Freshman year I lived with a roommate, and I sleep in my underwear in top bunk. One morning I was super horny and had to rub one out, so I pulled my underwear off and jacked off into it. I hoped that my roommate wasn't awake already and that I was quiet enough. After, I climbed down the ladder holding my wet underwear, and I saw that my roommate was actually awake in bed, looking at his phone. Sometimes I sleep naked, and he's seen me climb down naked before, so that wasn't such a big issue, but I was still obviously hard and holding wet underwear in my hand, so I was pretty embarrassed about that. Not to mention I don't know if he heard me jacking off the whole time; he never mentioned it, but I've done it once or twice more later.