Message: Advice for an Anal Virgin

Anonymous: I’m a 30 yr old anal virgin, once with a guy who ruined anal for me. I think that I am missing something exciting. What/how would you recommend that I could get into it with out the pain I associate with it. Thank for any suggestions Anally deprived !

Because you associate pain with anal penetration, you’ll likely (unintentionally) tense up in that area when attempting anything, when you really need to be relaxing the area instead. Fortunately, there are a lot of ways you can relax and help start to enjoy anal stimulation.

I’d definitely do experimentation on your own rather than with someone originally, so there’s no pressure and you can go entirely at your own pace. Start out by taking a hot bath or shower, and then ideally masturbate to one or more orgasms until you feel very relaxed. Then, slowly (with lube) rub a finger around the outside of your anus (without any penetration). You can couple this with vaginal/clitoral stimulation. Consider just doing this external stimulation for a while. The anus has a lot of nerve endings, and even with no penetration can be quite pleasurable when stimulated, especially in combination with other stimulation.

When you’re comfortable doing that and do not associate external stimulation of the anus with pain or discomfort (this could be immediate or could take days or weeks—each person is different) you can move on to very gently inserting a lubed finger (or finger-width toy) inside. Everyone’s anus can safely fit a lubed finger with no problem, even with no prior experience—the difficulty some people have with pain or difficulty penetrating is that they are not relaxed enough to temporarily loosen the area. As you gain experience with anal penetration, you also gain muscle control that can make it possible to relax the anus at will to make penetration nearly effortless.

Some people have an early issue with anal penetration where they feel as though they need to go to the bathroom due to the presence of an object in their rectum. This doesn’t happen to everyone, but for those it does happen to, it’s normal—your body hasn’t yet figured out the difference between anal penetration for pleasure and the presence of waste material. If it does happen to you, just keep trying and frequently combine the anal penetration with vaginal/clitoral stimulation and you’ll be able to enjoy anal penetration without that feeling.

Over time, you can increase the size of penetration from one finger to two or three or more. You should always be very gentle and take things slowly when increasing the size of object penetrating for the first time. There should never be any pain—if something hurts, you’re taking things too quickly and aren’t relaxed enough. Stop what you’re doing immediately and rest a few minutes before trying again more slowly or with more warmup with smaller objects. Pushing out/bearing down, as if you were going to the bathroom, can help to relax your anal muscles during penetration.

If, after experimenting with your fingers, you find you enjoy it and wish to continue with anal experimentation, consider investing in a butt plug. There are a lot of options, and silicone, glass and stainless steel ones are usually the best. There are also a lot of sizes, and it can be tricky to pick out a good size early on because you want one you can fit without having one that will soon become too small to enjoy as your anal abilities grow. Butt plugs are great because you can put them in and they stay in place while you masturbate or have vaginal sex. Some people enjoy the feeling so much that they leave them in for longer periods of time, even when working around the house or going out in public.

Before attempting actual anal sex with another person, you should have worked up to being able to comfortably fit a dildo the size of their penis. When you do first attempt anal sex with another person, you should be on top and in control of the speed and angle of penetration so you can slow down or stop in case anything goes too fast or hurts in any way.

Essentially, the key elements in overcoming anal fear and pain are to learn to relax your anal muscles and to associate anal stimulation with pleasure by always coupling it with something that you already find pleasurable.

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