The Boss Ch. 01

Story Info
The Boss is very 'anal' about the female working conditions.
3.5k words
4.3
172.1k
86
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
lordodie
lordodie
840 Followers

Chapter 1: Monday Mornings

Monday mornings always sucked. This morning was worse than usual however. My head still hurt from imbibing way too much alcohol over the weekend. I hadn't drunk so much that I blacked out since I was a 19 year old corporal and stationed at Fort Hood, Texas; over a decade ago. I guess it just goes to show that sometimes a guy never learns.

I tried to ignore my lingering headache and focus my attention at the task at hand. Following my usual morning routine, I was making the final adjustments to the large butt plug that would work Mandy's veteran asshole for the rest of the day. Mandy was my personal secretary. She was a cute, mousy, little blond in her early 30's. You know the type: Bubbly personality. Terminally flirty. Every guy at the office's wet dream. I'd been plugging up her ass for years, ever since we discovered our mutual love of the gaping female nether hole over a few too many beers at the bank's Christmas party some time back.

"Mr. X, would you mind finishing up? I need to get the Franklin account filed before lunch," Mandy asked politely as my mind wandered again. She was bent over my desk with the skirt of her suit thrown up over her back while she reached around to pull her ass cheeks apart helpfully for me. I had the three inch by twelve inch rubber dong about half way up her bum when I had gotten distracted with thoughts of my old military days.

I didn't approve of normal butt plugs. In my very learned opinion, the tapering at the neck allowed the sphincter to relax and defeated the entire purpose of the exercise. As such, I preferred dilator plugs that either were a consistent thickness along the entire length or even got wider towards the base. Of course this required rubber or leather panties to be worn to keep the plugs in, but that was a mute point; she had to wear panties anyway, didn't she?

"Sorry Mandy, here you go," I apologized as I forced the remainder of the plug into her bottom. I massaged her well toned ass cheeks as she gasped in surprise and tensed at the unexpected violation. "I trust this is to your satisfaction?" I asked as I pulled up her leather panties, situated them around her waist and attached the tiny padlock at the small of her back, locking the plug in her ass until I took it back out just before we left for the day. The lock was unnecessary as she would never take it out without asking, but we both enjoyed out little games together and the added aspect of submission really got her juices flowing. Sometimes I was a little jealous of her boyfriend Jeff as she was usually so hot and bothered by the time she got off work that he was the one who got thrown onto the bed and fucked when she got home, not the other way around.

"That's just about right. Thank you Mr. X," Mandy said as she stood up and smoothed out her pin striped skirt over her bubble butt. She would be moving around the office all day with that large plug shoved up her backside while most of our coworkers would be oblivious to the plight of her straining sphincter and well stretched lower intestine. "Although, over the last week or so, I've really started to be able to get around without much discomfort. In fact, I almost forget I have this in me sometimes. I think we may need to step my butt up a size or two tomorrow," she said mischievously and grinned.

"I think that's a lovely idea, Mandy!" I responded. "Why don't you take the petty cash credit card down to the boutique over lunch and buy a few more appropriately sized models and we'll try them on for size tomorrow morning. Just to make sure we have enough time for a proper fitting, clear my schedule from 8:00 to 9:00 tomorrow morning. That should give us enough time to properly pack your hole. I'm thinking something around three and a half inches wide and maybe sixteen inches or so long. Use that as a baseline but get whatever size you think will make you feel most uncomfortable but still allow you to get you job done."

"Of course, Mr. X. That sounds perfect," she responded as she headed for the door, ass swaying provocatively as she did. "Oh! Don't forget, you have a 10:00 AM with Mr. Bixby from City Mutual and an 11:00 AM lunch meeting with Mr. Stevens from corporate." With that she was out of my office and back to her duties.

Damn! I hate it when she leaves but I love watching her go!

***

I looked at my desk clock; it was already 9:20 and I was getting too annoyed for this early on a Monday morning. Or at least I should be. Janet's till from Friday had come up five cents short. Again! This was a reoccurring problem with the girls who worked the drive through window. Despite my extraordinary leadership and motivational abilities -- and I have the corporate certificates and impressive looking awards framed on the wall to prove it -- those girls just kept misplacing money. A nickel here. A dime there. I swear! If it wasn't for me covering for them they would have been sent packing years ago! Of course, I had reviewed the security tapes from last week and I'd watched Janet deliberately open her drawer, pull out a nickel, and drop it down her abundant cleavage; all while looking at the camera and smiling mischievously. A good manager's job is never done I guess.

I opened my lower left desk drawer to retrieve my 'Teller Correctional Panties', as I liked to call them. They were something of my own invention. They looked a lot like a normal garter belt at first glance, but that's where the similarity ended. A garter belt went around a woman's waist with straps hanging down and ending in clips to hold up stockings, but these panties were slightly modified. The straps that hung down did not end in clips but small metal hooks. They were designed to be inserted into a woman's anus and pulled tautly outward forcing the most delicious gapes. I'd dubbed them 'Gape Panties'. I'd tried to sell the design to a few lingerie companies but it seems that the world just isn't quite ready for models to walk down the Paris runway while reporters and socialites examine their colon health from the comfort of their seats. I guess I'm just ahead of my time.

I walked out of my office and passed Mandy's desk on my way to the drive through tellers' booth. She was hard at work surfing the web for the latest in butt busting paraphernalia and nodded politely at my passing. I glanced at the screen long enough to see she was on a page that catered to gay men with a similar anal fetish; tomorrow morning should be fun, I thought to myself.

As I reached the locked door to the drive through tellers' booth I banished all traces of a smile from my face and put on my best disappointed frown; back to business. My key card allowed me access to the booth and I stepped inside. Only the two tellers who worked the drive through, Mandy and myself had unfettered access to this part of the bank; a fact which allowed me a certain freedom to choose only very qualified women for the teller positions back here.

"Good morning, Mr. X," Janet and Mai said in unison as they glanced at me from their positions. While Janet was a slightly older red head in her mid 40s, Mai was much younger lady in her later 20's and of Japanese descent. Both women took care of themselves however, and my dick hardened at the sight of them. They were both naked from the waist down, save for garter belts, stocking and heels. While such a dress code would have been scandalous at any bank in the world, they got away with it because the outside wall came up to their chests and hid their lower bodies from our customers. No one inside the bank had access to their booth that wasn't already in on their unorthodox dress code, so they couldn't be surprised by their coworkers either.

The only two seats in the room were two tall stools on which they would sit. The stools themselves were normal; the large cone shaped plugs mounted to their tops were not. The cones were wide enough at the base that there was no way that their butt cheeks could ever actually touch the stool's seats, but that was the point. At the moment, Janet was sitting down attending a customer while Mai was standing at the back of the booth filling out paper work. Mai turned slightly, without interrupting her work, to give me an excellent view of her dilated and gaping anus. Japanese Henti artists had at least one thing right: The sight of a beautiful Asian girl with an obscenely gaping anus was a truly magnificent form of art!

I walked up beside Mai, pretending to inspect her work. My hand, as nonchalantly as possible, found her shapely ass cheeks, squeezed it once and then disappeared up between those same shapely ass cheeks; her sphincter quickly adjusting itself around my wrist. Mai, to her credit, barely registered a flinch.

"Have a good weekend, Mai?" I asked.

"Not too bad, Mr. X," she responded without missing a beat. "I was visiting my parents up state all weekend. Needless to say, I'm glad to be back to work. They do get very tiresome."

"Parents can be like that," I responded starting to pull my hand out slightly until her young sphincter was tautly stretched around the largest part of my clenched fist before allowing my hand to be sucked back into her needy body. "I don't go home much for that very same reason." I took up a slow, steady rhythm of fisting her ass as she continued to appease the bureaucracy. I waited for Janet to finish up with her oblivious customer: A cranky old lady who wanted her check cashed with this many $20s, that many $10s and the rest in rolls of quarters. Who the hell needs $50 in quarters in the 21st century anyway, I asked myself. Finally, Janet finished up and the cranky old lady drove off.

"Would you mind putting this on hold for a few minutes while I have a word with Janet?" I asked Mai, regretfully extracting my hand from her softly convulsing anus.

"Certainly, Mr. X," she responded regretfully. The slight flush on her cheeks, the ones on her face not below the ones below her waist -- stay with me here people -- the only noticeable telltale of how much she was getting into her impromptu anal fisting session. She glanced quickly out of the thick bullet proof window to ensure that no customers were waiting before bringing my soiled hand up to her lips to clean off my fingers. Her eyes never left mine as she moved from one finger to the next; ensure each one was sparkling clean. It never ceased to amaze me how much suction the young woman could create with her mouth. It was one of her most admiral talents. Too bad it's not the kind of thing that would be acceptable to place on a resume.

Finished with her task, she returned to her seat. Mai lined up the cone shaped plug under her recently vacated rectum and lowered herself down. The muscular ring opened up like it was accepting an old friend, which it most definitely was. She pulled her feet up to the highest set of bars on the stool to place her full weight onto her ass's outer ring. She then took a few seconds to reapply the thin straps of Velcro that held her ankles to her thighs before her next customer pulled up to her window. Mai began talking to her new customer with no outward signs of the amount of stress that she'd just willfully placed her talented nether hole under; she really did love the dress code at her job!

I took a step over to Janet as she turned on her stool to face me. The stool itself didn't turn; she merely allowed the oversized cone violating her back hole to rotate 180 degrees around the inside her straining orifice. She had a knowing look in her eye.

"What can I help you with, Mr. X?" she asked. I sized her up, like I always do when she's in this position. Her natural FF cup breasts were almost busting out the top of the almost-too-revealing-to-be-appropriate-in-a-business-environment silk blouse she normally wore; possibly the source of the aforementioned cranky old lady's crankiness. However, most of the male customers, and even some of the female ones, appreciated the view very much and so no one ever said anything to her about her choice of tops.

Just below where her blouse ended her engorged and dripping pussy lips were clearly visible, as was the lower part of the cone shaped plug prying apart her well worn asshole. My eyes traveled back up her body in a most unprofessional manner to meet her eyes once again. I banished the smile that had formed on my face and put my best disappointed frown back on; the one I had put on earlier before getting distracted with Mai. My momentary lapse in sternness did not go unnoticed my Janet, but she didn't comment on it. What good is her pretending to screw up, and me pretending to punish her, if we don't play our preordained rolls?

"It seems that your till came up short again last Friday, Janet. This is your seventh discrepancy this month," I said seriously. Janet's face showed sudden bewilderment and she cast her eyes down, right on queue.

"Ooooh! Busted!" Mai proclaimed from behind me.

I turned my head around to look at Mai briefly to reprimand her. "And your record is none too brilliant either Ms. Zhu. I suggest you attend your customer and leave the employee correction to me: The manager. You know, the guy who makes the big bucks to make sure that you two still have jobs tomorrow," I said with a slight twinkle in my eye. Mai, looking properly scolded, found something else to focus her attention on; I'm pretty sure it was more the wiggling of her hips to force the cone further up into her ass than it was the impatient looking man in the pickup truck at her window.

I returned my attention to the errant teller in front of me, "Here at Town Bank we do not condone or tolerate sloppy money handling; this is a bank after all! I'm afraid you leave me no choice but to apply corporal punishment or to put in the paper work for your position's immediate termination. It's your choice. Which is it going to be?" I already knew the answer before I even asked the question; it's the same ultimatum I give her once or twice a week.

"I'm sorry sir, I guess I need reminding again," she answered without meeting my eyes. "I do get too sloppy at times."

"I assumed as much," I responded, knowing that the sloppiness she was referring to was not the sloppiness of her work. It was a far more accurate description to the dual holes between her legs and buttocks. "Go ahead and stand up and let's get you into your 'Teller Correctional Panties'," I commanded.

She meekly stood up, stepped to the side of her stool and bent over the counter slightly. I kneeled down behind her, holding up the gaper panties so she could step into them with practiced ease. After I had secured them around her waist, I seated the hooks into her still gaping anus. Just standing there her ass must have been gaping at least three inches across!

"Just remember: This is going to hurt you a lot more than it's going to hurt me," I said I as I stared to pull the straps tight. Janet closed her eyes and whimpered as the straps were drawn outwards forcefully; her bright red rosebutt opening up like a flower in blossom in the spring. I continued to pull and tug at the straps as hard as I could until the gaping chasm between her butt cheeks was over five inches in diameter. Janet was shaking slightly with a tear or two in her eyes by the time I'd finished.

"Now, hopefully you'll do better in the future," I said as I admired the view. I could see right up into her guts for almost a foot; a foot of intestine and beyond that I knew well enough to be her proctologist. I could have stayed there for hours admiring that beautiful distended anus but I had other duties to attend to. Standing back up, I placed my hands on Janet's shoulders and guided her tortured asshole back over the large cone on top of her stool. I pushed downwards and she sat obediently, allowing her punished sphincter to wrap itself around the majority of the cone shaped plug once again. I leaned down to once more admire my handiwork and noticed that Janet's asshole had become so dilated that her cheeks were now less than an inch from actually touching the seat; the additional force of the Teller Correctional Panties assisting the plug to force her asshole to almost five and a half inches in diameter. I made a mental note to have Mandy pick up the next size larger cone plug for Janet's stool when she went shopping over lunch. I should probably go ahead and have her pick up a larger one for Mai also; I don't like playing favorites after all.

"Now that that little bit of unpleasantness is done with, you ladies have a productive day," I said heading for the door. "Janet, come see me in my office sometime after lunch once you think you've been properly chastised." She nodded wordlessly.

"Oh, just one more thing before I forget," I said turning away from the door and walking up to stand behind Mai. Picking up a random sheet of paper on her counter and addressing the young Japanese girl, "be sure to get a copy of this on my desk before lunch." The actual form was irrelevant. In fact, I had no idea what it even was. It was just a nonchalant way for me to put my hand on her shoulder and press firmly downwards; this added fifty or sixty more pounds of body weight to her already tortured anal sphincter. I was rewarded with a soft squeak from Mai as she sank farther down on the widening cone by at least another inch.

"Of course, sir," she responded pleasantly after only a few moments hesitation to regain her composure. "Would you like to continue our conversation on bureaucracy that we already started over lunch? I'm sure your knowledge on the topic is 'large' enough to 'fill' any questions I may still have," she said with a sly grin.

"Unfortunately, no. Not today," I responded with heartfelt regret. Mai looked noticeably deflated. "I have a lunch meeting that will probably run long. And I don't expect it to be anywhere near as satisfying as our usual lunch time conversations. Perhaps Mandy can free up some time on my calendar this afternoon. Give her a call and see what she can move around."

"Yes, sir! I'll be sure to do that," Mai said cheerfully. That girl's insatiable lust for all things anal never ceased to impress me.

Finally taking my exit, I closed the teller booth door and headed for my office. I knew I wouldn't see Janet again to remove her 'Teller Correctional Panties' until it was closing time. Since she made a point to intentionally screw up and be forced to wear them, she had no intention of shortening her sentence.

God! I love my employees sometimes!

As I passed by Mandy's desk, she stopped me with a raised finger. "Beth Johnson is holding on line three for you, sir."

"Thank you, Mandy. I'll take it in a minute," I said as I walked into my inner office.

It's good to be The Boss.

lordodie
lordodie
840 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
7 Comments
Gym52Gym524 months ago

An erotic short story without any real intercourse, enjoyable!

TheSodomiteIslesTheSodomiteIslesalmost 6 years ago
Please please please continue this story

This is one of my favorite stories on this entire site it's honestly amazing

blueeyed38bbwblueeyed38bbwover 7 years ago
Good story needs an editor

The story is good, but an editor is needed to correct the grammar errors.

AnonymousAnonymousalmost 8 years ago
Chapter 2?

I'd really enjoy a second chapter, this was fun and sexy. I really enjoyed it, as I've enjoyed everything else you've written

AcungaAcungaabout 10 years ago
i tried write something like this

But it takes tons of energy plus i dont speak good english. Something that pictures itself in my head for half a second takes 30 minutes and many words to explain in words :( . So anyway here is my story, japanese woman mai tries to escape being tied up and probed in ass and urethra and ends up tying herself more going throuh some shit involuntarily dialating more. Rest is up to your imagination :)

Show More
Share this Story

Similar Stories

Caroline the Teenage Bum Slut Caroline at school, the doctor's, and home as anal slut.in Anal
Anal Etiquette: Madrid Extreme anal is the new normal in a future Spain.in Anal
Outsourcing His shrewd wife taps ready young coed for booty duty.in Anal
I Bet You'll Like It His roommate is sweet, cute and she's into butt stuff...in Anal
More Stories