When is the right time to tell GG you're a crossdresser

Probably we had this kind of thread already, but I couldn't find it, so I'll ask.

When is the right time to tell a women (GG) that you're a crossdresser? If I tell soon after I meet her, that could scare her off before she really has a chance to get me know better. If I wait, she might resent not telling her sooner? What is the best approach? Underdress or use subtle makeup and let her discover and ask about that her self?

Also any suggestions how to assure her you're a real man, but you just like to wear female clothes?

I wish I had an answer for you but every situation is different and not all women will react the same way. Trust your instincts. You might want to ask subtle questions and guide conversations to get a sense of what her reaction might be.

To some extent it depends on how "crossdresser" you are. Is it a primary fact of your life? Or is it something you feel is your identity, but not your purpose for living? Whatever your level of crossdresser-ness, I'd say wait until you're at the stage of the new relationship where you guys are sharing that level of detail with each other. In any case, I wouldn't let the relationship get to the point where you're going to be destroyed if she can't deal with it before disclosing.

I underdress all the time, even for work and dress at home, but officially I'm still in the closet and dressing is not part of my social life. None of my coworkers, friends or family know, I think. Sometimes I also go out by myself fully dressed. I think I would like things to stay like that in the future, except going out. That would be awesome if she would like to go along. I guess all of this I would like to share with her. I don't want a relationship where I should hide my clothes around the house and dress in secret, so I need a women who would be ok with me dressing, hopefully know how to enjoy that with me.
I'm wondering what is the best way to introduce my secret in best way. I know, if she doesn't like it, I can't help, but if she is one of those who don't really have an opinion on this matter yet, how to introduce this to her in best possible way at best time possible.

I am in neither a marriage nor a relationship; so you might want to decide whether my opinion is worthy of your time.

Although I made no attempt at marriage for this very reason; I have thought about it a lot. It's like: what's the best way to make a 100ft jump from a building? The chances are not good to begin with, and whichever way you do it, you still have to survive a 100ft drop. So I thought maybe early might be good. As you said, she would probably be scared off before getting a chance to know you better...

Good!

The better she knows you and the more integrated she is in your circle, the more powerful that knowledge could be to her. ( Discrete Discreet women that would not out you on breakup do exist ).

So my thinking is to end it early, save time, and move on. However, the issue with this is that: 1) You could potentially end up telling more people than if you wait. 2) You also waive any chances of warming her to the situation, but this is only a factor if it happens at the first attempt. Otherwise there will be ex-girlfriends who know about you who also know people you know, which neutralises any future advantage of trying it again with future GFs.

So . . fewer women that know many of your acquaintances, or more women that know none? :idontknow:


It also depends on how highly you value SO acceptance. To me, I wouldn't have been able to have lived without it.

But as I said, I am not married.

- Lydianne.

For me I say within the first couple of times you meet. It creates a trust factor that’s very important.
That’s my advice

I would say that it depends on how important your dressing is to you and how much a part of your life it’s going to be. If you are dressing quite often and you want a partner that will actively participate in that aspect of your life, I’d say be 100% up front right off the bat as that will save you a lot of time and trouble. If it’s maybe an occasional thing to you and maybe you’re ok with a DADT kinda situation that maybe wait until you’re sure the relationship is going somewhere before breaking out that secret.

I agree with Tracy (#2). If there are venues in your area that are transgender friendly start frequenting them. Maybe you will encounter an unattached woman there. I would conjecture an unattached woman in such a venue would be more accepting. If you're dating a woman take her to such a venue. In general conversation it is possible to get a true read on somebody's acceptance or non acceptance. You're right that a woman may be scared off by your cross dressing before she really gets to know your qualities. Some women will find cross dressing to be a deal breaker no matter how great you are otherwise. Of course women can change their mind. A woman may be intrigued but later grow tired of this aspect of you. Life can be a crap shoot. Good luck on your search.

Here's my take, if your not really out of the closet, or looking to be, then I would wait a few months down the road, like 6 if your unsure where the relationship is going. there is a saying in these parts that once the cat is out of the bag, you can't put it back in and there no need to tell them if it isn't a long term relationship. Trust isn't built over night and only a fool thinks it is.

No matter what though, you should tell them if your planning on getting married at some point. There is no way anyone should get married with this secret. Some, the CDing didn't develop "full blown" until well into a marriage but even then, most of this starts at a young age so you know it's there. Some even think getting married will be the cure all that never works. so before getting married is most certainly the time to come clean so she can walk if she chooses and you can save all the BS that comes with divorce.

As to how to tell her? everyone has had different routes they have taken, I suggest just a straight drab sit down and talk. Communication is key to any good and healthy relationship and this is no different. Do NOT do it dressed, just pop up dressed, or even under dressed. That, to me, is like forcing it on her or shoving it in her face and it probably won't end well. Sit down and have a serious long talk and answer any questions/concerns she has and go from there.

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Originally Posted by Karmen

I underdress all the time, even for work and dress at home, but officially I'm still in the closet and dressing is not part of my social life.

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So, it seems likely you'd want to disclose before that top layer of clothing comes off, right? I don't know what the culture is like in Slovenia, but in the US that's usually pretty early in the relationship. No matter which way she reacts to the revelation, you have to be prepared that the information may travel -- so consider who else you might want to disclose to before it gets out or at least have a plan for dealing with it.

I think Tracy is spot on on this one. If you wait you'll probably sense a time that is appropriate to let the discussion go in that direction. Remember go slowly though is my suggestion but don't go into the relationship so far that if she was not into it that every thing explodes. I'm thinking if she really is in love and y'all are soul mates then the relationship will last regardless of what she finds out. Lydianne did make some valid points to consider also. Good luck.

Simple....assess the situation and go for it accordingly. Does she knows anyone you know? Otherwise you are you and crossdessing is part of you. What someone thinks about you is none of your business. Looks like a promising relationship? At that point...tell her.

I was successful, but it took me almost 30 years before my wife and I had the discussion. You may want to avoid that timeline.

My recommendation has less to do with your relationship with her than it does with the level of confidence you have in yourself. If you tell her and she rejects you and then tells her friends and your friends, you better damn well be ready to face the world. If you tell her and she says it's just fine with her, then you better be confident enough to dress around her. Good luck.

My wife of 20 years knows all about my crossdressing, but there is a chance that we will not stay together now that my son is away at college (not because of my CDing, although obviously that's one element in our complicated marriage), so this is something I've given some thought to. My feeling is "As early as possible." For me, this would be unavoidable because I wear women's clothing more or less 24/7 -- not skirts and dresses all the time but capri pants, tights, women's sneakers/sandals/flats, women's tops, etc. My hair is in a bob just below my chin and I wear a headband nearly every day along with earrings and light makeup. So it would be immediately apparent -- and, no doubt, a conversation starter!

I believe you owe it to yourself and to her not to spend a lot of time with her without being open about who you are and what you need. If that means she gets up from the table and walks out of your life, so be it -- that is the reality we live with. If she's willing to stay, even if she has objections or hesitations, then you've found someone who's open-minded, tolerant, and willing to explore & change. And that, as we all know, is rare.

Best of luck!

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Originally Posted by Pat

So, it seems likely you'd want to disclose before that top layer of clothing comes off, right? I don't know what the culture is like in Slovenia, but in the US that's usually pretty early in the relationship. No matter which way she reacts to the revelation, you have to be prepared that the information may travel -- so consider who else you might want to disclose to before it gets out or at least have a plan for dealing with it.

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Culture in Slovenia is much the same as in USA regarding to relationships. Clothes comes off very quickly too. I don't know if she knows someone I know, since I don't know her very well yet. She doesn't know my close friends and family, but I don't know if we have any of the same acquaintances. She is from the same city so we might have them. And I'm definitely not ready to come out of the closet yet, so I'm afraid what might happen if she would tell anyone that can tell to people I know. I don't have a plan what to do if that happens even now (if I get caught or something). I guess I would have to deal with that when it happens.

As some of you suggested, I think for time being, it is safest and definitely best to do as I done so far with previous GG. I'll wait with any disclosures and wear male clothes only when with her for time being. Will see where things will go. It's a fresh relationship, not even sure if it will last. In the meantime I'll try to find out her general opinion on this matter through some random talk when is a chance.
It just scares me I will wait so long, because I won't be sure or find the right time to tell, I won't have the courage to come out clean any more. That staled and eventually killed all my previous relationships. And with amount of female clothes and shoes I have it's a challenge even inviting her to my apartment for more than a short time. If she would open the wrong wardrobe, I would have some explaining to do right away.

Thank you for all the help! If anyone have any more helpful tips, I will be happy to read them.

I was dressed en femme when I met my wife, 16 years ago. She later told me that she was intrigued, she looked deep inside herself and saw no problem with it, in fact it looked like something new that she could have fun with. We became girlfriends, then lovers. As we are today....
I don’t think my wife is unique. I think other women would share her view, if they had the information, and keeping it from them might feel safe but might not lead to the best outcome, as my own life experience suggests. I took a chance being out with it, hoping I would catch the eye of such a woman, and I hit the jackpot. No advice can be given, only you can assess your situation, but I do wish you both luck and courage however you decide to proceed.

On your 50th anniversary :D
Seriously my opinion is, sometime before you get married, that way she has a choice from the beginning to accept this or not before a true commitment is made.

Jackie7, you were lucky to find women like that.
In small countries or towns if you don't want to get caught and outed sooner or later, you can't socialize much fully dressed. You can go out dressed, but you have to avoid places where you meet people from eye to eye. I risk a lot even when going shopping, but there you can always say you're buying a present for a women who is the same size as you or clothes for a party in masks or something. If you get caught in a club or on the street fully dressed on a normal day, there are no excuses. So, there is not much chance for me to meet a women that way.
As all others, the current one, I met dressed as a man.

Your comment about shopping reminded me something that happened just a couple weeks ago, I was in CVS, a drugstore in the US, I was buying makeup and pantyhose. I went up to the counter and the guy running the register looked at me funny, I smiled and told him, this is why you never tell your wife, "I'm going to the store, do you need anything?" He laughed, and it killed the tension.

GG chiming in here :

Tell her as sooner rather than later. If she doesn't like it or can't cope then the break will be easier than what it would be further down the line.

What about the risk of exposing me to the world if thing don't go as planned? I know it can happen in both cases, but if I tell later, I'll have more time to evaluate the situation and her character and decide, if she is someone who can keep a secret or not. Of course I agree that should be before any real commitment like moving in together or marriage.

And if you do it later and things don't go as planned, then you risk her exposing you to the world and more people that you both know, with more ammo. And you lose a more developed relationship when it comes to an end.

Indeed it's a balancing act, but the thing is, before you tell her and you go about building other parts of your relationship, she will be fully invested in trying to make it work, but you will only be in with one foot while you assess her suitability to keep your dressing a secret. How invested can you truly be when you know the foundations are not fully set and there's potential for it to all crash down? Only you can answer that. I know I couldn't do it.

I've thought about this stuff a lot, heh ;) .

- Lydianne.

That is a valid concern, Karmen, it kind of puts you in a position if you're dating someone and they know your secret. Will she out you?
The best advice I can think of is, if you really love her then you have to trust her.

Are you planning to get married or just dating. I would and did before it got serious. Some will walk away some will stay. But don't wait to long or she may tell all if she finds later.

I wasn't a full blown crossdresser when me and my wife says dating about 11 years ago, but did wear panties. I told her about that pretty early on if I remember right, maybe a month or two in. That's when things really started to get real in our relationship so I think that was the catalyst for telling her.