I'm curious about pegging, how can I ask my boyfriend if I can do it to him?

Question

I've been dating this guy for a year, and a few months ago I found some sex toys in his apartment. This concerned me because I've never seen them before and didn't know if he was cheating on me or what. When I brought it up he got defensive and said they were just old toys he was gonna throw out from an ex. I mentioned that I'd seen them around in a few different places, and then he said he feels like he doesn't need to share that with anybody. I then realized that he used them in himself. I didn't think it was a big deal, no judgement from me, but we haven't talked about it since. I recently saw some more toys of his by accident and thought to myself "maybe it's something I could get into and share with him." Especially if it's something he really enjoys, then why shouldn't I help him enjoy it? Im not a big fan of MY butt being played with, I don't like anal sex myself, but he seems to really enjoy doing it to himself. I am curious now and I think pegging might be something I could have fun with, and even better if it would be a turn on for him! I just don't know how I could bring it up to him and avoid feeling awkward or making him uncomfortable. Any opinions on how I could bring up this sensitive subject with my boyfriend?
Also, any guys who like to use dildos on them self? And if your girlfriend had asked if she could do it to you would you be uncomfortable?

1inten · Accepted Answer

This may be an off limits subject for him as liking anal and being male could be seen as a homosexual trait (it isn't done well its highly erotic). Try steering some attention round back next time your both getting it on. play with his balls and put a finger on his perineum see how he reacts. try going closer to his butt if he doesn't pull away. But do respect his privacy as he may feel very uncomfortable about sharing this part of himself with anybody. If you do get to peg him don't forget that he will need to prepare beforehand. so you both have to plan it first. And in answer to your last questions. Yes and yes we have a harness

Nycterelis · Accepted Answer

Just remember that pegging and enjoying prostate milking are very very different. pegging implies submission. Prostrate milking is just enjoying different stimulation. Regardless, you should be comfortable enough to just ask. Don't be shy... ffs, he's been inside you. Can't get much closer than that ;)

bboo22 · Accepted Answer

Maybe bring up anal and just say that's something you'd possibly want to try but you're not sure since it might hurt.. And maybe ask him what are his thoughts on that and see where he takes it from there..

Jenn1991 · Accepted Answer

Just ask him. Communicate. Do some research together. Its not a gay act and can be a lot of fun for both of you.

Markm3212 · Answer

go out for a few drinks as that will lower his defences a little, then when you get home say i have a supprise for you, go to the bathroom and put on some nice underwear and the strapon and then come out and see what his reaction is.

if he has these toys for himself i am sure that after a few drinks he will be right up for it.

Hal2002 · Answer

Try asking him or better yet, bring them out during sex and see where it leads.

What is so hard about talking, why does it seem so many couples today do not have open communication. It say a lot about the state of your relationship, that you do not feel comfortable talking about intimate things.

If I was in a relationship and I could not talk about our sex life, I would not be in that relationship long.

NightOwl8801 · Answer

Just bring it up in casual conversation.

abc--123 · Answer

To be honest there's no subtle way to bring that up. You're just going to have to offer

nomadme · Answer

guys and dildos? sounds a bit weird

RSuperman21 · Answer

I wish

Chris_breaks_ankles · Answer

Smoke sum weed together then get to the chat

Anonymous · Answer

Pegging is amazing, im a 40 year old straight male, i say build up the courage to ask him, it could seriously spice things up and bring you 2 closer together, dont get frustrated if he gets scared or/and says no out of fear, be patient and tell him somethings you're interested in to let him know you're comfortable so he will relax also or try watching porn with him and tell him what turns you on.. i hope this helps dear

Anonymous · Answer

Pegging a guy is SO HOT!

Anonymous · Answer

ask him if he'd like his g spot stimulated girls don't know that our g spot, is found through our ass, so, pegging would only just feel really good to us

Anonymous · Answer

Next time you are giving him oral, reach back and start caressing his butthole. If he likes it, he will let you know. If he likes it, put some lube on your finger and give him a prostate massage. After doing that a few times, get him worked up and then ask him if you can do that with a toy.