The Staycation - Wedgie Boy Story

Hanging to Dry

Part One: Hanging to Dry
       Recently my parents had left for a vacation which will last a month, and they decided to let me invite a friend over so that they felt safer about me being alone. I chose my best friend Jacob, who was a lot bigger than me, 5'4 and 150 pounds exactly, to my 4'9 and 90 pounds. I truly didn't know what this trip would turn into until he exposed his darker self.
       My parents left about 40 minutes before he arrived, my father telling me to give my friend his phone number as soon as he arrived, which I did. I had a bunk bed that I used by myself, which was convenient for my friend as he could sleep next to me or take the top bunk. As I invited him in, he greeted me with a "Hey Cheeks! How have you been this summer?" to which I replied "Amazing so far, I really can't wait for 6th grade next year!" I showed him to my room and he unpacked with the spare open section of the cabinet. "Do you mind if I put my underwear with yours? I feel weird setting it out in the open like this." My response was obviously "Of course dude, as long as we can occasionally swap undies!" He opened up my drawer and set his drawers next to mine, and I saw him eyeing my briefs as I saw his boxers and boxer briefs.
      Now just for a little back information, my mother and I both mutually agree that I should wear briefs. They're cozy and have my favorite characters, and I do enjoy being humiliated for my briefs on occasion. My father, however, thinks I'm a total nerd and wants me to change. I won't anytime soon though, so he has to live with it. I'm a 10 year old who wears tighty whities, colored briefs, cartoon briefs, and occasionally a pull-up, and that's how I like it.
       Back to the story, Jacob had challenged me to a video game dare contest in which whoever wins gets to ask the other person a dare and they have to do it. I'm not a lover of wedgies or anything, but I'm really hoping he gives dares involving my briefs, because I'm wearing my favorite pair of my dad's tighty whities just for him. (Yes, my dad wears briefs but doesn't want me to. Contradicting, right?) Of course he won the game, and his first dare was for me to take off my pants. I reluctantly pulled them off, slowly as I didn't want him to be suspicious, and there came my dad's huge, pristine white, comfortable tighty whities with his name on the waistband. "Holy shit dude, these are huge! "Thomas"? Isn't that your dad's name? Oh my god you're wearing your daddy's briefs, haha!" "It's nothing, my dad asked me to wear them!" I challenged, trying to avoid total embarrassment. "Yeah whatever tighty boy, just don't lose this next round or you'll really be in trouble with daddy." He responded. We played another round, which I tried much harder to win, but I still ended up losing. "My second dare is going to be letting me send a pic of you in your dad's briefs, along with a second photo showing the waistband name, to your dad." Jacob said, to which I replied "Hell no!" Jacob added on with "Well, if you don't, I'll be forced to tie you down, and possibly take a look at some "valuable goods" you have down near those briefs." "Okay fine, you can send him a picture. Just don't make me look too nerdy." I said. "Boy, you couldn't look MORE nerdy, you're lucky I'm not showing the whole school right now," he exclaimed. He took both of the photos, sending them to my father, receiving a seriously quick reply of "I knew he was going through my underwear. Make sure he doesn't take more than he has, and if you can, make him wet himself. Then, hang him up to dry."