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thegainingdesk · 8 months

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The Shirt

Ollie had to admit it to himself - he kind of looked sexy. His new shirt looked and felt great and he didn't know the last time he'd felt so confident. He usually didn't go for patterns, but there was something about the cute little dancing bear motif that really charmed him.

He'd held out on buying any size large shirts, convincing himself it was a boundary he wouldn't cross, that he'd lose the small amount of chub he'd accumulated, that he wasn't nearly as big as that yet. Wearing it now, he realised how silly he'd been. Not being constrained from all angles, not having to suck in his middle all the time, not having to worry about bending down or twisting the wrong way - it was like a weight was lifted.

Looking in the mirror now, finally wearing clothes that fit, it was obvious that most of the size was in his head. What's a large, really? Nothing. Okay, he wasn't skinny, but he wasn't fat either - he'd always been naturally broad, hadn't he? He was never going to fit into mediums like his mates. He just didn't look like a kid anymore.

"Looking good man!" Geoff said, sticking his head through the door. "New shirt? We're heading off in a bit, you joining?"

"Yeah, yeah, just give me a minute," Ollie said, smoothing the front of the shirt down and taking one last look at himself. Time to upgrade the rest of his wardrobe if it's all going to look this good, he thought to himself.

"You okay?" Ollie's date Malik asked, one eyebrow raised. "You look a little uncomfortable."

"No, it's fine," Ollie said as he tugged his shirt down and tucked it in for what must have been the tenth time since he'd reached the bar. "Really, I'm fine. My shirt's just a bit stiff. Reckon I must have washed it funny. Sorry, you were saying about your course?"

"Right, okay," Malik said slowly. "Anyway, like I was saying, it's so interesting looking at all these artists all together, I just…"

Ollie struggled to listen, instead fiddling with his shirt. It strained a little in his armpit, seemed to pull at the side, the way he rolled up his sleeves seemed to cut into his arms in a way they didn't usually. He hoped he could fix whatever he'd done in the wash - he'd come to think of it as his lucky date night shirt.

Still, it wasn't all bad. It was more comfortable to have the top couple of buttons open and he found the effect of his chest hair spilling out quite sexy. He wondered idly if it really was the shirt or it might be his body - after all, he'd borrowed Geoff's dumbbells a couple of times recently. He tried to flex his pecs a little. Yeah, that was it - he was just bulking at the moment. When he got around to cutting he'd look phenomenal in this shirt.

"Fucking hell mate, what's that about?" Geoff laughed as Ollie walked up.

Ollie looked down at himself, looking for stains, only to see the familiar dancing bear pattern. "What are you talking about?" he asked.

"That shirt! It barely fits!" their mate Dan said, howling with laughter.

"Oh, right, that. It's, well I mean, it does fit," he stumbled on his words as his fingers tried to tug the bottom of the shirt towards his waistband, trying not to get too turned on by the feeling of brushing against the soft fat. "I'm just bloated at the moment, that's all. This is my best shirt, it fits perfectly."

"Fits perf… Right, gotcha," Geoff said, his shoulders shaking a little as he chuckled into his pint. "Well, I'm not being funny, but I think you've been bloated for a while now Ollie."

Ollie grinned, making a show of how little he cared. He did his best to ignore how the buttons gaped and cut into his middle as he sat down, even as he sucked his gut in. He set his pint down and flipped the menu open. "You lot eating then?"

Dan burst out laughing again. "You were bloated a second ago, what you wanting to eat for?"

"No, it's not like that," Ollie protested. "I didn't mean, bloated bloated, you know. I mean like, you know, it's just retaining water. You know, from the protein - I'm bulking," returning to his oft stated excuse whenever he was asked why he was eating so much.

Dan and Geoff exchanged a look. "Retaining water, right," Dan said, as Geoff muttered "Got to keep up the bulk."

Six pints, a burger and chips and a couple of side orders of onion rings later, Ollie struggled to suck in his gut anymore. As he walked back to their table, he did his best to hold the pints in front of the gaps in between his buttons where his belly hair was poking through. He set the pints down, exhaled as he lowered himself into his seat slowly and-

A ping rang out as the button hit Dan's pint, who fell under the table laughing. Ollie's hand flew down to his stomach, feeling the expanse of skin and hair now visible in the space opened up.

"Jesus Christ Ollie!" Geoff said, laughing. "Buy some new fucking shirts! Right, well we'll have to head home now, won't we?"

"What for?" Ollie asked. "Because it's your round next? Nah, don't worry about me, shirt's not going to fix itself by getting home any earlier, is it?" He wondered how much of a spectacle he could make of himself by the time they left. "Do you reckon they're still doing food?"

"What the fuck are you doing?"

As Ollie turned around the see Geoff stood in his now open doorway, he heard a rip and felt a breeze at his side. His hands scrambled for the two still-fastenable button on the shirt, his clumsy fingers struggling against the tension in the fabric. He inhaled, strained to shrink his swollen stomach just a touch. His fingers found some purchase, dug underneath the first button-hole, then the second, and the sides of the shirt burst open. He exhaled, and his gut hung out and down, the two halves of fabric framing his heft.

"Sorry Geoff, I was just, uhh." He looked around the room, trying to think of some plausible explanation. He hoped his gut, or at least the attention it was drawing, might hide his throbbing cock. He knew it wouldn't, especially with how tight his trousers were. "I wanted to see if this shirt still fit."

"Right, well, it doesn't," Geoff said. He looked to the side, clearly trying to spare Ollie's dignity by some small measure. "I think you'd sort of be able to tell without trying it on, to be honest."

Ollie shifted, and he tried to ignore the way his body wobbled and folded, willing his erection to stop. "I thought I'd maybe see how bad the damage was," he said with a small chuckle.

"I mean, do you really want to…" Geoff sighed. "The damage is pretty fucking bad, if you really want to know," he said, still averting his gaze. "You were smaller than me in first year, now you're… fuck Ollie, you're properly fucking fat."

Ollie nodded, reveling in the way his chins creased against each other. "I appreciate the honesty mate, really," he said. "I've uhh, started a diet," he lied. "Thought it could be an inspiration thing, you know, see if I can fit back into it at some point."

Geoff closed the door a little, shuffling out the room. "Right, well… anyway, we're going to the pub," his voice came through the door. "If you want to join."

Ollie peeled the shirt off his body, doing his best not to increase the size of the hole in the side seam. "Yeah, I'll be with you in a bit," he said, the sleeve inside out and sliding past his sausage-like arm. "You eating there, do you reckon?"

Ollie panted and strained. With one hand he gathered as much of his gut as he could, with the other he leaned past and underneath to what little remained uncovered of his dick. He squeezed his eyes shut against a wave of pleasure.

The shirt cradled his breasts like a makeshift hammock, a single button hidden in the deep crevice above his belly and below his chest. His rhythm halted for a moment as he dug one hand into a tiramisu and brought it to his mouth, cream smearing across his face. He grunted as he did his best to reach beneath himself, and he began to buck and thrust against his own hand, helping himself along.

He plunged his fingers into his mouth, counting the calories as he sucked down the last of the rich dessert, as he quivered and a sticky wetness covered his hand and filled the soft unknown beneath his quivering middle. He brought his hand up and smeared his cum against his shirt, falling back against his pillows. The motion proved too much for the tortured fabric, and it finally gave out, the button falling to the mattress and the shirt falling open around soft hairy man tits.

Ollie waddled as quickly as he could to the stall, and he smiled at the young woman manning it. He thumbed through the hangers, each shirt brushing against the furthest extent of his gut.

"I used to have this one!" he told her cheerfully, pulling one out and holding it out, looking closely at the images of little dancing bears. "I've been looking for it for years. I outgrew it ages ago, I'd sort of given up hope of replacing it."

"Oh, right," the woman said, an uncertain smile on her face. "Well maybe we'll be able to help you with that."

Ollie grinned. "Maybe - what sizes do you do?"

The woman looked Ollie up and down. "Well, you see…" She looked around, as if searching for help. "We only stock up to XL, but we can do custom orders to 3XL." The last part was added with a clear tone of hope, however vain.

"Ah, right," Ollie said. "Not sure when I last wore 3XL. A couple of years at least."

The shop assistant smiled awkwardly. Ollie knew that look well - no one knew how to respond when he talked about his weight so openly. "I'll take a 3XL anyway," he said, thinking about how hot it was to obliterate the last one.

"Do you want to try it on?" the assistant asked, happy to be back to more standard shop-floor conversation.

"Oh no, don't worry. There's no chance of it actually fitting," Ollie laughed.

"Ah, okay then," the shop assistant smiled, her confusion apparent. "For one day in the future, maybe?"

Ollie shrugged. "Sure, why not?" He paid for the shirt and left. He couldn't wait until this shirt fit as poorly as the previous one.

#the shirt #wg story #weight gain #weight gain fiction #gaining fiction #gainer fiction #gainer story #weight gain story #male weight gain #this was written quite drunk tbh #let me know if theres any typos which are too egregious

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