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?