What's the best, most painless way to have anal sex for the first time?

This is probably slightly irresponsible for me to suggest but its true: start by having a few drinks- alcohol relaxes the muscles a little, and will also help loosen your inhibitions (concious and subconcious) the more nervous you are, the more likely you are to "tense up" involuntarily and make the experience more painful. Relaxing is key. Also, get your partner to perform oral sex first to help relax you further; the more turned on you are to start with the more likely you are to enjoy it. Use lube, such as KY jelly to make things easier, but don't over do it or it'll be really difficult to get it in (which is quite amusing, but not that sexy) after you've done it a few times you may find its not always necessary, but its good to have handy anyway. Also seeing as the risk of STD's is slightly higher than normal sex, its a good plan to use a extra strong condom (you can get them designed specifically for anal use now) and don't have normal sex afterwards until you've washed. Best position is either doggy style or lying flat on your front, perhaps with a pillow under your lower body (I think the second is usually most comfortable, but I imagine this varies from person to person) First your partner needs to start by pushing one or two fingers in gently to "open you up" and get you used to the feeling- "gently" is the operative word here, he needs to introduce his fingers quite slowly, and not poke or move them up and down really fast or anything. (Also make sure he's trimmed his nails- ow!) when you feel ready he should gently push his penis in, going slowly and gently- if you feel really intense pain at any point ask him to stop, and try again later- for some reason our bodies seem more receptive to anal sex at some times than others. I(no idea why) - once he's in he shouldn't thrust too vigourously at first- he should build up slowly (this takes self-control admittedly, but its possible) He should also be masturbating you with his fingers or a vibrator at the same time to give you maximum pleasure from the experience (If you can stand it a vibrator in your vagina during anal sex is quite a unique sensation!)
I believe that if its done right, most people can get to enjoy it, but then, everybodies different, so if it really, really hurts- then stop!
Enjoy.

You should always use an enema before anal sex. This alone will loosen the muscles. Then penetrate with your fingers, one at a time, until you can take four. You are then ready for penetration with your partner's penis. Have him insert it slowly. If you experience pain, have him stop but not pull out, breathe deeply and wait for the pain to subside. If he pulls out you just have to start over. It will feel great once you relax. (at least it does for guys - the prostate is stimulated and its amazing!)

I'd suggest starting with digital (finger) penetration. First one, then two, etc. Go slowly! You'll want to use a lot of water based lubrication (as oil-based lube is known to destroy condoms). Just go slowly and use lots and lots of lube (too much is almost enough). Make sure you remind the receiver to breathe deeply and try to relax. Giver, be gentle.

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Why don't you ask your boyfriend...u prolly been doing it to him

Honestly... I just tried anal sex for the first time last night. I would like to recommend "Anal Ease" It's a desensitizer and it works wonders!!!

http://reardoorwatch.com/painless.html]Anal sex can be achieved painlessly simply with the initial penetration done while both partners are lying on their sides. A few slow strokes will bring enough relaxation so any position can then be assumed.

lot of good answer..but let me be a little clear..I am a male.

http://en.wikipedia.org/wiki/Anal_sex#Risks_and_protective_measures

Be the MALE!

Read this post. It tells you what you need to know: http://mflife.wordpress.com/2006/10/12/anal-sex-101/

why the downrating...any positive feedbacks???

for both of you to be in seperate rooms.

The enema suggestion is right. - but add lotion and glycerin suppositories - when you want to shit then you will be open for it. Sometimes both happens - if the guy wants it - it will be ok.

Use lots of lube, NOT KY-it sucks. Use at least astroglide. Liquid silk or maximus are better. Or go to a silicone based on for the most amount of long lasting lubrication. Start off with a finger and then move to two. It helps to be stimulating her and teasing her clit when you do this. Feel free to make her orgasm - it will relax her. During anal, keep stimulating her clit or get her to use a vibrator on herself. She will have a ton of fun.

Don't do it.

Lets KISS (keep is simple, stupid) this. This is going to sound similiar to other answers. Get your partner relaxed, usually 420 or a few drinks helps a lot. Perform oral. Use lube, I just use hand lotion, but if you want KY or a little astroglide. Use just enough to lightly coat your dick. And for your partner's sake, warm it up with a finger and then move up to two if you can for a little bit. And here is where it is different. Do NOT do it doggy style, or missionary, or any other position that will cause the girl to tense up her muscles. Remember it takes muscle to prop your ass or legs up. I have found that on your side behind your partner is the best way to go.

Woman on her back is the best way for me and her. Just need to pull her legs back over head to expose anus. She needs lots and lots of pussy and anal licking and a good lubricant, although it is possible to get it too slick. And you don't want that sticky stuff all over your hands. And guys, the ass is not to be pounded like a jackhammer. Just get it in and be real real easy with her, cause she's gonna get her jollies masturbating while you are filling her butt with your cock.

Doing it with somebody besides me could reduce your pain level quite a bit... ;~)

Hi, I want to perform anal with my g/f but i want it to be the least painful for her...Any tips?
I would love to prove to her its not so bad..Thanks

Ride it like a pony thats what i did for my first,now any position works for me a feels terific but thats just me its different for other guys.BTW im a guy.