Mar 222001

It’s wonderful that you are so pro-anally inclined. I am a connoisseur of fine posteriors (my wife’s being on top of the list — sorry, don’t feel bad!). We watched your video,
The Ultimate Guide to Anal Sex for Women, and enjoyed it very much. As I was trying to coax my wife into the act, somehow, she tightened up and it became a painful ordeal. We’ve had anal sex before, and she enjoys plugs in her butt when we are having vaginal sex. But she can’t take my turgid member as frequently as I would like.

—Help My Turgid Member

Glad to hear that you worship your wife’s ass. Now, you need to take a little extra care so that both of you can enjoy anal sex. First of all, if she’s experiencing pain during penetration, there may be several different causes. In general, you need to concentrate on giving her a lot of foreplay before you move on to putting your dick in her ass. Use your fingers, then a dildo smaller than your dick, and let her get used to that first. Go slow, and make sure everything feels good to her before graduating to more fingers or a bigger toy. If she experiences discomfort or pain, there may be too much friction. Add some more lube, and see if it feels better when you slide back in. Or you could stop the movement of your finger or the toy, but stay inside; see if the pain subsides. If she’s still hurting, stop penetration altogether and focus on more external stimulation — a hand job, oral sex, more foreplay.

Let her know that she’s the one in control of the situation, and if she needs to, stop the activity altogether. She needs to relax, take some deep breaths, listen to her body, and tell you when she’s ready. After she is warmed-up and ready for your cock, lubricate your turgid member and re-lube her ass. Place your cock at her anal opening and hold it with your hand to help you guide it. Now, you have a few options:

  1. Have her move her body toward your cock (forward or backward depending on your positions), while you guide it inside.
  2. Rub your cock against her opening. This external stimulation should relax the anus. As the sphincter muscles contract, the opening appears to “wink” at you. As it winks open, take the opportunity to slide in.
  3. Press your cock against her opening and gently push against it (she may want to either relax or bear down in order to let you inside).
  4. Penetrate her ass with your finger, withdraw it, and while her anus is open, gently insert your penis.

Have her stimulate her clit as you penetrate her. This will relax and arouse her, making penetration easier. Deep breathing will help her relax and concentrate on opening her ass to you as well as circulating blood to her genitals. (Taking shallow breaths tightens the muscles and inhibits the engorgement process.) If you’re having trouble hitting your intended target (hey, those two holes are close together and it’s slippery with all that lube), have her wrap her fingers around the head of your cock and help to guide you inside her ass.

When you first get inside her ass, don’t go too deep. Again, you want to give her ass an opportunity to get used to your penis. Keep your movements slow, gentle, and subtle at first. When she’s ready, you can venture farther inside and start some slow thrusting. She should tell you if she wants you to go deeper or faster or both. Then, it’s simply a matter of exploring what feels good for both of you.

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