Shorts and Boxers Take a Tumble…

DownUp (+5 rating, 9 votes)
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I was eleven, and a lot of us were out by the playground for recess. My friends Pam, David, Angela, and Mike and Alex were teasing me a little, saying all day that I liked this girl named Kelly from my class. I guess I did like her, but I wasn’t going to tell them if they were going to make fun of me! I was always playing a lot of jokes on my friends to embarrass them around school and our houses, so they liked to try to embarrass me back when they thought they could. So Kelly was a little ways away talking to her friends, and it was hot outside so we didn’t want to run around, and Angela was just piggyback riding on me, wrapping her legs tight around my waist to hold on (I’m the smallest one of all of us, so I’m not sure why I was the one who would carry her and Pam around like that!). We just walked back and forth like that, and then one time around she climbed on in front of me, wrapped her legs around my waist, and we walked like that.
Well, after a little bit of walking I could feel my khaki cargo shorts starting to come down because of her legs wrapped around my waist, pulling them down. I didn’t know how to say it, cause I didn’t want everyone to know that my shorts were falling. So I whispered to her, Angela, you’re pulling my pants down! She just looked at me and bursted out laughing, and she said guys, come over quick, you got to see this! Something priceless is about to happen to Aaron, and he’s going to be totally embarrassed! She didn’t look like she was getting off me, and I couldn’t believe she was going to embarrass me like this!
Well, everyone ran over, and even Kelly and her friends came up to see what was going on! Angela wasn’t just hanging on tight with her legs anymore, she was playfully twisting her body around, and it was making my shorts come down even faster now. My face was turning beet red, and I couldn’t believe she would do something so embarrassing to me, especially with Kelly standing there watching and smiling shyly at me! I’m like, Come on Angela, don’t! Don’t pull my pants down! And then Pam said, laughing the whole time, OMG, I can see Aaron’s boxer shorts now! His shorts really are coming down! And my face went redder.
But then the most embarrassing thing of all happened. I felt my boxer shorts starting to slip down on my body! Yep, Angela’s legs were wrapped around my waist, and her twisting around and pulling down with her feet was actually pulling my boxers down with the khaki shorts! I screamed of embarrassment, and I said Angela please, PLEASE don’t pull down my shorts in front of everyone! She didn’t know my boxers were coming down too, so she’s like, What? Pretending she didn’t know about my shorts falling down.
My khaki shorts and boxers were both slid down to just higher then the bottom of my shirt, so the shirt was the only thing covering me from the worst embarrassment I can think of! Angela kept twisting, and laughing with everyone else (by now everyone could tell that my khaki shorts were falling down fast, and Kelly was actually sort of blushing in embarrassment for me), and I’m like Angela, PLEASE don’t, you’re going to humiliate me, my…MY BOXERS ARE COMING DOWN! I screamed, just as my shorts and my boxers both slipped down to my ankles, and everyone screamed when they saw my underpants sitting there around my ankles! I can’t even describe my embarrassment, but it was the most embarrassing moment of my life by a lot!