When I was about 14 I had an extremely long bus ride with very few kids on it. One day there was some sort of event or something and I was the only one on the bus for an hour and a half. Anyways I was really bored and I had just googled boobs on my flip phone and figured why not- hid myself under my sweater and went to town. I swear my bus driver knew what was going down. I was in the back seat, and I was trying to make sure he couldn't see me in that mirror thing and i was completely covered so I don't think he saw, but I'm pretty sure we made eye contact and his face just told me he knew I was up to something freaky. Also the post-masturbatory shame was immense when I had to ball up my sticky sweater and hide it in my backpack and come to terms with the fact that I just did that.
TL;DR jacked it while staring in my bus drivers eyes
My grandma used to live in Westminster, CA. She lived right behind an elementary school and I'd usually scale the school's fence to explore the playgrounds, play on the swings, etc.
One day, I decided to explore the campus and I decided to randomly try and open up the school's office- to my surprise, the door was unlocked. I let myself in, no alarm sounded, someone probably had left in a hurry... or would be coming back, no fucks given.
I made my way to one of the offices and just sat there. And then it hit me, let's masturbate. So I did, I jerked it and enjoyed myself for about 5 minutes. I hadn't thought about finding any tissues so I just came on the floor. Right in the middle of the room.
I just merrily walked out.
My buddy masturbated in the White House bathroom during a high school field trip. He still brags about it. And his name, swear to God, is Jed.
I was 15 at the time, watching TV inside a partly broken treehouse with my then "girlfriend". I put girlfriend in quotations because we couldn't really date each other, so we were mostly just friends with benefits (as in hand-holding action). An ad for Girls Gone Wild came on while we were watching Comedy Central, and things started to heat up. I mentioned how I had never seen boobs in real life. My GF turned around and took off her shirt without skipping a beat. I looked at her awkwardly for a bit and put my dick on them. She started rubbing my penis side-to-side with her boobs, and arms out kind of like an awkward penguin waddling around. This went on for about 10 minutes, and right as I came on her face, our mother climbed up the ladder and saw us. Thanksgiving was never the same again.
I am afraid of planes, so I take Amtrak trains down to florida from new york.
Anyways, i was about 15 at the time and me and my girlfriend just started having sex, and she went on the train with me down to florida with my mom.
We were laying on the top bunk of the train and the trains door led directly out to the next train, because we had a handicapped room... She started blowing me and just as i was starting to finish the conductor of the train opened the door to welcome us, and witnesses my girlfriend get a hefty facial.
TL;DR Amtrack Train and conductor watched me jizz of gfs face.