1) Pegging by no means has to be a FemDom type of thing, and can in fact be very sensual. It’s your fantasy baby, you can have it any way that you like! Also a piece of advice that I give to every pegging virgin is that you should bring your own strap on so that you can start with a size that you are comfortable with instead of hoping the lady you find has the right fit for you. If you do this however, it needs to be brand new in the package for most girls to feel comfortable using it. So take a trip to your local adult store and get what you think is good for you!
2) lol Well I would highly suggest grooming prior to coming here, rug burn in that area can be quite uncomfortable.. The best thing to do while uncomfortable, and perhaps a bit embarrassing, would be to go get a wax. It will suck but hey sometimes you got to take one for the team lol, and assuming you don’t have a really, really good friend that will be willing to shave you back there, it’s probably going to be your only option, lol.
3) If it is something that interests you then yes you should tell the lady in the bar what you are looking for. As Alex stated no one is going to act disgusted with you for wanting it, this is a very common things here, and if the lady isn’t willing to provide it then she will let the other girls know what you are looking for so that you can find the right girl quicker. We are very professional women that truly care about you having a great experience, if I can’t give it to you, I will find someone who will, and so on. If you wait until negotiations and she isn’t willing to provide pegging well then you’ve just wasted both of your time for no good reason, it will make it much easier for you to just be up front right away!