Okay Buster, I'll try to help. First you need to take your time. Get her and yourself relaxed and don't be in a hurry. Get a good quality anal lube at your nearest adult store or use KY jelly and rub it on the outside of the anus, slowly working one finger into her rectum. After she gets used to the feeling of something being in her ass you can slowly work another lubed up finger into her to stretch the hole further. Now, by the stretching her hole I don't mean that you are making it larger than it ever has been, it's that the hole has always been used to pass body waste one way from her body and that waste usually doesn't spend a lot of time coming out. Once you manage to get two fingers in and this might take a couple of sessions over a couple of days to accomplish, you should have her pucker used to the approximate width of your tool. Slowly, and I mean slowly, work your tool into her ass. Once it's in there, just rest for a time to let her get used to it. Believe me, once she does get used to something being in her ass, you can pound the hell out it and she will have one of the hardest orgasms she has ever had. Be warned....once in a while, when you are finished and pull your tool back out, it might have a little "stuff" on it. If you think you can't handle it, don't go there. Consider where you're putting your dick. Yes, it's happened to me and I don't care...it washes off. Just comfort your girl and tell her it is okay because she will be embarrissed. BTW, you will being "pumping" a good bit of air into her during this....make sure that she fights the urge to pass a little gas until she is safely in the bathroom, otherwise it might be messy. Have a good time with man, it's awesome!!!