Bad Boss Pt. 06

Part VI: The Ghosts of Transgressions Past: Employee Benefits and Terrell's Complaint

The week progressed with more of Phyllis's training sessions—three times a day, pleasure leading immediately to pain for 15 minutes at a time, followed by relief at the session ending accompanied by dred about the next session.

At night, I was able to quench my frustrations. I would masturbate at least twice a night and once in the morning before going back to work and being subjected again to the torture my tormentors were inflicting on me. I hadn't whacked off this much since I was a teenager.

But the conditioning was changing how I jacked off. I'd always masturbated mostly while watching porn on the computer. But now I had to be very careful not to pick porn that was reminiscent of anything that Lori and Phyllis had used in their conditioning exercises. Since they'd focused mostly on porn with older men and younger women because of my supposed "sins" against Tracy, that sort of stuff was out. Worse, even porn involving younger, innocent-looking women called up memories of the pain I experienced in the training sessions.

I found myself turning to MILF porn and other porn focused on more mature women. So, instead of jacking off to nubile young women being introduced to sucking cock and getting fucked by older men, now the focus of my attention was on older, more voluptuous women. That was okay. It worked. That's what mattered. And I was thankful for the relief.

I harbored the hope that masturbating so much might make it harder for me to get an erection during the training sessions, sparing me some of the resulting pain. Alas, that didn't happen. Phyllis and Lori picked out porn that grabbed me at an unconscious level. They knew what they were doing.

If I wasn't getting hard and experiencing the pain of the spikes in the cock cage during a training session, I'd get a call on the intercom from either Lori or Phyllis—I guess whichever one was in charge of monitoring my session. They'd direct me to run my fingers up and down my thighs and to play with my nipples. I'd never really thought of my nipples as being an erogenous zone but, unfortunately for me, if the video alone wasn't getting me hard, this stimulation would often do the trick.

Checking my calendar Wednesday morning, I saw that Lori had put a meeting with Terrell on my calendar for mid-afternoon. The subject line said, ominously, "Employee Benefits." What the fuck! I had no say in this. I was wondering whether the humiliation and torture would ever end.

When 3:00 pm rolled around, right on schedule, there was a knock.

"Come." I immediately regretted responding to the knock in the way I had for years. Now the curt response held a different meeting.

Terrell came in and closed the door behind him.

"What do you want?" I said gruffly.

"Well, Vic, as you know, I'm flying to Kansas City to meet with a potential customer. I wanted to meet with you first to make sure I was ready for the trip—you know, relaxed and in a good mood."

The asshole thought he was being really clever; he was smirking like the cat who caught the canary.

"Let's get this over with," I said as if I had some control over the situation.

Terrell started to walk around the desk when a voice over the intercom interrupted.

"No, Terrell, stand where you are. Vic will come around and get on his knees to service you."

It was Phyllis.

"God damn it!" I blurted out. "Are you watching this?"

"Of course we are, Vic," said Lori. "We wouldn't miss this for the world."

Phyllis chimed in again, "And, before you get down on your knees to take care of Terrell, take off all of your clothes. That's very important."

Important for your vicarious pleasures, I thought. But I did as instructed.

It's humiliating enough for a straight man to be forced to suck a man's cock. But being required to strip naked in front of a fully clothed man you're being forced to suck off adds a whole new level of humiliation. It emphasizes the power differential by underscoring your vulnerability. And, of course, it didn't help that I was being forced to expose to Terrell that my cock was in a chastity device. The fact that he'd probably viewed some of my training sessions didn't make it any less embarrassing to expose myself like this.

But expose myself I did. Soon I was standing, completely naked in front of Terrell. I knew that the positioning gave several good views to my remote "trainers"—Lori and Phyllis, at least, and God knows who else could be watching.

"Now get on your knees," Lori ordered. "And, while you're doing this, think about the completely unjustified bad performance review you gave Terrell last time to 'justify' not giving him any raise. Think about why Terrell, who performed as well as anyone, was the only person to not get a raise."

Truth be told, Terrell probably did deserve a raise. I just didn't like him much. He was cocky and self-assured. It didn't help, in my book, that he was considered extremely hot and was probably the object of lots of our female employees' sexual fantasies. I just didn't like the guy. And I'm in charge of setting salaries; I'm the decider. So, he didn't get a raise. It's not like he's entitled to a specific salary.

But now I was getting on my knees to abase myself by sucking him off.

Terrell was beginning to unzip his pants but the disembodied voice of Phyllis interrupted.

"No, Terrell. Let Vick do that. He needs to show you that he wants to do this."

Wants to do this! What the fuck?! Everyone knew full well that I didn't want to do this—that I was being blackmailed into it.

Still, I reached up and unzipped Terrell's pants. I reached in and wrestled out his cock. Even soft, it was full and heavy. And it was beginning to harden quickly in my hand.

"This isn't to be a quickie, Vic," Phyllis said. "You need to make love to Terrell's cock. You need to kiss it and lick it and worship it. In fact, you need to undo us pants completely so you can have better access to the object of your veneration."

I unbuckled Terrell's belt, unfastened his pants, and pushed them and his boxers down below his knees.

Now I was staring at his huge ball sack and his cock that was rising fast. A random thought flashed through my mind: I might not have given Terrell a raise, but I'm sure giving him a rise! Maybe it would have been funny if I hadn't been the one naked on his knees getting ready to "worship" Terrell's cock.

"First," Phyllis instructed, "kiss his balls. They've been busy making millions of sperm cells that you're going to coax out of his cock with your mouth. You need to thank them in advance for their gift."

Shit! She was laying this on pretty thick. But I managed to bring myself to kiss Terrell's balls. My nose was filled with his musky scent. I guess it wasn't intrinsically disgusting but, in my situation, it maked me gag.

"Put your hand behind his ball sack and fondle those sweet balls.," Phyllis obviously enjoyed being the director of this perverted scene. "Now take each one gently in your mouth and massage them with your tongue."

I did it, holding back my impulse to throw up. Terrell's balls were warm and large, each one filling my mouth in turn.

"Now kiss them each again and run your tongue up from the base of his cock to the tip." The obvious relish in Phyllis's voice made me wonder how many times she'd fantasized doing exactly this with Terrell. Maybe she'd actually done it. Who knows what hook-ups happen between co-workers?

Terrell was now completely hard; his cock was standing up above a 90-degree angle. As I slid my tongue from the base of his shaft toward the tip, his cock twitched, especially when I hit the sensitive spot just behind the helmet.

"Kiss the tip gently and sweetly, showing him how much you love his cock."

Phyllis didn't really want me to show how much I loved Terrell's cock because that was not at all. Showing how much I really loved his cock would be finding a knife and cutting it off. But I knew the drill. I gently kissed the head of Terrell's cock, which was glistening with pre-cum now.

"Now, Vic, look up at Terrell and ask him if you can please suck his beautiful cock."

Shit! Really?! But I did it. It was surprisingly hard—even harder than all the other things I'd been forced to do—to look up to Terrell, who was looking down at me both literally and metaphorically, and say those words. Finally, though, I spit them out: "Terrell, may I please suck your beautiful cock?"

"I can see how much you want to, Vic, so ... yes, you can suck my cock. Do a good job."

"You heard him, Vic," chimed Phyllis. "Do a good job."

And so I began. My tormentors wanted this indignity to last for a while, for their pleasure. I was determined to bring it to an end as quickly as they would let me. So, I began sucking Terrell's "beautiful cock" hard and fast.

From his moans and thrusts, it was obvious that he was enjoying it. But he was in no hurry to cum in my mouth. He would slow things down as he felt an orgasm coming on. He was using me to edge himself to a more intense orgasm.

Then I felt it. I felt an awful feeling. It wasn't Terrell cumming in my mouth. It was worse, if you can imagine that. What I felt was the sharp pain of the barbs in my chastity device poking into my cock. Damn it! I was getting a hardon from sucking Terrell's cock.

I tried to hide this from Terrell and my remote viewers but the pain grew intense and moaned loudly.

"Oh, wonderful!" I heard Lori say. "Vic is really loving it." I don't know whether she mistook my moan for one of pleasure or was just teasing me.

But when the pain got too intense, I had to fidget in a way that gave me away.

"You're right that he's loving it, Lori," Phyllis said. "He's loving it so much that he's getting hard!"

So now, Terrell, Lori, Phyllis, and whoever else was watching with the women knew that I'd gotten hard from sucking Terrell's cock.

"In the future," Phyllis said not to me, "we'll need to correct for that. We're not trying to condition Vic against this!"

"In the future"! What the fuck?

"For now, Vic," Phyllis said to me, "just do the best you can despite the pain. Focus on the pleasure you're getting, not to mention the pleasure you're giving Terrell."

I had no intention of focusing on Terrell's pleasure and I wasn't feeling pleasure. I consoled myself that there was nothing gay about my reaction. It was a sexually charged scene and it was natural, even for a straight guy, to react as I did. But the pain did make me focus on finishing Terrell as quickly as possible.

So I went at my task with intensity, if not enthusiasm. I began pumping his shaft with one hand and fondling his balls with the other as I moved my lips quickly over his rod, sucking hard all the time.

I tried to put the pain I felt in my own cock out of my mind as much as possible as I worked to end my torment.

Fortunately, Terrell wasn't interested in prolonging this any longer either. I guess he felt that he'd edged long enough. I felt his hands firmly on the back of my head, not really forcing me but trying to set a rhythm that worked for him.

And work it did! I felt his orgasm coming. His thighs clenched; his breathing became ragged; he began moaning loudly.

I felt the first gush of cum shoot down his urethra, first past my hand, then past my lips, and finally shooting deeply into my mouth. That gush was followed by six or seven more hard pulses, filling—no, overfilling—my mouth.

I tried hard to swallow as Terrell pumped his load in my mouth. But it was hard to keep up. When he'd finished, some of his cum was dribbling down my chin.

When Terrell pulled his softening cock from my lips, I started to wipe away the cum on my chin.

"No, no," Phyllis said. "Don't waste it. Push it in your mouth and savour it. Then swallow it.'

I did that, except for the savoring part.

"Now, lick Terrell's cock to make sure you've gotten all of his sweet cum."

Check.

"And kiss his cock and balls gently, then look up at him and thank him for letting you suck him off and for giving you his sweet load."

Again, this might sound strange but the kissing of his cock and balls wasn't as humiliating as looking him in the eyes and thanking him. But I managed to do it in order to end this horror.

"You can get up, Vic. But, before you put your clothes on, there's one more thing you need to do."

What the hell could that possibly be? I wondered, but not for long.

"You need to tell Terrell that he performed so well that you're putting him in for an off-cycle raise. Tell him that you'll write a strong letter to Mr. Simmons saying that Terrell's performance has been extraordinary and that he's risen to every challenge presented."

So Terrell was going to get his raise after all. Standing naked in front of the man I'd just been forced to suck off, I repeated the words. The only good thing about the situation at that point was that my erection was flagging and the pain from my cock cage was receding. The horrible thing was that even after drinking a glass of water, I could still taste Terrell's cum in my mouth.

It was just 3:30 at that point, though I felt as if I'd been tortured for much longer. I also felt that I should be let out of the 4:00 training, given what I'd just been through. But Lori and Phyllis thought otherwise. So, after a brief reprieve, I was again subjected to porn and the pain of the cock cage. Now, though, unlike the session with Terrell, that pain was part of the plan.