Chapter 6

Hey, woody!
Are some people's butts just built differently than others? I mean on the inside. My boyfriend and I both enjoy playing bottom, but he could swallow dining room furniture with so much as a hit of poppers, and I struggle with the basic big dick. It makes me jealous that he can take so much more than me, and I think he must have some physical advantage up there. Is there anything I can do to take on more cargo?

--- Tightass

Dear Tightass:
Yes, people have different butts. I myself have three different butts scheduled this week.

You're boyfriend isn't that unusual. Lots of guys have black holes so dense even light can't escape their gravitational pull. I have a friend whose motto is "If it didn't fit, it wasn't my hole."

The rectum is not a straight tube. The pubo-rectal sling pulls the rectum in an "S" curve. The more pronounced the "S" curve the more pain you'll experience with larger objects. Your boyfriend probably has little "S" in his ass and that's why he can take everything from A to Z in it.

So how do you match your boyfriend's cavernous welcomes? Practice.

Here's how: Stick a joy toy past the anus into the rectum. Always aim for your belly button. After a few inches it'll most likely start to hurt. You've hit the curve. Pull it back a smidge then move your aim up towards the head and slide it back in slowly.

Did I mention SLOWLY? Remember, a fraction of an inch feels like a foot in your ass.

Because of the rectum's "S" curve, it's important to use a flexible dildo. As you relax more, the pubo-rectal sling elongates, lessening the curve.

Eventually, the rectum takes a left turn into the sigmoid colon. If you go that far pack a lunch because you ain't coming back.

Hey, woody!
I've always been the raging top and my boyfriend the insatiable bottom. But lately he's been bugging me to reverse our banging sessions. He wants to bury the bone for a change and I don't blame him. But here's the thing. I like my guys a little on the nelly side (I have this dominance thing, what can I say?). It's not like a purse drops out of my boyfriend's mouth when he talks but he's not exactly butch.

The thing is I don't want to be fucked by someone who isn't completely masculine. The idea of getting topped by a bottom shuts me down completely. How do I get over this? I know I'm not being fair to my boyfriend.

--- Topped out

Dear Topped:
Be honest. Sit him down, hold his hand, look him in the eye and say, "You're not butch enough to fuck me, dear."

Next Question.

You're buying into all the ugly stereotypes of receptive anal sex. You're not alone; most people do, and the reason stretches back thousands of years.

As much as man-on-man sex was accepted in ancient Greece and Rome there were strict rules about anal sex. Namely, that boys, not men, received it.

And when they did, it was something to be endured, not enjoyed. Getting fucked was a rite of passage. Once you became an adult, you were supposed to switch roles and become the penetrator. The Romans even had a word for it: vir, a man who would shtuup, but not be shtuupped.

It's hard to play the nail for years and suddenly become a hammer. Exclusively, anyway. Many boys, upon becoming men, wanted to keep getting nailed. And they were---to the cross, if society found out.

In ancient societies, nothing could be worse than acting like a woman. And nothing made you more like a woman than doing what women do in bed---receiving an erect penis between your legs.

So while Greeks and Romans celebrated man-on-man sex (or more accurately, man-on-boy sex), they only celebrated it if you were a "top." There was only scorn and social ostracism for "bottoms."

We still live out these ancient and patently false ideas of sex. You can hear it in our snide asides ("Oh, there's nothing in this town but bottoms," "He's nothing but a big bottom)."

But hear me now, girlie-man, when was the last time you heard something derogatory about people who like to penetrate. Ever heard anybody say "He's nothing but a big top?"

So call me a freak, I don't believe that "bottoms" are sissies and that getting fucked by someone less masculine makes you less masculine.

I never advise people to perform sexual acts against their will (unless it's me they're dating), but at the same time, it strikes me as unfair that you're not willing to do for your boyfriend what he's doing for you.

You've got two competing values here: Your right not to do anything you feel uncomfortable doing and your obligation to keep your partner sexually satisfied.

You can do both. Here's how: Your current interpretation is that you're going to be topped by a bottom. A better one might be, "I have the opportunity to know the man I love in an entirely new way."

Ask yourself what needs to happen to make it acceptable. Like, tell your boyfriend you have a fantasy about a leather-clad cowboy dominating you. In other words, butch him up without hurting his feelings. Now, go, get fucked.

You big nelly bottom.