Page 2 of 3 FirstFirst 123 LastLast
Results 26 to 50 of 65

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

  1. #26
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    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.

  2. #27
    Aspiring Artist Kelly DeWinter's Avatar
    Join Date
    Jul 2008
    Location
    Wherever there is a Sale or Macys, but mostly Baltimore MD
    Posts
    3,368
    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
    Kelly DeWinter
    Find Kelly at:
    Kelly's Blog
    Flicker
    [COLOR=#2e8b57

  3. #28
    Member Shayla's Avatar
    Join Date
    Nov 2017
    Location
    Nor Cal
    Posts
    137
    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!

  4. #29
    Platinum Member
    Join Date
    Jan 2010
    Location
    A bit south of the 49th!
    Posts
    23,676
    I’m thinking probably sooner, rather than later.
    Remember always that you not only have the right to be an individual, you have an obligation to be one.

    Eleanor Roosevelt

  5. #30
    Silver Member Aunt Kelly's Avatar
    Join Date
    Nov 2016
    Location
    Greater Houston
    Posts
    3,041
    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

  6. #31
    Member
    Join Date
    Apr 2008
    Posts
    219
    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...

  7. #32
    Rachel Rachelakld's Avatar
    Join Date
    Jan 2013
    Location
    New Zealand
    Posts
    4,450
    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.
    See all my photos, read many stories of my outings and my early days at
    http://rachelsauckland.blogspot.co.nz

  8. #33
    Silver Member
    Join Date
    Oct 2006
    Location
    Central NY
    Posts
    3,655
    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.

  9. #34
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    Location
    Northeast Pa near NJ and NY
    Posts
    10,444
    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.
    I don't wear women's clothes, I wear MY clothes !

  10. #35
    Senior Member
    Join Date
    Feb 2012
    Location
    The South
    Posts
    1,679
    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.

  11. #36
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    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.

  12. #37
    Aspiring Member jacques's Avatar
    Join Date
    Sep 2008
    Location
    East Yorkshire UK
    Posts
    922
    my advice - never lie about it.
    Always speak the truth, but you should not always speak!

  13. #38
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    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.

  14. #39
    Aspiring Member Steph_CD_62's Avatar
    Join Date
    Sep 2013
    Location
    Nebraska USA
    Posts
    597
    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.

  15. #40
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    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.
    Last edited by Karmen; 01-13-2018 at 05:32 PM.

  16. #41
    Silver Member Amy Lynn3's Avatar
    Join Date
    Aug 2007
    Location
    North Carolina
    Posts
    2,161
    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.

  17. #42
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    That's a great idea. Thanks!

  18. #43
    Aspiring Member Joni T's Avatar
    Join Date
    Nov 2007
    Location
    The OC
    Posts
    746
    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

  19. #44
    AKA Lexi sometimes_miss's Avatar
    Join Date
    Nov 2008
    Location
    The state of flux, U.S.A.
    Posts
    7,212
    Quote Originally Posted by Karmen View Post
    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.
    Quote Originally Posted by Tracy Irving View Post
    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.

    Quote Originally Posted by Karmen View Post
    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.

    Quote Originally Posted by Lydianne View Post
    And if you do it later and things don't go as planned, then you risk her exposing you to the world
    &
    Quote Originally Posted by Glenda58 View Post
    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.
    Quote Originally Posted by jacques View Post
    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.
    Quote Originally Posted by Karmen View Post
    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.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  20. #45
    Platinum Member Beverley Sims's Avatar
    Join Date
    Nov 2011
    Location
    Lowestoft UK. Beverley was here.
    Posts
    30,955
    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.
    Work on your elegance,
    and beauty will follow.

  21. #46
    Junior Member MLane's Avatar
    Join Date
    Jan 2018
    Location
    USA
    Posts
    53
    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.

  22. #47
    Junior Member Wallaone's Avatar
    Join Date
    Sep 2011
    Posts
    40
    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.

  23. #48
    Member SHINY-J's Avatar
    Join Date
    Jan 2011
    Location
    Colorado
    Posts
    135
    Quote Originally Posted by Karmen View Post
    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...

  24. #49
    AKA Lexi sometimes_miss's Avatar
    Join Date
    Nov 2008
    Location
    The state of flux, U.S.A.
    Posts
    7,212
    Quote Originally Posted by SHINY-J View Post
    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.
    Last edited by sometimes_miss; 01-16-2018 at 08:46 AM.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  25. #50
    Aspiring Member Karmen's Avatar
    Join Date
    Dec 2006
    Location
    Europe, Slovenia
    Posts
    647
    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.

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  


Check out these other hot web properties:
Catholic Personals | Jewish Personals | Millionaire Personals | Unsigned Artists | Crossdressing Relationship
BBW Personals | Latino Personals | Black Personals | Crossdresser Chat | Crossdressing QA
Biker Personals | CD Relationship | Crossdressing Dating | FTM Relationship | Dating | TG Relationship


The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs.
We are always trying to improve the forum to better serve the crossdresser in all of us.

Browse Crossdressers By State