My first time out was years ago when I just started college. I was living in Boston and there was a park nearby with some secluded spots. Rode my bike out at night wearing some cute panties and a sports bra under a dark men's shirt, with a summer dress, breast forms and wig in my backpack. Changed into my summer dress behind some bushes at the park then biked around the place for 5 miles. That feeling when the wind blew through my summer dress was just unbelievable. I wasn't too concerned with getting caught because it was dark out and I was biking fast enough that no one would get the chance to take a second look. I started doing that almost every week for close to two years.