My wife is traveling for a week in May, so she suggested that it's a great time for me to also do some solo travel and finally fulfill my dream of being Sherry for more than just one day.
I decided to go to Boston. I went to college there and feel very comfortable in/around the city. I know my way around, what are the safe areas, etc.
So ... Sherry is taking a vacation!! I''m so excited. I've been out dressed many times, but never for longer than just one day/night. The biiiiiiiiiiig question is, do I also take a set of male clothes, just in case? The rational part of my brain says, duh, of course I should. It's for safety. But my heart says, no don't do it, because then it would be too easy to wimp out of dressing each day. I'm excited about the fantasy of * having * to be Sherry, or else I can't leave the hotel room. Will I regret it, that's the question.
PS. I live within one day's drive (about 5 hours), so no flying/security is involved.