Message: Excited to Try Anal, Afraid Something Will Go Wrong

Anonymous: I’m very excited to do anal for the first time and I’m going to do it with a friend, but I’m afraid something will go wrong if you understand what I mean. Do you have any advice for me?

You could mean several things, so I’ll answer generally.

If you’re afraid of a mess, make sure to go the bathroom in advance. If you’re really concerned, use a douche/enema bulb to squirt just a small squeeze of warm water into your rectum and push it out, repeating a few times. That should be all you need to do. You can check by inserting or masturbating with a dildo beforehand to see if your rectum is clean.

If you’re afraid it’s going to hurt, you should practice/train with fingers and toys before trying it with a partner, so you know what to expect and prepare your ass for penetration without pain. Some people can dive straight into anal sex without preparation, but most people need to practice a little first. Try it on your own time with a lubricated finger at first, and work up to a dildo.

When trying it with a partner for the first time, make sure to lubricate both his penis and your anus, and do it in such a way that you can control the initial penetration speed, angle and depth. If it starts to hurt, just pause at that position or back off slightly until any pain fades, then continue until he’s all the way in. If you need to pause a moment again to adjust to having him inside you, do so, then start slowly moving and let him take more control as you get comfortable with it. Don’t hesitate to pause again if something starts to hurt.

Combining anal penetration with clitoral stimulation can help a lot when you’re first starting out, both to relax you and to help start interpreting anal penetration as something pleasurable. It’s not necessary for everyone, but if you have difficulty with anal, give it a try.

Good luck and enjoy!

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