- Gender and Relationships
Dating Advice for Cross Dressers
I get many guys telling me they wish they’d know more “women like me” who like cross-dressing men. One of the most common questions is where they can meet women who are into crossdressing and how they can get dates with them. Here I’ll give you cross-dressing boys some dating tips based on my own experience with cross-dressers, what I know about most women and what I’ve picked up from stories I’ve heard about relationships with cross dressers.
It seems that many have the firm belief that it's virtually impossible to find such women but read on and see why can and should be more optimistic. Is it easy? Of course not but finding a good date never is. I honestly don't think that cross-dressing stands in your way of dating success. Read on to see why:
Women who Love Cross-dressers
I’ve done some research on various polls and forums and from what I can tell there are plenty of women who would be willing to or already have dated a cross-dresser. In fact, probably most women have dated a cross-dresser at some stage even if they didn’t know it. Of course, you don’t just want someone who ‘tolerates’ you wearing women's clothes. You’re looking for someone who appreciates and loves that side of you. There are fewer women like this but still enough to go around and you shouldn't settle for less. But, other than being encouraging, that information won’t help you much as we’ll see further down.
Another point you might want to be aware of is that many women (and men) still think cross-dressing men are gay. Many of those who say they’d never date a cross-dresser think that “cross dressers only go out with men anyway”. This persistent little stereotype comes from a lack of experience with cross dressing men.
How to find women who like cross dressers
So let’s explore some of the possibilities that are open to you for meeting and dating these women:
1) Specialist Dating Services
In today’s times you can find online dating sites that cater to certain kinds of people with particular preferences. For example there are fetish dating sites for people who have a particular kink and there are dating services for people who seek a dominant or submissive partner to go out with. Likewise you can also find dating sites for transvestites and transgender people.
But you should know that many of them seem to be catering to straight men who want to go out with a feminine or cross-dressing man. I know it’s surprising but that’s the way it is. So you must make sure you find a site that caters to you and tries to hook up cross-dressers with women who love cross-dressers.
Also, you can expect that not many women would join such dating services. There will be some so it might be worth looking into them, but this is certainly not the best way to find CD friendly women.
2) Costume Parties
There are two sides to this one. On the one hand, costume parties are a great excuse to have fun going out in women’s clothes. You can openly show this side of yourself to the women you’re chatting up and they’ll have a clear picture of it when you finally tell them that you are a transvestite.
The downside is that there is no way of knowing if any of the women you meet are particularly into transvestites. I know it seems logical that such women would go to those kind of parties but that’s not how women typically go about dating men. And dressing up is always fun for women so there are plenty of reasons for going to costume parties without having ulterior motives.
3) Crossdressing clubs and gatherings
These are great for living out your clothes style just the way you want and having fun meeting like minded people. If you’ve ever been to one then you’ll already know that there are few single women at these places. That doesn’t mean you can’t find a date there but it will be hard. The great advantage is that those women who are there will definitely be of the kind that like cross-dressers. Still, I think specialized clubs and meetings are best for meeting fellow cross-dressers rather than dating women.
4) Going out dressed with a ‘hint’
My boyfriend used to do this and I’m not surprised it didn’t work. Basically you dress normally but with some elements of femininity in your appearance. For example you could wear tight fitting jeans or the subtlest of make-up. Or you could wear a girl’s top in some light color. It’s not that I don’t like it, but the problem is that people will almost certainly assume you’re gay which doesn’t help you find women who take you seriously. No matter how subtle you are about hinting some femininity, women will notice it and they will read into it - probably not what you want them to read into it. As for men, you’ll notice them starting to make advances toward you. So one reason I don’t like my boyfriend doing this, is because he gets eyed up by guys a lot.
It might work but more often than not, it will backfire.
5) Make your own woman who loves cross-dressers
This is by far the best and most promising thing you can do. Just date many women without revealing or hinting anything about cross-dressing. Then, once you’ve started to get close and she shows a lasting interest in you, tell her about it casually. The majority of women who like cross-dressers don’t even know that they do. That’s how I got into cross-dressing men. This also sorts out the problem with convincing women that cross-dressers are straight. It is very important to do it the right way and so I wrote a detailed article on how to tell your girlfriend that you cross-dress.
This also has a nice little side effect for other cross-dressers: You’re ‘spreading the word’ that cross-dressers are great partners and that they are often straight.
From the other side of the fence
Since I’m one of those women who love cross-dressers, writing this article made me think what I would do and where I’d go if I was looking for a date. I suppose, I’d just meet people the conventional way and take it from there. I’m confident that many men would like to cross-dress and so I wouldn’t go to special meetings or clubs to find them. Also, I love the thought of turning a man into a crossdresser – meaning that it’s me who introduces it to him and gets him hooked. It’s kind of like popping his cherry. I’ll be the girl who feminized him and he’ll never forget that. On the other hand, having him willingly share such a secret with me is a great sign of trust and intimacy. Don’t know if that makes any sense now.
But remember all women are different and what works for me won’t work for the next. The rules change with every person you meet.
I’ll update this article if I hear more ideas. As always, I greatly appreciate you telling me about your experiences with dating.
Also check out: