Every time I bottom, it hurts. I was told after a couple of times I would get used to it but I never have. I've also tried topping but I don't usually feel anything. Hooking-up just isn't enjoyable for me, no matter the position. 

- It Hurts

Dear It Hurts,

First of all, thank you for being brave enough to ask this question! It’s one that a lot of people find themselves asking, myself included. The first time I bottomed, I said to the guy “I’m just not sure I’m physically made to bottom”. In response, he laughed and told me that it always hurt the first few times and that I just needed to push through and do it more often for it to become pleasurable.

First off, that wasn’t a cool comment – we are all entitled to say no if it hurts, and it’s not ok to pressure anyone to doing anything they don't want to do or to belittle their experiences.

But secondly, it doesn’t always happen that way. For me, it did become pleasurable after a couple of times. But a lot of times it didn’t. And it wasn’t the smooth progression that was promised. It was really unpredictable, which only increased my anxiety and decreased the frequency at which I bottomed in the future.

There are lots of reasons why you might be feeling this way, many of which are really unique to each person. This makes it a little challenging to answer, but I will do my best!

To note:

• I’m writing this with an assumption that we’re talking about anal sex with a dick, but not all tops and bottoms have dicks. The same principles still apply to anyone having anal sex, regardless of gender identity and sexual orientation, however some of the terminology may differ (i.e. you could replace ‘dick’ with ‘dildo’ if this is more suitable).
• I've mainly focused on bottoming as this is more intensive, however there is a small part on topping further down. 

Sex doesn’t have to involve anal penetration

This is probably the most important thing I can tell you in your situation. When you have sex, you don’t have to stick anything up your butt. You also don’t have to stick anything up anyone’s else’s butt either. Penetration is not mandatory.

There are loads of other things you can do that are equally (or potentially even more) enjoyable than anal penetration. Oral, handjobs, rimming, teasing, edging, roleplay, fetish play, voyeurism, bondage – the world is your oyster!

A lot of people will tell you that these things are all great but don’t quite compare. Don’t listen to them! If penetration is their be all and end all, I promise you can do better.

Penetration doesn’t have to include dicks

That’s not to say that penetration is bad, either! If penetration is what you genuinely want, that’s great too, and it doesn’t need to involve a dick in any way, shape or form.

It can also involve:

• Mouths: Rimming can feel absolutely incredible – self-pleasuring while you’re being rimmed is a great alternative that can make you cum just as hard (though cumming is also not mandatory).
• Fingers: These are a great warm-up act but they can be just as good as the main event. Play around with your tempo, pressure, number of fingers, and don’t leave the prostate un-titilated. They’ll thank you for it, trust me...
• Toys: There are plenty of options when it comes to sex toys – shop around for one that suits you and your partner(s), and make sure to keep them clean after each use.
• Just the tip: Dicks can play a role without needing to be inserted all the way in. Let your partner’s dick slide across your bussy, or tease it with the tip and see how great it feels.

When it comes to comfortable bottoming, physiology isn't everything

In a perfect world, everyone would be able to bottom to their hearts content. Unfortunately, the world isn't perfect. There are lots of physical and psychological factors which impact how comfortable and relaxed you are when you have sex, and this plays a huge role in the pleasure (or displeasure) of the experience.

If you want to know more about butt anatomy, the San Francisco AIDS Foundation have a great resource to get you schooled up. But please remember that this is all super individual to you. At the end of the day, if bottoming hurts then you should never push through the pain - regardless of what you read or what anyone else tells you. 

Below, I've attempted to cover a lot of the common physical and psychological factors that come into play, and some good strategies for how to mitigate them.

Physical barriers to bottoming

• Fissures and haemorrhoids: The skin at the anus is sensitive and can be prone to anal fissures (small tears in the anus lining) and haemorrhoids (swollen and inflamed veins in the anus or rectum). These can bleed and cause pain or discomfort. If bottoming is uncomfortable, you might risk causing fissures or haemorrhoids or you might be agitating existing ones that haven't healed. If pain or discomfort persists, it’s worth speaking to a medical professional; you can book free, confidential services at Family Planning or Central Auckland Sexual Health Clinic if you’re not comfortable talking to your own GP.
• What lube you’re using, and how much: It's important to use as much lube as possible - you can never use too much! There are also lots of different types of lubes that can be used in different settings and for different preferences - it’s hard to go wrong with water or silicone-based lubes, but I know everyone has their own preferences, so do use what feels best for you. 
• Your top’s performance: The way the top is fucking you has a massive impact on how much you enjoy it. Are they gentle and attentive? Rough and aggressive? A combination of the two? Are they fucking you fast or slow, or mixing up their pace? This all makes a difference. If it hurts, stop, pause and communicate with your partner(s) to see if you can find more ease and comfort.
• Warming up: Are they starting things with touching, rimming and/or oral first, or are they going straight for your hole? You want to be as comfortable as possible during sex, so don't be afraid to demand as much warm up as you need. Remember: If it starts to hurt, you don't have to keep going. You can stop at any time.  

NB: Penis size is often thought to be a significant barrier to pleasurable anal sex. However, how the top is using their dick, how much lube they’re using, and how warmed up you are are all more important factors that can make dicks of any size feel amazing. 

Psychological barriers to bottoming

• Worrying about the pain: If you’re already worried that it will hurt, it’s much more likely to become a self-fulfilling prophecy. Once you find yourself in a mental spiral, I recommend stopping and waiting for a time when you’re less anxious – pushing through rarely achieves what you want.
• Emotional and physical connection to your partner(s): The way you feel about the person(s) fucking you has a big influence on how comfortable and relaxed you are. And if you’re relaxed, it’s much more likely that your external sphinchter is relaxed as well. Be honest about how you’re feeling; do you really want to be having sex with them in that moment? Or are they pressuring you in any way?
• Libido fluctuations: Sometimes, you may be going through a phase where you just don’t feel like having sex with anyone. This might happen for no good reason, or could be to do with stresses in other parts of your life. This is totally normal, and having sex when you’re not in the mood won’t do anything to increase your pleasure.
• Anxiety around unsafe sex: Having unsafe sex can make you anxious, even if you don't realise it - and rightfully so! Due to the sensitivity of the area, painful sex can be a sign that you're putting yourself at a higher risk of contracting HIV or other STIs. Using condoms or other effective HIV prevention methods such as PrEP are a great way to keep you and your partner(s) safe, and also reduce your anxiety.
• Poo anxiety: Sometimes, shit happens. This is a totally normal part of anal sex, and can happen whether you’re douched to an inch of your life, or if you’re having sex completely unplanned. However, knowing this and not letting it impact your sex life are two different things. Anxiety around poo, especially as a bottom, can impact how comfortable and relaxed we are whether we realise it or not. When we’re not relaxed and uncomfortable, our sphinchter can pucker up and make sex painful.

What about topping?

You mentioned that you don’t get any enjoyment out of topping either. That’s also totally ok! While topping may not be as physically intensive as bottoming, some people just aren’t into it. We don’t really know why; sexual preferences are notoriously difficult to analyse.

I refer you back to Part 1 and Part 2 of this article, because these principles apply to not wanting to top just as much as not wanting to bottom.

But if you want to top, but just can't feel much, you could try:

• Add a drop of lube to the tip of the condom - this will allow a little more friction over your penis head, which may feel more pleasurable
• If you're circumcised, try keeping the tip of your penis moisturised throughout the day, and see if this helps. You may also want to look into foreskin restoration - this is a lengthy process but common feedback is that it helps increase penis sensitivity

I hope that answers your question!

A few things to remember:

• You don’t have to have anal sex if you don’t want to. Plenty of people have very fulfilling sex lives without penetration.
• You deserve partners who understand and respect your preferences.
• Sex can be just as pleasurable without dicks, and/or without full anal penetration.
• If you do want to have anal sex, have a think about what else might be going on that might be making you anxious or tense.
• If you’re feeling anxious or tense, your sphinchter will also feel that way, and that’s not going to result in a pleasurable experience.
• Always practice safe sex with your preferred prevention method (such as condoms, or PrEP).

Good luck It Hurts, I wish you all the best in your future sexual endeavours!