The CEO's Romantic Wager

Chapter Ten: The Return of Connor Waters

December slowly crept in like a thief in the night, and with it came the chill, the snow and that magical feeling that seemed to linger at this time of year whenever the first two were in place—everything that pointed to a wonderful, white Christmas.

The holiday spirit had fully incorporated itself into Creed Holdings, all thanks to Jayla and her hostile Christmas takeover, and now, the once cold and clinical workspace felt warm and inviting, trapping everyone in an infectious cheer—yes, even the grumpy employees.

Her work on the CEO, however, was still far from done.

You see, despite her best efforts, Ajax Creed remained an enigma—a man with moments of charm but whose grinchy attitude still lingered beneath the surface. Yet, even she couldn’t deny that he was changing... becoming a bit more welcoming to Christmas concepts and events.

The billionaire boss and his assistant were really kicking things off with their secret arrangement as well, and the world was already buzzing with whispers about their supposed relationship.

It was everything Ajax Creed had been hoping for.

The arrangement was working flawlessly, the facade convincing enough to draw attention away from his personal life, and his old controversial relationships. And yet, despite the outward success, the billionaire couldn’t ignore the growing weight in his chest.

The guilt.

It was relentless, clawing at him every time Jayla flashed him that brilliant, captivating smile or laughed at one of his half-hearted jokes. She was giving this arrangement her all, and truly, her sincerity towards the cause was undeniable and genuine, meanwhile he... he had started it with ulterior motives… lies.

You would ask why any of it mattered now to the billionaire playboy when, for so long, he never cared what someone who wasn’t family thought of him.

The thing was, his feelings for Jayla were growing by the minute.

The realization had hit him one evening as they wrapped up a late-night ice cream date. She had bought some ice cream for a homeless man lingering outside, and headed out to give it to him, and while he watched their interaction and the sheer joy in her eyes at the man’s excitement, his heart had warmed up in ways he had never thought it could.

But even if he wanted to take things to the next level—which he wasn’t entirely sure he did yet—what hope could there be for a relationship built on lies?

Ajax leaned back in his office chair, staring out the floor-to-ceiling windows. The city lights sparkled like tiny stars in the night, and on a normal day they might have calmed him. In a holiday season like this, they might have irritated him, but instead he saw none of that.

All his mind could churn were memories of him hanging out with his assistant, making her laugh… really liking the way she rolled her eyes at him when he said something out of pocket…

It was nighttime, and he should have been home, but thoughts of her haunted him even more there, though then again, being in the office wasn’t any different.

The sound of a knock at the door broke his thoughts.

Who could that be at this hour?

Maybe Jayla had come from home to check on him?

“Come in,” he called out, his voice more excited than he intended, but when his command was obeyed, it turned out to be none other than his best friend, Connor Waters.

As the tall, charming man strode into the office with all the subtlety of a hurricane, Ajax braced himself for a storm.

Things had been simple, easy, with Connor away on a one-month leave. He was afraid of what it would be like now that he was back.

“Creed!” Connor’s booming voice carried across the space as he marched towards his friend. “Did you miss me, baby?”

Ajax shot him a pointed look, eyeing his leather jacket and protective biking gear, but he didn’t say a word. His silence made Connor chuckle as he settled into the chair opposite him, his leather ensemble ruffling under his weight.

“Why are you here at this time, Connor? If your Biker gang just got into the city, shouldn’t you be heading home instead?” The CEO asked curiously as he leaned back in his chair, keeping his expression neutral.

“I was going to, and then your doorman told me you were here,” Connor admitted, “I got word about how a certain someone was making considerable strides with his assistant. You sly dog!” He teased his friend.

“I honestly thought you had no hope with that serious, no-nonsense girl, but somehow, you have managed to snag her for yourself after all.” Connor continued, totally oblivious to his friend’s weird silence.

“You know, the IT department needed you to look over their proposal for the new year. Since you’re back, I’ll have it sent to your email so you can take a look at it,” Ajax tried to evade the topic, but Connor was having none of it.

“Don’t change the subject, man,” He shot back, though his lips quirked in the faintest hint of a grin. “I leave you for just one month, and suddenly you’re the talk of the town? Dating your assistant? Really?”

Ajax sighed, pinching the bridge of his nose. “It’s not as serious as people are making it out to be.” He tried to reduce his friend’s fixation, lest his carefully built block of lies come tumbling down.

Connor scoffed. “Not serious? Please. You assured me that she was not your type, and yet you’re hanging out with her. Which is why I’m thinking...” He paused, his grin widening. “...that this has something to do with our little wager.”

Ah f**k.

Ajax stiffened, but he quickly masked it with a casual shrug. “I don’t know what you’re talking about.”

“Oh, don’t even try it.” Connor leaned forward, his voice dropping to a conspiratorial whisper. “You really went through with it, didn’t you? The bet. Make the icy assistant fall for you. Man, I didn’t think you had it in you.”

“Connor...” Ajax’s voice held a warning note.

“No, no. Don’t get all broody on me now.” Connor waved a hand dismissively, his grin stretching ear to ear. “A deal’s a deal. And since you totally pulled it off, I’m here to make good on my end of the bargain.”

He tossed something onto Ajax’s desk—a key.

Ajax stared at it, his jaw tightening. “What’s this?”

“Your prize,” Connor said smugly, a little sadly. “My little girl, my Neiman Marcus Limited Edition Fighter. Not only that, but you just won yourself,” He pointed a finger at Ajax, “A spot in my biking gang. I know just how much you miss the one you left behind in Paris. You’ve earned it, man.”

Ajax’s chest tightened.

The bike was a prize he’d seriously coveted for years—custom-built, sleek, and one-of-a-kind. And as for the Manhattan Tweezers, they were exclusive, non-violent and perfect… so perfect that their selection process was rigid even for a billionaire like himself, such that he hadn’t even dared to apply.

And now he had a spot.

But as Connor sat there, looking so damn pleased with himself, all Ajax could think about was Jayla and what accepting all of this would mean.

She didn’t know about the bet.

And as much as Ajax had started this whole thing with a calculated, detached approach, he’d been blindsided by how much he actually cared for her now.

“I can’t take this, Connor,” Ajax shook his head, pushing the key back towards his friend.

“What?” Connor blinked, genuinely confused.

“The bike, the gang... I’m not interested anymore.” Ajax stood, pacing to the window.

He didn’t meet Connor’s gaze as he continued, “I haven’t even met the other agreements in the bet, but this stopped being about the bet a long time ago.”

Connor frowned, leaning back in his chair. “Wait a second. Are you telling me you actually like her?”

Ajax didn’t answer right away. The silence stretched between them, broken only by the faint hum of the office outside.

The CEO finally turned to face his friend. “She is growing on me, man. Jayla is not just some game, Connor. And I don’t want to be the kind of guy who plays with people’s feelings like that.”

Connor studied him for a long moment, his usual playful demeanor replaced by something more serious. “You’ve got it so bad, don’t you?”

Ajax didn’t deny it.

“Well, shit.” Connor ran a hand through his hair, looking almost impressed. “Never thought I’d see the day. But you know this means you’ve got to come clean, right? About the bet? I can only imagine what would happen if she found out any other way.”

Ajax’s stomach churned at the thought. “Not yet,” he said quietly. “I just... I need more time. Things are already complicated enough.”

Connor nodded and stood up, but he slid the key towards his friend anyway, “Despite not wanting anything to do with it, I still think you deserve this, Ajax. Who ever thought we’d see the day when the notorious Ajax Creed started to have feelings for just one woman?”

Certainly not him.

“You’re building a relationship without any ulterior motives… based just on genuine connection and nothing else. You really deserve this, Creed. It’s nice to see the man you’re becoming.” Connor finished earnestly.

Okay, now Ajax felt bad.

How did he tell his friend that the reason Jayla was with him was because he had coaxed her into an arrangement with him?

He never thought he’d see pure, genuine respect form in Connor’s eyes on his account, and now that he had, he wasn’t sure he wanted to let that feeling go, and so he kept mum.

“But you need to tell her about the bet, and you need to tell her soon before things progress, Ajax. Let me just say this—you’ve got a good thing going with her. Don’t let your pride—or your fear—mess it up.”

With that, he clapped Ajax on the shoulder and strode out, leaving him alone with his thoughts.

As Ajax stared out the window, the city glittering in the distance, he felt the weight of his choices pressing down on him.

He’d wanted to win.

He’d wanted the bike, the bragging rights, and the thrill of knowing

He still got them anyway, but all he truly wanted was Jayla.

They had that volunteer thing coming up as their next major activity.

Fingers crossed, he was going to come clean to her over there.