Challenge Eight

Posted originally on the Archive of Our Own at http://archiveofourown.org/works/25333873.

Rating: Explicit
Archive Warning: Choose Not To Use Archive Warnings
Category: M/M
Fandom: 13 Sins (2014)
Relationship: Elliot Brindle/John Witter
Character: Elliot Brindle, John Witter (13 Sins)
Additional Tags: Minor Violence, Sexual Roleplay, Alternate Universe - Canon
Divergence, Explicit Sexual Content
Language: English
Collections: Anonymous
Stats: Published: 2020-02-08 Words: 3035

Challenge Eight
by Anonymous

Summary

Instead of getting his arm cut off, John gets something else he's been fantasizing about.
Courtesy of Elliot.

In this game, failure wasn’t an option. Life was doing everything it could to screw Elliot over. The
loss of his job, debt that just kept growing, his brother’s cancelled insurance, a lost library card that
would link him to the dead body incident in the restaurant... and now he was on a bus that was
being driven by a weird clown. Only time would reveal the destination, but no matter what, he
would succeed in this next challenge.

By the time the bus came to a stop in the middle of nowhere, the sky had turned dark. Clouds
shrouded the full moon, but the neon sign was as clear as day. Hotel, No Vacancy. Where were all
of the guests? The parking lot had only two cars. A single light was on, illuminating the eighth
room on the second floor. He climbed the stairs that led there, intuition telling him that his
challenge was inside.

A key was waiting in the doorknob. The keychain had a number eight and a Latin phrase on one
side, and the other side had a picture of a fly with the same phrase. Thirteen Roman numerals were
arranged in a circle around the fly. It brought back memories of having to eat the crunchy insect for
his second challenge. He turned the key and opened the door slowly, his earlier confidence
becoming apprehension as to what this challenge had in store for him.

Against the back wall, a young-looking man was sitting on a chair. His brown hair was perfectly
groomed, and he was dressed in a white shirt with a tie, black pants, and fancy shoes. His clothing
was a stark contrast to Elliot's cartoon rabbit shirt, old jacket and jeans, fingerless gloves, and
sneakers. An empty chair was beside him, and a lamp rested on the carpet, creating a circle of soft
light.

“Hello,” the man said quietly.

“Hi.” As Elliot closed the door, he didn’t take his eyes off him.

“Um... I’m sitting here, replaying the sequence over and over. You get used to things, you know?”

Elliot didn’t quite know. “Okay...”

Cautiously he approached the man, looking him up and down. He sat next to him and scanned the
almost empty room. Just the two chairs, lamp, and a desk.

The man stopped fidgeting just long enough to reach into his pocket. “Gum?”

“No thanks.” Elliot turned his attention to the door, brow furrowed in confusion. He was in the
right place, but there was nothing here to guide him. Just a nervous guy who kept swallowing and
staring at him.

“You know, um... you kinda have this thing in your head... and it actually gets you. You know?”

“I don’t know." Elliot raised his eyebrows at him. "You got some kind of fantasy I should know
about?”

The man leaned closer to get a good look at Elliot’s face. “You didn’t go to Holmes, did you?”

“Holmes Middle School? Yeah, I did.”

“Did you have Metal Shop with Fishman?”

“Uh-huh. I’m Elliot Brindle.”

His old classmate extended a hand, which he hesitantly accepted. Middle school hadn’t been a
pleasant experience. He’d been a geeky kid, the target of constant bullying.

“I’m John Witter.” A few seconds of awkward silence passed before he continued. “I was in real
estate for a long time. Made good money. But I had some reversals.”

“Do you want to tell me what you’re doing here, John?”

He opened his mouth, but before he could reply, Elliot’s phone rang. It was the circus ringtone that
could only belong to one caller. Elliot bolted to his feet, answered his phone, and took a few steps
away so the familiar voice wouldn’t be overheard.

“We’ve gone through a great deal of effort to arrange this reunion. You don’t remember Johnny
Witter from Mr. Fishman’s class?”

Elliot shared a glance with John, who swallowed nervously. Of course he remembered.

“How he and his brother Tom tormented you daily? How they held you by the ankles out of the
computer lab window? Challenge eight is worth a hundred thousand dollars. Do anything he asks
of you, no matter how... unsavory it may be.”

“Unsavory?”
“It’s your right to decline, of course. But if you don’t complete all thirteen challenges, you’ll forfeit
the grand prize and everything you’ve won. Good luck, Mr. Brindle!”

The line went dead. Elliot slid his phone into his pocket and turned to John, who was still fiddling
with his hands. After what seemed like an eternity of silence, the request came.

“I want you to... humiliate me.”

Elliot stared at him with his mouth open. “You want me to humiliate you.”

“Yes.”

More silence followed until a sudden transformation came over John. He stood up, his mouth
curling into a sneer that reminded Elliot of those disdainful looks at school. Like he was complete
trash and not worthy of the air he breathed.

“You have no right to back out of this,” John spat. “I knew you were gonna pussy out. I knew it!”

Elliot raised his hands in an attempt to calm him. “Look, I know you’re trying to—”

“You’re gonna give me fucking sympathy? Are you for real?” John stepped toward him and halted
inches away, hands clenched into fists. “You’re fucking sickening. You know why we always
picked on you? ‘Cause you fuckin’ asked for it! You walked around with that stupid look on your
fucking face, saying please punch me in my fucking throat.”

Elliot just stared, his face blank.

“The day after we threw you into the dumpster, you passed me in the quad and you smiled at me.
You fucking smiled at me! My brother pissed on your brother’s face. You remember that? Can’t
tell me you don’t remember that.” A wicked smile crossed John's face. “I do. I bust a gut every
time I think about it. And you know what else I think? Your little faggot brother wouldn’t have
minded if we—”

John's tirade was cut off by a backhand to his face, but the shock wore off quickly, becoming
another smile. “Hell, I bet you wouldn’t have minded. The two of you were always a bunch of puss
—”

Another backhand, this time making him grunt in pain. His pants looked tighter than before, and
now it was Elliot’s turn to sneer.

“Jesus. You’re actually getting hard from this.”

John averted his eyes, no longer smiling, a hint of redness appearing on his face. The situation was
getting more clear. Elliot cupped John's jaw and forced their eyes to meet.

“Is this your fantasy? The bully becoming the victim?”

John jerked his head away and stepped backward to the exit while Elliot stalked him like a hunter
with his prey. The sick bastard wouldn't be leaving so soon. Not until Elliot was done with him.

“They..." John resumed his fidgeting at the door. "They said they would pay me to meet you, but I
don’t want the money anymore."

He turned to the door and reached for the knob. He was the only thing preventing Elliot from
walking out of here with a hundred thousand dollars. Elliot slammed his palm against the door,
keeping it shut, and leaned close to John’s ear.

“What happened to that part about being a pussy, huh?” He unbuckled John’s belt with his other
hand. “You know what they say about bullies. They’re compensating for something. Are you
compensating, John?”

He didn’t answer, standing as stiff as a board.

“I guess we’ll find out.”

Elliot undid the button and zipper on John’s pants and then yanked them down, exposing his rather
round ass. He tried to ignore the sight, not understanding why it would even appeal to him. John
wasn’t wearing underwear, but that wasn’t the most surprising thing. A foil-wrapped condom had
spilled out of his pocket. Elliot picked it up and shook his head disbelievingly.

“You brought a condom? What a fucking whore. Turn around and let me take a look at you.”

John stepped out of his pants and turned around, avoiding Elliot’s gaze. Contrary to expectations,
his hard dick wasn’t particularly small. Just average. Even so, Elliot snorted with amusement.

“No wonder you’re such an asshole. Not exactly well-endowed, are you?”

John bowed his head, more redness spreading on his face. What would it take to truly humiliate
him? Elliot’s phone was silent, failing to offer the familiar chime that signalled the completion of a
challenge. Maybe there was only one solution—one that made him say a silent apology to his
fiancé.

“Face the door.”

“No.” John looked up, eyes wide. “I told you, I changed my mind.”

Elliot patted him on the shoulder and gave him a half-smile. “No backing out. Now face the door.”

He couldn’t believe the words that came out of his mouth. The things a man would do for money...
disgraceful things, but at the same time, they brought a sense of power. John, the childhood bully
who’d made him dread going to school, was now following his commands like a little bitch.

With the condom still in hand, Elliot unzipped his jeans and pulled them halfway down his thighs,
along with his boxers. John shivered and pressed his palms against the door, but he didn't make an
attempt to open it. This was his true fantasy that extended beyond humiliation. A sick game that
Elliot was being forced to play. The alternative? Possibly spending his life in prison. But if he
completed these challenges, the charges would go away. That's what the strange caller had
promised during the bus ride here, and it was a comforting thought as he stroked his dick to
hardness.

Even with the lubrication on the inside of the condom, it was a struggle to get it on. Elliot’s hands
were trembling, realization striking him. He was going to fuck a man for the first time. When the
condom was finally secure around the base, he spent a few seconds just staring at the blatant offer
in front of him. Maybe it wouldn’t be so bad if he pretended John was a woman. His ass was a bit
muscular to belong to a woman, but...

Elliot shrugged, one hand gripping his dick and the other holding John’s hip to keep him steady.
There was a first time for everything, and despite his lack of experience with men, he'd never been
the bigoted sort.
“Spread your legs.”

More compliance. It sent a thrilling shiver through his body from head to toe, leaving him achingly
hard. He tried to push in, meeting tight resistance that was joined by a sharp inhale from John. The
condom had some lubrication on the outside as well, but not enough to lessen the risk of breakage.
Elliot released his dick and spat in his hand, then slicked himself up the best he could. He was no
expert on this, but he reckoned it was going to hurt. Good. John deserved the pain.

“Can you even find your fucking dick? Or is it too—fuck!”

This attempt was successful, resulting from a surge of anger. Elliot was many things, not all of
them good, but he wasn't small. As the head of his dick popped inside, he was unable to contain his
groan. The heat and tightness were better than anything he’d ever felt, and he almost wished the
condom was gone so he could feel even more. He pinned John’s wrists to the door and continued
to sink into him slowly, watching in awe as the inches were swallowed up. John’s pathetic
whimpers were ignored.

“Please... fuck, it hurts.”

His ass was so accommodating, despite his legs being on the verge of collapse. There was nothing
left for him to take, balls pressing tight against him, and his whimpers turned into ragged breathing
as he tried to adjust to the buried dick. It was already throbbing from the intense warmth and
pressure that surrounded it from all sides, and Elliot hoped he would last long enough to thoroughly
punish his victim. He inhaled deeply against John's neck, smelling aquatic cologne that made his
head swim. For a brief moment, he forgot this was just a challenge. Instead it was simply a way for
him to find some pleasure in his life’s downward spiral. But then realization came rushing back.
He'd done a lot of things to get here, and there was still work to be done. This was business and
nothing else.

“You just gonna fucking stand there like a cowardly fuck?”

John’s question, tinged with pain, was another reminder of the incomplete task. It wouldn't take
much longer with his ass gripping Elliot's dick so perfectly. A fast pace was set, drawing an
occasional sob and fake plea for him to stop, and he watched every second of it while keeping
John's wrists pinned. The sight of his dick sliding in and out was hypnotic, as were the slick sounds
and the slapping of skin that accompanied each thrust. Blood trickled onto the carpet, but it only
made Elliot more determined to punish him.

He grabbed a fistful of John’s hair and yanked his head back, smiling at the tear tracks that
extended from his eyes to his jaw. “How does it feel to be used like a whore? Huh?”

John couldn’t answer, breathless groans pouring out him, and Elliot released his hair to pin his
wrist again. Unsurprisingly, the whore was still hard. His dripping dick wanted attention that Elliot
wasn’t going to give. He didn’t even have to give any. Whenever he angled his thrusts upward,
John cried out with his favorite word. To see and hear him be so vulnerable, unable to do anything
but squirm, was a reward in itself.

“You love it, John. I bet you’ll come just from having my dick in your ass.”

He shook his bowed head. “No... no.”

But even as he said this, he arched his back, trying to make it easier to reach that sensitive place
inside him. His legs opened wider, allowing a bit more depth and providing a nicer view of his
stretched hole. Within seconds, semen was streaking down the door, and heavy panting replaced
his denial. His ass kept tightening and relaxing around Elliot's dick, as if wanting to pull him
deeper and coax a load out of him, and he stopped thrusting just to relish the sensation. Pressure
was building up, nearing its peak, his dick getting squeezed so hard that it bordered on painful. He
clenched his jaw to keep himself quiet, to avoid revealing how amazing it felt to be balls deep in a
man he hated.

John remained a shaking mess at the end, only held up by the force against his back. His hole was
still gripping the base, not wanting to let go, and Elliot was in no rush to leave the comfort of being
inside him. But there was one thing left to do, and he wasn't about to waste his load in the condom.
He pulled out slowly, watching the tight hole drag along his twitching dick, then released both
wrists. John collapsed to his knees, blood continuing to trickle as he clenched around nothing. It
would have been more fun to fill him up and watch the load drip out of his greedy ass. Elliot was
tempted to force his dick inside and defile him without the condom, but he managed to resist, his
gaze darting to John's messy hair. A shaky hand smoothed it down self-consciously.

“So was it everything you hoped for?”

John shot a venomous glare over his shoulder, and Elliot smirked as he slid the condom off. He
flicked it onto the back of John’s shirt, tarnishing the pristine whiteness with a red smear. Time to
finish this.

“Turn around and stay on your knees.”

As John obeyed the order, Elliot hid his surprise. He wrapped a hand around his dick and gave it a
few fast pumps—all that was needed to finish himself off. The suddenness turned John’s frown
into shock, and he flinched as spurts of semen landed on him, sparing no part of his flushed face.
Every drop was milked out while he spluttered and kept his eyes squeezed shut. Once Elliot was
done leaving his mark, he admired his handiwork and let out a breathy chuckle.

“You... fucking...” John wiped his eyelids with his sleeve before focusing his fiery gaze on Elliot.
“This doesn't change anything. You're still a loser. You'll always be a loser.”

“Yeah, well, I’m not the one with semen all over my face.”

Elliot tucked his softening dick into his jeans and then fastened them. Unfortunately it was time to
leave his beloved classmate. He pulled the door open, knocking John aside in the process, and left
without another word. His phone chimed on his way down the stairs, and he smiled again as he
checked the display.

Challenge 8 completed.
$100,000 added.

It was a shame that John’s brother hadn’t shown up, but maybe that asshole would be encountered
tonight. At least a car was still parked in the lot, and judging by the fanciness, it belonged to John.
The door wasn't locked. Even had a brown leather jacket on the passenger seat, ripe for the
picking, along with a key in the glove compartment. Elliot changed his old jacket with the new and
then revved the engine to tell John about this other conquest.

The sound drew him outside and he nearly fell down the stairs in his haste to reach the bottom. His
pants were unbelted, sliding below his hips to reveal his flopping dick, and traces of semen were
clinging to his red face. He waved frantically as Elliot backed up, but his jelly legs failed him,
unable to reach the car before it zoomed toward the road.

“You motherfucking cocksucker! Get back here!”

Elliot gave him the middle finger as he turned onto the road, tires squealing and adrenaline
coursing through his veins. This had been an amusing distraction, but he had a party to attend and
more money to earn. Only five challenges to go, and this winner was ready for them.

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