Well, this last weekend I had a wonderful new experience. For the first time in the two years or so that I have been dressing and going out as Ceera, I asked someone out on a real dinner date! This was also the first time I went out on any kind of 'date' with anyone other than my late wife in the last 34 years! My wife died in Jan 2014, and while during the last two years I have socialized as Ceera at bars and nightclubs and other activities many times, and I even brought someone home one time for some intimate play after meeting them in a nightclub, I have avoided seeking a romantic pairing or actually dating. Well, that egg's now been cracked and scrambled!
On the 11th, I attended a "speed dating' event as Ceera for the first time ever (I had never tried speed dating in either gender presentation). It was a 'ladies' only' event hosted by an LGBTQ Ladies Happy Hour group that I have started socializing with. The largely lesbian group does include a few MtF transgender or gender fluid girls like me, and the event coordinators assured me I would be welcome, even if most of the lesbian ladies would only want to be friends with a transgender girl, and not date one. I'd hesitated to join, but with that assurance I signed up, on the weekend before the event. Valentines' Day was the following Saturday, and in hopes of something clicking I also made a dinner reservation at a very nice restaurant in town. Unfortunately, I was late enough in making that reservation that the best I could get was a 10 PM reservation time.
About 14 ladies participated in the speed dating, held at a bar downtown, including one other MtF transgender girl and one gender-fliud GG who prefers presenting or at least dressing as a male. As fate would have it, I never did end up across the table from the other MtF transgender girl, but I wasn't that interested in her anyway. The gender fluid GG was a girl I had been chatting with at other events, and I knew we had several things in common. We were already starting to become friends before the event. But she's also young enough to be my daughter, so I didn't yet know if I stood any chance of dating her. She's in her 20's, while I'm in my 50's (but I look more like I'm in my late 30's to mid 40's while en-femme). Surprisingly, both she and another primarily lesbian GG (who is also in her 20's or a bit older) indicated they would be willing to go on a date with me as Ceera, despite our age differences. The second girl even admitted that one of her first lovers had been a woman who was 30 years older than she was.
At a dance at a different club after the speed dating event, the gender fluid GG that particularly intrigued me wasn't there, but I tried asking the second girl who has shown some interest in me out for dinner on Valentines' Day. Unfortunately, she already had plans for that weekend. I may still ask her out some other time, but for now I decided to try the gender fluid GG, who I knew I had interests in common with. I messaged her the next day, and she accepted my invitation. Over the course of several back and forth messages we agreed the 10 PM time I had a reservation for was rather late for both of us, and that there was no particular reason not to reschedule for the next Saturday, and get a better time. We also both agreed that neither of us were looking to leap into a 'relationship', and that this date would serve to get to know each other better as friends. 'Romance' might happen eventually, but friendship was an important prerequisite for that for both of us.
She lives within walking distance of the restaurant and other clubs in the downtown area, so we met at 6 PM at another happy hour event hosted by the LGBTQ Ladies group, had a drink there with our friends, and then walked to the restaurant, 5 blocks away. One thing that was humorous was that they carded both of us when we ordered wine at the start of our meal. She looks young enough that asking her for ID isn't all that unusual, but I was amused that the waiter asked to see my ID as well. To his credit, he didn't have any problem with me handing him my male driver's license.
The conversation and the meal were both wonderful. I think we got to know each other a lot better, and we felt really comfortable being out together, with me all dolled up and feminine, and her dressed in a dapper male outfit. We will definitely be doing more things together soon, such as trips to the beach when the weather gets warmer. After dinner we walked back through downtown, and parted company at a local nightclub, with her going home and me stopping for another drink and some more social time. We parted on the sidewalk outside the club with a hug, and not a kiss, but that was fine with me. Quite happy to take it slow, and see where this might go.
crossdressing...theirs an app for that 
