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I Hate That Guy
Alright, so you've finally worked up the nerve to ask the question to the woman you're seeing. Would she like to have anal sex? She looks at you with a grim look on her face and flatly says "No way". Foolishly you ask her why, thinking that somehow you'll be able to convince her otherwise. "I tried it once before with another guy. It just hurt too much. I never want to do that again."
That's the guy I hate. The guy who ruins anal sex for women for the rest of their lives because they have no clue what they're doing. Those who have successfully done the act can blow by the rest of this post, unless of course you'd like to fact check me, or provide extra comments as they're always welcome. For those who are interested in trying it out and never have (or caused your woman severe pain when you did)... allow me to provide a few helpful rules, in no particular order. I do this purely for my own benefit, as I may be dating your current girlfriend after she dumps you.
Rule 1: Don't Watch Porn for Tips on Anal Sex. Except for a few instructional how-to movies (like this one and this one), they cut out all the really important stuff that leads up to good anal sex, and only show the penetration itself.
Rule 2: Lube! There is no such thing as too much lube. The rectum is not like the vagina in that it doesn't produce any natural lubrication.
Rule 3: Lube! Yes - It's that important. I recommend Astroglide.
Rule 4: Take Your Time. If she's never done this before, then I hate to disappoint you, but it's not going to happen immediately. You will need to warm her up. This is not something you should rush through.
Rule 5: Be Gentle. Start with a well lubed finger, and take your time. I recommend always using fingers first even when you've been doing it together for a while. It's a good way to make sure everything is well lubed inside her and you don't hit any "dry spots" which can catch and cause pain. After 20 minutes or so, add a second finger and keep going. Kiss her. Talk to her. Encourage her.
Rule 6: Don't Tell Her to Relax. I find this is something akin to telling someone not to look down when crossing a rope bridge. This is not a solid rule, you may find that it's helpful. In general however, I've found it to be counterproductive. It makes her think about being tense, which will make her tense up. Instead put her at ease over how she's doing so far and that you're not going to rush anything. Once again, kissing and encouragement are the order of the day.
Rule 7: Be Clean and Safe. Some sort of flush is often times helpful. It can help her feel more confident about her body and relaxed about the whole thing. Either way, use a condom. There are some nasty things that can lurk up there. And of course never go from ass to pussy, or ass to mouth for that matter (though I'm sure some people will diagree with me).
Rule 8: If It Hurts, Then You're Doing Something Wrong. I will grant you that its very difficult to do it without at least a little bit of pain in the beginning. Just remember, this is supposed to feel good for both of you. If it hurts then you either didn't lubricate well enough, you didn't spend enough time fingering her, or she's just not confortable enough. Stop what you're doing now and figure out how to make it better before you become that guy. That might mean stopping altother and waiting until another time.
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