The guy I'm with wants to try anal sex with me. I've never done it, and it's definitely considered taboo amongst my friends. I'm worried doing it might really hurt, have negative health side effects, and that I'll lose his respect if I do it. Any advice?

Anal sex may be taboo, but there are plenty of men and women who find it incredibly pleasurable, as the area is nerve-packed. And, while your friends as well as your man may have their own thoughts and feelings on this "out of the box" sex act, what truly matters is how you feel about giving it a try.

Most importantly, sexual exploration is best done with someone you trust, so you're assured you'll feel comfortable, safe and respected. So, think about what's important to you, and talk it out with your guy before you experiment. Perhaps you'll want to discuss who you'll both tell when the deed is done or if this is something private you don't want to share with others, how he'll respond if you want to stop in the middle of the act, if he's willing to let you play with his anal area and anything else that's on your mind.

Back door action shouldn't hurt if you take your time. However, it often takes practice before becoming enjoyable, as the butt is used to pushing out and not taking things in.

Also, since the anus isn't super-elastic and it doesn't lubricate on it's own, relaxation and lube are essential!

It can be helpful to take a bath as part of pre-play, as a warm soak can allow your body to release tension. Not to mention, it's something fun you can do together.

And, while the anus doesn't store feces, it's common to feel self-conscious that you'll have to make a #2 when you're intimate. So, it can be helpful to go to the bathroom beforehand.

It's best to prep for anal stimulation over several sessions-during solo sex or with a sack session with your guy-by warming up with plenty of pre-play and then incorporating subtle anal play once turned on. You can start with a finger, then try experimenting with anal beads, progressing to a small butt plug (be sure it has a flared base that remains on the outside so it doesn't get sucked inside) and then graduating to the real deal--his penis.

Each time, sensuously circle the outside rim of the anal opening with a well-lubed fingertip. Then, delicately slide a finger inside to a comfortable depth. There are two sphincters--one at the opening that you have control over and another a little further inside that will contract involuntarily. Eventually, you'll feel less resistance and tension, and it you'll likely find that it feels good. Communication is another essential component when you're doing this with your guy. He may be leading the expedition, but you're in charge of navigation telling him what you need--slower, faster, less deep, more deep, pause, continue, etc.

A few health-related tips to keep in mind about anal play:
- Fingernails should be well filed so they don't snag the delicate anal tissue.
- A finger, toy or penis that's been near or in the anus needs to be washed with soap and water before putting it in the mouth or vagina to avoid infection.
- If you and your partner aren't monogamous with each other and STD-free, be sure to use a latex condom to reduce the risk of STDS, particularly viral infections like Herpes, HPV, HIV and Hepatitis.
- Only use water-based lube if you're using latex condoms, and be sure to use a new condom if you're switching to oral or vaginal sex.

The bottom line: Only try back door action if you're truly ready.

To learn more, check out The Ultimate Guide to Anal Sex for Women, 2nd Edition by Tristan Taormino.