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

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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.

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