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The Ulterior Motive

Summary:

Dean likes to sleep around with anyone who'll spare him a glance. Gender, orientation and personality doesn't matter - he doesn't discriminate. The only problem is he's getting bored with how easy it is to coax his fellow students into bed. That's where the bet comes in.

Everyone thinks Sam is polite and well-spoken and an absolute Angel to everyone he meets. He isn't. In fact, he poured milk over Gabriel Milton's head last year when the older man tentatively asked him out, because eww. Sam doesn't do old, broke and friendless. He does, however, make bets with his brother.

If Dean can bed the University president's straight, wealthy son - Castiel - within a month, Sam has to date Gabriel until he graduates. If he can't bed Castiel, Sam gets the Impala; Dean's beloved car.

Who will win the bet?

Notes:

Chinese translation here: https://wumingxiaozu074.lofter.com/post/1eac549f_1c74a5c3b

Chapter 1

Notes:

This was borne out of a prompt from Facebook in the group 'Destiel Port'. The prompt came from JenSpinner and I tweaked it a little because I turn every Destiel fic into a joint Sabriel and Destiel story. Hope you enjoy it either way!

 

Prompt: Dean sleeps around... a lot... Boys/Girls he doesn't care.

Sam has the outward image of a polite young man, good grades, well spoken, but it's all just a cleverly planned out facade... He bets Dean that he can't bed the new headmasters son... Castiel. If Dean loses he has to give Sam his car... If Sam loses he has to give Dean his boat...

Castiel has heard rumours of the infamous Dean Winchester and is wary of him at first.. But Dean's charms begin to win Castiel over...

 

Amazing cover art is by JenSpinner (she's just so helpful and brilliant!)

Chapter Text

 

 

 

“I was particularly interested in your take on countries that have both privatised and national healthcare systems,” said Doctor Shurley with a small frown. “You compared the length and quality of life of those receiving both types of care, but in your conclusion, you implied those in the private sector are more entitled to the benefits of treatment as they have paid for it. It almost reads as though you believe that the upper class, or at least those with more money, are… more deserving of treatment than those with less funds. That… isn’t how you really feel, is it?”

Sam cocked his head to one side, eyebrows raised innocently. “I’m sorry if my conclusion didn’t read as I intended. I was merely pointing out how those with more money are more likely to receive faster and higher quality treatment, as they should because they have paid for those benefits. Those who are part of a nationalised healthcare system will be subjected to inexpensive tests and equipment, which is fair as nationalised systems are funded by the government or persons of power. They can’t afford to be spending large sums of money on national healthcare for the public when there are other places that need it.”

Doctor Shurley frowned, contemplating the answer before nodding hesitantly. “…I see. That… makes sense. Maybe alter the wording of your conclusion before you hand in your Literature Review. It reads as a little… unethical. Even though that’s obviously not what you had in mind,” he hastened to add.

Sam nodded with a small smile before making his way out of the lecture theatre and heading towards the sports department, where he knew Dean would be exiting very soon.

When he made it to the changing rooms, Dean was already waiting for him, arms folded as he glanced his brother up and down.

“What took you so long?” He grunted and Sam rolled his eyes as they began the walk to Sam’s favourite Thai restaurant. They could have made their way to the local greasy fast-food takeout for a quick meal, but that was where poor university students ate and was thus beneath both Winchesters.

“Chuck decided he didn’t like the tone of my Lit Review,” snorted Sam. “Thought it sounded like I was insinuating rich people should be entitled to better healthcare.”

Dean frowned and glanced at his brother. “Were you?”

The corner of Sam’s mouth pulled up into an ugly smirk. “Indubitably.”

Dean scrunched his nose up in confusion and Sam rolled his eyes. “It means of course I was. The idea of a national healthcare system is preposterous. If you can’t afford to pay for your own good health, then what’s the point of living? Health should be a person’s first priority; everything else is incidental. A national system encourages people to take up vices like smoking and alcoholism because they know any consequences will be paid for by someone else. That’s why countries with national systems will always be in debt.”

Dean nodded thoughtfully. “Sounds reasonable to me.”

“The problem is my lecturer is too much of a feeble-minded, pandering snowflake to see that,” scoffed Sam. “He believes our country should be more sympathetic to those who can’t afford treatment.”

Dean’s nose wrinkled in distaste. “Why?”

Sam shrugged, sliding the latest iPhone out of his Armani jeans. “The guy’s an idiot.” He tapped at his phone. “Speaking of idiots, how’s over-glorified Phys. Ed.?”

Dean rolled his eyes. “Nutrition and exercise science. Not Phys. Ed.”

“What’s the difference?” Huffed Sam just as he did every time they had this argument. “A bunch of guys run around in jock straps all day, either kicking, punching or headbutting each other until the only braincell they possess disintegrates. Then at thirty, they become sad, lonely, alcoholic drug-addicts and die of a heart attack or OD at forty. Did I forget anything?”

“Yeah. My course requires fewer sweaty guys piling into a group shower together. Also, unlike Phys. Ed., we learn that eating raw red meat as part of a protein diet doesn’t do anyone any good,” Dean said, straightening out his leather jacket.

“I could’ve told you that,” muttered Sam, eyes glued to his phone.

“Obviously, but you don’t get to spend afternoons with the cheerleaders, impressing them with not only your big brain, but also your hot body and intensive work out routine.” Dean smirked triumphantly at his brother and Sam pulled a face.

“Why would I want to waste my time with a bunch of slutty bimbos?”

Dean’s lips tugged upwards in amusement. “Why wouldn’t you want people begging you to have sex with them? I can have anyone I want, any time I want, all because I look like a jock and have the word ‘science’ tagged on at the end of my degree. And I’m pretty too. It’s so hard having it all,” he teased, looking at Sam through his dark lashes.

Sam curled his lip in disgust. “You’re such a whore,” he huffed, shoving at his brother’s shoulder as they arrived at the restaurant. Dean laughed and they stepped inside, immediately being greeted by a flustered-looking waiter. He glanced over them nervously. They’d made a complaint against him last time they visited; one more strike and he was out.

Sam eyed him in disdain. “Have you learned the difference between diet and regular coke now?”

The waiter nodded harriedly. “Yes, Sir.”

“Great,” Sam drawled. “Maybe this time you won’t try to give me diabetes.”

The waiter bowed his head slightly. “Of course not, Sir,” he mumbled. “This way. Your usual table is ready.”

They always sat in the centre of the room. They liked to watch the other tables and be in the middle of the action. Everyone had to be able to see them because they were the centrepiece of the room and their expensive clothing and good looks never failed to draw attention.

They settled into their seats, practically barking out their drink orders and smirking when the waiter scuttled away quickly.

“Who are you texting?” Asked Dean curiously.

“Ruby,” Sam murmured, refusing to lift his gaze from his phone. “She’s been pestering me for another date. Wants to go to some concert in Florida or something.”

Dean pulled a face. “You still dating that psychopath? Chick’s on drugs, I swear.”

“She definitely is. I caught her stealing opiates from the college dispensary and she begged me not to tell anyone. I said I wouldn’t so long as she broke up with Azazel and told everyone we were together instead.”

Dean cocked an eyebrow. “Isn’t that a little hypocritical of you? Thought you didn’t like junkies?”

“I don’t,” said Sam. “But she’s the hottest nurse on the unit and she’s younger than me. It’s good for my image, y’know? Plus, I hate Azazel and he genuinely liked Ruby, so watching his grades slip was fun.” Sam finally put his phone away and clasped his hands on the table as he gazed at his brother. “You bringing any whores home this weekend?”

Dean leaned back in his chair with a pinched expression. “Maybe? I dunno. I’m getting bored of cheerleaders and footballers.”

“Bring the Professor home again,” Sam shrugged and Dean grinned at the memory before shaking his head.

“Nah. She keeps worrying about getting fired and honestly, I can do without her annoying yammering. She’s getting kinda wrinkly anyway.”

“What about the art kids? They’ll probably be up for an orgy or seven. They’re all about passion and intensity, right?” Commented Sam and Dean chuckled at another memory before shaking his head.

“The sex is great but I can’t stand talking to them. They’re all a bunch of freaks.”

“What about the English students?”

Dean shuddered. “The last English major only spoke to me in iambic pentameter. I made him leave after the first hour.”

Sam snickered. His brother still didn’t know he’d paid Brady to do that.

They ordered food before speaking again.

“I heard the University President has a son,” remarked Sam, seemingly disinterested. “Mathematics. Word is he’s not bad looking.”

Dean narrowed his eyes at his brother. “…Okay…”

Sam’s lips quirked upwards ever so slightly. “Blue eyes, dark hair, fairly tall, keeps himself in shape…”

Dean sat a little straighter. He had a thing for blue eyes and his brother knew it. “I’m listening.”

Sam inspected his fork idly. “Rumour has it he’s a virgin. One of those ‘saving himself for the right person’ types. He’s already turned a few people down.” Sam eyed his brother slyly. “Supposedly straight as an arrow.”

A slow smirk crawled across Dean’s face. One of his favourite hobbies was turning ‘straight’ guys bisexual (and on one occasion, one-hundred percent gay). Bonus points for when the guys (or girls) were prudes when it came to sex and he got them begging to suck him off within a week.

“His name’s Castiel, if you’re interested,” hummed Sam and Dean licked his lips in anticipation. This guy could be his project for the next week or so.

Sam watched his brother for a moment. “He’s not going to be easy.”

“Give me two weeks,” snorted Dean. “He’ll be on his bed, ass up, screaming my name.”

“I’m telling you, this guy is going to be tough to crack. You’re going to need at least three months.”

Dean narrowed his eyes. “You willing to make a bet?”

Sam lifted his chin in interest.

“One month,” said Dean. “I bet I can get him into bed in one month.”

Sam smirked. “And if you can’t, I get the Impala.”

Dean stiffened. There wasn’t much he cared about in this world but his car was a close second to his brother. The Impala was the one thing he could rely wholeheartedly on. He could take her apart and rebuild her because he knew her body so intimately. He had so many memories of that car; she was the one place he felt free. The one place he could be himself in.

But, if Sam wanted to play dirty…

“Fine, but if I win, you have to date Gabriel Milton until you leave college.”

Sam’s eyes widened. “That’s four more years!”

Dean grinned. “Come on, Gabe’s not a bad guy,” he cackled.

Sam turned up his nose in disgust. “His major is in cooking! He’s a slob! He wears more food than what he actually presents in class. Not to mention he’s immature, annoying and a total dumb-ass. I can’t believe he actually got into college. He’s also completely broke.”

Dean chuckled. “Aww, Sammy… cut the guy some slack. He had a crush on you last year, remember?”

“He’s gross,” huffed Sam. “And he’s like… eight years older than me. He’s practically a paedophile.”

“Didn’t he ask you out last Christmas?” Grinned Dean.

Sam nodded. “As if he ever stood a chance. What was he thinking? It was so humiliating. I did put him in his place, mind you.”

“I bet it took him days to get the milk out of his clothes and hair,” laughed Dean.

“He was causing a scene; I had to shut him up somehow,” shrugged Sam.

“Well, if you want the car, you have to date him for the next month; can’t have me doing all the work,” Dean smirked. “If you win, you can dump his ass at the end of the month and I’ll give you Baby. If you lose, you continue dating him until you leave college.”

Sam scrunched his nose up in disgust but eventually relented. “And it all depends on whether you can get Castiel into bed or not?”

Dean nodded. “Do we have a deal?”

Sam regarded his brother carefully for a moment before holding his hand out.

“Deal.”