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.
I definitely can't imagine my life without dressing. I'm not even considering that as an option.
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.
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.
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.
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?
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.
unfortunately i think you know the answer and to your own question
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.
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....
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.
Remember always that you not only have the right to be an individual, you have an obligation to be one.
Eleanor Roosevelt
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.
It depends on person, mine is conservative and I don't want to risk to brake our family
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.
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.
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