Work Text:
It was supposed to be a lazy sunday. A day for you to relax, and catch up on some tv shows. You were looking forward to a day for yourself, a day where I'd be out.
But when I stumble out of my bedroom, and see you making breakfast in the kitchen, I can't help myself.
You're wearing pink pajama pants, the type that are loose and comfy, yet undeniably curve around your butt, and I'm thankful. Your backside is such a visual feast. I approach silently, careful to avoid a floorboard that always creaks, and you tap your finger on the counter, waiting on the toaster. You have no idea I'm coming, no idea that I stayed home today. You thought it'd be a break from your bully roommate, didn't you?
You notice, eventually. You notice when I come behind you, grab your pajamas, and yank them to the floor. You squeak, and startle, then realize what's happening. You go to cover your butt--it's adorable how you try to stay modest, despite everything--but I catch your arm, and pin it against your back. "You--I thought you went out!" you say.
"My friend cancelled. And I'm glad he did." I admire your ass, fat and round and perfect, and my, what a pair you've chosen to wear today. It's a pair of women's boxers, black and lacy, with a stylish white trim, and I can't wait to ruin your backside with them.
Despite your impeding wedgie, you don't resist. Instead, you take a deep breath, and bend yourself over the counter. That's how it works between us. Six months ago, when it became clear you couldn't fully pay rent, you made a deal with me: you could live here rent free, and in exchange, I could bully you however I pleased.
I wonder, sometimes, if you regret that. But despite everything I've done to you--giving you wedgies as you tried to study, spanking your ass bright-red on your birthday, fucking you stupid on every surface of the apartment--you've never tried to call it off. Maybe you like me...
Just kidding. I know how sweet free rent is, and how humiliated you are every time I ruin you. I grab your waistband, and you tense up.
"Aww," I coo. "Don't worry, I promise it won't hurt."
"...I like this pair," you whine. "Please don't rip them."
"Mmm, no promises."
I rip the boxers up your ass, and the cotton strains wonderfully against my fist. It's tough, the type of cotton that doesn't stretch easily, and that means it's a challenge. How fun! It also means that it hurts like a bitch going up, and the loud, pathetic squeal you make is proof. You shake as the wedgie digs in, as your cute little boxers violate you, and I grin a big stupid grin. This is a good wedgie, one that'll leave you sore for hours, and the sight of your big butt being split is a wonder to behold.
"Fuck," you whine, "fuck..."
"What's wrong?" I say. "Is someone giving you a horrible wedgie?"
"No. You're too kind, and sweet, and generous, to ever to give me a wedgie."
Ah, how I love you. You follow instructions so well: three months ago, I joked that you should compliment me any time I bully you. And now, you follow it to the letter. It's so cute how embarrassed you sound when you're nice to me.
It doesn't save you, of course. I jerk your boxers up, and you squeak, knees knocking together. You breathe hard as threads audibly stretch, and it becomes clear this pair won't reach your head. Which leaves either ripping it, or...
"You're right, I am kind," I say "But isn't it kind to give a nerd like you a butt-busting wedgie?"
"...You're right, it sooo is. You're really nice to me..."
"Is that sarcasm?" I jerk your boxers even higher, and you quiver helplessly. It's practically a thong between your cheeks now. "If you think I'm so mean, maybe I should be. Maybe I should rip these right off you."
"Please, please don't! You're so nice! You're the nicest person I've ever met!"
"Good girl."
You shiver, just a little. Though you'll deny it, I know those two words excite you more than anything, and that me using them is the ultimate humiliation. How adorable... I let go of your arm, and get both hands on your boxers.
"Wait--"
"Don't worry, I won't rip them. But I think a dork like you needs a time out."
You fall limp, perfectly aware of what a time out means. There's nothing that can be done to save you now.
"Ready? Three, two, one--"
With a massive yank, I tear you off the floor, and you *squeal*. It's a nerd's squeal, a pure, high-pitched expression of 'oh god I can feel every thread of my underwear fucking my crack', and I laugh as you dangle from your adorable boxers. The wedgie is thinner than a thong now, just a line trying to cut you in half, and as you hang in my hands, it's like your brain short circuits. You're speechless, only whining as your underwear ravages your crack, and I bet if I could see your face, your eyes would be glazed over.
After a few seconds of letting your butt eat the wedgie, I carry you with me. Each step bounces you a little, earning me a pathetic little whimper, and I take you to a special hook we installed in the kitchen. It's one you're familiar with: how many hours have you hung from it, unable to escape as your panties dug deeper and deeper into your crack?
"Last chance to apologize, dork."
"I'm sorry," you bleat weakly, "I'm sorry--"
I drop your boxers onto the hook, and you whine, defeated, as the digs in. I step back, and admire my work: my god, you look like a *nerd*. Like an honest to goodness dork, who just pissed off a bully in the locker room, and got hung from their underwear as a result. I think about getting phone, and taking a picture, but before I can--
You pull up your t-shirt, and reveal your bra. It matches your boxers, black and lacy, with a white trim. "Please don't leave me up here?"
Fuck. I can't resist, and you know it. I come close, and bury my face in your chest, kissing your breasts. "Fine. But you should cancel your plans for the day. I'm going fuck you stupid."