Naked at night in Deerfield IL
I grew up in Deerfield IL north of Chicago. My parents lived in a ranch house and my bedroom window looked out on the side yard. In the summer between my junior and senior years in high school, I started sneaking out of the house around 3:00 a.m. by climbing out my window. I'd immediately strip out of my pajamas and go walking around our neighborhood in the nude, sporting my raging 8" teenage boner.
At first I stuck close to our immediate neighborhood. But as I did this more and more often, I soon realized that nobody could see me (the residential streets in Deerfield are poorly lit) and nobody was around. If a car ever approached (like a cop car), I either saw it or heard it in plenty of time to find cover. So I got bolder.
We lived about a mile from the high school. I started walking there in the nude. Once on the school grounds, I walked all around the perimeter of the building and all around the surrounding athletic fields. I'd find a nice spot to sit down against a tree or on a bench so that I could masturbate while taking in my surroundings and thinking of all the girls that I wanted to fuck right then and there.
My best friend lived in the opposite direction of the high school, a full two miles away. I walked to his house in the nude. I'd sit on his front porch and beat off over thoughts of him fucking me right there in his front yard. I wanted him to buttfuck me so badly.
I got so brazen doing this that I was often gone for over an hour, climbing back into my bedroom through the window at 4:30 a.m. sometimes.
I never got caught, and the orgasms I had were intense to say the least.