Whatever goes in the anus shouldn't be touching anything else, whether it's fingers, a penis or toys being put inside you- don't let them stray. He should never take his penis out of your anus and put it into your vagina. This can lead to serious infections- you are both at a higher risk of cystitis and a burning sensation when you pee is never a good feeling! After any kind of anal play, you should immediately change condoms and wash the relevant body parts thoroughly.
Of course, STDs are also a major concern with anal sex if you are not having it with your long term partner who has been tested and you are certain is free of them. AIDS, herpes, genital warts, syphilis, and gonorrhoea can all be transmitted through anal sex. You shouldn't be having anal sex without a condom; it's not worth the risk to either partner.
Lubrication, Lubrication, Lubrication
One of the most important things to remember when thinking about anal sex is that, unlike the vagina, the anus isn't self-lubricating: you have got bring your own grease. The more lube you use, the better and keep applying as the anus soaks it up quicker than the vagina. It will make the initial penetration much easier and less painful for you. It will also make the whole experience, for both of you, much more pleasant, we just can't emphasize this point enough
All kinds of lube are used for anal sex; spit, Vaseline and high-tech silicone-based lubes. We'd strongly recommend spending a little money to get a high quality water-based lubricant; remember, an oil-based lubricant like Vaseline will degrade the latex in a condom, destroying its usefulness and safety against infections. Note, though a condom may be "lubricated", they typically don't offer as much lube as we'd recommend for anal sex.
There are some specialty lubes designed for anal sex that include an anaesthetic to numb the woman's sensation and make anal sex less painful. We'd advise against these products. The simple fact is; pain is a way of your body telling you that something's wrong. If you're in pain during anal sex, you need to focus on solving the problem, not anesthetizing yourself so it's easier to endure.
A penis is awfully big to be the first thing you stick up your butt. Better to start with something smaller and work your way up. Fingers are an excellent starting point. Use one finger, then two, to allow yourself to become accustomed to the feeling. Get him to do this while performing oral sex on you for an extra thrill. Be sure his fingernails are trimmed, don't forget the lube, and he might even want to wear latex gloves.
As you get used to his fingers in that end, you might gravitate towards a butt plug or a small dildo. Both are available in all shapes and sizes. Go shopping together to get one you think you can handle. Remember not to put the dildo into the vagina after putting it into the anus. The safest way is to put a condom on the dildo before using it, and to wash it thoroughly immediately after.
Be the first
If you are talking about this with your partner or thinking about asking them to start playing with your back passage- then try it out on yourself first.
Just like telling your partner how to get you off when he touches your clitoris, or your vagina, if you can let him know how you like to be fingered there, then you are on a faster track to pleasure.
Of course, anal play on yourself is a great way to learn how anal sex feels and to learn how to make it more comfortable when your partner finally enters you. You might also be surprised just how much you like it...
Although it's not the nicest of things to talk about - make sure that you have a full bowel movement before anal. If you don't- he will be 'packing fudge' or worse it might be pushed out if you stools are a bit loose. Anal sex might be something you need to plan in around this- or your first time might be your last if the smell of sex is replaced by the smell of faeces. Straining to defecate is not healthy. A high fibre diet may help things along and is good for your health too.
Of course, if you really want to clean things out in a hurry, you can purchase an enema from any drug store. There's some controversy about this; some people feel having an enema first can actually increase the irritation during anal sex. If you're going to go down the enema route, we'd recommend doing it several hours before you plan to have anal sex, rather than right before the act.