Hefty Halloween, Part 1

This story was the winner of my "What Should I Write in October" poll, and I'll be posting the next two chapters over the next few days. Enjoy!

As Kevin Kobayashi got dressed for this year’s annual Halloween party at the Regal Bay Towers, he thought about the other Halloween events he had attended since moving into his condo.

Five years ago

Kevin had fallen in love with Seattle seven years earlier as a college freshman at the University of Washington. He loved everything about the city – the people, the climate, the outdoor activities – and definitely hoped to make it a home after graduation. It was an expensive place to live, however, and after saving money by living in cheap apartments and riding his bike wherever he needed to go, Kevin had earned enough from his financial consultant position to afford the mortgage on a condo at the brand-new Regal Bay Towers downtown. It was the perfect place for him – just a block from his office, and right in the center of a vibrant community with lots of amazing restaurants, bars, and nightclubs.

One of the best aspects of living at the Regal Bay was that it provided an excellent opportunity for Kevin to meet potential clients. Many of the younger owners were looking for a trusted partner who could provide them with sound investing advice, and they enjoyed working with Kevin because of his easygoing demeanor, charming personality, and ability to present financial information in an uncomplicated way.

Oh, and his looks didn’t hurt either. Kevin was tall (6’3”), with a handsome face, jet black hair, big smile, and a well-toned, 195-pound body. He had played basketball and baseball back in high school and kept up his gym routine in college, so he was in tremendous shape and looked good in just about any outfit. Many people would ask if he had ever done any modeling, which always made him laugh, but he definitely could have if he pursued that career.

But Kevin was focused on making it in finance, so he used every opportunity to schmooze Regal Bay residents and let them know he would be happy to help them grow their nest eggs. Fortunately, a few months after he moved in, he noted a sign on the bulletin board next to the mailboxes in the lobby – that night, October 29, the homeowner’s association was hosting an adult Halloween party for residents and their friends. Kevin figured it would be a great place to meet other owners and make a lot of connections all at once…he would just need a great costume to attract a little attention.

Kevin looked at his watch right after seeing the sign…it was already 4:45pm, and the party started at 6:00pm, so he wouldn’t have time to go out and buy anything. He’d just have to make do with whatever he could find in his closet, so he hurried upstairs to begin his search. He mostly had suits for work and athletic gear for the gym – there wasn’t a whole lot to make a costume out of. Kevin did have some jeans that he would wear during the colder months, a few hats, some odd-looking belts – and then suddenly he figured it out. He put on the tightest pair of jeans he owned, along with a white belt, and then cut the collar and cuffs out of one of his while oxford shirts and put them around his neck and wrists. Finally, he added a black bow tie over the white fabric already around his neck.

“I make a pretty good Chippendale,” thought Kevin as he checked himself out in his full-length mirror. He swiveled his hips a few times and then flexed his abs – he didn’t have the biggest muscles, but he was well-defined, and he loved to show off his tight midsection whenever he could.

After putting a little more product in his hair and spritzing himself with his favorite cologne, Kevin grabbed some business cards and artfully tucked them into the waistband of his jeans. He then rang for the elevator, took it down to the lobby, and entered the large room where the party was being held. About 40 people were already there, and almost every head turned – with big smiles on their faces – to watch him walk in. “I think I may get a few new clients tonight,” he thought, as he headed for the buffet on the far side of the room.

Four years ago

Wearing his makeshift Chippendale dancer costume to the Halloween party could have backfired for Kevin, as some people may have thought it to be too risqué, but the gamble ultimately paid off – he was easily the most talked about (and most gawked at) person at the party, and he ended up getting eight new people signed up for his investment services. And thanks to the strong market over the next six months, Kevin earned multiple bonuses on these accounts and managed to fatten up his bank balance.

But that wasn’t the only thing that fattened up. With the extra hours he was putting in at work, plus the fact that he no longer needed to ride his bike every day, the pounds began to creep onto Kevin’s once-ripped body. By April, he could tell his shirts, blazers, and pants were getting a little snug – they had all been custom-made and were only ever dry-cleaned, so he was fairly certain he was going to be the problem. One morning when he didn’t have to be in the office super early, he took the time to dig out his old scale and stepped on it to find out what he weighed. Instead of his normal 195, where he had been at since college, the number said 210. Kevin wasn’t terribly surprised, given how busy he had been (and how many client lunches and dinners he had been to recently), and really, he didn’t look fat – just not as lean as he used to be. His stomach was still pretty flat, but he could not longer see his once deep-etched abs or the veins that used to crisscross his Adonis belt.

When confronted with the change, Kevin decided immediately to lose the extra poundage. He had spent too much money on his clothes to replace them already, plus he wanted to look good at the Regal Bay pool in the summer, so he started hitting the gym each night when he got home from work instead of collapsing onto his couch with some chicken parm from DoorDash and watching Netflix. Thanks to this activity increase, along with his youthful metabolism (he was still only 26), Kevin shed the extra weight within a few weeks and was back down to 195 by the first sunny and warm day in May.

Later that year, as Halloween approached, Kevin was still on his fitness kick and looked better than ever, so he decided to go to the Regal Bay party in the same costume he wore the year before.  After getting everything on, he checked himself in the mirror, adjusted his crotch a bit, and smiled broadly at his handsome reflection.

Kevin sauntered back down to the party area hoping to garner at least as many clients as he had the year before. He had already hooked at least 3 new fish when something unexpected happened: he ran into Zane Taylor, a former classmate from his high school. Zane was also an athlete, but he had been on the football and wrestling teams during his time at Cooper High, so he and Kevin’s paths only crossed occasionally. But just like Kevin, Zane had clearly kept up on his fitness since graduating and now rocked a 6’1”, 235-pound body full of rippling muscles. With his brawny physique, white-blond hair, and light skin, Zane had come to the party dressed as Bamm Bamm, and he was attracting just as much attention as Kevin.

After a rather long hug, the pair reminisced about their time in school and caught up with one another – Kevin mentioned his work at the brokerage firm, and Zane said he had just moved to Seattle to work in pharmaceutical sales and had come to the party since his cousin lived at the Regal Bay. It was a bit hard for both men to focus on the words being spoken as they were both checking out each other’s bodies – neither of them had been out in high school, but they quickly figured out that the other one was gay and ready to hook up. Five minutes later, they were entering Kevin’s bedroom, shucking their clothes, and hopping into bed for a very satisfying fuck session.

After taking turns where each topped then bottomed, Zane wanted to try something he had never done before and slid his cock up and down the ridge between Kevin’s abs – both men found it to be incredibly erotic as they stared into one another’s eyes and felt the friction of their bodies, and eventually they came harder on that third time than they did the first two times.

The next morning, to thank Kevin for the night before, Zane insisted on getting up and cooking breakfast for both of them. Kevin could hardly refuse, especially since Zane was going to do so while still naked and he could ogle the man’s unbelievably striated ass while he flipped the pancakes.