Let the punishment fit the crime

"You see, Cassidy, this is the second time you've displeased me." She stared down at him with a stern look as she scolded him, the intensity of her displeasure making him wilt in front of her. "I think I must have been too easy on you last time."

He shivered at the idea of a more thorough punishment than last time, though he hadn't expected to get spanked when he came into her office, it ended up thrilling him in ways that he anticipated. Something about her firm hands roaming over his ass and making him cry out triggered something inside of him he couldn't explain, the feeling of being completely powerless and at Jana's mercy had been so incredibly arousing. Not to mention what happened afterwards, his memories of her so thoroughly fucking him made his tired cock begin to perk up, eager for the pleasure that it knew Jana could provide.

"Strip for me, Cassidy."

Cassidy instinctively began following her orders, the insistence in her voice signalling that she wouldn't suffer any defiance. He gripped his shirt in both hands and slowly lifted it up over his head, trying to provide the woman with a sultry show as he freed his already achingly stiff nipples to be teased by the cold office air. If Jana had any reaction to the strip show going on in front of her she didn't show it, she remained completely stoic, her gaze impartial and not revealing any of her emotions. Cass just continued undressing, this time wriggling the tight hot pants he was wearing down over his wide hips, leaving him standing naked in front of her, his cock standing achingly erect and coated in his own thin cum.

"Place your hands on the table now, Cassidy."

He did as she said and wasn't surprised this time as he heard a metallic click and felt the bracelets lock into place, Jana went and opened up a cabinet behind the desk, revealing an assortment of bondage gear, the inside was lined with different toys, whips, gags, blindfolds and the like. Cass shivered, not at all from the cold, his mind racing wondering what she was going to do with him. He saw as she selected a fine black silk blindfold, taking it in one hand and moving forward to gently wrap it around his eyes, tying it behind the back of his head and fully obscuring his sight.

"Let the punishment fit the crime," Jana said, her voice startling him slightly and making him jump now that he could no longer see her. "Are you familiar with that phrase, Cassidy?"

"No, Maam." He shook his head as if that could emphasize his confusion.

"Well, Cassidy, those words were written by Cicero, a great roman Praetor a long time ago." Cassidy could make out that she was moving by the sound of her voice, but the fact that he couldn't tell what she was doing made his stomach flutter in anticipation, she could be doing anything to his body and he'd have absolutely no way of knowing. "It is the key concept of retributive justice, something that I must admit I am quite fond of."

Cassidy wasn't entirely sure what the history lesson was meant to be teaching him, it's possible that he had learnt about this in school but if he had he had entirely forgotten it by now. He heard her fiddling with something in the cabinet and then approaching again, shrieking when she ran her fingers down his spine and gave his ass a light slap that sent it jiggling, not hard enough to be painful but stern enough to surprise him. One hand then gripped him by his hair and raised his head from where it had been laying on the desk.

"Open your mouth."

He did so, instantly feeling her fingers invading his mouth, reaching in to stroke his tongue letting him suck away and worship at each digit in turn before pulling out and wiping her hand off on his cheek, the saliva instantly cooling on his skin. The hand then returned, this time jamming something into his mouth, it took him a second to realize that she was gagging him but he neither tried to nor wanted to fight against it, he eagerly bit down around the ball in his mouth, his saliva already welling up from around his lips as she secured it in place.

"You seem to have an issue with seeking pleasure, Cassidy." She said, her hand releasing his hair and letting his head droop back down onto the desk. "First that little show you made for the cameras and now tonight letting yourself be seduced by a club-goer."

He tried to yelp but it came out as a muffled sound around the ball clenched in between his teeth as her saliva soaked hand slid down between his ass cheeks, quickly clenching onto the base of the toy shoved deep inside of him and gently applying pressure. His cock trembled at the movement of the plug, as it pressed down intensely into his prostate, the motion sending flushes of white hot pleasure throughout his body. She then wrapped her fingers around the base and began slowly attempting to pull it out, Cassidy's ass unwilling to let the invader go, clenching tightly around it and stopping it from sliding out easily.

"You're too busy thinking with that little cock of yours." She says as she continues easing out the toy, it's movements impeded by his clamping sphincter, **** to keep the toy trapped inside his writhing guts. One hand held him easily pinned down to the desk as she applied more and more pressure to the plug, his rosebud stretching out blissfully around the thickening part of the toy, his prick bouncing with excitement as his asshole was spread out once again by the thickest part. His sphincter spasmed around the toy currently stretching him out, the muscle tightening over and over trying to either expel it or suck it back in, but Jana's fingers are firm in their grip, holding the toy perfectly still.

"And this tight little ass." She punctuates the last word by yanking out the toy, his asshole suddenly feeling incredibly empty, clenching down around nothing, despite everything having grown used to having the hefty plug filling him up.

"I think it's time that you learned how to better deal with your urges Cassidy, and I'm going to help you do just that."