Sheila is The Big Boss's Hot Date

Story Info
There's No Turning Back.
2.4k words
3.4
9.4k
7
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

Willy Nellie's Games, Inc., a manufacturer of family board games, has grown so much the last year that President & CEO, Steven Carlson, can no longer fit everyone in across the street at the Velvet Turtle for their annual company anniversary party. But he doesn't want to spend the money to rent a bigger venue. His new Executive Secretary, Sheila Warren, comes up with an idea. How about they have every employee come with a new 'date', who is a fellow employee? Thus, the number of attendees to cater for would be half as many as it would be if outside spouses or boyfriends/girlfriends were to attend.

This unusual idea caught on quickly in the management's inner circle for largely self-interested reasons. Sheila herself was happy to take her chances with almost any random man instead of enduring the boredom of her doormat of a husband. Mr. Carlson himself had a similar motive and fully intended to ask (tell) Sheila to be his 'date'. Not that he was remotely hoping to get kissy-facey with her, but simply because he has been getting uncomfortable in his trousers several times a day just peering over her shoulder at the finest female form on the 8th floor. He would dearly love to take her in his arms for a night of dancing.

Two other top executives had pretty much the same thought in mind, although they were savvy enough to know the big boss would be gobbling up Miss 'Big Boobs' as his own date and they would have to settle for a few dances while the gorgeous Mrs. Warren's husband was not on hand.

Together they comprise a majority of the full Executive Committee so Carlson informed Sheila that her idea had won their hearts and for her to get word to staff orally, no memo, to poll them on the "Sheila Plan" for the party.

He took that moment to lean over and quietly inform her that she would be HIS date for the event. She smiled, a most genuine smile since that is what she had hoped for when she came up with the crazy idea. She knew, in the way that women know these things, that her handsome boss has a boner for her, which should make for a lot of fun. No remote way Shiela was going to allow dream-boat, Mr. Carlson, to 'date' any other female to the company event.

Staff members were asked to check back home and let Sheila know if they were ok with the novel plan. A clear majority had responded YEA before that day was over. Sheila and President Carlson speculated that meant they had not even bothered to ask their spouses/sweethearts for input on the new dating scheme.

A clear majority were ok with these faux dates because they had been bored to death with previous company parties. A smaller number may have been interested because of their attraction to a given fellow employee, but there was no way to know much more than speculation on that score.

Many spouses back home were quite happy to give the party a pass for the same reason, deathly boring prior experiences. A relative few grumbled about the idea, perhaps with fears about their spouse's potential to get into trouble. A small number flatly said their spouse could simply not attend under the "Sheila Plan". As responses drifted back to Sheila she caught the gist that probably most employees had simply glossed over the fact there would be office co-worker 'dates' involved and simply told their spouse the party would be for employees only this year.

Of course, some of the less self-confident staff ladies feared they would not get an invitation, but the President announced it would be Sadie Hawkins's rules so the ladies could ask out gents if they wanted to.

Pretty Chelsea Seaman, from the Telephone Sales team, was 29 y.o. at this time. Married almost 10 years with two grade-schoolers at home, she was pretty charged up over the new plan for the company's Anniversary Party. While she very much loved her hubby, a night out with him was as exciting as a bologna sandwich with no mayo or mustard. There were a couple of nice-looking coworkers on the Telephone staff and she was sure either one could provide for a much more interesting night out. Hopefully, MUCH more interesting.

Chelsea went up to beefy Will Marin, who she thought had been a noticeably good dancer at previous events, not to mention handsome as the devil. She asked him if he had heard about the new 'dating' plan. Will almost jumped with enthusiasm and immediately asked her if she would be his 'date'. Having hoped for exactly that response, Chelsea rather casually allowed as to how that might be a good plan.

Date night pairings were quickly arranged around the office but, since 56% of the staff were male, there was an obvious problem, which Sheila pointed out to her boss. "Mr. Carlson, it's all my fault." She thought it was the diplomatic course to blame the oversight on herself. "I simply overlooked the fact that significantly more than half of our employees are men, so some of them won't get a date this way."

Steve pondered that for a minute and then offered his executive solution. "Well, we will call it a Sadie Hawkins Night, so any kind-hearted Sadie on board can invite two dates if she finds that someone is without a partner for the night. Of course! Sheila heartily agreed that the boss's solution was brilliant and promised to get the word out right away. But, she firmly declared, "I am not taking another man along! I am your date and yours alone and I expect you to act accordingly, my hunky Boss".

He beamed at this show of proprietary interest on her part. "O.K., O.K. my Love," he joshed. "It is just you and me. But you do realize that as CEO this hunk really does have to dance at least once with every lady there." Unenthusiastic smile.

Shiela was feeling the power and pushed her case, "Bull Pucky, Mr. Boss Man. You will dance every dance with ME, or I will invite a different hunk."

"I hear ya' Shiela, you're the Sadie in charge." He bumped shoulders with her as if in acquiescence but silently assumed he would be able to dance with anyone he chose to, come event night.

In the ensuing weeks, it was noted that there was considerably increased male/female socializing among staff members during coffee breaks or lunch hours. A man would be seen lunching with a woman that he had never been seen near before this Sadie thing started. Pairings were observed in the hallways and around the water coolers as two people who had been relative strangers before, quickly got acquainted with their prospective dates ahead of the big event.

Chelsea Seaman began sitting next to Will Marin at the lunch table almost every day. One or the other of them could sometimes be seen getting just a little handsy under the table.

Of course, there were a few couples that had long been the subject of office romance rumors, who were now enabled to more openly fraternize.

Once the initial 'dates' had become known around the office, it was as if all previous social barriers came tumbling down. A man and woman who didn't previously know much more than their co-worker's name and job title suddenly felt license to chit chat at each other's desk and to look each other up during lunch or coffee breaks. Not even marital status seemed to be an encumbrance anymore.

No one seemed to think anything scurrilous about all this. The new friendships seen around the office largely involved the dates for the upcoming dinner so, of course, they could pal around in the office, pretty much without raising eyebrows. Many seeds had been planted over those few weeks.

The big night approached relentlessly. Sheila says "Steve, I have an idea about the CAP." Yes, she was now calling him by his first name, but only when no other employees were within hearing. "Yes, sweetheart?" he queried, emphasizing the blatant term of endearment. He felt that it was his duty to squelch the first-name familiarity thing in the bud, and hoped his excessively personal response might scare her off. Which demonstrated that he didn't really know his Sheila very well at all.

She then suggested that Friday afternoon before the CAP, they should all formally knock off an hour early and gather in the cafeteria for wine and snacks, to let everyone know who will be dating who the next night (not that most of the pairings had not been public knowledge for weeks.) "You can make one of your boring little speeches to kick off the big event. With your arm wrapped tightly around my waist of course."

Carlson tried to stifle his grin, and said, "No princess. Not necessary. But do set up a similar confab for the attending employees here in the office quarters, an hour before our Saturday ballroom event is scheduled to begin." She looked puzzled and he continued, "You have previously advised the men not to pick up their date at her home. WAY too much concern about unpleasantness when married spouses see another man pick up their wife for a date night. So, the pre-CAP meeting is simply a way for the ladies to meet up with their date or dates and have a sociable drink before they drive over to the ballroom together."

At long last, the big Sadie Hawkins Day arrives. Shiela had to open up the office for the pre-CAP meet-up so she told her husband she had to leave about 4:30. She had been careful not to dress in an overly dressy or revealing way with no perfume in evidence. She had forgotten to tell him about the employee dating thing, simply giving him the news that the event was for employees only this year. He was pleased as all get out.

Arriving before the others, as planned, Shiela went into her own office and took off the long sleeve blouse she had on and her bra, stuffing those undesirables into her desk drawer. She replaced them with a very tight-fitting, pink peasant blouse sans bra. She pulled down her mid-calf skirt revealing a pink mini-skirt underneath. In two minutes she transformed the oh-so-prim Mrs. Warren into the ooh-la-la Sheila, consort to his majesty Sir Steven Carlson.

She was feeling proud of herself as the aforementioned Carlson arrived and greeted her with open arms and a gentle squeeze. "Best looking date I think I ever had." He said with a canary-eating grin on his face. Silently he thought to himself, she probably WAS the hottest looking woman he had ever had the privilege of "going out with".

As employees drifted in both of them got a kick out of watching the couples de jour spot each other and join together. Greetings varied, from demure handshakes to casual hugs, all the way to a few couples that kissed big time with open arms and wandering hands. Just showing off for the crowd it seemed.

Sheila welcomed them as they arrived and pointed out the table with open champagne bottles and a stack of plastic cups. Then she returned beside the boss, with her hand hooked possessively in the back of his belt. He glanced over his shoulder at her, but his smile did not hint at any discomfort with her display of intimacy.

"OK, everyone" Steve paused to allow the 60 or so attendees to quiet down. "If anyone's date is not here yet please raise your hand." No one did. "Great. Would have been embarrassing to get stood up by your own 'Office Date'. Polite tittering at a not terribly funny remark.

"We are so pleased to see this turnout and hope this will prove to be the best format for Willy Nellie's future anniversary parties. I have already noticed a nice atmosphere around the offices as employees have gotten to know each other better. I for one applaud that improvement." He turns to draw Sheila into the center space.

"I think you all know that Sheila Warren came up with this date night idea and we owe her a round of applause for what we can already say is a great success. I personally have the most to be happy about since I am the lucky S.O.B. who got to escort the lovely Mrs. Warren to the party." The applause was robust and genuine. His date seemed to blush as he put his arm over her shoulders and drew her to him into a showboat, full kiss on the lips.

"Well, I may have just skirted the limits of our company's no-fraternization policy so...the only prudent thing for management to do on this occasion is to fully suspend the no fraternization policy altogether for the rest of this Sadie Hawkins Day...well...perhaps it would be more prudent to say that it is suspended until 9:00 am Monday morning." Huge applause mixed with robust laughter. A couple of disapproving frowns darkened the back row.

At closing, Chelsea Seaman and her date Will Marin were among the first to prance out to the cars, like school kids. They stood intimately with her tightly in front of him throughout the brief talk and she now shamelessly led their way by grabbing ahold of his belt and pulling him forward alongside her. Even casual observers might speculate that they were going to become lovers this night. The more informed employees knew that train had left the station weeks ago.

Steve Carlson lingered back, waiting for Sheila to be able to close up the office building and then, prim and proper like, took her hand and led her to his Audi. They held hands during the short drive to the night club. He squeezed her hand, "This whole event was your idea, Sheila. I for one want to thank you for scheming it up and for allowing me to escort you tonight."

"I don't know about allowing you anything boss man. I pretty much got the impression that if I was to come with anyone else, I would be in big trouble. There's trouble with trouble, so I had no choice but to 'come' with you, mister."

"And I hope you do, missus. Often." That made her break out in an embarrassed smile. A smile that would be equaled numerous times during the evening as the two became so much more than coworkers at the office. A shared intimacy was filling their faces with loving looks.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
AnonymousAnonymous4 months ago

Is it too late to add a chapter or two to this story?

AnonymousAnonymous4 months ago

A BRIEF EXCERPT FROM THE STORY.

"Sheila herself was happy to take her chances with almost any random man instead of enduring the boredom of her doormat of a husband."

Oatmeal1969Oatmeal19698 months ago

Fantastical large-scale cheating scenario that is far from complete.

waltdeewaltdee12 months ago

Needs a better ending/closure.

AnonymousAnonymousover 1 year ago

FORGET the dates; count ALL the spelling & punctuation mistakes! The company doesn't care about quality?!

Show More
Share this Story

Similar Stories

Copycat A wife allows herself to be seduced against husband's wishes.in Loving Wives
My Wife Wants to Date Other Men My wife wants to date other men. I say no.in Loving Wives
Under Pressure Husband watches his wife get fucked by an old bastard.in NonConsent/Reluctance
Son's Gigantic Cock is Now MINE Ch. 01 50 yr old married MILF fucks 18 yr old German's HUGE cock.in Loving Wives
Shouldering the Burden A wife confesses her infidelity; the husband already knows.in Loving Wives
More Stories