The issue of whether men kept in chastity should be allowed to orgasm inside their chastity cages is one with many different opinions, and of course there’s no right or wrong way to approach this issue. In my opinion, it’s not so clear cut. In short, it depends.
There are two or three ways that a male in chastity could potentially orgasm inside of their cage. One is from stimulation such as holding a vibrator up to the cage or from anal stimulation such as pegging. Another would be via milking, which has other practical applications. The third would be simply from getting so aroused that the chaste male’s mind brings him over the edge. We’ll explore each of these below.
Orgasm from Stimulation
My wife will often tease me through my chastity cage, but it’s never enough to bring me to orgasm, and she prefers it this way. She doesn’t want me to cum as that would prevent me from being ready to please her when she desires it. I completely agree with this. Also, holding a vibrator up to the cage to bring about an orgasm is problematic, and least in my opinion. As a chaste male, I believe I should be willing to completely give up my ability to have an orgasm. Wearing a chastity cage is my way of letting my wife know that her sexual needs come first, and that I’m willing to give up my ability to orgasm in order to always be ready to satisfy her.
I don’t believe that allowing the chaste male to orgasm from stimulation is a great idea, and that stimulation should cease once he’s close to climax. Pegging is a slightly different story as that has dominant/submissive overtones. Allowing the chaste male to orgasm from pegging is a way of communicating that he’s still not permitted to use his genitals for sexual pleasure, and it allows the keyholder to assert control and to dominate him somewhat. This gets into a gray area and is up to each individual couple.
Milking / Prostate Massage
This is a different story as milking or prostate massages usually only trigger a ruined orgasm, which means that the chaste male will never be completely satisfied and will remain horny and ready to please. Also, milking and/or prostate massages serve the practical purpose of releasing some semen and being healthy for the prostate. A male locked in long term chastity should have the opportunity to ejaculate regularly for the sake of prostate health, so this practice can be an excellent way to keep the male locked long term without having to worry about health concerns.
Orgasm from Mental Stimulation
I will sometimes get so aroused just from pleasuring my wife that it can be enough to cause me to ejaculate inside of my chastity cage. It’s never a fully satisfying orgasm, but more of a ruined orgasm during which semen will trickle out inside of my cage, leaving me unsatisfied and still horny. Personally, I love this type of orgasm as it leaves me still ready to please my wife, and ultimately still leaves me feeling horny and frustrated. More importantly, my wife loves that I can get so aroused from pleasuring her that it’s enough to make me ejaculate. In fact, she finds it hot.
That said, the activity that brings about such an orgasm is important too. If I’m rimming my wife, she’s not as keen to allow me to ejaculate, mainly because rimming brings arousal only to me. For her, it’s more of just a nice massage, but without any sexual pleasure. However, whenever she learns that I’ve had some semen trickle out inside of my cage while I was giving her oral, she loves knowing that pleasing her arouses me so much. In fact, we’ve recently decided that I’d remain locked in chastity until I get so horny and frustrated that I orgasm inside of my chastity cage. Personally, I love this idea as this is one of my favorite ways to climax. And my wife loves it because to her, it’s incredibly hot that I should get so aroused from pleasuring her that it’s enough to bring me to orgasm.
Summary
Obviously, it will depend upon the dynamic in your relationship and the reasons why you incorporate male chastity that will determine whether your chaste male will be permitted to orgasm while locked in their cage, but in my opinion, unless the chaste male climaxes accidentally from the pleasure they experience from satisfying their partner, I believe that orgasms should be off-limits except in the case of milking for the purpose of prostate health. Otherwise, the male shouldn’t be allowed to orgasm until his partner is completely satisfied and decides to unlock him.