Chapter 1: First Encounter

After a rather long hiatus on writing, I decided I wanted to re-edit this story to improve the quality and potentially add to it. Expect new chapters in the near future :)


It was a bitterly cold December night in Chicago. Despite the blustery conditions, Troy Allen’s mood was jovial. He and his friends were going out to celebrate. The twenty-three year old, recent college-grad had just gotten his first promotion at the investment banking firm he worked at. The occasion called for a night out on the town. After a short walk from their firm's downtown office, Troy and his friends slipped into a new bar that had been recommended to them. Once inside, a svelte hostess greeted them at the door. She was dressed in the bar's revealing, hooters-esque uniform. Although the uniform was accomplishing its goal of being provocative, it was completely impractical given the ongoing, brutal midwest winter. Troy’s friends, who were primarily fellow financial sector workers from his fraternity, ogled the hostess' tight shorts and low cut top without shame. One of them even whistled upon being welcomed in the door. Trying to stay professional and hospitable, the hostess explained that the counter area was at capacity but advised the group that they did just have a booth open up in the back corner.

Troy followed his group over to the booth, but while doing so, someone caught his eye. Leaving the area behind the counter and heading towards the exit door, was an absolute bombshell of a woman. Troy only got a brief look from a distance of a heavy-set woman, dressed in the same skimpy uniform the waitress and hostess had on. He estimated she looked to be about 5’4, and about 300 pounds, with most of the weight in her corpulent rear and thick thighs. While heading out the main door to the street, her body finally turned to face him, revealing more of her figure. Her face was too far away to get a read on, but it was framed by long blonde hair that complimented her silky, white skin. Even from a distance, Troy could tell she had the best kind of womanly shape; a sort of pear-hourglass combo, who despite having colossal hips and an ass like a shelf, still possessed full breasts whose slight perkiness defied their obviously heavy nature. Before Troy had even had three seconds to stare she headed out the door and out of view into the swirling winds of the night.

The night continued on as most nights out with this group did. The drinks were flowing and the group reminisced about their time together in college and the fraternity. Although enjoyable, Troy couldn’t shake the memory of the full-figured employee he’d gotten a view of when they’d first come in. While his friends made lewd sexual comments about how their current waiter and other bar staff were total knockouts, Troy still couldn’t get the women he’d seen earlier out of his head. Troy just couldn’t see the appeal of a girl like their waitress who had such meager bodily proportions. Still, he played along and flirted with the current staff enough to appease his friends. In truth, Troy didn’t find their current waiter (or the other current staff) to be very attractive. Sure they had stereotypically pretty faces and perky features, but Troy couldn’t get past how bony and thin they all looked to him. All in all, Troy was still in the closet about his admiration of bigger women.

Generally during college, Troy had dated women just like the current bar staff; thin, sorority girl’s that looked to match a finance majors future partner. These types of girls were the obvious match, given Troy was 6’1, smart, a student athlete, and from a wealthy, respected family. Still, Troy felt deep dissatisfaction being with the women he was expected to date. This dissatisfaction manifested in the fact that his relationships would always go sour when things in the bedroom didn’t materialize. Then, even though he knew deep down it wasn’t fair to the girls he dated, he would cheat or break things off to secretly hook up with girls with larger figures.

Near the end of college he had finally worked up the courage to date one girl who was on the chubbier side. Standing at about 5’5 and weighing about 200 pounds, Claire had been kind, down-to-earth, funny, and sexy. Despite being a much smaller size than his truthful preference, Claire represented a step forward in his confidence to date who he really wanted to. Things had been going so well in the first 8 months of the relationship; that was until Thanksgiving of that year. Nervously, Troy had taken Claire home to meet his family for the first time. He knew Claire was not the type that his pretentious family expected him to bring home. Claire didn’t have any ambitious plans for after college. She was an art major, with no concrete career plans but to follow her passions and create. Further, Claire didn’t come from any money, wear fancy clothes, or pretend to be more than she really was. These things had been endearing to Troy, but to his family, they were problems.

That Thanksgiving had been a disaster. In the end, Claire had left dinner in tears and blocked Troy’s number. Troy never found out if the breaking point was his family's comments on her weight, the snide comments about the amount of food on her plate, or his parents remarks about how she “lacked the qualities needed to be with our son.” After Claire had drove off, Troy was given a lecture about needing to be with someone who was actual “wife material”. If his family hadn’t been bad enough, when he announced to his friends that he and Claire were done, they’d been relieved. As put by one friend, “You dodged a bullet with that one, Troy. If she was already that size she was in college, she was only gonna fatten up more once she finessed a ring outta you.”

Troy was humiliated by the fallout of his relationship ending. Between society's expectations of him and his family and friend comments, Troy concluded that fat girls were off the table for relationships; at least until he had more separation from his family and current friends. Since graduation he had decided fat girls would just be for hookups and one night stands. The problem was since the end of college a year and a half ago, the influx of parties and gatherings that produced hook-ups was gone. Even on the “wife material” front, things had been dry with how busy work at the firm had been. All in all, Troy’s sexual frustrations were at a breaking point. Inside, he just knew that he needed the rotund women he'd seen at the bar to be his, even if only for a night.