The Price of Losing

A nice reward

Once they arrived home, Jess turned to him with a playful, expectant smile. "Alright, Oliver," she said, placing her bag down with a slight flourish. "Strip down except for your panties, and get started on dinner. I'm going to go change into something a little more... comfortable."

As he worked, chopping vegetables and starting the stove, he could hear Jess moving in the bedroom. The sound of her closet door opening, fabric rustling, and soft footsteps heightened the thrill of the moment. His mind drifted, picturing what she might be changing into, but he refocused on cooking, trying to make the meal perfect.

After a few minutes, he heard Jess's footsteps approaching.

As Jess walked back into the kitchen, Oliver turned, and his breath caught for a moment. She was wearing an oversized sweater that hung just low enough to graze the tops of her thighs, with no pants in sight. She was wearing the collar where she kept her keys also, makign sure it was visible for him. The casual, comfortable look somehow made her even more alluring, and the flash of her bare legs as she moved was nothing short of captivating.

She leaned against the counter, watching him cook with a slight smile playing on her lips. Her hair was a little tousled, and her relaxed expression had a kind of effortless beauty that made his heart beat just a bit faster. To him, she looked gorgeous—more so than he'd ever seen her, in her own space and clearly feeling at ease.

"Smells good in here," she remarked, casting an approving glance at the progress he'd made on dinner. Her gaze drifted over him, taking in his naked form with a hint of satisfaction. "You're doing well, Oliver." And she gave him a kiss on the cheek.

He swallowed, feeling a mix of pride and nerves. "Thanks, Jess. I just want to make sure it's perfect."

She gave him a small nod, then tilted her head slightly, her smile widening. "I like you like this, you know. Right where I can see you, pleasing me and doing such a good job."

Her words made him feel both a little embarrassed and, in some way, incredibly fulfilled.

As Oliver finished preparing dinner, he carefully plated everything, making sure each dish looked just right. He set the plates on the small dining table, trying not to let his nerves show. Jess had settled into her seat, looking pleased, her oversized sweater draped over her in a way that only seemed to make her look more inviting. She glanced at the meal with an smile.

"Looks amazing," she said, reaching for her fork.

They ate in silence for a while, occasionally sharing little smiles and glances. Oliver couldn't help but feel that everything felt strangely... right. The candlelight cast a soft glow, and he found himself more relaxed than he'd felt all day.

After a few bites, Jess looked at him thoughtfully, setting her fork down. "You know," she began warmly, "I have to say—you've handled all of this remarkably well. Not many would have managed to get through everything with as much grace as you did." Her gaze softened as she added, "And I think that's what has really caught my attention."

Oliver smiled and took another bite to hide his expression. "Well, at the beginning, it was definitely annoying," he replied. "But I won't lie, at some point, I started to enjoy it, even though I tried to convince myself I didn't."

Jess leaned forward, resting her chin on her hand. "I could tell," she said with a playful smile. "Even when you were trying so hard to resist, there was something in your eyes that gave you away. I think a part of you was curious from the start."

Oliver felt his cheeks warm as he looked down at his plate. "Maybe," he admitted. "I guess there's something... freeing about letting go of control. Trusting you like that."

"I'm glad to hear that," she said warmly. "Because, believe it or not, I feel a responsibility to make sure this is enjoyable for you too. That it's something we both look forward to."

"It's definitely been... different," he replied with a shy smile. "But in a good way."

Jess laughed softly and gave his hand a squeeze. "Different can be exactly what we need sometimes," she said. "And as long as you're here for it, I'll make sure it's a good kind of different."

They finished dinner with a comfortable silence settling over them, the air between them charged but content. Once the plates were cleared, Jess looked over her shoulder with a mischievous glint.

"So, think you're ready for a bit more tonight?" she asked, arching an eyebrow.

Oliver's heart quickened as he nodded, feeling more ready than he'd ever been.

"Then follow me," she said, taking Oliver's hand.

He followed Jess into her room, where she guided him gently onto the bed. Slowly, she began to undress, letting each piece of clothing slip away until she stood before him, entirely bare.

She climbed onto the bed, positioning herself above him, her eyes gleaming with playful command. "Get to work," she instructed, her voice soft but firm.

Obeying her, Oliver began to kiss and pleasure her, savoring the moment and the taste of her pussy. Jess, enjoying his attention, reached down to trace her fingers over his caged form, sending waves of sensation through him. The teasing touch only heightened his focus, leaving him feeling both completely at her mercy and completely captivated. 

Oliver lost count of how many orgasms he had managed to bring her, but his tongue was starting to ache.

"Okay, that's enough. You've done a good job," she said, finally stepping away from him.

"I'm going to unlock you and let you cum, but I won't touch you. Getting a blowjob, handjob, or even fucking with me is something you'll need to keep earning," she teased, reaching for the keys hanging from her collar.

With a flick of her wrist, she took the cage and unlocked it, freeing Oliver's cock for the first time since they began their new relationship.

"Okay, you can start masturbating. But look at me while you do it," she instructed, stepping over him so that her pussy hovered close to his erection, but not quite touching it.

Oliver began to stroke himself, and within moments, he  cummed.

"Wow, you were kind of horny, weren't you?" Jess remarked with a playful grin, watching him intently.

"You see, good job pays well," she said, dipping her finger into the cum that had dripped from his tip and licking it off with a satisfied smile.

"Okay, clean this up and let's go to sleep. I need to rest," she ordered him.

"And what about the cage, Jess?" Oliver asked, confused.

"The cage? Oh, don't worry. I think you've earned a free night. Consider yourself lucky; it's not going to happen often," she said with a wink.

"Oh, wait. A new rule," she added before Oliver could move to do as instructed. "I'm not Jess anymore when we're in private. You must address me as Goddess or Mistress from now on."

"Understood, Mistress," Oliver replied as he moved to clean everything up.

Once Oliver had finished, they both climbed into bed. Jess leaned over and gave Oliver a gentle goodnight kiss on the lips before turning away to settle into her side of the bed.

They both felt asleep almost instantly as this days were being so intense.