For 18 years or older?

Get a dildo that is smaller than your penis and use it on each other. And if that doesn't work then don't do it. Sometimes somethings are not meant to be.

Well, since gay men do participate more often than not in anal sex you could seek help from the gay community. It is not something that some people can do quickly. It takes time to learn how to relax the sphincter muscles. Most people are not aware that humans have TWO sphincters. The first one is near the opening of the anus, and then the second one is farther up. My best advice would be for her to start with a small toy/dildo and then work her way up to bigger sizes. Also, the position can make a big differences. If you lie on your back and let her control the entry by straddling you, she has control on how far the entry goes. The hardest position for most gay men is the missionary position, just due to how the body is conformed. Lube is necessary, but numbing lube is not necessarily helpful. In the end, no pun intended, she needs to learn to relax those muscles, but once she does gain this skill, it may still be something she just isn't able to do. In the gay community, many identify themselves as either a giver or a receiver, many "givers" do not flip-flop, it is too painful for them. Make sure you go VERY SLOW, let her determine how far things go, until she relaxes and gets used to this new experience, she needs to have the control. Good luck!

you could try sticking a candle stick holder in her first then put your penis it will get her used to it get her to wake up and smell the roses then feel free to anally penetrate her anytime try the snuggies they keep you warm while doing it!

Also your dick must not be that big to hurt her if you asked this on yahoo for random strangers to help why your sex is not working

Thanks,

Leah

Id say the best thing is to let her masterbate and try it on her own with toys and let her get comfortable with that before moving onto both of you trying

try using ur fingers first then go in slowly.. it is gonna hurt but u gotta break it in and she will feel wierd the nest day.. like she has air in her behind but thats about it.. it will go away in like a day

Why don't you get her to penetrate you with a dildo so you know what it feels like.