What of Sissy Jenny

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The pride that engulfed him, when getting dropped off to work by Mistress Vicky and his slavemate, quickly melted away once he started approaching the entrance to his workplace. The heavy chastity anchored his penis to his padded prison. Each step had a crinkle effect, and that toyed with Jimmy's mind. Honestly though, if he didn't have the chastity cage on, no doubt he would be rock hard. He enjoyed humiliation. Jimmy liked to be a sissy for his Queen. It was the first time diapers were brought into the act. That, he had Max to thank for.

Max was Vicky's favorite slave. Who wouldn't want a gourmet chef at their disposal. Not to mention Max had the biggest member out of the four men. So yeah, Max got what he wanted. Max was pretty much a switch and did, from time to time, have permission to dominate Jimmy and the other slaves. So why did Jimmy have Max to thank for being diapered? Max liked seeing others wear diapers. He needed to feel above the other slaves. He never let his ego run too wild to try and challenge Vicky, but he was the superior male of the household. Diapers was a statement of ranking.
Jimmy recalled when Casey was the first to be diapered. It was a Sunday, so by then each slave was accounted for. Casey had spilled orange juice all over Mistress Vicky at lunch. Vicky was outraged, having worn white. She was so outraged, she couldn't even think straight. So, she demanded punishment ideas from Max. Max was quick to recommend diapers. Casey begged and pleaded. Mistress just smiled, a quite devilish grin. Casey had more than let Vicky know his displeasure in the idea, so it was going to happen.
"Quite fitting for a man with a small dick!" she snarled. She looked at Max and nodded. Max went out to his car and brought back the package of diapers.
"Diaper him," commanded Mistress.
Max tackled Casey down and ripped off his clothes with Jimmy and Dave to look on. Casey sobbed, after a quick defeat, as Max made a show of slowly pulling a diaper out from the package.
"No, Please no." Casey wept.
Max unfolded the diaper and snatched up Casey's ankles in order to lift Casey's ass up. Max slid the diaper under. Casey's small cries echoed in the living room. Max let Casey's legs down and brought the front of the diaper through. Then finally, taped the diaper up snug.
"What do you have to say Baby Casey?"
Casey lifted his head to meet eye contact with Vicky.
"I am sorry for spilling juice all over your perfect outfit. I deserve this.'
"And...."
Casey turned his head to his tormentor. "Thank you for diapering me Max."
"I think you owe Max a little more than gratitude. He did save you from having your ass tore up, instead he just wrapped your ass in a diaper."
Max rose to his feet and dropped his pants. Casey got onto his knees and slipped Max's giant cock into his mouth. It was evident Max had enjoyed diapering the little guy, because it quickly became Max violently thrusting and chocking Casey's mouth and throat. Casey was knocked off balance at first, but Max grabbed Casey by the head and just continued to slam his dominance into a frightened and diapered slave. Casey trembled as Max and Vicky went to the bedroom to change.
That was the first diaper experience and since then Casey has been in and out of diapers. Now, Jimmy is wearing one. A sissy diaper. Something new. Casey was always in just plain white disposable adult diapers. Jimmy is having to wear sissy girly-printed adult diapers? So, what does that mean is going to happen? Jimmy had been wearing panties and thongs for months. it was just worn under his clothes. These diapers, though, were too bulky. he would have to buy loose pants or something.
Jimmy could not focus on work. he was always aware of what he was wearing, so he did his best to avoid everyone, but it seemed like just the opposite happened. Almost everybody needed assistance. Eventually though, the work day was over.
Jimmy got into the car with Max and Vicky and it was there, in the parking lot that Jimmy was left. Because there was no more Jimmy, it was now Sissy Jenny. Jenny had no idea what awaited for him. He could tell Max knew his predicament from the obnoxious grin Max wore. it was Friday and the weekend was unclear for Jenny. what was going to happen to Jenny through the hands of Mistress Vicky, sidekick Max, and possibly the other two slaves? What of Sissy Jenny?

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⏰ Last updated: Sep 18, 2021 ⏰

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