Part 1:
Hi everyone,
I had the adventure of a lifetime! I've dressed and gone out many times for a single day/night, but that's it. I always wanted to dress up and stay dressed for several days in a row. From last Saturday night until Tuesday morning, I finally had the chance. My (supportive!) wife is traveling this week and she encouraged me to grab the chance that she knew I wanted. So I did! @Teresa.smith.va also gave me good advice and encouragement.
I went to Boston, which I know pretty well and always felt comfy/safe there.
I arrived Saturday night in drab mode, because of circumstances. I wanted to go to Club Cafe (a popular LGBT nightclub), so I changed into shiny black pants, a blue/green sequined top, and black boots. The top is nicer than the picture indicates -- it's not so patchy in real life. On my way outside, I took the drab clothes from traveling and put them in my car, on the theory that if I wimped out from dressing one day and wanted to go drab again, I'd still have to dress up to go outside and get those drab clothes, in which case I'd be en femme anyhow so might as well stay that way! LOL it worked. I spent a few hours at the club, got invited by some cis women to dance in their group, and maybe got a little bit tipsy.
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Part 2:
Sunday, I slept pretty late. I woke up and put on a cool pair of space-themed black leggings, a black sweater, and a light blue jacket. I went out in black Keds, but they were hurting my feet (lots of brick sidewalks), so I changed back into the boots for the evening. I started the day by getting my first ever professional manicure! I spent most of the afternoon checking out an annual spring fair ("Mayfair"), and then tried -- and failed -- to find some interesting nightlife. I wound up at Jacques which is a famous dive/CD bar, but I was the only regular customer there -- everyone else was there for an amateur standup comedy night. They weren't very funny.
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I like seeing how I like from the back. (I always wear hip/butt pads when I dress, which helps sooooo much to create the illusion of a good figure!)
It looks like maybe I didn't (ahem) tuck well enough on Sunday. Oh well. Nobody gave me any indication that they noticed!