Other helpful discussions on Pegging:

What is pegging?
I was reading a review and saw this get mentioned. I have never heard of it before so was wondering what it is. Hope this is under the right category.

Which toy for pegging beginners?
My hubby and I are having a hard time finding the perfect toy for pegging! We are looking for: - The dildo itself doesn't have to be realistic but it

Has your participation in pegging changed how you view yourself over time?
I got to thinking about prostate stimulation, and how as I have progressed in playing over the years I have become much more comfortable with...

The Adventurous Couple's Guide
So we've both done some general reading on pegging and tried it ourselves a few times, but I'm curious: have other people used and found the...

ATTN Peggers!
This one is for the Ladies who Peg and those who want to. What is it about pegging that drives you to do it or want to give it a shot. Is it the power

I'm not sure the best way to bring it up. I know my lover started by asking me to use my vibrator on his perineum. Then one day, he told me he wouldn't mind if I played with his ass. I was absolutely delighted about it. Later he confessed that he sometimes fingered himself while he masturbated. If he'd told me that to begin with, we might have gotten to the good stuff sooner, rather than me going slow so I wouldn't scare him out of it.

Few questions to ask yourself first:

What's her attitude on sex in general? If she's uncomfortable with hand play and/or oral she's probably not ready to consider pegging.

What's her attitude towards anal play? If she thinks it's dirty, gross, immoral, whatever you'll need to do some groundwork there. If she's OK with it then start with that, move on to toys, then, eventually, bring up the harness idea.

The one blanket advice I can give is don't just toss her a harness and say "put this on" as you bend over. Too much too fast.

I think Nina Hartley has a few good hints in one of her more recent articles:

link

A little tact is a very good thing, but it also helps not to beat around the question too much try just asking what she thinks of anal then role reversal and if she is cool with both then you are good to go

also have confidence when you ask if you are apprehensive then she will be too and if she seems hesitant or just the type that needs a little more explaining then explain the idea of prostate stimulation and even sit down and do some research with her biggest thing is you both need to be comfortable with talking about it before you can really get into doing it.

I agree with PapaCass that you need to be pretty direct. It's tempting to try to ask like it's a bit of a joke so you can cover your embarrassment if they say no. But if you think about it why would your partner give you a sincere yes if they fear you are only joking - then they are in the embarrassing position if it turns out you really are joking. Safer by far for them to say no so they probably will.

Also, I think women are rather more attracted to us if we are prepared to vulnerable to them. I was amazed how readily my wife accepted the idea of pegging. Luckily she is a doctor so I didn't need to draw any diagrams as to why it might feel good for me. However, if you aren't in that happy position I think its well worth arming yourself with some web links to discussions of prostate stimulation.

I guess it's a bit easier than it was 13 years ago when I asked as pegging (it didn't have a common name back then) is a bit more main-stream and you would have to be living under a rock somewhere not to have come across some passing reference to it in the media. Also there are endless online stores selling the 'equipment' with advertising clearly aimed at the hetero couple. At least in these regards your partner has less reason to assume you have gone totally mad.

Well, we did go from no anal play to pegging but I most certainly didn't buy the equipment and present it as a fait accompli. In the case of my wife who is rather practical and down to earth she wouldn't see the point of a bit of minor anal play but she certainly understood why prostate massage would be stimulating. So I guess it depends on your partner but at least for some being clear about where you are planning on going works best.