The Frisky Feminist

From OOH to OUCH: “Why Does Anal Sex Hurt Now?”

Q: When my boyfriend and I first got together, he was very interested in trying anal sex. It took a couple of months of convincing, but I finally agreed to try it. I quickly found that I loved it. It consistently gave me some of the most intense orgasms I’d ever had. And for a few years everything was good.

Then we went through a rough patch where we weren’t really having sex at all. Though we’re mostly back on track now, it seems that anal sex has become a thing of the past for us. It’s downright painful now, and not in the good way. Even anal stimulation is proving uncomfortable. We’ve tried a number of things (more lube, less lube, finger first, making sure he trims and files his nails before doing the finger first, using a butt plug before the penis), but nothing seems to be working.

Do you know if this is common? Is it something that will take more time, or more attempts? Or is it possible that I’ve simply outgrown enjoying anal sex? I’d hate for that to be the case because, as I said, it gave me some of the best orgasms of my life. But now it’s just a constant source of frustration. Do you have any advice or encouraging words? – Frustrated

A: First of all, this is unrelated – we love that all you question-askers have started giving yourselves noms de plume! We had tossed around the idea of giving people fake names when we first started the column and we like that you guys have just started doing it.

Now, onto important matters – your ass. You gave a really great rundown of ways to ease into anal sex, and you’ve definitely tried some of the things that would be at the top of our list of suggestions. So we’re going to throw out some more ideas and possibilities, and hopefully we can help you figure out what’s going on and what you might be able to do to get back to all that awesome anal sex you enjoyed before.

How frequently are you and your boyfriend engaging in anal activities (with you receiving)? If you’ve been trying to make it happen really frequently, it might be worthwhile to give it a rest for a bit to let any irritation subside.

Have you tried other kinds of lubes? Both of us have pretty strong preferences when it comes to lube for anal sex; we both find silicone lube far more comfortable and it helps things go much more smoothly for the both of us. If you’ve been using water-based lube, it might be worth trying silicone, or vice versa, especially if you’re feeling any burning sensations and that’s contributing to the overall pain you’re experiencing.

Now, poo. Has anything changed poo-wise lately? Do you have any pain or bleeding during a bowel movement? If so, an anal fissure is a possibility. (Don’t worry, it sounds much worse than it actually is.) An anal fissure is a tiny tear in the skin lining your anus, and while it’s small, it can cause a lot of pain and can sometimes result in spasms of the anal opening, which could certainly inhibit pleasurable anal penetration. Along the same lines, do you think a hemorrhoid might be a possibility? Hemorrhoids can be very tender and are prone to bleeding as well. So, if there’s ever any blood during your anal attempts, or when you poo, one of these things might be the culprit. (If you think this might be it, you can find some info about speeding along the healing process here.)

Have you and your boyfriend tried penetration in different positions? Changing the angle could be helpful, and positions like doggy style or you lying on your stomach could put less pressure on your ass. And have you tried penetrating yourself, either with your finger or a toy, and if so, does it feel the same way? Does it hurt when you’re using the butt plug too, or just when something is moving around up in there?

When your boyfriend is fingering your ass (or if your fingers are long enough that you can really feel what’s going on), pay attention to what the muscles are doing. Is he able to move his finger somewhat easily as the muscles sort of open up to accommodate it, or are the muscles really tight and tense and closed up? Have him stop with his finger inside you as far as it will comfortably go before hitting that tensed-up muscle and take a moment to breathe in and then exhale, and see if the muscles relax a bit. Repeat, and repeat (unless things are really hurty – listen to your body). You may just need to take things much more slowly now, for whatever reason, and taking a lot of time to focus on feeling as relaxed as possible could help ease the discomfort. (When we first started enjoying pegging, it wasn’t uncommon for paperispatient to spend 20-30 minutes on slow fingering before moving on to the dildo.)

Also, if you can, try to pay attention to how you’re feeling emotionally and mentally during all of this. If you’re feeling frustrated or if you’re tense and anticipating pain, that can have a huge impact on how the stimulation feels. It makes sense, really – if something has hurt before and that something is about to happen again, we bet that most people would be a little wary and not 100% relaxed. If you find yourself feeling this way, spend some time on other things for a while, whether that’s other kinds of sex or massage or just cuddling. We know it’s much easier said than done, especially when something has been so amazing in the past and seems to be the complete opposite now, but try not to put pressure on yourself to make it happen. If you’re feeling constantly frustrated, take a break from trying for a while and try again when you’re feeling better.

Persephoneers, is there anything we’ve missed? If there are any other anal sex aficionados out there, what have you found that makes things feel good and not hurty?


Keep the great ques­tions com­ing! (Hee.) Got a ques­tion to ask, sub­ject you’d like us to dis­cuss, or myth you’d like us to bust? You can e-mail us at or send us an anony­mous mes­sage via the spiffy, new Ask Us! fea­ture here.

By paperispatient

I recently earned my MA in women’s studies. I enjoy reading, working out, playing Scrabble, watching cheesy movies, and cooking yummy vegetarian meals with my partner and Frisky Feminist co-author, Future Mr. paperispatient.

2 replies on “From OOH to OUCH: “Why Does Anal Sex Hurt Now?””

There is definitely a use it or lose it aspect to anal sex for me. If my bf and I do it for a bit then stop and try to pick it back up like a few months later it hurts and we have start the process all over. You anticipating the pain is the biggest hurdle to overcome. I have to consciously relax my body.

The biggest thing that I have ever found that helps when its difficult to penetrate is that while he is slowly easing himself in he rubs my clit. The sensation of clit rubbing can over power the sensation of being penetrated. Concentrate on that. I also find that since I enjoy having that rubbed my body relaxes a lot more.

Leave a Reply