Hanging Wedgie
Our house had a long driveway with a few turns, and trees covered the sides of the driveway from beginning to end. You couldn't even see the house from the road.
The tree that I really liked to climb was right in view of the driveway, so it wasn't very far from the house. It had a bunch of strong branches, and each of them was covered in leaves. One time I threw a Frisbee and it got stuck in the leaves, so we threw a soccer ball up to get it down. The Frisbee came down, but my beloved ball got stuck. That's just a faint example of how bad those leaves are.
My parents and sister left me home alone one day, and since I was bored, I decided to climb the tree. I got onto a branch, and sat there for a few minutes and then I decided that I wanted to get down. If I was standing on the ground, I wouldn't have been able to reach the branch, even if I lifted my arms up and jumped as high as I could. However, the branch wasn't too high up, but I was still a bit nervous about jumping down from it. I kept telling myself that it wasn't that high, that I had to bend my knees, and I'd be fine. I took a deep breath, and scooted forward, ready to fall.
I was falling feet-first, but then it happened. My feet went up in the back, almost all the way back up to the branch. My head was up too, so I was lying on my stomach in mid-air. Only my arms and legs reached for the ground.
"Huh...? What's happening?" I murmured out loud. I began to realize that something was wrong. I looked back up to the branch and saw my boxers sticking out of my jeans. "Oh great... hanging wedgie..."
I stayed in place for a short while, expecting the undies to rip. They didn't, and it was really starting to go deep and painful. I adjusted my position so my feet were at the ground and my head painfully smacked into the branch. I yelped in pain, and held a hand to the back of my head. The pain in my head faded after a moment, but it wasn't helping me in my situation. My boxers were unrelenting, leaving me hanging at their mercy. They were as merciless as the branch, which was refusing to break so I could get down. My front was very uncomfortable, and I began to kick my legs in an attempt to get down.
I shifted the weight from the top of my body so I was falling headfirst. My butt was exposed, and I would be even more exposed if I tried to climb out of it, leaving my boxers and jeans behind on the branch above. Besides, had I locked the door just in case my neighbor showed up...? I couldn't remember. It was either leave behind my clothes or suffer until my family returned home. I chose to suffer, thinking my merciless boxers would be easier to deal with than running around naked outside. I sighed, knowing it was going to be a long day for me as my boxers continued to stretch further.
Just my luck that today was the day I found out Breanna and Roxanne knew where I lived.
I was still hanging, the front of my waistband going over my bellybutton, when I heard... voices? Small, excited voices coming from the end of the driveway. Someone was coming, and the voices sounded female. I began to panic- I didn't want to be caught hanging by my boxers in front of a bunch of girls! I peered through the thick treeline, and vaguely saw two of them. I had no idea who they were until Roxanne's voice rang out.
"He better live here, you got it wrong the first time!"
Panic turned into desperation. I had a huge crush on Breanna, and I didn't need Roxanne endlessly poking fun at me about this wedgie. We all had the same bus route back then, and the country roads were easy to take on by a bike. I thrashed from side to side and kicked my legs. I wiggled and even grabbed my leg holes and tried pulling. Nothing worked, not even a faint ripping sound came from my evil boxers. Suddenly they came into view, still a good distance down the driveway and slowly riding their bikes. I thought I had a bit more time to try to break these boxers, but then I heard Breanna say something to Roxanne as she noticed me.
"Hey, is that him? What's he doing in that tree?"
"I don't know, let's go see."
My heart began to race as they began to ride their bikes faster toward me. I tried kicking again, and grabbed onto the back of the waistband. Breanna and Roxanne got close enough to jump off their bikes and run toward the tree. I was silently pleading with it to rip so I wouldn't be found in such a humiliating position, but then I lost my grip and fell back down to a lying position. My legs dangled weakly in the air. As I saw Breanna's eyes widen in realization, my arms went limp too. I could now only wonder how far my undies were stretching.
"Magni, what... happened?!" Breanna said in complete disbelief.
"I... got into a bit of trouble," I said, completely ashamed and mentally kicking myself for getting into this hellish predicament.
Roxanne had a wondering expression on her face, and moved over to stand behind me so she could better see my boxers caught on the branch. I heard her laugh, and could picture the delighted expression on her face.
"Hanging Wedgie!" Roxanne announced. Breanna's face went from concern to amazement to laughter in just a few seconds, and then both of them were laughing as I continued to hang by my boxers. They found a few plastic chairs on our porch, and brought them over to the tree where I was hanging before sitting down.
"Wait, you aren't going to help me down?!" I asked them. Breanna looked at Roxanne and shrugged before getting up and walking over to me.
"Here, I'll get you down," She said.
"Oh thank youUUUU!" My grateful thanks turned into a yell as Breanna grabbed my legs and pulled down, making the wedgie worse and my boxers stretch even more. I begged her to stop, and she gave me a few more pulls before letting go and stepping back with a curious look on her face.
"Huh, those are some stretchy boxers," Breanna noted.
"Yeah, thanks," I said as I continued to hang.
"You're doing it wrong," Roxanne said from where she was still sitting, "You have to jump up, grab onto him, and hang on until his boxers rip."
"Okay," Breanna said, turning back to me. "Ready?"
"No, NO!" I said, "Don't do it!"
Breanna reached up, and jumped. I cringed, expecting my boxers to dig in even deeper, but to my surprise I saw Breanna had grabbed the branch. She was trying to pull herself up, so she could get me down. Unfortunately, she couldn't pull herself up and kicked her legs uselessly.
"Rox, help me out here."
Roxanne sighed and walked over. She put her hands under Breanna's shoes, and helped her up. Breanna got up a little higher, and put a hand over to where my boxers were caught on the branch. She tugged at them a few times, and then I fell to the ground next to where Roxanne was standing. I put my hands to my front, and lie in pain for a few moments. I heard Breanna fall back to the ground.
"Hey, cool!" Roxanne said. I felt her grab the back of my boxers, pull them up, and then release to get a painful SNAP from my boxers. I could hardly walk, and I just lie in the dirt for a while. I fixed my boxers, and the two girls wouldn't stop laughing about how they had found me and my choice in boxers.
About an hour later, they were getting ready to leave and go back to Breanna's house. I was walking better by then.
"Hey, um, Magni?" Breanna ushered me aside so Roxanne couldn't hear us talking. "I'm really sorry about your... um... hanging wedgie..."
"Yeah... so am I," I said, flinching in memory.
Breanna suddenly threw her arms around me in a hug. She was bigger than I was, and with her white sweatshirt it was like being tackled by a polar bear. I was a bit surprised at first, and then I hugged her back. Behind her, I could see Roxanne watching us. I winked at her before putting my hands down the back of Breanna's pants. I grabbed her panties and yanked them up. Breanna squealed in shock. I was surprised to find that Breanna's undies were really stretchy, and pulled them up even higher. Since my arms were around her, I could feel Breanna stand up on her tiptoes. I could see a faint bit of green over Breanna's shoulder where her panties were. Roxanne put a hand over her mouth in a "whoa" as she stared wide-eyed.
Finally, I let Breanna go. She put her hands to the back of her undies, and glared at me.
"My pants are too tight! I can't fix this unless I take them off!" Breanna turned around to walk over to her bike, and I got a full view of her bright green granny panties with yellow polka dots sticking out of her tight jeans. I could faintly see her pantylines through her jeans, and grinned as I saw they were tightly wedged between her cheeks. Breanna unbuttoned her pants and managed to fix the wedgie a little. As she climbed onto her bike, Breanna told me she'd "definitely get me back."
I raised my hand in farewell as they left
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.
Stupid story.
Why wouldn't you just undo your jeans and let them fall to the ground and then drop out of your boxers then put the jeans back on.