Married to a Stripper

Ryan was sitting at his desk, his shirt sleeves rolled up to his elbows. He was breathing deeply, muttering curses under his breath as he read his grandfather's will for the hundredth time. I couldn’t believe it. After everything he’d done for the old man and the company, this was his payback. A forced marriage? For what? Neither he nor his father had been happy in their marriages. Why was that?

He knew that his grandfather had strict beliefs and high expectations, and for the company’s good image, the person responsible had to assume an integral and well-received stance in society. But what the fuck? This isn’t the fifties.

The absurdity of the idea alone made him furious, wanting to punch the wall. Ryan tried to calm himself, but all he could think about was how to fix this mess. Sighing, he stood up and walked over to the window, his eyes scanning the traffic on one of the busiest streets in Chicago. His thoughts were interrupted by a knock at the door, and Mrs. Smyths, his assistant, stepped in. She’d worked for his grandfather before, and now she was with him. She told him Mr. Pierce had arrived. He followed her into the room, keeping his usual cheerful expression.

“Tom, only you could come in here looking so happy,” Ryan said with a hint of sarcasm, heading straight to the corner cabinet where he kept his whiskey. He poured two and walked over to Tom, who had already taken the liberty of going through the will spread out on Ryan’s desk. Tom was dressed in a pair of dockers and a casual plaid shirt, a stark contrast to Ryan’s more polished look.

"Pull yourself together, Ryan," Tom said while accepting the drink. "You’ll figure this out... You’re not the first, nor the last man to have an arranged marriage.”

"Yeah," Ryan muttered, pacing back and forth across the room, his hands running through his hair in frustration. "I ended things with Jessica because she’s a gold-digging bitch, and now I’ve got to find someone just like her, just to get everything I’m entitled to, everything I’ve worked for these last 15 years. Fuck, Tom. It’s like I didn’t spend all this time building Carter Enterprises into one of the best in sustainable building development. Might as well go back to Jessica."

Tom raised an eyebrow, shaking his head. "Are you out of your mind?" he said, leaning back slightly but still fully engaged. "Jessica was a slut who’d sleep with anyone she could. The best option here is to find someone with no ties to you, someone who’ll see this as a business transaction."

Ryan stopped pacing, turning sharply to face Tom, his eyes narrowing as the frustration boiled over. "Where the hell am I supposed to find someone like that? This marriage must look real. If the executor of the will finds out it’s fake, the company goes public. And you and I lose everything. Or do you think you can just find another company and start designing buildings the way you want?"

Tom leaned back in his chair, eyes scanning the room as if deep in thought. Then, as if something clicked, he sat up straighter and gestured with his hands, almost as if he was about to unveil a solution. "Ryan, listen to me," he started slowly, his voice more thoughtful now. "I get it. You need someone who can play this role, but it can’t just be anyone. It has to be someone who doesn’t have a personal attachment to you, someone who can separate business from emotions. What you need is... someone motivated by money."

Ryan stopped pacing and shot him a skeptical glance. "What are you getting at?"

Tom raised a hand, signaling Ryan to wait. "Hear me out. I know this sounds a bit crazy, but you need someone who isn’t gonna get involved emotionally, someone who doesn’t care about you or your family. They’re in it for the cash, and that’s it. No strings attached."

Ryan’s frown deepened. "Okay, but how do you find someone like that?"

Tom's eyes glinted as he leaned forward, lowering his voice. "You’re looking for someone who’s used to... transactional relationships. Think about it. An escort, maybe. Or a stripper. They’re not your type, sure. Too rough around the edges for your ‘refined’ tastes." He let out a short laugh, almost apologetically. "The thing is, they’re not doing what they’re doing because they enjoy it. They’re doing it because they need the money. They’re professionals. They know how to keep it all business, no drama, no feelings."

Ryan blinked, caught off guard by the suggestion. "A stripper? An escort?" His voice was disbelieving. "You really think that’s the answer?"

Tom shrugged nonchalantly, a slight grin forming. "Why not? They’re the kind of people who could play the part. No emotional investment. You’re not trying to fall in love, Ryan. You’re just looking for someone who can show up, act the part, and make this whole thing look real for the public. Once the year is over, you both walk away with exactly what you need."

Ryan stopped pacing, his hands clenched at his sides. He shot a glare at Tom, his jaw tight with frustration. "Because it’s completely ridiculous," he snapped. He took a deep breath, walking back to his desk, running a hand through his hair. "I can’t just hire some woman like that to pretend to be my fiancée."

Tom raised an eyebrow, not backing down. "Alright, but when you realize you’re running out of options, I’ll be here, ready to make the call. You know where to find me."

Ryan’s gaze flickered to Tom, his smirk still hanging at the edges of his mouth. For a moment, he saw the sincerity behind Tom's devil-may-care attitude. Tom was never the one to follow the rules, and his boldness had a way of cutting through Ryan’s more rigid thinking.

Ryan turned back to Tom, his voice low and tight. "Who do you have in mind?"

Tom leaned forward again, his grin a little too knowing. "I’ve got connections. You wouldn’t believe the people I know, man. Trust me, we’ll find someone perfect for the role—someone who needs the money, no emotional baggage, no questions asked. Just a business deal."

Ryan narrowed his eyes, still processing the implications. "And you really think this will work? Just... fake it for a year, and then everything goes back to normal?"

Tom shrugged casually, the same devil-may-care attitude never leaving his face. "That’s the idea. You don’t need a real relationship—just someone to play the part. After a year, you’re free, and everyone gets what they want. Hell, the woman you hire probably won’t even care. It’s the perfect win-win. No emotions, no drama."

Ryan couldn’t help but let out a bitter laugh, shaking his head. "This is insane."

"Yeah," Tom agreed, leaning back with a smirk.

Ryan didn’t answer immediately, his gaze flicking back to the skyline beyond the window. "Alright. Let’s see where this goes."