Tip #1: Play Safe
There are some serious safety issues regarding anal sex that you need to be aware of at all times. First and foremost, whatever touches the anus shouldn't be touching anything else. Never never never take the penis out of the anus and put it into the vagina. That can lead to serious infections and other complications. 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. This isn't just limited to AIDS; herpes, genital warts, syphilis, gonorrhea, etc. 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.
Tip #2: Lube, lube, lube
One of the most important thing to remember when thinking about anal sex is that, unlike the vagina, the anus isn't self-lubricating: you gotta bring your own grease. And, the more lube you use, the better. It will make the initial penetration much more easy and less painful for the woman and make the whole experience, for both of you, much more pleasant. The most common suggestion we get from our readers is to use LOTS of lube; we just can't emphasize this point enough.
All kinds of lube are used for anal sex, from spit to Vaseline to 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. We'd recommend products like AstroGlide or KY Jelly, available in any drug store. 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 anesthetic 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 root problems, not anesthetizing yourself so it's easier to endure.
Tip #3: Start Small
Simply put, a penis is an awful big to be the first thing you stick up someone's butt . Better to start with something smaller and work your way up. Fingers are an excellent beginning point. Use one finger, then two, to initiate your partner into the mysteries of anal penetration. Try it while performing oral sex for an extra thrill. Be sure your fingernails are trimmed, not to forget the lube, and you might even want to wear latex gloves.
As your partner gets used to your fingers, you might graduate to a butt plug or a small dildo. Dildos are available in all shapes and sizes. Go shopping together to get one she thinks she can handle. Remember, though, don't 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.
Tip #4: Turnabout is Fair Play
Whether you're trying to convince someone to have anal sex or trying to figure out how to do it in a gentle, pain free manner, there's no better preparation that exploring anal play with yourself.
A partner is much more likely to consent to anal sex if she's seen that you're open to being on the receiving end as well. Encourage her to use her fingers inside of you, or even purchase a butt plug or small dildo and let her use that. Once she's seen you're willing to do it, it'll be hard for her to resist exploring it as well.
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 for your partner. You might also be surprised just how much you like it...
Tip #5: Clear the Way
Before having anal sex, the woman should have a good, complete bowel movement. If she doesn't, the man may find himself encountering far more fecal matter than he might have liked (i.e. packing the fudge). Now, for some people doing this on-command might not be the easiest thing, and straining to defecate is not healthy. A high fiber diet may help things along and is good for your health in any case.
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 the enema route, we'd recommend doing it several hours before you plan to have anal sex, rather than right before the act.
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