Painful Anal Sex

I’ve been seeing a really hot guy for a few months now and we’ve totally dived straight into a relationship. I know that we both want it to be a long term thing and I really feel that it will be.  We have really great hot sex and are totally compatible. We’re both versatile and he seems to like taking turns at either role as much as I do. The only problem is when he fucks me it often ends up really hurting and I can’t help reacting – which just kills things. Everything is usually fine until just before he comes, when he pushes too deep and hard, which hurts too much and I can’t hide that it does. We’ve talked about it and he’s promised to be more careful, but it still keeps happening. He says he gets carried away and caught up in the moment of wanting to come, and that’s when he thrusts really hard. While I totally understand that he can get carried away during sex, the fact it always ends up hurting means I really don’t like being fucked by him. And its made worse because even when its not hurting I get tense because I keep anticipating the moment when it will. Lately I find that I’ve been trying to avoid letting him fuck me but I know that this can’t last. I really want it to work with this guy, so I’d really appreciate any advice you can give.

Gavin. Melbourne

Dear Gavin,

Your dilemma does sound troubling and not uncommon for people of all genders who are engaging in anal sex. Firstly, it sounds like you have a great relationship with him and this is a fantastic aspect to working with a situation like this. Painful sex is usually caused by the same few things

  1. Not being warmed up enough
  2. Not enough lube
  3. Being tense

You mentioned that even though you have discussed it with him, he gets carried away and forgets your feelings. This would be fine if it didn’t bother you, but it does! First and foremost, you have to explain to him ( again) that this kind of sex is unpleasant and is actually painful  for you. As you say, it’s fine until up to the end where it starts to hurt. Explore other ways of helping him cum, as intercourse is not the only form of sex available. You can extend the pleasure if he  pulls out and you extend his arousal using your hand or mouth (a safer sex warning here; anal to mouth can have bacterial consequences for you, so be conscious of the risks involved from ingesting fecal matter. Also if you’re not fluid bonded {i.e. have regular STI tests and know each other’s status} condoms and hand relief are advised).


If you feel the need to work on your capacity as an anal receiver, I suggest you practice slowly. Make sure you’re using enough (LOTS) of lube. There are a lot of great lubes around  made especially for anal sex, they are thicker and more viscose than regular lubes. Avoid tensing up by breathing deep into your abdomen and bearing down with the anal muscles. This helps relax the whole area. Alternatively experiment with different positions, as some positions are more painful than others depending upon your internal anatomy. Try lying flat on your stomach, on your back or on your side!

Also never assume that great sex is always just about intercourse, or always about cumming. Rule of thumb though;  if any sex hurts too much and in a way that you don’t like, STOP! It’s your body’s way of telling you something is wrong. If you continue to experience pain with penetration, you might consider making an appointment with me face-to-face or via Skype to  get a better understanding of your problem and work toward some solutions.  Never EVER use numbing agents. They stop you from feeling anything at all, and that is the LAST thing to do when you’re having sex! Serious damage can occur when you can’t feel anything and must be avoided.

Respect your body and it will respect you back.

With Pleasure