When to tell a woman you're a CD?

[cd_in_de]

Is it better to tell her when you first meet her? Or, is it better to wait until she has had the chance to get to know you?

[Nikki A.]

Let her get to know you first and then if there is an interest I think it is only fair to tell her. Of course if she meets you dressed then this is a moot point.

[VioletJourney]

I think you can tell her right away if you use the right words. "I like to dress up as a woman" or "I am a crossdresser" is very blunt and probably wouldn't work, but something like "That's a nice dress you're wearing. I've always had a deep appreciation for how women dress" might work.

[Rhibabes]

I think you can tell her right away if you use the right words. "I like to dress up as a woman" or "I am a crossdresser" is very blunt and probably wouldn't work, but something like "That's a nice dress you're wearing. I've always had a deep appreciation for how women dress" might work.

Ive used very similar and works like a charm BUT NEVER ON A FIRST DATE and dont try take it into the bedroom early on

[cd_in_de]

I have tried being upfront about it, and got negative responses 99% of the time. I have been considering letting a woman get to know me, then putting it as something that is harmless.

[5150 Girl]

I say tell her ASAP! Before there is to much emotional investment, in case it's a deal breaker.
It also saves trouble down the road. I kept it from my ex (largly becuse I didn't know really where I was going with this) and one day she found my "stash" and accused me of having an affair. Anyway, she was aginst this and fairly unsuportive, and it was a scorce of tension between us. (however, the main reasons she left were fiscal)
I was Sarah Palin for Holoween when I oficialy hooked up with my Polar Bear, and I actualy disclosed everything that night.
I think I'm proof that early honesty is the best policy

[Rhibabes]

I have tried being upfront about it, and got negative responses 99% of the time. I have been considering letting a woman get to know me, then putting it as something that is harmless.

sweetie ive found myself if they cant accept you as you are then 9/10 times they never will
maybe im a lil jaded but thats my 2 pennies

[cd_in_de]

An ex of mine discovered my clothes one time, assumed they were another woman's clothes, and accused me of cheating. That was why I started being upfront about it with women. But, being upfront seems to be backfiring on me.

[BRANDYJ]

I think it's a big mistake to tell a woman upfront before you both have a chance to get to know one another. I would look for signs that she is interested in me as much as I am interested in her. My being a CD is only a part of me. I want her to get to know me as a gentleman, a man and person first. I want to learn how she feels about various things. I want to learn her views on religion, alternater lifestyles, and how accepting she is of those that are "different". In spending time with her on dates or just being togethher in the early days of a potentiual relationship, you can usually tell how she will react to telling her very private and personal things such as your being a CD. Another words, I am going to be feeling her out to get an idea how she will react and what her tolerance or intolerance is.Of course I would be deeply disappointed, if in learning about her core values and tolerance, that she would not be one to accept it in her relationship with a man. But again, that initial chemistry has to be there for the both of us to pursue a relationship to begin with. But I'd have to tell her before she began to feel deeply for me. That's the hard part to gage...when to tell. If you tell her to soon, it could ruin any chance of a new romance. Wait to long and you could hurt her and yourself if she can't accept it. I am happy to say that in my past 3 serious relationships, I had judged their reacxtion correctly and the relationships continued to grow. I have never been rejected after telling someone I was seriously interested in. In fact I have done the same sizing up and getting to know some very close female friends that I'm happy to say are still friends after my telling them. Basically, it's getting to know someone well enough to pretty much figure out if they will accept it.

[Stephanie Miller]

Depends if your in fem mode when you meet them or not.
A lot easier to break it to em' then. :heehee:

[Genifer Teal]

I tell her right away. It helps explain why I am wearing a dress. :-) More importantly I need to tell her I am straight, before she assumes I am not interested. Humor aside, I know of no good time or way to tell a potential partner. It is so much easier for them to meet Genifer first.

[cd_in_de]

That is what I was thinking. I do not want a woman to judge me only on CD - which is only a part of who I am. Thank you for your advice based on your experiences.

[cd_in_de]

The only time I am comfortable being in fem mode in public is on halloween. I will tell people about it if it comes up at other times of the year, but just not comfortable going out in public in a small town.

[Jessica Jameson]

I would at least tell her before you have sex.

[cd_in_de]

That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

[docrobbysherry]

The only time I am comfortable being in fem mode in public is on halloween. I will tell people about it if it comes up at other times of the year, but just not comfortable going out in public in a small town.

Pick Rule #1, or #2 as it applies to U:

1. As a closet CD and if u r one, I would say, "Before u propose!"

2. If u go out dressed often, better tell her upfront!

I suggest U leave SEX OUT of your, "I CD", confession. Unless u only plan to have it enfem! If u both enjoy having sex, u risk losing her by confessing too soon. Wait until it STOPS being fun, THEN mention it. It mite spice things up again! Of course, that COULD BE 3 or more years down the road. If so, be sure to follow Rule 1, above!

[Lorileah]

Somewhere between "will you" and "I do"

[Stitch]

After they've gotten to know you, but before you enter a relationship is the best time. It can be hard as there is a fine line I will admit that. Too soon and it may scare her off as it's quite an intimate thing to disclose early on. Sorta how like you don't talk about exs on the first date, you keep it light and airy and just have fun. Keep the deeper stuff for later.
Too late and you've gone an created a hole multitude of problems and stress for both involved.

If you dazzle your lady friend with a lovely personality and let her get to know your many good qualities there's a chance she might stick around for the ride because of your general awesomeness. I admire CDers who tell their love interest early on as I think it takes a lot of bravery, honestly and shows that you respect the woman's choices as well. Admittedly not all women will see it the same way I do but then we all react differently to situations. This is how my partner told me and we have been together for just under 3 years now.
If you enter into a relationship without disclosing you take away her choice completely which is unfair. Some GGs are accepting, others are not but hey that fine because its their life and they should be in control of what they want in their life. They should be allowed to make the decision themselves.



That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

It can be a multitude of reasons. Maybe that's where her boundary is? Perhaps she only wants to be intimate with you as a man? Sometimes women who are dating CDers can feel like they are the accessory during sex rather than the main course so to speak. No one wants to feel second best after all.

I am accepting but I don't like it in the bedroom. Sexy time is reserved for my Man only. Ladies clothes just don't do anything for me sex wise. My partner on the other hand, wow.

[Rianna Humble]

Is it better to tell her when you first meet her? Or, is it better to wait until she has had the chance to get to know you?

I'm definitely with those who say to tell her when you feel things might go further than just a coffe or a meal once in a blue moon.


I have tried being upfront about it, and got negative responses 99% of the time. I have been considering letting a woman get to know me, then putting it as something that is harmless.

I think most people would be put off if when meeting someone for the first time they heard "Hi, I'm Jack and I cross-dress". Also please consider that when you first meet, you don't even know if you will both enjoy it to the point that you want to meet for a second time, let alone start a relationship. If you are not going to become close friends, what will telling her achieve?


An ex of mine discovered my clothes one time, assumed they were another woman's clothes, and accused me of cheating. That was why I started being upfront about it with women. But, being upfront seems to be backfiring on me.

This is the opposite extreme - you hid the cross-dressing from her while you were in a relationship. She found the "other woman's" clothes. I can guarantee that her first thought was not "I'm sure these are for him, so it's OK". As soon as that happened, the seeds of distrust were sown - if you didn't trust her about this what else do you not trust her about?

It seems to me that you have already proved for yourself that the majority of answers you will receive here are right. Don't tell her before she knows anything else about you, wait till you know whether you and she might want to get more serious. Do tell her before you start a full-blown relationship so that she sees you trus her but also so that she can choose whether this is something she can cope with.

[Diane Smith]

Most of the times I meet women are when I'm already dressed, so the cat is out of the bag from the very first moment. I kind of prefer this, since it acts as a very blunt filter against those who can't accept all the sides of my personality. It hasn't always gone well when I have had "the talk" after a few dates.

Then again, although there are many women who are friendly and curious about a CDer loose in public, there are far fewer who would actually want to date one. I'm getting pretty used to being alone.

- Diane

[Pythos]

I would think as soon as possible. I hope to meet my next potential while dressed either enfem, or when in androgynous mode. The shock will be when she sees me in "average Joe" look. LOL

[eluuzion]

hiya cd,

I believe it would be the point where it becomes obvious to you she is beginning to make a decision about making an emotional commitment to you, based upon what you have presented (represented) to her as being “yourself”. (When she is obviously proceeding under the assumption that you are not withholding any information about yourself that if revealed, might significantly impact a relationship with you.)

I believe every person should respect every person's right to make an informed decision.

I also believe that any reasonable and prudent person understands quite readily when they possess information unknown to the decision maker which might lead that person to make a decision other than the one they are likely to make without knowing that information. At a minimum, withholding any known information that may significantly influence their ability to make a rational, informed decision. I also believe that any person of average intelligence recognizes what type of information "qualifies" and when the proper time to share that information has arrived.

I believe it has everything to do with the concept of intrinsic worth, human dignity, integrity or whatever term you are most comfortable using. I call it having a "moral compass" or "character".

That is just me...

:love:

[Kate Simmons]

Any woman worth her salt will want to know what is more important to you, the CDing or her, so getting to know one another but before it becomes really serious is the best time in my opinion.:)

[Raychel]

Certainly not an authority on the matter, But I can tell you that I waited almost 15 years, and that is way too long. Although I did have good rresults in the end. It has been proven that thsi is not the best way.

[gender_blender]

Is it better to tell her when you first meet her? Or, is it better to wait until she has had the chance to get to know you?

Considering I pass remarkably well and am perceived as my desired gender without surgery (or even makeup!), I don't have to keep secrets and my relationships are better for it.

But I would advise telling them as soon as you are able to comfortably fit it into a conversation.

[Sheren Kelly]

Agree with telling before an emotional investment, but not as the opening conversation.
We are multi dimensional people, so allow the relationship to build with what you have in common, but be honest and disclose your gender expression when it draws closer than a casual friendship.

[Lucy Long Legs]

That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

Yes me too. My g/f loves dressing me up and doing my make-up and enjoys the person I become when I'm dressed. She can't bear the idea of two girls in a bed.

[JiveTurkeyOnRye]

I think it really depends on how open/out someone is about it. I dress in women's clothes in public on a quite regular basis, so for me to keep it secret very long would be strange, so I actually even go so far these days as to include it in my profile on OkCupid. Sure, it probably sends some people running for the hills, but it also ensures that someone who does respond will at least consider being ok with it.

I still don't show up for first dates wearing a skirt or dress, and I do like to talk with the girl about her comfort level before I just leap into wearing stuff with her in public, but that tends to be on a case by case basis.


That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

It's simple, she's just not turned on by you dressed as a woman, sexually, so she didn't want it in the bedroom. Most women won't be, but some people are more willing to let their partners indulge in their kinks than others. I've dated women who weren't "in" to me wearing lingerie and such, but who would be ok with letting me do it once in a while, provided I was as giving for their own needs as well, which I am gladly.

[Vickie_CDTV]

In an ideal world, one would tell her upfront from the very beginning. Sadly, this is a far from ideal world. I agree with others who say let her get to know you first (at least allow yourself to get a foot in the door), and then if you feel you are getting close then tell her. You still may face a lot of rejection, but you will have given yourself a fair shot. Remember, most GGs don't know and have probably not even met an (out) TV/TS person, and all they know about us is from terrible depictions of us in the media (Springer and similar ilk.)


That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

Sadly, this is a line that even most accepting and even participating GGs will not cross. I know how you feel, it can be very frustrating.

One idea that has not been mentioned is to try to find a GG who has dated a dresser before and has had positive exposure to us. It is a real long shot, and I assume you are a younger person (most I have known are 40s and up), but if you can find a former GG SO you may have some luck. Sometimes, and as I said it is a long shot, you can find them at events aimed the TG community, TG groups and possibly kink groups/events.

[sometimes_miss]

Stay in the closet and leave the info in your will. At least, that's my opinion based on how my life has gone so far.

[kristinacd55]

Well, how about right away!! Don't wait 31 years like I did!! :)

[TxKimberly]

What a great question! The thing is I doubt that there is a "right" answer that applies to all women. There are some very adventurous and open minded women out there that might well have a blast with it. There are also some very conservative women out there who couldn't accept this in a mate no matter how much they cared about them - it is just too far over their "this is right and this is wrong" line. Clearly you can not apply the same rules to both women.
One hard and fast rule that I would recommend though, is that a woman should be given the respect and courtesy of being informed of this before you ask her to marry you. I feel that this rule does apply to all women, regardless of their possible acceptance level.

Whether she can or can not accept this in a mate, she deserves the chance to make an informed decision, she deserves the chance to decide if she wants this to be a part of her life or not. At the age of 21, I did not have the foresight and courage to do this myself. Two weeks after we were married I just couldn't handle the secret and told her. (I mention this just so no one can accuse me of being a hypocrite.)

I have a simple definition for love - more or less it is that you care so much for someone that you would place their welfare above your own. I would not hesitate to jump in front of a bus to push my wife or children out of the way and to safety. In much the same way, if you really love a woman, you should be willing to risk the possible consequences of outing yourself to her in order to make sure that you weren't going to condemn her to a life that would make her miserable.

So - at what point in a courtship or friendship should you tell her? There are just too many variables to give a single answer, but without a doubt every woman should be told before marriage.

[sissystephanie]

My story is a rather strange one. I have been a CD for a very long time, and was married to my dear late wife for almost 50 years! She Knew that I was a CD when we married because I told her!! Because she was so much better at it, she always did my makeup and fixed my wig when I went out as Stephanie! Either by myself or with her! I was very passable then. Now that she has passed on, I still go out dressed as Stephanie but with no wig and no makeup! In other words, a guy in a skirt and feminine top!! I have met women that I met as the passable Stephanie and sometimes they recognise the clothes that I am wearing. Now these women know me as a man, and did know me as Stephanie!! But none of them ever knew that I was both people!! They have all told me that I really was a very good lady, and don't seem to be srprised that I still wear the clothing!!

To answer the major question; the time to tell depends on what your intentions are!! If this is a lady you might want to marry then tell her upfront. On the other hand, if this is a lady with whom you might like having sex but nothing more I woulodn't tell her at all! Lying about your crossdressing will not solve anything!!

[Jessica Brynn]

since I came out to friends and family, I just always tell everyone up front. Either that or I'll just start talking shoes and makeup and they eventually figure it out.

Is it necessarily a good idea to be so up front? I think it's crucial. Some people, like it or not, will judge you. These people are to be discarded. Others will not judge. These are the keepers.

I may not land many second dates with my philosophy, but it lets me sleep at night.

[cd_in_de]

since I came out to friends and family, I just always tell everyone up front. Either that or I'll just start talking shoes and makeup and they eventually figure it out.

Is it necessarily a good idea to be so up front? I think it's crucial. Some people, like it or not, will judge you. These people are to be discarded. Others will not judge. These are the keepers.

I may not land many second dates with my philosophy, but it lets me sleep at night.

That sounds like the best course of action; I like it.

[Tina B.]

There is always the tried and true (well not really true) method of waiting. If you don't tell and she likes you, If it leads to marriage, and you wait 5, 10 or more years, without her catching on, then tell her! You have have a fifty, fifty chance of things working out good, it has for some of us. But then there is the rest of the girls, that find themselves out of the marriage, and fighting to see their kids. Oh sure you can tell her before it gets serious, and just walk away if she doesn't accept it, but what kind of fun would that be, you would miss out on all of that sneaking around, and adrenaline rushes from trying to keep it all hid, and almost getting caught, I mean, read the post, people fight that risk all the time. If you tell, and they accept you for what you are, there just is not that much drama in life to keep you on your toes, but in exchange you do get to dress a lot more. Oh, and as for the ones that do accept you for what you are, but don't want to have sex with a female images, because for them that just seems too gay, and they wanted a man, not a female partner, well it helps if we accept them for who they are as well.
Relationships or like politics, they work best with compromise, so everybody gives up a little, and everybody gains something too.
Tina B.

[Doodlen]

I think most people would be put off if when meeting someone for the first time they heard "Hi, I'm Jack and I cross-dress".

I agree completely. I think it's best once they know you a bit but before the relationship part.

[BRANDYJ]

That's another issue I have experienced: I dated this woman that was okay with my CD - except during sex. What was up with that?

You ask what's up with that? It's a no brainer to me. Even women that accept their husband or SO being a CD does not make them comfortable going to bed with him dressed. They are not lesbians and want to be in bed with a man being a man! What's so hard to understand that? For some, they feel uncomfortable for fear of feeling like a lesbian or otherwise turned on by women. What's so hard to understand that? Duh! I have been intimate with 2 past wives while dressed and both were OK with it. But a steady diet of it no doubt would have put them off. My current SO could care less since she sees me as a person she loves regardless. But still, it is not something I push or ask for of her. When it has happened, it simply just happened in the moment and mood. Frankly, it's not important to me. First and fore most I want her pleased in bed. My needs come second to my desire and need to please her.