My wife and I enjoy anal sex regularly, we do it nearly every time we have sex and it’s extraordinarily pleasurable for both of us. It is more intimate than vaginal sex so it brings us closer together. She also has bigger orgasms through anal sex than other ways.

For a first-timer (woman, receptive) I’d say make sure you’re the one calling all the shots. You be in charge, whether that means telling him what to do and how, or by you physically controlling what is happening. Go very slowly and make sure you’re very turned on first. Orgasms relax you, and engorge the general area with blood, protecting tissues and providing more overall moisture ‘down there’.

The best lube out there by far (and I’ve tried them all) is called “Liquid Silk” by Bodywise, but many other kinds will do too. If you are fluid-bonded with your boyfriend you could use an oil or petroleum based lubricant (vaseline is very good) but these are not latex condom compatible.

– B