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.

Male sexuality doesn’t seem very mysterious, but in fact it is pretty complex. Many males complain that after being caged for a while, sex stops feeling as good. Some want to be freed because they mourn the loss of that great feeling. There are two facts about male sexuality that may help explain what is going on and how to remain caged and still have amazing orgasms.

  1. Being locked up “trains” the penis to avoid arousal. Most males report that after a while (days to weeks) in a cage without frequent stimulation, that when freed and given sexual release that the sex doesn’t feel as good. This is most likely due to a physical and mental lowering of sexual expectations. Prior to being caged, most of us knew that if we were teased or if we initiated sex (alone or with a partner), the eventual outcome would be ejaculation. Now, in our new lifestyle, while caged we learn that an erection doesn’t point to release, and if we are freed for a while, we just might end up teased and locked up again without ejaculating.
    Of course we knew going in that this is how forced chastity works. But there is a big difference between knowing and internalizing the harsh reality of sexual frustration. We learn to deal with this in two ways: We teach ourselves to internalize the frustration and use it to feed our submissive / chastity fantasies. Our bodies don’t allow serious arousal until they are sure that the result will probably be ejaculation. As a result, if we are uncaged and our partner stimulates us directly to orgasm, we will probably ejaculate without a problem, but not enjoy the orgasm as much as we did before chastity.
  2. The male arousal curve flattens more than before caging. Females get aroused in a smooth buildup over time. They slowly get more and more excited until they orgasm. Males, on the other hand, get aroused enough to get hard, then very slowly get more aroused until just before ejaculation when over a few seconds arousal hits its peak and ejaculation occurs. Pre-lockup, since we had an expectation of ejaculating when stimulated, while not very steep, our arousal curve did grow as we were stimulated. By the time we hit the point of no return, we were ready.
    Now we have learned that arousal probably doesn’t mean orgasm, so our bodies don’t allow our arousal to grow much until we are close to the point of no return. Basically, we get hard, wait, and when ejaculation is inevitable, over two or three seconds peak, squirt, and are done. We do have a real orgasm but it just doesn’t feel as good.

Coupled with having to wait and wait for a chance to squirt, it’s a big letdown to discover when we can let it go it just doesn’t feel as good. Contrary to common sense, the longer we have to wait, the higher the probability that it won’t be that much fun. Is there anything we can do? There is, but it has its price. One thing is to ask our keyholders to take extra time arousing us when we are uncaged. Maybe play with us for a while and then stop and do something else. Then a bit later start again. That will give our bodies a chance to get used to being aroused.

Of course, all that arousal may just end with us on the very edge of orgasm and being locked back up. That’s the risk. I, for one, like that idea. Psychologically, we are forced to believe we will ejaculate whenever we are aroused by our partner. If we don’t, then when we do get to come, it won’t feel as good. In short, if we want to be sure the occasional orgasm feels as good as the kind we used to have, we need to convince ourselves that every time we are sexually stimulated it will result in a nice orgasm. If we don’t convince ourselves of that, we risk the let down of an unsatisfying orgasm.

For most of us, caged males and keyholders alike, this is unexpected. It makes the delicious torture of orgasm denial that much more poignant. If we want the rare chance we get to come to feel really good, we have to help our keyholder maximize our frustration when she doesn’t let us come. In a way I like this idea. The more I think about it, the more I am enjoying the irony. Being a caged lion turns out to require me to learn new things about old pleasures.


For some time, even before being caged, I wake up at 3 AM or so to pee. As in the past, I frequently find myself aroused. Only now my erection is the same size as my flaccid penis. Its thicker and bulges against the bars. The head tries to push its way out. Some people say it hurts when they try to get hard. It doesn’t hurt me at all. It actually feels good. I haven’t tried very hard, but once my little chubby presses against its cage, nothing I can do with my hand will arouse me further. Orgasm in my cage is apparently impossible. As frustrated as I get, I don’t really want to try to come on my own. After all, I asked my lioness to lock me up. It would make no sense to turn around and try to defeat my cage. What does happen is a little feeling of futility. I know that the good sensation from my erection isn’t going to get any better and I won’t be able to actually come. So, I get up and sit down to pee, return to bed and go back to sleep.

I have always liked a cute butt. Lots of women wear tight jeans which does a great job showing off some truly nice asses. I’ve never been a blatant girl watcher, but i have always enjoyed a casual glance or two. This has been changing since I have been caged. I find myself starting to look and then I catch myself. What’s the point? This is very odd since I have never actually tried to catch any of the cute females I have seen. I guess that subconsciously I had liked the possibility that if I wanted to try, I might have a chance. I never consciously thought about sex with them. I only want my lioness. This subtle change surprises me. It’s like some basic part of my male constitution is restrained by that little cage. I am changed by simply locking my penis up. Who’d have guessed.

A great deal of the forced male chastity folklore revolves around the transformation of the male from inconsiderate thug to simpering submissive. The sexy fantasy has this transformation automatically happening when the lock clicks shut. Many guys try to actually make this change. Has anyone asked the  keyholder what she wants?

Speaking from my experience as a former top, submissive service — you know, fetching things, cleaning, chores, etc. — carries a high price for the top. No submissive expects to just do these things without some reinforcement. It’s like being caged and then having your partner just leave you that way with no further activity or conversation. Sound like fun? No? Well, that means your keyholder has just inherited a lot of homework when she agreed to lock you up.

The point is that most of us guy make a lot of assumptions about our keyholders. We expect them to like their new role and to do all those things that will torment and tease us. We expect them to enjoy our service and provide lots of rules, reinforcements, and punishments. Did we ask them if they wanted to do all this? Nope.

The first time my Lioness and I tried this sort of play, I made all the usual assumptions. I expected her to love teasing me and making me wait for my chance to come. I thought she would enjoy making and enforcing rules for me to follow. Basically I assumed that she would make topping me her new hobby, maybe even career. It’s not too surprising that it didn’t work out. She has other things she would prefer doing. Worse yet for my fantasy, sexual service is not at all what she wants from me. She wants romance and vanilla lovemaking, at least within the limits of being caged. That wasn’t how I thought it would work. I imagined she would lie on the bed and demand I eat her; tell me to lick her all over, bathe her, etc. Nope, not at all.

It all comes back to the fact that forced chastity is rarely the idea of our partners. We come up with it and then expect full participation in our fantasy. That sounds more like work to our partners than fun. I realized that I needed an attitude adjustment. I’ve been working on making that change since I’ve been locked up. If you read the featured post and my Lioness’ response, you can see that I haven’t been very successful. However, I now have a fairly clear idea of what I need to do. She’s working hard to give me what I want. I am reciprocating. That’s the whole point; chastity is for us, not something done to us. We need to pay back the favor with our keyholders, not in some fantasy submissive way, but in a way she wants.