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📘 Part of: How to Prep for Anal: The Complete Guide
"If bottoming hurts, then stop. Perhaps it's uncomfortable, but it should never hurt." — a commenter on r/askgaybros, 2025
That's the whole thing in one line. Pressure and a stretch are normal. Sharp, burning, make-you-flinch pain is not, and it's almost always fixable. Here's how to make bottoming stop hurting, without just gritting your teeth through it.
60-Second Answer
If anal hurts, you don't need a higher pain tolerance. You need four things, in this order:
- Relax the right muscle. The pain is usually the inner ring clenching. You can't force it open, you have to let it open.
- Go slow enough that it's almost boring. Most pain is a top moving faster than your body has caught up to.
- Use more lube than feels necessary, and the right kind. Friction is pain. Reapply often.
- Prep on the calm days, not in the moment. A hole that's been gently worked up over weeks doesn't fight you.
Get those four right and the pain mostly disappears. The rest of this is the why, plus the one lube-and-condom rule worth knowing.
Why it hurts in the first place
Your anus has two rings of muscle. The outer one you control, you can clench and release it on command. The inner one you can't. It's involuntary, and it answers to your nervous system, not your willpower. When you're tense, anxious, or bracing for pain, that inner ring grips down. Then something pushes against a closed door, and that's the pain.
Cleveland Clinic puts the mechanism plainly: "Trauma — like stretching and straining — causes your anal lining to tear." And on why tension makes it worse: "If these muscles are too tight, they can add tension to your anal lining, making it easier to tear and even reducing blood flow to the tissues." So a clenched, dry entry isn't just uncomfortable. It's the exact setup for a small tear, which then hurts more, which makes you clench harder. That loop is what turns one bad time into a fear of the next one.
A guy on r/askgaybros described the feeling exactly: "It's that inner ring that hurts when I try to get past it with anything bigger than one finger." That's not a you-problem. That's the default, until you teach the ring to let go.
How to relax for anal sex (the actual mechanic)
"Just relax" is useless advice on its own, because nobody tells you how. Here's the part that works.
The trick almost everyone who's figured this out repeats: instead of pulling in, bear down slightly, like you're gently pushing out. It sounds backwards. It opens the ring. One commenter put it more bluntly than we would: "the easiest way to take a cock… is to bear down like you're taking a shit. That relaxes your hole." Crude, correct. Another tested check from the same community: "If you feel like your asshole is still trying to push out a turd then you're not relaxed."
Stack breathing on top. Long exhale on the insertion, not a held breath. Tension lives in a held breath. And handle the anxiety, because anxiety is the clench. If fingers alone hurt, that's usually nerves, not anatomy. A bit of warm-up, a calm setting, a partner who isn't rushing you, all of it drops the baseline tension before anything goes near you.
Go slower than feels reasonable
The single most common cause of pain isn't size. It's speed.
The top thinks "I'm in, let's go." Your body is still catching up. On that same "Anal hurts" thread, the top reply nailed both halves: "there's two problems when anal hurts… the top sucks, and is going way too fast." Another spelled out the pace: it can take "30 minutes of him just being inside you, slowly in and out, before he can actually speed up."
Slow isn't a courtesy. It's the mechanism. Each minute of gentle movement lets the inner ring give a little more. Rush it and you're back to pushing on a closed door. If you're newer to this, riding on top is the cheat code, you control the depth and the speed, so nothing happens faster than your body allows. "Stop the second it goes from pressure to pain" is a rule, not a mood-killer.
Use real lube, and a lot of it
Friction is pain. There's no clever workaround, you just need enough lube, and you need to reapply, because the body absorbs it and it dries out faster than you'd think. "Use lots of lube" is the most-repeated fix in every one of these threads for a reason.
Now the part people actually ask about. A lot of guys reach for a thick, natural option like shea butter, and it works as a rich, long-lasting glide. There's one rule that matters and it's non-negotiable: don't pair an oil with a latex condom. The CDC is direct about why: "Oil-based lubricants (petroleum jelly, body lotions, etc.) can weaken latex and break the condom." Their flat recommendation when latex is involved: "Use water-based lubricants." So if there's a latex condom in the picture, go water-based. No latex condom in the picture, and a thicker natural glide is a comfortable, fragrance-free option a lot of people prefer.
Our raw, unrefined shea butter is a single ingredient, organic, nothing added that sensitive skin has to react to. Just keep the latex rule in mind.
"But isn't anal supposed to hurt a little?"
This is the real fight in the community, and it's worth having. On one thread, somebody insisted: "The biological reality is it's going to almost always hurt a bit and that's part of the pleasure." Someone else pushed straight back: "no it shouldn't hurt. If it feels a bit uncomfortable or perhaps 'awkward' sure… But it shouldn't flat out hurt."
Here's where we land. There's a difference between a stretch and pain. The first time something stretches the ring, you feel intense pressure, full, a little overwhelming. That's the stretch sensation, and it fades in under a minute as the muscle gives. That's normal. Sharp, hot, cutting pain that gets worse the longer it goes, that's your body telling you something's wrong, almost always tension, speed, or not enough lube. Don't power through that one. Pain isn't proof you're doing it right. It's information.
So both camps are half-right. A new stretch can feel like a lot. It should not hurt. If it does, you change something, you don't tough it out.
Prep on the calm days, not in the moment
You can't fix all of this in the ten minutes before. The biggest lever is what you do on the boring days in between.
A hole that's been gently and regularly worked up, fingers, then a small plug, over weeks, simply doesn't fight you the way a cold start does. As one commenter put it, bottoming "only hurts on the initial insertion if I'm not stretched enough already." If even a finger feels like a lot right now, that's the place to start, not the bedroom with someone waiting. We broke the whole progression down in how to anal stretch the right way, slow, no tearing, the version that actually works. If this is genuinely your first time, our first-time bottoming guide covers the nerves and the setup too.
The other half of calm-day prep is what's going through you. A predictable, well-formed bowel means less straining and less to clench against, and that comes down to daily fiber and what you eat in the day or two before. We cover the eating side in the bottom diet guide, and a daily soluble-fiber habit like Colon Gentle Cleanse psyllium sachets is the simplest way to make that baseline boring and regular.
The pattern is the same as the rest of this article: do the calm-day work, and the in-the-moment part stops being a gamble.
When to stop and see someone
Most anal pain is mechanical and fixable. Some isn't, and a forum can't tell the difference. See a doctor, not a thread, if you get any of these, per the NHS:
- Bright red blood in the toilet or on the paper
- Sharp, burning pain that lasts hours after, not just during
- Pain that doesn't settle after a week of being careful
- Any tear or cut that keeps reopening
A small fissure is common and usually heals on its own with gentle care. But "it always hurts and it isn't getting better" is worth getting looked at, not living with. And if you already have a fissure, hemorrhoids, or an upset stomach, that's a day to skip play entirely rather than push through, we cover the full list in when you should not prep.
The honest bottom line
Anal pain isn't a tolerance problem you white-knuckle through. It's a signal, and the signal almost always points at one of four things: a clenched inner ring, too much speed, too little lube, or not enough prep beforehand.
Three things to take with you:
- Relax by bearing down and breathing out, not by tensing up and hoping.
- Slow enough to be boring is the right speed. Stop the moment pressure turns to pain.
- Do the prep on calm days so the moment itself isn't where you're starting from zero.
Get those right and the question stops being "how do I survive this" and starts being "why was I ever scared of it."
The glide, and the after
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Related reading:
Disclaimer: This is general information for adults, not medical advice. If you have bleeding, sharp pain that lasts after sex, a tear that keeps reopening, or pain that won't settle after a week of careful care, talk to a doctor. Pain is information worth getting checked, not toughing out.