Feb 122002

My girlfriend has hinted that she wants to try anal sex, but she is too shy to talk about it. She likes me to finger her ass, and she goes crazy when I lick it as well. The problem is that every time I try to penetrate her ass, I lose my erection! I think I must be too nervous or something, but I don’t have this problem when we have vaginal sex. Because of my problem, we have never been successful in anal penetration. I think it takes me such a long time to try and position my dick that I just lose my excitement. Anal sex is one of the most arousing fantasies for me—please help me so I can do it!

—Mr. Softie

If you have a less than solid erection, you can often “stuff it” into her vagina, and, once you’re in, you achieve a full hard on. It’s a little trick which plenty of men do. However, that same shortcut simply does not work with anal penetration. The bottom line is that you need to have a rock hard cock to get it into someone’s ass.

Well, since you have no erectile issues during vaginal sex, then your problem is probably not physical but psychological. My initial question for you is do you have any fears about fucking your girlfriend in the ass? Some men are anxious about hurting their partners. Somewhere in the back of your mind, you may be afraid you’ll cause her pain or perhaps a past lover has told you that you hurt her. If you think you might have this fear, reassure yourself and your girlfriend that you’re going to warm her up, use lots of lube, and go slow, so that it won’t hurt.

Speaking of going slow, it sounds like that may also be part of your problem. You wrote about how much time it takes to get in position, and you may be losing the momentum of the moment. If that is the case, perhaps your girlfriend can stroke your cock as you’re maneuvering it or talk dirty to you to keep the fantasy and the anticipation going while y ou get ready. I’m concerned that you say she’s too shy to talk about anal sex. You may have poor communication both in and out of bed, and that could be contributing to your anxiety or ambivalence about anal sex. Talk to her in a safe, non-threatening aware, share your desires and fears, and agree to work on this issue together.

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