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!

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

  1. Pingback: Sweet Weekend With My Boy | The Gentle Domme

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