Advice for trying to get someone into gender-bending

monomorphic · Apr 16, 2011

I'm starting to get really into the idea of crossdressing and gender-bending, sometimes forced sometimes not. My g/f isn't really into the idea but she's not experienced at all with anything really (I was her first and I let her take it slow for a while). Is there any advice anyone can give about how to introduce her to the idea of me being a "girl" for the time we're in bed?

Smallest · Apr 16, 2011

If she's not into girls, it'll be hard to make her enjoy it

Nuka · Apr 16, 2011

You could put it across as her Domming you... if you want to take it as far as her fucking you with a strap on etc. As for the cross dressing parts, that will take time, remember communication and comfort.

TerribleT · Apr 18, 2011

Hey Mono.
I would feel it out tactfully.
Since she hasn't had a lot of time to form the usual blocks and pre/misconceptions, you can hopefully ease into a discussion about it without either of you feeling too uncomfortable.

I say this because I just had a conversation with an older woman, divorced and alone, who broke it off with a really great sounding man she was dating because he told her he liked to dress in womens clothes. Here she is, an attractive red head but in her 50s, she had a decent dude and kicked him to the curb. Hey...her loss!

sebastian · Apr 18, 2011

Terrible, cross-dressing is a very complicated fetish. It violates our understanding of what defines gender, which for some is excitingly arousing and for others is disturbing. I fall into the latter group. I'm attracted to men who look like men. I don't sleep with women because I'm not attracted to the physical qualities of women. So when I see a man who is dressing like a woman (for example, wearing panties or heels), I actually feel a shudder of revulsion. It's hard to explain exactly why, but it's a bit like watching someone go to great lengths to bake a perfect cake and then ruin it by frosting it with ketchup. (That's not to say that cross-dressers are inherently gross or anything, simply that I find them deeply disturbing. And only when they're obviously men dressing as women. I quite like good drag.)

So if this woman feels about cross-dressing the way I do, then she broke up with the guy because she recognized that on a deep level they were incompatible. She probably wants a very masculine man, and felt that his cross-dressing somehow tainted his masculinity even when he wasn't doing it, sort of the way you wouldn't want to use a dirty spoon to eat ice cream with.

Kor · Apr 18, 2011

Sebastian has a good point. Sometimes people run into hard limits they didn't realize they had, and that might cause trouble later.

If she's uncomfortable with you cross-dressing, you might approach from the other angle. To please you, would she be willing to dress male?

For some reason it seems more common to see men cross-dressing than women, though since the accepted female wardrobe seems to include everything that men wear, it might be hard to tell... some women seem to have fun playing "boi", though.

sebastian · Apr 18, 2011

Mono, here's something I posted in one of the other threads that you raised this question in:

I don't have interest in or experience with cross-dressing (it actually sort of icks me out, except with drag queens for some reason), but perhaps this will help you think about it. Some guys get into feminization because they feel it adds something and is a positive experience: it shows them their 'feminine side', provides a relief from the pressures of masculinity, and makes them 'feel pretty' or so on. Other guys get into feminization because they feel it takes something away and is a negative experience: it strips them of their masculinity and power, it degrades and humiliates them, and renders them submissive. Which category do you fall into it? I ask this because I think which category you're in will influence what you're looking for and how you can ask for it.

TerribleT · Apr 18, 2011

Im a little judgemental I guess. Cross dressing doesn't bother me...definitely not enough to end a relationship over it anyway. I am concerned with what my partner wants and, even if its something I don't like or don't want to do, I would do it.
I have a hard time seeing the other point of view on this but I don't dismiss it. That's why I wouldn't just go ahead and blurt it out if I was the OP.
To me it would be totally fine if my wife all of a sudden wanted to dress up like Paul Bunion and make me wear a Teddy.
The grossest thing I can think of right now is beastiality but, even if I had to share her with the dog, that's somebody I care about....a lot. Id have to do it.
I would have to be totally appalled to the point of calling the police before I could bring myself to hurt someones soul like that.....by telling them "no way! Your a freak! Its over!"
I dunno. Dressing up like a chick seems pretty harmless to me.
Not trying to minimize any one elses POV at all. More=better here, I think.

sebastian · Apr 19, 2011

Terrible, it's funny what different people find acceptable or not acceptable. Our kinks are deeply rooted in us and what seems harmless to one person can seem completely revolting or unacceptable to someone else. I find water sports very arousing, but others consider it filthy. I love humiliation and verbal abuse, but many serious kinksters consider it emotionally harmful. Others find crossdressing intensely arousing; it makes me queasy. You consider bestiality extreme but probably ok; I'd argue it's never acceptable because the animal can't give true consent.

There's even a way to express this idea in the BDSM community. It's called "your kink is ok" or YKINMYKBYKIOK. Both are shorthands for "your kink is not my kink, but your kink is ok".

monomorphic · Apr 19, 2011

Thanks for the insight everyone. Sebastian, you have a good point and I'm trying to work our conversations towards whether she'd be accepting of this or reject it. Instead of trying to get her to see what I want, I've tried to get her to explore herself a little bit more (which she's never done before). I feel that if she's able to find something that she feels she strongly wants, she'll be able to understand where my feelings lie when the conversations turn that direction. If it turns out that I can't do that and be with her, it'll just be something that I don't get to experience. Above all, she's the most important.

Advice for trying to get someone into gender-bending

monomorphic

New Member

Smallest

Moderator

Nuka

Member

TerribleT

Member

sebastian

Active Member

Kor

Member

sebastian

Active Member

TerribleT

Member

sebastian

Active Member

monomorphic

New Member

Similar threads