Anal hurts too much...

Q. My girlfriend and I got drunk and ended up having anal sex for the first time. This was a big fantasy of mine and both of us really got off on it. Since that night, we've tried to do it a few times, but she kept saying that it hurt too much, even to get just a finger in her rear. She swears up and down that it felt good the first time, so I just don't get why we can't get to that point again.

A. It's exciting that the two of you had the opportunity to try anal sex, especially since it was a big fantasy of yours … but doing it when you're drunk doesn't count for much, especially when you try to replicate the activity while you're in a sober state.

Having a few drinks relaxes the way we engage in activities that make us nervous, which could account for the reason why your girlfriend enjoyed anal as much as she did at that time. 'Liquid courage' lowers inhibitions and eases tension, which then in turn relaxes muscles - a huge help when it comes to slackening the tight squeeze of an anal sphincter. Booze also pacifies pain, or at the very least dulls one's ability to recognize their true pain threshold.

Anal sex can definitely be pleasurable for your girlfriend and, in some cases, be even more stimulating that vaginal sex. But now that you're trying to do it sober, you've got to help her get into a state of arousal and relaxation if you ever want to get her to open up to you again.

Think of anal play with an emphasis on pleasure, not just penetration. The most useful technique that you can use is stimulating your woman's erogenous zones according to her preferences while you play with her anus. If multi-tasking isn't your strong point, encourage her to Masturbate and/or use an Anal Sex Toy as you take the time to indulge her with Analingus, Anal Fingering, and eventually Anal Intercourse. Check out our advice post, Step by step anal sex guide, for more helpful details.

When it comes to butt play, you need to be cognizant of what you do with your partner, particularly if you're less experienced in this sexual area. Rectal tissue is delicate and vulnerable to soreness and tearing. Additionally, if you don't play safely, bacteria from the anus can migrate easily into sensitive areas like the mouth and vagina - via say, fingers and penis - and potentially cause inflammation, infection, or STD/STI transmission.

Avoid being downright drunk the next time you guys want to try any new sexual activity - or at the very least, limit your consumption of alcohol to a reasonable amount. It will make for a more rewarding and less risky long-term outcome in the future.