my older brother was a grade A bully my whole life. His go to was to make me make bets with him that he’d always win. I stopped playing video games all together because I started to associate them with being forced to smell his farts. I’d wised up though and stopped agreeing to any bets with him. But as much as I hate to admit it my brother is just smarter than me and he knew exactly what buttons to push to get me to bet with him again,
I’d recently started playing a lot of online chess. I wasn’t the best but I certainly better than most casual players. My brother noticed my new hobby and started teasing me about it. “Of course you love chess, nerd” “I don’t know what’s more embarrassing, you spending your free time playing chess with a robot, or that you always lose to that robot!” And eventually the comment he’d been building up to the whole time “You’re such a loser. I bet you couldn’t even beat me at chess”. I wish it didn’t but this caused me to look up from my phone. His evil eyes and cheeky smile goading me. “Seriously? Do you even know how to play chess?” My voice was dripping with annoyance.
my brother chuckled “of course! It’s just a bunch of knights and kings and wizards and shit that dorks like you play with on a board”. I rolled my eyes at him. “There are no wizards in chess”
“okay Dorkwad. Wizards or not I bet I can beat your ass at chess with ease”. There it was again. I should’ve just ignored him but feeling confident against my brother for the first time I answered “oh yea what do you bet?” This is when my brother’s face grew into a full on wicked smile. I should’ve known then betting with him was still a bad idea.
my brother feigned thinking for a moment but he had already planned all of this out. “How about…the winner gets to give the loser wedgies all night and the loser has to let them”. My brother raised his eyebrows up and down at me a couple times playfully.
The wedgie bet did embolden me further. Usually my brother’s bets were nastier. Fart sniffing or foot rubs. I’d even lost one before where my face had to be his deodorant stick for a whole week, that was a rough one. But just wedgies and for just one night? I deduced that meant he wasn’t confident in his win and didn’t want to risk subjecting himself to anything too brutal for too long. Of course I was wrong.
“fine. You’re on, wedgie boy!” I jabbed back at my brother. This made him laugh. “That’s the spirit bro!”
We made our way to the chess board in the den and while I did have whispered thoughts that this was not a good idea, that my brother could actually be good at chess, it was a cake walk. He didn’t play with any strategy just moving pieces on whims. Whereas I knew exactly what I was doing with each move I made. The game was fine in less than ten minutes. “Ahh nice job dork. I guess you win”. I was so happy I had finally gotten one over on my brother. “Ready for your wedgies, loser!” I tried my best to sound like him.
“Give me one sec bro. I’m actually free balling at the moment.” My brother played with his junk as he said that making me roll my eyes. He left to go out on underwear, or so I thought, and I started to set the board back up. I did take a picture of my dominant win first just so I could lord it over him for a while. I wasn’t pay attention when my brother returned though. In his hands were a roll of duct tape and two large zip ties. Before I had a chance to even compress what was happening he had my hands behind my back and was restraining them with vigor.
“What the hell dude!” I exclaimed as he jumped off me laughing at the sight of me,
arms bound behind my back.
“Uh oh dork, how’re you supposed to give me any wedgies with your arms stuck like that?”. He was playing dumb and really pissing me off.
“Exactly dude let me go!” I yelled at him. My arms pathetically swinging behind my back. “Oh wait I have an idea!” My brother spoke with a mocking tone. I saw his eyes grow dark and his smirk became slightly more aggressive. I knew that meant I needed to get away but I was already cornered. My brother was on me and had my head pinned face up on the den couch cushion in seconds. “There ya go bro. You won fair and square. So I have to let you give me wedgies allll night”. He emphasized the word have as he stood over me his legs straddling both sides of my body. “But without hands I guess your only option is to wedgie me with your face!” My brother then dropped his shorts exposing his crusty boxer briefs. I really started to struggle then but I couldn’t get up with my hands tied
“Don’t worry loser, I only wore these to the gym three times last week. They’re pretty clean”. Turning around my brother showed me his boxer clad ass. A light skidmark running up his crack. “Dude please don’t! I won this isn’t fair!” I begged as my brother began to squat down on my face. His ass and skidmark growing in size as they approached me until I was consumed in his musk.
“Ahhh there it is. Come on dorkazoid. Do your worst. I want my underwear wedged up my crack the farthest you can get it.” My brother teased as he rubbed his crack on my face pushing my face deeper and deeper. His ass stunk so bad. A combination of his unwashed dirty underwear and him never washing his ass either.
“Wow bro, this isn’t so bad. I don’t know why you’re always such a whiny baby whenever I wedgie you”. My brother teased as if the wedgies he gave me even compared to him shoving my face in his butt.
“Uh oh dork! I’m feeling a little gassy. I guess wedgie night is gonna be a lot more than you signed up for!” My brother cackled and all I could think was I will never bet with him again.
This is why you all need to start your own blogs so I can have more stories like this to read ☝️
