Bad Boss Pt. 04-05

Author's Note: There is no same sex activity in this segment. It is in the "Gay Male" category because of other portions of the story.

Part IV: The Ghosts of Transgressions Past: Tracy the Intern (Part I)

That Monday night, after my first day back at work, I was in a dark place. My employees, whom I'd previously exercised complete and appropriate authority over, now had me under their thumbs. I was theirs to control. I didn't manage them anymore; they managed me,

I couldn't bring myself to eat anything for dinner. I turned on the television, trying to distract myself from my woes—to no avail. I wound up drinking myself into a stupor and falling asleep on the couch.

It wasn't a restful sleep. I woke up about 4:30 am with a throbbing headache and a foul taste in my mouth.

I got up, took some aspirin, stripped off my clothes, and flopped into my bed, hoping to get a few more hours of sleep before facing another day of humiliation at work.

No luck on that, though. I decided to go to work early to avoid having to walk past the others. That plan worked fine. I was in my office with the door closed before anyone but the custodian was there. Unfortunately, that didn't mean I had avoided being humiliated and degraded for the day.

I looked at my office calendar and saw that Lori had scheduled a meeting for me with her and Phyllis at 9:00 am in my office. And, sure enough, promptly at 9:00, there was a knock on my door. I didn't have the option of ignoring it. They had me by the balls, so to speak.

"We want to talk with you about last Friday night," Lori said, taking control of our meeting immediately.

"What's there to talk about?" I asked defensively.

"You see, that's the problem," Phyllis responded. "You don't think there's anything to talk about. But there is." She paused. "What there is to talk about is why last Friday night was necessary—what you did to make it necessary."

"It's not like we had no reason to orchestrate last Friday night's activities," Lori chimed in. "We had our grievances."

"Yes," I said, "and you made them known at yesterday's 'meeting'. You made them known and you addressed them all."

"That's where you're wrong, Mr. Simmons." It was Lori again. "We addressed the horrible company policies you imposed on us but we barely scratched the surface of your horrible, disgusting conduct—what really prompted us to provide you with last Friday's adventure."

"You're going to have some lessons in how not to be a vile, disgusting creep," Phyllis said, spitting out the words.

"And lesson one," Lori continued, "starts right now." They were working like a tag team, passing back and forth the opportunity to manage me.

I braced myself, thinking I was ready for whatever was in store for me. I wasn't.

"Remember Tracy?" I didn't, but Lori went on quickly anyway. "Oh, sure you do ... the 18-year-old student who tried to do the internship her high school required here."

"Oh, yeah," I recalled. "She quit before she finished, right?"

"Oh, that's right. She quit! Do you have any idea why?"

"She told me she didn't think the internship was a good fit."

"So you think that was it?" I knew there was more to it but I wasn't going to introduce evidence against myself.

Lori continued. "You don't think she quit because you kept probing her about her social life: 'Do you have a boyfriend?' 'I'll bet you're popular with the boys,' 'Did you have a hot date last weekend?' and things like that. Do you think that might have contributed to her decision?"

Probably, but I didn't answer.

Phyllis chimed in, "That would have been bad enough—actionable if Tracy had felt she could pursue it. But what you did was much worse." I waited for the second shoe to drop. "You asked her if she found older men attractive and whether she'd ever dated an older, experienced man." she paused. "Do you think that's okay?"

"I guess not," I mumbled.

"Oh, and that wasn't the worst, and you know it!" The third shoe was about to drop. Third shoe"?! What the fuck? Is that even a thing? Turns out it is.

"What finally triggered her decision to leave was when you called her into your office and had a porn video running on your computer—a porn video showing a young-looking woman with a middle-aged man. She couldn't see that until you motioned her to come around the desk to take a folder from you. And, when she did that, what else did she see?"

Boy, I really didn't want to answer that. Lori didn't wait long before jumping in. "You had your dick out of your pants, sticking up hard."

"You sick fuck!" Lori said. "How could you do that to her!" No answer was expected or offered.

"So, we have a remedial training program that we're beginning today." Phyllis began opening a box she'd brought in with her and Lori continued, "Stand up and drop your drawers ... NOW!"

I knew what was at stake if I refused; I complied. "Underpants, too, you creep!"

Lori ordered me to pull up my shirt so, there I was, exposed to my two tormentors. And the nature of their torture was becoming clear. Phyllis was pulling a steel cock cage out of the box. And it was one of those cages with tiny spikes on the inside—spikes that would quickly punish even a small step toward an erection.

"You're not putting that on me!" I asserted, as if I had any say in the matter.

"No, you're going to put it on you! And you're going to do it right now."

I didn't have a choice but, if it had been up to me, it was probably the smarter decision to do it myself. If Phyllis or Lori were to push my cock into that thing, I might feel the pain of those barbs right away.

So, I took the device from Phyllis and fastened the ring around my cock and balls. They insisted that I fasten it as tightly as possible, making it unlikely that I could somehow wiggle out of it. I pushed my limp dick into the sleeve and Phyllis locked the device tightly.

"Let's make sure this works," Phyllis said as she began running her nails over my thighs. She was bending over and I realized for the first time that her blouse was unbuttoned more than normal. I could see the tops of her young breasts. I could smell her scent. When she moved her fingernails up to my chest and began dragging them across my nipples, my nipples weren't the only thing that began hardening.

The pleasure of Phyllis's touch was immediately accompanied by a sharp pain in my cock as it began pressing against the spikes in the cock cage.

"Owww! God damn it! Stop!" I complained. "This is torture."

"It works," Phyllis crowed as she backed away from me.

"You can pull your pants up now," Lori instructed. "You'll wear this every day—putting it on first thing in the morning and we'll unlock it at the end of the day."

Thank God! I thought. If they made me wear this at night, I'd wake up in pain every time I got a nighttime woody.

"Phyllis has devised a schedule of exercises for you to help you separate work from your perverted pleasures."

What the fuck was this? What else had they cooked up to torture me? I didn't have to wait to find out.

"Terrell has installed several cameras in your office—discreetly, of course. No one will notice them. But I'll show you where they are."

Lori got up and pointed to one that was just peeking out above a picture frame on the wall behind her, pointing directly toward my desk. She indicated one that was on a shelf next to my desk, pointing down on the desk area. And there was a third one, behind my desk that would show me from behind and the rest of my office area.

"As you can see, we can see everything you do in here."

"Okay, I get it," I said. "No porn at the office, right?"

"Well, isn't that what one would think," Lori responded. "But, no, that's not what our neuropsychologist recommends."

Damn Phyllis and her fucking science background. Hadn't it already been used against me enough?

"No, Phyllis says that if we need to use operant conditioning to get you to change your disgusting habits. Do you know what operant conditioning is?"

I had some idea but that didn't stop Lori from going on. I think she was enjoying laying out what would happen to me.

"It means that your behavior will be changed by rewards and punishments. You need immediate feedback for both good and bad behavior. Your punishment ... well, you've already experienced it a little when Phyllis was testing the device. Your reward for good behavior is ... well, it's just no punishment."

"The bad news for you is that there has to be punishment. The good news is that you get to watch porn at the office. In fact, you have to watch porn. And here's the porn you have to watch." She handed me a USB stick.

"You'll watch that three times a day," Lori ordered. I've put it on your schedule as 'Executive Time - Do Not Disturb'. Don't worry. I'll make sure nothing interferes with your Executive Time." She shot me an obnoxious smirk.

"And remember, Vic," Phyllis chimed in. "We'll be watching. You'll do your Executive Time with your pants and underwear down past your knees and your shirt unbuttoned and pulled aside. We need to monitor your progress closely."

Shit. These creeps thought I was a pervert. But they were the ones planning to watch me resist the sexual torture they'd set up.

"As you start to make progress," our neuroscience expert continued, "we might have to add additional stimulus to ensure that the operant conditioning is highly effective. But we can discuss that later."

Part V: The Ghosts of Transgressions Past: Tracy the Intern (Part II)

My "training" began that very day during what should have been part of my lunch hour. Lori called to remind me of the conditions. I knew who was holding the high cards here. I didn't try to protest. Uncomfortable as it was for me, I pushed my pants and boxers down past my knees, unbuttoned and pushed open my shirt and sat down, knowing I was exposed to at least Lori and Phyllis—God only knows who else might be watching.

I put the USB stick in my computer and saw that the MP4 files were all neatly dated: morning, midday, and afternoon for every day for the next three weeks. Three fucking weeks!

I knew what to do. I fired up the first file, which was labeled for midday today. I wasn't surprised by the content. Not only was it a scene with an older guy and a young woman—clearly over 18 for legal reasons but not looking more than a day over that—it was the very same video that I'd used with my little trick on Tracy.

And it was a good one: gorgeous, shy, reluctant teen, seduced by a slightly overweight, average-looking guy in his 50s. Like that happens all the time! Fantasy or not, it was hot!

He unbuttons her blouse and unfastens her bra, to expose her small, perfectly shaped breasts, with prominent nipples that respond to his touch.

I could feel my cock hardening and, then, the sudden, sharp pain that resulted from that. I tried to focus on something other than the video and, gradually my hardon receded and, with it, the pain.

But I knew where the video was going. And I knew that it would make me hard and cause me excruciating pain. So I looked away.

My tormentors were having none of that. I got a call from Lori's phone, but it was Phyllis who was on the line.

"No! No! You will not look away from the video. That's the whole point of your training." I knew that, of course. "If you look away, we'll have to consider that a failed training session and add more sessions to make up for it. Do you understand?"

I did. I looked back at the video, trying not to get hard. That works about as well as trying to will an erection.

Now the girl was completely undressed and the old guy was fingering and licking her cunt and clitoris. Of course, she was acting like she'd never been sexually aroused before—like he was opening a whole new world for her. And, as often happens in these scenarios, it transformed an innocent teen into a cock-hungry slut.

It's the girl who, after experiencing a crashing orgasm—the viewer is invited to think that it's the first she's ever experienced—gets down on her knees and pulls out the old guy's cock because she sooooo needs to suck it.

All fake—preposterously so—but it worked. Shit, did it work!

My cock was rapidly hardening, causing me extreme pain, which caused my cock to flag. But I saw this gorgeous girl, sucking this guy's cock, devouring his cock, eager for his cum and I couldn't help but get hard again, causing a horrible cycle.

It didn't help that I'd watched this very video and fantasized about me being the old guy and Tracy, the young intern, being the girl. When those images flashed through my mind, my cock swelled, again causing a wave of pain to radiate from my cock.

Finally, my 15 minutes of hell were up. I could get dressed and get back to work. I was still painfully aware of the spiked chastity device encasing my cock. I wasn't looking forward to the late afternoon "training session." But I had to admit, it looked like Phyllis's operant conditioning would be likely to work. Every time I began to feel the pleasure of sexual arousal by watching the video, I was immediately subjected to the punishment. And, after the 15 minutes of experiencing that, the absence of pain did feel like a reward.