Anal Sex, Safe Sex: With Condoms Use Plenty of Lubricant!

These are the Three Words of successful first-time anal sex: LUBRICANT, LUBRICANT, LUBRICANT! And when following safe sex guidelines and using a condom, using a good lubricant becomes doubly important. Condoms are much less slick than the supersmooth skin of your cock. Unless you want her nursing a chafed asshole for the next three days, grimacing at the thought of further anal friction, smear the entire surface of your latex-sheathed prick with about a teaspoonful of astroglide. Then, after you're in her, freshen the coating of lube with a squirt every minute or two. It will be a bit messy, but she will love you for it.