Thread: How to approach pegging fantasy?

I've been having fantasies about pegging my fiance lately, but I'm hesitant to bring them up with him and could use some advice. In our otherwise open relationship, "kinky" sex doesn't get much talk time, and he often has a joking attitude that makes it hard to evaluate whether a sexual suggestion was meant to be serious or sarcastic/gross. (for instance, he mentions urinating on me, but I'm not sure how much of it is him dropping hints of a fantasy, vs. him trying to gross me out).

Here's the rundown: My fiance was completely shy about anything 'back there' when we started going out, although he's been on the giving end of anal quite a bit, especially since I've started to enjoy it more. When we first met he wasn't used to communicating openly about sex and I was too shy, so we've slowly been building up to conversations both in and out of the bedroom.

We've been together for almost 7 years, and in that time we've experimented a bit but he seems content to stick to vanilla sex most of the time. The first year we did some exploring (mostly rimming during play) but that was it. For about a year after that we did nothing, then he seemed interested in it again and since then he's very slowly opened up to having fingers and toys inserted - but only when he initiates. I know he likes it and am eager to go a little further, but I don't want to force him past his comfort zone. As for me, I'm very shy outside the bedroom, so getting up the courage to dominate him would be something new and while it's exciting to think about, I'd be really hurt and embarrassed if it didn't work out.

One side effect of him not wanting to discuss his anal pleasure (he'll talk about mine!) is that I don't know what kinds of toys he'd like, and all of mine were definitely designed for women. I'm on the lookout for more to add to our collection, including a beginner anal set and a harness with an attachment that he might enjoy, but I'm not sure whether I want to keep it a secret and surprise him, or try to talk about it and bring him along on shopping trips.

I don't think my fiance would think of pegging in terms of being gay, but rather in terms of submission. He has a very dominant personality, and doesn't like losing control. Because of this, all the anal play we've done has been initiated by him, so that he always has control of what I'm doing. I want to let him take it slow and continue to let him initiate new kinds of play... but it's frustrating not knowing if I should say something, or wait for him to build up to it himself. The pegging thread was a good read, but didn't give me much information on how to approach the subject. Any advice?

Hmm. Well, I'm trying to think how I would do this, (and possibly would someday)... I guess I would just start with some of the toys that he uses on you, something simple to start. While you guys are into it, grab something and say "here, let me try this on you" just kind of casually and then go with it and see how he reacts.
Either that or casually bring it up when you say how good it feels for you, "hey, I bet that would feel good for you too" and see how he takes it.
I wouldn't try to get in a long drawn out conversation about it though. I don't think that most straight guys want to admit how much they enjoy anal stimulation.

Perhaps next time he initiates something in this direction, and if you're using a toy on him make a comment about how it would be easier if you had a strap on. Just gauge his reaction and take it from there. If it's positive maybe you can shop together (online is less threatening than a 'real' shop). If you're worried about him feeling submissive, just ask him what he wants you to do and let him take the lead.

If his reaction is negative in any way, you'll just have to make do with the way you do things already.

The fact that you're debating whether to surprise him or not is your answer.

I also agree that most guys won't admit to being either interested in experimenting this way or admitting that they like it - and many, many more like it than will ever say. They don't know what they're missing

This is helpful, thanks! I'll try bringing it up next time we're playing around, just as a casual suggestion.

Well my girlfriend took a risky approach I would say. I wasnt open about the idea of back there at all because I did not know what I was missing and I knew eventually poo might enter the equation.
She is very strong for a girl, actually for a guy too and is a 2nd dan in Jiu Jitsu. She secured me and used her finger on me. It felt interesting and different. I dont know about involving a strap on, but I am more open to the idea now.
However I guess other guys might freak being rendered helpless like that.

I started slowly with my lover--first just using fingers (and he responded well to that), and then I asked him if I could use a ribbed-type plug.

We did that (he's the type who will try anything once), and he loved it while it was happening, but afterwards, he said he prefers my fingers. For some men, I'm guessing anything larger just doesn't feel as good. At times, he told me there was just too much sensation going on for him to concentrate on anything except the anal aspect.

So I will respect that and leave the toys out of it (although I enjoyed using the toy because I thought he would enjoy it, too). I just want to make him feel as good as possible and let him decide the comfort level.

I guess what I'm saying is your fiance may or may not enjoy anything larger~~I would probably not surprise someone (and spend a lot of money!) on something I'm not sure they would even enjoy~~

If all else fails, set your browser to save your last surfing session and shut it down with strap on related sites open