How To Tell Your Girlfriend You Cross Dress

I hear a lot of sad stories of cross dressers in relationships that restrict or completely prevent them from doing their thing. The best way to get out of such a situation is to avoid getting into it. I know, that’s not much consolation to those of you, who are already in it, but I might help giving you a fresh perspective too.

Lets Get Things Into Perspective

First of all, you do not need to apologize for it, you do not need to feel ashamed of it and you do not need to ask anyone for permission to cross dress! Dressing in women’s clothes is as harmless as anything and you don’t need to think of excuses or explanations for it. It is your right to do it whenever you want. Anyone who tries to deny you that is the one who needs to apologize and explain.

Also, don’t let anybody make you think it's a form of perversion. It is not - even if it turns you on (and that’s a good thing). Lots of things turn people on that seem to make no sense; that’s how nature works and we are a part of it. In many cases, I think men dressing up in women's clothes is an expression of a highly charged heterosexual drive. Such men are so obsessed with anything feminine, that they literally want to get right inside it, be surrounded by femininity and have it engulf them and melt with their personality. This is as male as you can get. If anything, you should be proud of it since that is the same force that kept our species alive.

My point with this paragraph was to make it clear how you should and more importantly, how you shouldn’t feel about cross dressing. This sets the ground for everything else.

She Forbids Me To Wear Female Clothes

This is, unfortunately, quite common. I have to say, my CDs, I just can’t bring up any sympathy for a person who lets their partner forbid them to wear something or forces them to wear something they don’t want. Its one thing for her to say: “you’d better not wear that tutu for your job interview” because she’s caring about you and warning you of the consequences that could harm you. In fact, its her duty to do that. BUT, if she tells you that you can’t even wear the tutu in your own home, then it has nothing to do with care and only about some twisted preconceptions that she has about men wearing tutus. That is HER problem or perversion and it is SHE who needs to work on it, not you. If you give in to such a demand, then you’ll set the standard for a relationship that will hardly work for anyone. Remember, even bossy people (like me…cough) don’t like men who won’t even stand up to their most basic human rights. I’m sure that some 99.9 % of such relationships go horribly wrong eventually.

Here are some possible answers to that demand (not necessarily in order):
1) Get lost

2) F*** off b**** (I don’t recommend that one)

3) Go find someone else to be your slave (this could end your relationship. Just thought I’d warn you)

4) Ok, I’ll stop wearing skirts if you never wear trousers again (hmm, what if she agrees?)

5) I’m sorry, did you say something?

6) Honey, are you ok? Perhaps you should get some professional treatment.

When To Tell Her about it?

Sooner rather than later. Of course the exact timing depends on your situation but the earlier you do it, the easier it is. With me its different. If I was to date someone, I’d be the one asking them because I like transvestites and any man who’s scared of trying that is just boring or something worse. But most girls either don’t like it or don’t know that they might like it. So you have to give them a chance to deal with it early - for your own sake too.

The best timing in my mind is after you've made some kind of positive impression on her (i.e. you're already dating officially and she wants you) and before she has a fixed picture of who and what you are (i.e. when she's still getting to know your main character traits; so she's still expecting surprises). You should know she'll probably figure your personality out sooner than you think. Most women play a whole load of tricks and games to test their new boyfriend and his reactions to situations while he often has no idea this is happening.

Keeping It Secret

This is the biggest issue for most transvestites. How, when and if to tell your partner that you like to wear a fairy princess dress at night or whenever.

There are too extremes. Tell her when you first meet and, the other is to never tell her and do it secretly for perhaps the rest of your life. Both of them are pretty bad but the second one is a disaster. If you tell someone on your fist date about this, then she’ll probably run a mile. Just take my word for it. Girls know that you show your best manners and hide your worst during the fist date. So, in her mind, if you’re openly telling her that, then you must be hiding something FAR worse.

There are many good reasons to hide this from the outside world. I’m sure you know them all. But there are NO good reasons to hide it from your girlfriend or wife. This is just one of those things you share in a relationship. What’s more, one day she’ll find out and then she’ll feel cheated and betrayed and she’d be right to feel that way. Besides, hiding cross dressing as if its a dirty secret, must tare you apart inside over the years. Give her the truth. If she's worth anything then she deserves it.

How To Tell Her About It

Overall, try not to make it seem like a big deal. If you’re afraid of asking directly, you could find a way to bring up the topic and test her opinion. But avoid the classic “I have a friend who wears women's clothes. What do you think about that?”. She’ll see right through it.

You could for example, watch a movie that has a drag scene and discuss the movie afterwards. Or you could take her to see Cinderella (the three ugly sisters are always played by male dancers – don’t ask me why).

Still, I think telling her directly is the best way. She’ll respect your honesty (at least she should). It is a sign of trust and intimacy to share a secret like that with her. Lots of women I’ve heard liked their boyfriend’s or husband’s transvestism because of that more than anything else.

One good way to tell her, is to mention very casually in passing that you've worn women's clothes before. Something like:

1) "Years ago I had a phase where I was trying crazy things and one of them was to wear women's clothes".

2) "When I was younger, I was curious about women's clothes and wanted to know what it feels like to wear them. It was interesting..."

Say it in a way that is likely to make her ask for more details (such as if you still do it). When she does you can continue with something like:

"Well I still have the clothes somewhere but I haven't bothered with it for a while now".

This could be a very good way to tell her because you're not sounding like you have any kind of issue or problem and that is her biggest concern. I bet that's what most crossdressers do wrong when they tell their partner. They get hugely worked up and say, with a trembling voice, that they have a big dirty secret and basically make it sound like they're some psychopath. Remember guys, most women don't listen to your words in an objective way. They rather interpret your emotions as you talk (i.e. HOW he's saying it is more important than WHAT he's saying). Of course there are exceptions but they are rare. Take my word for it.

There is another way to introduce it to her. You could suggest to her that you're willing to do the household chores dressed in a maid uniform. I wrote more on that in my article on the sissy maid. Trust me, most women will be very open minded if the reward is that great.

Another way to test the waters is to point her to a story like this one about transvestite beauty contests and see how she reacts.

Final Thoughts (for now)

Remember, all of this is not a big deal even if it feels that way to you. Its nothing really – wearing clothes of some kind. So telling your partner about it should also not be a big deal to either of you. Only she can make it a big deal by freaking out, or forbidding or name calling. But if she does any of those things, then you know that she wasn’t worth any effort in the first place. That’s another reason to tell her early, so you don’t waste time on a bee with an itch. I wrote another article with dating advice for cross-dressers.

Please share with us your thoughts and experiences. Have you tried any of these? Or perhaps you have other ideas to add.


More articles on crossdressing:

Celebrities and Crossdressing

The Beauty of Crossdressing

Top 10 Myths about crossdressing

Try dressing up as a woman

When crossdressing becomes problematic

Adorable Crossdressing Outfits

Comments (copied from Hubpages)


I have a 15 year old that I know has been cross dressing and I don't know what to say to him. Please help!!!


Well how do you feel about it?

If you want it to come out into the open you need to give him the impression that he can talk to you about it without worrying. For example, wait for an opportunity when the topic comes up independently (i.e. if you're watching some TV show or movie that touches on it), and hint that you don't mind it at all (for example by saying something like "I don't see why people have a problem with guys wearing women's clothes"). If the opportunity doesn't arise, you could make it arise (by saying for example, that you saw a man wearing women's clothes the other day or that you knew a friend once who did this). If the situation is loose enough, you could also just ask him casually if he's ever tried it. As long as you never make a big deal of it, he should eventually come out openly.

How about other family members? Do they know?

Remember, it isn't a big deal. As long as he doesn't do it obsessively and as long as it doesn't affect his social life.

The biggest and most common problem in families with crossdressers is that the other family members feel strongly about it and artificially make it a big problem.

And don't worry about his sexuality because that's been hardwired into him for at least 10 years and no amount of wearing clothes will affect it.

Mara Sophia

More than once I have talked to my girlfriends about my preference for crossdressing during the first dates. One of them after she had not doubts about my heterosexual drive simply ended loving it and asking me to wear this and that. She gave me a set of her own matching bras and panties for me to wear all the time. I had serious problems with my wife, she never accepted the idea and eventually was one of the reasons (not the only and main one)for our breaking-off.


Thanks for your comment Mara. Sounds like you're better off without her. Fortunately there are plenty of free women out there.


That's a GREAT Hub, Lucy. I wished i had read this years ago. I do appreciate the support and enjoy reading what you have to say. I wished there were significantly MORE Women out there like you who are that supportive and don't mind being who you are


You know I can imagine that there are quite a lot of women who would be fine with it if they just knew more about it and were told the right way.

Before my bf told me, I had never encountered crossdressing other than in comedy acts. Though I never thought of it as something bad, I know that I would have reacted badly if I'd just caught him. So if it weren't for him and how he told me, I might have never liked it or even hated it. Instead I love it and would want any boyfriend to be prepared to wear women's clothes at least once in a while.

I'm amazed at how many guys appreciate that I like it even though they know nothing else about me.


i want to break up



This is you best post. This is especially when you said: "First of all, you do not need to apologize for your it, you do not need to feel ashamed of it and you do not need to ask anyone for permission to cross dress!" Thank you.


Good article. Myself i never had too much of a problem with cross dressing/relationships. I will say i aren't a full time CD but in terms of under garments and so on, i am. So it isn't as "standing out" if that's the correct way of saying it. But in general no one has really bothered.

I like the way you describe Cinderella and the three ugly sisters. Truest words possible.


I enjoy cross dressing.It used to mean the world to me. If someone told me to stop I think that I would have felt like it was the worst day of my life. i dress up when I am alone or when I go to glbt events. I am bisexual and I usually were girl jeans and girl underwear with a t shirt, when |I go shopping. It doesn't freak people out,but it shows that I am different. I think that people think that I am gay, but don't care. I like being out of the closet and I am looking forward to finding a nice girlfriend or boyfriend who will understand, and not make such a big thing about it. Its just like you said their just clothes.

From sisy


i haven't seen my gf in a week i really want to tell her that i occasionally crossdress in private before/during masturbation. I'm seeing her tonight for a little, then tomorrow all day. Should i do it tonight? I really like the way you said to tell her about saying you did it a bit in the past.


You must know yourself when the timing is right. See what sort of mood she's in and if she's prepared for something like that.

Generally sooner is better than later but that doesn't mean it has to be today rather than tomorrow or the day after.

Please let us know how it went when you do tell her. And good luck.


Hi Lucy, another great hub.

I told my girlfriend on our fourth date. For our previous date I had worn a pair of plain black boy leg panties & a silky black microfiber singlet-cami top. When we were making love on that occasion she made no attempt to remove either, so I plucked up the courage to tell her on our next get-together.

As we were sitting together, I said to her “XXXXX. I have something to tell you.........I like wearing lingerie”.

“Oh God!” she replied “Is that all? I thought you were going to tell me you were seeing other women!” I then removed my shirt to reveal a white silky camisole, stood up and dropped my pants, showing her my legs clad in high gloss, silky nude pantyhose & a white satin thong with a little lace trim. She stood up, ran her hands over my legs, then she put her arms around me, kissed me and brought her right hand around to stroke my chest, kissed me again and said “Mmmm, feels nice!”

Since then, lingerie has been an almost permanent part of our love-making. The first time after that night that we made love with us both wearing stockings, the moment she felt my nylon-clad leg caressing hers she exclaimed “God! That feels horny!”

Her husband of 20years had been your original Mr. Vanilla – wouldn’t even entertain the idea of looking around in a sex shop and a “3 minute wonder” to boot.

A couple of weeks later she discovered another advantage of dating a lingerie wearing man. I took her shopping in a favourite lingerie shop of mine, selected s few bra/panty sets for her to try and when we found the one she liked best, I bought it for her. Her ex would stand around looking embarrassed at the very edge of the lingerie section if she was buying any underwear for herself.

Having felt ashamed and embarrassed about this part of my make up for too many years, her open attitude has been a great help to me, to the extent that I am now in a place I never thought I'd arrive at - that I can walk around my house or sit with her dressed only in lingerie & feel totally relaxed & unselfconscious.

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