A surprisingly gentle awakening

Cass drifted back into consciousness in a far more comfortable setting than where had fallen asleep in, waking up in strange and surprisingly comfortable places was swiftly becoming a familiar sensation for him. Cracking his eyes open, the sight of Jana's deep brown hair wrapped around her sleeping beautiful face met him, he was cuddled up against her, playing the little spoon to Jana's big spoon. Just staring at her took his breath away and his heart skip a beat, she was the most beautiful woman he had ever seen and the idea that she was interested in him was overwhelming. Everything about her was overwhelming just the scent of her was intoxicating, a mix of her perfume, her sweat and beneath that the traces of semen, hinting to the lewd activities they had gotten up to last night.

Remembering last night he began to piece together what had happened from the fragments of his memories, he blushed a little remembering the way he had been fucked over and over again on the desk, cumming his brains out until he collapsed into a quivering mess, luckily Jana had been kind enough to stop the toys from vibrating after he had passed out though she hadn't removed them right away. He remembers laying their twitching on the desk, his body still occasionally shaking from the intense orgasms he had gone through while lapsing in and out of consciousness, he occasionally heard their voices but was far too delirious to understand the words they were saying.

Eventually he remembers being untied from the desk, picked up by strong yet gentle hands and rolled up in a blanket, the sensation reminded him of when he was a child and had fallen asleep on the couch and his parents had brought him to bed, though this time he had several loads of cum dripping out of his asshole. He was carried delicately down to where a limo picked them up and then his head rested in Jana's lap, Molly sat across from them in the car, her hands mussing his hair gently or softly stroking at his sweaty brow. It was surprisingly tranquil after the intensity of their fuck-session but he knew that his body couldn't have handled any thing more after being put through the wringer like that.

Most of his memories are fragmented, interrupted by periods of blissful sleep, riding in the limo, being brought inside a house, where he was changed into pajamas and then getting into bed with Jana where he swiftly fell asleep, whatever had happened to Molly he didn't know. This was how he had gotten here though, he lifted up the blankets and looked down at himself, he was wearing a silk blue set of pajamas that probably cost more than any other pair of clothing he had ever own and somehow they fit him absolutely perfectly. He couldn't help but notice Jana's figure wrapped around his, a matching set of pajamas wrapped around her gorgeous frame and the bulge of her cock in her pants already swelling and showing off, it seemed like despite their activities last night it left no respite from morning wood.

Jana stirred awake at the movement of the blanket, deep blue eyes opening to regard him.

“Good morning, Cassidy” She murmured, her voice husky and breathless from overuse, just hearing her voice making his heart do flips in his chest.

Cass groaned in response, far too embarrassed to say something, stuffing his face into the pillow to avoid meeting her gaze.

"What's wrong, my little pet?" Jana asked, the concern in her voice genuine.

Cass groaned again, keeping his face buried into the pillow.

"Cassidy, you're worrying me, if something's wrong-" A hand had reached out to gently shake him, trying to get a response.

She cut off when he poked his head out from behind the pillow. "I just..." He said, still refusing to meet her eyes but no longer hiding his face. "I don't get it."

"Don't get what?" She responded, a look of slight confusion coming over her features, one eyebrow arching up in question.

"Why me?" He said, his voice was low and whiny, sounding petulant even to himself. "Why do all this for me?"

"Oh, Cassidy." She sighed, the tension going out of her limbs as she wrapped him up in a smothering hug. "Would you believe if I didn't want it to go like this?"

Cassidy's face drops at that information, already looking like he's on the edge of tears.

"No not like that..." Jana continues. "There's something I need to talk to you about. I guess I better start from the beginning, ever since you started at the club I couldn't take my eyes off of you, that slender cute body of yours, your adorable attitude, everything about you drew me to you and I knew that I had to have you. But then I think I went too far, that first day with the spanking and everything that happened after, I shouldn't have done that. Then afterwards I got so caught up with everything, getting you to do whatever I wanted, treating you like my pet, it's not fair to you."

Cassidy listens to her explanation with rapt attention, words just pouring out of her, a stream of consciousness and for the first time Jana showing some amount of vulnerability, the idea that this strong capable woman thought she had done wrong was mind-boggling to him. More than anything seeing her like this was strange, she was normally so calculated, so purposeful and here she was pouring her heart out for him, it made him care even more about her than before. Cass couldn't say it in the moment but he really liked everything she did to him, the way she had used him for her own pleasure, submitting to her had made him feel good, being told what to do by a beautiful woman like Jana felt so natural, so right. He had to admit that her spanking him had been unexpected, and at first he had reacted with shock but he definitely didn't dislike it and then of course everything that happened after that? Her finger his ass and then fucking him, all the various ways that she had used him and marked him as hers, he definitely didn't dislike any of that much the opposite in fact.

"Cassidy, I feel terrible about all of this, forcing you into this situation without your consent, it was wrong of me and if you never want to see me again I'll understand." Jana continues, the vulnerability in her voice was new and unexpected to Cass from such a normally domineering woman. "If you just say the words then I will let you go, I will return to just being your boss and our relationship from here on will be purely professional, you won't nee-"

"No!" Cassidy interrupts her, shaking his head, pale cheeks flushing pink, the strength in his voice and his interruption startling them both, finally turning to meet her eyes. "I mean, no, I don't want that, Jana."

"Are you sure, Cassidy?" Jana says holding his gaze, his bright gray eyes twinkling and unwilling to look away from hers. "After everything I've done to you, you don't want to back out?"

"I'm sure." Cassidy nods, he had never been more sure of anything in his life in fact.

"Well, I suppose another option is for you to keep being my pet, we would need to define the rules and guidelines of our relationship of course..." Jana petered off, voice going quiet with the idea that he did want to be hers. "Is that what you want Cassidy? Do you want me to be your mistress?"