Just a disclaimer: this isn't a wedgie I gave or given to me just a couple I witnessed in high school. This is also over 15 years ago, not that I think wedgies given by teachers is acceptable in any way but if it happened nowadays that teacher would have been fired on the spot haha. But they were fun to witness, not going to lie about that.
As a freshmen in high school in 2004, we all had to take PE. One of the "units" in P.E we had to take was wrestling. We had a wrestling room so the floor was all matted. At the end of one of the classes, my P.E. teacher starts messing with one of the nerdier kids in class. Just play wrestling. Everyone had left and I stuck around to watch. My P.E. teacher grabs the kid's arm and brings it behind his back. Pushes him down to the floor so he's on his stomach. He proceeds to grab the kid's tighty whities and pull up to maybe halfway up his back. He's laughing and the kid is squirming around, but doens't seem to be fighting too much or yelling or anything (maybe he thought it was fun lol). Then he lets go and we all the leave the room.
The second one I remember that my P.E. teacher gave was to one of the T.A.s (teaching assistants). We were outside on the grass in one of the fields. I honestly dont remember what activity or sport we were playing. But we were just kind of watching the teacher and the T.A. messing around on the grass. My teacher forces the guy down so he's kind of on his knees and pushes his head towards the ground. Then he grabs his green boxers and pulls up.
The last one I remember is after a badminton class. I was kind of sitting on the bench off to the side. Once again I see my P.E teacher messing with the nerdy kid (the same one who got one in the wrestling room). Again kind of playing around. One other kid yells, "give him a wedgie!" so the teacher quickly grabs the kid's tighty whities and pulls up about 2/3's up his back and I could see the legholes lols!