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BHM Winning over her boss (BHM SWG, encouragement)

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Well-Known Member
May 12, 2007
Jack settled back at his desk. That had been a nice lunch he reflected, another great lunch with his great team. He ignored the pressure of his waistband against his stuffed belly and opened a spreadsheet. He looked at it, his enthusiasm for working quickly shifting from low to non-existent. He tugged at his belt, shifting the pressure on his belly enough for a small burp to escape without warning. He glanced around quickly. Luckily no one else in the open plan office had noticed. He tried to focus on the spreadsheet but found his eyes drawing shut, despite his attempts to fight off sleep.

He snapped awake when a hand landed on his belly and pinched the roll of flab that had appeared there over the last couple of months. “Enjoyed lunch?” whispered Jess and then showed him a file, asking for guidance, though they both knew she had the answer already. Which was a good thing as her intrusion had him well and truly discomfited. What did she mean by grabbing his gut like that? Why did he even have a roll to pinch? Before turning back to her desk, Jess again managed to brush his belly, her eyes teasing him.

Jess was one of the young stars on Jack’s team, intelligent and a quick worker. She had only joined the team six months ago but was already its life and soul. Her bubbly character, sexy figure and pretty face ensured that she always had a very quick response from other teams, even legal and compliance who were notoriously known as the anti-business department. She had a huge appetite and worked very hard to keep herself trim with a variety of workouts at the gym, including aerobics and spinning classes. Nonetheless, she was always the first to help herself to goodies brought in for a birthday or other occasions. She was a known foodee and was always exchanging recipes and could discuss food, and the best places to find it for hours on end.

If Jack were to be completely honest with himself, he would admit that he was smitten by Jess and her fun attitude to life. If he was even more honest, he would also have to admit that he had hired her almost exclusively based on those factors: luckily she was actually good at the job and had won general approval. One of the changes she had instilled was the idea of a team lunch. Whereas before she joined they all used to do their own thing, she quickly organised lunch out at a restaurant almost every day. Of course not everyone could join each day, but of the group of fifteen, they were usually around five who could make it.

Jess also encouraged them all to eat plentifully, so lunch was never a quick bagel but a proper meal, often including either starter or dessert; sometimes both. She discovered restaurants that no-one knew of before, that either offered a set menu at a good discount, or could be persuaded to do so. In Jack she found a latent foodee: while he was by nature a glutton, he suppressed this under pressure from his girlfriend of three years, Olivia.

Jess had met her at a work do some weeks earlier and immediately found her polar opposite. Olivia worked in an attorney’s office and was every inch the advocate bitch from hell. While this earned her plaudits in the courtroom, unfortunately she carried the attitude like a shield around her. As soon as Jess saw her, she realised that Olivia was an uptight cold fish: she took life far too seriously and her career was clearly her priority. She also worked out very often, but unlike Jess who did it grudgingly in order to offset her appetite, Olivia did it because it was the done thing. She ate ascetically, ignoring the finger foods on offer and instead picking at the lettuce and tomatoes which were really only there as garnishes. While Jess was slender she had curves in the right places, but Olivia’s body was as flat as an ironing board.

Jess couldn’t understand how fun-loving egregious Jack had ended up with such a soulless cow but put it down as another of life’s mysteries. That was until she noticed one small incident. Olivia’s phone rang and she took a call from her boss, moving over to one side for privacy. At that point Jack turned away from a conversation and collided with a waiter, resulting in the two of them falling to the floor. The waiter got up quickly but Jack remained lying down, rubbing his ankle, clearly in pain, and groaned softly. He looked around and saw Olivia looking straight at him. She rolled her eyes and pointed to the phone, shrugging her shoulders. By the time she hung up Jack was seated with an ice pack round his ankle, surrounded by a bunch of friends, wishing him well and taking the piss in equal measures. Olivia's only comment to Jack: “How clumsy you are, did you knock over the waiter?”

As they drove home in Olivia's BMW 3 series, 'the' car for an attorney at her level, Jack sat back in the passenger seat and rested is leg. “That fall hurt more than I thought” he said.
“Oh you're so clumsy Jack, you really should be more careful” she replied. Olivia looked at him and her face, already dismal, turned into a scowl. “What's this then?” she demanded sharply, digging a finger into his slight belly bulge. “You're eating far too much Jack, you need to watch out. I don’t know why you always have to pig out so much!”
“I don’t pig out” he lied.
“Yes you do, that’s why you always return from our holidays a few pounds heavier than when leave. I on the other hand take care and do not get fat” she boasted.
“OK, so I enjoy the local culture and cuisine, that’s half the fun of the holiday!” he retorted. “In any case, I always lose the weight don’t I?” He continued in a mutter: “you bloody well make sure of that.”
“Huh?” she gasped. “Gee say thanks for my looking out for you, I’m just helping you to avoid blimping up!”
“Blimping up?!” he exclaimed. “For fuck’s sake I only ever gained 7 pounds max and that was on a two week vacation in Florida and Miami, you know if I really ate like I wanted to there I’d have doubled my weight!”

“Oh that’s really something to be proud of!” she snorted. “And how much have you packed on now, you never really lost the weight from France did you, and that’s been what, two or three months? When’s the last time you hit the gym?” she added, poking his gut again.
“Oh about 2 weeks ago, you know I had a cold and couldn’t breathe properly” he protested.
“Sure, and now with your ankle hurt through your sheer stupidity that’s excuse enough to take another couple of weeks off, to make sure you get good and fat!” she retorted.
“Oh stop exaggerating!” he ended the argument there.

Still, later that evening as he stripped for bed he looked in the mirror. He couldn’t deny that there was a softness to his belly that had not always been there. It was true that he had gained some 5 pounds in France, but that came on top of another 5 gained at his mum’s during July. Each pound was barely noticeable, but altogether they gave his usually flat stomach an inflated look, bulging out over his boxers. Whoa that was new! Since returning from France he had lost a couple of pounds he knew that. Then again, the routine of team lunches almost every day over the past months coupled with less exercise than usual was starting to take its toll. He decided to step on their scale to check his current position.

The needle swung up and down then rested at 175 lbs. Jack inhaled sharply, that couldn’t be right. His fighting weight was 160. He sat slowly on the loo and did some metal maths. So before going to his mum in July he was at 160. No hang on, he hadn’t quite managed to reach 160, he was more like 162. OK then added another 5 at Mum’s, so up to 167. He had only managed to lose 2 before going to France where he gained another 5, taking him up to 170. Since then he had hit the gym in his usual sporadic style, which he thought would have brought him back closer to 160. But clearly he had been gaining more than he realised. No wonder Olivia was pissed at him, he thought, he certainly looked softer than he ever had.

Later in bed he snuggled up to Olivia and apologised for letting himself go, and promised to lose the weight. She mumbled approvingly and they had perfunctory sex, satisfying neither of them. Unfortunately he did not know that Jess had other plans.


Jess was a good girl. She had never approached a guy who she knew to have a girlfriend: she had been on the receiving end of that, and to put it mildly: it sucked. Jack however was a new proposition for her. She had never felt such chemistry with a guy before, he relaxed her, which was unusual for a boss, and they could laugh easily about anything. Knowing that he was taken she had done her best to keep flirting to a minimum and actively made sure that others were always around them so that she wouldn’t do anything stupid. Having met Olivia, however, she changed her mind.

Jack deserved someone much better than her. He deserved someone who made him laugh, and took care of him. How could that bitch continue a phone call while her man fell and hurt? And then when she finally deigned to pass by, she immediately blamed him for the accident! Fuming to herself, Jess found solace, as she always did, in a bar of chocolate as she lay in bed before sleeping, thinking of a strategy to win him over.