Penthouse Piggy: Chapter 1

When the restaurant closed, Will found himself unemployed once again. He couldn’t count the number of times he’d enrolled for unemployment benefits in his life, let alone since he moved to New York City. Will did not come from money and he was beginning to feel increasingly defeated trying to get by in an unfair and corrupt system. Frustrated and depressed, he contemplated relaunching his OnlyFans account.

Throughout his late teens and early twenties Will had dabbled in sex work. He had his first sugar daddy when he was only 18 and living on his own at university. It wasn’t something he was looking for and he was shocked when the opportunity fell into his lap. See, Will had been a fat kid all his life. He was a complete butterball that never stopped eating and was teased mercilessly for it. He had never thought of himself as attractive. In fact, he felt the opposite; that he was a tub of lard that no one could ever love. At least, that’s what the bullies at school would say. But then he hit puberty and it all melted away. His metabolism kicked into overdrive, he picked up sports and running, and before he knew it he was more fit than most of his peers.

Slimmed down to a tight and tiny twink, Will discovered he was actually quite handsome. He had a chiseled face with high cheekbones and a strong jaw. Short cropped blonde locks lent him a boyish quality that accentuated his twinky persona. He was shocked to suddenly be receiving tons of attention from men, finding his Grindr inbox filled with messages. One such message came from an older gentleman who offered to pay him simply to hang out and chat. Desperate for cash, Will accepted. A few months later, he was whisked away on private vacations and living the high life. For the first time, he had a sugar daddy.

Eventually, this older man got bored and moved onto someone new. This reality was hard to accept at first, but Will came around to the idea that this was the nature of the game. Still needing to make ends meet, Will started an OnlyFans. He built a following online that paid him fairly well and he even found a couple more sugar daddies throughout his college career. The income kept him afloat and living fairly comfortably. While completing his history degree, Will found that his looks were the easiest thing to mine for profit. At times this was tiring and demoralizing, but he needed the money.

Once he graduated, Will headed straight for New York City. He had always dreamed of living in the big apple and he was determined to make it work. This time, without sex work. Not surprisingly, a history degree didn’t get him very far and Will ended up working multiple part time jobs to get by. He also dabbled in the gig economy to fill in the gaps. Life wasn’t easy in New York, but it was what he wanted. After a few years, however, Will was getting tired.

After Bartleby’s closed, Will felt defeated. He enjoyed working at the small restaurant and had grown close with all his coworkers. The food at Bartleby’s was top notch, but good food and loyal customers were no match for the skyrocketing rents. Will had even put on a meager 7 pounds while working there. The food was so delicious that he often couldn’t resist the tempting aromas encompassing him. That was the most weight Will had gained since he’d lost weight as a teen and he worried about the trend continuing.

Walking home on his final day of work, Will decided to treat himself. He stopped at a diner and ordered a slice of chocolate cake. This was a rarity for him. The last time he ate cake was when a boy he was dated broke things off abruptly. Will savored each bite of the delicious treat, knowing he wouldn’t be indulging again for a long time. Seated at the bar, Will took a sip from his coffee and noticed a handsome stranger watching him from across the room.

The man had light brown hair with a tasteful side part, a scruffy face, and puppy dog eyes. He looked sweet but Will also sensed an air of danger. As Will glanced over, the man confidently stared back and gave him a wink. Will’s heart fluttered. He looked down and smiled. When he looked back the man was still staring at him. Unsure what to do, Will looked down at his cake bashfully.

The man stood up and Will noticed he was wearing an expensive shirt and slacks. He looked wealthy. Will immediately saw dollar signs and grinned. A handsome man under 40 who was wealthy and interested? It sounded too good to be true.

“Matt,” said the stranger and held out his hand. “Nice to meet you.”

Will found it oddly formal to shake hands, but he followed suit and introduced himself.

“How are you enjoying your chocolate cake, Will?”

“Oh… It’s good. I uh… don’t usually eat cake, but you know… rough day.”

“I’m sorry to hear that,” Matt replied. “What happened?”

“I, uh, lost my job actually.”

Matt fought back a grin that made Will uneasy.

“Here’s my number,” Matt said and handed Will a business card. “I’d like to take you out sometime. I know where we can get the best chocolate cake in town, my friend is the chef. How’s that sound?”

“That… sounds great!” Will replied. “I’ll hit you up.”

“Why don’t you text me now so that I have your number. Let’s do tomorrow at 5 PM.”

The man was a little pushy, but Will was used to this behavior from wealthy men.

“Okay, sure thing. I look forward to it,” Will’s heart fluttered.