pegging is an activity that many caged males consider part of their chastity. here i am accepting my lioness' toy.
Pegging is an activity that many caged males consider part of their chastity. Here I am accepting my lioness’ toy anally. She was very patient by slowly inserting so that I could get used to her penetration.

It’s been only three days since my last orgasm, but to me it feels like forever. This is one of my horny times. I don’t know if other males experience this, but my interest in sex seems to fluctuate in some sort of rhythm. When it is at its peak, like now, I want to have sex constantly. Well, not really constantly, but at least daily. When I was younger I did, in fact, come every day. My lioness remembers that and mentions it to me occasionally. She even wrote about it here in a comment to my Gratitude post. Some males really like being forced to wait a long time between orgasms. It enhances their feeling of being controlled. I think it also does that to me too.

My lioness is not by nature a dominant person. She is giving and accepting by nature. In terms of power exchange, we are mismatched. So far she shows no signs of getting any deep pleasure from locking me up and controlling me sexually. She does it because she knows I want it. However, its only been a couple of months and there is always the chance that she will find her pleasure in this play.

It’s all about control
Sometimes it isn’t obvious why I like being caged. It’s not just because I love my lioness deciding if, when, and how I come. It is also about control: power exchange. There is no doubt that the continuous presence of a cage around my cock expresses my lioness’ control over my ability to reach orgasm. But like everything else in life, the fact that it is there 24/7, I grow accustomed to its presence. So, like many other caged males, I like – or more correctly need – additional reminders. When my lioness makes a rule I must follow (like being naked at home or having to spend my weekends in diapers), I am happily reminded of her control. When she spanks me or finds other things to do to me or for me to do, my enjoyment of her control increases. I love feeling her power over me.

One of the key tenets of forced chastity is that I have to wait for any sexual release and that release is at the pleasure of my lioness keyholder. That means there is a sexual desert for me with oasis far apart. Of course I can pleasure my lioness when she wishes. That’s certainly a very enjoyable sexual activity for me. But, all in all, my penis gets lonely in solitary. Many couples practicing forced chastity find other entertainments. These activities are generally entertaining to the keyholder and provide welcome attention to the caged male.

Ruined Orgasm
This practice does let the caged male ejaculate, but with a twist. It’s not hard to do and many women find it amusing. Just masturbate the male until he is ready to ejaculate. Just as he hits the peak stop stimulating his penis. If you’ve gotten him past the point of no return, he will begin to ejaculate. Generally, it will be semen just dripping out of his penis. When that happens to me (accidentally, in my case), I get a feeling like a door is closing. It’s not a satisfying orgasm and I feel the pleasure dripping out of my penis with the semen. It feels very submissive to me. My lioness has essentially taken my semen without giving me the sensation I love.

In the beginning, if you are new at this, you may stop too soon. When you stop, wait about ten seconds. If nothing comes out, resume masturbating him. It won’t take long for you to successfully ruin his orgasm. After he stops dripping, try going back to masturbating him. If he didn’t ejaculate his entire semen supply, you will be able to repeat the ruined orgasm again and again. You will know he is done when he gets soft while you masturbate him. If he remains hard, you can keep going. Some males can leak semen several times. To be clear, while this is frustrating, it is also fun for the male. After all, you are arousing him and he is getting to ejaculate. If my lioness does this to me, I count it as a chance to come. It isn’t my first choice on how I want to do it, but it is still sex. For males who want to be denied for long periods of time, this is probably not an activity you want to do. It does count as coming in a twisted way.

This is the practice of anally penetrating your male. Strictly speaking, it is not part of forced chastity, but many keyholders and their caged males like this because it asserts female control in a very graphic way. There are a few things to know about this hobby. First of all, you caged male will probably whine loudly when you begin penetrating him. You may need to restrain him until he learns to manage his new activity. First consider the hardware.

Many women have inserted a finger into their partner’s anus during sexual play. They may have gotten less-than-positive feedback for doing it. Pegging is different. Your caged male has surrendered sexual control to you. If that includes things like pegging, you have permission to do it. You need to remember this since he will have a learning curve. Males will complain that whatever you are inserting is too big. Unless you are inserting something the size of your arm, this isn’t true. He just isn’t used to relaxing and letting you penetrate  him. A good first pegging toy is a medium-sized dildo. You can find a good guide to dildos here. I suggest you make his first toy a smaller dildo. If it is under 1 1/2 inches in diameter, it will be perfect as his training wheels. A diameter between 1 and 1 1/4 inches is perfect as a starter. Length is not important. Depth of insertion is something you can easily control. Any man is able to accept an eight-inch-long dildo with ease once he has been conditioned to pegging. Silicone dildos are easy to keep clean and can be put in the dishwasher or boiled. Realistic looking dildos have a special little zing for your male. Making him suck it before you insert it also adds to his helpless feelings.

To teach him to accept pegging, start by very slowing inserting the dildo as deeply as you can. Use a lot of lube. If you get a child’s medication syringe (you know, the device that you fill with cough medicine and shoot into the child’s mouth; you can find them at your local drugstore), you can actually shoot some lube up his ass before you begin. Shooting that lube in will improve his comfort. Be sure the outside of his anus is well lubed too. Get a finger full of lube and massage his anus and his entire crack. Most of the pain associated with pegging is caused by friction between the toy and his ass. There is no such thing as too much lube.

Very slowly, but relentlessly push the dildo up his ass. Once it is already in, hold it in place until he gets used to his new visitor. After he gets used to having the dildo up his ass, begin moving it in and out. Don’t remove it entirely and then push it in; just move it in and out, keeping the head up his ass. After a few sessions, you will be able to remove it entirely and then shove it back in. Gradually pick up speed. Do this for at least 15 minutes. He needs time to learn to love your penis. Repeat this exercise at least three times a week. The objective is to teach him to relax his anus when you want to penetrate him.

Once he can accept your penis without too much complaining – some males always complain; it shouldn’t stop you – you can consider getting a strap-on harness. A harness allows you to attach the dildo to your body as though the penis was part of you. That is the essence of true pegging. If you experiment with placement of the dildo on your body, you probably can find a spot where it stimulates your clitoris as you peg him. You can actually fuck him until you come. Over time, consider getting larger (diameter) toys so that he can learn to accept more and more from you. Some women like to compare their penises with their partner’s. They point out how small his is in comparison to hers.

Another fun anal addition is the butt plug. Butt plugs are shaped so that they remain inserted without having to be held in. They come in a wide variety of sizes and offer you the opportunity to train him to accept anal visits without your full attention. Again, use lots of lube and silicone is the most trouble-free material for butt plugs. He can hold a plug in his ass for at least an hour at a time. The main problem that comes up is that the lube can dissipate during his wearing time. That would make removal very painful. To cure this, lube your finger and insert it between the plug and his anus. You can manually re-lube the plug and then remove it.

Above all, remember that if he agreed to pegging, he doesn’t get to control how you do it. He will have discomfort. That’s part of learning to please you. In terms of danger, remember that he poops fairly large objects all the time. His anus is capable of accepting much more than he realizes. The key is to condition him to relax and accept whatever you want to insert, even your hand after he gets good at relaxing for you.

In my experience, the hardest thing for keyholders to understand, at least at first, is that this is what he asked for. I am sure that like me, in his mind, pegging would be fun for him. He will learn that it isn’t going to be all fun. It’s one more thing you can teach your caged male. I will post about other activities a keyholder can do in future posts. Please leave your comments on your play.

1 Comment

  1. Author

    Excellent suggestion! In my next installment I will talk about that nasty torture (and hope my lioness doesn’t read my post). 🙂

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