This is to tell you that you never know, that love is out there and it can absolutely happen regardless of your gender ID or what you wear. Please pardon the long post.
If you've read my occasional posts here, you'll know that my wife of 23 years and I have separated and are in the process of divorcing (NOT because of my crossdressing, and so far amicably). I moved out in May of 2018, and while I had a couple of dates, I was pretty much alone those first 14 months. I was doing quite well, enjoying living on my own for the first time since my mid-30s (with a walk-in closet! :) ), thrilled to be dressing as a woman most of the time, feeling fit and healthy and productive and surrounded by good friends. I was lonely sometimes, but I was mentally preparing myself to be alone for a long time, maybe for the rest of my life.
Then I met Elissa. On our first date I wore capris & a woman's top, my hair back in a headband, light makeup, Keds, and nail polish. We hit it off immediately and about 15 minutes into the conversation she complimented my nails. That led to me letting her know that I'm gender-fluid. Her response was "Oh! That's cool." Not much else was said about it.
We texted later that evening and both agreed we wanted to see each other again. Over the next 2 weeks (I was traveling and then she was), in texts and emails and phone conversations, she made it clear that she was comfortable dating a gender-fluid man.
For our 2nd date I thought long and hard about what I was going to wear. I finally said "Screw it, I'm going to let her see who I really am." I wore a khaki skirt, a white woman's pullover, padded bra, makeup and nail polish, and my hair curled and back in a headband. We ended up closing down the bar and then making out in my car. At one point the waitress came over and said "Can I get you ladies anything else?"
I asked Elissa how that made her feel and she said "That doesn't bother me in the least."
We?ve been seeing each other now for about 4 months. It's wonderful. She has 3 children including 9-year-old twins, so we don?t get to see each other as much as we?d like, but we've spent a few weekends together and we sleep over at each other's place when we can. We're traveling together the next 2 weekends. I've been out with her wearing dresses, skirts, and men's pants and shirts. I usually wear makeup & nail polish regardless of whether I'm wearing men?s clothes or not. And of course I have a very cute & girly blonde bob.
We've talked a lot about what it means to me to be gender-fluid and how it might affect her and her kids. At one point early on I expressed doubt about whether she would really want to be with this older (she's 10 years younger than me), crossdressing, writer dude, and she replied "Listen. I'm in this for you. The all of you. The entire person."
She has boundaries: she prefers no lingerie in the bedroom (it's interesting that, now that I crossdress regularly in public, my desire to have sex in panties and bras has diminished). She thinks some of my tastes in woman's clothing are not, uhh, super-modern (She teased me that my outfit on our 2nd date was like "My mom going to church"). And she tells me when she'd prefer I go out in "boy mode" -- for instance when we're with her work colleagues (even though she's told more than one of them that I'm gender-fluid). I try to respect her boundaries and I'm so grateful to & crazy about her that it's not hard to do so.
I had assumed that, by going fully public with my crossdressing, I was making the choice to express my gender ID rather than be with an attractive, smart, successful woman. That has proved not so. I am incredibly fortunate to have met her.
I know that many crossdressers will never meet someone like Elissa. I'm here to tell you, though, don't give up. And be forthright, on the first date, about who you are.
Thanks for reading -- TT
