A Bully Caged Pt. 01

Everyone in the story is over the age of 18. This is my first piece of erotica, so let me know what you think!

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I sigh as I turn off my computer for the night. It's Sunday, and I'll have to be at school in less than 9 hours. Fuck. 

Yes, I enjoy my classes immensely, and it is the final two weeks of my senior year of high school, but Mondays are still far and away the absolute worst every time they roll around. I dread seeing... him. Wes. He's the ace of the soccer team, the most popular guy in school, and, most importantly, the bane of my existence. Every week, he finds a new way to torment me. At the beginning of the year, he was pouring coffee into my backpack every day, and right before winter break, he found a way to have them congratulate me during the announcements for being accepted to "Phaggett University." And he's never been expelled--not even once. He's got this charm, where he starts to smile and joke with the teacher talking to him, convincing them that, whatever consequences they're thinking of, they're too harsh. It's like he's untouchable. His silver tongue and handsome features don't hurt his cause, either. He's not tall, but he's striking, with sharp cheekbones and these big blue eyes. And he always keeps his grades up for some sports scholarship.

I will say, however, that the last week and a half has been paradise. I'm not sure why, but Wes has been gone from school since the previous Wednesday. I don't know what had gotten into him that last day, but he was worse than ever before. Besides his usual jerkwad behavior, he was talking about Ms. Simmons nonstop. 

Ms. Simmons was the lawyer of my moms, and their close friend. After both my moms got into a car accident a few months ago, I decided I'd rather live with Ms. Simmons than alone. I had only met her after my mom's passed, but she was kind, and I don't like being alone lately. Ms. Simmons, at only about 30, has meant the world to me since. It was her holding my hand at the funeral, burials, and everything after.

And Wes made it very clear: he didn't care about any of that. He said he'd spread her cheeks, sink his dick into her tight ass and... well, it got even worse from there. Had he been suspended? I doubt it; I had told Ms. Simmons, but the teachers wouldn't bother during our last month. Was he skipping? No. He's a bastard, but he's a good student. Well, either way, I hope that he's gone tomorrow too. God. I can't shake the feeling that he'll be there, waiting for me. I shiver. 

To take my mind off Wes, I decide to beat one out before sleeping. I stand and immediately jump into bed, pulling out my phone. It mainly doesn't matter what kind of porn I pull up; I'm bi. Nobody knows that, thankfully. I can't imagine what that asshole would say--or do--if he knew I liked men right alongside women. "Phaggett University?" That would only be the start. He'd probably beat the shit out of me. I grew up with two moms, and that had caused enough bigoted bullying for my taste.

I'm still finding a video when I hear a knock and Ms. Simmons' voice. I jump and pull my sweatpants up in a single motion--no easy feat. My dick comes up to my belly button. I'm a virgin through and through, but my libido and my dick are both oversized.

"Honey?" She asks. "Are you still awake?"

"Um, yes," I say, "I'm--I'm just meditating."

"Oh! Good for you, David. Can I come in?" She asks, already opening the door. Damn, I had forgotten to lock it. She was always talking about mindfulness, mental respite, and spiritual stuff. I knew she'd like that I was meditating. Not that I actually was.

I repositioned my body to hide my still-raging erection. I'd try to wrap our conversation up quick. "Well, what's up? Gotta sleep soon."

She's at the door, just wearing some thin pajamas. She's got deep brown eyes and olive skin, and her lips are turned into a smile. "I just want you to know that I'm getting you a graduation present, and I think you'll find out about it tomorrow."

"Um, thank you," I say, "but why are you telling me? Aren't presents usually a surprise?"

She laughs. Ms. Simmons is young and single, and I hate to agree with Wes, but she is still objectively attractive. Her smile makes her moreso. I try not to look at her that way. She crosses her arms, pushing her chest up. "Talk about looking a gift horse in the mouth. I just thought you might not recognize it as a gift if you didn't have some... warning."

I'm confused, but I want to get back to jerking off. "Well, thank you," I say.

"He'll introduce himself tomorrow," my mom says.

He? What? I had asked my moms for a tutor a while ago, but this is the end of the year. Maybe it's for college prep? I'm too horny to question it. "Alright," I nod.

Ms. Simmons just smiles and walks out. Did she sway her hips as she did? God, my horny brain can't be trusted. I just need to cum. I'm curious what she means, but my mind quickly wanders.

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It's already second hour, but there's no sign of Wes. Maybe my gut feeling was wrong, and he is still out. I look on the bright side: maybe he's dead.

"... Hey," a voice behind me says. It's quiet.

I nearly jump when I turn. It's Wes. His voice--I had never heard that tone or volume from him. Usually it was sharp and cruel. Now it was... timid. "Hi," I say. My voice sounds hoarse. I'm much taller than him, and I even have some muscle, but the idea of trying to fight someone makes my fists go weak.

He looks away and runs his fingers through his dirty blond hair. My eyes open wide as I notice his fingernails are painted black. He clears his throat. "Can I talk to you, David?" He asks. "Like, in private?"

The halls are full around us as the other seniors walk to class. "Um, where?" I ask. I'm nervous, but his voice sounds shaky and afraid.

"Locker room," he mutters.

"No cameras, no thanks," I say, shaking my head. No matter how scared Wes is, I can't trust him.

"You can..." he says, "you can have a camera."

"What?"

"You can film," he says. "I want to say sorry."

I look into his eyes. They're watery, and he's blushing, hard. Even his ears are red. Still. "So you can have video of me getting my ass beat? No way, man."

"I really want to say sorry. Please..." he whispers. "I'm begging you."

I hate that it happens, but when he says he's begging, my cock stirs a little. What the hell is going on? I bite my cheek before taking the bait. I know this is a bad idea, but I nod. "Quickly," I say.

We duck into the locker rooms. He even makes sure we enter different times.

When we get to the showers section, Wes looks at me. He's still red in the face. "Well," he says, "shouldn't you film, dumbass?"

"What happened to saying sorry?" I ask. I don't know what's made me so brave today, but I clench my jaw and hope I haven't just royally fucked up.

His eyes widen. "It's habit... sorry. You should pull out your phone to film."

Wes just apologized. Holy shit. I don't know what's going on, but it's definitely something. I've never heard those words from his mouth. Ever. I silently pull out my phone and start recording. "Okay," I say, "now what do you want?"

He nervously swallows and starts to take off his shirt.

"Whoa, Wes," I say, putting my phone down, "what are you doing?"

"You can keep filming," he says. His shirt is off now, and he places it on the bench next to him. "This... is my sorry."

I look closer. His nipples and bellybutton! They're pierced with little black jewelry! Holy shit. He's smooth. Like shaved smooth. My dick starts to wake up again. "Wes..." I say.

Next, he unbuttons his skinny jeans and pulls them down. His pubic hair is... it's shaved into a cute, blond heart, leading to a tiny black cage. I recognize it from some of the porn I've seen. He's locked in chastity. And it looks like a particularly small cage. 

"What the fuck, Wes?"

He's not done, though. He turns, and he arches his back a bit, and, with the reddest face yet, he spreads his smooth ass cheeks with his black fingernails, revealing a matching black-jewelled buttplug. I gasp. Now, I am fully erect, my cock pushing against my sweatpants.

"Did you get everything on camera?" He asks. He still has his ass spread for me. "I have to have this on video."

"Um, yeah," I say. "I did." From the heat in my face, I think I'm the one blushing now.

"You can... I was told you could inspect me if you want to," he says.

"What do you mean?"

"You can... you can touch, sir."

Sir? I guess that wasn't even in the top five strangest things with this situation, but it was still surprising to hear. I take a moment before deciding. This is much too personal and revealing--too humiliating--to be another prank or scheme. I step forward, putting the phone down so it's still filming us. I reach out. This feels surreal, like I've stepped into some alternate reality. I don't know how this came to be, but I'm not going to pass up the opportunity. I'm horny, and Wes is... I want to spit on him, do the things to him that he's done to me, but... he's beautiful. His ass is a lot more plump than I expected, and I trace my fingers across it. My hand touches his, and somehow that feels more personal than anything else so far. Finally, I touch the base of the plug. It's firmly nestled inside his asshole. My fingers find the lip of the flare, and I pull on it gently. He shivers a little. I push it now. He doesn't move. "push back when I push," I say.

He nods.

My heart beating fast, I decide to push my luck. "say 'yes, sir.'"

He pauses. "Yes, sir," he whispers.

Now I nod.

I start to push and pull rhythmically with his plug, just pulling by an inch before thrusting it deep inside him again. He pushes back. He's being fucked with the plug now, and his eyes are closed. I slide my other hand down his stomach, and suddenly I'm touching the plastic prison between his legs. I can feel his dick pushing against it. Now that I have it in my hands, I realize exactly how small his cock really is. Instinctively, I hold it tight and start to roll his balls between my hands. Fuck, they're full. his eyes are still closed, and his lips are parted.

Then, I stop completely. He shakes a little, but doesn't turn to me or say anything. I'm not going to give this motherfucker the satisfaction of cumming, even if he'd be ashamed after. Even if he's annoyingly sexy. Even if I want to touch him so much more. He's still Wes.

Suddenly, my phone buzzes. It's a text from Ms. Simmons.

Hi, honey. I hope you're enjoying your present today. :))

I look up at Wes. Suddenly the bizarreness of everything hits me, the haze of horniness disappears, and the shame of having my first sexual experience be in a locker room with my bully falls into my shoulders. "What the fuck is going on?"

He turns, and, with erect nipples and a straining, caged dick, he says "Ms. Simmons told me to explain to you over dinner... sir."