Supernatural: It's My Life (MF,anal,demon)
by The Fan

Dean Winchester sat in the car, driving on the road leading to the small town
of Plymouth, Massachusetts. In the passenger seat sat his younger brother,
Sam Winchester, a tall, good-looking young man with dark hair, dark eyes and
alabaster skin. The two young men were Hunters, part of a secret society of
people who tracked down the forces of evil and put an end to them. Vampires,
werewolves, demons, pagan gods and monsters of non-specific origin were their
prey. Dean and Sam Winchester were the sons of legendary Hunters John and
Mary Winchester. The Winchesters had been the bane of the supernatural world
for decades. They were the last two left. Hell was determined to make them
extinct but they fought back. Hard.

Lately, things had been tense between the two brothers. When a half-demon
mortally wounded Sam, Dean called upon a demon woman and made a deal to save
his brother's life. The demon woman granted Dean's wish. His brother Sam was
miraculously healed. The terms of the deal were simple. In a year, the Hounds
of Hell would come and take Dean to Hell. That's the way it was for all men
and women who made deals with the Devil.

Sam felt guilty about his brother's condition. He felt responsible. If he
hadn't been foolish enough to turn his back on a murderous half demon, his
brother wouldn't have made a life-altering deal with the Devil to save his
life. Now, though, Sam didn't feel like he understood Dean. Seriously. Dean
Winchester was living like there was no tomorrow. Mainly because there
wasn't. He was taking risks, sleeping around, drinking and partying. And
now, Sam felt like he didn't recognize Dean at all.

Dean sighed as he drove along, heading toward Plymouth, where a certain witch
had been doing some pretty bad things to the local men. Their orders were
simple. Find the witch and kill her. That's not what worried Dean. What
totally bugged him was the looks he kept getting from Sam. When was the
little bastard ever going to stop trying to rain on his parade? Dean had
always been the kind of man who accepted his lot in life and a firm opponent
of whining.

Sam was the high priest of the church of whiners and a master of guilt trips.
He wouldn't let Dean off the hook without moralizing. Ugh.

"It's my life!" Dean snapped, staring at Sam. Sam looked at him and said

He looked at his hands, then at Dean before he finally shrugged, "Cool."

Dean shook his head, and turned up the music on the radio. They were giving
his favorite song of all time. "It's My Life" by Jon Bon Jovi.

Bobbing his head up and down, Dean drove the sedan into the sleepy town of
Plymouth, Massachusetts. Once there, the brothers found themselves a hotel
and then looked for an information center. Translation? Local library,
followed by the local bar.

Later that night, they went to the cemetery to get some desperately needed
supernatural weapons. The witch they were dealing with was no ordinary witch.
She was a half-demon. Which augmented her powers. They would need knives made
out of the bones of a murdered man to kill her. And so they began to dig.
Actually, Sam began to dig. For he had lost the coin toss Dean proposed to
figure out who was doing what. While Sam dug the grave, grunting unhappily,
Dean smiled and drank his whiskey.

Dean was halfway done with the whiskey when he sensed something not far from
where he was. Ever since he sold his soul to save his brother's life, Dean
had developed a certain talent for spotting evil. Especially demons. He
scanned the environs, and finally spotted a demon.

The demon in question was a tall, good-looking young woman in her early
twenties. She had blonde hair and light brown eyes. Her pretty face wore a
permanent sarcastic expression. Her name was Ruby and she was the fallen
angel who had been helping Sam and Dean ever since they opened the Gates of
Hell and started a civil war in the supernatural realm. Ruby believed that
someday, Sam Winchester would ascend to the throne of Hell. So she sided
with the two brothers even though they were Hunters, Hell's sworn enemies.

Dean looked Ruby up and down. "Hey, bitch, how's it going?" He said.

Ruby stared at the Hunter. Sometimes, she wanted to rip his head off. He was
such an arrogant prick. However, he was the older brother of the young man
destined to become the Avatar of Lucifer, the Lord of Hell himself. She
couldn't afford to kill him...yet.

"Hey, asshole!" Ruby said with mock-cheer. "I see you're still alive."

Dean took a swig of his beer. "Um, yeah. So, what brings you along?"

Ruby put her hands on her hips. "I need to talk to Sam."

Dean grinned. "Sam's currently busy listening to music on his head phones
while digging some dead guy's grave. Can I take a message?"

Ruby rolled her eyes. "Dean, you're lucky you're cute because you're not very
bright, or funny for that matter."

Dean laughed. "Baby, are you coming on to me?"

Ruby laughed. "It would be a cold day in hell before that happened."

Dean's face looked pale. Ruby winced. Had her words hurt him? She meant it as
a joke. "Just messing with you," she added weakly.

Dean stared at her. "Do you get cold days in Hell? No, wait. Don't tell me.
I guess I'll find out soon enough."

Ruby looked at him. In that moment, he looked more vulnerable than ever, and
sexier too. She felt drawn to him. Her need surprised her. It had been a
while since she got any.

She walked up to him. "We have ways of keeping warm, you know."

Dean grinned. "Really?"

Ruby stood less than a foot away from him. She pulled him to her with
superhuman strength. "I'll show you."

Dean couldn't believe what was happening. One moment he was trading barbs
with Ruby, and the next they were romping on the grass, butt-ass naked.

Ruby undressed hastily, and unzipped his pants. "Nice body," she said. Dean
grinned. "Right back at you."

She took his pants off, then pushed him back onto the grass. She climbed on
top of him, feeling his hard cock underneath her. "Do you want me, Dean?"
She asked, looking into his eyes.

Dean smiled. "Of course." Ruby smiled, and rubbed his cock against her pussy.
With a swift thrust, he was inside her. She began riding him for all he was

Dean placed his hands on Ruby's hips as he fucked her. Hot damn she was hot.
Sexy body, big tits and a big ass, all on a slender, athletic fame. Why were
demon women so hot? "You're smoking hot, babe," He told her.

Ruby laughed. "You're pretty hot too, stud. Now shut up and fuck me."

For once, Dean happily did as he was told. He thrust his cock into Ruby's hot
snatch while wrapping his arms around her waist. Her tits flopped around his
face and he eagerly sucked on them. "Oh, yeah!" Ruby screamed. "Tear up that
pussy, Dean!"

Dean fucked her for all she was worth. Then, they switched positions. Ruby
got on all fours, then looked at him. "Dean, fuck me in the ass!"

Dean grinned, not believing his luck. "Yes, ma'am."

He spread her ass cheeks and pressed his cock against her backdoor. With a
swift thrust, he went inside. "Oh, yeah," he said. "You've got a tight ass,

Ruby spat, "Shut up and fuck me!"

Dean grabbed hold of her long blonde hair and yanked her head back while
plunging his dick deep into her ass. Ruby's asshole felt warm and tight
around his cock. He loved it. "Your ass feels so good around my dick, baby,"
he said.

"Oh, yeah?" Ruby said. "Am I as tight as some of the guys you've fucked,

Dean froze. "What the hell?" He asked. Ruby laughed, and he continued to
fuck her, his mind filled with questions. They went at it until he came,
filling her ass with his cum.

Slowly, Dean squeezed his cock out of Ruby's asshole. "Well, that was fun,"
Ruby said.

Dean readjusted his clothes, then he peddled her with questions. "What did
you mean by 'guys I've fucked'?" he asked.

Ruby shrugged. "Look, Dean. I kind of guessed that you were bisexual, okay?
It's not that big a deal."

Dean grabbed her and spun her around. "Um, well, to me it is. Keep your mouth

Ruby laughed. "Calm down, hero. It's okay to be bisexual. Really, I don't
care. To be honest, I'm kind of curious. Why do you hide it from Dean?"

Dean shrugged. "I don't need my brother knowing my business. Or the rest of
the world, for that matter."

Ruby patted his shoulder. "Cool, works for me. Gordon told me all about that
big dick of yours in Hell, so I had to find out for myself."

Dean smiled. "Gordon is in Hell?"

Ruby smirked. "Well, duh. Where do you think slain vampires go? Gordon is in
Hell. The gay bastard is some demon's bitch now. He hates you and Sam so much
it's not even funny."

Dean laughed. "Yeah, I figured he would."

Truth be told, Dean had hooked up with Gordon in secret the first time they
met. Back then, Gordon was a tall, good-looking black man who hunted vampires
for sport.

That was before Gordon was turned into a vampire by his worst enemy and
targeted the Winchesters, blaming them for his transformation. In the
aftermath, Gordon went on a rampage and was killed by Sam.

"Sam will never know the reason why Gordon hated you guys so much, will he?"
Ruby asked.

Dean laughed. "Nah, not from me."

Ruby laughed. "He's waiting for you in Hell. He's got a whole theme park

Dean shrugged. "I'll see him soon enough."

Ruby looked at Sam, who was still digging with the head phones on and hadn't
heard their non-stop fucking or the conversation that followed. "Are you
going to let him off the hook or what?" she asked.

Dean laughed. "What's the rush? I'm having fun, and he's learning to quit
bothering me with his endless moralizing."

Ruby laughed and pushed his arm gently. "Dean, you're evil."

Dean smirked at her. "Takes one to know one."

Ruby walked toward Sam. "Hey, Sammy-boy. Got a message for you."

Dean watched Ruby's sexy ass move as she walked toward his brother. Hot damn.
Demon women were certainly hot. If they were all like Ruby, he couldn't wait
to go to Hell.

The End


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