Was 17 and scared but had chatted with a much older neighbor who saw me coming home one night dressed. Hair makeup slutty dress, you name it. He knew my family and had my number from before. I was scared to death but eventually started loving the attention and one thing led to another!

Was certainly what kept me up at night. Being a feminine skinny boy growing up, after seeing a penis in person the first time, it was my favorite fantasy. [edited by Moderator] I finally got my chance. Love masculinity and a cock is perfect representation lol

17 yo, was confronted by an older neighbor 61 yo who caught me coming home crossdressed. Being small - 5’7” 130 lbs at the time and feminine growing up, I would sneak out and drive around loving the attention from older men. Full makeup and my natural hair. It took him awhile to confront me but he did by text and said he was looking out for my safety. From there, we talked a lot and eventually evolved to hanging out with him allowing me to experiment. We played for a year and half