Chapter Text
Milo stared down at the map in his hands. How the fuck had he gotten lost on this damn campus again? He could’ve sworn the design building was on this street, and yet all he saw were the dumbass brick buildings of all the engineering buildings instead.
He sighed, staring at the map. Useless piece of shit. He slipped his phone out of his pocket, tapping the screen desperately. Why did the university wi-fi never work either? It would’ve been so easy just to follow the damn Google map.
He let out a heavy breath and stormed forward, shoes stomping onto the concrete. Right before he bumped into a heavyset lump of person.
“Uff! Uh, I-I’m s-sorry!” Milo squeaked, stumbling backwards, his phone slipping from his fingers, clattering onto the pavement. Good damn thing he had a phone protector.
“Long time, chocolate.” Milo gasped as the rough voice scraped against his eardrums. It was deeper than the last time he heard it, but still horrifically familiar. He felt his muscles spasm, freezing him in place.
Shit. Fuck.
He watched as a large hand reached down, plucking his unlocked phone off the sidewalk. “Funny running into you here. I was just thinking about you.” Kent said, sliding his thumb across the screen, his other hand slipped into the pocket of his ripped jeans, hips thrust forward in a… provocative show.
“C-can you, um, give t-that back,” Milo whispered, looking downwards, studying those leather boots, the shine, the rough lacing, haphazardly looped together into knots, fingers fidgeting. Kent hadn’t changed a bit.
“Sure thing, chocolate. Just wanted to share the app that made me think of you,” Kent said, his voice drawing out the syllables in a low drawl. He stepped forward, wrapping a large arm around Milo’s neck. “Check it out. It’s called Dirty Dares. They even send you a package. Should be at your apartment when you get home.” Kent chuckled, his mouth lowering to Milo’s ear.
He shivered, flinching as the warm breath brushed over his face. He smelled like cigarettes.
“Hope you enjoy, chocolate. See you in the lecture tomorrow.” Kent’s laugh kept echoing in Milo’s ears as he walked away, waving his hand as he turned the corner.
He glanced at the app on his phone. A simple back square with a red DD in the center. Like hell was he gonna keep a piece of shit app named Dirty Dares on his fucking phone. He pressed his finger against it and slid over to ‘Uninstall’.
Are you sure you want to uninstall this application?
Duh, no shit he did. He tapped ‘Yes.’
He tapped his foot against the sidewalk, waiting for the dumb thing to disappear.
The program has been uninstalled.
Thank god. He let out the breath he had been holding without realizing. Gasping in the fresh air. What the fuck did Kent mean by 'see you in lecture tomorrow' anyway? They weren’t even in the same fucking major, and he was a damn senior.
Milo shook his head and kept walking, back towards central campus. There was no point in finding the damn building anymore; he’d ask someone about it tomorrow. For now, he just wanted to curl up on the safety of his couch in his apartment. Maybe play some computer games, Minecraft or Stardew Valley perhaps.
He glanced down at his phone.
He gasped, almost dropped it for the second time that day. There was a black square with the red letters DD back on his home screen. How the fuck?
He pressed down on the app again, swiping to the uninstall–there wasn’t one. What the actual fuck? He released his finger, and the app opened. Shit. His fingers dragged downward on the screen, but the UI didn’t appear; he couldn’t exit the app.
Shit. Shit. Shit.
Plain black text scrolled across the screen: Welcome, Milo; User #1562! Initializing. . .
Fuck what was this thing? He hurried his pace, dashing down the sidewalk past the groups of frat guys, sorority girls, and various other organizations trying to get his attention.
Registration class: Submissive. Restrictions: None. Randomizing task list. . .
Milo’s breath hitched; he almost tripped on the crack in the sidewalk. Submissive? No restrictions? What the hell was it saying? He needed to find a hacker, or–or a comp sci student, or someone, anyone, to get this damn thing off his phone.
Task list randomized. Selecting first dare. . .Selected: Remove your shirt.
Heat rose in Milo’s cheek. What the fuck? What the fuck? He was running now, stopping only to spam the crosswalk button. He could see his apartment, and like hell was he going to pull his shirt off in fucking public. Besides, the app couldn’t do fucking anything to him anyway; it was an app.
Error: Dare Incomplete, Punishment count: 1. Searching photos. . .
How did it know? Shit. It had to have camera access. The crosswalk light had switched, so he ran across the street. He bumped into someone he didn’t care about. He glanced downward. Fuck. His photos were loading in the bottom half of the screen.
He was almost at the door to his apartment building. Almost there–almost–
His phone dinged. His screen was covered with an image. Of Kent. Of the guys–of his penis. He had taken it back in high school; it was–it was a joke. He glanced around. He was still in public. He clutched it to his chest.
Sending to contact, “Kent Moore.”
Milo squeaked, “No!” Stop! Stop stop stop! Cancel, fuck, why wouldn’t it do anything! He slumped down against the wall, frantically tapping on the screen, trying all the buttons, but nothing worked.
Sent.
FUCK. He was screwed. He was so screwed.
Ding!
He groaned. He didn’t want to look. It was fucking over. It was all fucking over. He peeked at the screen.
Kent: Wtf Chocolate
Kent: Wdy have a picture of my dick
How the fuck was he supposed to respond? His life was over. Fucked. It was all fucked. He dropped his head into his hands, phone thudding on the carpeted floor. He sniffled. Tears slipped from his eyes. He leaned back and heard a paper crunch.
Milo glanced behind him. It was an Amazon bag and a letter, taped together. Addressed to him.
His phone buzzed. The app had returned to that black screen.
Package Arrived at Location. Mandatory Task started: Read the letter and follow the instructions.
Milo flushed, tears still wetting his cheeks. If–if he–if he didn’t listen, who knew what the app could do. He couldn’t–didn’t have a choice.
Slowly, he grabbed the package. It was lightweight so that it couldn’t be all that suspicious. He shivered. He couldn’t prove that. Milo slid into his apartment, on the second floor facing the street, and laid it on the table, along with his phone.
He stared at them. His fingers lacing together, then unlacing. He took a deep breath. And picked up the letter. On the envelope was nothing but a small gold text: User 1562. He flipped it over and ripped it open.
The paper was rough, thick, and well-textured. Resume paper. Or some other fancy shit. The words were printed in loopy text:
Welcome, User 1562!
You have been registered as a submissive on Dirty Dares, with no restrictions! A&A recognizes that this is likely new to you, so we will provide you with all necessary products and instructions as you advance through your task list!
As a submissive, you are required to be outfitted with the shipped items at all times. Please follow the attached instructions to put on your new toy safely!
An image was located below, starting with a caption that made Milo flinch: Record yourself putting on your new cock ring, on penalty of an increase of the punishment count by five.
Shit. Below it was a series of images, depicting the crotch of a boy pulling his pants down, and slipping a set of three strange rings around his penis and balls. Fuck. Milo shifted his legs until he was sitting on his heels. He picked up the Amazon package and tore it open.
The contents fell onto the table, and the app somehow seemed to know. It flashed pink, and the text changed.
Point the camera at your crotch. Milo hissed, his breath leaving him entirely. His hands began to shake. He fumbled with the phone, only barely able to lean it against the table so that it pointed at his crotch. A small green checkmark popped up with a ding before the screen switched to the camera feed—small white text scrolling across the bottom.
Put on the cock ring. And right beneath it, a weird little icon, and the number one. A reminder of the punishment count, maybe? Milo shivered. He whined, his hands reaching for the zipper of his pants.
Shakily, he dragged it downward and popped the button free of its loop. He slid the rough fabric of his jeans down his thighs and slipped fingers under the hem of his boxers, brushing against his skin. He shivered. It felt wrong, sensitive. Hot. His face heated, and he gasped, dragging the silky undergarment down.
He glanced at the screen. Looked at his soft cock nestled between his balls, resting against his upper thigh. The number on the screen ticked up to two. He shivered, expecting a punishment, for something to change.
It never did.
Put on the cock ring. The text scrolled across the screen again. Milo took a deep, shuddering breath, trying to suck in the confidence he needed to keep going. It didn’t help. He reached for the plastic packaging around the rings. Ripped it free. The three rings were hinged, split on one side, and had a pad for what appeared to be a fingerprint sensor.
According to the image, the strange added bars were supposed to be pressed between his balls, and up the underside of his shaft. He shivered and took the largest ring. He settled it around the base of his cock and balls, and snapped it shut.
It beeped and tightened. Milo squeaked, fingers flying down to grip it. To try and pull it away. He couldn’t break it off. It kept squeezing until it was just tight enough to be felt, but not uncomfortable.
Milo whimpered. He hadn’t–hadn’t even thought about using something like this before. His legs shifted. It felt strange, he–he didn’t like it. Didn’t like any of it.
Put on the cock ring. The number had gone up to three now as the text scrolled by. Was it a timer? Something to tell him to hurry up? If it was, he needed to go faster. He reached for the next ring. He glanced down at the image.
This one went around his balls. He was supposed to tug them down and wrap the ring around the base. That way, the strange little bars would press between his balls. He had only ever touched there to pee–and now–now this. He shivered, whimpering again, short and high-pitched.
His hand wrapped around his balls. Squeezing. He hissed out, he had squeezed too hard. His balls throbbed. He brought the ring around them, and it clicked shut with a beep. Tightening like the last one.
The number ticked up to five. He hadn’t taken that long, had he? He-he needed to keep going. His fingers reached for the third ring, even as he kept his flushed face pinned to the camera. He couldn’t find it. He leaned forward, fingers stretching, searching, until they wrapped around the last ring.
He already knew where it went. Milo didn’t need to look. He placed it around the base of his cock, watching it twitch as the cold ring pressed against it, hardening just enough to look a bit bigger. It clicked around his cock, beeping like the last two, and tightening until it was snug.
The phone screen dinged, and the text scrolling across it changed.
Good boy.
The screen switched away from the camera; the number, which had gone up to ten, disappeared.
New mandatory task: Permanent house rule, you will remove your clothes upon entering the apartment.
Milo spluttered, collapsing forward against the table, choking on his own saliva. What the actual fucking hell?! Like shit, was he going to do that! He-he’d have to leave the damn curtains closed just not to be seen–he couldn’t–
Hesitation detected. Providing Motivation.
There was a faint popping noise in Milo’s ear. And then he was screaming, electricity zipped through his cock and balls. It felt like they were burning. His hands flew down. Grabbing at the rings. Flinching backwards as the charge arced to his hands.
“Fuck! Fuck!” Milo hissed, trying to stand up.
Please remove your clothes, User 1562.
Milo still hesitated. His legs quivered as he stood slowly, sniffling as he felt his nose leaking. He let his jeans and boxers pool at his ankles and reached for the box of frog-patterned tissues on the end table.
He sniffled again as he stepped out of his pants, wiping his nose with the frog tissues while his free hand reached down to pull his socks off his feet. He tossed the tissue into a nearby trash can before reaching and tugging his other fuzzy sock free. He already missed their cozy warmth. He liked fuzzy socks.
Lastly, he reached for the hem of the shirt and pulled the oversized fabric over his head, tossing it to the side, shivering slightly at the chill of the room, he wrapped his arms around his body, trying to cover his smooth body, his penis, his balls, just all of it, he couldn’t stop blushing, couldn’t keep himself from shaking, he didn’t even know what to fucking do.
Good boy, User 1562. The reward package has been shipped.
Milo gasped, his legs shaking as the rings vibrated in unison. The sensation spreading across his cock and balls. Seeping up his body, crawling down his legs, it was strange, not quite pleasurable, but it wasn’t–not–pleasureable either. Then, as soon as it started, it was gone. Milo whimpered, flexing his legs.
He squirmed, unsure of what to do. He stood there, waiting, until the phone buzzed again.
New Mandatory Task: Attend scheduled Doctor’s appointment at 3:00 pm.
Milo stared at the screen. Fuck. That was an hour away. It switched between tabs while loading Google Maps. Showing directions to a clinic he didn’t even know existed. A fifteen-minute drive. For a fucking doctor’s appointment? What the actual fuck? Why? Why did it even want him to go to the fucking doctor? It didn’t–
Fuck. He didn’t have time for questions. He needed to move. Or risk whatever sadistic punishment the damn app would force on him next. He stepped towards the door. And blushed. He was still naked.
He twisted, reaching for his clothes, pulling up his jeans. He didn’t put on underwear, didn’t have time if he was going to make it in fucking time. The shirt was only half over his head before he was out the door, shoes untied, keys in his pocket, almost tripping over himself as he dashed for the parking lot.
He slid into the driver’s seat of his car, panting, as he checked the clock, twisting the key. 2:08. He still had enough time, but he couldn’t hesitate; traffic was always fucked here, between pedestrians, red lights, dumbass drivers, you name it. You never got anywhere in the time Google said you'd make it.
He backed out of his parking space and took off onto the streets, honking at every slow car that got in his way. Up until he hit a red light. One of the longest red lights. 2:19. He was running out of time.
The light turned green. He drove as fast as he could, managed to avoid the rest of the red lights, and finally pulled into the parking lot of the clinic. 2:32. Plenty of time to meet the typical check-in waiting buffer. He let out a sigh of relief, pulled the car keys free, and slid out.
He stared at the building. It was rather large, with the words "Dr. White’s Clinic for Young Men." Plastered above the glass doors. They opened as he approached, and he strode in. Everything looked normal, a simple waiting room with plush chairs, a large front desk with a few receptionists, one of whom glanced up, her face beaming the second she saw his face.
“Oh! Mr. Reed! Just in time! If you’ll just step up here for a moment so we can get you signed in!” She said.
Fuck. How did they know his name? How did they already know his face? “Y-yeah, that’s me.”
“I’m aware, Mr. Reed, you might just be starting, but you’re already quite famous!” She giggled, typing into her computer, “Let’s see, looks like you’ve been booked for a standard health checkup along with measurements, fluid samples, a prostate exam, incontinence checks, and a few other routine checkups.”
Milo flushed. What the fuck? Fluid samples? A fucking prostate exam? This didn’t sound like a fucking standard procedure. He glanced down at his phone, the app still open. The words hadn’t changed.
New Mandatory Task: Attend scheduled Doctor’s appointment at 3:00 pm.
He took a deep breath, “Yep, that sounds right.” He whispered, his voice weak, shaky.
She grinned, “Don’t worry about it, it’s not that hard. If you relax, you might even enjoy it.”
Like hell would he enjoy any of this.
“. . .Alright, you’re all checked in, Mr. Reed, go ahead and take a seat, don’t mind some of the other boys, their prescriptions are always quite fun to see, and we’ll call you when you’re ready!” She declared, gesturing to the open seats in the waiting room.
He awkwardly made his way over and collapsed into one of the seats, his head falling into his hands. How the fuck had he ended up here? In a clinic with–he glanced to the end table next to him, covered in sexual health magazines–with those.
What the actual fucking hell had Kent gotten him into? He let out a long sigh and took a deep breath. Just as he heard soft footsteps shuffling towards him. A boy not much smaller than him, wearing an oversized sweatshirt that went down below his hips, hiding any shorts he might be wearing, stood in front of him.
The boy gripped the hem of his sweatshirt tightly, pulling it down as his face turned beet red. “U-um. S-sir. C-can I–c-can you–p-pat my head?”
“W-what?” Was this one of those prescriptions the receptionist mentioned? Fucking weirdos, was this some kind of exposure therapy or some shit? “S-sure?” He whispered.
The boy knelt, shuffling his knees closer, his head falling into Milo’s lap. Awkwardly close to his crotch. Milo slowly lowered his hands, running them through the boy’s hair. It was soft, almost like fur, so ideally, aken care of, Milo felt himself getting just a tad jealous of the boy.
Until he heard the sound that left his throat. Some mix between a puppy barking and a soft moan. The boy’s tongue lolled out. Milo flinched backward.
What the fuck?
“Mr. Reed? Dr. White is ready to see you now.” The voice gave him no further time to think about what had just happened as the boy leaped up, muttering a brief “T-thank y-you!” before darting away.
Milo took a deep breath and stepped forward, passing the nurse and entering the clinic's depths, still questioning what in the world was going on.