The Price of Losing

Customer Advice

Oliver's weekend was different from usual. Free from the confines of the cage, he'd tried to unwind, but his thoughts kept drifting back to Jess and the peculiar new world she'd opened up for him. He spent Saturday morning trying to distract himself with errands, and by the evening, he finally allowed himself to relax. But come Sunday, he was restless again, his mind wandering back to the shop and all the teasing, thrilling interactions he'd had with Jess. Despite himself, he found he was actually looking forward to Monday.

Finally, Monday morning arrived. When he arrived at the shop, he saw Jess was already inside, arranging displays with her usual energy, a small smirk already on her lips as she noticed him walk in.

"Morning, Oliver! Did you rest enough?" Jess teased, glancing him over.

He felt his cheeks warm, but he managed a smile. "I hope so."

Jess chuckled, coming over to him. "I hope you're rested, because this week is going to be even more intense than last week."

Oliver nodded, feeling his heart pick up a bit.

"Well, let's get you properly 'prepared' for the day then, shall we?" she said with a playful lilt, gesturing for him to follow her into the storage room.

Once inside, she reached into a drawer and took the chastity cage he used last week. "Ready?" Jess asked, holding the cage up with a knowing look. 

He took a shaky breath and nodded, steeling himself as he fastened it in place. Jess observed closely, when he was done, she took the small key and dangled it teasingly for a moment before slipping it onto her necklace.

"There we go," she said, giving his shoulder a gentle pat. "Now that you're set, let's get you out front. I have a feeling today's going to be our best sales day yet."

The feeling of the cage brought him a renewed awareness of every movement as he followed her to the front of the shop. He could tell Jess was ready to keep him on edge.

Just after opening, a middle-aged woman entered. She started looking to all the things that were displayed on the shop and eded up eyeing a display of leather harnesses. Jess caught Oliver's eye and motioned him over.

"Oliver here can help with all your questions on these items," she said with a grin. "In fact, he had some firsthand experience with our gear." She shot him a look that made his stomach flip, while the customer raised an eyebrow, intrigued.

The woman turned to him. "So, these are comfortable?" she asked, holding up one of the harnesses and giving him a curious look.

He nodded, feeling his cheeks grow warm. "Y-yes, ma'am. They're designed for both comfort and security."

The customer chuckled and tilted her head, giving him an appraising look. "Interesting... I might need a bit of help with the buckles. Do you mind?"

Jess's enjoyed watching Oliver show her how to adjust the straps. Once the woman was satisfied, she left with her new purchase, and Jess clapped Oliver on the shoulder with a laugh.

"See? Perfect demo, as always!" she teased, watching his flustered expression with a sparkle in her eyes.

A bit later, a young man in his twenties came in looking for a collar and leash set. He asked for help and Jess wasted no time.

"Oliver, why don't you give him a demonstration of the collars we have?" Jess said. She took a soft leather collar from a nearby shelf and handed it to Oliver.

The young man watched, as Oliver showed him the features of the collar, demonstrating the buckle and pointing out the reinforced leash clip. Jess chimed in with helpful comments, and before long, she was holding the leash, giving it a playful tug that brought a flush to Oliver's cheeks.