She wants to plug her toy up

Cass woke with a start. For a couple panicked seconds he had no idea where he was, his mind swiftly worked to remind him of what he had gone through and he blushed at the memories of Jana fucking him. He had given in so easily to her demands, surely he wasn't that easy to control? Though it did feel nice to have someone telling him what to do, so much less to worry about. He soon realized that he was still naked, he was covered with a luxurious light blanket that felt incredibly soft against his bare skin, knowing Jana's tastes he was sure it would've cost a fortune.

He was worried that he was soaking the blanket with the fluids from their lovemaking session but found that he didn't feel messy at all, instead he felt crisp and clean. He had been washed, there was not a speck of cum on his body, and not an ounce of sweat besides. Somehow despite the fact that he had been ass-fucked into submission the idea that Jana had cleaned him up as he slept made his face red with mortification. Thinking of Jana, he quickly became aware of a clicking sound coming from behind the desk, he looked over and Jana was typing away, looking just as perfect as she had when he first entered the office, not a single hair was out of place.

"Ahhh, Cassidy, I'm glad you're awake." Jana says when she notices him stirring, walking over to lay down a bundle of his clothes on the coffee table next to him, resting on top is another deep brown wooden box.

"I had your clothes cleaned while you were asleep, it wouldn't do to have you leaving my office in soiled garments." Jana states in an imperious tone, then gestures to the box on top. "I have a present for you before you go though."

Cass's mind was still hazy with sleep, his thoughts sluggish and his head still feeling dizzy, he watched as she opened up the box to reveal a silver butt plug resting on a fine red velvet interior. He stared at it briefly in confusion, not sure why she was showing him this... Eventually his brain caught up, she wanted him to use it!? His ass still felt sore from the reaming she had given him earlier, he didn't know if he was ready to put something in there so soon. He couldn't tear his eyes off of the plug, he wasn't unfamiliar with this kind of thing but he'd never tried with something quite so large, it was twice the size of the one he had at home, almost four inches long and half that in width.

"You see Cassidy, I like to leave my toys with a reminder of me, even when I'm not around." Jana explains as her piercing blue eyes pin him in place. "It would make me so very happy if you were to wear this, you want to make me happy don't you Cassidy?"

Cass felt like prey that had been cornered by a hungry predator, there was no way he could possibly refuse her. His mouth is too dry to make words so he responds with a nod of his head, an act which makes Jana beam happily, her eyes lighting up with joy at his acceptance, Cass figured that if he was going to be stuck doing things like this at least getting to see Jana's gorgeous smile would make things bearable.

"Wonderful Cassidy!" She exclaims, already reaching down to move him, lifting him up and then placing him back down over her lap as she sat down on the couch. Cass couldn't help but whimper in delight at the feeling of her warm hands on his skin, his breath catching in his throat as he's laid over her soft thighs, his prick aching, desperately excited but far too exhausted to become erect. Laid down like this he became aware of just how tender his asshole was, he wasn't sure how he was going to take the butt-plug but he knew that he would try his best for Jana's sake. He could see Jana getting the toy out of the box, she had brought over some of the cream she had used to soothe his ass after the spanking earlier and was spreading it over her fingers.

Cass lay as still as he could, but couldn't help a high-pitched yelp escaping from his lips as she slid one cream-covered finger around his sore rosebud. The cream felt cool and soothing, helping ease the pain as she gently rubbed it into his sensitive, twitching sphincter. He struggled not to moan or wriggle away as she delicately tended to his aching stinging hole, the lotion quickly taking effect and numbing the soreness wherever it was applied.

"You're such a good boy, Cassidy." Jana purred down at him in approval. "I'm going to put the plug in now, do not worry though, I will be as gentle as I can."

Her reassuring words did little to ease his anxiety, and his heart fluttered in his chest as she affectionately spread one cheek to line the plug up against his butt-hole. He knew that this would be intense, but he didn't know how to prepare himself for it, a hiss of breath coming out when he felt the silver slide between his cheeks. Jana had coated it with the lotion as well and it felt icy cold against his burning hot skin, the toy wasn't as big as Jana's cock but it was mercilessly hard and almost as thick as her member at it's widest part. There was a little pain as she pushed it forward, enough to bring tears to his eyes, his clenching rosebud fighting back valiantly against the invader.

"I know you can do it." Jana assures him as she applies more and more pressure, his tunnel gripping tightly around the largest part of the toy. "I know you can."

The stretching of his tender hole was blissful agony, his body tingling and aching as she gently eased the silver plug in and out, pushing it ever so slightly further into his clenching guts each time. If she hadn't so thoroughly wrung him out earlier, Cass was sure that he would've been orgasming again, instead he savored the sensation of it, the pain ebbing away to be replaced by the heat of arousal.

"It's almost in there." Jana whispers breathily down to him, her lust-filled voice encouraging him to take the rest of it inside. "It's so close."

"Oh... Fuck!" Cass moans out as the plug finally fully slipped into him, his sphincter clamping tightly around the thinner part near the base holding it firmly inside of him. He could feel it pressing hard into his prostate, each gentle movement sending tingling heat throughout his aching body.

"Such a good boy, I knew you could take it." Jana says proudly, her fingers still deftly teasing around the wide base of the plug. "Now, lets get you dressed up and on your way."

She lifted Cassidy up off her lap, his legs trembling and weak as the movement jostled the toy around inside him, his hole clenching tight around it. In a daze Cass just let her manhandle him as she dressed him, unable to focus on anything except the sensations coming from his ass. She adroitly dressed him, hands working hastily to drag his shorts back on and his shirt over his head, slipping on socks and shoes, it didn't take long before he was fully dressed before her, were it not for the plug in his ass he was much the same as when he had entered hours ago.

"Now Cassidy, I'm not an unreasonable woman, I don't expect you to keep that toy in all the time." Jana instructs him, her much larger frame towering over him. "I will allow you to take it out if you need, but I will be very disappointed if you don't wear it as often as you can."

Cass cowered slightly at the idea of her displeasure, his body still aware of what the price of her disapproval meant. He nodded, his mind still struggling to make sense of the situation it had ended up in, still unable to find the words for what was going on.

"Now Cassidy, I'm quite a busy woman and I have to return to work." She gave him a swat on the ass that rocked the plug inside of him sending a burst of pleasure flooding throughout his body at the motion. He felt like a newborn calf, struggling to walk as he made his way to the door, resting briefly for support before heading out from the office.

What time was it? Had the club already closed? Is he supposed to return to work with this toy making his every movement an excruciating delight? Cassidy doesn't really know what to think, closing the door behind him he spots Molly staring wide-eyed at him from behind her desk. There's no way that she heard everything that went on in there? His face goes beet-red in shame at the idea that this demure woman had heard him get so thoroughly fucked. He couldn't meet her eyes to notice how flushed she had gotten at his appearance before he stumbled away.