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Accidental Hook Hanging Wedgie
I was at a friends house when this happened (btw I’m 6’3 and 330 pounds so yeah). I was wearing just shorts and a t shirt but I was wearing cotton boxers. I was helping my friend with building a room inside of his building and we were working on the roof of the room. In the room there was hooks that we drilled into the concrete pillars (so they were extremely heavy duty). We’re putting boards in on the roof and my shorts were kinda sagging down because I didn’t have a belt on (big mistake). We finish putting up the board and I have to jump down to get more nails, the top of the roof was 7 feet so I had to drop down only like 5 feet cause my legs were hanging off. So due to sliding around on my **, my boxers were already kind of kind of in a wedgie (and they were loose so there is room in the leg holes). So the boxers I was wearing were loose in the leg holes but they were kinda stretchy. I hop down off of the ledge and I guess my leg holes were out because as I’m falling the hooks get caught perfectly on my leg holes and all my weight drops down and my boxers caught, so all my weight is pulled down and my boxers stretch to about mid back as I’m hanging in the air by my boxers. Not only did my ** get flossed and was burning my ** were squished so hard I almost cried. To make it even more embarrassing my shorts which were heavy slid down to my ankles so I’m in a hanging wedgie with my pants around my ankles. A bit of backstory my friend knows I have a wedgie fetish so he is laughing as I struggle in the most painful wedgie I’ve ever had. Due to me liking wedgies I start to get hard which makes it even more embarrassing. My friend says the only way down is to rip them and instead of cutting them he decides to jump on to my legs and pull me down which cause me to bounce and make the wedgie even worse. My boxers start to pop and he does this for about a minute straight until finally my boxers rip and I fall. I’m laying on the ground naked and I’m just rubbing my ** when my friend says oh hold on there still on you. And he grabs the underpart of my boxers and proceeds to rip the rest of my through my ** and flosses my ** so bad that my ** crack was bright red. My friend then let’s me pull my shorts up and we had a good laugh about it. So lesson learned always bring a belt.
I had some things similar a was go to girlfriends house her parents were away but they had a ring doorbell so I jumped over her neighbours fence to get in her backyard but when I was climbing the fence my jeans had sagged a little and then I jump down my underwear had get caught on top of the fence so I was in a hanging wedgie when my girlfriend came out and seen me she laughed and started pulling my leg in till my underwear ripped and then we went inside and she grabbed a pair of her young brothers Ben 10 boxer briefs to wear for the rest of the day.