Scarlett Letters: How Do We Make Anal Pleasurable for Both of Us? 

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Dear Scarlett,

So, my partner and I have agreed to be open to anal, and she asked me to use a condom, which I don't mind at all. I'm just wondering how we might go about starting foreplay and getting into the actual act? I want this to be as wonderful for her as possible.

Signed,

Dongman (male, 18)

Dear Dongman,

You're already on the right track by putting her comfort and pleasure first. Anal is popular in porn, but this is real life, and the kind of pounding shown on-screen is rarely enjoyable. The anus is full of nerve endings, and rough sex can hurt.

Yes, use a condom. It will prevent the spread of bacteria. Do not use the same condom for vaginal sex, however, as it carries a very high risk for urinary tract infections. Lubrication is a must. The anus does not lubricate naturally like the vagina, and it is not as pliable. Thicker lubes, like K-Y, tend to last longer than thin, water-based ones. Baby wipes can help if things get messy.

Start with a little penetration, perhaps with a small vibrator or your finger. You might want to do that a few times before going further. When she's ready for intercourse, take it slow. Lying flat on her stomach will be easier and less painful than doggy-style or the missionary position. Or she might want to be on top for more control.

The head is the largest part of the penis, so ease it in and give her a few minutes to get used to it. Ask her how she feels. If she's ready to go further, rock slowly; don't thrust. Moving too fast could injure her.

To your girlfriend: Relax and communicate. Be open to having an orgasm. Stimulate your clitoris, or ask your partner to. Penetration may hurt a bit, and you may feel like you're going to poop, but that sensation fades pretty fast. Tell him to stop if it's painful. And make sure to pee right after to avoid getting a UTI.

Have fun — but take it slow. In the end (ahem), it's about enjoying each other.

Love,

Scarlett