OrdinaryGirl

Well...provided you convince her to try it, she will have to let you know when it's a good day for it. If she is feeling at all irritated in that area before you even start, that will be the last time she will give it a go.

Because she is nervous about it and worried about pain, it is going to be harder for her to relax. My suggestion is to take it in steps. During spooning sex, just rub the head up and down her crack a few times until she is totally comfortable with that. Then the next few times just rub the head against the entrance but don't push hard and let her get used to that. Once she can relax, she will find that even that much stimulation can be a turn on and taking the next step will be much easier.

Ordinarily I wouldn't suggest the things that wudluv has mentioned, simply because I do believe that if the girl is turned on and the guy uses the right technique, it can be an incredibly pleasurable experience for her, too. However, since she is concerned with pain, I think that any discomfort will cause her to ask you stop, before she really gives it a chance. Therefore, anything that numbs that discomfort will probably go a long way to getting her to incorporate it as an occasional part of your sex life.

And as for triggering a bout of hemorrhoids, if you're gentle and go slow with lots of lube, it should be fine.