Um... if it's painful STOP. STOP. STOP. Pain is a signal that you should STOP what you are doing immediately. The anus is very delicate and can tear easily.

The best things to do are to "start small", with a well-lubed finger or small toy. Perhaps leave a plug in, slowly graduating to a larger and larger diameter. Using beads may also help prepare you for anal sex. Don't forget lots of lube and to make sure you learn how to control your anal sphincter and surrounding muscles so you can relax and contract when it is convenient and pleasurable to do so.

And if it hurts, for heaven's sake, STOP.

If it hurts, something is wrong. Don't just grit your teeth and bear it, you need to work on what the problem is.

There are other forms of birth control other than condoms and the Pill. There are diaphragms, cervical caps, The Sponge IUDs, female condoms, other forms of hormonal BC that sometimes aren't as difficult as the Pill, etc. Also, anal sex isn't really a great form of "birth control" as it is easy for semen to migrate from the anus into the vagina. I always clean up before I remove the dildo from my vagina after anal sex, and even then, he only comes inside when I am in "safe mode" during my cycle. The whole drippage thing gets me too nervous.

I love anal sex, but I have to have had a LOT of oral sex and at least one or two or three orgasms before we even think of having anal sex. Also, I find using something inside the vagina, a phallic vibrator or a dildo, makes it even more fun. We've been having anal sex for years, but I can't go from "Zero to penis" in a second, either. A LOT of warm up, PIV, oral sex, orgasms and fun are required first. It's really our "finishing act" when we are into it.

Do you put the plugs in or your partner? It sounds like you aren't absolutely relaxed/comfortable/tr usting with partner anal activities, but OK on your own. In that case you need to back off and start over. You know you can trust yourself, so your anus can relax - but if there's any anxiety then you'll have a very hard time relaxing, and since you've had pain you will have a hard time relaxing.

I'm a fan of the Morin approach (Jack Morin, author of Anal Pleasure and Health). He advocates starting with solo external touch, learning to like it, then moving to small internal touch and up from there, then starting over again with external touch when you're introducing yourself to partner anal play. Back off from the "full anal sex" and have him rub a lubed finger around your anus, then after a few times (when you're able to relax while he's doing that) progress to a finger internally, then two fingers, than a toy - all the while making sure there's NO PAIN. When you're through that and absolutely ready for penis-anal sex then do lots of foreplay (many women say having an orgasm first helps with relaxation), choose a position where you can relax, then attempt it. If it doesn't work call it off, do some other anal play that you like, and try again another time.