DEAR ANDREA: I love putting fingers, dildos, and other fun toys up my boyfriends' butts. I love showing a straight boy the joys of being on the receiving end. I've just started a new relationship with a rather inexperienced boy. I tried to stick my finger up his ass during a blow job, and he totally freaked out. I had to play it off as an accident ("my hand slipped"). How do I break him in?

Love,

Cheeky Lass

Dear Lass:

While your little fib may have mollified him at the time, things very rarely just "slip in," as I'm sure you know. That guy who's always showing up in the E.R. late at night with a lightbulb or a kosher salami up his butt inevitably tries the same approach: "I must have sat on it, Doc," he'll explain, "and it just slipped in."

You will have to be more up-front about your plans for your boy's backside. The sudden, utterly unexpected introduction of a digit to the fundament is enough to freak almost anyone out. Sit him down (move the salami first) and tell him what you'd like to do and why. I'm assuming it isn't just the rush you get out of showing those straight boys how to take it like a man – surely there's some pleasure for him in your plans, too.

Right?

Anal penetration and prostate stimulation can be intensely pleasurable, but there's no guarantee that they will be for any individual guy. Pure sensation aside, challenging the societal strictures against anal anything (it's dirty, it's "gay") can be just too much for some folks. Talk it out, and then, if he's agreeable, start again with a lubed-up finger and a lot of warning. He probably won't freak out again if he knows what's coming, but don't take it personally if he isn't into it. And one more hint: your choice of words sounds pretty hot to me and (I assume) to you, but I wouldn't let on that you're hoping to "break him in" if I were you.

Love, Andrea

Dear Andrea:

Every time my girlfriend and I are together it's great, but something new has entered the picture. We have approached anal sex very closely. I have experienced this once before. She enjoys the foreplay but has fears of problems arising from that type of sex and moral questions as well! What do you advise?

Love, What Next?

Dear Next:

For the health and how-to questions, get a book (Anal Pleasure and Health, by Jack Morin, or The Ultimate Guide to Anal Sex for Women, by Tristan Taormino). Proceed carefully, giving her plenty of time to work through her anxieties and get used to new sensations.

For moral instruction, with which I cannot help you, consult your clergyperson. On second thought – don't.

Love, Andrea

Dear Andrea: I am new to asking questions, so please don't shoot me out of the water.

A friend and I were discussing anal sex among gay men. He says that it's painful and that anyone who would be into it must be into painful sex. I said no way – the only way anyone would do anal sex is if it were pleasurable. So:

1. Is it painful or not?

2. Does penal size have anything to do with it?

Love, Who's Right?

Dear Who: You are, sort of; it shouldn't hurt. Anything rough enough to produce pain is probably producing damage, and the people who get off on rectal bleeding or peritonitis are rare, and I don't want to meet them.

So why didn't I declare you the undisputed winner? Because the uncomfortable truth is that it often does hurt, and yet many people keep plugging away at it anyway. Why? Because it also feels good. I could go on about how lube and time and good communication will ensure that it doesn't hurt. I often do go on exactly that way. People should do as I say, too, but sometimes they don't.

I intended to take your opening plea seriously and not make fun of you, but then you went and asked about "penal size." I'd like to tell you that the size or population density of a prison has no correlation at all to the amount of painful anal intercourse taking place therein, but I'm not sure it's true.

Love, Andrea