Skylar's BIGGEST Sleepover Wedgie!

                                    

                                          
Hello everyone! I wanted to tell the story about when Skylar and I had our first sleepover a week after we became friends. I know the 2nd story was the most massive one I gave him, but this is his first sleepover wedgie and it was pretty crazy lol! Also Just in case you forgot our ages from the last story, this was when I was 13 and he was 11. I asked him if he wanted to come to my house and sleepover, he said that he could stay and came over at around 4pm. When he got to my house we set up his sleeping bag right beside my bed, and we played video games for most of the night. Eventually it came to that part of the night where we just wanted to stay up in my room and talk until we went to bed. Skylar fell asleep in about an hour and I was trying to see how I could give him the BIGGEST wedgie of his life buuuut, one problem... he was in a sleeping bag that was zipped up and that would mean I would have to VERY CAREFULLY un-zip his sleeping bag without him noticing. I wasn't sure if he was a deep sleeper or not. I got the courage at around midnight to try and go for the plan I wanted to do. I walked over slightly to his sleeping spot on the floor in my room, and ever so quietly and slowly I un-zipped his sleeping bag without him waking up, which was a relief... I pulled the sleeping bag part fully off of him and and then lifted his t-shirt, I saw that he was wearing Hanes boxer briefs again, but except this time, they were red. I Stood over his back, grabbed his waistband with all my strength. Skylar's eyes flew wide open, a mixture of confusion, shock and something else, almost like a hint of amusement was on his face and he let out kind of a yelp lol. His underwear went all the way up to his shoulders and had a rip in them! I pulled his pj pants down to expose everything for extra embarrassment, and kept pulling. Skylar was laughing and having fun, while also struggling with the intensity of the biggest wedgie he's ever received! After a while of torment on his undies he held onto his butt with both hands almost begging at this point. I finished the extreme wedgie by ripping them off completely and his underwear was ripped to shreds in my hand and his bare butt full out in the open lol... Then Skylar says "Dude, that was the most intense wedgie I've ever gotten, that was really fun!" While still laughing about it. I asked him "Did you bring a spare pair of underwear?" He said "Yeah its in my backpack near the bottom." I threw him the extra pair, and he put it on. I knew at that moment for sure this time I had a forever wedgie victim and the coolest best friend I could've asked for. I said to him "for a dude who gets the worst wedgies, you're pretty cool!" We both laughed again, the bond between us was stronger than ever. When we drifted off to sleep I couldn't help but think how these moments filled with pranks, laughter and genuine connection were the true start of an amazing friendship, and I knew that no matter how many years passed, Skylar and I would always look back on that night and smile, remembering the time when a simple sleepover wedgie became a legendary story of our youth.