Question for my GF

[LelaK]

I'm over 60. I've been writing to a woman online since Jan 2 after she asked me a question the day before on a dating site. She says very little, but she calls me dear, love and darling. She started off by saying I have nice lips. So I said I'd be glad to have her kiss them. I guess that's why she talks rather affectionately. But right off she said she won't plan anything till the end of the month. She has only told me her occupation and the number of kids and grandkids she has. I told her more about me than she has told me about her. But I haven't mentioned CDing.

Today I plan to ask her how she feels about crossdressing.

[JeanTG]

Good luck, let us know how it turns out. I think it's best to reveal this information up front. I did with my wife when we married many years ago. It hasn't always been a smooth ride. Now it's accepted albeit DADT. I dress as often as I can which can be anything from 1 to 4 times per week. If she is accepting, I hope she can be a good sport about it as well!

[Micki_Finn]

Don't know how familiar you are with online dating, but have you confirmed that she's... you know... real? You might want to make sure she is who she says she is before you go revealing too much about yourself. She's already put you off once. While it's good to be honest and upfront, that's the sort of info I think that can wait until things start looking serious.

[Shelly Preston]

I would suggest you have some kind of video call before making any comment.

If you cant or wont do that, at least wait until you have met.

[AllieSF]

I also believe that telling sooner rather than later is the best way to go, when you can. Now the sooner part really depends on each situation. My opinion is to only tell when you think that a strong relationship may be in he future. So, tell before anyone makes that emotional commitment, which seems fair to both parties. That way, you can find out more about her, including how open she is for this side of life. As others have already said, if you tell too soon and she reacts badly, she can definitely make your life difficult if she is mean enough to do so. So, find out if you are that interested in her, then if you can trust her, and then what would you do in a worst case scenario where she goes ballistic and tries to out you to everyone that she can. Good luck.

[LelaK]

I got her reply. She said "whatever floats your boat". And that seems like great news. She has already seemed to be rather tolerant in other ways, so I felt hopeful and now I'm much more so.

So far, though, I haven't admitted that I do crossdress. I worded my initial question in a way that could lead to a favorable result regardless of her answer. Had she said she doesn't like crossdressing, I was planning to ask if she then prefers that women wear dresses instead of pants or jeans, because I'd like more to see her in dresses than me in them.

She doesn't know my surname or my phone # so far, so there wasn't much chance of her outing me to anyone.

[Ozark]

"Whatever floats your boat" sounds to me like a troll response.....

[SharonDenise]

I am widowed am have begun to date again off the internet. Of the three ladies that I dated long enough (more than three dates) to tell them that I cross dress, two of them were fine with it. They had relatives that cross dressed or were transsexual. The third dropped me like a hot potato when I revealed that fact to her. I also came out to my wife's best friend (female). She was supportive at first, then turned against it. She told me to be a man and didn't want any further interaction with me. I feel bad because it was my wife's close friend.