Q. My girlfriend said she is willing to have anal sex, but neither her nor I have done it before, and I was just wanting some start up tips. I hope you can help us because I am looking forward to doing it.
Two willing anal virgins! Yippee! I am very glad you wrote, Bob, because I receive so many letters from backdoor beginners and first-timers seeking advice. You didn't specify which of you will be doing the fucking, and who will be taking it up the ass; however, I'm going to assume that you want to fuck her in the ass. (The majority of men who contact me wanting to get fucked in the ass are usually pretty specific about it.) I cannot stress enough that going slow and having patience from the start will really pay off for both of you in the end. One of the keys when trying something new is not to forget the tried and true techniques that are already working. Before you even go near her ass, get her revved up in the usual ways—her favorite oral technique, her favorite position, her favorite sex toy, etc. The more relaxed and turned on both of you are, the easier it will be. Make sure you have trimmed your nails (sharp edges suck!) and have plenty of water-based lubricant on hand—lube is an absolute must for anal penetration of any kind. Tease the outside of her ass with your fingers, your tongue, maybe a vibrator.
When she's ready for you to penetrate her, use one well-lubed finger. Instead of going straight inside, touch the pad of your finger to her opening; this trick usually relaxes the anus, allowing you to slip your finger in. Don't go too far too fast! Go up to the first knuckle and just stay there, letting her ass get used to having something inside. When she's ready for more, slip farther inside her ass slowly and gently. Make sure that she's the one in control of the action—and she should let you know if she wants more or less, slower or faster, deeper or not-so-deep.
You should set some realistic goals, because most women can't go from zero to sixty in one session. Decide to work your way up to one finger, two, or a small butt plug on your first try; that way, you won't rush things. Going too fast or trying to do too much is a surefire route to pain and discomfort, which we don't want. Practice a few times with fingers or small toys before you whip your dick out. Repeat as necessary. When you're both ready for you to put your cock in her ass, again work your way up to it, go slow, and let her guide the action. Use plenty of lube and have a blast!