Advice about Anal Sex from an Anal Slut

I caught the tail end (the butt end?) of a discussion on twitter yesterday about how to introduce anal sex into a couple's repertoire.  While I've been a self-proclaimed anal slut for years now, and am perfectly comfortable with the label, I do remember back when I was first getting started and facing the same fears and anxieties other women are still facing today. So these are my little bits of wisdom, many of which I wish someone had told me. I now pass them on to you lovely readers.
(The pictures, however, are probably completely unnecessary. I just love looking at them.)

1. When it comes to anal sex, the first barrier that must be broken down is the psychological one. If a woman is squeamish about things going into her ass, or even touching her asshole, she is going to have a hard time picturing herself enjoying anal sex.

Possible solutions: get some porn videos that include a lot of anal--the ones that focus on anal sex will usually give a hint to that fact in the title. There are even porn videos out there that work like a "how to" guide for anal sex. Watch them as a couple, together. Talk about them.
The guy should be very verbal about how much the idea of putting things (not just cock) into his lovely woman's ass turns him on. He should also tell her, over and over, how much he loves her asshole in general, how much it excites him, how he sees it as something sexy, provocative, and adorable. A woman sees her asshole as something dirty; he must get her to see it his way.
Once a woman is open to the idea of something, anything, going into her ass as part of sexual play, with the right mindset and enough time the rest will happen on its own. But remember: once you claim the privilege of filling the asshole, you must also take on the responsibility of keeping it safe and feeling good!

2. The asshole is not like a pussy: it is naturally dry, and stays dry. In any kind of sex, dryness can lead to pain, and small tears in the skin; not sexy, and not what you want for that cute, adorable asshole you want to violate.
Solution: LUBE. The lube must be coated liberally on whatever is about to be pressed into the asshole. In addition, it also helps if lube can be inserted into and around the asshole directly; a finger does this job nicely. Be gentle!

3. The asshole does not stretch as fast as a pussy. The skin is more fragile and tight.
Solution: stretch it slowly. The tightest part of the asshole is the internal sphincter itself; once you are past that, smooth toys will slip through easily. In fact, the body's natural reaction is to suck things in! Start with a pencil-thin anal toy, then gradually get wider. What's important here is not length, it's width; so don't bother getting a toy that's 7-9 inches long, because it won't make a difference. All that matters is dilating that internal ring of muscle. And again, lube is important. The asshole will stretch much faster if you're using enough lube. But once a toy feels comfortably in place, there's no point leaving it; you might as well take a break, or move on to a bigger size. No point leaving it in for hours at a time. In fact, if the lube gets absorbed naturally by the tissues, the toy will begin to hurt, and you won't understand why and will frighten yourself for no reason.

4. The asshole is more sensitive than the pussy. Note: I don't know if this is true for all women. I do think it's true for most anal sluts. Pain is more pronounced, but then again, so is pleasure. Every stroke and slide that hits the nerve endings just so is like a stab of pure ecstasy. But angle things the wrong way, and it's like lemon juice on a paper cut.
Solution: Go slow...and I'm sorry, but--expect some pain. If you accept that this process will take time, that there will be some discomfort, some aching, and yes, some stinging along the way, but that your partner is only trying to figure out what pleases you and is doing his best to hurt you as little as possible, then the whole "introductory" time should go a lot faster. Remember, stretching the internal sphincter is the hardest part--and the most painful. Once that's done, the pain should lessen.
Once you've had anal sex a few times, you can anticipate how bad the initial pain will be, and prepare yourself for it. And--if you get off on the pain--you'll start to look forward to it; it becomes part of the thrill. But the initial pain never really goes away. You just come to know what to expect.

5. There's only one position for anal sex: doggie style.
Solution: OH HELL NO. No, no no. Any position you can have vaginal sex in, you can have anal sex; in fact, some positions are easier when you're having anal sex!

Sometimes the weight of the man on top feels amazing.

He can watch her play with herself this way.

This position gives her more control.

This picture is completely gratuitous. 

Some advice:

• Once a woman is ready to try (operative word being "try") something up her ass, do NOT move directly on to cock. Try a finger first, and slowly move on to two; and when she likes (not tolerates, but likes) that, move on to a narrow toy, preferably one that vibrates. Only when she feels very, very comfortable having other things up her ass should you move on to cock. It may help if you give her more control over what's in her ass in the beginning; turn it into a show. 

• Anal toys are not like vaginal toys. They have a wider handle at the end to prevent the toy from being sucked up the ass. If you are using a regular dildo or vibrator inside the ass, for god's sake, hang onto it tight and don't lose it up there. The last thing you need is a trip to the ER because you lost track of a sex toy somewhere up your intestine.

• This is not a "vaginal or anal" scenario. You can have a toy in her ass, and your cock in her pussy; or you can have a toy in her pussy, and your cock in her ass. Or you can move your cock from her pussy to her ass, if she's lubed up enough. But--and this is a big but--DO NOT go from ass to pussy. Not with cock, and not with toys. This can lead to bacteria entering the vagina, which can cause infection. Anything that has been in the ass must be washed before it can be reintroduced to the pussy, or her poor pussy may end up feeling something like this:

• When poking something into the ass for the first time, use a blunt tip. If it's a finger, don't poke it straight in; use the finger pad to press it in first. Seduce the asshole into relaxing, and opening a bit on it's own; then press your point home. You'll see the difference, and she'll feel the difference.
• If the asshole constricts, do not pull out. Do not move while the asshole is constricting involuntarily. Wait, let the spasm pass, and then ask her what she would like you to do. Sometimes she will tell you to get out immediately--and sometimes she will tell you to continue. But if you try to pull out while she's all tight back there, you'll only hurt her. (Which may be the point later on, but not right now.)
• Once you both get a feel for what works for both of you, you can incorporate the pain into the act itself. You can tie her up, and have fun stretching her a little faster than what she's used to; or you can cuff her down, and enter her fast from behind. The possibilities are fun and endless.

So have fun, and good luck! I hope this post was of some use to you. If there's any question still lingering, don't hesitate to contact me in the comments section or via twitter, and I'll do my best to answer it.