The Joy of Pegging, Part 1

Read Part 2 (but you should really read this part first)

Dear God, dear God, How I love to peg. I sometimes feel like God made me to peg. In case you don’t know what pegging means, it is the act of a woman putting on a dildo or other appendage and fucking a man in the ass with said appendage.

We owe the term itself to the great Dan Savage. And his fans. We also owe the redefinition of santorum to this great mind and oh, joy!

Why peg?

So many reasons to take it in the ass. First, it feels really good. Second, why should the woman always be the party being penetrated? Third, it can enhance a dominant/submissive (D/s) dynamic in a relationship. Fourth, it feels really good (did I already say that?). And in some cases, it can bring you closer together. To be pegged requires a lot of trust on the part of the submissive, and can be a new experience for him as he submits.

(If you’d like to be immersed in this experience, you should book some time with me.)

Clearing up a few misconceptions

First, let’s clear up a few misconceptions. Because, as with many things about the butt, it is dark and mysterious. It’s not, but you know, people get freaked out when you’re talking about that area.

Misconception 1: Wanting to be pegged means that you might be gay. Nope, nope, noooope. It does not mean this at all. It means that you find it pleasurable to have something put into your ass. Which means you are a human. The anus has a number of nerve endings and just playing with the outside is a lot of fun. Also, this assumption is somewhat homophobic, as there are a number of gay men who do not engage in anal sex. (At least the ones I know.) It cannot turn you gay or anything of the sort. Please do not think this, as the anxiety of it will just interfere with your fun. And if you’re questioning your sexuality, I say still have fun with it.

Misconception 2: It will hurt. OK, OK. It can hurt but if it does, that is a sign that you are doing it wrong. If you are taking your time, lubing up and really really enjoying the process, it will not hurt. Even if you have a pain fetish, this is not the place to endure it.

Misconception 3: That you can go straight to big dildos. No, no, no. Do not do this to your delicate ass. The rectum is delicate tissue, and you wouldn’t want to tear it, because that can lead to all kinds of bad outcomes (sepsis, anyone?). You need to work your way up, which is something I cover in the next section.

Misconception 4: That you can use any old thing and stick it in your ass. No, no, no no, no. You do not want to end up in the emergency room explaining why there is a carrot or a lightbulb or a wooden dowel in your ass. (Unless you have a medical fetish and even then, it’s better to use a butt plug and just play pretend.) Butt plugs are shaped with a flared base for a reason: so they don’t get lost in your rectum. Again: the rectum is a delicate area and you should treat it accordingly.

Misconception 5: That it will be messy. Like the community swimming pool, if you’re having active diarrhea, you may want to postpone your pegging session. But if you’re eliminating just fine, are showered and ready, then have at it. That said, you will likely want to use gloves on your hands and condoms over your toys just for easy clean-up.

Training your ass

Ass training is a vital part of enjoying pegging. After all, you want to get to that wonderful place of prostate stimulation and deep subspace, don’t you? Ass training is sort of like gauging your earlobes: you train your body to take larger objects. Although, unlike gauging, your anus goes back to its original size generally speaking, because it is governed by two sphincters or muscle rings. The outer sphincter is under your voluntary control and the inner one is governed by your nervous system. So if you’re bearing down, you’re using your outer sphincter. Ass training is all about that inner sphincter and getting it to relax to be able to take things into your rectum.

And for you single men out there: this is something you can indeed do on your own. So that when you’re lucky enough to meet a dominant woman, you can bend over, point your ass at her, and tell her where to take you. Just kidding. Unless she has this sense of humor (like me) she will probably not think that’s very sexy.

First, start with your fingers and a lot of lube. The lube you want to use is a little thicker than the lube used for penetrative vaginal sex. Sliquid is a brand I prefer and have used for a few years. The one I like for anal sex has the green label. Use nitrile gloves just in case you have a latex allergy.

For your first training session, make sure you have a bit of time. You do not want to rush yourself, since ass training is all about relaxing your entire body.

If you are not that flexible, you may want to start with a very small toy. Again, make sure that it has a flared base to ensure it does not get stuck. Buy the smallest toy that you can find. And make sure that it’s made of silicone, because this is easy to sterilize. You do not want toys made of that plasticy jelly-like substance (I don’t know its name) because it’s impossible to sterilize and over time it breaks down into a disgusting mess. There are a number of training kits that have graduated butt plug sizes (small, medium, large) that will help you train your ass to take your first dildo from a mistress. They are pretty affordable and can prove to be fun to use even when you’re not training.

OK, you’ve got your gloves, lube, fingers, tiny butt plug, and some time. Now what?

Make sure that your nails are filed and that you don’t have any hangnails on the fingers you intend to use on yourself. You don’t have to get a manicure, just make sure that there’s nothing that could tear a glove or cause you some discomfort. You will thank me later.

Pour some lube onto your anus and onto any fingers you intend to use on your anus. Starting with your index finger, use your finger pad trace circles around your anus so that you become more familiar with what feels good. (Maybe you did this with some previous self-exploration.)

A quick note here: use the breath protocol when training. That is, take a big breath into your abdomen (not your upper chest) and then when you want to push into yourself, slowly exhale. It will help you relax more quickly. You can also use this breath protocol when you’re eventually taking bigger toys.

Then, using the breath protocol and leading with your finger pad, slowly push into yourself. You may feel a little resistance at first, but just keep breathing deeply. It takes an overall body relaxation to take something into your ass and so you need to try to relax your entire self. Once you feel comfortable, you can push your finger farther into yourself. If it hurts, back up a little bit, but don’t take the finger all the way out. One finger may be all you can take the first time that you try this, and that’s completely fine. There it lots of time to explore this area, and so you should do so gradually.

Once you’re done, take off the glove so that it’s turned inside out. You may want to take a shower, or you may want to masturbate. Enjoy.

In part 2, I talk about harnesses, dildos, and finally getting pegged by a partner.