Ask Giles: How do I get my vanilla man into male chastity?

This is, of course, not necessarily a good idea. I've covered the caveats in another blog entry about getting your man into Femdom - please click through and read them. All that said, and assuming (1) chastity isn't in some way triggering for him, and (2) you are not putting undue non-erotic pressure on him, then my advice would be as follows.

Your first task is to find
this Chastity Window,
if it exists...

I've noticed that a kinky dynamic is often inherent in the vanilla dynamic.

In other words, if you are interested in male chastity, then there's probably already something going on in the relationship where male chastity would be a natural enhancement -- call it a Chastity Window.

Your first task is to find this Chastity Window, if it exists.

Perhaps you enjoy flirting with each other out of bed? If so -- by making instant gratification impossible -- male chastity can extend this into the bedroom.

Perhaps he seems to enjoy pleasuring you more than he enjoys getting pleasure himself? Perhaps he likes to earn his orgasms?

Look for some erotic activity where his pleasure is deferred, and you control that deferment.

"I will fulfil some of your wildest
dreams if you will wear the
chastity device while I do it."

If you can't find a window, invent one that suits you. Have a clear idea what you want from male chastity. Does the device come off? Does he get to come during "sex"? Are his orgasms rationed? (If it's really Femdom, then the other article might help you.) There's a good chance that if it works for you it will also ultimately work for him.

The idea is that male chastity is addictive - most of its benefits are sensual and psychological, rather than kinky. So once you get your man into the Chastity Window, over time, he will want to stay there.

However, if he's vanilla, then you can't rely on selling him on the benefits of male chastity!

You need to offer him some compelling vanilla or at least non-Femdom benefit. This should not be too hard; he's bound to have a whole list of fantasies, fetishes. Also -- cynically --  given how "dead" most bedrooms become, you just taking any sort of sexual initiative may be enough to motivate him.

What you're offering, then, is a trade; "I will fulfil some of your wildest dreams if you will wear the chastity device while I do it." Of course, over time, the fantasies become wilder but the duration in chastity becomes longer.

Make sure you have provide him with a comfortable chastity device. I can personally vouch for Holy Trainer, Custom Chastity look promising, cheap Chinese devices can be OK for 24 hours, and there's always the Oxballs which are cheap but comfortable.

Once you have a suitable device, you could follow a programme like this (customized for your window and his fantasies!):

1. He wears the device for most of an erotic session. In return, you wear stockings.
2. He wears the device for all of an erotic session but gets to jerk off at the end. In return, you wear stockings and he gets to use sex toys on you.
3. He wears the device for all of an erotic session and overnight. In return, you wear stockings and let him watch you masturbate.
4. He wears the device all week, for the entire erotic session and overnight. In return, you wear stockings and perform any sexual act on yourself that he asks you to.
5. He wears the device all week, for the entire erotic session and overnight. However, the rules now change. He has to buy erotic activity with additional days of lock up, for example, one day per orgasm you have.

The main thing is to offer him wild erotic experiences, but at the price of wearing the chastity device. After a while, there's a chance he will think this is a fair trade...

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Don't resign yourself to just getting off on other people's adventures! When we started out, my wife was vanilla. Use my manuals to help you walk the same Femdom path! There's one for him, and one for her.