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Enjoying Anal Sex: A Guide for the Uninitiated

Her boyfriend wants to try anal sex. She is afraid of negative outcomes, and doesn’t feel prepared. What does she need to know about anal sex, so she can be ready to surprise her boyfriend the next time they’re getting down?

Case #: 1663


My boyfriend is always telling me that he wants me to have anal sex. I am willing to try it, but I don't because I feel like I'm not prepared. I don't want things to go badly and end up in the hospital or something like that. I have been doing research, and there are some very graphic stories of people who tried anal sex and things went downhill right away. How can I be prepared so that the next time we have sex I can be ready and surprise him?


Anal sex isn’t something you can enjoy single-handedly. I can give you some tips on what to do during the process, and how to prepare yourself ahead of time, but past that, it’ll be something for you two to work out together.

Anal Sex is Sex for the First Time

People become used to having sex, and think anal sex must be something similar, and just as easy. However, anal sex must be approached with the sensitiveness and delicacy of two people having sex for the first time in their lives. Truly, having anal sex for the first time is just the same as having sex for the first time: while the insertion process is the same, the methods are completely different and must be learned.

Slippery is Safe

As long as you are using large amounts of lube, you will not do yourself any permanent damage. Problems occur when couples decline to use enough lube. Then the rectum can be pulled outside of the anus, or tearing can occur, resulting in blood and infection from fecal matter. The anus and rectum must be in as clean a state as possible—the anus washed clean, and the colon hopefully free of fecal matter.

Cleanliness is Important!

Other problems can result from not using proper hygiene. It is important to never touch any area of the female genitalia with hands, sex toys, or penises that have been inside or touched the area near the anus. Urinary tract infections, as well as serious vaginal infections, can result from improper care in this matter.

Feel Good Before You Start

Having sufficiently scared you, now I’ll try to alleviate your concerns. You can enjoy anal sex, and many do. The most important thing is that you are completely aroused. You should try to arouse yourself, or have your partner arouse you, as much as you possibly can before you can begin. Watch porn, read a dirty story, touch yourself, be touched, engage in cunnilingus or fingering; whatever it takes to get you absolutely ready to be penetrated.

Easy Does It

At this point, you must liberally coat your anus with lubrication, and coat the inside of your rectum as well with a gentle finger and more lube. Every care should be taken to make this process soothing and pleasant. Any fear or tension will cause your anus to contract, creating pain for you if there is anything inside.

When you begin to insert the penis into the anus, with clean fingers, touch yourself in any way that makes you feel good. The initial insertion of the penis has the greatest potential for pain: go as slow as you need to, stop frequently, and allow your body to come to acceptance of this foreign invader. In time, the sensation should stop being one of unpleasant entry and fullness, and become one of pleasure. I suggest you wait until you begin feeling this enjoyable sensation, before you continue having sex. This stage is one of watching and waiting.


Afterwards, sex is the same as usual. You will probably need to manipulate your clitoris the entire time to find enjoyment in the act, and to have a possibility of orgasm. I enjoin you time your orgasms, because if you orgasm before he does, the remainder of the act will be quite painful to you.

With these notes, I hope you find success in your attempt. Go slow, make sure you’re feeling good, and use a lot of lube! (SEE: Your Guide to Anal Lubricants) Good luck!

What to do

Anal Lube Guide

From the popular brands to the I’ve-never-heard-of’em types, anal lubes serve one job: to make sex less painful.

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