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Thread: How to tell people that you are a cross dresser

  1. #1
    Andrew in drag FelicityMay's Avatar
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    How to tell people that you are a cross dresser

    I know I havn't been here that long, and am not the most experienced person around, but I have found many ways that can feel safe when telling someone about your little secret!

    Be careful who you do tell, make sure you are pretty sure they will be okay with it before you do, but here are some ways I have found.

    To a Friend/Sibling:

    Depending on the type of friend, this can be a confusing one to figure out. I am just going to assume it is someone you talk to quite a bit and know personally.
    You can start by transitioning some conversation towards talking about deep personal stuff. make sure you are in the right mood for it, it can make all the difference.
    I have tried this two ways, both seem to work alright.
    1. "If you tell me your deepest secret, and I think it is strange enough, I might think about telling you mine". This can get them excited to know something about you, and you may even get to know them better too.
    2. This is one I do more often, because I've just kinda turned into this type of person. When talking with someone you generally joke around with a lot, and like to have fun, come out by saying something like "I have done so many crazy things before, and I am starting to lose all my shame, because I just enjoy life too much. Wanna know something weird? I like to cross dress and I don't even care who knows it!" you can add more about being proud, and not caring if people mock you or laugh at you, but that is the just of it.

    To your parents

    This one, I can't say I did so well here. Because my parents found out by my close friend ratting me out. Here is how I should have taken care of it.
    Get really personal with your mom or dad, just one on one. Talk about how you are feeling down, because there is something about you that you feel you cant talk about to anyone. Being your parents, they generally should love you unconditionally, and will want to know. Tell them that there is something built up inside of you that has haunted you, and you want to let it out somewhere that you feel you wont be made fun of for. Tell them about how you like to cross dress, and tell them how it makes you feel. They will likely be understanding when you come to them very softly, and are admitting a deep secret.

    To a girlfriend:

    This one is a little risky, and you may want to be prepared to lose someone close to you. This may be better in the long run, so you don't end up getting too attached to someone who is not going to be accepting of it. Now this person will likely be someone you are very intimate with, and like to share lots of deep things together. The one key thing about sharing deep secrets, is that you want to come off as being weak. If you really humble yourself, the person you are telling will usually have sympathy, and feel your pain. This is something that may be a big part of your life, but you have to hide it from everyone, so it can really damage you emotionally! If you show your soft side, and show that you are willing to open up to her, it can help you feel much better about everything.

    To a wife:

    (Yea I know I'm 18, but this is how I would do it if I were married )
    This one can be the most difficult of all, so be very careful.
    Maybe start by going a couple weeks, gradually starting to act generally more feminine, then approach her with,
    "I don't know if you have noticed in the past, but I have a pretty strong feminine side to myself. Now this might seem a little strange, but to tell you the truth, it goes deeper than it looks. I like to cross dress! It is something that has always been a part of me, but have been too shy to show it.It is not just a phase, and I will always have this kind of desire, but if it bothers you enough, I will stop doing it, just for you."
    The most important part is that you show her that you care for her more than yourself, which should at least strengthen your relationship.
    If it turns out she really doesn't like that you do it, and does ask you to stop, maybe go cold turkey for a while. Then after a few weeks/months, tell her that you are starting to feel down, because you don't feel like you can express yourself the way you want. No one can be mad at you for how you feel, so she may even be understanding, and make exceptions.

    The common theme here for the tl;dr, would be
    -People can't be mad at you for your feelings
    -Be proud of yourself
    -Not everyone can be good to tell
    -Let people know that you are still the person they have always known and loved
    -Make sure you get in the right mood to how you are going to tell them, and try to transition the conversation in that direction
    -Those who matter don't mind, and those who mind don't matter

    I hope that at least someone got something out of this, and hope that being 18 doesn't lower my credibility, haha. I have noticed a large amount of threads about people wondering how to come out and tell loved ones. So I wish you all good luck, I know how hard it can be.

    I have come a long way in the past month. I have told a few close friends and family. unfortunately, the 'secret' has spread like wildfire and most the people I know, knows about this. I am preparing to publicly announce soon on Facebook, so that at least I can clear it up and have them hear it from me.

    I am happy with myself, and although most of my friends don't necessarily approve of it, I don't let them lose their respect for me, and I still show that I love all of them!

    -Felicity

  2. #2
    Member Barbara Maria's Avatar
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    I've tested the water by telling 3 people,my dad,my brother and a close friend nothing about dressing,only that my feminine side has been coming out lately,just to see what they'd say.All three said exactly the same thing,"Oh,oh!"I guess they don't need to know any more.

  3. #3
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    Felicity, a nice thought out thread.
    Written clearly for all to understand.
    I hope a lot of people read this along with other ways of coming out to those close to them.
    I get annoyed at older people that can't understand that a young person like yourself can have an alternative insight into what they have not experienced.
    You being 18 and not married.
    Not speaking from experience, but as an outsider can be a refreshing alternative.
    It is akin to a CD'er advising transsexuals on some things.

  4. #4
    Member boink's Avatar
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    Congratulations on taking the steps to be more out, that's a big deal.

    I think you have some good thoughts on how to come out, and it's great to take pride in being yourself. It was really rewarding for me to come out to my partner/friends/family and has helped me to feel more "real." It's still a process for me, and I haven't come out to absolutely everyone (there are still some friends I've not had the conversation with, and a few select older family members who my wife and I agreed we would likely not disclose this to), but I've yet to have a bad experience and each person who knows is another person there to support/accept me for who I am.

    General advice: I prefer to come out either in person, or preface a conversation in person with a call/email and then have a face to face talk about it. I think it's more personal, and shows your trust/respect for the other person. If I am going to come out to someone I'm direct about it "I have something very important to tell you about me" and then I go from there. I make sure there is time and privacy for questions, and I am always happy to give someone a little space/time to think about it.

    I will also say that some of the reactions are dependent on context. I'm younger (27, started coming out at 19 to my now wife) and have a generally liberal group of friends/family which helps. I imagine others are not so lucky.

    For most relationships I think you have a lot of leeway in terms of coming out. I came out to my parents fairly early on because I knew it was important for our relationship, but other than parents/siblings most other friends and family members can be dealt with on a pretty flexible time schedule based on your comfort and interests. When it comes to wives/girlfriends/partners/spouses I am a strong believer in telling someone as directly and early as possible in a relationship (okay, maybe not a first/second date topic, but once anything gets serious). The longer you keep something like this from a potential partner, the more hurt/betrayed they may eventually feel.

    Now I will say that from my experience this seems like maybe not the best approach for a wife/girlfriend:
    Quote Originally Posted by FelicityMay View Post
    Maybe start by going a couple weeks, gradually starting to act generally more feminine, then approach her with,
    "I don't know if you have noticed in the past, but I have a pretty strong feminine side to myself. Now this might seem a little strange, but to tell you the truth, it goes deeper than it looks. I like to cross dress! It is something that has always been a part of me, but have been too shy to show it.It is not just a phase, and I will always have this kind of desire, but if it bothers you enough, I will stop doing it, just for you."
    Trying to sort of not-so-subtly reveal your feminine side is probably going to raise some red flags and questions in a partner's mind that are probably not a great thing to do, and I would strongly recommend not saying "I will stop doing it, just for you." I've yet to see too many crossdressers "stop" what they're doing entirely. Ultimately you should just lay out who you are and what your needs are to your wife/girlfriend/partner and be reasonable about your expectations. I think the key is giving them some space to ask questions, think about what they need, etc. and then be willing to negotiate how to move forward. For my partner it took a full 2 years to go from coming out to her being comfortable really spending time around me like that, but I am glad I came out then, and I'm glad I was patient with her as we worked through it.

  5. #5
    The best of both worlds Kathi Lake's Avatar
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    Boink is on point. Yes, you can stop for awhile (172 days and counting), but at what cost? Are you being true to yourself? Will she think that it's gone away? What happens when it comes back (and by and large, it does come back)?

    I like much of what you said. Although some of it is the tiniest bit manipulative ("setting the stage" for the parents by playing on their emotions), as long as you speak truth, you are halfway there. And, since you're dealing with other people, is as far as you're ever going to get - your half.

    Kathi

  6. #6
    Silver Member NicoleScott's Avatar
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    Quote Originally Posted by FelicityMay View Post
    It is not just a phase, and I will always have this kind of desire, but if it bothers you enough, I will stop doing it, just for you."
    You shouldn't make promises you can't keep.

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    Telling someone else, or yourself, that you'll quit is an outstanding way to completely wreck your life. Don't do this.

    Wanna know the real secret to telling your wife?

    Tell her before she's your wife. If she breaks up with you over this, hard as that may be, you are liable to be better off.

    There are people who quit CD, but the odds are against it.

  8. #8
    Andrew in drag FelicityMay's Avatar
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    I agree to not quit permanently, but at least cut back, to show her that it can hurt you to hide it away. she will want the happier version of you back, and might be inclined to allow it.

    I honestly will never even put myself in this position, because I will want to marry someone who already knew that about me. after marriage is a pretty bad time to start confessing big things about yourself.

    sometimes, your wife will just flat out hate it, and never want you to do it. in that case, it wouldn't really matter how you told her, and it may be very hard to get along after that.

  9. #9
    Andrew in drag FelicityMay's Avatar
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    I'm not forming the official guide here by the way. any other additions are welcome. just sharing ideas

  10. #10
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    Quote Originally Posted by FelicityMay View Post
    sometimes, your wife will just flat out hate it, and never want you to do it. in that case, it wouldn't really matter how you told her, and it may be very hard to get along after that.
    Yeah, read my thread called "out". That's where I'm at. We'll see if it gets better.

    By the way, in case you are wondering, being eloquent makes no difference. My speech was beautiful, or so I'm told, and two of the people I rehearsed it on cried.

  11. #11
    Jennifer(not just)at home Jenniferathome's Avatar
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    Quote Originally Posted by FelicityMay View Post
    To a wife:
    Maybe start by going a couple weeks, gradually starting to act generally more feminine, then approach her with,
    Felicity, your youth comes across loud and clear. While your message is well intended, unfortunately, a summary of your advice is "tell someone you know will be ok to tell." That falls into the "duh" category.

    Now, specifically, the advice on telling a wife (or in fact anyone) is way off the mark. Cross dressing is NOT something one can hint their way in to. The simple reason is that the woman hearing/seeing these "hints" will not reasonably connect the dots to cross dressing because cross dressing so so far off the radar for most women. They have no cross dressing reference as we do. Someone trying to hint their way is more likely to cause their spouse to think there is an affair going on.

    No, the ONLY solution to telling a spouse or SO is a calm sit-down, face to face honest conversation. And it always starts with, "I need to tell you something about me...."

  12. #12
    Way too girly Tracii G's Avatar
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    Felicity I think you make some good points and its a very well written thoughtful thread.
    Thanks for posting it.
    You're never going to change me
    You're never going to break me

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    I don't really know what really say about just comming out and telling them. I would rather have them bring up the subject to me and just confirm it. I have done this over a period of time by gradually adding more slightly fem items to my wardrobe, no make-up wigs or jewelry, just clothing. After that just wait and see if they notice the difference and comment. Never really been a problem but like your thoughts also. To me its eaiser as far as how much to explain.

  14. #14
    Andrew in drag FelicityMay's Avatar
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    Like i said, the wife one is the most complicated.
    there are probly hundreds of ways of doing this, but you have to figure out what type of person you both are. I would do it this way if I somehow got into the position, but I also have a very strange side, and don't mind looking silly most of the time.
    I do like to hear more options from the rest of you though!

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