This upstanding gentleman is about to ride an unofficial cyclocross race in Volunteer Park, Seattle. The theme is crossdressing, as a play on "cyclocross".
Cyclocross is a form of bike racing which requires the rider to navigate a course with obstacles so large that the rider must dismount their bike, shoulder their bike, jump over the barrier (or run up the hill, or wade through the water, etc), and remount the bike. As a general rule, cyclocross racers like beer and shenanigans.
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Also by Jessie Heaven Lotz
