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Everything Should Have Been Right, but It Went So Wrong: Her First Foray with Anal Sex Yielded Shocking Pain

She and her boyfriend had anal sex for the first time, and although they tried hard to make it pleasurable for her, they didn’t succeed. She felt all pain – no pleasure – and is now wondering what they did wrong. Both are willing to give anal a second try, but not without a few tips so they don’t notch another failure on their belts.

Case #: 1677


My boyfriend and I tried anal sex for the first time last week, and it didn’t go too well. At first things were cool because we were just doing foreplay, and he was loosening my hole with his finger. We slowly went into it just to make sure nothing bad happened. Once he thought I was ready, he stuck in only the head of his penis, and immediately I started to feel pain. I know it’s supposed to be painful – like the first time you have sex – but this was at a whole different level. It wasn’t pleasurable at all. I don’t know where we went wrong. I was relaxed, so I don’t understand. What can be done to help get this fixed and so we can give anal another shot?


A woman’s first experience with anal sex is usually less than perfect. You can blame this on misinformation – anal sex continues to suffer a taboo reputation. But here’s the truth: anal sex does not have to be painful. The fact that it does only means you and your partner are doing something wrong. Practicing the proper techniques is essential to enjoying anal sex – and don’t worry, it can be enjoyable.

The Ins and Outs of the Anus

You can think of your anal cavity as a tube that begins at the rectum. It is about one-and-a-half inches long and composed of two primary muscles. The first are external – they form the anus wall and keep it closed. Internally is another band of muscles that cannot be consciously controlled. They tighten in response to anything that’s pushed into the anus, which accounts for most of the pain women feel during anal sex.

But that pain is not one-dimensional. It’s also caused by numerous nerves in the skin at the anal opening and internally around the anus. This network explains why the anus is so sensitive. Coupled with the organ’s lack of natural lubrication, you have a recipe for disaster where anal sex is concerned.

Why Some Women Enjoy Anal Sex

But many women – and the number is on the rise – enjoy backdoor play. Why? Because they know what they’re doing. First and foremost they take their time. It sounds like you also did this, but most women who go for anal sex reach orgasm first. Their lovers stimulate their clits by touching, licking or fondling until they are awash in pleasure. This is key – orgasms relax the body and cause the brain to release a host of feel-good chemicals. You can see this is a win-win situation for you if you’re going to indulge in anal sex.

Orgasms also make you more willing to explore new techniques and positions in bed. That brings us to our next point: in order to enjoy anal sex, you must want it. You need to be in a safe, playful and mutually pleasurable relationship before you can find real satisfaction in sex. Once you and your boyfriend have that, anal sex will seem like a natural progression in terms of experimenting. It will lose its stigma, and you’ll lose your fear.

Before you again try anal sex, you need to know it causes some women to orgasm, meaning it can be just as fulfilling as vaginal intercourse. We already explained the anus is lined with numerous nerves. In addition, the female body is loaded with erogenous zones, some of which may be in the anal cavity (each woman is a little different, so we can’t say definitively that every woman can orgasm from this practice). Even if you don’t reach climax, the likelihood that you’ll enjoy sex increases with backdoor action. The explanation is simple: couples who experiment have more fun.

Don’t Forget the Lubrication

The one crucial element with anal sex that we haven’t yet touched on is lubrication. You will need lots of this for successful practice. Lubrication helps muscles and skin stretch more easily so the anus can accommodate the penis. (SEE: Guide for Anal Lubrication Selection) It also protects against damage like tears and abrasions.

A water-based formula will likely feel the best to you. Keep the tube handy throughout anal sex, and remember to communicate with your boyfriend. If something he’s doing hurts, tell him so he can stop. Also remember to go slow and view anal sex as an adventure – you might just find you like it.

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Views: 138

Ideas: Women's, Intercourse Pain

Blog ID: 59057

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