Stepping to the Rear: Backdoor Basics - OZY | A Modern Media Company

Stepping to the Rear: Backdoor Basics

Stepping to the Rear: Backdoor Basics

By Eugene S. Robinson



Because sexy is as sexy does.

By Eugene S. Robinson

You have sexy questions? Eugene has sexy answers. Write. Now:

Your Anal Primer 

EUGENE, SIR: I was just reading your response to the letter from Jordan Barbeau (“Anal Adversaries”). What I’ve written below is based solely on my personal experience as a woman who engaged regularly in anal sex at some point in her past. There may be nothing new under the sun, but once in a while, there may be something you just haven’t heard before.

First of all, let me say that I was very fortunate to love a man whose favorite phrase was “Would you be interested in …?” and who always let it go if I said that I wasn’t interested in whatever he was suggesting. In any case, almost 30 years ago, he and I decided to try anal sex because we were both experimentalists and believed that you can’t have a valid opinion about something unless you’ve tried it. We always used a condom because the flora and fauna that belong in the digestive tract DO NOT BELONG in the urinary tract, and he didn’t want to accidentally get some horrific infection in his penis. We also always used a lot of lubricant because the anus is like a one-way valve that evolved to discharge certain things, but was never designed to voluntarily admit anything going in the wrong direction and certainly not something as large as an erect penis.

We tried three different anal entry positions.

Position 1: From behind, with me on my hands and knees.

Results: It was boring and did not result in any pleasure for me. It was not painful in any way either, so I would not counsel against this position.

Position 2: Also from behind, but with me lying facedown.

Results: It changed the angle of entry and was extremely painful, as in PAINFUL! It was not quite as painful once the penis was fully inserted, but the pain never stopped. I also experienced some tearing and bleeding even though we took things very slowly and used lots of lubrication. The next day, I woke up with hemorrhoids, which lasted three or four days and which were even more painful than the anal sex had been. I would counsel avoiding Position 2 under all circumstances.

Position 3: The traditional missionary position, with me flat on my back, my knees pulled up as high as possible. The only change from traditional sex was the insertion of the penis into my anus instead of into my vagina.

Results: Mind-blowing! It was addictive. First of all, there was no pain — none. Apparently, the angle of entry makes all the difference. And then there was the pleasure, the mind-blowing pleasure. Having sex face to face but with his penis in my anal cavity sandwiched my clitoris between us in a way that caused incredibly strong and pleasurable clitoral stimulation. The presence of his penis in my anal cavity combined with the weight of his body on top of mine simultaneously stimulated my G-spot, and stimulated it much more strongly than I had ever experienced during vaginal sex.

Imagine having two orgasms at the same time, and then imagine that each one is at least twice as intense as what you normally experience: That is what Position 3 was like for me.

It was so intensely pleasurable that it was almost painful. When it was over, I felt as if I were an electric circuit that had experienced such a strong power surge that it had tripped my circuit breaker and I couldn’t function anymore. I literally couldn’t move. Every nerve and muscle in my body was so relaxed that I couldn’t even lift my hand or twitch my fingers, let alone roll over or sit up.

Position 3 anal sex was so much more pleasurable than vaginal sex that I personally would never waste my time having vaginal sex again unless I wanted to get pregnant. And after my first experience with it, it was consistently my choice of activity every time it was my turn to choose what type of sex we had. I cannot imagine that there is any drug in existence that could make me feel as much pleasure as having anal sex in Position 3 did. A potential bonus, at least from a man’s point of view, was that Position 3 was quick! It was so intensely stimulating to all my lady bits that it became a game between us to see how long I could hold out before I couldn’t help but orgasm. No wonder I was addicted to it.

So, that’s what I can tell you about anal sex from a woman’s point of view. I hope it is in some way interesting, enlightening and/or new. — RM

Dear Regional Management: Thanks for sharing your rectal remembrances!

Peg of My Heart?

EUGENE, SIR: I’m a man who likes butt play. Is there a way to bring this up without freaking out my partners? Historically, I’ve had only a 10 percent success rate. Maybe I’m just saying something wrong? — Name withheld by request

Dear Buttie System: It may be that anyone’s success in getting their averagely heterosexual female partner to don a strap-on and peg him or in any other way stimulate his anus, could only be 10 percent. And that might be aggressive if the letters we get are any indication of what’s lurking in the hearts, and butts, of men. How to drive that number higher? Ask more often and choose partners who better accord with what you, and your ass, need. Good luck!

Bottoms Up!

EUGENE, SIR: I think it should be mandatory for men to have their partners put a dildo up their butts at least once. Just for some perspective. Could help. Won’t hurt. Well, not much anyway, right? — “Carly”

Dear Ms. “Fiorina”: I see what you did there. Clever. And I support your premise for those who are willing. But really and realistically, sex is supposed to be FUN. Tonally, your letter suggests it is anything but. In fact, the way you cast it? It sounds downright punitive. To what end? To make men more understanding? Is the road to understanding now populated with dildo’d bottoms? Perhaps a key to why ignorance is bliss.

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