Miss Jameson gives Deedee the plan

Later that day in Chloe’s office, Deedee stood rigidly in front of his boss. Sitting in the chair that Deedee used to occupy back when he was Derek, Chloe Jameson stared down at her secretary with anger flashing behind her eyes. “What the fuck Deedee? You have been useless all goddamn day. I thought we were through with this bullshit.” Standing up from the office chair and walking around the desk, Chloe’s lithe form was covered in a striking blue women’s pants suit. Her own sensible three inch heels left her a few inches shorter than Deedee, but it was clear that Chloe was in charge.

It took everything in Deedee’s power not to flinch. Miss Jameson was correct that he had been useless all day. The altercation with Trent that morning had taken over his mind as he attempted to work through the day. The anger that had allowed him to stand up to his son after not standing up to another person for almost a year was now making him hesitate when given commands. Actions that should have been as automatic as breathing now required thought. It wasn’t just that his anger permeated his mind, but that for the first time in months he was questioning who he was again.

“I am sorry Miss Jameson. I know there is no excuse for my actions and I submit myself to any punishments you might think up.” A deep breath, or as deep a breath as his recently tightened corset would allow, allowed for a pause before Deedee continued. “I had an altercation this morning. My son Trent came home and found me leaving for work. I know it doesn’t excuse my actions, but I wanted you to understand why I have not been as attentive as I should be.” The feeling of dropping the problem off in Chloe’s capable hands was like a weight being lifted off of his chest.

That caught Chloe off guard. Trent and Chloe’s interactions in the past had only helped Chloe with the decision to feminize his father. The only way a person could garner the kind of hatred, misogyny, and self grandeur that Trent displayed was through training or example. Her original thoughts were that Deedee’s old self was the most likely culprit, but learning more and more about her secretary, Chloe surmised that Trent had likely picked it up elsewhere. While Deedee’s parenting could never be called good. It was more because he was an absentee father, spending all of his time at work. The fact that Trent’s mother had divorced Derek years ago and had subsequently abandoned Trent likely also led to the boy’s hatred of women. “I’m sure that didn’t go well.”

A chuckle that sounded more like Derek then Deedee came from the perfectly painted lips on Deedee’s face. “That is the understatement of the year. He came in and started throwing slurs and hateful comments. Not only that, but apparently he dropped out of school! What the fuck am I going to do with him?” The outburst stunk of who Deedee had been before.

The eyebrows on Chloe’s face ratcheted up with each line that came from Deedee’s mouth. Her own lips quirked into a wry grin as she responded. “Deedee, I understand you are dealing with something very stressful. But I swear to god, if you don’t turn back into the simpering sissy slut I trained you to be, I’m going to strip you naked and make you walk home with a cock in each hole.” The threat was said with almost no malice, but the words carried a steel to them that was undeniable.

Deedee’s tongue flicked out to nervously lick her pillowy soft lips. Her response, while not as instant as it should have been, was still spoken as softly as it should have been “Yes Miss Jameson.” Closing her eyes for a moment the secretary concentrated for a moment before taking another breath. As her eyes opened, there was a softness to them that had been absent. “Again, I apologize ma’am.” Deedee swiftly crossed the room to the side of Chloe’s desk. Moving her heeled feet to shoulder width apart, she bent at the waist and placed her palms flat against the expensive oak desk. This put her body in a perfect position. Her back arched and her prominent ass was on full display. The hem of her very short skirt rode up and showed the bottoms of both cheeks as she turned to her mistress.

Nodding to herself, Chloe stood up and moved around behind Deedee. Her hands trailed along the hem of the shirt skirt, her nails just grazing the soft sensitive skin of Deedee’s ass. A soft mue of contentment came from Chloe as she took hold of the skirt and pulled it up even higher to fully expose the round ass of her toy. Reaching down into a drawer, Chloe pulled out a large plug. Unplugging it from the USB charger it was attached to, she reached up and without warning pushed it past Deedee’s lips and into her mouth. Chloe’s voice was husky with lust as her words of warning came out.“That is the only lube you are getting.”

Feeling Chloe’s hands on her body, Deedee began to stiffen. Not her posture, that was already rigid and locked in place to show off her assets. No, the cock hidden in the tiny panties began to come to life even as she wished it wouldn’t. Trepidation filled Deedee’s eyes as she wondered what the punishment for the day would be.

Chloe’s fingers reached into the same drawer and extracted a tiny blue pill. Reaching up and pulling the plug out, she swiftly pushed the blue pill into Deedee’s mouth. “Swallow.” Deedee couldn’t help but to follow the simple command as she did her best to please her mistress. Taking the barely lubed up plug in her hand Chloe pulled the beautiful expensive lacy panties to the side and slowly began to push the head of the plug into Deedee’s ass. The bulbous plug pushed against Deedee’s hole for only a moment before the instinct and training took over. The plug slipped into place quickly.

Chloe stepped away from the exposed ass of her secretary and sat back in her chair. “In light of your issues at home, I will only punish you with a few things today. First, your plug will be in and vibrating until you get home. I will keep it low, I don’t want you cumming from your favorite toy. Second, I just slipped you 100mg of Viagra. So, seeing as we have 2 hours left in the day, by the time you get home you should be nice and ready for whatever happens. Now, I have a third present for you. I’m going to give you something that very few sissy’s in your position ever get. You have proven to me that you have accepted your new role in this office, but I also know that you hate it. So, here is your newest, and biggest gift. I will no longer require you to be my little sissy outside of the office. Now, that doesn’t mean you can go back to being a man. I think we both know that ship has sailed.” The last sentence was punctuated by a moan that Deedee could not keep in as Chloe spiked the vibrations of the bluetooth plug. “But it does mean that I think you will be able to find a better solution to your Trent problem than just kicking him out.” Turning away from her secretary, Chloe began to type away at her keyboard, returning to her job.

“Go back to work slut. Justin from MegaCorp will be here to sign those papers at 4, and I expect you to continue to provide your particular flavor of customer service to him still.” With that dismissal, Deedee finally stood up and walked towards the door to the office. Only as she reached the door did she pull her skirt back down over her bouncy ass. “Thank you Miss Jameson. I will be sure to be ready for that meeting.”

Sitting down at the much smaller and cheaper desk out in front of the office, Deedee crossed her legs tightly in an attempt to keep her cock from pushing out against the very short skirt she had on. The constant low vibrations of the plug coursed through her body as she sat there, her weight pushing it deeper into her body. Through her lust addled mind, Deedee wasn’t sure what Chloe had meant, but she knew better than to question her at that time. As she tried to puzzle it out, an email from her boss popped up on her screen.The confused look on Deedee’s face slowly morphed as she read the email. Each line brought more pleasure and a bigger grin to her face. Her mistress had anticipated her not understanding the subtle line as they parted, and had sent exactly what Deedee would need to take care of the situation.