Keyholder 101: Pegging

anal penetration

Pegging is anal penetration by the keyholder.

Strictly speaking, being a keyholder doesn’t require any activity beyond locking up your male and occasionally letting him out for hygiene and exercise. However, very few caged males would be happy with such a limited confinement. As a keyholder, your experience would also be rather one-dimensional if limited to the basics. Last time we discussed tease and denial as an amusing part of forced male chastity. Today’s topic is quite different.

Tease and deny is just a small variation on an activity I’m sure you have done many times in the past. Pegging, however, may be new, even alien to you. What is this activity? It’s anal penetration of the male by his keyholder. Don’t stop reading. It turns out that this is an activity your male will end up loving.

Before we go any further, let’s get rid of some common concerns. A big one for many is that male anal penetration is homosexual. If a male likes it, he is a latent homosexual and if you teach him to enjoy it, you are making him queer. The simple fact is that men and women both have lots of pleasure nerve endings in the anus. Enjoying activity there says nothing about sexual orientation. Stimulation there can become very erotic and fun for both men and women regardless of sexual orientation. Another concern is that you could hurt him by inserting something up there. Actually there is no serious danger if you are sensible and take feedback from your male.

The biggest objection is that it is “dirty” back there. A lot of people hang on to things learned in early childhood; namely that the asshole is dirty and needs to be avoided. The fact is that with a little washing, the rear can be a very nice place to play.

Ok, now that we have that out of the way, let’s talk about the activity and the necessary tools. The first thing you need is a dildo. This can be a realistic imitation penis, or something more abstract. The best material is silicone. This stuff is dishwasher safe, can be boiled and won’t absorb anything. You can find lots of them here. What about size? The key measurement is diameter. Length isn’t important since you control depth of insertion. Over time (a month or so), you will actually need several sizes. A good starter size is about one inch in diameter. Most men can learn to accept that fairly quickly. After he is comfortable with that size, you can move up to 1 1/2 inch. That is a good size to stay with, but moving up further is good training for him in relaxing and letting you do as you wish.

Technically, pegging is done with the dildo in a strap-on harness. This device lets you wear the dildo as though it were your penis. Pegging is using your strapped on penis to fuck his anus. However, at first the harness is not really the best idea. You need to get him used to your penetration. That is best done with him lying on his stomach and you holding the dildo in your hand. Take the beginner dildo and get it covered with lube. Also use your hand and lube his anus. You can’t use too much lube. Most of the discomfort he will feel will be due to insufficient lube.

Take the lubed dildo and slowly insert it in his anus. Take your time. Keep a steady pressure on it so it slowly goes in. If it hurts him and he wants you to stop, pause. Leave it where it is. If that is still too painful, slowly remove it, add more lube and begin again. It takes patience and time. The first session might only last five or ten minutes. Hopefully you will be able to get it all the way in. Hold it there. Don’t move in or out. Just let him get used to it. Hold it for ten minutes if he can accommodate it. Then very slowly remove it. Whatever you do, don’t abruptly end the session because of complaints. Be sympathetic but firm. Remove the dildo for a minute or two then start again. The key is to make him realize that this is going to happen and while you will let him rest a bit, the dildo will go in. After you have it inserted and held it there a while, you can slowly remove it and end the session.

sIf he isn’t sore the next day, repeat. It is perfectly normal to be sore for a while until he learns to relax. It isn’t dangerous or a bad sign. Let him know it is a normal part of learning to use new muscles. That’s exactly what it is. After a couple of sessions, begin moving the dildo in and out. Don’t let the tip completely exit, but pull it out as far as you can and push back in. Start slowly the first time. Build up over the next few sessions.

Now you can add the harness. Wear it tightly strapped to your body. Try positioning the dildo so it is right over your clitoris. That way, each thrust will stimulate you. Some women can orgasm that way. Now you can really peg him.

Believe it or not, most men learn to love this. It’s a great part of the forced chastity experience because it is very physical and sexual without providing him with an orgasm. It is also an unmistakable message about your dominance. Remember, this takes time and patience. Your efforts will be rewarded.

Caged male half of a happy couple practicing enforced male chastity and domestic discipline. Locked since 1/2014. Domestic discipline 3/2015. Lion's first mouth soaping was 7/17.

Posted in Advice for a new keyholder, Femdom, Keyholder101, Lion's Journal, Living with chastity

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