Done right, it simply shouldn’t hurt. You just need to start small and slowly enough, warming up to the point over time where you can have actual anal intercourse.
- Start with external massage of the anus with a lubricated finger, letting yourself relax as the finger circles and rubs across the opening.
- As you feel yourself starting to relax and open slightly, gently slide the finger inside. Penetrate in short, shallow, gentle strokes initially, allowing yourself to get used to the sensation if it starts feeling intense. If it hurts, back up and start over with massage for a little bit first, repeating as needed.
- As you’re totally comfortable with one finger, try adding a second. Keep repeating this process of gradual increases in size until you can fit three or more fingers.
- Start adding a toy into the process, ideally a dildo for this purpose, but butt plugs are also useful and can be used as part of longer term “training” for anal sex over time, as well as more of a shortcut to warmup prior to sex in the future.
- Keep going up in size with toys until you reach or slightly exceed the size of your partner’s penis and can comfortably fit that size. You’re now ready to have anal sex.
- For initial penetration with a partner, go through any necessary warmup beforehand as above, then when they penetrate, communicate and pause anytime something hurts and let yourself relax and adjust, then continue. When fully inside, pause again and get used to it, then start building up to slow strokes and increase in speed and depth as you get comfortable to it.
- If anything hurts, stop and reassess. You may need to slow down, not go as deep, or stop entirely for now. With practice you can do more, but you shouldn’t “push past the pain”. If it hurts, you aren’t warmed up/relaxed enough, or aren’t using enough lube, simple as that. And sometimes you just hit your limit when you’re starting out and need to try again in a few days.
- Practice! The more you do it, the easier it will get, and it won’t hurt at all once it becomes a regular thing. The biggest long-term factor for anal discomfort or pain that keeps people from doing it more regularly is the fact that they aren’t doing it regularly and so don’t stay in “anal shape”, as it were, requiring a lot more warmup and preparation. Couples who have anal sex several times a week or more just get complete enjoyment out of it, no pain or discomfort. This is also a big factor when a couple goes anal only.