Dear MKE SEX,

A couple of decades ago, I had this one boyfriend who really loved anal sex. (He liked to give, which was great, because I liked to receive!) We did a lot of anal. Not, like, a ton or anything. But quite a bit. Now things are different (new life, different partners, etc.) and I haven’t had anal sex in a long time. Yesterday I stuck a finger in a partner’s bum and it went in like buttah. This guy is great, he enjoys getting pegged by other lovers pretty often. He offered to return the finger favor. I was totally down for it, but it was like he hit a wall. He couldn’t get in without some trauma, and we both knew it was best to just move on to other sexy things. But! Now I need to know! Why does my ass feel like fucking Fort Knox now?

Any ideas?
Tight Ass

Dear T.A.,

I think you’ve kind of answered your own question here, honestly. Your new dude gets pegged regularly, and he enjoys it. Because he gets pleasure in this way on a fairly regular basis, his body is accustomed to relaxing and allowing anal penetration. He has been conditioned by pleasure to be open to the experience (pun completely intended). From what you’ve written, you haven’t had much anal activity in several years. Even though you have a cognitive memory of enjoying butt stuff, your body is no longer familiar with the ins and outs of anal sex (the jokes just write themselves, really). As a result, you tense up as someone approaches your bum, making penetration difficult and uncomfortable (as you recently discovered).

When it comes to anal penetration, you absolutely must have these two things: lubrication and communication! Lubing up is mandatory. Put some lube on that ish. Then put on some more! Not only does it make the experience quite pleasant, it drastically reduces the risk of minor injuries like micro-tears and fissures. Communication is key to a satisfying experience, for both of you! If you’re not comfortable giving your partner a lot of direction (stop, go slowly, that’s good, wait, push in now, hold still, etc.), you might want to enjoy other types of sexy times and skip anal penetration all together.

If you experience any difficulties during butt play, take the following three steps:

  1. Stop!
  2. Talk about what you were feeling.
  3. Add more lube.

Then you can feel free to continue, slowly. There is absolutely nothing to be gained by trying to do this quickly. If you’re in a rush, just skip anal for this encounter. You can try again when you’ve got time to really devote to the adventure.

It’s super important to keep the anatomy of the anus in mind when exploring the possibility of back door fun. As you enter the anus, there are actually two different sphincters. The first one that you encounter is controlled voluntarily. That means that you can think it into relaxing and opening. Wonderful! You’re past the first gate. The second sphincter is the tricky one. It responds involuntarily. You can’t just will it to open up. You have to be genuinely relaxed, be comfortable, feel safe, and be in secure physical position.

Some anal-specific foreplay can help open up that second sphincter. The outside of the anus (the wrinkly circle surrounding the actual opening that’s visible to the eye) has a lot of nerve-endings. A lot of folks experience a great deal of pleasure in having that outside part touched or kissed (remember your gloves and dental dams!). Playing with that sensitive tissue can be a great warm up for penetration. It can also be a lot of fun, even if you never want to be penetrated there.

It’s also a good idea to warm up the bum with small penetrative items. Start with a finger or two, or a small dildo or butt plug. See how that goes. If everybody has a very nice time, then next time you can consider using something larger, like a bigger dildo or butt-safe vibrator. You can continue increasing the size of the toy or appendage as you feel ready, or stop at any point. The most important thing is to enthusiastically enjoy yourself and your partner(s).

Curious about cunnilingus? Anxious about anal? Do you have questions about queefs or problems with your prostate? Lucky Tomaszek is the education coordinator at The Tool Shed: An Erotic Boutique, Milwaukee’s only mission-driven, education-focused sex toy store. Send her a question at mkesex@gmail.com and she’ll get back to you with an answer.