Ask Giles: What do you do if you have a row or spat while in chastity?

There are two aspects to this:

First, dynamic:

Worship isn't the same as "idealise". Nobody is perfect. Worship involves loving a whole person, and doing it from a submissive posture.

And, if you are (mostly) submissive to her in your relationship, it's still an actual relationship. Even the archetypal 50s housewife would put her foot down, push back against manly hubby. It doesn't change the underlying dynamic. FLR type dynamics - we're on the 6th year of ours - aren't day-to-day the same as 24/7 High Protocol relationships.

My experience is that when you're submitting in the bedroom, i.e. doing actual BDSM, in the context of a relationship, it stops being a game. You're submitting to the person, imperfections and all, and that's both hot and spiritually fulfilling: you're cross with her but you still have to do as you're told as if she really owned you... (This is probably dangerous heresy to some people, but it's where the undertow takes me, and it feels great.)

Second, chastity:

I think there's really two styles of chastity: keyholding and "neutering lite", in other words one is about dynamic, the other is about something akin gender identity. If you're drawn to long term chastity, then there's probably a bit of the second kind going on.

By way of illustration (not saying they are equivalent), you wouldn't stop being gay or trans or whatever just because you had a row with your partner; in the same way you need not stop being chaste.

Ask Giles: What do you mean by the Service Model of Femdom? Why do you dislike it so much?

The Service Model of Femdom

Femdom as depicted on the internet and elsewhere is based on what Pro Dommes do, which is mostly doing things to the malesub. It's all about her achieving an effect on him. The domme, as depicted, may or may not be getting paid, and either way there's a happy assumption is that she enjoys wielding the power of pleasure and pain over her sub. That makes Femdom the rough (and more time consuming) equivalent of the vanilla blow job, and like it, it looks awfully like a service.

This is true even when the Femdom "play" is around him performing service: either the service is clearly not an actual service - boot licking, fellating a dildo, lubing up for pegging - or all about her battling to force him to serve and/or the way he dresses etc to do so... in other words, still about him, and still really looking awfully like a service provided by her to him.

There's nothing wrong with any of that. Some women really enjoy wielding power that way, or like being the magic kink fairies, or just enjoy pleasing their partners. (Much like some women really like giving blow jobs, and it's not always a submissive act.)

However, the Service Model has two potential issues. First, it tends to position the domme as a roleplaying the idea of dominant woman rather than just being one off the leash. That kind of improvisation is actually surprisingly hard to do and it's the opposite of empowering. Second, it's often not sustainable long term except as an occasional treat because it requires so much mental and physical effort.

These issues often combine to discourage dominant women from pursuing actual Femdom, which seems a pity for them and the world in general.

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CLICK HERE to download my Femdom Erotica (all written while chaste!)

(For ebook format, 

Lulu or iTunes.)

Ask Giles: Why Are Malesubs Crap (*Often* crap, that is)

Malesubs are often crap, especially the inexperienced ones: entitled, demanding, gross, weird, blinkered... I don't need to give examples. But why?

First, our culture still enables men to be crap about sex in general

Our culture still portrays men as the ones with sexual agency. Sex is still about men, and most men themselves approach sexuality in a wide-eyed boyish way that combines innocence with a lack of reflectivity: "Me... me... me..." In this world, female pleasure is a proof of masculinity and the female body territory to be conquered.

The unreflecting assumption is that Femdom will simply be an inversion of traditional male/female roles, hence the obsession with "serving" one's mistress by being penetrated, and hence unsolicited ass picks.

Couple that inversion with sexist assumptions about women's "naturally" subordinate role, and you explain why malesubs are so keen to emphasise their lack of masculine or high dominance traits: "I know you're a mere weak woman, but I'm a total loser with a small dick who likes wearing panties so you will be able to dominate me."

This exaggerated inversion makes sense when the sub is in boyish mode, but not after he's had a good orgasm. Hence the tendency to flip flop, overcommitting then retreating.

Second, Service Femdom is more visible than "Actual" Femdom.

Prodommes are disproportionately represented in mainstream media, and have a disproportionate presence on the Internet. (After all, this is their vocation. They are easy to contact, often look good on screen, have lots of cool gear, and - if articulate - have tonnes of practical experience to share.)

Meanwhile, the Internet is a good place to talk about the technical aspects of BDSM, so there's more online information about cool rope tying techniques than there is about kinky dynamics and emotions. This makes Femdom look like a service, even when it isn't.

So it's easy to regard dominant women as a cheaper alternative to a prodomme - the equivalent of the nymphomaniac of 1970s sex fantasies: all the convenience and lack of complications of a hooker, but free.

(And perhaps there lingers the assumption that women don't really experience desire anyway, so all straight sex is service; why should Femdom be any different?)

Finally, porn amplifies all this.

Not much to say about that one!

So

Malesubs are crap because: 

Patriarchy, highly-visible Service Femdom, 

and Porn.

(But not my porn!)

---

Learn how to how to walk the same Femdom path with your partner! 

GET THE "FOR HIM" MANUAL RIGHT NOW!
GET THE "FOR HER" MANUAL RIGHT NOW!

CLICK HERE to download my Femdom Erotica (all written while chaste!)

(For ebook format, 

Lulu or iTunes.)

Ask Giles: What do I do once I've locked my husband in chastity?

You need to know what the chastity is about first! It can be one or all of the following:

About you controlling his orgasm. If so, then you can - and he's probably hoping you will - use that power to get things you want. Have him earn his orgasm through chores and pampering, and bedroom service.

About him being locked. If so, then fun is to be had from the fact he can't get off, or even get his dick out. You don't actually have to unlock him to tease him. Just put on sexy clothing and let him pleasure you. For added points, have him wear a strapon to simulate normal sex - there's nothing quite so exquisitely frustrating. And of course there's sexting, little sexy tasks for him during the day, and - if it's his bag - tormenting him by making him wear panties and so on.

About you being penis-free. If so, enjoy getting what you want in bed without any effort on your part, and without the messy finish. Don't even let him mention his dick or his frustration. The effect on him will probably be the same as the previous option, but with less work for you.

And of course you can move between all three of these...

---

Learn how to how to walk the same Femdom path with your partner! 

GET THE "FOR HIM" MANUAL RIGHT NOW!
GET THE "FOR HER" MANUAL RIGHT NOW!

CLICK HERE to download my Femdom Erotica (all written while chaste!)

(For ebook format, 

Lulu or iTunes.)

Ask Giles: Why are dommes often so hostile or dismissive of male subs?

A good proportion of male subs
aren't really psychologically
submissive even though
they might honestly identify
that way.

It's partly supply and demand.

Though the ratio of subs to dommes is something like 5:4, if you remove those who have paired (or poly'ed) off, you get more like 2:1.

This means that dommes can feel overwhelmed and also that if they chose there is no down side to being dismissive. Surrounded by needy men yelping "Pick me! Pick me!" it must be very tempting just to deliver irritated slap downs.

However, there's another thing going on as well.

A good proportion of male subs aren't really psychologically submissive even though they might honestly identify that way. (Sorry.)

These men are either "bottoms" looking for very specific kicks wrapped up in a fantasy, or masochists who therefore have an ambivalent relationship to their urge to submit (if they didn't it wouldn't ping their masochistic urges). The situation is similar to "enjoying gay sex doesn't make you gay".

To make matters worse, the high visibility of articulate and highly skilled prodommes sets all sorts of odd expectations for those men who haven't thought it through. It's the equivalent of agreeing to cook a meal with a friend but actually expecting a restaurant experience.

There's a feminist angle to this as well. Just as the 1970s sexual revolution "freed" women to behave like unpaid sex workers, the 21st century BDSM boom seems to be "freeing" dominant women to behave unpaid prodommes. (rant here)

So, dommes end up experiencing a lot of flip-flopping confusing and flaky behaviour, some of it dishonest.

Which is why many of them have come to distrust male subs.

UPDATE Over on Reddit where I posted the first draft of this, adomme who posts as "adventureismycousin" said:

You know you're there for a Domme's pleasure. But out of a call for submissive men that I sent out earlier this year, and the 35 or so men who responded, only 0 of them were really submissive.
Zero. None. Not a one.
I spent time and energy vetting these guys, apologizing for tardiness to more than half (monogamous as a Domme because I get that invested in my boy), only to find out that I was just a fetish dispenser.

 Go look at the original thread: It's illuminating.

---

Learn how to how to walk the same Femdom path with your partner! 

GET THE "FOR HIM" MANUAL RIGHT NOW!
GET THE "FOR HER" MANUAL RIGHT NOW!

CLICK HERE to download my Femdom Erotica (all written while chaste!)

(For ebook format, 

Lulu or iTunes.)

Does being a submissive make you vulnerable to abuse?

My first girlfriend used to punch me.

We were young - I won't say how young because google - and this wasn't youthful BDSM experimentation. She would fly into rages and punch me because she was angry and it hurt and I would cry.

The worst of it was it would feel right. I think it even turned me on.

Because back then I had the idea that I was different and that perhaps this kind of fucked up situation was my destiny.

Let's not blame her. She had her own issues with anger and sex. She was definitely a victim of at least emotional abuse and I doubt I helped. However, the result was that our relationship was abusive.

She was also wilfully unattractive, the more so as our relationship progressed. Her personal hygiene sucked. Her underwear... ugh. There was even an element of violation in our sexual fumblings.

So, this was as low as I have ever been, and I don't mean in a dark and kinky way. Thank God we never discovered kink together. She would have used against me.

I didn't learn either.

After that, I routinely sought out fucked up domineering rather than dominant partners.

I can also think of several real life friends - male and female - I know to be submissive, Most have similar "romantic" histories of putting themselves in the position of being treated like dirt... up until the point where they embraced their kink and worked out how to enjoy it.

The problem is that though consensual BDSM is very different from abuse, it still satisfies dark urges. Many BDSM dynamics are really nerfed, sexed up and firewalled versions of abusive vanilla relationships.

It follows that if you have a submissive orientation, it's very easy to "accidentally" drift into relationships with an abusive potential, because those are the ones that feel right - the spark is there.

If we introduce kink to the relationship, this can even make things worse because it will erode our negotiating position and, in the hands of somebody ruthless, make us feel even more insecure.

So yes, we submissives are particularly vulnerable to abuse because we have a tendency to put ourselves in harm's way.

(NB This does not justify the treatment: an unlocked door is not an invitation to burglary. Also, the moral equation changes as we get older. An adult submissive who continually seeks out and feeds dysfunctional relationships is an enabler...)

However, if we know we are submissive, if we embrace it, then we can manage it.

We can date dominant, broad minded people, bring up kink early and with pride, or get involved with the BDSM scene.

We don't need to be vulnerable. There has never ever been a better time to be a sexual submissive.

Ask Giles: Why do you keep saying "BDSM emulates evil"? (I always get consent/give consent, plan scenes, give receive aftercare)

"...what would a Martian think when it saw
one of you hurt the other?"

This question keeps coming up and usually goes something like this:

Why do you keep saying "BDSM mimics evil"? I always get/give consent, plan scenes, give/receive aftercare. The sub has the real power anyway, since they can safeword and I/we attended all these classes and raise money for Amnesty International and...

And yet - I say - what would a Martian think when it saw one of you hurt the other?

"Thinking Like a Martian" is the brainchild of Eric Berne, founder of Transactional Analysis and author of Games People Play.

The Martian, being an alien, doesn't understand English an this is immune to the bullshit explanations people give. It can, however, read body language and behaviour.

It's not a very nice way of thinking because it assigns practical responsibility to everybody in a situation - take a look at Eric Berne's reading of the Little Red Riding Hood.

So what does a Martian see when you do your BDSM?

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...

---

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. 

Ask Giles: Do you have any advice for a Domme coming into her own?

What started me - and so, us - on this road was a
particular Ancient Roman fresco from Pompeii

Somebody PM'd me:

I was looking into some of your other blog posts and found them very interesting. It seemed like a long process to get where you are in your relationship.

I have always been an intimidating lady. I like to be the Head Bitch in Charge in all aspects of my life. However I struggle with wanting to make sure my partners needs are fulfilled as well. In the past this turns me into a more timid person, which leads to problems in the relationship, which leads to loss of interest and eventual break up.

As I have been discovering BDSM, kink, and female lead relationships I have realized that this is what I want from a partner and life.

As a sub in your situation(you mentioned in your blog being a "couple first") who had to help his Mistress take a leading role, do you have any advice or tips for a Domme coming into her own?

We're talking relationships here, rather than how to find your place in the BDSM Scene (which is not our thing).

Well obviously, I have my book How to be a Roman Dominatrix which assumes a vanilla female reader. If you are kinky, the transition should be easier but the some of the underlying challenges remain the same.

You do things entirely for your own benefit. Your sub 

agrees to take the rough with the smooth.

What started me - and so, us - on this road was a particular Ancient Roman fresco from Pompeii (see above).

Since he's dressed and she is not, it's reasonable to interpret this as a male slave servicing his owner.

What's interesting about this is that she is just getting what she wants with no sense of fetish or BDSM, and yet if a modern male submissive with a time machine parachuted into the slave's role, it would tick a whole load of kink boxes: objectification, tease and denial, CMNF, service...

So the lesson is that an awful lot of male submissive satisfaction can be generated as a by-product of a super-empowered woman just getting vanilla things she wants.

If she also wants her own kinks, that's a bonus. However what matters, what lends spice to the submissive's experience, is that she has real authority in the relationship. When she's doing kink, he knows that's what she wants and that knowledge itself is a turn on. When he's bored, frustrated or uncomfortable, then he knows that it's because she's in charge, which is also an intense turn on.

Of course this only works if he 

really is a sub..

My advice, then, is pretty much what's in my books. Agree to a set period - a month, initially, is good - in which...

• You do things entirely for your own benefit.
• Your sub agrees to take the rough with the smooth (unless you hit a hard limit).

This will get you both into the habit of female authority as the default (rather than dominance, which requires effort). It will also establish whether this is something you both enjoy, and give you confidence that your sub really is enjoying himself.

It's important for it to be for a set period because otherwise both of you will keep revisiting the decision as to whether to carry on another day or evening when instead you should be reaching an accommodation with your roles.

If you intend to take this out of the bedroom, then I think task lists and some kind of discipline system is a good idea. Not only does this establish female authority, but it is also one of the major benefits of FLR for a man; we know where we stand, we don't get nagged, we do get to atone for our failings.

However, the other advice for doing FLR outside the bedroom is to avoid lots of protocol and to mostly be a couple first where however it's OK for her to get her way and state her preferences.

I think of this as the reverse of an old fashioned marriage. We can argue. We can discuss things. However, Xena has the underlying authority.

Of course this only works if he really is a sub, rather than a bottom who uses submissive fantasies to give some context to his kinks. There's nothing wrong with just being a bottom, but it's important not to confuse the two.

I hope that helps!

---

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. 

Ask Giles: Why male chastity?

Why male chastity?

A friend asked:

What is the attraction for males to be chaste? I understand edging, not being allowed to come. I also understand having someone control when. But are you ever allowed to come? Or is the holding off the most exciting part? More than the release?

I've already written about the vanilla benefits of male chastity. In a nutshell:

• It gives us an extended plateau phase. Let's face, it a few seconds of squirting is a bit anticlimactic after all that build up, so this seems a fair trade - orgasm for sensuality.
• A lot of us feel a bit ambivalent over penetrative sex. This is partly cultural baggage, but also perhaps inherent in heterosexuality since 75% of women can't reach orgasm by penis alone; for most of us, penis in vagina comes as a reward, a gift or an afterthought. This can make us feel exposed and guilty. 
• Finally, female sexuality can be scary. The chastity device is a shark cage.

Now let's talk about submission, masochism and orientation.

...female sexuality can be scary.
 The chastity device is a shark cage.

Submission: Wearing a chastity device, surrendering control of your orgasm is about as submissive as you can get. The more submissive we are, the more we enjoy this surrender. It's an existential thing more than a sexual thing. I just feel right chaste.

Masochism: Masochism makes no sense until you realize that different modules in the brain work independently. I can be turned on by something I don't like, desire what I don't want and so on. Chastity where I don't get to come during erotic sessions is a pretty masochistic experience!  I'm trading orgasm for mind-blowing levels of turn on. The knowledge that I'm in extended chastity gives me a masochistic buzz every time I think about it.

Orientation: The brain is notoriously flexible and it seems that the male brain gets rewired by chastity until it becomes a sexual orientation. I feel sexiest in my device. All my fantasies revolve around being chaste, including my masturbation ones. When I feel horny, I just want to pleasure Xena. Of course the knowledge that my brain has been rewired, that I have been perverted, itself gives me a masochistic thrill...

So, am I allowed to come?Is the holding off the most exciting part? More than the release?

I generally come weekly. Our contract is set up so that Xena's orgasms delay mine. The more intense our erotic relationship, the less I get to masturbate. I would be very happy if Xena had several orgasm a week leaving me effectively permanently chaste. However, since we live in the real world with work and stress and so on, this doesn't happen very often.

I should add that different men like different aspects of chastity. For some it's extended foreplay and it usually, or always, comes off for sex.

---

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. 

Ask Giles: I'm a sub (f) but I want to switch with my boyfriend

"He wants me to lead, and he wants
 to thoroughly please me...."

I'm starting an Ask Giles column, mostly posting -- with permission -- conversations I've had on reddit. 

A lady who normally identifies as a sub sent me a long question:

I'm in a bind, and I wonder if you would be kind enough to share some advice with me.

Essentially, I'm a very sexually submissive and service-oriented woman with a fair amount of experience in D/s relationships, and I'm now dating a man who is kinky but doesn't entirely identify with the bdsm scene.

He hasn't let me be completely submissive with him yet, but we're new, and sex for me is amazing with him regardless. He's recently told me he wants me to switch and be more dominant with him. He is a great lover, and he can switch to be just dominant enough for me (minimum), mostly when I ask for pain play or rough sex, but he's said he doesn't think he can be totally sexually satisfied without also, at least occasionally, me initiating for him to be submissive to me.

He wants me to lead, and he wants to thoroughly please me....

We met without knowing anything about each other's kinks until several dates in, and now we've been dating for a few months and finding a way to make this work has been a frequent conversation topic. The thought of us being fundamentally mismatched just because we both enjoy being submissive is really heartbreaking for me, and I want so badly to make him happy.

I love service, pain play, bondage, collars, rules & protocol, and I've been in 24/7 D/s relationships. I feel I'm so far to the extreme sub side of the submissive-dominant spectrum that it seems so far out of my element to be dominant in any sexual context.

In work and other social settings, I can delegate and take leadership roles when I need to get things done a certain way, though I don't prefer to.

I've been in enough scenes and seen enough dommes in action to have ideas of things I COULD do, but it is almost a turn-off for me to take/use power and control rather than to give it. Even receiving oral sex, which he loves to give, is hard for me to enjoy without feeling like I have too much control/privilege/attention unless I'm restrained or 'forced' to receive it.

I do love sex, I love the physical sensations of sex, I love physical attention and affection, and I do love being adored and cared for. It's just so easy to enjoy it as a submissive, and seems so hard to relax into it in any other role. I want to give him what he wants, and I feel like I don't know how to be or think or feel in a dominant role.
Can you give me any advice from your own experience to help me satisfy his need to switch? Any help would be appreciated.

Note how they met -- "We met without knowing anything about each other's kinks until several dates in" -- which is so common an experience, I'm starting to believe in kinkdar.

I responded:

I'd be very surprised if you can't find a way to make this work! Fetishes tend to be a bit random, but dynamic is inherent in the person, and you two people were together before discussing kink.

It sounds as if his urges are actually submissive rather than bottomish. He's not after particular play, so much as an experience of a particular dynamic.

If this is correct, you don't need to play dom or emulate the dominatrixes you've seen. He's not a scene person anyway. He will measure his experience against what he's previously done, not what he's seen on xtube. In fact, I wonder whether the best approach might be to take off your kinky hat and think just self-centered.

In my self help books I keep harking back to the concept of the Roman dominatrix. She isn't actually, kinky, she just happens to own a male slave, which lets her get her way. Don't think "dom", just think "in control".

It follows that you need to work on just being comfortable giving orders. Intellectually, you must know how mind-blowing it is for him to have his kink satisfied, so your block is at the gut-reaction level. I think you can get around this by initially emphasizing the service side of things. Forget erotic for an hour or so, and just get him cleaning your apartment, sorting your book collection, whatever, with you not domming him, just giving orders.

Another thought - an alternative, or something that might also help - is that you could try setting up experiences that pushed both your sets of buttons. For example, imagine if he was locked into a male chastity device - there are ways of making this a timed thing, outside both your control - and had a butt plug in (thus ticking the anal play box). Anything sensual you did to him would be at once a service to him and a torment, and one of the best ways of getting him close to orgasm would be by letting him go down on you.

I'll send you a copy of my Roman Dominatrix book. It's not quite what you're looking for because it assumes the lady reader is vanilla. However, you might find it's general thrust useful.

She responded:

I love your suggestions of removing myself from the idea that I need to "dom" for him to be satisfied and to begin with service-oriented submission. I have been bossy and self-centered in non-kink contexts before and it's a great idea to try it with him outside of the bedroom.

He will be traveling for work for the next few ways, so while I anticipate his return, I can be thinking about other creative ways of making sensual pleasure "at once a service to him and a torment," as you said so well.

I asked him to write out some short fantasies for me while he is away, and for me to do the same. I presented it as a way to tease each other, but I'm hoping to gain more insight from what he writes on the type of experience he would be looking for as a submissive.
Thank you again for your time. It really helped me to hear your perspective. :) I'll let you know how it goes.

I'll be interested to see how this one plays out...

---

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. 

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?