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The Proposition

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In Dean’s defense, he didn’t mean to lie to her. It’s not like he woke up that morning and concocted an elaborate plan to deceive his mother or anything. It’s just that, well, Ellen Smith could be a formidable woman, even just over the phone. So when she started chiding him (again) for spending too much time on his job and not enough time on his personal life, he panicked and might have just told her that she didn’t need to worry about him because he was in a perfectly happy romantic relationship, thank you very much.


Which brought Dean to his current predicament.


“A boyfriend?,” Ellen exclaimed, surprised but pleased. “Since when?”


“Uhhh, let’s see...,” Dean drummed his fingers on his desk and tried to get his story straight. “I guess it’s been around four months, maybe? Yeah, that sounds about right.”


“And where did you meet this mystery man?”


“Where did I meet him? We Here at work, I mean.”


“An office romance? How scandalous,” Ellen teased. “What’s he like?”


And that...was actually a very good question. What was his non-existent boyfriend like?


Right as Dean’s mind screeched to a halt, a familiar figure walked by to chat with someone right outside his office and Dean was greeted by the leggy form of the cute IT guy, Sam Wesson, that he’d spoken to a few times before.


“He’s...tall,” Dean blurted out before he could stop himself. “Really tall.”


“He’s tall? Gee, you’re really painting me a picture of this guy. C’mon Dean, give me something to work with here,” Ellen prodded.


“Well, let’s see...he’s smart. And handsome. And uh,” he looked around his office for some sort of inspiration, and his eyes were once again drawn to Sam standing outside of his office, his head thrown back in laughter at whatever someone just told him. “He has a great laugh and gets these dimples whenever he smiles that drive me crazy. He has long hair that should look goofy but suits him really well, and he has the most beautiful eyes I’ve ever seen.”


Okay, maybe he was babbling there at the end. And maybe he should stop describing the IT guy that wasn’t actually his boyfriend. 


“He sounds lovely, Dean. And what was his name, again?”


“His name?”


Don’t say Sam, don’t say Sam, he thought to himself frantically.


“It’s...Sam. Sam Wesson. Yep, that’s him. We’re totally in love. With each other.”




“Well, I’m happy for you, Dean. How about you bring Sam with you tomorrow when we have dinner together? I’d love to meet him,” Ellen said warmly.


Obviously, Dean couldn’t let that happen. He needed to tell his mom that Sam was too busy tomorrow to make it to dinner. Maybe Sam had a doctor’s appointment. Or he was visiting his sick grandmother in the hospital. Or he was taking hula hooping lessons; it didn’t matter what he said, really, just as long as he managed to make up something.


“Sure, mom,” he said instead as his mouth moved without his permission. “We’ll both definitely be there; I’m sure he’d love to meet you too.”




After that disaster, he finally managed to end the conversation a couple of minutes later before he could dig himself into even deeper trouble by continuing to lie and convincing his mom that he and Sam were engaged or something. After he wearily hung up the phone, he took a few minutes to contemplate just how screwed he was. He also briefly wondered if it would be considered sexual harassment if he were to ask his subordinate to pretend to date him and eventually decided that, yes, it probably was


But he also didn’t really have any other options aside from posting an incredibly specific ad on Craigslist and praying that he didn’t wind up in a ditch by the end of the night, so he decided to go ahead and just roll the dice by begging Sam to be his fake boyfriend for one night.


It probably sounded less weird out loud than in his head, right?




Sam’s brow furrowed in confusion. “You want me to be your what?!”


Okay, maybe it wasn’t less weird said out loud. If anything, it was probably weirder.


“It would just be for one night, I promise!,” Dean reassured as he checked for the millionth time that his office door was closed and that no one could overhear him proposition one of his employees. “...please don’t sue me.”


Sam bit his lip and looked like he was deep in thought. “And what would I get out of this, exactly?” he asked finally.


Dean’s shoulders slumped in relief. This might just work after all.


“How does $200 sound?,” he offered hopefully.


“...okay, fine. Deal.”




“Sure, why not?,” Sam shrugged. “It’s a free meal, and I could use the extra money. If you want sex out of it, that’ll cost you extra though.”


“What?!,” Dean sputtered as his face turned red. “I didn’t-- I wouldn’t--”


A huge smile split Sam’s face and Dean could distinctly see the dimples that he raved to his mother about earlier. They really did drive him crazy.


“Relax, man. I was just screwing with you.”


“Real funny,” Dean said dryly. “Look, I’ve gotta get back to work but just show up here tomorrow with a change of nice clothes, and I’ll fill you in on the details of our ‘relationship’ on the way to the restaurant. All you have to do  is pretend to be into me and charm my mother. She can be intimidating, but I think she’s kind of desperate for me to have a love life, so she might take pity on you.”


“Got it,” Sam said as he made his way towards the office door. “I’ll be the best boyfriend you’ve ever had, sweetheart.”


“Get out.”


And with a jaunty salute and a wink, Sam was out the door and Dean dropped his head against his desk.


All he had to do was make it through tomorrow and he’d be home free.



The following day passed too quickly, and it seemed like no time at all had passed when he was suddenly driving to the restaurant with Sam scrunched up in the passenger seat of his Prius as he briefed him on what his mother knew about their supposed relationship.


“So what exactly is the end game here?,” he asked when Dean fell silent. “Are you just gonna wait a few weeks after tonight and tell your mom that we broke up or...?”


“I haven’t really thought about it,” Dean admitted. “But, yeah, probably. It would probably be a little too much to ask if I kept dragging you around as my fake boyfriend.”


“I don’t know,” Sam responded, pretending to contemplate the idea. “That sounds like a pretty lucrative proposition to me.”


Dean rolled his eyes and snorted as he pulled in the restaurant parking lot.


“Great, you’re not even my actual boyfriend and you’re still a gold digger,” he muttered.


“I can’t help it if I like nice things,” Sam said cheekily while he got out of the passenger seat.


As he unfolded his long legs and stepped out of the car to stretch, Dean took the opportunity to admire him. He usually only got to see Sam in a goofy polo shirt and khakis, and while he managed to appear sexy even in that outfit, he looked amazing tonight in a burgundy sweater that clung to him in all the right places and a pair of dark jeans that made his ass look incredible. Dean had no interest in sporting a boner while eating dinner with his mother, however, so he tore his eyes away from Sam’s body with great reluctance and gentlemanly held the restaurant door open for Sam.


When they finally sat down with his mom, the dinner went a lot more smoothly than he thought it would. He had been afraid the entire time that everything would come crashing down somehow, and he’d be stuck with his mother giving him that disappointed look that always made him feel like the worst person in the world. Surprisingly though, Sam wasn’t lying the day before when he said that he’d be the best boyfriend that Dean ever had. He was witty, polite, and his story about taking a tractor for a joyride with his brother while being chased down by a half naked farmer made his mom laugh harder than Dean had ever seen before. He could tell that his mom genuinely liked Sam, too, which surprised him because she typically took a bit longer to warm up to people.


The fact that his plan was working so well should have made him happy, but to be honest, Dean was mostly just starting to regret that Sam wasn’t actually his boyfriend. Before he could sulk for too long, his mother’s voice jarred him back to reality.


“Out of curiosity, how did you two start dating? I know that you met at work, but Dean never told me how your relationship got started.”


Shit. Dean probably should have come up with something for that, and he desperately tried to think of something plausible. But before he could spin a tale, Sam’s hand reached for his own and laced their fingers together. Dean looked at him in surprise, and he could feel his heart beat a little faster as he decided that he liked the way Sam’s hand looked when it was intertwined with his.


“It’s kind of a funny story, ma’am,” Sam began. “I’d been working in the IT department for months and always had a bit of a crush on Dean but never really had a chance to talk to him until one day he called me up to his office to fix his computer. Except I knew that if I completely solved the problem, then I might not get another chance to see him. I made sure that there was still a little something wrong with it because I hoped that he might call me back up again the next day.”


“Did he?,” Ellen asked.


Sam grinned widely. “I managed to keep ‘overlooking’ problems with the computer and ended up being sent to his office every day that week to fix something different. By the end of the week, I think he cottoned on that I had a crush on him, and he finally asked me out. I think Dean probably told you the rest.”


Ellen smiled at Sam and patted their clasped hands. “Well now, isn’t that a sweet story?”


Dean had to agree with her, and he would have been impressed with Sam’s ability to quickly think of a lie if not for the fact that it wasn’t actually a lie at all. Sam really did come to his office every day for a week a while back in order to fix his computer. The only thing that wasn’t true, obviously, was the part where Dean asked him on a date at the end of the week, but he was kind of starting to wish that he had.



About an hour later, Dean and Sam bid his mother farewell and Dean drove Sam to his apartment, but before Sam could get out of the car, Dean turned to him.


“Were you really trying to flirt with me that time it took you an entire week to fix my computer?,” he asked curiously.


“Well...yeah,” Sam replied. “Why else wouldn’t I have just fixed your computer when I was up there the first time?”


“To be honest, I kind of just thought you were bad at your job,” Dean admitted. “But I kept you around anyway because I liked the way you looked when you bent over my desk to look at the computer.”


Rather than respond, Sam leaned over his seat and pulled Dean into a kiss that eventually turned into the kind of make-out session that Dean hadn’t experienced since he was a teenager; the kind that left him hard in his pants and aching for more.


“You know,” Sam said when they finally disentangled, his lips shiny with spit and bitten red, “you could come upstairs with me and bend me over something else if you want.”


“I don’t know...would it still cost me extra?,” Dean joked.


Sam tapped his chin and feigned being deep in thought.


“I guess I could give you a freebie. Just this once.”