I arranged an extended dinner date with Caitlyn after a little email and phone discussionc.
I picked her up in San Francisco and we drove down to a trendy Raw Bar / Seafood Restaurant in the Marina. Caitlyn was wearing stockings, a skirt and a sexy backless top, and heels that put her just a little taller than me. Our reservation wasn't for about 20 minutes, so we strolled down to the Marina Green, talking about art, architecture, and life in general (and getting quite a few jealous/appreciative/second looks from passers-by). We had a pleasant dinner (ordered a bunch of appertizers and shared them, just like with a GF) and then drove back to her place. About the only non-GFE thing about dinner was I've never before had dinner with a woman who'd be looking on the other female diners and musing how nice it would be to have that one join us!
Once we got back to her place she told me to hold on a minute, and disappeared into the bedroom. When I had permission to enter, I found the room lit only by the light of many red candles, a fantasyland of red, gold and flickering light.