Tony,

I’m trying to get my girlfriend into anal. Neither of us has ever done it before,… Tony,

I’m trying to get my girlfriend into anal. Neither of us has ever done it before, but we haven’t talked about it either. I don’t want to scare her off. What should I do?

Backdoor Man

Now, what you want to do is start kinda sneaky. Nah, I’m not telling you do the old “Oops, I guess I just missed” and hope she won’t notice; that’s about the dumbest thing you can do. Just slowly introduce her to the idea. When you’re hitting it from behind, and she’s getting off, throw in some very sensitive manual stimulation, and go slowly. The old shocker works best when it isn’t too shocking.

Take a lesson from Ivan Pavlov and introduce some conditioned stimuli to get the conditioned response (pleasure). Do this during a few different sessions, going slowly and backing off if you feel any clenching.

Then you can bring it up in conversation.

This is about patience, man. First off, for good reason, most women just aren’t going to give up that last bastion of virginity, especially when it’s not inherently pleasurable to do so.

Regardless, there’s a good reason to communicate first: preparation. In my limited experience, I’ve been lucky and dodged the bullet so far, but a lot of trauma can be avoided with an enema. If you’re big, there’s a good chance it just isn’t going to work out, no matter how much lube you use.

Still, lubrication, and lots of it, is vital. Mother Nature just isn’t going to cut it. Be respectful of your woman and pay attention to her. Don’t be stupid, either; if she’s willing to do this, you have to accept that anal is a little bit dirtier than other types of sex.

Ultimately, both partners need to be calm and trusting. If she’s nervous, it’ll be like trying to have sex with a brick wall. Don’t force anything. If she’s not going for it at all, respect that. If she is, just go slow, use lube by the gallon, and do the exact opposite of everything you ever saw in porn.

Dear Tony,

Two weeks ago I had a three-way with my boyfriend and my best friend. She’s really sexy. We’d talked about it before, and we were all drunk, and I did not know what was going on. How could they have taken advantage? We haven’t done it since, but both of them have talked to me about doing it again. I had a lot of fun, but I don’t like where this is going. My boyfriend’s talking about my friend a lot, even after I asked him not to. What should I do?

How could they have slept together? You should know; you were there.

Now for a rant. Yeah, the signs in the counseling center are right. Alcohol can lead to loss of judgment. But come on, sweetheart. I’ve nearly killed myself drinking countless times, and I’ve never “not known what was going on,” especially with a “sexy” friend I’d talked about having a “lot of fun” with.

So, did you feel taken advantage of from the beginning, or was it not until your boyfriend started talking about your best friend that you got upset? Take some responsibility, and don’t act like a victim. There are real victims out there, and it’s an insult to them to even hint that this was date rape. If you really do feel taken advantage of, talk to someone (again, the counseling center). And leave alcohol alone.

You are kind of screwed, though. The boy’s still begging after a couple of weeks of nos. Actually, that’s a good sign. It means he hasn’t slept with the best friend again yet, which is only a matter of time. Either accept an open relationship or pick a side now, before both relationships are dead.

I’d side with the friend. And learn a lesson.

E-mail Tony and Liz at [email protected].