The coolest "bad" thing I ever did was steal cakes.
There was this business conference at this fancy hotel next to our not-so-fancy hotel. My friend and I used to get into all sorts of trouble together, and it would usually start out by innocently exploring our surroundings. This time was no different.
The deserted conference room was resplendent with ice sculptures and flower arrangements, but dominating the room (by our way of thinking) was a tray of these little chocolate cakes with some kind of fruit filling in between the layers. We were going to eat a couple of the cakes, but my friend said, "I have a better idea."
He came back with a suitcase and stole the entire tray. In retrospect carrying a suitcase flat (necessary so as not to damage the cakes) is just as suspicious as carrying a tray of cakes, but in any event nobody saw us.
He was 13 and I was 14. We had just discovered girls, but as yet couldn't do anything but stammer and stare. Girls noticed us only to the degree necessary to maneuver around us in hallways and elevators.
There were these two girls at the pool. My friend and I were staring and wondering what to do. Then I got an idea: "Why don't we bring them room service?"
We struck up a conversation -- they were on vacation with their parents, big surprise -- and somehow the fact that we had cake allowed us to talk to them with confidence and pride. We had cake. These girls would surely find us irresistible.
When we brought them our cake tray their eyes lit up: "Wow! Where did you get that?"
We told them it was "room service".
They weren't buying it. Delight quickly turned to suspicion. "You stole it, didn't you?"
"Well not from our hotel."
"Hey, if we eat that we'll get in trouble. I think you guys better take that away before somebody sees you."
And with that they never spoke to us again. We laughed our butts off, though, when we went back to our room. To us this was a major breakthrough, as for the first time in our lives we actually flirted with girls -- and for a couple of seconds they flirted back! -- so we ate our cake in triumph and secreted the empty tray into an unused conference room the next morning.
For both my friend and I it was a rite of passage, our last acts as children. Before that vacation it was all about video games and secret stashes of fireworks, dog-eared porn magazines circa the Mae West era (or possibly Wilma Flintstone), and of course the very latest issue of Mad. When we returned we spent all our time either hanging out with my sister's cute friends or planning for same.
It was also the last time I ever stole.