The secretary's spread

Chapter 1

Listen to this chapter - just press play:
"Hey, Sweetheart, we need to get going in ten minutes." A man's voice shouted from the kitchen.

Sweetheart. It still felt weird to hear those words coming from her boyfriend, Finn. A man Hillary would have never in a million years imagined would ever be her boyfriend. Though he was kind and at least decent looking, he fell far short of her usual jock type.

Quite frankly, Finn was way too fat for Hillary. The man had a huge gut and beefy physique that reflected the sheer absence of athletic ability he possessed. He was also much shorter than most of the guys she usually went for. Finn was about 5ft 8in, which was still taller than Hillary, but not tall enough for her. His face was pleasant enough. Finn had a scruffy beard and soft kind eyes, but those were the only two physical qualities Hillary found anything of value in. Despite her reservations, Hillary believed she couldn't do much better. At least the way she looked now. Just two years ago, Hillary had flat out rejected and then friend-zoned Finn. She even remembered laughing with her girlfriends about how someone like him could even think he'd have a shot with her. Now, Hillary just felt lucky anyone wanted to call her their girlfriend. It had been so shocking how quickly her dating life had evaporated.

Fidgeting with the buttons on her top, Hillary sucked in as she tried to button up blouse. Once victory was finally achieved, she relaxed, felt the shirt loosen, and heard something ping across the room.

"Oh god.. not again." Hillary sighed, utterly defeated.

This now made it the third time this month she had popped a button. It was Hillary's complete stubbornness that kept cramming her body into clothes she had no business leaving the house in. Somehow, it felt like another defeat whenever she normalized a size or two up in her wardrobe.

"Just perfect.." Hillary muttered to herself, slumping forward and waddling over to the bedroom mirror to inspect the damage.

Hillary hated having a mirror in the bedroom but understood the practicality of it. Finn needed it to dress nicely for his job as a legal assistant. Once upon a time, Hillary gave a shit about looking cute, spending hours in front of the mirror. Getting ready for work, dates, or trying out new looks. Now, not so much.

Just seeing her own body come into frame made the 27-year-old secretary shudder. Observing as her movements matching the movements of the massive blimp of a cow in the mirror still threw Hillary off. Hillary was fat. Very fat. She was pushing just south of 300 pounds last time she checked. Hillary also was reasonably short, at a petite 5ft3'. Where once her short height had been cute, now it was a curse, effortlessly showing off every single pound she gained. All of that lard sticking to her body was a reminder of the stupid choices she had made just to try to get ahead in her career, only two years ago. Stupid decisions that were barely paying off. Now, here she stood, in all of her glory. A disgusting morbidly obese version of the hot girl she had been her whole life.

Truth be told, Hillary used to be a total knockout and still had some of the hallmarks to prove it. Long silky dirty blonde hair framed her face, usually drawn up in a ponytail with a bow in her hair, a continued habit from her cheerleading days. She had creamy milky white skin with cute freckles across her face. Deep blue round almond eyes that were sharp and so full of emotion had broken plenty of hearts. Finally, her face was accented with a dainty button nose with full and pillowy lips made for kissing. Once upon a time, she represented the perfect combination of cute and sexy. Nowadays, she'd be hard-pressed to find anyone who'd give her that honor. A double chin and full cheeks now made themselves as much a part of Hillary's outward appearance as the rest of her features. It was a significant blow to the poor girl's identity and self-esteem.

Turning from side to side, Hillary inspected the borderline comical way her body was packed into her top. The remaining buttons on her white blouse were straining hard to contain the blubbery flab stuffed inside. Hillary cringed as she saw her lower belly hanging out the bottom of her top, sagging down over her crotch like an overinflated water balloon filled with cottage cheese. In frustration, she pulled the top off, popping some of the other buttons while the jiggling mess of flab all over her body shook. The sudden action left Hillary a bit winded and red-faced.

Facing herself in just her underwear and glasses was not a start to the morning that Hillary was seriously desiring. "Good lord.." Hillary exclaimed to herself, turning her ass around so it was in full view. It was like looking at a car crash in realtime. So terrible and horrifying, but she couldn't look away. The panties she crammed herself into were her last Victoria Secret panties that she could even pretend still fit. The rest were in a growing pile of outgrown clothes she had shoved towards the back of her closet. Something about wearing sexy panties made her feel the smallest bit of confidence in herself. Yet Hillary was the first to admit, her last pair of sexy panties had the opposite effect she intended.

Her asscheeks greedily swallowed the material, barely giving enough stitching to cover her cheeks. Unfortunately for Hillary, the exposed flesh of her doughy rear fully displayed an even fatter widening ass with more cellulite littering her skin than she remembered. About a quarter of her ass crack was exposed, giving her a quarter moon plumber's crack. The waistband of her panties dug into her hips, cutting into her circulation. The fabric was frayed and the elastic worn, but it was hard to tell since so little was exposed. In the front, Hillary would have had to lift her soft belly to reveal the small triangle of material covering her fat and underused plump pussy.

Her bra faired a little better. Admittedly, Hillary didn't mind that her tits had grown from a C cup to a Triple D cup. If there was one positive to take away from her ballooning, it was the tits. Even though they sagged a lot more, as long as she stuffed them into a push-up bra, she had an overflowing rack to put on display. The most annoying thing was that bras dug into her backfat, making the fits rather tight. The bigger problem for Hillary was that her belly stole the show, pushing out a few inches further than her boobs.

Just the sight of her reflection had been enough to put Hillary in a melancholy mood. She hated the way her body looked and felt utterly disgusting with her size. Being as big as she was made Hillary feel like a fat pig. Yet all of this.. nearly all of this weight had been intentionally gained. Hillary felt so stupid for letting things get so far out of her control. It was only supposed to be a few pounds but..

"Hey Hillary, are you almost ready?"

Finn entered the room, causing Hillary to snap out of her self pity party. Her eyes went wide, realizing that she was still in her underwear, and he could see just about everything. Yes, Finn was her boyfriend.. but Hillary still felt extremely self-conscious about her body. Letting anyone see her exposed like this was too embarrassing. In a panic, Hillary grabbed her discarded shirt from the ground, holding it in front of her body like a shield.

"Can you knock!? I'm getting changed!"

Finn politely averted his eyes. "Oh, sorry.. I.. Well, just wanted to check and see if you were ready."

Hillary knew he meant well, but still. She knew he knew this was crossing a line. When she had found out she was heavier than he was, her insecurities about her body around him had skyrocketed. Part of her was worried that someday he'd look at her body and think that even he could do better. He had said that size wasn't an issue for him, but Hillary knew the truth. Hillary knew that Finn was attracted to the idea of her, not her body. He had wanted her when he first asked her out two years ago. Now that she was finally in his league, it wouldn't be long now before Finn realized she wasn't worth it. Maybe even he would friend zone her.

It wasn't like the sex was that great. It had slowed down a lot, getting to a routine of about twice a month. On those rare occasions, Hillary would wear an oversized bed shirt to hide her belly. Finn wasn't allowed to touch her stomach during sex, either. As soon as the sex started, Hillary wanted it to stop. It just made her feel so big and fat, feeling herself jiggle, hearing her fat slap about, and getting so out of breath so quickly. It was gross and awkward, but at least Finn seemed to enjoy himself. There hadn't been a single time yet with Finn, where Hillary hadn't faked her orgasms.

It wasn't as if Finn wasn't attentive in other ways. He was an excellent companion, a shoulder to cry on, and he provided her with unique and fun conversations. They had been friends for over two years and roommates for a year of that friendship. Yet, in a moment of vulnerability, when she had let him kiss her in his car at the burger king parking lot three months ago, they became more than just friends.

"Just give me about five more minutes. I'll meet you in the car."

*Authors Note:*
Feedback is highly appreciated. Helps me become a stronger writer.
15 chapters, created StoryListingCard.php 4 years , updated 2 years
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Brope 2 years
I love this kick you're on, both of these stories feel alive with energy and the characters are such lovable pigs. Truly top tier writing.
ConJohn 2 years
Thanks! These characters have been fun to develop, so it's good to hear they're being enjoyed.
AndiFive 2 years
so both stories are in the same universe, what a fantastic thing. I hope to see more of this universe in future stories.
ConJohn 2 years
Thank you! I plan on writing all my stories in the same universe. Expect more crossovers.
Fatowl 2 years
Great Story!! Hope Hillary gets off the mat and fattens Jenna while she loses weight and becomes hot again with a winning idea and promotion! Hillary is a secret feeder. And goes to the gym.
ConJohn 2 years
Thanks! I like where your head is at. I'm keeping the scope of this story to only take place in one day (just to temper expectations), but good ideas.
Eathamburgers 3 years
I really like where this is going!
ConJohn 2 years
Thanks so much!!
Champ 3 years
Incredible story. I love your writing style and content. It’s right up my alley. Please continue!!
ConJohn 2 years
A year late on my reply, but thank you!
NocturnalDev... 4 years
You are an incredible writer!!! Please continue! I can't wait for more chapters on Haley's Gain!!!
ConJohn 2 years
Oh wow! Thanks! I realize I'm replying a year later, but this means a lot smiley
ConJohn 4 years
Davidewol - Thank you!! Yes, I plan on divulging that information throughout the story, while still keeping it in the present tense. Stay tuned!
Davidewol 4 years
Excellent start so far!! I'm guessing this will tell the story of how she gained the weight in the first place?