Don’t remember our ages but I was a teen already and she was way younger than me I’m talking about my friends little sister. I was at his house playing outdoors when I had to use the restroom and walking by I saw her sleeping in her room with the door open and dared to step in and started touching her, my heart was pounding fast from the adrenalina of what I was doing and the fear of getting caught. The access was easy because she was wearing a dress. I did this about 2 or 3 times on different days. One of the times she woke up and saw me but didn’t say nothing and seem she enjoyed it. Now when I see her around I wonder if she remembers it and hates me for what I did but never really gotten any negative reaction from her or her family so I’m hoping she doesn’t remember and never told anyone about it.
I am answering this as if it were “dirtiest trick”.
Our church used to do a benefit Halloween forest walk. It was great fun. All the women wanted to be witches. No one wanted to be the vampire in the casket. I volunteered, because it was actually warmer in there, and I could read when the lid was closed.
We did a not-very-scary version early in the evening for families, then a more adult one later (think people jumping out from behind trees and chasing, not “adult” like naked). I added blood to my pointed teeth, white face make-up, frizzed up my hair. It was effective, especially when I popped out of the casket to Night on Bald Mountain.
At the end of the night, I just wanted to get home and shower. So I left in full Dracula make-up. When I got home, I had an idea. I slipped silently into bed and tapped my sleeping spouse on the shoulder. He opened his eyes, and moving faster than the speed of light leaped out of the bed. It was truly comical. He was not amused. He actually peed himself a little.
That’s the dirtiest trick I ever pulled in bed.