The Gentle Domme’s Guide to Cross-Dressing, Feminization and Sissification for New Dommes and Subs: Part Three

femdomme latex gloves

If you haven’t already, check out the first two articles in this three-part series about cross-dressing, feminization and sissification. So far, we’ve talked about the differences between cross-dressing, feminization and sissification and discussed the discomfort some dommes feel with sissification and forced feminization play because of misogynistic stereotypes.

If your boyfriend or husband has confessed having fantasies about feminization and you have some questions about what this means for your relationship and where these fantasies might be coming from, these articles should help you make a little more sense out of his desires, especially if they’re connected to his submissive nature.

So, you’ll notice that in these articles, I’ve provided a lot of information about what cross-dressing, feminization, forced feminization and sissification are and aren’t and not a lot of information about how to actually help make this kind of fantasy a reality in your relationship.

The truth is that understanding why your partner has these fantasies is more important than exactly what you do to make them happen in real life.

The truth is that understanding why your partner has these fantasies is more important than exactly what you do to make them happen in real life. For example, if your boyfriend or partner just wants to feel pretty in a way that can be hard to achieve in typically masculine clothing, he may be satisfied with wearing a pair of sexy panties and some lipstick while you make out. He may be closer to a cross-dresser, in that it’s not really about feeling submissive. Or he may have some feminization fantasies, but being in some women’s clothing or make up are enough to bring up those submissive feelings he’s craving.

If he has objectification fantasies about being a “slutty cheerleader” taken and used by the football team, that fantasy is stemming from a different place. He might want to feel viewed like a sex object in a way that women often are and men usually aren’t.  Or he might want to feel sexually vulnerable. Or, maybe he wants to feel naughty for having such voracious sexual desires when he’s supposed to be pure and virginal. If you’re into it, you may get a cheerleader costume, blindfold him and tell him what a dirty girl he’s being while you give him a good pegging.

He might want to feel viewed like a sex object in a way that women often are and men usually aren’t.  Or he might want to feel sexually vulnerable.

As I said before, think of this kink more like a spectrum or buffet than something specific. Your partner likely wants to achieve some kind of feeling out of this experience. So, the goal is to bring out the feeling—seductiveness, vulnerability, embarrassment, humiliation—rather than focus too much on the exact items you need to make the scene happen. I would say that a good role play scenario doesn’t hurt! It can feel a little silly to pretend that your six foot tall brawny husband is a delicate flower, so using a trope like teacher/student or boss/employee or stripper/patron or even strict home owner/dainty maid can help get you in the right mind-set and past any initial giggles. (And really—it should be fun. It’s okay to laugh, if it’s out of play and joy.)

In my case, as I mentioned earlier, I never thought I would be into feminization. Although I do like some feminine qualities in men, the thought of my partner entirely cross-dressed didn’t seem appealing to me because I’m primarily straight and like masculine presenting bodies. While I wasn’t disgusted by the idea of dressing my boyfriend up in my lingerie, I didn’t expect it to be erotic. It was something I was doing for him.

However, once we actually did it, I found that I kind of liked it. He was very shy and unsure and really slipped into a vulnerable place. I thought it was a bit amusing that he so obviously associated femininity with vulnerability, complete with big doe eyes, but he was a little like a baby deer taking his first steps—especially when he tried on a pair of size 11 heels.

I helped him put on makeup, and I could tell he was getting really turned on by the whole thing but was also kind of embarrassed that he was getting so turned on, and his embarrassment made me like it more—because I like seeing men embarrassed! When we were done, he was very pretty. Especially from behind, he looked like a slender babe. I was almost a little jealous because he had a better body than me!

I helped him put on makeup, and I could tell he was getting really turned on by the whole thing but was also kind of embarrassed that he was getting so turned on, and his embarrassment made me like it more—because I like seeing men embarrassed!

After that, we played out an objectification fantasy where he was the pretty young thing who was being taken advantage of. We had some trouble deciding on what pronouns to use and what names we were giving to body parts. So, that’s something you might want to talk about beforehand. Does your partner want to look feminine, feel like a woman or be referred to as a woman with female parts? But the whole thing turned out to be a lot of sexy fun.

In our case, feminization is something we do infrequently. It turned out that once my boyfriend’s itch was scratched, he didn’t desire it so much anymore. And now it’s something we toy with once in a while, although he often likes to feel soft and slightly feminine in our sexual relationship, and I enjoy that softness. But he doesn’t require female clothing to achieve it.

However, for some men, it’s something they will want all the time. And it will be up to you as the domme about how much you want to participate in it–if it’s something you enjoy all the time or just sometimes on special occasions. You can also go slowly and feel out your emotions regarding humiliation play connected to gender roles.

In kink, we tend to focus on physical play when it comes to negotiation and a fear of injuring someone, but often emotional and psychological play can be just as fraught with danger. And while we want to give our submissives want they want and make them happy, we need to consider their best interests, as well as our own.

The Gentle Domme’s Guide to Cross-Dressing, Feminization and Sissification for New Dommes and Subs: Part Two

domme in lingerie

In my last article I talked about what to do if your male partner comes to you and wants to dress up like a woman. In that article we talked about cross-dressing and feminization and the differences between the two, especially that while cross-dressing is not necessarily submissive, feminization fantasies usually are—at least a little bit. So, start there if you need some help understanding these terms and their distinctions….

There is another “level” or “type” of feminization that’s called sissification. Most of us over a certain age can remember the word “sissy” as a slur against boys who weren’t acting manly enough, or whatever the schoolyard bully or an abusive dad or older brother decided was manly enough. Being a sissy meant that you were a weak boy who acted like a girl. It was one of the worst things a boy could be called.

Sissification has its roots in that humiliation. It’s basically feminization taken the to the extreme. A stereotypical sissification fantasy would be a man who is dressed up to be ultra-feminine. He would have a long, curly wig, wear garish makeup, a lispy voice, a French maid’s uniform and be put into service cleaning his domme’s house, with her gentle or not so gentle encouragements. This is a major stereotype here. But it’s the one you will hear dommes who dislike sissification complaining about ad nauseam. For a somewhat valid reason. 

To understand why some dommes really hate sissification, let’s talk more about the WHY. Why are submissive men into feminization and sissification into feminization and sissification?

To understand why some dommes really hate sissification, let’s talk more about the WHY. Why are submissive men into feminization and sissification into feminization and sissification?

Okay. Well, first, you don’t have to be into sissification just because you’re into feminization. Think of this all like a spectrum or a buffet. You can pick and choose what you like. So, don’t assume that because your partner is into the idea of feeling like a woman, he also wants to wear doll clothes and frilly socks and clean your house with a feather duster while you swat at him with a crop.

The reason that a lot of dommes are not into sissification, even the ones who are into guys who like to cross-dress or be feminized is that they see sissification as humiliation play. They feel that the men who are into it consciously, or more likely subconsciously, see being a woman as something that is less than a man—and therefore worthy of being made fun of.

The reason that a lot of dommes are not into sissification, even the ones who are into guys who like to cross-dress or be feminized is that they see sissification as humiliation play. They feel that the men who are into it consciously, or more likely subconsciously, see being a woman as something that is less than a man—and therefore worthy of being made fun of. Rather than questioning why being called a sissy is a bad thing—is it so bad to be feminine—they believe that these men have internalized the shame of not being seen as masculine enough and are acting out this shame through kink.

One big subgenre of this entire fantasy is forced feminization, which is exactly what it sounds like. It’s when your domme “forces” you to dress and act like a woman to humiliate you. There’s also an overlap here with “forced bi,” which is when a submissive man is “forced” to be sexually submissive to another man. “Forced” in heavy quotation marks, because of course, the submissive wants to be forced. That’s part of the fantasy. He doesn’t really want to dress up like a girl or give another man a blow job. You’re making him do it, so it’s not his fault! 

It’s a little easy to roll your eyes at this, but when you think about it, it’s not so different from romance novels where women are taken by rich, powerful, gorgeous men and “forced” to endure their passionate lovemaking. Non-consent fantasies are hugely popular in both sexes. They allow people to feel free of the internal shame they carry around about their desires.

But, obviously, since femdommes are women, some feel that encouraging this behavior is essentially saying that it is humiliating to be a woman, or it is humiliating for a man to be a woman or be like a woman. This is particularly loaded now that we, as a society, are becoming so much more comfortable with the non-binary and with violating these perceived gender norms. And being a femdomme theoretically means that you are supposed to be a powerful woman. So, how can a powerful woman condone fantasies based on misogynistic stereotypes about women?

Some dommes just don’t like it for this reason. They feel like they are essentially agreeing with the schoolyard bullies instead of saying that there’s nothing wrong with feeling, looking or acting like a man who isn’t stereotypically masculine.

Some dommes just don’t like it for this reason. They feel like they are essentially agreeing with the schoolyard bullies instead of saying that there’s nothing wrong with feeling, looking or acting like a man who isn’t stereotypically masculine. They also might say that “forced bi” is just a way for a man to resist coming to terms with his bi-sexuality, and that he’d be happier if he could accept that part of himself.

For this reason, you will find quite a few dommes who are totally cool with cross-dressing and feminization, but who draw the line at forced feminization and sissification. They have no problem, and might even think it’s hot, to have a partner who flirts with gender norms for fun, to feel sexy and pretty, for role play, but they dislike this kink if its born out of a desire to be humiliated for being feminine.

And, of course, there are plenty of dommes who have no issues with forced feminization and/or sissification. They might say that kink is kink, and in kink we play with a lot of taboos, and they don’t judge. They might enjoy the humiliation aspect of forced-feminization and sissification because they enjoy humiliation in general, and they feel like if their partners like it and they like it, what’s the problem? Or they might feel that it’s not degrading at all to women, but just degrading to men to turn them into what are basically cartoonish versions of women. Some people might even feel like it’s a safe way to exorcise those demons of not feeling manly enough. Nothing in kink is ever black or white…just black and blue.

So, now that’s we’ve explored why some submissive men are into cross-dressing, feminization and sissification, let’s discuss how you can work these kinks into play, if you want to do that. Stay tuned for my next article in this three-part series….

The Gentle Domme’s Guide to Cross-Dressing, Feminization and Sissification for New Dommes and Subs: Part One

feminized cross dressed man

So, your submissive boyfriend or husband has confided in you with a deep, dark fantasy. He wants to dress up like a girl, and he wants you to help. Well, buckle up, buttercup. This is going to be a long one!

You likely have one of several responses, varying from, “This relationship isn’t going to work,” to, “Where’s my red lipstick, and get the fishnets out of the drawer, pronto!” I’m going to assume since you’re here that you didn’t end your relationship, and also that you’re a little hesitant about what to do next, unless the red lipstick and thigh highs are currently next to your phone and you’re reading this just for kicks.

First, I want to say this. I think that in our culture that doesn’t provide men with a lot of ways to express themselves outside of stereotypical gender norms, it takes a lot of strength for a man to tell his female partner about these kinds of fantasies.

First, I want to say this. I think that in our culture that doesn’t provide men with a lot of ways to express themselves outside of stereotypical gender norms, it takes a lot of strength for a man to tell his female partner about these kinds of fantasies. And I definitely do not advocate shaming anyone, especially an intimate partner, for being honest with you about what he wants or needs. That takes a lot of courage and trust, which I think should be respected and treasured.

However, I also want to stress that it IS okay for you not to be into seeing your man cross-dressed, which is the definition of dressing up like the opposite sex. Feminization, which is cross-dressing plus adopting typically feminine attributes and mannerisms, is a relatively common submissive fantasy, although cross-dressing itself does not necessarily have anything to do with submission. So, I’m talking about it here on TheGentleDomme.com because of its connection to kink. When I talk about cross-dressing, I’m removing it from the ‘kinkosphere.’ When I talk about feminization, I’m connecting it to submissive kink. That’s important to understand because of the differences in motivation. Plenty of otherwise vanilla men are into cross-dressing, but men who want to be feminized usually have other kinks connected to submission. Usually. Not always.

(Feminization can also be connected to sissification, but let’s get to that a little later, since sissification tends to be even more controversial in the femdom community.)

Just because you enjoy having a submissive partner doesn’t mean you must be into feminization. I just want to clear about that, because the intimate things people do together should be things they both enjoy. This really is something that some people love and some people just don’t get. And that’s okay.

If you have a submissive partner who wants you to feminize him, it’s awesome if you want to try it out and fantastic if it turns out you’re both into it. I should admit that it was something I didn’t think would be very hot, but I enjoy it a lot more than I thought I would. But if it turns out that you don’t, you don’t need to force yourself to indulge it just for the sake of your partner. That’s not going to turn out well for either of you. He’ll be able to tell you aren’t excited about it, and you will likely feel imposed upon.

Now, disclaimer out the way, let’s move on and assume you’re at least curious about your male partner’s confession. First, you may be wondering—why? Does this mean he’s gay? Does it mean he wants to be a drag queen? Does it mean he’s transgender?

Well, I don’t specifically know the reasons why every man into cross-dressing is into it. But most of the time, men who like to cross-dress are straight. And, as for where this desire comes from, it differs for people. As I said before, cross-dressing is not necessarily a submissive activity. Lots of otherwise vanilla men dabble in it or live it 24/7 for a variety of reasons, such as that it feels taboo or they like the feel of the fabrics on their skin or they just want to feel pretty. For example, here’s a story about a man who liked to cross-dress as a way to relieve stress.

So, if your subby hubby expresses a desire for you to dress him up and help make him feel feminine, one possibility is that he literally just wants to cross-dress. However, because we’re on a kink site, I’m going to assume that his longings are coming from a place of submission. Obviously, you should do your communicative homework on this.  You know what they say about assuming and asses. So, now let’s delve a little deeper into feminization.

Feminization is essentially the kink form of cross-dressing, at least that’s how I would define it. Men who want to be feminized don’t just want to dress up in women’s clothes. They want to feel like a woman.

Feminization is essentially the kink form of cross-dressing, at least that’s how I would define it. Men who want to be feminized don’t just want to dress up in women’s clothes. They want to feel like a woman. Sometimes they want to adopt a different name while they’re feminized. For example, instead of being Gabriel, they want to be Gabby while they’re feminized.

They might want to walk in a more feminine way, talk in a higher tone, perhaps have sex in a way that they feel is more feminine. And they often want their domme’s direction in achieving this. They might want you to help them put on makeup, select clothing, guide or even punish them as they learn how to “be a woman” for you or around you. Whereas cross-dressing is not necessarily sexual, I would say that feminization usually is, although, of course, someone will inevitably disagree with me about this.

…So, now we’ve discussed cross-dressing and feminization. But we’re not done yet! Stay tuned for my next article to learn more about sissification. This is a big topic, and I have lot more to say about it!