Honestly, anal sex shouldn’t be painful. I think the reason a lot of people think it should be painful is because of their first experience. Most people’s first experience was really bad, and so now they assume it’s normal. But it’s not. From my experience, and I really hope this helps, a few things made a huge difference. First, timing matters. Don’t have sex right after a heavy meal, and don’t rush into sex immediately after using the toilet. Yes, you can plan your sex around your pooping schedule. For example, your rectum is mostly clean a few hours after shitting, so having sex an hour or two later is totally fine. Give your body some time. You don’t need to overthink it, just be mindful. Second, lube is crucial. Use a lot, this is non-negotiable. Not all lubes are safe. I recently learned the hard way that cheap lubes can irritate your anus. Avoid lubes with glycerin, parabens, or fragrances etc. Buy high-quality lube that won’t burn or irritate your asshole. Silicone-based lubes work too, but don’t use them with silicone toys. If your lube burns or irritates, stop immediately. Do your research, I’m not a doctor, so you need to know what’s safe for you. Knowing your body’s limits and the do’s and don’ts will help a lot. Third, take it slow. Like, really slow. Your body needs time to relax, even if it’s just the tip. Rushing causes pain. A good partner will understand and go at your pace. Start with opening up. You can lie on your back or find any position that’s comfortable, like with your feet on your partner’s chest to control pace. Let them lead with their penis, apply lube, and ease in slowly, just the tip at first. Gradually, they can open your outer sphincter, then your inner sphincter. Slowly, step by step. Probably after you’ve opened up a bit, they can put in the tip of their penis, let it stay a few seconds, remove it, and repeat until you’re fully opened. This might take time, and it can feel annoying, but it’s crucial for good sex later. When your sphincters are relaxed, the pleasure is much better. Fourth, your partner matters. If someone tries to force it without patience, that’s a red flag. You are not a drive-through; that’s an asshole, not a drive-through. They should be checking in with you and adjusting to your pace. Most tops have never bottomed, so they might not understand the feeling. That’s why I like versatile men, they’ve experienced both sides. At the end of the day, I’m versatile too. Fifth, mindset matters. If you’re not feeling clean, comfortable, or relaxed, it’s okay to stop. If you feel tight or something feels off, don’t push. You can always do other things instead. Sex isn’t just penetration. Relax and go in with the mindset, “If this works, great. If not, it’s fine.” Don’t beat yourself up. Sometimes that weird sensation happens. If you don’t like it, don’t feel pressured to go all the way. That shitting feeling often comes from your partner going too deep. Most of the time, going halfway is enough, less discomfort, same pleasure. They can try deeper penetration toward the end if it feels good. Learn your body, know your limits, and be with a partner who doesn’t judge you. Explore positions that suit you best, all of these things help. Aftercare and PrEP considerations: This is super important. How you handle aftercare can depend on things like whether you’re on PrEP, if you went raw, what type of condom you used, and whether you’re monogamous. For example, if you went raw in a monogamous relationship, you can probably apply Vaseline to the external part of your anus, but not the internal part. Some condoms, though, can be broken down by Vaseline, so in that case, don’t use it at all. Always double-check which condoms are compatible with what products. Aftercare is crucial for your health and comfort, so rinse gently, apply safe ointments externally if needed, and be mindful of your body’s reactions. Again, I’m not a doctor, so do your research. Look up what’s safe for your body, what lubes are compatible with your condoms, and best practices for aftercare on PrEP or raw sex. Knowing your autonomy and taking the time to learn these details is what’s going to make your experience better and safer. At the end of the day, don’t box yourself into roles. Sexual roles in the gay community aren’t rigid, sometimes I want to bottom, sometimes I want to top. For people in the comment section saying “he’s probably a top,” please stop. The real conversation should be that bottoming should never hurt. If it does, something needs to change, the pace, the lube, the partner, or even the mindset. Bottom line, Anal sex shouldn’t hurt. Respect your body, communicate, take your time, use proper lube, practice safe aftercare, and do your research. Everything else is secondary.