My boyfriend and I have been going out for nearly four months now and are sexually active. He keeps saying that he'd like to try anal sex but I get the bad feeling that he means he'd find sticking it in my ass easier than in the usual place. I told him to rein back a bit and even sent him the 'anal sex lowdown' article on this site, which I'm still not sure he's actually read.

The thing is, I'd quite like to try fingering him, too, but he's straight almost to the point of homophobia. I know he's not actually, though, because one of his best friends has been going steady with his boyfriend for almost a year now - and practically tucks his tail between his legs (not literally) whenever I mention it. How do I convince him that it could be as good for him, if not better, than for me, without freaking the poor kid out further?

Dear AnansiGirl,

I got a chuckle from your question. One of the first illustrations I had done for the anal sex chapter in my book is of a woman fingering a guy's rear end. The reason is because I wanted to help break the stereotype that anal sex means 'a guy's penis up a girl's bum.'

If anal sex is "done right"--and by that I mean with plenty of lube, lots of practice for weeks beforehand, and NO PAIN--it usually requires a great deal of trust and communication between the partners. It's not something you do when your relationship is new or if you aren't able to totally relax with your partner. Total relaxation and preparation are essential, and you should never do it when you've been drinking or smoking. You need to be fully aware of the sensations in your body, since any feelings of pain are an important indicator that something isn't right.

I'd also like to add that if getting a penis inside of your body is how you define sex, then your rear end has nothing on your vagina. A penis tends to feel a lot better in a vagina than in an anus, and it smells a lot better when you pull it out.

As for exploring his rear end with your finger, I fully agree that it might be an interesting experience for the both of you. Just feeling his prostate gland might be seriously fascinating for you, although it's not the kind of thing you'd want to write a paper on for your biology class. Also, I'm willing to bet there are plenty of straight guys who would enjoy it if their female partner mixed it up with a bit of butt play, but it's not the kind of thing they'd go telling their buds about: "Gawd, I so love it when Amber sticks her finger up my butt!"

You might try a bit of the old "you can try mine if I can try yours" line. That, and a lot of reassurance about what a total guy he is!

Best wishes,

Paul
author of "Guide To Getting It On!"

if you are interested in Paul's book:
http://www.amazon.com/exec/obidos/ASIN/1885535694/goofyfootpres