Bad Boss Pt. 08

Part VIII: The Ghosts of Transgressions Past: Intersectional Discrimination

Friday morning Lori told me that I would be relieved from my third training session of the day--the one in the late afternoon. Sounded good until she explained the reason. She and Phyllis had an evening event planned for me. They wanted me to be prepared for it. So I was to go home early, shower, and put on comfortable clothes. Then I was to meet them at the same location I'd first been humiliated in--where I'd been drugged and hypnotized into thinking I was a beautiful young woman and, under that misimpression, I'd sucked off every one of my male employees.

"What are you planning to do to me?" I asked, as if I could somehow veto plans I didn't like, or at least that it would somehow be made better by my knowing in advance the fate that was to befall me.

"Oh, don't worry. It's nothing like last time. Nothing at all." For some reason, I wasn't reassured.

The morning and midday sessions were pretty much routine, which means awful but not really anything special. After the midday one, I went home, showered, and, because I was free of my chastity device, whacked off. I was hoping not to repeat what happened last night when I jacked off. It was awful! I was jacking to an interracial video and, just as I was nearing my climax, the woman who was sucking a huge black cock for the money shot turned the cock toward the camera and said, "I'll bet you want this, don't you?" And then the impossibly large cock shot an enormous load of cum right on the camera. All the while it was spewing its load, the woman was cooing to the imagined audience about how they loved to suck cock and how much the loved cum.

I was so near my orgasm that I didn't stop. But my pleasure was tainted because all I could think about as I was cumming and watching the cum coat the camera lens was me sucking cocks and taking loads in my mouth and on my face. I tried to put it out of my mind and just experience the pleasure of my orgasm.

It turns out that trying not to think about something when you're jacking off is about as successful as trying not to think about something any other time. Try as I might, the images in my mind as I worked toward an orgasm were those of being on my knees, naked, sucking a cock--Terrell's, which matched the color of the one on the video, Jerry's, which matched the size, or Pete's, which matched the load delivered.

And it wasn't just visual images. As I neared my climax, it was as if I could feel those cocks filling my mouth and taste the cum they deposited there. So, my jack off session was tainted. Still, I had an intense orgasm and shot a bigger load than I'd remembered shooting in a long time. I felt the temptation to wipe my cum up from my abdomen and taste it. But I resisted that temptation.

I hoped that, having drained my balls in my Friday afternoon whack off session, I might avoid some of the torture my tormentors had in mind for me tonight. Whatever they planned, maybe my body wouldn't respond in ways that humiliated me. I was wrong.

I showed up at the time and place Lori and Phyllis had specified. They were already there, sitting at a table with one empty chair. They motioned me to sit down. They opened a bottle of wine and poured three glasses, putting one in front of me. I figured it was safe enough to drink this. I didn't trust them at all. They'd drugged me before. But I'd watched them open the bottle and pour the wine for all three glasses. So, I took a big swig from my glass of wine.

"So, we're here to discuss some of the horrible acts you committed that brought us to this point," Lori led. "This evening, we want to talk with you about Mabel Wilson. Do you remember her?"

I nodded. Of course I remembered her. I'd let her go after just nine months with the company. She was a fat black woman who really didn't fit in the McNeeley Company.

"You fired her, right?" I nodded again.

"And why did you do that?"

I wasn 't going to say the real reason. So, I just said I didn't think she fit well with the team.

"Oh, was that the reason? And why did you think she didn't fit well?"

I shrugged, "She just didn't."

"Well, maybe this will refresh your memory." Lori pulled out a voice recorder and pressed the play button.

What the hell?! This was a recording of a private conversation that took place in my office. I was feeling victimized by her violation of my privacy. But, more than that, I was feeling very uneasy because I knew what was on the recording.

I'd been talking on the phone with a friend who worked in another company. Somehow the conversation turned to the unpleasantness of firing people. And I complained that I was going to fire one of my employees the next day. He asked why the guy was being fired. That's when the relevant portion of the recording began.

"It's not a guy. It's a woman--a fat black woman. I can't stand looking at her. She must weigh 250 pounds and she's not more than 5'3". I mean, talk about disgusting!"

"Did she fuck up?" my friend asked.

"Naw, her work is fine. I just can't stand looking at her. And I can get someone else to do the work, someone who's friendlier to the eyes."

As I listened to the recording, I could tell that my friend's tone was disapproving, though I hadn't realized that at the time. But that was water under the bridge. The other thing I realized was that Lori and Phyllis had all the ammunition they needed for their holy quest against me.

About that time, just as I'd drained my wine glass, things started to get fuzzy.

"God damn you! You drugged me again."

"Yeah, we did," Phyllis said smugly. "We drank the same wine but your glass had a little pretreatment. This is going to be fun."

I was conscious but I didn't feel in control of my body. Phyllis began talking to me in exaggeratedly soothing tones. I tried to resist her control, but resistance was futile.

Within a few minutes, I was completely under Phyllis's control.

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"Strip!" she commands. When I'm completely naked, she goes on. "Now, Vicki, you're a very beautiful, sexy woman, with a slender body and beautiful breasts." She pauses. "Look at yourself."

I look down on my body. I'm gorgeous! The kind of woman any man would love to fuck.

"Go over to the table in the corner and get yourself dressed. You have a date and I know you're going to love it."

The clothes on the table are extremely sexy: black lace bra and panties, fishnet stockings and a black garter belt, high heels, and a sheer purple nightie. These obviously aren't for going out. My date is going to happen right here.

I love getting dressed in these and I admire my reflection in a mirror that's standing near the table. Wow, I think, I'm a sexy bitch!

Phyllis interrupts my vanity session. "Hey, Vicki... your date is here." I turn and see a large, Black man entering the room.

"Vicki, this is Marcus; Marcus, Vicki is really excited to meet you and looking forward to a stimulating evening."

"Why don't you get on your knees, Vicki, and get familiar with Marcus's cock?" It's clear that there's to be no small talk. The idea of servicing a complete stranger is strangely appealing to me. I seem to recall something Phyllis or Lori had said about how much I'd like the idea, but that memory is hazy. In any case, I'm definitely up for it--or, I guess it's more accurate to say,down with it.

It's hard to wrestle Marcus's cock out of his pants because, well, it's hard! Marcus's cock is the largest I've ever seen, maybe including those seemingly impossible cocks in porn films. I don't know what all I'm going to be able to do with it, but it's going to be fun to explore the possibilities.

I put both my hands around the shaft and marvel at the weight and mass of his cock. I hear Phyllis urging me to take the head of Marcus's cock in my mouth but it's an unnecessary prompt. There is no way that I'm going to miss out on feeling this enormous shaft fill my mouth.

And fill my mouth it does. Try as I might, I can't get more than the head in my mouth. But I love the feeling of it. I love how the helmet feels when it passes my lips. I love the way it stretches my jaw, forcing me to submit to the raw power it has over me.

I run my lips up and down the length of the shaft, making it glisten with my saliva. That allows my hands to slide smoothly over the length of the shaft as I stroke it adoringly.

Suddenly, I feel Marcus pull my head away from his cock. I'm disappointed. I could have sucked the head of his shaft for a long time and the thought of it spewing its load all over my face and down my throat was exciting to me.

But Marcus has other ideas. He spins me around and onto all fours. He tosses the bottom of my nightie up over my hips. I feel his hands pulling my panties down.

Now it's not disappointment that fills my mind; it's a mixture of desire and dread at the thought of Marcus shoving his huge cock into my tight pussy. I'm terrified at the prospect but, at the same time, incredibly excited. My thoughts about it, though,are clearly irrelevant to what is going to happen. Marcus is getting my panties completely off. And I know what's coming next.

Thank God, I think as I see Marcus smearing lube over the entire length of his shaft. I still don't see how my cunt will accommodate its girth, but better lubed than not.

I feel the tip of Marcus's cock pressing against my cunt lips. His hands are grasping my hips firmly, holding his target still as he takes aim and prepares to impale me.

Fortunately, Marcus takes it slowly, allowing me to open to him gradually. Still, it doesn't go easily. My cunt has never been stretched like this and it doesn't open this wide willingly. But Marcus is insistent and finally I feel him enter me. The pain is intense and it doesn't recede quickly. But, after a few minutes of slow, even gentle, sliding in and out, I do feel the pain ebbing.

When I can finally put the pain aside, I focus on the other sensations that are flooding my consciousness. There is a spot that Marcus's cock hits on his forward stroke... I guess it's my G-spot. I've never felt this sensation before. It's intense and intensely pleasurable. I find myself moaning with pleasure and moving my hips to increase the pressure of his cock on that spot.

Suddenly, without warning, I'm orgasming--intensely and continuously. And, for the first time in my life, I'm squirting vaginal fluid. I've seen that in porn films, of course, but never experienced it before. My juices flood the floor below me.

Marcus stops and slowly pulls out of me. I feel empty but more sexually sated than I've ever felt before. My heart is still pounding and I'm still gasping for breath. For a moment, I'm thinking about nothing--just floating in my post-orgasmic nirvana.

"Oh, Vicki," Phyllis interrupts, "you'd better recover quickly. You have another visitor."

Sheeze! I'm exhausted. But I manage to turn around to look at the rest of the room. I don't see Marcus anywhere. Where did he go? Why did he go? I don't have time to think about it. What I do see is a very large Black woman, sitting in a chair.

I'm confused but Phyllis pipes up before I have time to try to figure things out.

"Vicki, I know you've never been with a woman before, but you've always wondered what it would be like. You've always had a fascination with women, especially with big, beautiful, Black women."

As she speaks, I realize that she is right. I'd never thought about it but now the idea of having sex with a big, beautiful, Black woman is enticing, irresistable. I feel my energy returning.

"Why don't you crawl over and initiate things? I'm betting she'll let you run your hands up the insides of her thighs and caress her."

I do exactly as Phyllis suggests. Putting my hands under the woman's dress and gently pressing her thighs apart to run my hands up them, near her crotch. Her thighs are thick and hot and moist and the feel of them excites me.

"I know you want to see her beautiful body, Vicki. Why don't you ask her to take her clothes off?"

I do and the woman stands up and begins undressing. Her body isn't at all what conventional standards of beauty prize. She's very heavy and her breasts are large and sagging. But her dark, glistening skin looks beautiful to me. The rolls of fat are not disgusting but exciting. The folds of flesh look inviting and the thought of nestling in them appeals to me..

The woman stands next to me and I can't resist reaching up to put my hands on her full heavy breasts. She's short enough and her breasts hang low enough that I'm just able to get my mouth over them, one at a time. I enjoy suckling on them while massaging them with my hands. I've never imagined that I would actually touch and suck on breasts so large and full.

The woman steps back slightly and then lies down on the blanket that is on the floor. She spreads her legs ever so slightly but enough that I take it as an invitation. I crawl between her legs, pressing them apart. I gently run my hands up the inside of her now bare thighs, The woman twitches with pleasure as my hands near her crotch but I think that, if anything, my excitement is greater than hers.

Now lying down between her massive thighs, I begin moving toward her crotch. My nostrils fill with the scent of her moist mound and I find myself growing more and more excited as I near my goal. My heart is pounding in anticipation.

I gently pull apart her outer lips and bring my tongue to her clitoris. I've never done this before but I know what feels good and I'm high on the eroticism of the moment. I flick my tongue quickly against her quivering clit and revel in the shiver of pleasure it obviously sends through her body. I lick her clitoris again and then suck it between my lips relishing the taste and feel of it in my mouth.

The woman is moaning and writhing with pleasure and that just excites me more. The idea that I am causing such pleasure in this beautiful creature makes me feel powerful and impells me to be even more vigorous in my efforts.

Soon she is convulsing in pleasure, screaming out as her orgasm overwhelms her. I still want to lick her clitoris but I can tell that it is too sensitive now and, so, I resist the urge.

I crawl up next to her and rest my head on her huge breast, feeling completely satisfied myself. The sound of her heart beating, and slowly returning to a normal pace, is soothing to me. But my tranquil state soon ends.

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"That was really nice, Vic."

The word 'Vic' shattered my reverie--my whole world, really. Vic! I was suddenly disabused of the illusion that had been my world for the evening. I sat up and looked at myself. I wasn't a beautiful woman. I was an overweight, middle-aged man who was ridiculously dressed in a bra, stockings, and a nightie.

It took a minute for things to gel in my mind. Again, Phyllis and Lori had drugged and hypnotized me. Again, they'd humiliated me and made me do disgusting things that they had no doubt recorded on their phones. Would this cruel torment ever end? I wondered.

Lori drew my attention to where they were sitting and said, "That was really nice, Vic. It doesn't make up for the way you treated Mabel when she worked for you, but I'm glad you tried to make amends."

It was only then that I looked at the woman I'd been pleasuring and was able to see who it was. I hadn't recognized Mabel when I was under the evil spell that Phyllis and Lori had imposed on me. But now, of course, I saw that it was her.

Mabel was smiling at me as she got up and began putting her clothes on. "You did a good job, Mr. Simmons. You might think about moonlighting as a cunt licker. I'm sure some women would pay you for your services."

I didn't reply. What was there to say? I could still taste Mabel's juices in my mouth. I wasn't feeling very powerful at the moment.

"You know, Mr. Simmons--or should I call you 'Vicki'?--you know, Lori said she could get me my old job back at McNeeley Consulting, with a raise, no less. I guess they've sort of got you over a barrel, don't they?" Mabel didn't wait for an answer.

"And it's an attractive offer because, as I hear it, there's a great employees' benefits program that you're providing. And, after tonight, that's especially attractive." The prospect of having to spread Mabel's fat thighs and lick her stinky cunt whenever she wanted me to was revolting.

"But, you know what? I've got a good job now, much better than my job at McNeeley Consulting. And I don't have to work for an asshole like you!"

Mabel had had her say and,with that, she sat down and shut up, satisfied with the humiliation she'd dumped on me. But Lori and Phyllis weren't done with me yet.

"You're wondering what happened to Marcus, aren't you, Vic?"

I nodded. Their question had brought me back to the mystery I'd been unable to resolve before they got me servicing Mabel.

"Well, Phyllis might have manipulated your perception of reality a bit more than you realize. Marcus was Mabel, you just saw her as a man."

"No way!" I shook my head. "No way. Marcus... " I stopped. I was about to say, Marcus had a huge cock and he fucked me with it. But the words wouldn't come.

"What, Vic? Marcus had a huge cock and he fucked you with it? Is that what you were going to say?" How the hell did she know exactly what I was going to say?

"Here, I'll show you Marcus's huge cock." And Lori walked over to the chair beside where Mabel was sitting and picked up a huge, but otherwise hyper realistic black strapon dildo. "Here's Marcus's huge cock that you loved sucking and getting fucked by so much." She laughed.

"You really loved getting fucked, didn't you?" Lori said. "You loved it so much you shot your load without your little pecker even being touched. I guess "Marcus" gave you a pretty good prostate massage."

Phyllis chimed in, "I didn't know if that would happen. I'd planted the suggestion, but I didn't know if it would work. You did great, though, Vic--or Vicki--you spewed your load right on cue."

So, that's what the squirting had been about. Shit! No doubt Lori and Phyllis had video evidence of my having a prostate orgasm from being fucked. I guess given the way I was dressed, it's fair to call it a 'sissygasm'. More leverage for them, as if they needed it.

"You'll be happy to know, Vic," Lori said, "that the revenge is over. I think we've done all we can do to educate you and try to make you a more decent human being.

God! A huge cloud lifted. "You mean, it's really over. Things can go back to normal."

"Well," Lori said, "they can never go back to the way they were before. I hope you learned your lessons well enough to understand that."

Like a chastened schoolboy, I blurted out, "Yes. Of course. I've learned my lesson" The prospect of my torment ending was like a ray of sunshine at the end of a turbulent storm. And, I'd have said anything to hasten the end of this torture they'd been inflicting on me.

The ray of sunshine dimmed a bit when Lori went on. "Of course, the employee benefits program will continue. It's good for morale and the guys have gotten used to it. It would be terrible to end that program."

It's a sign of how far down I'd sunk that even this seemed a relief. I mean, sure, I'd be sucking off several of my employees whenever they wanted a blowjob or just wanted to humiliate me. But it was the end of the chastity devices and the end of the drugging and hypnosis. At this point, that felt like a win.

Mabel chimed up then. "Well, I don't want my old job back. I'd never work for a shit like Vic again. But, if the employee benefits program is still in place, maybe from time to time, it could be extended to ex-employees."