The Price of Losing

Taking the Step

As Oliver tried to steady himself, Lily turned to Jess. "So how long has he been your little assistant?"

Jess smiled, catching onto Lily's curiosity immediately. "Oh, just a week or so," she replied, as though it were the most normal thing in the world. "But he's adapting well. It's actually kind of cute how easily he slipped into the role."

Oliver could feel his cheeks burning as Jess spoke so casually, as if he weren't standing right there. He shuffled uncomfortably, trying to look away, but Lily's laughter drew him back into the conversation.

"And what exactly do you have him doing?" Lily continued.

Jess raised an eyebrow, clearly enjoying the moment. "Oh, a little bit of everything. Restocking, assisting customers, helping me with demonstrations..." She leaned in a bit, her voice dropping to a whisper that was somehow still loud enough for Oliver to hear. "And I've been teaching him to stay very, very focused."

Lily laughed, shaking her head in amusement. "Focused, huh?" She eyed Oliver, sizing him up in his latex suit and collar. "I can't believe it. The Oliver I knew would have never agreed to this. You must have something on him," she teased Jess, winking in Oliver's direction.

"Oh, I do," Jess replied smoothly. "And it keeps him right where I need him."

Oliver fumbled for words, wanting to defend himself, but Lily was already looking him up and down, as if assessing this new version of him. "Well, I think it suits you, Oliver," she said, a playful lilt in her voice. "Though it sounds like Jess might just be getting started with you..."

Oliver could only stand there, swallowing back his embarrassment as he felt himself pulled further into the world Jess was crafting around him.

Lily tilted her head. "You know, Oliver," she began, "if I'd known you could be molded like this, I might've kept you around. I could've had you as my personal assistant. Locked up, obedient, doing exactly what I said." She leaned in closer. "And trust me, I wouldn't have been as nice as Jess here. I'd have made sure you never forgot who was in charge."

Oliver swallowed hard. He glanced nervously at Jess, who simply raised her eyebrow in amusement, clearly loving every second of his embarrassment.

"If only I'd known, I could've had you dressed up, at my beck and call, running every little errand I needed and looking just like this every day." She laughed softly, as if the thought truly delighted her. "And keeping you locked up? Oh, I'd have made it way worse for you, Oliver. You would've been begging for mercy."

"Seems like you really missed out, Lily," Jess said. "But don't worry. I'll keep him in line here."

Lily threw Oliver one last, lingering look. "Well, don't let her be too gentle with you," she said, her voice playful but pointed. "I expect to see you next time, looking just as helpless." Then, she turned and left the shop.

As soon as Lily left, Oliver turned angrily to Jess. "That's it, Jess. I'm done with this—done with all of this. I never agreed to be treated like some kind of... of display for everyone to laugh at!"

Jess just raised an eyebrow. "Oh, really?" she said with a casual shrug. "Seems to me like you're overreacting to a bit of harmless fun. You're the one who agreed to play along, remember? And don't tell me you haven't been enjoying the attention."

He shook his head, trying to hold his ground. "Jess, I'm serious. I can't keep doing this. I want to go back to normal. No suits, no collars, no teasing in front of strangers, and definitely not having my fucking cock caged."

Jess crossed her arms as she looked him over. "Alright, so you've had a tough day. But you're telling me you're willing to just walk away from this? From all the excitement, the thrill?" She stepped closer, her voice dropping to a gentle, persuasive tone. "Don't pretend you haven't felt more alive than ever. You're learning to step outside your comfort zone, something you've never done before."