Should men be allowed to masturbate?
The short answer is no. The longer answer is that no male, whether under the supervision of a dominant woman or not, should be allowed to touch himself, much less ejaculate without a woman's permission and, ideally, supervision.
Now, that is a rather obviously unrealistic standard but it is really a guide to conduct rooted in a very basic understanding of the correct male female relationship. Far too many men are unwilling to make the sacrifices required to attract and keep the woman they need in their lives. There are many reasons for that failure and one of them is that men are allowed, even tacitly encouraged, to relieve their sexual urges by themselves. While most men have the humility to make their little messes in private, many of them will not recognize what a failure each unsupervised ejaculation actually is.
While the highest and best state a man can hope to attain is chastity in a female-led marriage, on the way to that proper position, there is no reason why an intelligent man cannot ensure that his sexual life is under strict supervision. But this requires a man to look at his sexuality very differently. That shift in point of view is actually even more basic than the simple question of masturbation and it prepares a man for his proper role as his wife or girlfriend's obedient servant.
The key to this shift is for a man to accept that his natural instinct to masturbate is base and very shameful. In our modern age we don't talk about shame very much. Which is too bad because being ashamed is a very important element of being social, being civilized and being well mannered. Interestingly, shame is a tool of control for most dominant women (and many women who do not see themselves as dominant.) Most men are physically much stronger than most women but, somehow, we have evolved social norms and practices which allow women to be safe and, in many cases, equal. That did not happen by accident. It happened because smart women have always known that they could get what they needed by a combination of praise and belittlement. You praise a man when he does what he is told, you shame him when he misbehaves.
Remember that I believe all men are happier when they are submissive? I base this view on the fact that we actually live in a civilized, social and safe society. If men were not at least unwittingly submissive none of that would be possible because there would be no way to control and channel all that wonderful, vibrant but often dangerous and destructive male energy. Which may seem a long way from male masturbation but, oddly, it all ties in.
Well brought up men - an increasingly rare item I note - are given basic rules from a very early age. Basic hygiene, watching their language, and, as they get older, manners almost all of which are about respecting women and authority, usually in that order. Along the way, men learn a degree of personal modesty and a generalized respect for women. Part of that training will include a very strong injunction that masturbation is anything from inappropriate to a sin to something only to be done in private. It varies from family to family. Interestingly, it is extremely rare for there to be a route for a boy or young man to gain permission to masturbate. Even in extremely progressive households - from which Lord preserve me - while male masturbation may be discussed it is almost always in terms of "health" and with the objective of alleviating any guilt a boy may feel. But express permission, particularly from a mother, is pretty much unheard of. (In deeply religious homes the Sin of Onan may come up indicating that God himself enjoins male masturbation.)
All of which adds up to the fact that each time a man masturbates without permission and or supervision he is transgressing against a long cultural and religious tradition. More important, decently brought up men accept, at least tacitly, that the act itself is shameful and does induce a sense of guilt. They may rationalize this shame and guilt away but it remains as part of their consciousness.
The reason why male masturbation is freighted with shame lies in the uneasy biological facts of men and women. Men, as any girl or woman knows, are ready for sex pretty much any time. Women are cyclical and only come on heat a few days a month. Which means that women, over the centuries have had to find ways to keep male sexuality under control. They begin by making masturbation at least a little taboo for young men and they extend their control through everything from dating rituals to marriage.
The objective of this control is to tame the male sexual impulse. To channel it, to domesticate it and to make men conform to their eventual partner's cycle of sexual desire. Obviously, this does not always work. One of the reasons why it does not always work is that a man's sexual desire may overwhelm his early training and sense of shame.
The civilized condition for a man is to be chaste unless and until a woman gives him permission to become erect and, perhaps, to ejaculate. If he does not have that permission and he ejaculates he should, properly, feel ashamed of himself. (And if he is lucky enough to have a dominant wife or girlfriend, he should be humiliated and punished for his animalistic behaviour.) Maintaining his chastity is a gift a man gives women in general, the women he loves and himself.
Of course, chastity is hard to maintain. Masturbatory temptations are as near as your smart phone. Which is why it makes a great deal of sense for a wife or girlfriend to lock her sweetie's cock in a chasitity cage for his own good.
But what about men who do not have a wife or girlfriend to take control of their sexuality. The solution here is actually quite straightforward, a properly tempered man will find a woman to supervise his chastity. Essentially act as his keyholder. It is not at all a difficult position. After practising with his cock cage for a few months and learning, on his own how to take care of the caged cock and how long he can stay in his particular cage, a man can approach a woman he knows and ask her to hold an envelope for him. Of course, if she asks what's in the envelope, it is his obligation to tell her truthfully. Now, she may simply give him the keys when he requests them and that will work because it reduces the impulse ejaculations so many men treat themselves to. Or she may get into the spirit of the chastity experience and extend his confinement. However, once the keys have been given, the chaste man will experience the great relief of no longer having to fight his baser instincts.
Keyholding can be done remotely, I have several keys on my desk as I write this, or it can be done by a close female friend or a man can advertise for a keyholder. One solution a gentleman I know developed was that he left his key with a friendly barmaid at a pub near his home. He was very much a regular and, from time to time, she would bring him his key along with his pint. He would humble himself in the restroom and return the key. Those nights she could count on a surprisingly good tip.
The point of chastity for a single man is to encourage him to find the right woman to submit to on a long term basis. A self-imposed, strict, chastity regime will make that search much more urgent and, importantly, will give a man a real sense of the importance of women in his life. Of course, it will also ensure that when he does find a woman who he feels he can submit to, his submissive nature will be very clear from the beginning. I would think a man in a chastity device would like wait until the fourth or fifth date before handing his date the key and explaining his commitment to chastity both before and after marriage. She might walk out of the restaurant or she might want to learn more about her chaste date.