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.

naked man's penis tickled by a feather
Tease and deny is a powerful and truly fun part of forced chastity play.

As I have often said, most of the so-called advice to keyholders are actually male fantasies couched as “lessons.” Rather than information, it is a wish list created by males who have a rich chastity fantasy life. Those of us with experience generally roll our eyes at the elaborate jerk off fantasies that are out there. Keyholder 101 is based on our experiences actually living with forced male chastity.

Men, like women are programmed to make sex more or less important based on the availability of sexual activity. When you lock up the male’s penis, you are making it difficult-to-impossible for the male to sexually satisfy himself or find someone else other than you to do it for him. He enters a sexual desert. If you simply leave him locked up, after a while sex will become less and less important to him. This is counter productive since one of the central ideas behind forced chastity is for the keyholder to use the caged male’s need for sex as a way to control him.

So how do you keep him frustrated and crazy to have sex without actually getting him off? The answer is something that every woman has been taught is wrong: cock teasing. In most social situations it is considered wrong to arouse a male with no intention of eventually giving him an orgasm. Girls are taught that males can even be dangerous if aroused and unsatisfied. I’m not sure I would go that far, but we can certainly get cranky and hard to be around. In the case of forced chastity, the main reason to lock him up is to keep him extremely horny and frustrated and to use his intense desire to get off as part of the lifestyle.

Many women think that simply depriving him of the opportunity to get off will produce the desired result. It will for a while, but after a week or two of lockup his frustration will diminish and so will his interest in pleasing you so that you will please him. The most basic and probably most effective way to prevent this loss of interest is tease and deny.

This is the classic way to keep a man wanting. Remove his cage and directly stimulate his cock and balls. He needs to believe that you will stimulate him until he can ejaculate. Caged males aren’t stupid. We do know that we aren’t allowed to orgasm without keyholder permission and that sexual stimulation isn’t necessarily going to lead to relief. Surprisingly, even though we know all this, once we are stimulated to a point near orgasm, we lose the ability to think about anything than coming. This level of stimulation happens quickly and only a few seconds before it is too late and he will ejaculate.

Fortunately, he will give you signals when he is ready to explode. If you expect your caged male to be well behaved, he will tell you when he is ready, or maybe ask if you will let him come. In the beginning, just telling you is enough. Don’t necessarily wait for him to tell you or believe him when he does. Every male has a set of uncontrollable signals that signal he is ready to explode. You probably know your partner’s. If you don’t, masturbate him to orgasm a few times and observe what happens just before he comes. It is very likely his breathing will change and he may do other things to signal he is ready.

The actual tease is to take your time getting him excited. Prolong the time before he is ready to come. The reason for this is that you want to give his body time to build up all those nice hormones that go with sexual activity. The more aroused he is, the more important it will be to him that he get off. The art to this tease is a very slow buildup, so slow that he is moving his hips trying to get closer. When he reaches that point just before release, stop all stimulus. He will try to fuck the air, move his hips, do anything he can to go that extra second and ejaculate. Once you get over the taboo, you may find this funny. It is certainly ok to laugh at his antics.

Next, wait until he calms down a little. You don’t need to wait until he gets soft, just enough so that touching his cock won’t get him off. Rinse and repeat. Slowly stimulate him to the edge and stop. Repeat this as many times as you like. This technique can lose its effectiveness if you don’t occasionally let him squirt. When you do want to let him come, repeat the tease and deny several times before finally continuing the stimulation until he can have a nice orgasm. Always do the tease several times first. That way he learns that even after a lot of teasing he still has some chance of coming. He needs to believe this or his body will protect him by making it much harder to get him fully aroused.

If you do this tease and deny several times a week, you will keep your caged male’s attention and improve his willingness to do your bidding. Even if he knows when he will come next, he will be unable to resist your teasing, especially when he has been conditioned to expect teasing before he can finally come. Sound cruel? Maybe under some circumstances it is. But remember this is what he asked you to do. Don’t feel badly that he is so frustrated. Enjoy the obedience and entertainment that a well-teased male can provide.