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A Bully Caged

A Bully Caged

by Candlelittrail
19 min read
4.8 (5500 views)
sissygaychastitybdsmcrossdressing
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Hello! All characters in this story are 18 or older. This story contains chastity, domination, cum play, semi-public antics, lingerie, and light sissy content.

This is the final part to this story, and I appreciate the patience of everyone who has followed it through. I enjoyed writing it a lot!

Let me know what other stories you'd like to see in the comments.

************************

The next morning, Wes and I wake up next to each other for school. In the almost-summer heat, we've decided to sleep with only a sheet covering us, and I can see every edge of Wes' naked frame. I reach to turn off my phone alarm, and I see a text.

"Unknown Number: I know what you two are doing."

[IMAGE ATTACHED]

I open the picture, and my mouth goes dry. I turn to Wes, who's still in a tired stupor. Once he sees the text and picture, he jolts upright.

The picture is of us standing by the water during our date, holding each other and kissing.

-----------------------

I look at the photo again. It's a good picture; I have my arms wrapped around Wes' waist, and he has his draped over my shoulders. It's a snapshot of a kiss between us, and even in the still, grainy image, it's easy to see the passion.

I close the photo and pull up my browser again.

Wes and I are in the bathroom, simultaneously trying to get ready and do investigative work about the mysterious photo and text I got in my phone. The number isn't in either of our contact lists or listed online, and the area code tells us only that the number is from Minnesota of all places. Wes brushes his teeth as he pulls up the ground-level view of the street near where the photo was taken from on his Maps app. To his credit, he pinpoints where the texter must have been standing down to a five-foot wide square, but finding out that the weirdo was standing between a bus stop and a parking kiosk ends up leaving us still pretty much in the dark.

"Why would they just take a picture of that?" Wes asks.

I know what he means. Considering the other things we did that night, including public oral sex and walking into a gay sauna, a picture of us kissing by the water seems innocent. Even still, both Wes and I are shaken. Someone took a picture of us without our knowledge and sent it to us like they're the masked freak in a fucking horror movie.

Wes seems especially panicked.

My own anxiety starts to ebb as I continue to get ready. Wes and I are college-bound, and even though we're both going to in-state universities, they're up north, and almost nobody else from our high school is traveling farther than 45 minutes from home. His friends from the soccer team, Joey, Chris, and some others, would certainly care, but I don't even know if Wes cares about what they think anymore. Besides, today is the last half-day of school, and with graduation this evening, we can write off this whole town if we want and make new friends at our chosen universities.

Wes keeps typing manically on his phone though, looking up the number, searching up how hard it is to track a text, and a bunch of other FBI-lite shit that has no chance of finding out who sent this text.

"Wes," I say. "It'll be alright."

Wes' face is flush, and he won't make eye contact with me. He just nods.

Before we leave for school, I tell Ms. Simmons about the text. She takes a look, and although there's nothing precisely illegal about what we've been sent, she still writes down the details and says she'll try and help how she can. Sasha, who's over for breakfast again, checks her contacts, but she finds nothing. Both she and Ms. Simmons are just wearing robes. Sasha's stayed over a handful of nights in a row, and with the way Ms. Simmons has been acting, I'm starting to wonder if this is more than sex for them. It looks like it might be an actual relationship. They've been doing yoga classes together. I'm happy for them, whatever connection they've found.

From then until we get to school, Wes hardly says a word.

Even when we pull up to the parking lot, Wes steps out as soon as I settle into the parking space. "I'm late," is all he says before he closes the door and speedwalks toward the building.

What the fuck?

-----------------------

My first class passes me by. There's only three hours of school for seniors, and then it's just the ceremony, so even if I listen, the thing of greatest importance that's going to be said today is "congratulations."

My mind is now firmly split between two subjects: one, the potential blackmail that Wes and I received, and two, the sudden cold shoulder I'm getting from Wes.

The blackmail is straightforward enough--I want to pummel whoever is at the other end of the line. The cold shoulder? I screw up my face. Wes and I aren't even going to the same college anyway. I'm going to Barnes, a private college, and he's got a scholarship to Northwestern. Maybe it would be best if this all died out now before it fizzled a couple months into classes. He would only be distracting me, anyway. I feel a twist in my chest at the thought of this, but I bitterly push it down.

During passing time, I feel a hand on my own shoulder, and I hear someone clear their throat. My back tenses. Even before he speaks, I can recognize who it is. It's Chris. "Hey, fag," he says.

Chris has called me this plenty of times, but now my blood boils. I'm past the stage of my life where I'll lay down and let people walk over me.

I turn and push his hand from my shoulder. His eyebrows raise. I've never done anything like that. He's the same height, as me. He has short bleach blond hair and a smooth-shaven face. If I recall correctly, he's going to college to play water polo, lacrosse, or another one of those rich niche sports. It's probably for the best that he figured out he was an athlete, because he would never have passed the eighth grade without coaches shuffling him along to the next classroom.

"What the fuck do you want?" I ask. Any amount of fear I once had is gone.

"You---I mean I need to talk to you," he says, looking up and down the hall.

"Fine," I say, "talk."

"Not here," he says.

I don't move. "Yes, here," I say.

Chris huffs and looks around again. "What the fuck are you doing to Wes?" He hisses.

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"Were hanging out now," I say, "so what?"

"He doesn't text any of the team back for weeks, and then last night I followed you."

A chill runs down my spine.

"You drag him to this gay ass restaurant, and then I saw you make him kiss you. What--what's that all for?" Chris turns his phone around and shows a picture--the picture. It's blurry and grainy, but you can clearly make out me and Wes holding each other and kissing.

My brain stops. This idiot is the one who texted me. What's more, he thinks I'm the one blackmailing Wes. this is like the criminal mastermind being revealed as Elmer Fudd.

"You made him suck your fucking dick, you--you freak," he continues. He's not as confident and sure as usual. His cheeks are red.

I ignore his primary concern, and I focus on the phone he's holding. It's cheap. "Are you using a burner?" I ask.

"Yeah," he says, stepping closer to me. "And I got all these photos backed up on a USB too.

"And you think that a picture of me and Wes kissing will what? Ruin our lives?"

"I got more than that. You both have scholarships on the line, and my guess is the soccer team at Northwestern wouldn't want a player who's on the wrong team."

I freeze. A video of me and Wes having public sex could certainly throw a wrench in any future plans. I doubt I could keep my scholarship to Barnes if something like this was sent to them, and Wes would definitely be fucked, both with his scholarship and socially. Then I narrow my eyes. If Chris had more, why would he not send that to us originally? "Show me," I say.

"I have a whole video," Chris mutters, his cheeks turning even more pink.

"I don't believe you," I say.

He pulls away the phone and is about to speak when I punch him in the stomach, barely grabbing the cheap smartphone before it hits the ground. My fuse is gone. I refuse to be held hostage by an idiot.

He doubles over, gasping for the breath that's been knocked out of him. I take a few steps back as he shakily moves toward me. The photo is still up on the screen, but as I swipe to see if there's more, a video pulls up. Chris wasn't lying about that. As it starts, I see Wes, shirt open and chest bare, gag around my cock as I fuck his throat. Even in the low resolution, you can see his face and body shining with drool as his chest heaves.

However, the image isn't very clear. It's shaking in a rhythmic up and down, and Chris' heavy, intermittent breathing can be heard through the tinny speaker. He's even... he's whimpering a bit.

"Were you fucking jerking off while watching us?" I ask, a pang of disgust and exhibitionist thrill hitting me.

"No!" He gasps, the air knocked out of him. He's crimson. "Give me back my phone!" He starts to stand up and claw forward.

I step back easily, taking the time to send the video to my own phone. It's loading, but it will still be a few minutes before it pops up on my end.

I continue the video, turning the volume up all the way so it echoes a bit in the now-empty hall.

I hear a break in Chris' recorded breathing before he speaks. "Fuck..." The shakiness of the camera filming me and Wes slows, and the camera angle drops a bit as he starts to put it away. Just for a moment, I see his own tiny cock in the corner of the screen, sticking out a pair of bright red panties.

I laugh. "No

fucking

way."

-----------------------

I watch Wes walk through the front door of the clothing shop near school. I'm waiting inside, peering over a rack to stay hidden.

I don't have any reason to hide-- school is out until the ceremony, and we're not doing anything wrong. As long as we're back in the next two hours, we're fine.

That being said, I take a moment just to look at Wes.

No matter what I do, and however I break him, he's always got this spark in his eyes--an indomitable spirit. His mess of blond hair is pushed out of his face, and his sharp features, which used to look scary to me, now come across as elvish. I can see his cheeks turn pink as he scans the store. Fuck, he's beautiful.

I had texted him only twenty minutes before:

"Found them. Meet me at Bravo across the street at lunch. Come ready to be fucked."

He had immediately sent me a flurry of texts asking for details and what I meant. I hadn't responded.

I pull out my phone and send him another text.

"Dressing room."

I see him jump as his phone buzzes, and after he looks at the screen, he makes a beeline for the back of the store.

I pop my head up and look over at the store clerk. I nod at him. A few days ago, I bought panties from the same clerk to give to Wes. Now I had slipped him fifty bucks to take an early lunch and head out for an hour. He nods back at me and heads out the front door, flipping the neon "OPEN" sign off on his way out. That on top of the money I dropped here before Wes arrived made him happy enough to not ask questions.

I follow Wes, making an effort to walk heel to toe, hiding my footsteps. I hear him creak open the dressing room door and let out a gasp.

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The funny thing about blackmail is how fragile it is. One piece of footage can be used to extort or coerce, but as soon as that shred of power is taken away from the scenario, all that's left is a very pissed off person.

I did not reverse-blackmail Chris. I could have, of course. I sent the video and all files to my phone before promptly dropping his burner phone into a toilet, and I now hold all the marionette strings that he was trying to pull. The difference between him and me is that I'm not a piece of shit.

No, I didn't blackmail him. I made him an offer. Now, as I turn the corner and see my handiwork in the dressing room, Wes and I get to stare at the fruition of that offer.

Chris is on his knees, blindfolded, and gagged with a pair of frilly baby blue panties in his mouth. His head swivels back and forth, trying to see us as we stand above him. A cheap blonde wig bounces around his shoulders. Low quality, whorish make up is painted on his face. His hands are secured behind his back with a pair of knotted string briefs, and his cock bounces and moves as the blood rushes through his body. I had thought that Wes' dicklet was small, but Chris' bare nub barely reaches two inches. But whether it's from the amount of water he drinks or just genetics, a huge amount of precum is hanging from the head of his dick, and the thin, syrupy liquid shines under the fluorescent bulb. He's not completely naked however; I have him wearing a blush pink bralette and garters, and I even found him some trashy pumps to match. I have a sharpie clipped to his bra strap, and it sways as he struggles to get comfortable. He's slim with strong legs, and since he's a swimmer, he's shaved and completely smooth.

"Looks like you're not the only faggot at school," I say.

Wes whips around. "It was Chris? Chris was the one who took the picture of us?"

"He took a lot more than a picture," I say, "but yeah. Also she likes 'Chrissy' when she's dressed up like this. She's a self-identified sissy."

"Chrissy" moans in protest around her gag, but her cock moves as a wave of anticipation moves through her. I have to admit, even though I hate Chris, Chrissy is growing on me.

"Jesus Christ," says Wes. Even though he's trying to play everything off coolly, his cheeks are bright pink. Seeing his longtime friend feminized and tied up in lingerie might be overloading him a bit.

I let a beat pass, the hum of the flourescent light filling the silence. "Turn around," I say softly.

Wes does, meeting my gaze for what feels like the first time today.

I breathe, trying to make sure that my voice is still as I speak. "I don't know exactly why things are the way they are between us today," I say, "but I need you to know that I want you in my life. I like you. I used to hate you--everything about you--but now I don't want you to push away, because I don't want to feel far from you."

Wes' cheeks burn brighter. He swallows. His eyes are filled with meaning as he blinks hard and speaks.. "My dad's going to be at the graduation ceremony today. With the text and everything... I'm just worried."

I feel numb for a second. Wes never mentioned his family. I knew he wasn't close with them, and even after spending weeks away from them, sleeping at first in Ms. Simmons' private room and now in the same bed with me, they had never once texted him to ask where he was or what he was doing. That relationship was already strained, even without this whole situation. I think about what I should say, but instead I step forward, gently taking his hand in mine, letting my fingers trace the lines of his palm. The corners of his mouth pull down slightly every few seconds, and he's trying to keep his watery eyes from crying.

I pull him in, placing one hand on his hip and the other on his rosy cheek, and while we're standing above Chrissy, we share a tender, quiet kiss. He wraps his arms around my chest, and pulls tightly against me.

Finally he pulls back, and he smiles slightly as he glances down at Chrissy, wiping the moisture from his eyes.

"This is fucking crazy," Wes says.

"Yes, it is," I say, taking his hand in mine again.

"So what do we do with 'her' now?" Wes asks.

"I told her that she would be able to tongue fuck you if she did everything I said."

Wes' eyes shoot up to mine. "You told him what?"

"Her," I correct him. "I told her I won't have you do anything you're uncomfortable with, but she's pretty fucking pent up."

Wes bites his lip and mulls it over, but I can already see that he's shifting his hips, moving back and forth as his cage tightens around his growing cock.

Finally, he nods.

"And you're not getting off so easily for giving me the cold shoulder all morning," I say. "" have a little outfit for you too."

-----------------------

It's not long until I have Wes in a similar getup as Chrissy. Wes is in an all-white bridal set, with lots of lace and sheer stockings pulled up to his inner thighs. His black plastic cage, black nipple and belly button piercings, and locked necklace stand out against the snow-colored cloth. He's bent over Chrissy, and his hands are on the wall behind her, his locked dick around her eye-level. His back is bent and arched, presenting his smooth ass to me. Fuck me heels push his pert ass up a few inches, making it appear even more supple and rounded.

"We should really be getting back," Wes mutters, but he pushes back farther to present himself more to me.

"I'll take however much fucking time I need," I say.

I put a hand on Wes' hip as I reach around, grabbing the sharpie that was clipped to Chrissy's bralette strap. She shivers as my fingers graze her cool skin.

I pop off the cap and crouch down, bringing myself only inches from Wes' smooth white cheeks. In thick, black letters, I write "W H" on his left asscheek, and "R E" on his right, spelling "WHORE," using his tight asshole as the central letter. Wes jumps and squirms as the cold, fragrant ink is left on his skin, but I grab his upper thigh with a vice grip, holding him still. He's breathing heavily.

I gently blow to let the ink dry before spreading his cheeks. His asshole is smooth and tight, but I can tell him that it's quivering in anticipation. I've practically Pavlovian trained his ass, and now he's happily expecting it to be invaded--violated. How different he is from the apprehensive jerk I knew only weeks ago.

I lean forward and give him what he wants, pushing my tongue deep into him. He groans. I move my tongue in a circle, loosening him and spreading drool around every fold. I gather spit in my mouth and push it into him repeatedly, letting it leak out as I pull back.

Without putting the cap back on the sharpie, I pass the marker to him and stand. He pauses for a moment, looking down at Chrissy before a nefarious smile crosses his face. He pushes up the bangs of her wig, and he brings the marker to Chrissy's forehead. She starts to thrash, but realizing that she's in no place to resist if she wants to see this out, she quickly slows, her shaky breath the only symptom of her apprehension. In clear capital letters, Wes writes "SLUT" across her forehead. On graduation day, too. I guess no matter how much he submits or reforms, a vindictive streak will always run straight through Wes. He doesn't finish there, and he crouches down to continue marking up Chrissy's bare skin.

I make quick work of stripping down, letting my hard cock flop out of my boxer briefs. Chrissy whines as she hears my pants fall to the floor. More precum dribbles from her tiny dick and pools on the dressing room floor.

I looked over Wes' shoulder at his handiwork. On Chrissy's chest, he scrawled "USE ME" and doodled a cartoon cock on her, and on her neck he wrote "CHOKE ME." Finally, on her crotch, right above her bald dick, he wrote "SISSY." Wes didn't pull any punches on the revenge here, and some of these words won't be easy to hide without bundling up. I have no pity though. With permanent marker contrasting against Chrissy's pale face and chest, she looked fully depraved--a full-on bitch.

I grab a handful of Wes' hair and turn his head away from Chrissy and toward my dick, pressing my thick cock against his lips. He opens his mouth, letting my head slip over his tongue. His eyes flutter, and he tastes my cock for the first time that day.

"Make it messy," I say, pushing more until I'm fucking his throat.

Wes obeys, letting his thick spit run down my shaft, slurping as he does, and I tell him to stand and turn again. I would've easily been able to breed his slutty mouth in only a few minutes, but getting his throat around my dick was for utilitarian purposes. I need my cock nice and slick.

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