I want my wife to peg me, but how do I ask for it without freaking her out?

I really do not know. My wife never freaks out no matter what I ask her to do. She may call me crazy but never freaks out. The first time she used a strap on with me was about 39 years ago. We had been using butt plugs as part of our BDSM games and doing anal sex. I bought a strap on for her and told her that we both should feel what it is like to be on the other end of the stick, so to speak. We did it a few times, as did her girlfriend, but they never got into it even though I liked it. Butt plugs and dildos were OK but I ended up tearing my colon and needed surgery to repair it. If you do it, start off with a small one and work your way up. I just bought large ones and perhaps that was not a wise move in retrospect.

 

I would think a reasonable strategy , why playing with your bottom makes you gay I don't know .

I assume her bottom is sensitive as I assume all bottoms are . So if you play with her nipples does that make her a lesbian ?

Xx Wendy

 

My wife thinks its a gay thing, Im just going to keep dropping hints and eventually she will agree to us buying a strapon I hope.

 

For me it was easy. After having anal sex with my wife, she was more than eager to show me how it feels. We did it for a few years until one day it tore my colon and I had to get surgery. After that, no more pegging for me.

 

As you've mentioned a possible aversion to toys..I offer the following advice.
Does part of your sexual relationship with her include rimming? Either you to her or vice versa? It can be a way to discover her openness or otherwise to taking things further.
Is she willing/wanting to try say inserting her finger? Offer her gloves and lube, thank and praise her for any small step she is willing to take.

 

My wife has never been shy about anal play. However, after we got a clone-a-willy kit and she made a dildo that is an exact copy of my penis, she got into the idea of fucking me with my own cock. She really likes using it on me. I like how it feels too.

 

We started slow....as I explored her interests (which included anal) over time (a year or so) I encouraged her to touch me there more and more frequently. I've always had a "hot" bottom so she wasn't too shocked (obviously given my avatar we've evolved). Her realizing (with hints dropped and reading etc) that milking my prostate was so pleasurable to me, over time she really got into it as a means to get me hot and bothered. Now, it is a standard part of our sex/tease sessions, and is a wonderful way for her to get me so worked up I can't see straight. RE toys...she is about the same as yours, not a huge fan. But, with time, we found the feeldoe and other products to not get in the way and make it very pleasurable.

In the end (no pun) I think it is the guy who can have the biggest hangup, and this can carry over to the woman with a sense of unease/fear over homosexuality/etc. and spoil the event. Sex is not black and white, and should be consensual and open....but breaking down the barriers takes time, communication, and a willingness to open up. To be honest, that is what makes it so exciting...that thrum of your heart the first time she wakes you up, with a strapon rubbing your ass and telling you she's going to fuck you silly...it is SO worth the effort. Have patience, and good luck.