Women and Anal Sex

People may be surprised to know that I wrote for a college newspaper, "Puck." The masthead for Puck read, "What fools these mortals be!" from A Midsummer Nights Dream. If you don't recall, Puck is a trickster, and jester for the King of the Fairies, Elton John. Ha! Just kidding, the Fairy King is Oberon. Puck is jerk, screwing with people left and right, although he is doing the bidding of his master, who is also a bit of a jerk. That doesn't get Puck off the hook, though. Ever since World War II, the "I was only following orders" defense just won't work.

Between 1994 and 1996, I wrote a sex advice column, like Dan Savage, except I didn't make fun of fat people like he does all the time. When writing a sex column it is wise to make a good first impression. That's good advice generally. So how do you make a good first impression in a sex advice column? Well, you have to write about anal sex, early and often. It helps to prove that you're not a prude, and that you got your freak on at some point. Albeit minor freakiness.

I'm bipolar, and people like me are get addicted to anything that makes us feel better, including sex. Methinks I've had an above average number of partners, particularly way back when I used cocaine. Sex was like saying hello at those parties. And after a breakdown, there isn't a lot to do when locked in a psychiatric ward, so there were some encounters there.

My first experience with anal sex was with an ex-girlfriend who wanted to fuck me with a strap-on dildo. The scene went like this...

Woman: Let's try something different.
Me: Like what, make homemade candles?
Woman: No, anal sex.
Me: No way. Nope. Why would I want to have sex with your bum when the greatest place in the world is inches away. Vagina trumps anus by...a lot.
Woman: I mean me in you, with my strap-on.
Me: That's not sweetening the deal, lovey.
Woman: Come on, for me.
Me: Oh, ok...sure.

Then we did it.

After I was released from the hospital with an inflatable ring to sit on, I made myself a promise. No more of that. But I did one more time, this time as the top. It wasn't fun there, either. But those experiences gave me some cred that I could use in my sex advice column for Puck. The title of that column was, That Thing You Think About: Sex-Master Advice. No kidding.

As I mentioned before, the first article had to be about anal sex, to show how open-minded and progressive I was. This is basically how my first article went:

Dear Sex-Master, My boyfriend insists that I will enjoy anal sex. I'm a virgin, and committed to remaining one until marriage (I'm afraid of it hurting). We do everything but intercourse, like blowjobs, and he goes down on me. Recently, he talked me into anal sex. It hurt like hell, and there was even a little blood. Why do men enjoy this? Is it me? Thanks in advance for the advice. Signed, Redbum.

Dear Redbum, Your boyfriend doesn't need to play with your asshole, since he is an asshole himself. Many men push for anal sex with their girlfriends, and insist that they are not gay. But avoiding a lovely, moist vagina to get to a tight, dry anus indicates to me that he'd be happier with a Friend of Dorothy. You've decided to avoid intercourse until marriage. Anal sex without a condom is dangerous, and he needs to back off if you don't want to have it. You mention that you're afraid of vaginal sex, that it will hurt and bleed when the hymen is broken. In my experience, this was never very painful for my partners. And friends of mine say it's not bad. However, to help allay your fears, try spreading your legs wide open and feeling inside for the hymen, which can be small and partially attached. You may not even have one, as it is often lost in childhood during play, like falling off a bike or on your bum. A detached hymen is even possible from just riding a bike or horse. Hymens come in all shapes and sizes, so get to know your little gatekeeper. In rare cases, the hymen can be removed by a gynecologist if it is large and firmly attached. Most of the time, though, the erect penis will hit the hymen, tear it, and give you a bit of a jolt and maybe a little blood, but that's it. A friend of mine was so concerned about this that she used her dildo to crack her maidenhead, as it were. Nothing wrong with that! I hope you've found this helpful, my friend. And never let a man pressure you into anything you are not comfortable with. That's a sign of big trouble. And always use a condom.

That was my advice. One of the first articles I'd ever written! I'm so proud. Every so often, I'll dig another article up from Puck and post it. I think the advice I gave was sound.