The following is another of one of the same questions I am constantly being asked. Although it may be a little redundant to keep answering them in my columns and blog, it's a question whose answer needs to remain visible and accessible.
How do the boyfriend and I go about anal without it hurting like hell? He really wants it but I don't want the pain.
Anal sex is not supposed to hurt. If it hurts, you're doing it wrong.
Rule number one: LOTS OF LUBE. When it comes to anal, there is no such thing as too much lube.
Rule number two: RELAX. There are two sphincters in your lower colon. You have far more control over the one on the outside, let it be loose. The second will follow. Most people walk around at all times with their assholes clenched tight. This is not healthy! Learn to relax your butt.
I would never recommend having anal sex while drunk, especially not for the first time, but having a drink or two, and only a drink or two, could help loosen you up all over. This includes your inhibitions and your sphincters.
Rule number three: COMMUNICATION. Go slow. Verbalize your feelings to your partner. Whoever is on the bottom needs to be in control. The bottom needs to say exactly what feels good and what doesn't. They need to dictate the depth and speed of the penetration. The top needs to oblige the bottom for buttsexing to be successful.
Rule number four: CONDOMS. Bums are yucky. Also, the fragile anal tissue is more prone to tearing than vaginal tissue is. If you're doing it right, there shouldn't be any tears, but just in case - be safe! Broken skin on one's genitals is the easiest way to transfer an STI or STD. A condom will greatly prevent this possibility.
The best way to prepare or "train" yourself for anal sex is to stimulate the outside of your anus, either on your own or have a partner do it. Use lube and your fingers. When you're ready, slide a single finger in and get used to that feeling. Try using plugs and vibrators of varying size to get yourself used to having something a little larger up there.
Finally: Even though anal sex can be uncomfortable, it should never hurt. If it hurts, stop. Pain is your body's way of telling you that something is wrong. Don't let it stop you from trying again, though. It's possible that the person doing the penetrating has been blessed with a penis that is just too damn big to fit in your butt. Lucky you. Enjoy it where it actually fits.
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