn't want to let me. But since we both want him to do it

    • ...to me already, who knows if that would work. Thanks for answering!

  • How about rimming him and giving him prostate massages for a while first? Have you ever actually given him either of these? If you want to receive anal sex then you have to do this before he would consider receiving it when he has reservations.

    Be quiet about the strap on for a while, give him a few rim jobs and massages and then after a while maybe reintroduce the strap on idea through a p*rno or something like that. Or maybe when he's on his back, moaning with your fingers in his ass massaging his prostate gently hint that a dildo may also feel just as good too...

    My advice would be to learn how to give prostate massages well. Maybe even buy one of those little toys. Done properly they can be very pleasurable (I know this from personal experience).

Most Helpful Girls

  • There is nothing that you can really do to convince him. If he isn't comfortable with it then you shouldn't force it on him. To do so would be disrespectful and would show that you don't respect his discussions and his boundaries.
    You can try by introducing anal play (fingering and rimming) and let him penetrate you and he may in time become more comfortable with the idea. On the other hand he may not and you should just leave it and accept that that's one boundary you will have to respect if you are going to be together.

  • Blow jobs with fingers and toys. My guy loves it so I don't know what else to say. My guy gets multiple orgasms some times, you could tell him that.

    • How did you go?

    • You get to use a strapon yet?

    • Nope. Haven't even been able to get a boyfriend yet.

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  • Don't push a guy into taking anal. It's practically the same as him pestering you to have sex when you don't want to. If you were really persistent and he consented (or complied) but didn't want to, then it would actually be a bit rapey

    • I agree, you shouldn't force him into doing things he isn't comfortable with.

  • You have to talk to him in depth about pegging; explaining everything that goes on; then start with a finger; when he is comfortable, move to a small but plug; as he gets used to each thing you use, get a little bigger; till he is comfortable taking a very slender dildo that is about 3 inches up his anus. The key to having him take a full size dildo up his anus, or a bigger one; is conversation. If you need more guidance, look up Dr. Doe on YouTube, she has a channel called Sexplanations. She covers this well.

  • I don't know about the rest of you but it sounds pretty gay to be honest.

    • How? It's not gay if he's doing it with a woman and only wants to do it with a woman.

    • Its still messed up regardless.

  • I don't know, but maybe a relaxed atmosphere will help him get in the mood. I guess it might be that he genuinely does not like it, which in that case it would be very difficult to change, or otherwise it might be that he has some idea block which you need to remove from his mind. For example he might think he is gay if he does that.

  • Have. Him explore his butt first with gloves lube and his finger. Then use toys. You have to train it to relax