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Wedgie Stories
These stories were taken fromWorld Wide Wedgie

Wedgie Key Throwing Pest
I was 16 and working as a lifeguard at a local swimming pool, and there was this family of 3 brothers who came swimming regularly. The younger two brothers were 7 and 9 and were kind of shy, but the oldest brother was 10 and always seemed to have a bright, mischievous, energetic expression on his face. I'll call him "Little R," and he was a great kid who liked joking around and seemed like a perfect wedgie target. But for the first few months, I never got an opportunity to wedgie him because they would always come when it was crowded and leave before the pool closed. However, one day I finally got a perfect opportunity, and I took full advantage of it. They came later than usual and went swimming as always, and this time they stayed until the pool closed, and actually were the last ones in the pool. At closing time they got out of the water, I finished closing up the pool and went into the lockers to get my stuff. Little R and his brothers were getting dressed next to my locker, so, I had a small-talk conversation with them for a bit, noting that Little R was wearing white briefs and these snug jeans that I consider perfect for giving a good wedgie. He was also, wearing a belt, and the three thoughts going through my head were (1) Should I give him a wedgie in front of his little brothers or figure out a way to get him alone, (2) How can I get him to do something to deserve a wedgie, and (3) If I can give him a good wedgie, he's going to have a *hell* of a time picking it out. . . . Well, the first thought took care of itself -- Little R's brothers finished dressing fairly quickly, and with a quick "We'll wait for you in the lobby!" they were off and running, leaving Little R and me alone. Little R himself took care of the second one -- he asked to see my key chain, which was from Florida since I had just gotten back from vacation there. I gave them to him, but when I asked for them back, he decided to play a little game of keep-away. After I made a few attempts to get my keys back from him, I said "You're gonna get it if you don't give me my keys back." He responded by saying, "Oh, I'm scared," then actually had the nerve to throw them to the other side of the lockers, laughing, pointing and having a grand old time. Regarding the third thought, this is what happened next: I decided to play around with him a bit and grabbed the back of his pants along with his belt and lifted him so, he was on his tiptoes, holding his shoulder with my other hand so, he didn't pitch completely forward. I estimated he was about 80 to 85 pounds, easily light enough for me to lift him with one arm. "I warned you," I said, and he was completely silent as I gave him this pants wedgie, which I knew didn't really do much other than prevent him from getting away. His pants were so, snug that a simple pants wedgie would hardly creep up his butt crevice, but nonetheless I enjoyed his reaction. He was all tensed up, saying a slight "Ahhh," tiptoeing forward as I walked him over to my keys. When we got there I told him "OK, I want you to pick my keys up and hand them to me, otherwise you're *really* gonna get it. " Still hiking up his pants I let him bend over to pick up my keys, but just as predicted rather than giving them back to me he flung them back to the side of the locker room where our lockers were. I turned him around to face me, and he had a huge smile, bubbling over with amusement, his eyes wide, mouth open in silent laughter, a pesky expression of "let's-see-what-you-got-big-guy" on his face that was annoying in a funny way, a way that made it clear that I had free reign to do what I wanted to get him back and he would know he deserved it because he's being a pest. Without saying a word I spun him, back around, reached down the back of his pants and grabbed hold of his briefs with one hand. I got the waistband high enough above the waist of his jeans to also, grab it with the other hand. I positioned him for leverage to give him a good two-handed bouncing wedgie, and started hiking away. "ahh... Ahhhh... AAHhhh.... Aa-eeeeEEEE!!" he said in rhythm to the bounces, getting a little higher and a little harsher with each bounce. Finally keeping him suspended by his underwear, knowing he was light enough there was no risk of rippage, but also, knowing that he briefs are jammed up his butt crack so, far that he would never be able to unwedgie himself if I kept him from pulling his pants down. I put him down and said "I warned you that you were going to get it!" He turned around picking his butt, his face all red and he was laughing like a maniac. He tried to go to another part of the locker room to unwedgie himself and I held him there and said "Oh no you don't, you're staying right here!" He started to unbuckle his belt and I grabbed his wrist and said "Oh no you don't, you're keeping your pants up!" We spent the next 10 minutes with him trying to unwedgie himself through his pants, reaching around, digging, poking, prodding at his butt in a futile effort to extract his briefs from out of his butt crack, and me giving him small refresher wedgies every so, often just to keep things interesting. By the time his 9 year old brother came down to say "Mom is here -- will you hurry up????" Little R was reduced to a useless pile of giggles, face red, hyperventilating, barely enough energy to get up and put his shoes on. "He'll be right up" I told his brother. I allowed Little R go into a stall to unwedgie himself and I retrieved my keys. As Little R got his stuff and was leaving the locker room, I said "I'm warning you -- if you do that again you're gonna get another wedgie!" He said in a voice dripping with good-humored sarcasm, "Oooooo, my knees are shaking!" I flinched and pretended to lunge for him, but he shrieked in laughter and ran out of the locker room. I hoped that another opportunity would present itself, but although Little R and his brothers continued to come swimming for the next few months, unfortunately I never got another opportunity to wedgie him again.




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