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

[Karmen]

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?

[Tracy Irving]

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.

[Pat]

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.

[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. 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.

[Lydianne]

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.

[Rachael Leigh]

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

[Micki_Finn]

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.

[Stephanie47]

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.

[~Joanne~]

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.

[Pat]

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.

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.

[Jaylyn]

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.

[Joyce Swindell]

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.

[Sarah Doepner]

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.

[TracyT]

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!

[Karmen]

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.

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.

[Jackie7]

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.

[StephanieM]

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.

[Karmen]

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.

[StephanieM]

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.

[Sandra]

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.

[Karmen]

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.

[Lydianne]

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.

[StephanieM]

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.

[Glenda58]

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.

[Victoria92116]

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.

[Karmen]

Glenda58, I only met her a few week ago. It's not serious yet, but it's past the stage of one night stand, that's why I'm considering how to handle this from now on.

[Kelly DeWinter]

Hmmmmm;

Jeannie and I discussed this and suggest
. If you are casually dating and the relationship is going nowhere, then no hurry , no disclosure needed.
. If you are friends with benefits , again no hurry.
. If it looks like its going to lead to something, then before 3rd base
. Before any kind of commitment

[Shayla]

Karmen, I think you have the right idea. No need to scare her off, but once some trust has been developed and you are starting to think longer term (if it gets to that point), then that is the time. Finding a way to talk about transgenderism and how she feels about it will also give you some insight as to when, or maybe not to... best of luck!

[kimdl93]

I’m thinking probably sooner, rather than later.

[Aunt Kelly]

Yes, this topic has been "done to death", but the frequency with which it reappears makes if fair game, IMO.

Earlier is better, always. As soon as it looks like the relationship is headed in a serious direction, it's time for "the talk". If you delay it, you are hiding something important from someone who has a right to know about it. You might try to purge, and convince yourself that you "won't need that anymore". It won't work.
Honesty, at the earliest reasonable point, is the best policy. Yes, you might scare someone away with this, but trust me. Life is too short to be spending it with someone who can not accept who you are.

Hugs


Kelly

[michelle64]

First date..if not your asking for issues later on....best she ejects you very early on rather that 3 kids house and dog later...

[Rachelakld]

We started to get serious on the 4th date, so I showed her my wardrobe - alternatively you could wait 20 years, lose everything and start again.

[Vickie_CDTV]

Ideally, when the relationship becomes serious (you appear to be there now.)
Certainly before marriage (and before you mix your finances.)
And absolutely, positively before you have children with someone.

In the long run, you fail to disclose at your own peril. You can read disastrous consequences of failing to tell before marriage all over this site.

[Cheryl T]

There is no "One Size Fits All" in this situation.

I wanted to tell my wife before we married, but I had done that previously with another woman and it ended the relationship during our engagement.
I was discovered and it didn't go well so I promise to quit (as many promise) and I knew it just meant back in the closet.
Then years later I told her that I hadn't, don't want to and wish to be open about it. It took a long time, lots of tears and discussion, reading about it, becoming a member here and also a support group before she became fully comfortable with it. Now she is fully supportive and helpful and all is well.

Each situation is unique as we are unique. No one can say what is right for you. Sorry, but it's the truth.

[CONSUELO]

I would suggest that as soon as the relationship with the GG becomes more than just a passing friendship you should tell the person about your being a cross dresser. If you don't tell you will have to hide it from the person forever or until she finds out. It is hard to do but I found it better to be open and honest from the beginning.

[Karmen]

I would tell her right away if that meant only two thing, her agreeing with my crossdressing and relationship will flourish or ending the relationship because she doesn't like it. I'm more afraid she will end the relationship and than tell someone about my secret. I will loose her and my life will be turned upside down, probably not only compromising my friendships with some strong minded people and make my parents upset, but my career can go down the drain too. I know, there is also a huge positive aspect too, since I wouldn't have to hide my passion any more and dress as I like all the time, but it's still something I don't really want to happen.
I also know, I can't stop with crossdressing. I tried that already twice when younger and I was miserable and started dressing again in few months time, so not telling her and hiding that from her on long term basis will also not work for me. I can hide it until we are only dating, but if in the future we decide to live together, I must tell her by than. Not only because that is the right thing to do, but also because I want to be able to wear clothes as I'm wearing now. Underdress on daily basis and wear female clothes at home every day, not only occasionally when she is not at home. It's just something that I'm not willing to compromise on it even for sake of a relationship. I learned from experience, because I done this compromise in the past and didn't end well.

[jacques]

my advice - never lie about it.
Always speak the truth, but you should not always speak!

[Karmen]

That is a good policy most of the time. Don't lie, but don't tell everything if not necessary. But I'm not sure if it would help in this case. What would be my defense when caught lying about "not living as normal boring everyday man"? Why you didn't ask me if I wear female clothes when you're not around? I'm sure that would make women more upset than a do good.

[Steph_CD_62]

I say every relationship is different, but I would have to say the sooner the better. Just put yourself in her shoes, what if she had a big secret would you rather know now or in 20 years?

I told my current wife when I first met her that I had a fetish for lingerie and within a week or two I had told her that I was a crossdresser. I gave her a couple days to think about what I had told her before I called her again and things have been pretty good as far as my dressing.

[Karmen]

You have a valid point, but would she tell her secret if she doesn't know if I'll tell that to the world? Tell her little by little, as you? Maybe that's a good way too. Better a lingerie fetish than a full blown crossdresser for a start. I just don't like the second part, where you have to put her on the edge again and wait, if she falls over the edge or bounce back to you. Two shocks like that might damage relationship, because she will be always suspicious what is the next secret she has to cope with?
Please, don't get me wrong, I'm thankful for every advice, especially those already tested in the real world, so I'm not criticizing, just thinking out loud about all options.

[Amy Lynn3]

Karmen, I agree with the majority here that you should confirm early on that you have found the right S.O. Allow me to recommend what I have done in your situation. I do what I call "Third Party" talking. In other words, when you have your answers and questions ready, ask this. Tell her you know a guy at work who dresses in female clothing at times. Allow her to react to your statement. If she reacts positive, you can continue with questions like, could you be happy married to a person who does this. You must be able to think on your feet and respond according to her answers, but you can find out how she feels without fear she will tell the world about you.

At the end of your conversation you can make up your mind to tell her about yourself or let it pass as just a conversation and think about moving on to the next lady.

[Karmen]

That's a great idea. Thanks!

[Joni T]

It's better to let the cat out of the bag sooner than later. It's easier to part ways before you've invested lots of time.
Jon

[sometimes_miss]

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?
She will resent you not telling her no matter what you do. The question really is, how MUCH will she resent it. No one likes to be fooled. And presenting ourselves as 'normal' men, while being crossdressers, is fooling her, or at least, that's how she will feel.

What is the best approach?
There is no 'best' approach. Each way has failed at some point, and despite all that we know, some that we would automatically think wouldn't work, have also succeeded. It all depends upon the woman, and how she feels about you.

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.
^Start here. Find out as much as you can about how she feels about gender bending behavior. You're basically going to have to either bring up the topic, or get her to some type of entertainment where there are crossdressers, transsexuals, and gay people involved. Why all those? Because she will automatically wonder exactly what you are, and will consider all of those as possibilities. Why? Because unless you can tell her why you are a crossdresser, she will come up with a reason on her own, and you probably won't be happy with what she comes up with. Me, I start slow. One new way is to introduce various comedy performers into our entertainment; At some point, I add Eddie Izzard into the mix, and see what she will say.
There are other movies with transgender/crossdresser characters as well. No, it's not easy to bring up the subject, but you can keep the concept alive by adding more alternative lifestyle characters into your entertainment. Look for some who offer jokes about us, and see how she laughs or doesn't at the TG character. Take it slow. THere's no rush.


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.
Well, always remember that the true number of people who can keep a secret is...................ONE.
And most women, when confronted with a problem, feel the need to talk to someone else about it, and NOT the person who is the one causing a feeling of conflict. That means unless you're already in therapy or she is, she's most likely to 'bounce the idea' off of one of her closest friends. And then, you're OUT. Because whenever someone else comes across a TG person, YOU will be used as another example to them.


And if you do it later and things don't go as planned, then you risk her exposing you to the world
&

But don't wait to long or she may tell all if she finds later.
That risk is there whether you tell early, or late, or even never and they wind up finding out on their own. Every woman is different. Some will accept us, some never will, no matter how long you wait.

my advice - never lie about it.
Always speak the truth, but you should not always speak!
That doesn't work either. We get accused of lying by omission. No matter that the woman might also not have told everything to US about themselves, they reserve the right to feel wronged for themselves.

What would be my defense when caught lying about "not living as normal boring everyday man"? .
There is no defense. We are what we are. And it's not about debating whether it's appropriate or not; women don't care about that. How THEY feel is all that matters.

Remember too, despite all the success stories you read here, the vast majority of women:
1. Aren't attracted to crossdressers. Femininity in a man is almost always a turn off for a woman. Once you poison the sexual desire, the romantic relationship is over. Don't wait TOO long, because YOU will get too attached and start to slip into the pink fog, and believe that the odds are in your favor, that everything good about you will certainly outweigh the fact that you're a crossdresser. It doesn't work that way. Crossdressing isn't just a hobby; it changes what she thinks of you completely. Why? Because you can quit a hobby; you can't stop being a crossdresser. It's like going AWOL from the army; you will forever be considered a deserter, no matter what else you accomplish. Being a man means a lot of things, and unfortunately, anything that makes her question your masculinity can make her see you as NOT manly, but as a girly man. Crossdressing, perhaps more than anything else, is a huge deal breaker for virtually all women. See the odds further down this post.
2. Are actively sexually turned off by the thought of a man who embraces femininity or feminine behavior. Dressing in pretty female clothing, to women, is reserved for FEMALES ONLY. Why? Because pretty female clothing is designed to attract men. Whether or not she admits that, or even tries to say that women dress to impress other women, it's quite clear that female fashions all work to accentuate the female figure and make the secondary sexual characteristics more obvious.
Now, why does this association with femininity upset women so much?
Because women rely on men for protection and support. They want a mate who is rock steady, stable, one that can be relied upon to always, always do what she deems him to be responsible for. Any time you do something that might make her question whether you will protect and/or provide for her, and she can lose any romantic interest in you in an instant.

No, it's not fair. But it is what we have to deal with.

FWIW, I date. I carefully work around the topics of sexuality, and gender, by exposing the woman to various entertainment and news topics, to see how she feels about it. This can take a while. If I find that she has any strong feelings that would indicate she could not accept a man who crossdresses, I simply start slowly adjusting my behavior, and try to get her to lose interest in me. This way, she will feel that it's HER making the choice that we shouldn't pursue a romantic relationship. I'm not mean; I don't want to hurt anyone's feelings. But I'm not going to allow myself to get hurt, either.

I have yet to find a woman who is both sane and accepting of crossdressing. A few have expressed that they were really okay with it, but it turned out that they were simply so desperate to catch a man, that they would say anything, and then try to change me later.

The percentage of women who really like the idea of her man crossdressing is in the low fractions of one percent.

What I read back in the nineties when I was really researching this, was that only six percent of all women think that it's okay for a man to crossdress, but they don't want to personally have anything to to with him. Three percent are okay with having a crossdresser within their family or friends, but they don't want one for a mate. And 1.5 percent would actually consider a man who crossdresses as a potential mate. What I found interesting was that each category was about half of the previous one (the stats aren't exact; but so very close that it is simpler to use the integers mentioned). In the late nineties, my wife and myself went to marriage counseling, and we had both individual visits as well as couple visits. During one visit, I brought up the information that I had found; and asked the therapist about it. What she said next, was that of all the couples she had seen, of the women who initially thought that they could accept a crossdresser as a mate, half again later changed their minds.

So we're looking at a 0.75% of the female population that would even consider a crossdresser as a mate in the long run. Now, you have to factor in whether she will be enthusiastic about it, or all the way to just barely tolerating it.

We've done lots of threads on accepting/tolerant wives/SO's/girlfriends. The number of women who actually like to have a husband who is a crossdresser is so few as to make those women so rare that you're more likely to win the lottery than find one.

Good luck. You're going to need it. I'm not trying to be negative; just preparing you for reality.

I've come to accept that i may never again have a long term relationship with a woman. So I try to enjoy the short ones while they last, and move on without feeling like life cheated me somehow. The vast majority of relationships don't last for life. So enjoy what you have, while you have it.

[Beverley Sims]

How long is a piece of string.

Get the matter settled before you get too deep into a relationship.

It is easier to break out of the relationship early if you do.

[MLane]

I would wait and ease into it the conversation as more of a discussion and opinion, see where she stands on the topic before putting yourself out there.

[Wallaone]

I can't imagine waiting is a good idea considering you feel crossdressing is important in your life. There are probably several methods to open up dial as stated above. If she's the one for you, waiting would likely undermine her ability to trust you with sensitive and personal life stories.

[SHINY-J]

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?


Honestly, there is no “right time” that anyone could advise you to tell a woman you’re in a relationship with about your cding.

Everyone is different and every relationship is different. It all honestly depends on how strong the attraction and connection between the two of you is. I’ve dated women that would walk away if I sneezed in front of them and I’ve dated women that I could slap an 80year old nun right in front of them and they would thank me for “sharing that with them” because they felt like it made us closer... and everything in between. Obviously, I’m exaggerating, but sadly, some women weren’t too far off from those two scenarios in terms of how fickle or how desperate they were.

Truth is, only you can really answer the question as to when the time is right.

I’ve always compared it to herpes. I don’t personally have herpes, but I dated a girl once who did when she told me and explained it to me, in my mind, I immediately drew a comparison to my cding. If you tell them too soon, then you might run them off before they’ve really gotten a chance to know you... and it’s another person out there in the community that knows your secret and is pretty much guaranteed to tell others... if you wait, and tell them later, then they feel like you hid it from them and lied and it almost always ends up in a fight. And if they end the relationship, it’s still another person inThe community that knows you’re secret and they’re going to tell others too.

Between my minimal experiences telling women about my dressing and the countless stories I’ve read on here, I’m almsot of the belief that you hide it from them and then pretend that it something that you suddenly became interested in while you’re dating them... I know it’s lying, but maybe it’s a good way to find a happy medium between the two options?

If you underdress or casually leave a pair of panties out, they’ll still feel like you lied to them and they’re gonna be upset. So, one day while you’re out shopping, just tell her you’re gonna buy some panties to see what it’s like and see how she reacts.

Honestly, I’m just throwing ideas out there because there’s no tired and true way and there’s no guarantees...

I honestly believe that there are more wooly mammoths in existence than there are women who are truly turned on and attracted to a cd.
I think there are women out there who are “okay” with their man dressing, but I think the numbers are significantly low and a great deal of those women are probably “damaged” (for lack of a better word) due to previous relationships and/or experiences and are just accepting it because they are just thankful to be in a relationship. And I think the majority of those women would prefer that their men did NOT dress.

I also think it’s important for you to be honest with yourself about where you’re goig with your dressing. You may start out saying you want to underdress or just do it occasionally around the house.. but that will likely turn into dressing more and more and adding in full outfits, makeup, wigs, shaving legs, etc... which also may turn into wanting to go away for a full dressing weekend in another city or state... it may turn into wanting to go out in public fully dressed... and so on... and so on.... she may be okay with wearing panties... or occasionally dressing every month or two... but if you’re anything like me, you get an inch and you'll eventually end up wanting to go a mile...

[sometimes_miss]

Between my minimal experiences telling women about my dressing and the countless stories I’ve read on here, I’m almsot of the belief that you hide it from them and then pretend that it something that you suddenly became interested in while you’re dating them... I know it’s lying, but maybe it’s a good way to find a happy medium between the two options?
The one thing I forgot; before you go whole hog and out yourself as a CURRENTLY crossdressing crossdresser, you might consider telling her that it's something that you USED to do. During the discussion that commences, you can bring up the subject that you don't know if the urge to do so will come back someday, and what she would think about it if it does?

This allows you a way back out if she is on the fence about it, though it will also potentially ruin the relationship if she is one of those (like my wife) who was truly horrified at the concept of her mate being feminine, ever, in any way.

I honestly believe that there are more woolly mammoths in existence than there are women who are truly turned on and attracted to a cd.
No, there are a few women with fetishes out there who are into it, as well as all sorts of bisexual women who (probably due to upbringing) can't accept that they are turned on by femininity, so they get their fill of it by dressing up their guy. But in general, you're right, there are very, very few women by percentage of the population who get turned on by the idea of mtf crossdressing. Probably one in about ten million or so; we've seen those 'unicorns' show up on this forum every few years (though, we really don't know for sure; I've seen more than my share of posts that stink of being written by a crossdresser himself rather than a GG). That leaves most of us, well, out of luck.

[Karmen]

sometimes_miss and SHINY-J, great posts. Thank you for long and very educational and helpful informations you gave me. I hope I'll "win the lottery" with help of all advices I got in this thread from everyone.

[Charlotte7]

My best advice is to decide which you can absolutely live without, because in telling it could all go horribly wrong. If you can't live without dressing then I'd say take the risk and tell early. Better to lose someone you may have known for only a short time and move on, rather than (potentially) destroy a family home many years down the line. I followed my own advice 30 years ago, it worked and we're still together. Good luck.

[Karmen]

I definitely can't imagine my life without dressing. I'm not even considering that as an option.

[Genifer Teal]

Right after they say "I wish you were a crossdresser?" LOL seriously though, there never really is a good time to bring it up. That's why I always felt the best time is when you first meet or very soon after. you just need to put it out there and see how they react. Better not to start something if they're not the right person for you.

[sissythings]

I concur with Genifer... soon after you meet and before any intimacy transpires. However she reacts is the 'perfect' reaction for both you and her. If you wait, and you wind up really liking her, then it becomes much more difficult to 'spill the beans'. From my perspective, it's never wise to surrender your authenticity to anyone or any situation.

[Randi49]

I guess I look at it differently. First i am not in the closet, nor out of it. I just don't stick it in people's faces. I am pretty uncomfortable in a man's body why make others uncomfortable. If you know me well you know I want to be a woman and probably dress. You can't out me because anyone who asks I tell. Anyone I considered dating know really early there were a whole list of things they better put up with or we were going nowhere. I don't what that stuff dealt with whenwe are in love, but before hearts were committed. I have an ex who tells everyone, it is painful to her that I don't care. I told my current wife and now that I am retiring and want to dressaround the house more often she is hurt that I might be her girlfriend instead of her husband. Well that was stupid of her. Now a big part of my life will be hidden from her. Our trust will be weakened. So what good did telling her do.

[Karmen]

Update for those who are interested in my situation.

Yesterday I got a great opportunity to check her tolerance about crossdressing without actually reviling to her I like to wear female clothes. Well, mildly said, it didn't end as I was hoping. When I was at her place in the evening, she came up with the idea we should go out for a walk to the old part of town. Since it was cold outside and I was wearing only jeans from thinner material, I ask her if I can borrow her pantyhose to wear under my jeans and a scarf, so I won't be cold. I didn't make any fuss about that, just ask as it's no big deal, but she certainly didn't take it as that. She got quite upset. Her first reaction after initial shock was am I crazy? Men don't wear pantyhose and what if something happens and people would find out I'm wearing pantyhose. Than she implied I'm not a real men, if I can't cope with a bit of cold breeze and so on. I even got the feeling she would be more upset in case of accident about what others think about my clothes than me being hurt. She of course also asked me if I wore them before and I said "Yes, I wore them in the past when it was cold outside and didn't have warm pants on me.", implying to the similar situation, not telling her I do that normally. She just said "You're crazy". Soon after than we dropped this conversation and she didn't want to go out any more. Evening went on more or less normally after that. We ate dinner and watched a movie at her place, even cuddle a little before I went home. She didn't show any resentment later in the evening, just as nothing happened, but I think she was not as passionate as usually. Not sure if that was because of pantyhose or just simply because we didn't go out as she wanted in the first place.
So, I guess that's more or less indicate she is not a unicorn. Do you think I should try to bring this subject up one more time like a joke or something next time I see her? Maybe she will give some thoughts to the subject and we could have a better conversion the second time. Or should I just wait a while if she starts a conversation about men dressing in female clothes or me wearing pantyhose?

[char GG]

Karmen, maybe it’s time to stop wasting your and her time and just come out and tell her what is on your mind. Have an actual conversation about your dressing and see what happens. Not fair to either of you to play games.

[Tanya silk stocking]

unfortunately i think you know the answer and to your own question

[Bianca Fay]

Karmen, I wouldn't suggest bringing it up again. Try to be patient & see if she initiates a further conversation. At this point she has made it pretty clear that this is not something she would be comfortable with.
She is probably replaying this scenario over & over in her mind & may possibly come to her own conclusion that it's really not that bad. But she needs to process these thoughts on her own. Bringing it up again (before she's had time to weigh it out) will only aggravate the situation more & potentially lead her to wanting to talk about it with her friends in order to get their opinions.
In the meantime, this moment of quiet can allow you to decide whether or not this person is more important to you than your dressing. It's still early enough in the relationship to move on without further heartbreak or embarrassment.

[cdsamswife]

That doesnt honestly sound like a very good sign.... I wish you the best but maybe this gg .... might not be the one for u....

[kimdl93]

That is probably that. Beware of self deception. Her response seemed pretty emphatic and, maybe the best you can hope for is to clear the air, and then move on. That last part is easier said than done.

[Karmen]

Cecily, I think you're right. For now, it's probably best if I wait and do nothing. I don't want to rock the boat too much and fall in the water because of that.
I'm already sure I don't want to end up in the relationship where she knows, but don't accept my dressing habits. That would be even worse than if she doesn't know. Only relationship I'm willing to proceed is the one where she would accept my dressing habits as they are.

kimdl93
Yes, that is also an option I'm thinking about. Wait a bit and if things don't go to the right direction, let her go gently as possible and hope for the best. If she doesn't decide to do it first, since she is obviously looking for really manly man.

[gunta]

It depends on person, mine is conservative and I don't want to risk to brake our family

[Tracy Irving]

Most women are looking for men. In all my years, I have never come across a woman actively seeking a crossdresser. Personal politics has far less to do with it than you think.

[Karmen]

This story came to the end yesterday. She decided I'm not the right men for her. She didn't explain why exactly, except we don't have enough in common. She didn't started another conversation about me wearing pantyhose and I didn't either. I was still waiting for her to do it. A few days ago I also got a remark from her I like female stuff too much. She was browsing through my magazines on the living room table and saw I buy mostly female fashion magazines and I don't buy typical male magazines. Even before that, she noticed and ask why I watch Fashion TV so often, not sport channels like most men. I guess she really wants a manly man, who likes motorbikes, football and beer and don't care about fashion, especially a female part of it.

Considering everything, I think it's best we go separate ways anyway, since it was more or less obvious she would not tolerate my dressing habits. At least she done this step and I won't have to lie why I want to end the relationship which didn't lead to the right direction lately.