Cherry Keeper chastity device headlock
This is the first custom version of the Cherry Keeper. The “shelf” is the headlock. The opening is just slightly larger than the diameter of Lion’s penis shaft. The head has to be worked through this smaller hole. Once inside, the shelf formed by the headlock prevents the head from moving backward. This keeps his urethra nicely centered.

Lion has a theory that the sores on my weenie were caused by the cage. He thinks he may be getting pinched or nicked when it goes on or off. I’m trying to remember if he had sores when we were using the Jail Bird. I think he did. When he got pinched with that, I don’t think it was in the same area. My theory, if the sores are from the newer cage, is that there’s a rough spot on the headlock that doesn’t exist on the newest incarnation even though we’ve been very careful recently. I still need to examine the other cages to see if my theory is correct.

The thing I’ve thought about with each version of the Cherry Keeper, is if the requirement that Lion has to ask me for each new purchase applies only to new, new purchases or if it applies to any purchase. I can see the argument for it being just different variations of the same purchase. I can also see the argument for it being more stuff accumulating on his nightstand and that is clearly a new purchase each time.

my penis in the new custom cage
Lion’s penis in the custom Cherry Keeper. The headlock keeps the head against the top of the cage, nicely centered.(Click image to view larger)

Ultimately I want him to have a good fit. However, I dislike the headlock idea. Maybe I just dislike the last two or three versions with the extreme headlock. I know my weenie is pliable but jamming the head into a small hole is just asking for more sores. And whomping his butt is one thing, jamming my weenie into anything is not something I want to be a part of. If he wants to continue wearing the Cherry Keeper with the narrow headlock then maybe he needs to deal with the cage by himself. How many times has Lion said that if you need lube to make the cage comfortable, it’s the wrong size? I know that was in relation to the actual wearing of the cage, but to me it’s the same thing.

[Lion — I don’t think a little lube on the head of my penis to make it easier to fit through the headlock is the same thing. The headlock has been very successful keeping my urethra centered in the opening provided for it. I’ve been able to pee standing up with no mess or spray. I’m hoping Mrs. Lion will let me continue using this feature.]


  1. I’ve been following Mr. Lion’s adventures with the headlock from the start. I always thought that if it was hard to put on, it would be harder to remove. I understand his feelings that standing to urinate is important. (My feelings are that having to sit to urinate comes with the territory.)

    For me, I don’t think that having to deal with sores justifies the use of the urinal.

    1. The source I think, were caused by both of us being too rough getting in and out of the cage. We’ve gone quite a few days now with absolutely no injury or problem. As a matter of fact, getting the K John is a little work pushing the head through. However, the whole wasn’t that small and Mrs. Lion is having very little trouble getting in on me now. Taking it off is very easy. It takes maybe one second more than it took removing a cage without it. All in all, I like it.

  2. I have been experimenting with the short and small versions of the cherry keeper with different sizes of headlock and found the medium to be a good fit. It keeps the head in place which makes the cage more comfortable. It really does not do anything to prevent pullout unless you make the hole so small that it squeezes and keeps the head and glans swollen. That is not something you want to do long term.

    1. Actually, the headlock wasn’t really the problem. I’ve been in the cage with it being removed at least once a day for nearly a week now without any injury. I think the initial problem was simply being too rough trying to get the entire head in.

      The first cage I bought was the small with a medium headlock. The cage was a little bit too short for my head. The medium headlock didn’t offer enough support. The custom cage is longer and narrower (which goes a long way keeping my urethra centered). The opening in the headlock is just a bit wider than the diameter of my shaft. It’s not very hard to put on and is so comfortable I often forget it’s there at all. Since the hole is a bit larger than the diameter of the shaft, there’s no risk of squeezing or otherwise hurting my penis. I will be putting out a full review of the Cherry Keeper in the near future and will discuss sizing.

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