The Offices of Hale & Hale - Round 2 - Derek
- by @chubby-derek-and-friends
Derek Hale frowned as he looked into his mostly empty closet. The amount of clothing he had to wear was drastically less than it had been at this time last year, the cedar-lined room practically bare. Only a week previous, Derek has begun his spring cleaning, taking out any pants or shirts that couldn’t be buttoned. The pile had been…bigger than Derek would like to think about.
Thanks to his tailor, and monthly standing appointments, Derek at least had clothes for the office, and his standard basketball shorts and tank top undershirts were always good for lounging around his loft apartment (even though they had been sized up at least once in the last year), and for workouts (which had been whittled down from a strict 6-days a week to 2-3). But as Derek stared at the clothes he had hanging in his closet, he was faced with the fact that he did not in fact have anything that would be appropriate for his company’s Memorial Day Picnic.
Wandering around a crowded mall the Sunday before Memorial Day was not exactly Derek’s idea of relaxing outing. In fact, Derek hated shopping, and he really hated malls. Malls were loud and full of people and while Derek had no trouble with his colleagues in the office, or even a board meeting full of people staring at him (okay, that may still have made his stomach squirm), Derek was definitely not a social butterfly.
In the office, there was an easy social structure to most interactions. And even though Derek preferred that his employees call him by his first name rather than, “Mr. Hale,” there was still an easy-to-navigate blueprint Derek could follow for most of his daily conversations. Well, with everyone except Stiles.
It had been almost a year since that very first elevator ride with Stiles on his first day as Hale & Hale’s Happiness Producer, and what did Derek have to show for it? Fifty extra pounds gained and a complete inability to talk to a man he fantasized about. Normally, Derek had no problem addressing and employee, but for whatever reason, he always seemed to become tongue-tied around Stiles. Or worse, he would blurt out something that would seem like the lewdest innuendo. Derek was just thankful that Stiles seemed to take them as jokes. He never seemed uncomfortable and continued to show up with lunch for Derek almost daily. That was probably where most of his weight gain had come from.
Derek rubbed his stomach as he weaved through the crowds, feeling the plush belly currently contained in a button-up shirt. The warm cinnamon smell of freshly baked goodies distracted him for a moment, and Derek almost found himself making a detour to the food court, but he managed to stop himself, returning to his mission. Okay…maybe it wasn’t all Stiles’s fault, but Stiles was also damn good at his job. Too damn good.
Derek huffed out a sigh as he dodged a gaggle of teenagers and headed into American Eagle, doing his best to push thoughts of Stiles from his mind, lest they make the venture even more awkward than it was shaping up to be. He quickly made his way to the shorts and began browsing.
The worst part of this entire venture was that Derek didn’t really know what size he needed to buy. With his pants being tailor made and his basketball shorts a stretchy-waisted “large”, he didn’t really have any way of figuring out what to buy, short of calling his tailor to get his measurements, the idea of which made him more uncomfortable than the prospect before him: grabbing a couple of pairs of shorts and trying them on in a dressing room.
“Can I help you find anything?” A voice asked from behind.
Derek frowned and turned to find a pixie-like girl smiling brightly up at him. “Uh, shorts.” He grunted out.
“Of course! Do you know what style you want?” The girl asked, moving around him to the racks.
Derek looked at her blankly.
The girl continued, unperturbed. “We’ve got slim fit, classic, cargo, jean shorts, or ‘jorts,” the girl giggled.
Derek didn’t laugh, not really understanding.
The girl’s smile started to fade a little, and Derek began to sense that he was really messing up the interaction. He turned back to the rack in front of him, and pawed through the hangers. “Uh, I’m going to a company picnic tomorrow and I needed something casual enough for a picnic, but still nice looking.”
The girl’s smile widened at Derek’s participation. “Got it! Well then I would steer away from jean shorts and cargos. Both are a little too relaxed. You’re gonna want to stick to the cleaner look of either the classic or the slim fit.”
Derek snorted at the idea of him wearing anything considered “slim fit” at his current size, then frowned when he realized the girl looked unhappy again. “Sorry, was thinking to myself. I think the classic would be best. “
“Classic it is! Do you know what shade you want?” The girl said.
Here Derek blushed. “I…um…I don’t know.”
“Oh! Well we can measure you if you need? Or we can check your pants’ tag…”
“These are made by my tailor. They don’t have a size.” Derek felt like an elitist asshole for a second. “I…um…I know I used to wear a 32 in college, but I’m not quite as…fit…as I used to be. So, maybe 36?”
The girl nodded, playing off Derek’s comments. “Okay! If you want, we can get a couple different sizes so you can see what’s comfortable. Every pant is cut differently and if you’re used to wearing tailored clothes, it might not feel right immediately. The 38’s are the largest we have in-store but we can also order larger sizes online.”
Derek nodded, feeling sure that he wouldn’t have to go that far, and watched as the girl began to pull khaki shorts off the rack, gathering sizes from 34 to 38. Derek felt a blush at the larger size being added to the armful she had, and wanted to say something, but then stopped himself. She was right, maybe the shorts would fit differently. What did it hurt? Aside from his pride.
Derek followed the sales girl to the dressing rooms. The loud music that played through the store seemed even louder back here and Derek couldn’t help but wince. God, was he becoming an old man? The thought made him frown as the girl opened a room and hung the shorts on a hook inside for him.
“Here you go! I’ll be back to check on you in a little bit, okay?” She smiled at him, before hopping off back to the sales floor.
Derek quickly dodged into the closet and pulled the door shut. He both hated and loved someone else knowing how much he had let himself go. It was erotic, but also embarrassing. Taking a couple of deep breaths, he looked into the mirror and tried to calm himself down. The urge to flee was almost overwhelming but Derek used all his self-control to center himself and override those feelings.
“Come on,” he told himself sternly as he picked up the first pair of shorts, “you’re already here. Just figure out which shorts fit and then you can get out of here.”
Maybe get some Cinnabon on the way out, his mind answered him.
Derek frowned at the thought and quickly pulled off his pants. He never used to be that into sweets before Stiles started working at the office. Or...rather, he never used to allow himself to eat that many. He’d been a jock in high school and college, so watching his diet had been second nature. Now though...now he craved them. And he loved seeing them pop up on his desk, especially when Stiles was the one to drop them off. It felt...almost...like a personal gift from him, which just made their decadence all the sweeter.
Derek grunted as he pulled up the first pair of shorts. The stiff material hugged Derek’s thighs and he had barely pulled the shorts’ waistband up to his ass. These were definitely too tight. With not a small amount of trepidation, Derek worked the shorts back down his legs and picked them up to face level to check the size. 34’s.
Derek sighed with relief. He hadn’t expected these to fit anyways. Though how tight they were didn’t exactly give him hope for the other sizes. Folding the current pair in half, Derek set them aside and picked up the next ones. 36’s. He checked before he started pulling them on.
God, 36’s. Derek had never imagined that he would need to size up like this when he was younger. He never imagined himself other than the trim athlete he had been in his youth, but running a major corporation had a way of changing things. And Stiles’ additions to his diet certainly weren’t helping things. And this was just after a year with him on the team. What would the future Derek look like? The idea was both frightening and incredibly arousing.
Derek huffed slightly as he pulled the shorts up over his ass. The fabric was skin-tight around his thighs again, although he had at least gotten the waistband up over his butt. Or so he thought. Derek turned sideways to find that his reflection showed the shorts had actually stopped short of completely covering him in the back, leaving a couple of inches of underwear-clad booty in plain view. And he still hadn’t even tried to button the shorts. Derek looked down at the last pair and swallowed, suddenly very nervous. This was the largest size they had in store.
Pushing down the 36’s, Derek silently cursed every snack and fat-filled meal he’d eaten since Stiles started working at Hale & Hale. He tossed the rejected pair on top of the 34’s and picked up the 38’s, holding them out in front of him to gage their size. They looked wide in his hands, but then again, so did his pants recently. Derek took a deep breath and started putting on the shorts. He managed to pull them up over his butt completely, though there was very little wiggle room, and the fabric still pulled at his thighs and crotch, but Derek was determined to make do. He tugged the shorts closed, struggling to get the button to slide into the hole. He fought for a moment, but the fabric wouldn’t budge, and he felt like his thumbs were more hindrance than help. With a grunt, he relaxed, letting the shorts gap back open. His rounded belly pooched out over the shorts.
Determined, Derek sucked in a deep breath, pulling his stomach in with it, and again pulled the two sides of the shorts together. His face got redder and redder as he struggled to get the button through the hole. After a minute of fighting with it, Derek felt the fastener slip into place, and he sighed out a heavy breath. His stomach rolled forward, high and proud. The waistband pinched uncomfortable in the front, and the legs and crotch pulled from the back as his ass stressed the rear seam. He looked at his reflection in the fitting room mirror, noticing how much bigger his belly looked with the tight shorts cinching it up. His love handles looked wider too, lopping over the sides. If anything, the shorts just made him look fatter.
Derek slid his hands up over the rounded, heavy globe of his belly. The light fur train the led from his belly button continued downwards, but the rest of his belly was only slightly furred. The skin was sensitive, crisscrossed with tiny stretch marks that had grown with Derek’s appetite. The sensation of tracing them sent a shiver up his spine like it always did.
Placing a hand below the protuberance of his gut, Derek hefted it slightly, feeling both the weight and the softness. Had it only been a year ago that he had a visibly 8-pack? God, what was happening to him?
All that playing with his belly was having a profound effect on Derek’s dick. He could feel the erection building as he shifted his hands around and pressed in and around on the soft, jiggly mound. What would Stiles say if he saw him like this? Would he be into it? Or would he only be interested in the slim, fit man Derek used to be? His dedication to feeding Derek certainly seemed to lean more towards the prior, but who was to say?
Derek’s stomach growled loudly, and Derek was suddenly struck with how hungry he was. Hoping to be finished, Derek reached below his belly and began trying to pull up the zipper, but it wouldn’t move. He grunted and groaned and tried again and again, but the zipper stayed stubbornly unzipped, and Derek was forced to finally admit defeat. Derek’s shoulders slouched. He was still short-less.
A knock at the fitting room door startled him and caused him to jump.
“Everything alright in there?” asked the voice of the girl who had been helping Derek before.
Derek looked down at the gapping fly on the shorts, then at the pooch of his belly.
“Uh...not really.” he said.
“Are those sizes not working out for you?” she asked.
Derek flushed, feeling embarrassed that his inability to fit into the largest pair the store sold was basically being broadcast to the other shoppers. “...No.”
There was a slap of fabric and buttons as a pair of khaki shorts was thrown over the door. “I found a pair in our stock room that someone ordered and then returned. They’re a size up from the once I gave you. Do you want to try them on?”
Derek seized the shorts like a lifeline, tugging them over the door. “Uh, yeah. Thanks,” he grunted.
“You’re welcome!” the girl called chipperly.
Derek held up and looked at the shorts, checking the tag. 40”. Jesus, was this who he was now?
Fumbling with the button at his waist, Derek undid the 38’s and pushed them down his legs. The fabric peeled off like lycra, and he wondered why he thought he was going to get them to fit as he pushed them the rest of the way off with his feet. He picked up the shorts and threw them on the stack of the other rejects, not even bothering to try and fold them.
Finally, he unfolded the 40’s and put his feet into the leg holes. He slid them up his legs where they tautly, but not tightly, fit around his butt. The button at the waist still took a little bit of finagling to get to close, but when he had the shorts buttoned and the zipper zipped, he found that the shorts were already 10 times more comfortable than the last pair, even if they did pull a little bit.
Derek looked at himself in the mirror. Sure, his stomach still pooched out over the waistband, but they weren’t ridiculously tight like the others, and they didn’t give him a crazy muffin-top. He could wear these to the picnic. Then after Monday, maybe he could look into getting back into shape.
Derek turned and checkout out his butt in the shorts, noting how they hugged the curve in a visually appealing way. Okay, so his shape wasn’t that bad.
Now that he had a pair of shorts that fit, Derek felt relieved. It only took a few minutes for Derek to take off the shorts and put his pants back on, then head to the register with the 40’s on his arm. Checkout was pretty painless as well. No one commented on the shorts’ size. Before he knew it, Derek was walking out of the clothing store with his purchase and a smile on his face. A smile that carried him straight to the food court where he promptly bought a half-dozen Cinnabon. His diet didn’t start until Tuesday, right? Besides, he deserved a reward for dealing with the crowds at the mall.
Monday dawned bright and clear, no hint of cloud or threat of rain, which was a good thing, as Derek knew Stiles had put a lot into the outdoor event. The successful shopping trip had left Derek feeling a little better about his prospects of talking to Stiles. Sure, his waist was definitely larger than he had thought, but the more Derek looked at himself in the mirror, the more he liked his “curves.” He liked the feeling of power that his size gave him, liked how broad and intimidating he looked. He also liked how his body felt; how sensitive his belly and his chest were; how his body moved when he walked.
He had worked out in his building’s gym on Sunday and the definite bounce his chub gave every time he made a circuit on the elliptical machine left him feeling more keyed up at the end of the workout then he’d ever been before. He’d had to cut his weight routine short for fear of revealing just how much his body excited him. It was a new feeling, and one Derek wasn’t exactly sure what to do with, but he was willing to go with it.
When he was dressed in his new shorts and a short-sleeve button down shirt, Derek found that he felt more confident. The way the plaid fabric of his shirt hugged his rounded gut and love handles was satisfying to his eye the way a tapered shirt used to be on his trimmer frame. And with his new-found confidence, Derek was hopeful that Stiles just might, MIGHT, reciprocate his feelings.
Derek took one last deep breath, and headed out the door.
Walking up to the park where the Annual Hale Memorial Day Picnic was being held, Derek couldn't help but smile. The park was full of Stiles’s little touches, from the giant picnic blanket, to the towering chocolate fountain, to the inflatable obstacle course. It reminded him of coming to picnics with his family when he was younger, a thought that brought up bittersweet memories of his parents mingling seamlessly with both investors and employees, his siblings playing sports and games on the open grass fields with the other employees’ children, the music and food and fun all around him. It was a little overwhelming, and Derek was the only one to arrive yet.
Well, not the only one. Out among the decorations and seating areas, Derek could see Stiles giving instructions and orchestrating the chaos as last-minute set-up was done, food was delivered and set out, and final preparations were made. Stiles was the man that had brought back the feeling of Derek’s parent’s company, and Derek needed to tell him how he felt.
Striding bravely up to the man’s back, Derek tried to think of what he could say, how he could convey what he was feeling. All too soon he was right behind Stiles. Just as he opened his mouth to speak, Stiles turned around.
“Hey Scott...” the man greeted, then stopped, his face morphing from a nervous smile to a look of surprise. “You’re not Scott...”
“This is so perfect, Stiles,” Derek said, “You’re wonderful!”
Stiles immediately blushed, which Derek can’t help but find adorable. “Oh, uh, thanks, Derek. I mean...I’m just doing my job.”
Derek was about to reply when Stiles’s phone goes off.
“Uh, sorry, I need answer this,” Stiles said, putting the phone to his ear and stepping off to the side. “Hey.”
Derek stood there waiting. He does his best not to eavesdrop, but Stiles is right there.
“Yeah, today is the picnic. No, I knew you wouldn’t be able to make it, it’s okay. I still want you to meet everybody eventually. Yeah, that’s fine. I’ll be home around ten or so. You don’t have to wait up for me. Okay, well, I’ll see you tonight then. Okay, love you.”
Derek felt his stomach dropping more and more with each sentence. Did Stiles have a significant other? Why hadn’t Derek heard about it? Obviously they were serious enough if Stiles wanted them to meet all his coworkers. God, no wonder Stiles seemed put-off by Derek’s comment.
Before Stiles could turn back around, Derek had quickly moved away. He had made a beeline for the giant chocolate fountain, and was using it to block himself from Stiles’s view.
God, Derek was such an idiot. Of course someone like Stiles would already have someone. People like Stiles didn’t wait around for guys like Derek to come to them. He probably met someone thin and happy and talkative who liked going out and didn’t spend all his time working.
Derek looked at the piles of fruit and sponge cake skewers that were set up next to the chocolate fountain. Maybe Derek wouldn’t make a fool out of himself again if he kept his mouth full.
