Ask Giles: How do I turn my vanilla man into a sexual submissive?

Look for two kinds of behavior your man exhibits
that you could extend into Femdom. 

Of course, I wouldn't: I'm a straight male and I'm monogamously married to Xena! However, it's interesting to think about because it makes us consider how submission works without the fetish.

So here's what I'd say to a female friend who wanted to turn her vanilla boyfriend or husband into a submissive. 

(The following assumes consent is given for each step of the way. Please also note that introducing Femdom to the wrong person can be playing with fire and potentially dangerous.) 

Look for two kinds of behavior your man exhibits that you could extend into Femdom. I call these "Femdom Windows":

Service Window: He likes doing stuff too or for you, e.g. if he likes giving you long massages followed by oral. Or pampering you for an evening.
Bottoming Window: He likes lying back and "letting" you do things to him, for example a blow job.

Use your instincts to pick the behavior you think you could most easily extend and work out what's in it for him. There are two broad kinds of incentive:

The Plateau Incentive: Men don't normally have much of a plateau phase. Assuming it doesn't switch him off, anything you can do to string out his orgasm will be addictive.
The Pornstar Incentive: Most men love it when women express sexual agency, by which I mean "act dirty", for example using  a sex toy or letting him use it on you, or dressing sexily, or just loudly expressing sexual pleasure.

Most men love it when women express sexual agency...

The precise incentive depends on the two of you, but it should be something he will enjoy for its own sake, but wouldn't normally get.

For example, in a Service Window, perhaps he gets to dress you in clothing that turns him on, then kneel and watch you masturbate.

In a Bottoming Window you might dress the same way, then string out his orgasm.

Make sure you know how to do the kink safely and successfully, then suggest it during the Femdom Window. Do this casually but sexily and focus on the activity itself: "Whenever you do this I imagine you're my slave and it gets me wet" or "If you let me tie you up I'll give you the blow job of your life".

Once you've done this once, do it again a week later. Keep doing it until you've got it perfect and he doesn't just suggest the activity, he pleads for it.

"Rub my feet, then I'll tie you up."

At this point, two factors should give the kink an increasing momentum:

Conditioning Factor: Men quickly learn to get aroused by things they associate with sex. It's where a lot of fetishes come from. By now he's starting to associate Femdom with being very turned on... :)
Femdom Factor: I'm almost sure that female dominant, male submissive is one of several sweet spots in human relationships. Kink aside, it's certainly a very easy and secure place to sit since everybody knows what to do and the sex is guilt free.

This is the point where you start adding things that you like. They can't be things that repulse or trigger him, but they can be things you like more than he does.

So if you're working on a Bottoming Window, you could make it conditional on him licking you, or get some service first; "Rub my feet, then I'll tie you up." If it's a Service Window, you could extend the service or start introducing discipline. Whatever you do, make sure it's sexy and uses at least one of the Incentives. If he's tidying the apartment, make sure there's a nice surprise waiting for him in the bedroom.

After that, it's rinse and repeat. Keep extending the Femdom Widow either spontaneously or in a planned way. Sooner or later, you'll evolve a dynamic that suits the both of you.

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Why not introduce some Female Centered Femdom to your relationship?