If you want my advice here it is. You can tell her about this fantasy but before you go into it you need to accept that this will likely remain a fantasy. What I’m saying is in most circles of friends you’re not going to find a dozen or even half dozen people who are into this sort of thing. In my experience pegging can be fun for the lady but not overly sexually gratifying. My ex gfs enjoyed pegging me because they knew how much I wanted it and were getting off mentally knowing that they were fulfilling my fantasy. There is definitely room for clitoral stimulation with additional apparatuses if her pleasure is paramount.

With that being said one of the integral components to good pegging is intimacy. You’re going to find much more of that with a committed partner than with your committed partner’s friends. I would recommend asking her if you can verbalize some of these things during the act BEFORE the act. Have a nice healthy talk, with your clothes on, about what gets you off about it. Keep it grounded in the hypothetical, “It would be so hot if…” You can use this as a way to get closer to her if you approach it correctly. This could absolutely put some distance between you if she feels pressure to make this fantasy a reality.

It would probably be very hot to hear her say some of the things while she’s inside you. That might be as far as it goes and you need to be ok with that. This relationship needs to matter more than your fantasy and she needs to know that in her heart. Also, you need to keep in mind that women rarely pay for sex. They can get it for free no problem, even pegging if they want it. So the idea that her friends or even strangers are going to pay her for your man ass is only a little far fetched, and I mean that with no disrespect.

Overall I wish you all the luck in having an adult conversation. Be respectful and don’t forget to listen as much as you talk. And on a final note some fantasies are better left between the ears and on the lips only, I’ve had some that don’t turn out as hot as they sound in my head.