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A wedgie where the victim is hoisted up to the top of a flagpole by their underwear. This is the best form of wedgie if you want the victim to suffer the longest, and if done in the summer, can last for days.
I gave this nerd called Jake a flagpole wedgie during summer vacation. I stripped him to his briefs and strung him up on the flagpole, giving him water and canned beans three times a day. I managed to keep this nerd up there for six days, and by the time a construction worker got him down, he was a mess (his underwear was his bathroom) and he couldn't walk cause of the pain in his butt. I still wedgie Jake to this day.
by Rappunk799 June 16, 2014
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i am a victim of wedgies to bullies. once i came to school early. unfortunately, so did the bullies. they saw me. they ran to me, took off all my clothes except my white undies, tied me up, carried me by my undies to the flagpole, made me drink five big glasses of water, and lifted me up by my undies to the top of the flagpole. one of the bullies videotaped the whole thing. the flag pole is REALLY high. every kid in school saw, and they laughed and took pictures and videos of me. i kept peeing. the buses left, and the teachers were at a meeting, so two hours after the buses left, one of the teachers saw and got me down. i was in that wedgie for 10 hours. my butt still hasnt recovered from that flagpole wedgie.
by Christopher Diddise March 11, 2008
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When your tighty whities are attached to the rope on the flagpole and then they raise it and that gives you a wedgie.
About two months ago, my parents went on a three week cruise. I got to school early, the bullies were waiting for me because they knew I wear tighty whities. They dreesed me down to my underwear and made me drink five huge glasses worth of water. It took so long for me to drink the water that by the time they had duct taped me to the rope, I was peeing on them. They lowered me, put ice in my underwear(it as winter) and started twisting my balls. OOOOOWWWWWW!!!!! This was a flagpole wedgie and they raised me up the full length and that is so high that the teachers never saw me. The only times they ever let me down was when the bullies fed me cafeteria food, EEEEWWWW!!!!, and made me drink water so I would pee and poop a lot. I wear extremely strong and stretchy so my tighty whities never ripped. Three weeks after I was raised up, my parents came home and called the police because I wasn't home. The police found me half naked attached to the flagpole covered in pee and poop! I was in that wedgie for three weeks and nineteen hours!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! My older brother ripped the undies out of my asshole and that taught my nuts, penis and ass to not lett my brother near them.!!!!!!!!!!!! One kid had set up a video cam running the time that I was fed, watered, and raised. I couldn't change schools because that would be pointless. The asshole who taped put it on the web and the online yearbook. I was on CNN and News Channel 5.
by Briefboy September 21, 2008
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A hanging wedgie, executed on a flagpole instead of any other object.
I was in the classroom and the teacher had to leave for 5 minutes. We were all sitting there and the girl bully saw my undies sticking out of my pants. She yelled TIGHTY WHITIES. Everyone Jumped at me and stripped me down to completely nothing but White strong tighty whities. They then dragged me by my underwear to the school's flagpole and attached them to the pull string. Then they pulled me all to the top and I Was sky high on a flagpole hanging wedgie. I cried because girls and everyone saw me up there naked only in briefs. I was often fed by the girl bullies but then raised back up. It sucked! I pooped and pissed by underwear like 10 times in 1 minute. 2 Weeks later though a MILF teacher saw me and got me down. I needed counseling. Hanging wedgie nerd is what I am.. A flagpole wedgie..
by Liam72 March 26, 2014
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First you find your nerd. Then you grab their underwear, lift them, and take them to the flagpole. Once there tie the flagpole rope through the underwear leg holes and lift to the top. This is the best to make them suffer
So as a proud bully I have hung many a nerd by their underwear There are two stories though that are my favorite

The first was a nerd named Devon. You see Devon was a nerd that literally no one cares about. So one day of my senior year I decided to offer him a ride back to his home. He accepted and the second that he got in I shoved a used jock strap in his face. The smell knocked him out. I drove him over to this abandoned summer camp my parents bought for me to own and possibly renovate (never). I stripped him to his tighty whities and gave him the flagpole wedgie. He cried like a bitch and since that day, every day, I go back to feed him. His underwear is his bathroom so it is bad. Yes he’s still hanging. There’s still a missing persons case out for him. These extra strength briefs are the best! Hahahaha
The second was Willy. On my freshman year I wanted to prove I was cool so I took this nerdy senior and gave him a flagpole wedgie. Sadly his underwear was weak. He ripped and fell 20 feet down.. poor Willy..
by Bullybro March 11, 2018
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