Vaginal sex tends to feel better when people play around with their own bodies before enlisting a partner, building up to penetration. Please enter a valid email address Sign up Oops! The risk of contracting AIDS from having anal sex with an infected partner is very high, so a condom should always be worn for anal sexual health reasons. Anal sex, however, can be safe so long as you are engaging in safe and protected sex. You want to make the experience enjoyable for both of you, and make sure you are aware of the risks in order to take the proper safety precautions. Sinclair suggests testing the waters while you shower. When people start experimenting with sex, they typically confine touching to their genitalia. You should have protected sex, regardless of whether you engage in oral, vaginal, or anal sex," says Evelyn Fisboin, MS, a marriage and family counselor at the Mind Spectrum Institute in North Miami Beach, Fla. There is also a risk of infection if couples do not practice safe sex and follow anal sex with vaginal sex. According to Alicia Sinclair—a certified sex educator and founder of b-Vibe , a sex toy company dedicated to anal play—one common explanation for squeamishness is a lack of preparedness. How to have anal sex: Without proper lubrication and slowly introducing the anus to the experience, anal sex may be painful.