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Chapter 27
by
caitlynmasked
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Interlude One
Getting closer to Memorial Day means the temps are changing from ‘nice’ to ‘warm’ and occasionally, like today, ‘hot’. It’s a wonder that I complained so much about the cold with these skirts’ way back when. Now, with his new rule about the stockings and no pantyhose, I get a constant breeze on my legs that makes the hot temperatures easier to deal with.
Of course, most of that coolness is ruined by the damned faja Columbiana. At least all the sweat I produce ends up under it and not soaking these thin dresses. As I get off the train and head toward the office I look up and see that the sky is clear with the sun already rising. Thank God for the sun rising so much earlier as some days it seemed like I didn’t get to see the it at all.
It might have taken me weeks, but I finally got used to getting here even earlier than before. This way I can avoid the rush of men getting to the office. Yeah, they still bother me, still tease and flirt with me, still find any excuse to touch me especially when I’m standing up and they can reach my ass, but at least I don’t have to walk by crowds of them if I get here this early.
Sitting down at my desk I fall into my… what is this now? my third standard routine?... I put my purse and phone into the bottom drawer and lock it. There’s no need to smooth out the skintight skirt I’m wearing as I sit in my chair and wiggle into place. I boot the computer and run through my email. I’ve gotten so fast at this in just the few months that my bright pink nails fly over the keys almost nonstop as I re-distribute the company email regarding parking, respond to Jennifer’s request to help out at the Zeller retirement party, and send a smiley face response to the new baby photos circulating the secretarial pool.
Fuck. He’s even got ME thinking of it as the secretarial pool. No wonder they shun me whenever they can.
After my email is done I dig into Mal’s pile. As he continues to focus more and more on the McGregor acquisition, it’s become easier and easier to organize his voice mails and emails. Basically, it’s either Very Important and needs attention right away, is related to the acquisition and can be read soon or is not important and can be read once the acquisition is done. Most of it goes into that third pile and that’s what I’ll be working on this afternoon. I think Mal did that on purpose because so far as I’ve been able to tell, none of his previous secretaries delt with corporate issues like he has me do. He KNOWS I’m smart enough to do this, but he still has me acting like the stupid bimbo slut to all of his staff and anybody else I deal with. It’s beyond humiliating and is bordering on degrading. As word gets around, more of the guys are copying Frank and Thomas, making me sit in their laps as I give them reports or update them on the progress of the acquisition.
A quick glance at the clock tells me that I need to get Mal’s cuppa ready. Even though no one is around, pure muscle memory and habit make me pull out my compact and check my makeup before I leave my desk. He fucking insists on it. If I sit down for even two minutes, I have to check my makeup and pop my lipstick before I can stand up again. Bastard.
In the break room I breathe a sigh of relief as it’s empty. None of the girls staring daggers at my back, none of the guys rushing to stand next to me, finding a reason to slap my ass. But just as I’m finishing up with Mal’s cuppa, Darnell walks in. I give myself a single moment to let out the smallest of whimpers in frustration. It’s all I can afford before I have to turn on the shine. To turn Paris up all the way to 11.
It only took one time to make me realize he was serious. That we were in a new game and that he meant business. When I was having a bad day and just didn’t smile and flirt and giggle like a fucking idiot around everyone, word got back to Mal. Did anybody care that I’d twisted my ankle and was in pain? Nope. All they saw was Paris with what they called resting bitch face and Mal got involved. When he said I’d be punished for not being his ‘perfect perky girl’ I honestly thought he meant he’d dock my pay. I sorely wish he’d dock my pay now.
Instead, I found out why Mal likes to punish his girls. I also found out that no one near Mal’s office was ever going to be my knight in shining armor because as he pulled me over his lap, pulled my skirt up, yanked my thong up so that my was completely uncovered, and gave me five open handed spanks, I swear I screamed louder than I think I’ve ever been able to make noise. And what did he say once I got my tears under control and was allowed to stand up? He didn’t apologize, he didn’t give me any uplifting speech, he didn’t even tell me that this hurt him more than it hurt me. Nope, he simply said in his calm terrible voice, “Next time you aren’t perky, it’ll be ten.”
With that lesson still festering away I put on my big girl smile and turn to the tall dark and handsome marketing manager, “Hiya Darnell! It’s, like, great seeing you in this early. Can I make you a cup of coffee?” I feel my blush rise as I remember his growling words of ‘lay it on thick, flirt like you have never flirted before’ “I can make you a cup just like I like my men. Tall, dark, strong, and a taste that lasts in your mouth!”
Even though it’s been perky Paris for weeks, I can see that Darnell still doesn’t fully buy it. But at least he doesn’t try to corner me anymore and just accepts me being this way. I get a nice shoulder rub while he stands behind me, too close to be comfortable of course, while I pour him a cup of black coffee. Turning around I hold it up to Darnell, making sure his view will be right down at my proud chest, “Now if you’ll, like, excuse me Darnell, I need to get my man his drink. I’m sure I’ll see you later and we can pick up the twenty questions game again! Ta ta!”
Fucking ta ta.
I mince my way back to my desk, exaggerating my hips as I walk. Even with as nice as Darnell is, as gentlemanly and polite as he is, I know damned well that he’s watching my ass wiggle and jiggle as I walk away. He probably wouldn’t report me if I didn’t make it overtly sexy, but I don’t want to find out for sure. Five was enough.
When I get to the office, I feel my heart sink into my stomach as I see Mal’s office door open. He’s already here! Shit shit shit! I speed up my mincing steps and head right in seeing that he just got in and is setting his brief case down and taking his jacket off. As I set the coffee down on his desk, standing too far away of course making me bend forward to let my breasts hang down appreciably, I try not to tremble as I feel Mal’s hand trace its way down from my shoulders to the small of my back, up the curve of my ass, and down to my thighs.
Knowing better than to move, I wait in this position that presents my ass as if begging to get spanked. As expected, after a moment’s thought, Mal provides the spank hard enough that I let out a little yelp even though I knew it was coming. He loves that.
Standing up and turning my smile all the way up, I ask in my bubble gum voice, “Is there anything else I can get you Mal?”
Mal walks casually to the door and closes it. As he pulls the blinds, blocking off his office from the view of the entire floor, I try my best not to tear up. He hates it when I cry but it doesn’t stop him. It just takes longer which makes the whole process worse. His voice is that same quiet grating commanding voice as it always is. To anybody that doesn’t pay close attention, it probably sounds like his normal voice. But I can hear the strain under it. He’s mad. Or at the very least he’s frustrated. “Nika is being a bitch again. She hates her Range Rover. We sat down with that dealer for four hours and he went over every single option. She insisted she didn’t need the SV, just the standard Range Rover. And when we get it, customized in every way she wants, does she say thank you? Nope. She bitches because it’s not custom enough. Because she saw one that was the same exterior color and a different one that had the same interior color. So now I have to find some schmuck to buy that two-hundred-thousand-dollar tan monstrosity so that I can buy her a three-hundred-and-fifty-thousand-dollar champagne monstrosity.”
I can already see where this is going and it is NOT how I wanted to start the day, but I can’t show the initiative and just get to it. Nope. I have to let him lead me there like a deer to a trap, “Oh, that’s icky Mal. I’m sorry you, like, have to deal with that. Would you like a back rub? I’m sure that would make it better. Or, like, maybe a foot massage? Theres time before your first appointment.”
I keep that same eager to please look on my face even if it doesn’t intrude upon my eyes. My arms are stiff and straight with my hands clasped together in front of me while I bounce up and down just enough to ensure I’m wiggling and jiggling in all the right places. Just like he likes. When he looks up at me, I swear it’s almost like he’s considering it. Like a back or foot massage is what he’s after. Instead though, he walks over to the couch and pats the seat next to him, “Nah, I think I need to get rid of a little more stress than that. You treat me so good Paris!”
Taking the tiny steps he likes to see, I make my way to my boss’ side and sit down in an exaggerated manner that stretches my already tight skirt, showing off my big fake ass. In one fluid motion I cross my legs at the knee, lean forward, and start undoing his belt. When his pants are open, I slip his cock out with hated practiced ease. After a few dry squeezes and a few quiet ohs and ahs, I use the always within reach bottle of lotion and lube up my hand before gripping his girth and starting the slow process of giving my boss a hand job.
I honestly believe at this point that God is cruel. As I lean my face against his shoulder and make the cooing humming noises he likes to hear from me, I wonder how he won the lottery on all fronts. Even I, a straight guy that just so happens to be stuck playing the role of a slutty bimbo secretary, can acknowledge that Malachi Orpheus is an attractive man. He doesn’t have to work hard to keep his body in shape and at six foot two and just under two hundred pounds, he’s in very good shape. While a good portion of his hair is greying, it’s coming in that salt and pepper that adds intrigue and mystery and gravatas to him. It makes him look better, not old. He has some crow’s feet around his eyes and laugh lines around his mouth but otherwise no wrinkles. And his hair isn’t even thinning. He has more money than most people could spend in a lifetime and is on the verge of making more than enough that his own children couldn’t spend it all in THEIR lifetime. While his wife is a bitch, Veronica is beautiful beyond compare. Most of her is natural but the little cosmetic touchups she’s had ensures that she still looks young. I heard one of the valets actually mistake her for Mal’s daughter once. God, the way he puffed up then. He has a lavish home in the burbs, an apartment here downtown, and at least one vacation home that I know of.
And as if that perfect life wasn’t enough, the deal he made with the devil also gifted him the cock of an Olympic God. He certainly doesn’t need any little blue helpers to get to its full eight and a half inch hardness. And I mean true hardness. I bed he could hammer a nail into hardwood with this thing when he’s really turned on. In addition to a good length, he’s so fucking thick that my dainty hand can barely reach around it. I could put both my hands on his cock, one at the base and one near the head, and still have room to jack him up and down.
Sitting here with a curvy ass, big tits, wearing a tight skirt and blouse that shows off that ass and tits, smooth legs, long overly styled red hair with highlights, lowlights, and just the right amount of shine, and of course cosmetics applied like a movie star, I naturally feel like a woman next to him. But if I were me, the real male me, Jamie me, with my body hair, five o’clock shadow, normal voice, and everything and was still sitting next to him? Yeah, I’d still be inferior. His cock is that impressive, and now it’s my fucking responsibility to take care of when he’s in the mood. It’d be bad enough, humiliating enough to have to do this once, but with his bitchy wife and the fact that he can’t roam around for other women, it means that I find my hands wrapped around his cock at least a couple times a week.
And I’m getting really good at giving him hand jobs.
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You're Not The Boss Of Me
Going undercover as a secretary backfires for poor Paris
Paris agrees to help his apartment mate Grace help
Updated on May 10, 2026
by caitlynmasked
Created on Aug 26, 2025
by caitlynmasked
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