We’ve been writing a lot lately about anal play and punishment. You may think we’ve strayed from enforced chastity. While Lion may not be caged, I am still his only source of orgasm. I decide when he gets played with and when he has an orgasm. Well, that’s not technically true. When he’s in a slump, I may want him to have an orgasm but he’s unable to get there.

Recently, I’ve changed things up a bit. I’ve been giving him oral sex, but rather than give myself an achy neck or sore jaw, I only do it until I want to stop. Did Lion make it to the edge? Did he have an orgasm? No? Awwww. Too bad. Maybe next time. Or maybe not.

I think it’s been about a week since I made this change. I’ve wanted Lion to have an orgasm a few times. He’s wanted an orgasm every time, I’m sure. I’d guess about 90% of the time he never makes it anywhere near the edge. I know it feels good. He’s told me and I can hear the moaning. Maybe 2% of the time he’s at the edge when I stop and the rest of the time he’s pretty close.

I don’t think Lion would argue with this new technique. It certainly gets him more oral sex which he loves. He may not be getting to the edge as often as before but he is enjoying the journey.

Last night we finally solved the issue of my legs hitting the footboard of the bed. I had Lion lay diagonally across the bed. As a result, he enjoyed a much longer session. See what happens when the Lioness is comfortable? He still didn’t make it to the edge, but we had fun.

Lion attributed last night’s “failure” to the fact that his ass hurt. I’d done quite a bit more anal play than I have in the past. Both the length of time and the movement increased. I still only got four fingers in but I moved them around a lot more. I even shoved them in sideways. If I’m going to open him up, I need to be bit more aggressive than I have been. That’s not to say I was violent. I just stretched him a little more than I have in the past. I was still conscious of his discomfort level and I never went past it.

He also spent some time standing in the punishment corner. He forgot to set up the coffee the other day. Last night, he remembered the coffee but forgot punishment day. That damn Saturday punishment day got him again! That’s normally a funishment, but he’s been forgetting so often that it’s now a punishment. I’m hoping eventually a sore bottom will help him remember.

Tonight maybe I’ll take it a little easier on his ass so he can make it to the edge. I sure would love a Lion orgasm.

When a couple starts out with enforced male chastity, the first question the new keyholder asks is, “How long do you want me to lock you up?” This is probably the last question he wants her to ask. After all, the entire point of enforced male chastity is that the male loses control of when he gets to ejaculate. His keyholder owns that decision.

There have been lots of suggestions as to how to determine this. There are even websites that will give you a random number representing the number of days until the next orgasm. Generally, the guy give some indication of how long he thinks he should wait. Despite what you may have heard, there is no right answer to this question. There is also no such thing as “blue balls”. A man can wait as long as necessary without any physical harm.

Having said that, maybe we can try a creative way to determine how long that wait should be. How about the penis length method? With this method, having a big cock can be a disadvantage. Here’s how it works: Get him as hard as you can. Measure his penis. If you live in the United States, make him wait one day for every inch of length. If you live in a metric system country, it’s a centimeter for each day. If you live in the United States and want to be especially mean, go metric.

As you can see in the picture of my cock (left), I measure 6 inches long. That would make my American wait six days between orgasms. If we follow the metric system, that would be 15.24 cm. As everyone knows, when calculating orgasm spacing, you always round up. That means my Canadian brothers of equal penis size would be waiting 16 days.

Of course, a clever keyholder will realize that for one reason or another she might want to double or even triple the penis-size-calculated wait to a multiple of the actual measurement. I like this system because the male is actually determining how long he waits. Ironic, eh (or Ay as they say in the metric country to our north)?

This method is as good as any other to get you started. Mrs. Lion doesn’t need any system. I have absolutely no idea how she calculates when it’s time for me to erupt. Often, even she doesn’t know when. Her current system is to stimulate me until she decides to stop. If I happen to erupt before she’s through, so much the better. If not, there’s always tomorrow.

Another approach is the pseudo-health calculation. Some women have decided that male orgasm spacing should be based on a healthy interval that allows him to keep his energy without getting so frustrated he would become distracted. I have no idea where these women come came up with their numbers, but a bunch of them have independently suggested the same wait time.

They suggest that it is completely unnecessary for a male to ejaculate more than once every 7 to 10 days.I have no idea why they believe this. Perhaps it’s because once a week is all they want to deal with. In any case, this turns out to be about my average. In 2019 my average wait was 6.8 days. This is very close to the “healthy” wait time suggested by these bloggers. In 2018 my time was 6.2 days. Over the last couple of months, my average is closer to 10 days. Maybe they knew something I didn’t by suggesting 7 to 10 days. Without trying, it seems to be working for us.

Of course, everyone is different. The problem is that when you first start out, you have no idea what might work for you. I suggest the penis-length method. It’s fun and is almost guaranteed to come out with a number of around a week. The consensus seems to be this is a good starting point.

I know that most of the people who read this are men who are want to be caged. I suggest you show this post to your prospective keyholder. It represents a reasonable and lighthearted approach to a subject that causes much more trouble than it’s worth.

Lion's penis in Cherrykeeper chastity device

Putting it into action
Okay, now you have some ideas on how to decide on how long he has to wait between orgasms. Actually implementing this sometimes causes anxiety and can result in a potential keyholder giving up before even starting.

it’s best not to discuss how you decide on wait time. Your caged male, once you are in charge, doesn’t really want to be consulted. A lot of guys enjoy a little humiliation along with frustration. If your guy is one of them, you might want to use my penis size to determine his wait. If you tell him to go to the site and find out how long my penis is and then tell him he gets a day for every inch (or centimeter), it will probably be a little bit embarrassing for him. Or, you can get him nice and hard and measure his penis. Then you can explain why you did it. With an evil smile, you can tell him his wait is X days.

As a matter of good practice, regardless of what he says, keep his initial wait time less than two weeks. A shorter time is helpful because it gives him a chance to get used to being caged, and it gives you a chance to establish a rhythm.

Mrs. Lion jerking me off

When Mrs. Lion and I started out, she agreed to unlock me and masturbate me to the edge of orgasm (usually six or seven times) at least once every two days. This routine is helpful because it gives you a chance to inspect him to be sure there is no irritation, and when you edge him you keep his sexual hormones flowing strongly. This will make it much more difficult for him to last until the day you decide to let him ejaculate.

This frequent teasing makes the game a lot more fun for him, especially if you don’t let him know when he is finally going to get his chance to come. This is how Mrs. Lion plays the game. I never know if she is going to continue stimulating me until I have an orgasm, or if she is going to stop, leaving me hanging. Obviously, almost all of the time I’m left hanging. When I get soft, she puts me back in my cage for another day or two.

That’s how we do it. Of course, you can come up with your own method. Even if you start doing it our way, over time you will probably develop an individual style that suits both of you. The important thing is not to quit. That’s why it’s a good idea to write a simple contract where you both promise to keep going for a certain amount of time. Our contract was for six months. Other people, will choose one or two months. It doesn’t matter. What counts is that you’ve committed to this and will continue long enough to find out if living this way is what you want.

We went out to dinner last night. We’ve been searching the area for new haunts. It will come as no surprise to you that Lion and I have different ideas about restaurants. I like going places I know the food, like Applebee’s and Burger King. Lion likes diners and family-owned places. Fortunately for Lion, we have to go pretty far to find a chain restaurant. Last night’s outing was to an Italian restaurant. It wasn’t bad. A little pricey and not on the same level as our favorite Italian restaurant but much closer.

After dinner we watched TV. We talked about playing and Lion snoozed a bit. I decided it was too late for anal play but I was up for oral play. Lion was up for it too. I don’t know how long we were at it but eventually Lion hit his plateau. I thought we might actually make it. Maybe it was too late. Maybe I’ve lost my touch. Maybe he’s now tired of oral. Maybe he needs mechanical intervention.

I really was looking forward to an oral orgasm. But now I’m wondering if he needs a visit from the Magic Wand. It’s tried and true. I could even try the new fingertip vibrator I bought. One of them will work. Or maybe the answer is simply an earlier start to the festivities. We can try again tonight. I know we keep saying we’ll try earlier and then things delay us. We’ll need to make more of an effort.

Last night Lion suggested French toast for breakfast. At first I thought he wanted to use the bread he just made, but then I remembered we got some cinnamon bread. I told him he could make it. I always do breakfast. For a while, he was in charge of weekend breakfasts and then I took over again. I thought it would be nice for him to do it.

When he went into the kitchen he realized he was in trouble. I asked him why. He forgot to set up the coffee pot. Uh oh. It seems when things are thrown off their routine, he forgets the coffee pot. There are times he never goes into the kitchen at all. Since most of the boxes have been moved out of the way, he ventures through the house more. When he makes it to the kitchen, he usually remembers to do the coffee pot.

For his indiscretion, he’ll either get time on the punishment stool or a mouth soaping. I haven’t come up with any other funishments yet. I don’t consider Icy Hot on his balls to be a funishment. Standing in the corner can be. Maybe I’ll have him do that tonight. We have the perfect corner right near the closet. I could get a sign made up that designates it the “Lion Punishment Corner”.


Mrs. Lion surprised me Thursday night. After her shower, she came back into the bedroom and without a word got out the lightweight Tenderizer paddle and walked over to me. Still silent, she stood by my side of the bed. I asked her what she was up to?

“What do you think? You are getting spanked for being snarky yesterday and today.”

Not wanting to get into more trouble, I got myself into position. Mrs. Lion had chosen the lightweight tenderizer paddle. This particular panel was one of the first we bought on Etsy.com. One side is full of little points the other is smooth. This paddle stings more than any other she has. It doesn’t inflict much damage, but I really hate the way it feels during my spanking.

I yelped from the very first swat. She made a point of pulling my cheeks apart and spanking the tender flesh inside. Because the paddle was so large, she couldn’t get all the way into my crack but got far enough to elicit some particularly loud cries from me. Mrs. Lion has learned to ignore any sounds I make. She calmly goes about her business. After she finished, she said,

“Now you’ll remember to watch what you say, at least for a while.”

lion's naked butt
That’s my bottom after a spanking

Hoo boy, I sure will! Now in the cold light of a new day, I’m not so positive. Sometimes I don’t learn as quickly as I should. If Mrs. Lion catches me even if I make a little slip, and spanks me for it, my confidence that I will behave the way she likes will grow.

There is something important that happens when Mrs. Lion focuses on observing my behavior and punishing infractions promptly: I will learn not to make those particular mistakes, as she says, at least for a while.

I believe that she changes as well. The best way to explain it is that she learns to expect the behavior she has corrected. For example, one rule that she has enforced mercilessly is that she must eat first. I have to either wait for her to begin or get her permission before I can begin eating. I rarely slip on this. When she went to visit her family back East, she found herself uncomfortable at meals when members of her family ate before her. She had been conditioned to observe and react when the rule was broken.

I think the same thing is going to happen as a result of her enforcing the rules about my behavior. I’m hoping she will observe behavior that annoys her and will deal with it promptly. If she does, it will become second nature to her. I think that will be very healthy for our marriage.

Lelo F1s

After my punishment, we rested for a while and then Mrs. Lion got out our new Lelo F1s male masturbator. This is a high-tech device designed to get me very excited and even ejaculate if Mrs. Lion wishes. It’s controlled via a phone app. The current version has 10 sensors that report various conditions about my penis. Currently, there isn’t any software that makes use of this information to change the way the product stimulates me. It appears to have two vibrators inside: one with low, thumping, and one that is higher frequency vibration. The high-frequency vibrator can be adjusted to make it vibrate faster or slower. The low-frequency vibrator can be adjusted in intensity only.

Mrs. Lion began by using her hand to make me hard. Then she put the machine over my penis and turned it on. It took us a little while to figure out how to couple it via Bluetooth with my cell phone. I managed to stay fairly hard until we got the thing working. The sensations were less than thrilling. I tried a wide variety of settings. A few felt pretty good, but there was nothing to get me even close to orgasm.

Autoblow ai

Maybe if someone writes an app that makes use of the sensors to vary the vibrations to maximize pleasure, it could work. Right now, I would label this product as pretty useless. It got fairly good reviews from people on the web. I don’t know why. It just didn’t hit me in the right spots. My next experiment will be with the Autoblow ai. This device is one of the oldest and most successful male masturbators on the market.

It works by having a moving sleeve outside of a silicone sleeve into which the penis is inserted. The sleeve moves up and down stimulating the penis. The older versions of this device maintained a steady up-and-down movement over the full length of the penis. The user could adjust the speed for maximum pleasure. The new ai model is much more sophisticated. It still has the same mechanical up and down motion. However, it’s capable of changing the length of the stroke, the speed, and where on the shaft of the penis it’s operating.

The manufacturer struggled through watching several thousand porno videos of blowjobs. They analyze the mouth movement of the porno actors and programmed the Autoblow to simulate the same actions. It sounds like it’s great. I don’t believe it has the intelligence to understand how excited the person using it becomes. This could mean that people who don’t react in the same time as the program expects, might not have as much fun. We will get one of these and report on our experiences.

After the failed F1s experiment, Mrs. Lion had me wash off the lube from our machine test, and then she used her mouth to stimulate me. No machine will ever feel as good as Mrs. Lion’s mouth. She knows how to play me like a Stradivarius. I loved every second of her sucking. I didn’t get all the way to the edge, but I got very close. When she decided to stop I was very sorry. I’m still really horny the next day.

December 26 is Boxing Day. Traditionally, it’s the day people used to return or exchange gifts. For me it was a day of a sore bottom, a machine test, and a great blowjob. I think that’s way better than having to stand in line to return or exchange gifts. My bottom and penis got a good workout. I hated one and love the other. It’s a bittersweet life I lead.