Dean's eyes widened in surprised as he saw the IT guy, Sam, walk, no waddle, into his office. Dean saw that the dude wasn't just fat, he was straight up obese! Sam's ponderous belly jiggled profusely with each step. Sam's white button down, which already had to be 2XL or 3XL, didn't even seem to fit properly, as it appeared as though a button were missing, with peach colored fat flesh bulging through this big gap, not to mention all the other gaps between the buttons, which appeared to be hanging on for dear life.
As far as Dean was aware, there were only a few possibilities here, either Sam didn't have a good tailor, this was the biggest shirt he could find, or his already apparently huge weight was on the rise. Dean was quite sure it was the last one. Either way, the poorly-fitting shirt and Sam's massive physique wasn't leaving a good impression with Dean, who thought, "I might have to chew Kevin out after this."
Dean realized that he was staring though, and was glad that Sam broke the ice, saying, "You must be Dean! Where's the problem at?" in a jolly disarming voice, extending out his hand, giving Dean a firm handshake. Sam acted aloof, as though he didn't see Dean staring, but he definitely knew, and was used to these stares from people who didn't know him. Little did Dean know that Sam was staring at his cut, muscular body.
Dean tried his best not to scoff or scowl, but Sam could still see a little bit of a scowl on Dean's face as Dean showed him to the computer. Dean explained what was going wrong, and he winced a little as Sam sat on his chair, which groaned in protest, but the luxury chair could hold Sam's weight just fine.
Dean's eyes widened in surprise and awe as a flurry of folders and tabs were opened in rapid succession. Sam even brought out the command prompt, installing a few files with fast keystrokes and rearranging them as necessary. Dean paced over to the window to look back over the city, trying his best to mentally de-stress, and to be fair, Dean's impression of Sam was already improving from watching him work.
As Dean was staring at a window washer, getting lost in his own thoughts, he was surprised when he heard Sam cheerily say, "Try it out, sir!" and much to his delight, Dean was able to keep working on his report! On top of that, his computer had been slowing down lately, but now it was as fast as it was new! Dean got back up and shook Sam's hand again, saying, "Impressive! I might just make you my go-to IT guy!" and Sam smiled brightly saying, "I'd be happy to help again!"
Sam made to turn around, but he stopped himself. Dean said, "What's wrong, Sam?" and Sam looked Dean over again and this time, Dean noticed. Dean said, "I like you Sam. You do good work and you're able to keep your head held high despite well... everything." Dean was trying to refer to Sam's weight, and Sam realized the same thing, trying not to roll his eyes.
Dean continued, saying, "If you're interested, I'd love to show you around the gym, maybe show you some good workouts!" He was trying his best to not be disparaging about Sam's weight. Sam squinted his eyes in thought, then said, "Ok, sure, as long as you're willing to have a good meal with me!" and Dean cocked his head curiously, not quite sure what Sam meant by that, but given how fat Sam was, Dean was sure he had good taste in food, so he was willing to go along saying, "Sounds like a deal!" and the two started exchanging phone numbers.
Now that Sam had proven himself to Dean, and had proven to be a nice guy to boot, Dean wanted to help Sam. He was now giving Sam the benefit of the doubt instead of judging him, figuring Sam must either be depressed or perhaps have an addition problem that was leading to his weight gain. Dean thought that he could start to fix Sam and help him lose weight. Heck, maybe they could even end up as gym buddies!
Sam, on the other hand, was on the exact opposite page. Sam's weight wasn't the result of him losing control or eating his feelings; he loved being fat! It was something he wanted for himself, and he was quite secure about his weight. He, on the other hand, saw Dean as someone who was putting on a front. Dean seemed like a workaholic, and he was sure that Dean was only maintaining his excellent physique to impress people. He wondered, deep down, what kind of lifestyle Dean would have if he didn't worry about being judged. Sam had no way of knowing yet, but he thought it would be fun to see if he could nudge Dean in the direction of gaining weight, and see how big Dean would get. Maybe Dean would discover his inner glutton, or at the very least have his ego broken a little bit.
The two had their own ulterior motives for wanting to hang out together, and only time would tell which one of them would be able to influence the other.
...
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