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Dating Advice for Cross Dressers

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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.

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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:

Women who like men in womens clothes


Bill on April 08, 2012:

Hi Lucy my name is Bill and i have ben crossdressing for a good time now.Crossdrressing came to me from a great women named Deb.I met her at a bar at the age of 21 i was a ass to women i looked at women as nothing more than a pice of ass at this time in my life. Deb was a beautifull sexy women and when hit on her she tunerd away. I was not one to give up so quickly (i was not use to being shot down)Deb did start to talk to me and than she asked if i would like to walk her home.when i walked her home she told me to meet her there about 10:00am and we could talk some more.Well i was looking get this women between the sheets si i meet her in the morning. like i sead i was a real ass at this time in my life i didn't have any respect for women at all and Deb knew this she also knew that all i wanted was to get into her pants and she didn't take any time on leting me know.Deb told me if i wanted to have sex with her i would have to do what she told me,i was up for it.Deb than had me make her eggs toast and coffie. while i was doing this i thought i was going to be her slave for the day and we were going to have sex and i was going to be on my way.Boy was i wrong when it was lunch time Deb told me she was going uot to lunch and when she got home she wanted me to do dishes vacum the floor sweep mop and dust and if i was a good boy i would get a surprise when she got home.Deb was gone for about 3hrs and i was takeing a nap on her couch when she got home i fineshed what she wanted in like 1-1/2hrs so i got a good nap.Deb had a larg paper bag in her hand and she told me i did good work it was about 4pm at this time.Deb told me i think you should start dinner but you need to change first.i asked her change what?Deb handedd me the bag i looked into the bag and it had 2 long gowns pantys pantyhoes bra 3 pars of open toe heels and a full slip.i said to her what's the hell is this?deb told me befor you can have sex with a women you need to know how to treat a women and befor you can know how to treat a women you should know what a women feels like and what a women must put up with from people like first i felt like droping that bag and telling Deb to f off.than i told Deb ok this could be fun i put on the cloths and came out the red gown fit me real good ans the frist time i crossdressed it felt great and i had a instent hard on.then Deb told me i want you to know what its like to be a women with an asshole in her if you feal like you want to leave at anytime tell me.Deb took my man clothes and loked them up.Deb started to yell at me about dinner and why the fuck it was not even started i made dinner she barked orders at me and as i brought he what she wanted she would grab my ass and smack it.we didn't have sex that night and i fealt as if i was not ever going back to see Deb agan ,but i kept going back and evry day for a month i was there dressed in drag doing thangs for Deb.deb showed me how it was and how women feel and i was no longer the same person i was a month befor.No Deb and i did not have sex ,but i did make love to her a lot. Deb moved away about a year after that we stayed friends for a long time. 5yrs ago Deb passed on from a car accedent.she will always be in my thoughts and evry time i go on a date with a women i tell he about my crossdressing befor the date is over becaues one thing that Deb did drill in my head is that the truth is the only way to feel good about yourself.i have never gone on a date with a women that dident accept the truth about me crossdressing most women want to see right away and be part of it some just smile and say you would make an ugly women and some women get realy tuned on by the thought.In my thought is just tell the truth otherwise you would be hideing the truth from the women and that's not far to the women your with and not far to yourself. p.s. With love to the women who set me free from myself Deb

Kathleen D. on March 28, 2012:

I went shopping with my boyfriend and finally got him to go to a local dept. store lingerie section to pick out some satin panties. He was always reluctant to shop close to home-but the girls at the store were fine with it. This was in Davenport, IA. so it's not like a big city. Next up, he gets a waxing from me! He always wears panties on our dates,and sometimes a bra under a jacket, but never anything that would show on the outside. He's a pretty big guy and no one would ever guess. I love knowing it's our romantic secret.

Lucy83 (author) on June 09, 2011:

Hi Tiffany and thanks for your feedback.

It's sad that so many guys out there feel they can't find women who would accept them. I also can't understand how so many stay in relationships with someone who won't accept them. To me that would be worse than being alone but many men seem to prefer living a lie.

I keep saying if more men would just insist on their right to wear what they want, more women would appreciate and respect it.

I hope you find what you're looking for. It's definitely out there.

Tiffany Louise on June 07, 2011:

I wrote about your article on my blog.

Tiffany Louise on June 07, 2011:

Lucy. Thanks for your article. It gives me hope that there are a few GGs out there that like this sort of thing. They are few and far between, but the number is not zero. i currently married to woman who "married a man for a reason." It gives me hope that one day there may be a small chance to find a GG that would want to play with me.

Kathleen D. on May 16, 2011:

just a comment about shopping. The stores are much mor eopen to a guy buying women's clothing if he has his girlfriend with him. Lane Bryant stores let me go into the changing room with my boyfriend. I really enjoy shopping with him. I also like to surprise him with little gifts like new panties. I would never date a guy for long if he wouldn't at least wear panties for me.

Lucy83 (author) on February 24, 2011:

Hi Kathleen,

yep, I love shopping for him too. I love deciding what he will wear and then I get to enjoy the view.

Kathleen on February 23, 2011:

My boyfriend only wears womens lingerie for special occassions. It's always hidden under his regulay man clothes though. For my birthday and for Valentine's Day, he wore a bra, panties, garter belt, and stockings under his suit when we went out to dinner at an elegant restaurant. When we got back to my apartment, i couldn't wiat to jump his bones!

(We go shopping together for what he wears). That way I get to pick out what I'd like to see him wear.

Assassin Fred on January 07, 2011:

Honesty is the best policy. First be honest with yourself. Ask yourself, can I live without crossdressing? If no (most CD's will say no), then you know that your only option is to be honest with your girlfriend or wife. If she doesn't like it or disaproves, then your relationship will not work, or you will both have to come to an agreement between you both. what is acceptable, what is not. Most women aren't out there looking for a crossdressing guy. The majority of women who love their crossdressing husband / boyfriend, were introduced to it, probably initially shocked, but realized it was ok, and they like it.

Steve on June 19, 2010:

and i forgot to say thanks a lot! at first i didn't know how many articles u wrote but now ive read a bunch of them.


Steve on June 19, 2010:

im 14, completely straight and i like to wear tutus. one time i said i lost a bet (which i didn't) and a girl gave me a tutu to wear which i kept for a 2 weeks. i wish i still had it. i do not want to tell any friends or family that i like too crossdress. i wuz wondering how i could buy or get a tutu without any1 really knowing. i hav thought about just asking a girl for and old one that she didn't need anymore but i dont want it to be weird...

do u hav any ideas on how to get one?

Jackelmex on May 17, 2010:

hey lucy. im new at crossdressing and i was wondering about when to tell my parents. my sister is a supporter of gays and bisexuals. i am a bisexual 15 year old. also i need help figuring out how to keep crossdressing a seceret from my parents yet keep crossdressing. i read in one article that i should get a girl who i can trust. and for further in formation can i get ur email? mine is

Joannne from Albany NY on May 10, 2010:

Hi Lucy. If you met me I wouldn't convince you that I was female either. I'm 6'3" and hence only go out to CD events. Women at those events are very few and the ones there are usually wives or girl friends of other CDs. The meeting I was talking about was on-line. Over the past 7 years or so, I have met about 30 genetic women that like CD's. Of those, I chatted regularly with about 14 of them. Of those, I got to know 7 well enough that we talked on the phone and of those 7, I only dated one. Her and I clicked right from the beginning and I ended up marrying her. Sadly, she passed away.

The point I was trying to make is that I only want to date women that are interested in cross dressers. Otherwise I keep thinking to myself during the dating process, "Should I tell her now?..Is she going to freak out?" Meeting them as a CD upfront takes that away. We can them move on to the other relationship stuff and can start seeing if we have other things in common. (Yes mutual love of cross dressing is not enough.) The net has changed though since I last looked for women who like CD's. 6 or 7 years ago, AOL was full of people and you could find lots of people with similar interests. There are a lot less people on AOL now. This blog was just what I was looking for.

Thanks for the response. Keep up the good work.


Max on May 10, 2010:

hey lucy. im new at crossdressing and i was wondering about when to tell my parents. my sister is a supporter of gays and bisexuals. i am a bisexual 15 year old. also i need help figuring out how to keep crossdressing a seceret from my parents yet keep crossdressing. i read in one article that i should get a girl who i can trust. and for further in formation can i get ur email? mine is

Lucy83 (author) on May 10, 2010:

Thanks Joannne! So you really get better results dating women as a woman? That is really interesting. Do they believe you're female. I've never met a CD who convinced me that (s)he really female. Perhaps from a distance but not up close and definitely not when I hear their voice. The only ones that make me wonder are teenagers who aren't fully grown yet.

Why don't you write your own article on it and then maybe I'll have to revise some of what I thought I knew?

Joannne from Albany NY on May 09, 2010:


I have tried making my own woman who loves cross dressers with mixed results. I would date a woman. We would be moving along ok and I would ask her opinions about feminine men, etc. Depending on her answers I would either tell more or less. What I tend to get in those situations are women that like you and might accept the dressing but don't enjoy it.

My best results is looking for women as Joanne and if they enjoy this side, tell them about my male side. There is nothing better than being sexy for an appreciative woman.

The hard part is that women that like CD's are few and far between but unless you get out there you won't even find them.

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