When to tell a gg?

[LunaDarling]

So i have a few gg's that im seeing, a few of them know about my dressing. many do not. how long would you wait to tell a gg youve been seeing about your dressing? should i wait till i know they like me, then tell them? or just let them know right away so they dont get all conflicted after they get to know me... am i overthinking this?

[Launa]

You're not over thinking a single thing!
If I am you I would tell her the second it looks like things are going to get serious! Thats what I did and I'm damn glad I did it way back when.
My only regret is at the time I was only into wearing dresses around the house and thought that was just great and I didn't need anything else. But this CDing with me has escalated over the past 2 years into complete transformations of myself and going out into the public light. This has had its ups and downs with my SO, she has said on a couple of occasions that there is a big difference when you want to venture out into public vs hanging around the house in a dress and some lingerie. So keep that in mind when you're answering questions cause you never know if you change your mind and want to go dressing outside the house.

[putter288]

i told my S O on our third date as I did not want to hide anything...that was ten years ago and her and I still live together .
do not hide it , if you are serious about her ... if you do it will plant that lie and mistrust issue.

[MsRenee]

I think the sooner the better that way she cant be mad at you for hiding it. If its meant to be she will be okay with it and will make it a part of toyr luves together.
Renee

[UNDERDRESSER]

I am also of the camp that says tell when you think it's getting serious. I was chasing my GF for about 6 weeks before I told her. I had declared myinterest in her right from the start, but she needed time to get her head straight from previous relationships, and kept me at arms length for a while. We got to the point that our discusions were getting pretty intimate, ( if not our physical relationship ) and her reaction was better than hoped for "Oh, cool!"

I told her that I thought honesty was going to be important between us, then just blurted it out. I am pretty certain that the trust I showed in her by telling her was a definite point in her letting me closer.

Your GF's reaction may be different of course, you may want to consider what damge she can do you if the reaction is violently negative. In my case, even if it put an end to my hopes for a romatic relationship, I was pretty certain I could rely on her to keep it private.

[RADER]

I mention to my now Wife on the second date that I liked the dress I saw on TV
while waiting for her at her house. Later that night she asked me what I meant
about liking the dress. I said I wish I could fit into a dress like that. I knew I would
never as the dress was on a size 2, and I wear, well a lot bigger size.
About 3 weeks later, at a BBQ at my house, it started to rain, we went inside,
and she asked me if I had any dresses. Well I just have a few skirts and tops.
Go and show me, well I did, she liked it, and we got Married a few months later.
It is almost 19 years, And I love her a whole bunch.
So If you are serious, tell them in a nice way. You will find out soon if they are
scared or not real soon. Good Luck.
Rader

[Miriam-J]

There's always a time in the forming of a relationship where you feel comfortable enough together that each of you shares the deep, dark secrets known to no others. Depending on the pace of the courtship, this could be after a month or after six months (or later). When that time arrives, your crossdressing is one of the most important to emerge. If that time never arrives, then you really shouldn't make any long term plans anyway.

By the time you get to this point in time you'll have a good feel for your GG's attitudes about a lot of related subjects and her openness to variations like crossdressing. If signs are positive, all will go well. If signs are negative, you'll probably need to look elsewhere.

Miriam

[Samantha43]

My wife met Sami after three or four months of dating. She took it well and we have been married for 25 years.

[Beverley Sims]

If you have the figure to carry it off presentation to a girl is so much easier, I had done drag shows before and it was already out there when I told my wife.
She was aprehensive for a long time but I don't drink or smoke and she thought X dressing the lesser of all the evils.
I do not believe in dry weddings and I supply ashtrays. :)

[Vickie_CDTV]

When the relationship becomes serious and before both of you begin a serious emotional investment in each other.

At the very latest, before marriage, and especially before having children.

[kristinacd55]

Once you decide that things seem to be getting more serious with one of them, that's the time to broach the subject.

[Matia]

from my experience, i prefer to say it to girls sooner than later, before anything deeper is happening, when you can explain yourself, they don't really mind, i don't remember when i had any negative response at all, later if the girl likes you, she knows about you and she is not falling for someone fake, that's how i got together with Salma and we're doing great.

[kimdl93]

That is really a matter of how well you feel you know the other person. You need to make several judgements. First, is it important for the person to know...is it a casual relationship, a strong friendship or something more intimate? Second, how well do you know this person in terms of their overall attitudes towards diversity and gender variation? Third, could telling the person have adverse consequences in other aspects of your life, such as employment?

[BRANDYJ]

I am just now coming out of a 6 year relationship where she knew before we even met. So I have not had to deal with when to tell for over 25 years since my last wife.
So here's what I think is best... I think that once I feel she will be the open minded type with non-judgmental attitudes toward anything gender related such as her feelings toward gays and lesbians. Next, when I feel we have spent enough time together that she has a good idea of what my character, sense of self respect, and honesty is. When I sense there is a possibility of this new person becoming serious about me and or my becoming serious about her. It needs to be brought up before either she or I can be hurt or disappointed because she can not or will not be able to accept it for whatever reason she may have. I don't want to face rejection from a woman because she can't handle it. And I don't want to hurt a woman by not telling her until her feelings toward me lean toward falling in love.

I sure don't want to wait until we decide to sleep together and she has to ask me why my body and legs are shaved. That could be very awkward.

[Angela Campbell]

I sure don't want to wait until we decide to sleep together and she has to ask me why my body and legs are shaved. That could be very awkward.

Or when I undress and she sees my pink panties....

[Stephanie47]

It seems everyone suggests the earlier the better. I'd use caution. Once the Genie is out of the bottle, she cannot get back in. If one is 'out' to a lot of people the consequence of disclosure are totally different than one who is totally in the closet. I've seen too many threads, and one real life disclosure, where the self 'outing' has disastrous results. I think the subject can be approached without disclosure. How does she react to the politics of gays and lesbians? Of transgendered issues? Reaction to watching Tootsie or Mrs. Doubtfire? If she wretches and pukes at that, then I'd not pursue the relationship at all.