My girlfriend adamantly refuses to take it in the butt. She claims that rear entrance will damage her in some way, i.e., stretch the sphincter to the point where it will not regain its original structure. Dr. Drew (of MTV’s Loveline) says anal sex is something to avoid. Can you shed some light on the subject? I have done this once before and know to be gentle and slow. Please try to reassure my girlfriend that she will not be damaged. —Steven

Why don’t you try being a bottom for once to see how your girlfriend would feel?

I can’t assure anyone that anal sex is safe. Unless you’ve been living under a rock, you should know that AIDS is frequently transmitted through unprotected anal sex because the tissues surrounding the anus are easily torn. However, I have heard that if it’s done properly, with lots of lubrication, there shouldn’t be any damage, and it can be intensely pleasurable for both partners. A book you might want to consult is The Ultimate Guide to Anal Sex for Women by Tristan Taormino.

Since anal sex is forbidden fruit to many people, I interviewed several others on the topic.—Cherry

“I think anal sex could be great. But I’d want to work up to it with smaller (and more controllable) things first with plenty of lubricant. Right now it’s a scary prospect, and a little gross . . . it would definitely make me feel vulnerable. Anal sex wouldn’t be my first choice, but I think I’d be willing to at least try it and do it on occasion with other activities during those wild hours of I-have-to-have-more sex.”—Nicole, 27

“I like the sense of taboo and the heightening of the erotic thrill. The edge of dominance in the position and attitude, and the knowledge that I could be entered the same way, is cool, too. My girlfriend has really enjoyed it when I put my mouth on her anus. Licking a woman’s ass is wonderful, and I have found it universally enjoyed by women (the spiral descent toward and into the anus becomes a ramp up the scale to a big fat orgasm). Ass fucking should be taken VERY gently, as it can be intense and a bit dangerous. The best experience I had was in a field in a remote woodland area. An ice storm started, and there were all these little hail stones pounding on us as we had anal sex on our knees in the mud. Whoa . . . that was really good! Kinda spooky!”—Danny, 45

“I think being a top is just about screwing or getting off. Stick it in, take it out; there’s not much to it. Being a bottom puts you in a more vulnerable position, but you can experience a lot more. You’re in a less selfish position: You’re receiving, so you can please the other person, just like a woman often receives whether she’s into it or not. If you’re a guy receiving, you can DOUBLE the pleasure—that is, you can stroke your penis while your prostrate’s getting massaged.”—Mark, 25

“Oh, great! My favorite subject. I think that men are still very much in the closet about bisexuality. That it is OK to do it to a woman but not to a man is an interesting issue for ‘straight’ men. Almost every man I have been with has asked me to have anal sex. My husband and I have actually had arguments about it. I told him, “Fine, I’ll get a 10-inch dildo and we’ll let you go first.” That tends to shut him up on the subject. I have done it twice and it wasn’t all that pleasurable for me. The first encounter was with a boyfriend who was not all that well hung. So that time it didn’t hurt, but I felt kind of demoralized, like I was a dog or something. The second time was with my husband, who has a big penis, and it hurt.

“If you ask guys why they want to do it so much, most do not have a valid answer. And don’t give me that I-just-want-to-love-you-in-every-way-possible BULLSHIT. You just want to have control of my body and see what it is like to have sex like you are homosexual, but not really doing it.

“I will never do it again.”—Amanda, 38