Pain in the Butt

I’m a gay guy who just got into a serious relationship that I’m really excited about. So far I’ve been topping him exclusively, even though he considers himself a top. I used to bottom like a champ, but have recently been much less ‘accepting’ when people try to fuck me. I’ve been practicing with a dildo for him, and am able to fuck myself pretty easily, but for some reason, whenever he tries I’m too tight and it’s too painful for me. Please help!
—Bottom Blues

When done properly, anal sex should not hurt.

Usually, when it does hurt, it’s because something isn’t right—either physically or psychologically. You’ve successfully bottomed before and you can fuck yourself with a dildo, which makes me think that this is primarily a psychological issue.

So my first question is, do you actually want to be topped by your partner? Anal sex can be very psychological because you need to be mentally relaxed and ready so that the muscles in your ass can physically relax.

Think about whether this is something you really want to be doing, because if not, your body may be involuntarily reacting to unspoken feelings. If that’s the case, you need to explore why that may be and maybe discuss it with your partner.

If you do really want to be topped then it’s possible that you’re just a little nervous because you haven’t done it in a while or you’re generally a little tighter than usual. Both are problems we can solve!

As usual, communication with your partner is key. In terms of possibly being nervous, try to identify what it is that worries you. Sometimes it’s trusting that your partner will stop if you need to, or that he’ll be careful in the beginning.

If that’s the case, start a dialogue and talk about what you can both do to ease those fears. If your partner is aware of your concerns, it will take some pressure off you in the moment.

While it’s a good place to start, fucking yourself with a dildo is going to be much easier because you’re in complete control of the situation, unlike when your partner might be doing it.

Start practicing anal play with your partner if you haven’t already. Use a dildo, his fingers, or whatever you want—just do it together. This will help you get used to him penetrating you in different ways, work on trust, and loosen you up a bit more in preparation for his dick.

Once you’re ready to get fucked by your partner, go back to the basics of anal penetration.

Get really hot first and don’t skip foreplay, because the more turned on you are, the more relaxed and accepting your body will be.

Lube up a lot to make penetration easier and to minimize any discomfort. Prep yourself by starting with fingering or toys before attempting penetration with his dick.

Start off in control of the penetration, moving yourself on his dick rather than him fucking you. And remember not to push yourself if it’s painful, because it shouldn’t hurt and you don’t want to cause any actual physical damage.

It may take some time before you’re really ready to be fucked, but try not to put too much pressure on yourself to get there—because that might just make it worse. This is where communication really helps, because knowing you have full control in stopping if you need to will help you relax.

Good luck and write back in if you need more help!

Submit your questions anonymously at and check out “Sex & Pancakes” on Facebook. Need some extra help? You can always contact Concordia Counselling & Development at 514-848-2424 ext. 3545 for SGW and ext. 3555 for Loyola. Got a quick health question? Call info-santé at 8-1-1 from any Montreal number.

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