Stuart's Secretary

Story Info
He hired a Master who made the young lawyer jump!
2.7k words
3.73
16.6k
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Stuart thought dreamily of his days at the firm in Chicago, and the two male Masters he'd lived with...

One of them deaf.

The rich 26 year old Stuart had loved and feared the two men.

Now he watched BDSM porn...

The way that model has his cock whipped reminds me...

Of the day Master Pietro caught me with the Frederick's of Hollywood catalogue that I'd stolen from the neighbor's porch...

And Master John had taken my penis out of my pants and slashed it again and again with an old vacuum cleaner cord as I'd screamed...

Oh, but my cock was twice as hard when it was over...the whipping my Masters had given me...

Stuart was almost possessed by the young man wielding the scourge...

His head was shaved, and he was a sort of golden color with prominent features...

Lebanese?

Suddenly there was a tap at his office door.

Stu looked up hurriedly, pushing the magazine that had been occupying his attention into the bottom drawer of his desk.

Stu's erection had been nearly tearing the crotch of the elegant Armani Pinstripe Lurex dress slacks he was wearing...

Thinking of the scourge lashing whitish bare buttocks...

Stu put the Kelham Plastics account file in front of him.

This, to hide the bulge in his pants and the young lawyer stood up.

"What is it, Marissa, you're interrupting things, for Christ's sake.

"Imagine what Master John would have done if he'd heard Stu say that...

Forced to eat laundry soap, twenty lashes with a straightened coat hanger...

Stuart began breathing heavily.

It was a terrible habit, profanity.

Marissa, Stu's ever-patient office manager opened the door timidly.

"Mr. Ambrosio, I am so sorry to interrupt you—"

"But?" Stuart roared.

"I told you not to bother me until you found me a competent admin.

The last four secretaries have been completely incompetent." But was that really true?

Stu sighed.

Marissa's lip trembled.

She never had trouble with any of the other guys in the office.

From the mail clerks to the vice president, all were awed by her full lips and bouncing cleavage.

Ah but Mr. Ambrosio was not impressed.

"But I have someone for you, sir!" "

"Oh, God. Another pathetic bimbo?"

Stu was not happy. He'd been in glorious bliss a moment ago...

Marissa waved in a short, very light skinned black man with a hook nose, like his mom was the maid who got raped by the rabbi.

What the hell is wrong with Personnel?

Stu opened his eyes a little widely.

But the fellow looks familiar...

He's an old geezer, about sixty, but there's something about him...

"Who's this? Another slacker, I bet." Stu's voice deepened, in an attempt to awe the newcomer.

"The carelessness of the support staff here!

My Master Pietro once made me lick dust out of a corner that he swept shoddily..

He should be head of Personnel!"

Yeah, and Master Piet whacked Stuart's bare butt with a carpet sweeper.

Yes and made Stuart sleep naked in a dog kennel in July, he was so mad.

Hooknose peered at Stu through thick, mended granny spectacles.

Marissa smiled, trying to explain.

"Mr. Ambrosio, this is Fenton Weir...

He's a trainee from our Save the Streets program... he..."

Stuart laughed harshly.

"You mean the ex-con thing? "

Stu laughed improbably.

"I ask for a secretary and you bring me a half-breed midget ex-convict?

What the hell's wrong with you, Marissa?"

My God, he's not even wearing a suit...

That jacket is from the Army-Navy store.

"I need pie charts done, not to have the office raided."

But the little man wasn't bothered at all by this.

He put his hand on his belt casually, and for some reason this made Stu's throat dry.

Stu wondered why the jailbird needed a belt that thick.

It reminded him of Master Piet's thick strop from New Mexico...oh, how it hurt.

The little Negro Semitic dwarf laughed, and winked at Stu.

"Don't worry, I don't rip off printers, I steal cars...

But I also can type 120 words per minute, big boy, and that should be enough.

Why don't you settle down before someone gets hurt."

Marissa looked at Fenton in horror,.

Yes, but amazingly, when she turned to Stu Ambrosio, the executive was grinning back.

"I guess we can try you out, Fenton..."

"I'm Mr. Weir!" the little half-breed interrupted, and he wasn't smiling.

As Marissa told the typing pool later, "I just left them there... I hope Ambrosio won't fire the little creep until we can get a decent temp here."

Back in the office, Fenton the Felon was a little sickened by the way this yuppie twink was staring at him.

And Jesus, look at the bulge in his pants!

"I—I-before we start work, Mr. Weir...

You know you look quite familiar, sir."

The kid looked over Fenton's shoulder, and then went into his drawer, and pulled out a tattered 1981 copy of LEATHER CHERUBIM magazine.

The kid was laughing somewhat casually.

"I-I picked this old magazine up as-as a joke, you know at a f-flea market...

Yeah, and-and this-this guy, he looks like you, isn't that a laugh?"

The kid, whose crotch now looked as if it were housing an MX missile, shoved the magazine in front of Fenton...

Sure enough, a twenty-five year old shot of youthful Fenton laying it on Howie Kendricks, dead of AIDS now over a decade.

Fenton snorted.

"Ah yes...the Tawse Club...that was a long time ago."

Fenton the Felon looked sharply at Stu.

"You mean you bought this old jerk-book at a flea market because you don't have the nerve to go into a regular bookstore to get one...

Because you're chickenshit."

The kid blushed, and Fenton watched his crotch bulge once more.

Oh, thank God. What would I have done if he'd been normal...

I've never typed, or WORKED in my life.

"So, you horny little bastard...

Isn't this sexual harassment?

Showin' me this magazine. and leering at me like that!"

Fenton tried to look outraged, and had to bite the inside of his cheek to keep from laughing as the kid burst into tears.

"Maybe I oughtta get you fired...and you have the nerve—"

Fenton pronounced it "noive- "

"-To scream at that poor office manager, just because you can! I think I have to punish you, young man.

Unzip your fly and show me that disgusting pecker of yours!"

Now comes the time?

Will he do it?

Either he calls Security and I go back inside the walls, or I'm in for a niiice little situation here...

Fenton breathed easily as Stuart stepped past him, locked the office door, and unzipped his trousers.

Stuart was nearly hyperventilating as he let his cock out in front of his new secretary.

Jesus Christ, what now?

"Hands behind your back, punk."

Stu put his hands behind his back and stood, horribly embarrassed, as his penis stuck out obscenely from his natty trousers.

"Step up to the desk here, you little faggot"

Fenton's voice was full and deep, and Stuart, his heart in his mouth stepped up to his desk.

Yes, and watched in silence as Fenton picked up an thirty six inch steel ruler that Stuart used for cutting spreadsheets.

Fenton gently pushed the ruler through his fingers.

"So you like to objectify your assistants?

And when you don't want to fuck 'em, you scream at them?

You abuse them?

That get you off?" Fenton's voice rose as he questioned his trembling boss.

WHACK! The steel ruler slammed Stuart's penis into the desk. Ooowww...

Stu hadn't even seen that COMING.

He thought that Fenton was just fucking with him a little bit, and had just taken up the ruler as something to toy with...

Fenton looked severely at Stu.

"You are a nasty little faggot...

A sodomizing little faggot aren't you?"

Stu's dick, despite the pain from the steel slashing, was harder than ever.

"N-no! I-I have a girlfriend...

I don't mess with...guys."

WHACK! WHACK! WHACK!

Three times the steel ruler slammed Stu's cock into the desk.

"You're a liar, I bet you've sucked and been fucked, haven't you?"

Fenton asked, as he lit a cigarette.

"The firm has a non-smoking—" WHACK! WHACK!

"(sob) I suppose it's all right if you smoke just one in here."

Stu felt hot tears coming down his face. Damn him.

"So, you've sucked dick, haven't you kid?

You have what we used to call in the Eastern Correctional Facility...

Blowjob lips.

Nice, full, blowjob lips."

Fenton smiled.

"You know what I mean?"

Stu blushed hotly.

He wished he could touch his aching dick.

Fenton reached over and twisted Stuart's right nipple through his shirt. Stuart screamed.

"Come on, Stu...can't you get honest?

By the way, do you have an ashtray in here? No?"

Fenton opened a few buttons on the young man's shirt and found Stu's other nipple.

"Sissy pink, just like Daddy thought...

My girlfriend, she's a D.A., and she has big, big areolas, and I like to put out my Marlboros on them...

Yours are smaller, but I think I can do the same, don't you?"

Stuart shook his head.

Fenton pushed his cigarette into Stu's left nipple, and Stu bit his tongue as the cigarette steamed out on the areola, leaving a vicious red burn mark.

"Eat it." Fenton ordered.

Stuart opened his mouth, and swallowed Fenton's cigarette butt.

Fenton lifted the steel ruler up again.

WHACK WHACK WHACK!

Fenton landed the ruler again and again on Stuart's cock.

"Are you going to tell me what I want to know...

About what a little cocksucker you are?"

Stuart gritted his teeth and the tears streamed down his cheeks.

"I...I've done those things...fellatio and—and—" "Sodomy?"

Fenton asked, trying to be helpful.

"But it wasn't—wasn't voluntary. My Masters—they used to molest me..."

"It was trauma, and I hated it, Fenton...

It. it was abuse."

Stu's dick got even stiffer as he faced Fenton with this falsehood.

WHACK! "LIAR! You liked it!" Fenton screamed.

WHACK! WHACK!

The ruler slammed Stuart's penis four more times into the desk, and he began sobbing softly, and nodded his head.

"Yes...yes I liked it..."

"Loved it, didn't you, Stuart?"

Fenton looked severely at Stu, who was now shaking.

"I-I didn't love it—"

Suddenly Fenton kicked Stuart sharply in the balls, and his young boss fell on the floor, his dick waving obscenely.

Fenton stepped up and jammed the heel of his combat boot on Stu's penile glans.

Then began grinding it into the floor like a cockroach.

"You are a liar, Stuart.

You loved it...and they punished you, I imagine. Very strict, were your Masters?"

Stuart cried out

"Yes! They got my brother—

Oh, oh, aaggh it hurts—my brother and I when we were young, and they—oh—please stop stomping my dick, Sir."

But Fenton kept prodding as Stu continued...

"Oh ...my Masters were so cruel

and I miss them so...my Masters..."

Stuart began crying yet again, and Fenton gently lifted his boot up off Stuart's damaged cock.

He helped the young man up, and Stuart sobbed on the black man's shoulder.

"You just need someone to teach you right from wrong, right Stu?"

Fenton's voice was gentle now.

"You need someone to give you a whipping, boy."

Stuart nodded against Fenton's shoulder.

Fenton pointed to the desk, and Stuart moved to it.

As Fenton's eyes narrowed, the boy unbuckled his pants and pulled down his underpants as well and bent over.

Fenton took the metal ruler and lifted it over the white, trembling buttocks.

"Say after each one, thank you, Master Fenton!"

WHACK! WHACK! WHACK!

The metal ruler landed again and again on Stu's white buttocks, and three times Stu answered "Thank you Master Fenton."

Fenton unbuckled his belt and landed it ten times, and Stuart once again chanted Fenton's credo.

Then Fenton smiled at Stu. "Guess what I have...

I carry it around, because I have to drop in on my little gal at the courthouse to correct her now and then."

Stu felt jealous of Fenton's "little gal". but he forgot as Fenton unzipped the inside of his jacket and pulled out a coiled leather thing.

"This, Stuart is a scourge, named from the Italian scoriada, ultimately from the Latin excoriare = "to flay" and corium = "skin"..

and it's my original, from years ago." Fenton uncoiled it, and Stuart gasped.

It was indeed the short whip in the magazine!

A wooden handle with five leather thongs embedded with little pieces of sharp metal interspersed up and down the tails.

At the end of each tail was a small spiked ball of hard pewter, it appeared.

"Those are the barbs" Fenton said, smiling.

"I bought this in the late seventies, when I was dating a slave girl who is now a Maryland State Senator.

I used to make her howl with this."

Fenton the Felon noticed that the kid was panting, and looking rather excited.

"My Masters never whipped me with anything like that!" he said, almost eagerly.

"Just belts and paddles and broom handles and stuff."

"Well, you've behaved rather badly today, and you know what you need." Fenton said quite seriously.

Stuart was not moving, just closing his eyes.

But his dick was still rock hard.

"That's inappropriate, Stuart...

I'm going to have to quiet your wee-wee a bit, first." Fenton frowned, and Stu blanched.

"No, not my penis!"

But he stood up and held his penis over the desk. Fenton lifted the scourge...

"The scourge was historically a weapon that the Kaierian Warriors from the Tethinrhim tribe used, usually around the head and shoulders."

Fenton said, as if he were a docent at the Smithsonian Museum.

"But we'll have to make do now. SLASH!

The barbed leather strands slammed on Stuart's cock.

One of the spiked balls bounced off Stu's swollen glans, and Stu screamed loudly.

"Stuart...what do we say?" Fenton said in a mild tone.

"Th-thank you M-master—"

Stu was sobbing so hard he couldn't say it.

SLASH! SLASH!

Twice more the scourge landed across Stu's penis, and the spreadsheets on the desk were now covered in spatters of blood.

"Bend over the desk now, sweetie..

You don't have to say anything after I correct you, but you'll get twenty instead of ten if you don't hold still and keep quiet." Fenton said kindly to the boy.

SLASH! SLASH! SLASH!

Stu bit his tongue and gripped the desk.

His buttocks felt as if they were doused with gasoline and matches.

One of the steel balls had hit Stu in the back of the testicles, and oh, how he ground his teeth.

SLASH! SLASH! SLASH!

Stu felt as if he would now have to scream, and Fenton kindly let Stu bite the steel ruler

"Only four more..."Fenton whispered in Stu's ear...

SLASH! SLASH! SLASH!

On the ninth slash, Stu screamed bloody murder.

"Oh, dear...

Oh, that means ten more, plus the last one from this batch."

Fenton said, shaking his head.

Stu burst into tears yet again, but bent over the desk, and miraculously took eleven more from the scourge.

Then there was a noise, a knock at the door.

Fenton curled the scourge up, and made Stu kiss it, and, wiping the blood on Stu's shirt, put the scourge back in his jacket.

The knock came again and then Marissa's voice .

"Mr. Ambrosio? The door is locked. Is everything all right?"

Fenton leaned over and whispered into Stu's ear.

"Here's your chance, queer-boy.

Tell her I've got you as a prisoner.

I'm already a three time loser, you can get me locked up for mandatory life in George W's America...

Unless you are such a wuss that you—"

"Mr. Ambrosio?" Marissa's voice came again, urgently.

"Is everything all right? Is Fenton—" Stu coughed.

"No it's working out perfectly...

He's a perfect secretary, really."

Fenton leaned over and whispered into Stu's ear and then Stu said,

"But...but Fenton is such a brilliant business mind that I want to give him a twenty dollar raise, and we need to hire someone else to type and file.

I'll need Fenton for other important things...

So you'll have to hire an assistant for us!"

Fenton grinned and reached between Stu's legs, squeezing his young boss's testicles savagely.

Stu dropped to his knees, and then Fenton, amazingly, unzipped his own fly, and the boy's blowjob lips did them both proud.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
gentleoneexplorergentleoneexplorerabout 8 years ago
All The Same

Everything you write is about chastity belts although not in this story and brutal abuse to the point of drawing blood. Are you fixated on this as it is not that entertaining and you post several of the same story line in the same days postings. Fortunately you do not post every day. Can you not use your imagination for another sort of story that fits this genre?

Share this Story

Similar Stories

Groomed to Depravity Ch. 01 A college boy's life goes awry on Halloween.in Transgender & Crossdressers
Meghan's Revenge A girl decides on a novel approach to dealing with a player.in BDSM
My VideoChat Error Ch 01 Shaun gets blackmailed.in NonConsent/Reluctance
The Basement Ch. 01 The opening to a forced feminization story.in Transgender & Crossdressers
Working the Holidays Classic Christmas tale of blackmail and forced feminization.in Transgender & Crossdressers
More Stories