On the Streets of Chicago – Crossdressing in the Rain

  • xdresser in the rain I recently made another visit to Chicago. Seems to be one of my favorite cities to crossdress in ;) Allie and I stayed downtown again, and it’s so easy to walk out on the street as a gurl there. Of course it always makes me a little nervous, but other than a couple looks (I mean, who wouldn’t look at a hot girl like me strutting down the sidewalk!) I was perfectly comfortable. I even worked up the nerve to ask the concierge at the hotel for an umbrella as we went out, which he provided with a smile :)

    In spite of the rain it was a rather pleasant night, and we walked the mile or so from our hotel to The Baton, the location of Chicago’s famous drag show. It’s a bit of a seedy bar with very overpriced drinks, but it’s right downtown and the show is worth it. Somehow we managed to score front-row seats! Nothing like looking right up the skirts of some of America’s hottest drag queens only inches away ;) It wasn’t our first time to the venue, as you might remember from a previous post about crossdressing in public. And after quite a few of those overpriced drinks, I managed to convince one of the stars of the show to pose with me for a photo. Unfortunately it’s not the photo you see to the left, as I’ve managed to misplace it somehow during my travels :(

    Speaking of quite a few drinks, after I stumbled out of The Baton Allie managed to convince me to stop for another drink at a downtown bar on the way back to the hotel. So there I was, all dolled up in my wool tights and high heels, walking in to an ordinary bar full of unsuspecting patrons who had probably never seen a crossdresser before, lol. If people were staring, I certainly didn’t notice – I was having the time of my life out on the town, fully dressed and pretty darn passable I’d say.

    Heading back to the hotel the rain let up a bit and became just a little drizzle. So I decided to snap a few photos dancing with a streetlamp under my borrowed hotel umbrella. Pretty classy, don’t you think?

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