Busty Secretary in Trouble

Big Breasted Secretary spanked and caned by her Big Bad Boss

Nineteen year old Stephanie Tweddle was in big trouble and she knew it.

Glancing up from her desk, she could see through the glass partition Mr Thompson, her boss practicing his swing as he waited for her to knock on his office door at the stroke of 5pm sharp.

"Oh heck!!"

The ticking of the clock got louder and louder as the seconds passed more quickly than she thought possible until...

Ding dong, ding dong.

Five O'clock had finally arrived. With her belly doing flip-flops and her ass cheeks cringing with fright, Stephanie got to her feet, put the "Size 6 to 10 inches deluxe battery operated model stock list" file away in its correct drawer and reached around to smooth the material of her tight checkered tartan skirt down as she made her way to his office.

Rat-a-tat-TAT!!

At the sound of the rap, Laurence Thompson, owner and proprietor of Thompson's Erotic Enterprises looked up and smiled as he saw the shadow of his secretary through the glass waiting for her caning.

Ah...Miss Tweddle.

From the moment he interviewed her for a job all those months ago when she wobbled in wearing a tight black skirt with an even tighter white blouse hiding what were undoubtedly an enormous pair of tits, he knew that she was the secretary for him, even with her lack of experience. Truth to tell, he couldn't keep his eyes of her massive melons as she sat before him biting her rosy lips and fiddling with a stray strand of her long fiery red hair.

At first he smiled, ignoring her mistakes with a "don't worry my dear, you'll learn." hug before giving her rather splendid ass a wee pat that made her squeak and giggle in surprise. In fact come to think of it, she didn't seem to mind his little indiscretions at all!!

Perhaps she thought them a small price to pay for him keeping her on in spite of her increasingly frequent boo-boo's. But unknown to her Mr Thompson had other idea's, for in his quiet moments he was a connoisseur of the female form and quite enjoyed having a young lady to chastise on the odd occasion though even as a confirmed bachelor in his mid-forties those opportunities were rare indeed and invariably were with the begrudging assistance of "handsomely paid ladies of the night" who were not into it at all...

"Come in" he called as he sat back in his leather chair.

The door creaked open a bit and the pensive face of his secretary peeked round it.

"Yes.? " he sighed, enjoying the moment as he always did.

""M..Mr Thompson?" she stuttered licking her upper lip with that dainty tongue of hers. "I..I'm here for my c..caning Sir."

He motioned for her to enter and close the door behind her.

"Right Stephanie, lets have these frilly things down shall we, then you can bend over the desk and we can make a start okey-dokey?" he ordered standing over her and flexing the thin rattan between his hands before bending it into an arch that had the quivering girl boggle eyed in fear. Having discarded her skirt, she reached behind her and slipped her slender fingers into the waistband of her black french knickers before with a swivel of her wide hips easing them down to mid-thigh.

"Splendid my dear, now...you remember what we said last time I caned you?" he asked as she stood before him with downcast eyes, hands clasped in front of her fanny trying to hide her soft puss before his leering gaze.

Said?

Last time?

Oh..OH!!

"Oh my...he doesn't want me to do that now?! "Wh...what, here now Sir?" she squeaked, swallowing hard as he let the tip of the cane go, and stared in morbid fascination as it wobbled and waved before her red face. "Oh please Mr Thompson I don't think I should," she hiccuped shivering, knowing that he would brook no argument from her.

Folding his arms, he shook his head. "A proper big girl punishment will do you good Stephanie, so come on... off with your blouse this minute and hurry up for I haven't got all day girl!!" he indicated, pointing to her white garment.

"Oh Sir..." she pouted as with a sigh, she reached up and began to undo the small white buttons on her tight white blouse with her boss watching her striptease with his tongue poking the inside of his right cheek in rapt admiration as she wobbled and wriggled before slipping off her garment, folding it and placing it neatly on the chair beside her. Beneath a mass of hair, she glanced up at him with the question hanging between them.

He nodded.

So, taking a deep breath she reached behind her causing her over-developed encased boobs to thrust out towards him as she fiddled with the fiddly strap until...

Boing!!

Her bra fell away causing each massive bouncy balloon to spring free before she reached across with an arm to try and hide them from his gaze which, in the circumstances was nigh impossible due to their impressive size and fullness as the flesh oozed over her guard.

"You're such a bad girl, Stephanie," he said as he bent down to pick up her bra from the floor, taking the chance to admire her pretty, shaved pussy.

He examined the tag and shouted, "34J, what the fuck is that? Were you trying to get to the end of the alphabet? I knew you were a bad girl but I didn't think you were this bad! I imagine these grotesquely overgrown funbags are not in any pain. That is unacceptable! My god, I'm going to have to hurt you so much for that!"

"W...wouldn't you rather s..ser..spank my bum Mr Thompson like you did the last time I made a mistake..peeeeer..pleeease?" she sniffled as she saw him tapping the cane on his palm.

Mr Thompson smiled to himself as he remembered the first time when he called her into his office after she had made one costly mistake too many to ignore.

"Sack?" she gasped as she sat before his desk, her surprise writ large over her pretty face.

He nodded. "I'm sorry Stephanie, you're a lovely lass but you just cannot keep making mistakes like you've been doing sweetheart...I'll pay you up for the rest of the week but I think its best if we call it a day." he explained, feeling awkward as he liked her a lot and not just because of her obvious charms. To his dismay, Stephanie started to sniff and sniffle as she bowed her head and fiddled with the hem of her black skirt.

"I..I thought I was doing alright Mr Thompson even though I can be a bit of a scatterbrain at times and forget things you tell me to do..but but...please don't sack me Sir..cos..cos..." she hiccuped and looked up at him tearfully in faint hope. Reaching over the table he handed her his hanky to dry her eyes.

Scatterbrained!! That was one word for it, the evidence was piled high in his stockroom due to her last boo boo, stack upon stack of cardboard boxes stuffed with "Rita Rectum - an ass fucker's dream come true...and she never says NO!!" blow up dolls that reached to the bloody ceiling!!

He shook his head. "I'm sorry Stephanie...it just hasn't worked out." he smiled apologetically.

"But..but you don't understand Sir, my dad will go ballistic when he finds out I've been sacked and he'll...he'll.." she whispered as her face went white.

"He'll what?" he asked, curious in spite of his resolve as to the reason why she was so upset and flustered.

Blinking away her tears, she looked down at the floor and bit her lip wondering if she should say anything - family secrets and all that, but she knew she had to try and keep her job or she'd really be in for it when her dad got home from work.

"He'll..well, its..its see he's ever so strict is me dad Mr Thompson an' he goes mental if I get into trouble and all...so if you give me the sack fer being so daft, he'll blow his top and he'll...spa..er..spank me an' an' he has this big leather belt an' he'll probably use that on me bum as well!!" she whispered, blushing to the roots of her red hair as the tears dribbled down her rosy cheeks.

Spank?

Belt?

"He spanks you?" he asked shocked, his mind working over-time as his heart bounced around inside his chest as he listened to this young lady reveal her part innocently in a secret fantasy fetish of his.

"Yes Sir, really really hard an' all." she pouted as she watched him sit back in his chair and tap his fingers together as if re-considering sacking her. She smiled hesitantly at him, perhaps he was going to think kindly on her and not let her get into trouble with her father...after all he did give her the job in the first place even though she had no experience or qualifications for the post.

But Mr Thompson had other ideas. He sat forward. "Stephanie, I have a proposition to put to you which may help us both er...come to some sort of satisfactory arrangement...if you're willing that is." he began.

She nodded her head enthusiastically. He wasn't going to sack her!!

As she sat listening, her boss smiled and outlined what would be required of her for him not to dismiss her but as he continued her joy turned from outright relief, to a furrowed brow of bemusement, puzzlement and finally, as the penny dropped her mouth fell open when he finished by saying...

"So Stephanie, if you want to keep your job you have to let me spank you after every mistake and if you've made a really, really big one like ordering 500 blow up dolls instead of 50 well, I'm sure I can find something other than my hand to use on your bum, so what do you think, do we have a deal?" he finished sitting back and grinning at her like the cat who got the cream.

Stephanie just sat staring at him dumbstruck with big round eyes, but in her heart of hearts knowing it was either get the sack and get a thorough walloping off her old man or submit her fat bottom to Mr Thompson instead and keep her job. Talk about "out of the frying pan into the fire!!" She stuck out her tongue and licked her upper lip as she glanced down at his hands. Big hands. Oh heck!! But she knew that he knew that she knew she was in serious poop and that she had no choice in the matter. for anything would be better than her dad finding out!! "Alright Sir," she sighed, resigned to her fate, "...if you promise not to tell my dad you can spank or belt my bum every time I get into trouble."

"I won't tell you again Stephanie, lean over backwards. Go on spread your legs apart and stick up your fat tits higher or else I'll spank you before I cane you!!" ordered Mr Thompson as he smiled at the memory of how they had both come to this pass. He bent over and held a tit up to his mouth, sucking and kissing. He tasted the salt of the fear induced sweat covering her body.

Stephanie's fear, the cool air in the room, and her boss's licking were eventually enough to get a response from her ***** nipples. They pulled in the surrounding skin and tried their best to stand up tall. Rising to his full height, he took Amy by the jaw and looked directly in her face.

"How dare you make your nipples hard! Still trying to draw all the attention to your tits, aren't you? I was trying to give you a little time to prepare yourself for your first breast punishment but now I see how you repay kindness. You're in big trouble now!"

Mr Thompson fetched a metal ruler from his desk and put the cane down on the table beside the trembling girl. Bracing against the cool wood of his desk, she wiggled her prominent tits, and arched her back more causing each massive globe to spread out over her chest.

"Ready my girl?" he asked as he reached down and pinched the sensitive tip of her distended nipple and twirled it all the way around, before letting it jiggle back to the center of her youthful elastic breast. All his naked secretary could do was squeak and tremble in half fear and half arousal, momentarily forgetting the dire fate about to befall her glorious globes.

The ruler was about an inch and a half wide with rounded edges in order to prevent cutting. Stepping in front of Stephanie, to the side, Mr Thompson lined up the first blow. Pulling back the ruler while she stared wide-eyed, he swung into her tits, hitting her flat across both nipples. Her reaction was wonderful, thrashing and screeching and making as much noise as possible while a wide red stripe appeared on her oversized tits.

Knowing that his secretary's voluptuous tits would be in some sort of pain from this moment on made him hard as a rock. He grasped a handful of her hair and repositioned her in front of him. He gave five more strokes to one nipple, then five more to the other, causing more thrashing and desperate grunts from hapless girl. Looking the pretty young woman directly in her eyes he asked, "You're such a bad girl, are you even sorry for what you've done?"

"I didn't do it on purpose. Please, I'm not bad. It hurts so much, just stop hurting me."

Stephanie continued to beg, repeating herself often, while Mr Thompson deftly rolled her discarded panty into a ball gag. Forcing it home and buckling it tightly with her bra, he told his new toy, "You've failed in your duties again and again. I was right, you are a bad girl. I could tell the moment I saw you. You are going to suffer for your sins."

With that he resumed the punishment of her breasts with the ruler, working over the upper slope of her bosom. He moved on to the sides and then to the smooth curve at the bottom. As he worked he often went back to give several strokes to her nipples. Her screams around the gag were music to his ears.

When the huge mounds of flesh were nicely covered in a pretty dark pink shade, threatening to become red, he could hold off no longer. He grasped her hair and pulled her down and around to tilt her head back while facing away from him. Then he shoved himself down her throat as he smacked her across the nipples nonstop. He came hard, his paintoy secretary's tongue lapping at his balls.

He reluctantly pulled out of her mouth, allowing her to breathe deeply. She'd learned all of his preferences over the last couple of months, under threat of more spankings, of course. She was trying to be such a good girl.

"Stand up girl, that was very good. Tell me, how do your tits look to you?"

Carefully avoiding eye contact, she answered, "Red, Sir."

"Yes, isn't it a beautiful shade? I always pause to admire the view when your bottom turns that color. Are these ridiculously large tits that same color everywhere now?"

"No, sir."

"Where is there a different color, Cunt?"

"S..Sir, my nipples are darker. Oooh, they hurt so much."

"And what else is different in color?"

Stephanie looked perplexed, then realized with horror that the bottom part of her globes hanging against her chest hadn't been beaten.

"The bottoms of me breasts, S..Sir."

"Tits, Cunt! Tits! Never call them breasts again. Now help me take care of the undersides of these enormous meat bags, will you?"

"B..But please Sir. Haven't I suffered enough."

"Stephanie, you deserve nothing but punishment for your many transgressions. While there are so many reasons to discipline you, your worst crime, by far, is having these huge tits. I am going to hurt them very badly. You must never experience another moment in which you do not have sore titties. I will torture them whenever possible. Their pain will be a constant reminder to you to take more care in your work. Do you understand?"

"Ye..Yessir," Stephanie stammered with a shudder.

"Good! Now hold this tit up by the nipple so I can paint the bottoms."

Stephanie winced yet again as she pulled up her own nipple until the entire breast was lifted. Mr Thompson proceeded to beat a steady rhythm on the stretched skin, now so vulnerable to his perverted affections. The poor girl thrashed in pain but held tight, knowing the penalty for letting the heavy mound of flesh fall would only redouble his brutality.

After finishing with both tits her boss grabbed one of her breasts and sucked hard on the nipple. She screeched through her teeth and he let go.

"You enjoyed that so much earlier, I guess you don't feel the pleasure in your udders now. I think you need to thank me for showing you the error of your ways. You'll give me a long, sexy kiss. If you don't show me how much you appreciate my lessons or if you say one fucking word I will beat those giant udders with this ruler until I'm too tired to swing my arm. And then I'll start with the cane."

He reached behind the terrified girl's head, and brusquely jerked her into him. Stephanie was too scared and hurt to put any real passion into kissing but she knew she was expected to put on a show. She tilted her head slightly and pressed her lips against those of the fearsome man grinding into her. She kissed him gently, like a caring lover. His tongue slowly slid over her pursed lips before pressing between them. She closed her eyes and opened her mouth to him, letting him take control of her mouth, his tongue entwining with hers.

He slowly ended the kiss and hugged the tortured girl tightly to him. Stephanie's tits, warm from the punishment, mashed against his lean body. He kissed her neck and whispered, "You're such a bad girl."

Mr Thompson enjoyed the display of forced passion. He was slightly disappointed in her lackluster participation but he knew there would be plenty of time to train her for that. Now he was more interested in moving on to the next implement.

"Back on your knees, Cunt, where you belong."

When she was kneeling once again, he returned to the table and traded the ruler for the cane. Upon realizing that her breast beating was about to start again, Stephanie let out a wail followed by,

"Oh god, no! You can't! I can't take it, please! I'm not bad, I'm not, I promise! I'll be good, I will, I'll... I'll kiss you, and suck you, and fuck you any way you want. Please! My boobs hurt so AHHHGGG!"

Her boss cut her off with a stroke across the top of both tits. Since she clearly wasn't a fast learner he again shoved the wadded panties into her face hole and buckled it even tighter than before. For this part of the punishment he made her join her wrists behind her back and hold them there. Then he forced her to lean forward, her tits hanging slightly away from her torso.

Licking his lips, Mr Thompson bounced the business end of the cane across her reddened breast globes to measure his aim, then bracing his feet slightly apart he reached back and with a full bodied, wrist snapping swing let her have it right across the peaks of both mounds with a resounding CRACK!!

"N..noooooyeeeeeeoowwwww MR THOMPSON SIR!!" shrieked Stephanie as she felt the bite of the stick sink deep into her mammary fat and the wash of white hot, red branding pain wallowed and waxed out from the epicenter of her torment. The blow had knocked her backwards over to the desk and she scrambled on her knees to get back into position as she gritted her teeth and swung her hair trying to shake off the awful sting that was radiating up her spine and setting off fireworks in her head.

"Ohhhhhhmmmmmmhhhhmmmmmmoooooowwww don't cane my poor tits so haaaaaaard Mr Thompson, ohhhhhh it stttttttttings sooooo!!" she gasped, knowing that by the end of her caning she was going to have a canvas of painful bruises on each of her treasured globes that would constantly remind her of her predicament and add to her misery.

Mr Thompson was pleased to note that even though the first stroke had been a biting, cutting and very hard one she still returned to her position bent over, not caring that she was showing her pulsing pussy and bumhole to the rest of the world.

"Cunt, use you fingers to get your pussy wet. I don't care if your pussy is creaming or if it's full of your saliva but I'm going to be hard after caning your pain sacks and I'd better slide right in."

Stephanie positioned herself carefully on her knees and went to work licking her fingers and strumming her pussy lips and clit. Her attention was completely taken off of that though when the next cane stroke came up from under her and lifted her breasts up with the impact.