Message: Really Want to Do Anal, But Too Painful

Anonymous: Me and my boyfriend really wanna do anal, but for some reason whenever we try it’s too painful and it doesn’t work… However, not long ago, we were able to do anal very briefly without any pain or discomfort without lube or training… We have training butt plugs and “booty relax” lube but nothing seems to work… I don’t like the feeling of fingers in my bum unless I’m wearing gloves :/

I really don’t recommend any of the so-called “relaxing” lubes—they generally are masking pain, and pain is an important sign during anal. It tells you you’re going too fast, too big, too soon and should stop before you injure yourself.

Sometimes everything just happens to be just right and people who haven’t prepared for it can have anal without any pain, but that is not the norm.

Is the dislike of fingers due to roughness of skin/sharpness of nails? Gloves can be a perfectly suitable solution in those cases, especially if you don’t want to trim nails. It’s also possible for sweat from your fingers to cause a slight burning sensation, so you always want to wash beforehand.

Essentially, if it hurts when you try anal intercourse, you either aren’t ready to consistently have it yet or you haven’t warmed up enough for it in that particular session. If it’s the former, you’ll need to keep working up in size with toys.

If the latter—which is possible since you have been able to have anal once without pain—you may need to expand your anal foreplay/warmup sessions. Play with your clit throughout all of this, using fingers or a vibrator—whatever works best for you. Start with your boyfriend rubbing your anus externally with the pad of his thumb. If both of you are into it, having him rim you is an excellent starting point to help you relax. Shift into him either inserting a lubricated finger or small toy and gently moving it in and out as either he or you play with your pussy and clit. After a few minutes, try a second finger or the next size up toy. Keep going through this process. If it gets to a point where it’s painful, back off to the previous size for a few minutes before trying again.

Using this process, you should be able to work right up to the size of his penis, at which point penetration by that should be no more painful than anything else. If it is, then the last size toy you were able to work up to probably wasn’t close enough in size to his penis and you may need another step in between sizes.

To aid penetration, “push out” as if going to the bathroom at the same time to help relax your anal sphincter muscles. They work differently from most of our muscles, in that they’re clenched shut tightly when relaxed and loosen when flexed. The more practice you have, the easier that gets to do, and it can really help. You can also try alternating between pushing out and relaxing as he gently pushes in—it feels great for him, and it sort of “sucks” him into you.

You may wish to start out in a position where you control depth and angle, e.g. you on top sitting down onto him. Whatever the position, once he gets fully inside you, you should stop and just remain there for a moment (continuing to play with your clit) as you relax around him and then slowly start moving.

It’ll probably take a few tries, and possibly more training/warmup processes as needed, but you can definitely get there. Just remember that, especially when starting out, you’ll need to go through warmup/foreplay before every time you have sex, and if anything hurts, stop immediately and go back to a smaller size until the pain fades and you can try again. Never try to push through the pain, it’s not worth it and can result in an injury, which is no fun for anyone. Pain just means “back off a minute, I’m not ready for that just yet!”

Good luck, and I hope you have lots of awesome pain-free anal in your future.

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