This is to encourage those of you who believe it’s impossible to meet a woman who enjoys, or at least tolerates, your cross-dressing. It’s not.
As I’ve mentioned here, my wife and I separated back in May (not because of my CDing). I’ve begun to test the waters of online dating, and I met a woman recently on OK Cupid – I’ll call her “Laurie.” Her profile was interesting and her photos attractive. Also, she listed her sexual preference as “Bisexual,” and in the “What I’m looking for” section she listed some of the usual qualities and then said “and, above all, open-mindedness.”
Okay, I thought, let’s see how open-minded she is.
We had drinks at a local bar (she actually lives about an hour from me). I didn’t want to wear a skirt or dress, but I wasn’t going to hide my gender fluidity, either. I wore jeans and a unisex pullover. My hair (which is in a bob just off my shoulders) was back in a headband and I had light makeup on. Also, my nails were done a cinnamon color (I considered taking it off but I thought “Ahh screw it”). Before we met I spent a fair amount of time thinking about how to bring up my crossdressing. As it turned out I didn’t have to.
We sat down and started talking easily. After several minutes I complemented her on her nails. (They were done a sparkly purple, a color I would never wear, but there you are.)
“Yours look nice too," said Laurie. "Do you always wear polish?”
“A lot of the time.”
“Do you crossdress?”
I laughed. I’d been trying to figure out how to tell her, and she clocked me in under 10 minutes.
“Yes I do.”
“Fabulous!”
I will pass over the details, but it turns out she is into, uhh, alternative lifestyles and she has no problem dating a crossdresser. I ended up showing her some photos of me en femme on my phone.
“Would you date this person?” I asked as she looked at them.
“Absolutely!”
We are going to the theater in 2 weeks and I’ll be wearing my black j.jill pencil skirt, a lovely rose-purple widenecked top, and black hose. (I’m looking for a pair of low-heeled pumps.) I’ve scheduled an appointment with my wonderful hairdresser to do my hair and makeup that afternoon. And, naturally, my nails will be done.
I don’t think this is going to turn into some great romance – her personal life is way more complicated than mine – but she’s someone I definitely look forward to hanging out with. As girlfriends.
Don't give up. Open-minded women are out there. And upfront open honesty is always best.
Originally Posted by TracyT
Now that I'm old enough (maybe even approaching too old now), there's no such newspaper. Thank goodness for the Internet! 
