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Secretary’s Day — a short story (MF, humil)

a short story by Dylan Cross

Good morning, Miss Wendy.

“Good… good morning Sir.”

How was your evening?

“F-fine Sir.”

Was it? Or are you just saying that to be polite, Wendy? You know how I feel about dishonesty.

“Yes Sir.”

What do I always tell you about lying to me?

“That you’ll, um, wash my mouth out…”

With soap?

“No…. With… with… cock…”

…After doing what with it? Don’t be shy, Miss Wendy.

“After, well, um, after f-fucking my other… my other two holes with it…”

Good girl. Now, tell me about your evening.

“Sir, two of… two of the loan sharks came to my… to my apartment…”

Oh, how terrible, miss. They didn’t hurt you, did they?

“Not… not exactly Sir…”

Well, what did they do?

“They… got rough with me Sir…”

And what did they do?

“S-something called a… a DP. Both of them… shared me Sir.”

Aw, Miss Wendy. There’s no need to be ashamed. What did they say to you?

“T-that if they… if they had to… um… c-come back… they’d take… they’d take me… you know, into the kitchen… and the… the stove would be used… oh my god I’M SORRY SIR….”

Wendy. You don’t need to apologize for crying. To tell you the truth, it actually gets me somewhat aroused. Here, take a tissue.

“Th-thank you Sir.”

Why are they bothering you again? Didn’t they get their payment?

“No Sir. They said you… you haven’t paid them this week.”

That’s strange. They know that you and I made an arrangement, don’t they, Wendy?

Speak up, Wendy. I can’t understand sobs.

“Y-yes Sir.”

And what was our arrangement?

“You said you would make… make the p-payments for me.”

And what was your end of the bargain?

“Being… being your little personal… you know, your personal… um, whore.”

And have you fulfilled your end of the agreement?

Wendy. You will answer me when I ask a question. Or would you prefer to seek employment elsewhere?

“N-no Sir.”

Very well. Have you upheld your end of our little agreement?

“I… I think I… yes Sir.”

Miss Wendy. I seem to remember you on my desk, last week, and a certain ungrateful little secretary of mine, struggling with me and covering herself with her hands…

“Sir! I… I try… but… but… Sir the clamps hurt so much! And the… um… when you… you know… when you p-put it… um… back there…”

Back where, Wendy?

“In my… my rear…”

Wendy. We’ve talked about your vocabulary. Try it again. Now, tell me what you were trying to say… but use language befitting a whore like you.

“Sir I… I just don’t like it when you… you p-put your, um… your cock in my ass…”

Much, much better, Miss Wendy. I know you don’t enjoy that very much. But *I* do enjoy it. Very, very much. And isn’t that what a whore does? Makes sure her partner is completely satisfied?

“Yes Sir…”

And you DO still want to be my little whore, don’t you?

“Y-yes Sir.”

Then say it.

“S-sir, I… I’m your… your little wh-whore.”

Here, take some more tissues, dear. Go ahead and hold onto the box.

“Th-thank you Sir.”

So, let’s recap. You, Miss Wendy, borrowed far too much money from the wrong people. For jewelry, cars, tattoos, and your overall lavish lifestyle.

“Yes, Sir.”

Look at me when I talk.

“Yes, Sir. I’m sorry, Sir.”

Because you think you are entitled to everything.

“Yes, Sir.”

Because you are a spoiled little bitch.

“Y-yes Sir.”

Say it.

“I… I’m a spoiled little… little bitch.”

LOOK AT ME and say it.

“I’m… a spoiled… little bitch.”

No. Don’t look away, LOOK at me when you say ‘bitch’. Again. Tell me.

“I’m… I’m a s-spoiled… bitch.”

Yes. And you found out the world does not owe you anything.

“Yes Sir…”

In fact, you found out that the world is a cruel place. Especially when you don’t pay your debts.

“Yes Sir.”

And you came to me for help.

“Yes, Sir, but…”

And I agreed to help you.

“Yes Sir… but…”

And you and I came to an agreement to help each other out. Yes?

“Yes Sir! But… Sir, how much more money do we… uh… do I owe them…”


“Yes Sir…”


“Sorry Sir I’m t-t-trying…”

You came to me for help. I told you I WOULD GET YOUR DEBT PAID OFF FOR YOU. And now you are QUESTIONING MY COMPETENCY.

“N-no Sir! I just… well, Sir… you… you made me s-sign over all my, um, paychecks to you… I just thought… I w-was just wondering if… well, it’s been, six months, and, well, um, Mr. Scoleri’s bill should have been paid off by now…”


“Sir? No, I—”

Get out of my office. You are fired.

“Sir, no, please! I—“

You may deal with Mr. Scoleri and his, um, employees without further interference from me. In fact, I’m going to stop payment on the last check I gave them for you.


Leave now, or I will phone security right before I call Mr. Scoleri.


Do you mean that?


No more questioning what I do with your paychecks?

“No Sir… I… your whore… isn’t responsible enough to handle money…”

Don’t worry, Miss Wendy. I still give you an “allowance” out of that money, don’t I.

“Yes Sir… and your whore is grateful…”

And where will you spend your “allowance”?

“P-probably at Victoria’s Secret, Sir. So I can dress like a… like a trashy slut for you…”


“I AM a trashy slut for you Sir…”

Yes, you are. In fact, I’m going to “up” your “allowance.”

“Thank you Sir… but… won’t that make it… um… take longer to pay back…”

Are you questioning me again, Miss.

“No… no Sir! Th-thank you Sir, your whore is grateful for more spending money…”

What do you think you should spend it on?


What are some of the things I’ve mentioned, wanting to get for you? I think you have PLENTY of slutwear from Victoria’s Secret, don’t you?

“Yes Sir.”

So what do you think you should buy for yourself? Maybe, from the bondage webstore I showed you?

“Sir, I…”

Tell me. And you had better come up with creative ideas.

“Um… r-rope…”

Ah, yes. We can never have too much of that.

“Hand… handcuffs. Sir. For when I… struggle.”

Yes. Very good! What else.

“A… um… a… plug.”

What was that? Speak up, Miss Wendy.

“A plug.”

What sort of plug?

“For my rear…. Uh… I mean… for my… to put in my ass Sir.”

Excellent. And, we’ll probably have just a little money left. I wonder what else we can order?


“S-some…. Some clamps…?”

Very good, Miss Wendy. I trust you’ll get this all done when I give you your allowance?

“Y-yes Sir.”

Very well. Do you have your itinerary ready for the day?

“Yes Sir…”

Go on.

“At…um, 8:30 Sir, I will give you your morning blowjob. I will have five minutes to, um, finish… or…”

Ah yes, thank you for reminding me. I was late for my meeting on Friday because you didn’t make me cum quickly enough. But we dealt with that accordingly, didn’t we?

“Yes, Sir.”

I trust the soreness in your nipples has gone away by now?

“Mostly, Sir. Yes, Sir.”

I really AM sorry that I got carried away. The teeth marks WERE rather brutal.

“I deser— the whore deserved it, Sir.”

And what are you going to do to ensure that you do a better job this time?

“I’m… I’m going to… do it better…”

How? Remember that I am detail oriented, Wendy. Elaborate.

“I’ll try… try to, uh, you know… take you deeper…”


“I WILL take you deeper in my mouth Sir.”

Good. What else?

“I… Sir, with your permission, maybe I can… um… put my hand down there, like… you know, under my skirt… and, um… touch myself… make myself moan while I… suck you…”

Miss Wendy!


That is BRILLIANT! I absolutely LOVE when you take this sort of initiative. Of course you have permission to rub and finger your dripping cunt while I fuck your throat.

“Thank… thank you Sir.”

In fact, I am so proud of you, that I am going to help you out with that five minute time limit. You can come over here… come around the desk, Miss Wendy, take my cock out… that’s it. Now you may stroke it while we cover the rest of your itinerary. Giving you a “head start,” so to speak, on making me cum.

“Sir… after your, um, blowjob, you have—”

Miss Wendy.

“Yes… yes Sir…”

Do remember your manners.

“Sir? My…”

Feel free to thank me for allowing you to make your job easier.

“Oh. Yes Sir. Thank you, Sir. For… for letting me stroke you…”

Much better. Ah… you have talented hands, Miss Wendy. Do go on.

“After… after you, you know…”

Cum all over you?

“Yes Sir. Um. After you do that… I will… bring you coffee, and… um… flirt with everyone in the cafeteria…”

Very nice. I’m sorry, I think you missed something, Miss Wendy….


When you are through sucking my cock, where exactly are you going to take my cum?

“Sir… um… last time you… did it, in my hair… which means… um… this time… on my… my face…”

Yes, that sounds about right. Keep stroking it, you little whore. Oooh. A little bit of friction. Drool all over it, Miss Wendy, lube it up. That’s it, get your blonde head down there. Give it a few licks too… mmmmm nice. Go on with your itinerary.

“Well, Sir, when you go to your meetings, I, you know, have that… appointment…”

Which appointment was that, Wendy? Forgive me, I have a lot on my plate. Refresh my memory….

“You… told me to… get a consult… for, um, for… enlargement…”

Ah, yes. Those 34Bs are quite a disappointment. It’s going to be nice to see you walking around the office with something more… appealing to look at.

“Sir, it’s just a consult though, it would be expensive, there’s no way I could afford…”

Don’t worry, I’ve already considered that, miss. Another loan from Mr. Scoleri should cover it…

“Mr. Scoleri! But, Sir, I can’t even pay back the money I already owe him!”

I’ve made arrangements with Mr. Scoleri. As luck would have it, he owns a, um, bar, called The Layover. It’s out near the airport. Perhaps you’re familiar with it?

“N-no Sir…”

Yes. Mr. Scoleri has agreed to allow you to come and work for him there.

“Doing… what, Sir…”

Earning money to pay back your debts.

“Yes Sir… but… but… how will I…”

Don’t be alarmed, Miss Wendy. It will be nothing which I haven’t had you doing around here.

“Y-yes Sir.”

So. These implants. How big were you thinking of going, Miss Wendy?

“Um… Sir, I, well… maybe a C…”

A “C”??? Goodness, Miss Wendy, that wouldn’t even be worth doing the procedure! I think you will need at least a double D!

“Sir… that’s… well, big… I’m a small girl…”

Yes. Which is why bigger is better. Men like me want to fuck a WOMAN, not a “small girl”. Which one do you want to be, Miss Wendy?


What was that, Wendy?

“A woman. But, Sir…”

Yes, Miss Wendy?

“I… well, Sir, I can be… you know, a woman, without the double D’s…”

You think so?

“Yes Sir! I can show you, please give me more time to show you…”

I think the double D’s would be very sexy. But I’m just one person with one opinion. Others might have differing ideas on what is beautiful, is that right?

“Yes Sir.”

Perhaps I shouldn’t be so impulsive, and so eager to “super size” you.

“No, Sir. Thank y—”

What time were you supposed to go to this appointment?

“Ten thirty Sir.”

Maybe we should rethink this.

“Yes Sir!”

I have a terrific idea, Miss Wendy! After you bring me my coffee, you’ll have an hour and a half till your appointment.


I want you to take a walk around the office. Find out what others think! Tell them you are considering the implants, and solicit their opinions.

“Sir, please, I can’t just…”

Talk to every one of your male and female co-workers. An impromptu survey. And you’ll take your clipboard along, and write down their responses!

“Oh Sir, please don’t make m—”

And, by all means, we should let them see what you are working with NOW. To that end… please remove your bra.


Here, I will help you. Let’s just… ok, now turn around, Miss Wendy, and… there. I’ll hold onto this so you don’t lose it. I see you wore your white blouse today. It’s practically see-thru.

“Yes Sir. Please, I’ll ask the doctor about… about the double Ds. You don’t have to—”

No, Miss Wendy. We should exercise diligence. Make sure we’re making the RIGHT decisions!

“Sir, Please. I was out of line, the bigger size is a good idea, I…”

I want your report to contain the names of everyone who participates in your little “survey.” Their responses… and, Miss Wendy, I want a check box next to each name.

“Check box… for…”

The box will be checked to indicate whether they actually felt you up. I want you to offer each of your “subjects” the opportunity to squeeze, fondle you.

“Sir! I can’t just…”

And at least 50 percent of those names had better be checked off.

“I… I don’t know if I…”

I think we’ve dealt with your morning schedule. What comes next?

“Please, Sir, I beg you, don’t make m—”

We’re finished discussing your morning schedule. Lunchtime, Miss Wendy. Don’t make me ask you again.

“Lunchtime… um… Sir, you and I are…. Are having lunch… I, uh, I booked the south conference room…”

Very good. And why did we want that room, Miss Wendy?

“B-because… the… the door l-locks… it’s, um, further away from the, um, other offices…”

Is that all?

“No Sir… it… the room is… the room is s-s-sound… soundproof…”

And why did we want that?

“You can… Sir, you… you can… uh… get rougher w-with me… hurt me… make me scream…”

Please don’t forget to bring the nipple clamps, Miss.

“Sir… please! I beg you, not those. Please Sir THEY HURT SO BAD! I’ll… I’ll do anything… Sir you can even, um, I’ll let you… fuck my tight secretary ass… willingly…”

You’ll “let” me?

“Yes Sir! Please, no clamps, I will be good, I will do EVERYTHING…”

Miss Wendy. If I want to fuck your ass, I will fuck your ass. Willingly, or otherwise. I don’t need you to “let” me.

“Yes, Sir. I didn’t mean—”

You have nothing to barter with. It already all belongs to me. But now that you have given me the idea… in ADDITION to the nipple clamps…

“Oh, no, oh Sir please NO…”

Bring the bottle of lube.

“Please, Sir…”

Or, I could go in dry. I don’t think you want that…

“N-no Sir…”

Good. So, we have lunchtime covered, yes? Or would you like to argue with me some more?

“No Sir… no… no arguing… but… I am just begging you not to use the clamps…”

Your afternoon itinerary, Miss.

“Sir… you… your prospective clients are coming in… they will be in, um, north conference room at 2 pm…”

And where will you be?

“Under the table Sir…”

And you know how important this meeting is?

“Yes Sir.”

How many are coming to the meeting?

“Th-three Sir.”

Sounds like an easy afternoon of work. For an easy secretary.

“Y-yes Sir…”

And after the meeting….

“At 4pm, your, um, afternoon blowjob Sir. And my performance review…”

Ah, yes. I’m going to have to make a tough decision, Miss Wendy. The Finance and HR department heads have been giving me a lot of grief about having kept you on the payroll. They are pressuring me to make cuts. I hope today you’ll show me why I should keep you on…

“I’ll t-try Sir…”

There, there, Miss Wendy. More tissues?

“Yes Sir… I’m… I’m sorry Sir…”

It’s no worry, Miss Wendy. But it’s 8:30 already. We have a busy day ahead… shall we get started?

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