“Not my proudest fap” might be a joke, but what’s your most shameful fap, gentlemen?

When I was a pledge in a fraternity, I was given the task to jerk off in every room in the house over the course of 5 days. I systematically went from room to room finishing the downstairs and moving to the upstairs. I walked in this one guys room and he instantly woke up, I froze and stood there for a couple minutes until he fell back asleep. I proceeded to walk over to his closet and get behind the door. I went to town and right as I came, I tried to pull up my pants when my belt hit a metal shelf and made a loud sound. Next thing I knew, this guy was awake, and wanted to know what I was doing in his room. I proceeded to pull up my pants, make direct eye contact, and walked out of his room.

/r/AskMen Thread