Stay Lady Stay

Story Info
Lonely man finds the love he's been looking for all his life.
20.1k words
4.58
17.6k
16
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

Stay Lady, Stay v2.01

1 This story is entirely fictional and takes place in a fictional version of Boston.

2 There is no under-age sex represented in any way. However, this is Literotica and even in a Romance story some characters do express their love in a very physical way.

3 I despise and do NOT condone racist language in real life. On the other hand, I know despicable people do use racist and other demeaning words and I have had one of the characters in the story talk in such a way as to reveal his true character. I apologize for any offense given.

Introduction

They are all around us, but hardly ever noticed! They are the wallflowers, the small people, for most they are mere shadows, the anonymous who without recognition are still essential to the functioning of society. They deliver mail, they keep the utilities running and fix our cars, and we really know nothing about them. They were not in the popular group in high school, sometimes they were bullied, almost always ignored, and yet they are living breathing human beings with lives to lead, but often, despite their human limitations. The little things of life so often wind up having a profound effect upon our human lives. The position in which we are born into the family, how we were treated at school, especially in our first few years, whether we were in the popular in-groups or did we become the target of bullies? Did we have supportive parents and teachers or those who told us we are worthless? So many little things can simply build or tear down our self-confidence. These people, in some ways social outcasts, people with low self-esteem, often lead a lonely existence. But what if....

Stay Lady, Stay

Jude was a nice little boy, but had neither outstanding attractiveness or strong intellectual gifts. An only child, He would never be a teacher's pet, or get special recognition. Many teachers would not even be aware he was a deep thinker who was very sensitive to how others treated him.

In Jude's first few years of school the teachers made a big deal out of Valentine's Day. Each child was supposed to share a valentine with each other student. Of course, some could not afford to give one to everyone else, but somehow Jude always seemed to receive the fewest in the class. He was only a kid but still it made him feel unappreciated lonely and unloved, almost like being a social outcast.

By middle school years February 14th was his least favorite school day of the year.

He arrived in high school with a far lower than average level of self-confidence, he actually had developed Valentine's Day phobia. Shy and a bit of a loner, it was hard for him to get dates, and he never had a date for the school's Valentine's Day Dances despite wanting to ask many girls. Jude simply could never work up the nerve. He was human, he had the same desires, the same yearnings as so many others, but it just seemed that the normal things of life were always denied to him.

Jude was solitary, yes, but not unaware. A deep thinker that watched and analyzed, he noticed that Valentine's Day seemed more like a girl's thing. Girls seemed to love the attention of getting cards and silly little gifts.

When he was finally able to get a few dates, he still didn't like Valentine's Day. Even as he began to have more intimate dates, he hated the fact that he felt pressure to do the 'plastic fantastic' Madison Avenue right thing for Valentine's Day, or live with the fear he would be rejected. When he gave in and bought a gift his gifts always seemed to be the wrong ones. He tried so hard to make them thoughtful and personal, but of course he never had the money to be able to give expensive jewelry or large bouquets of roses to the women whom he courted.

Many adults have their little phobias and foibles but they do not keep the person from a high level of performance at work. So it was for Jude, he was smart and driven at work. The only fly in the ointment was that he struggled with negative, demanding bosses.

At first, Jude was doing extremely well at work, but his wonderful boss took a far better job in another state and the new boss, Avery, was a negative bully who saw himself as a little god to be worshiped by those under him. Avery seemed to think encouragement was wasted and a stick worked better than a carrot, that fear was a great motivator and kindness was a waste of effort. It really took the bloom off the job for Jude. Jude further noticed that Avery was a terrible misogynist who looked down on all females as inferior beings, treating them as toys to be used and then discarded. He seemed to believe a woman's only real place of value was in the home cleaning and cooking in the kitchen...and of course servicing him in bed. Secretaries and nurses were an exception to that rule...as long as they were 'dishy'. Powerful men, as he viewed himself to be, needed to make an impression on the world. Clients should be impressed by their big offices, the sexiness of the receptionist, their secretaries' great racks or asses. It was no surprise he never had a male secretary!

Like most misogynists Avery did not think he was being sexist. To him it was a simple fact of life, men are superior and alpha males were the only men that counted. Woman's primary purpose was to serve a man's sexual needs. Men didn't have great racks or asses so women needed to be 'eye candy' receptionists and secretaries. The same with nurses. A nurse might have to professionally insert a catheter. That would mean touching Avery's junk. Avery couldn't stand the thought of a man touching his cock in any capacity. So, Avery needed women, hot women, all around him.

It is funny how one thing can be a great irritant and at the same bring some welcome relief. Avery liked to humiliate his employees. The women had to put up with what was in effect sexual harassment. As to the men under him, instead of talking directly to them, for he was far too important, he had his secretaries go give them his orders, in effect saying they were only worth a secretary's time.

The secretary for the old boss had been with him for 15 years. She lasted less than 2 months with Avery. Every new secretary had to be attractive, a real looker and it seemed that Avery demanded not modest office attire, but women with sexy clothes and make-up that had to be like perfect Barbie Dolls.

A pattern soon developed. Married women lasted a few months, singles seemed to last a bit longer. Ultimately no secretaries could stand Avery's constant sexual harassment and belittling forever. Many quit in frustration or were fired with resultant settlements. The nicest thing a person could say about Avery was that he was a huge egotistical asshole. Jude didn't blame the women at all. Jude barely dealt with Avery. He couldn't imagine dealing with the asshole all day long!

When delivering Avery's messages some of the secretaries seemed to enjoy putting the male employees down, acting superior because of their 'beauty'. However, a few were gentle, smiled nicely and tried to soften the message. It was amazing what a cheery smile and a word of encouragement from a very attractive woman would bring out in the men.

The one that made Jude feel the best was Sarah. She was cute, vivacious, and a hard worker. Not surprisingly, because she was a mother with young children, she had left after working under Avery for six months. Her last day, had been the Friday before the long 4th of July weekend. Jude had developed a little crush on her and was very sad to see her and her beautiful smile leave.

On his return from the long weekend, Jude was working at his desk. He got a phone call with a question about something from weeks ago. He opened the large bottom drawer of his desk where he kept older files until he later moved them to the file cabinet, to get the answer.

He was shocked when, near the back of the drawer, lying flat across the files was a pink envelope with red hearts.

He knew that he accessed the drawer on a daily basis and the card was not there the last day of work before the holiday. He picked it up and laid it on his desktop, found the file he needed, and returned the call providing the information requested.

The task completed he looked again at the envelope. Why would someone give him a Valentine's Day card when he hated Valentine's Day so much? Was it a cruel prank? Maybe he should just throw it in the bin unopened and save himself from the emotional pain of what seemed to be a cruel prank.

Finally, curiosity won out over fear. He studied his name written in a beautiful feminine style. Who would have sent it? And why? Carefully he opened the envelope and withdrew the card. It was obviously very expensive, something one would give to a lover, but he had no lover. Finally, with trembling fingers, he opened the card and a slip of paper fell out and fluttered to the floor. The card was signed: "I will miss you! Love, Sarah!"

Then he remembered the paper falling to the floor. He reached down, picked it up, and read: "I bought this card for you last February, but then was afraid that you would not understand and might become angry with me. When I cleaned out my desk before leaving, I found it and just really wanted you to have it, since I would not be around to see if you got angry or were hurt. XXX"

He was absolutely flabbergasted. Jude had heard she was a single parent and had thought about trying to ask her out, but his shyness had caused him to procrastinate too long, and then she was gone. Further, he was full of doubts. He was forty-three and not terribly attractive. Sarah was so wonderful she deserved someone stronger, smarter, kinder, someone, who made a better living. Still, he would often think of her and imagine what it could have been like with her if they had become a couple. It would have been nice to have a caring girlfriend instead of a Tinder 'romantic hook-up.

A solitary man, Jude just wanted to do his job and be left alone. He had little to say and mostly kept to himself. He usually could not understand how other people thought and after being hurt many times he had a hard time trusting any other person. Jude was puzzled and eventually frightened by all social conventions such as inane conversation, parties, religious forums, and politics. When it was necessary to join a discussion, such as for work, he would say as little as possible until he could escape to go home.

Jude would be the first to admit he didn't have much of a social life in Boston. Jude had his work and his Tuesday night Candlepin Bowling Club at Bowlerama. That was about it. When moving to Boston from Wisconsin, Jude had discovered he was good at candlepin bowling. It was a regional form of bowling unique to the North-Eastern part of North America. The pins are smaller and like shaped more like Candle, and a player got to roll a third ball. Jude bowled on Tuesday nights with Seth, Donavan, and Ben but after eight years burgers, beers and bowling had become rote.

Now that his friends had families of their own, bowling was often canceled due to parent-teacher conferences or kids' sports games. Jude's friends' happiness left him feeling even more lonely. He longed for a family of his own. He longed to attend a parent-teacher conference about his children.

Meanwhile, in another part of Boston where tenements were common, the still relatively young Sarah was living with her boys.

About six months later...

It was a blustery mid-winter Monday early in January. Jude sighed as he got off Boston's MTA, and begin to walk toward his office. As he did every day, he walked past a Walgreens store. He was surprised to see one window was decked out in Valentine's decorations. He shrugged. 'Christmas creep' always bothered him when so much Christmas stuff went up right after Halloween. So, he thought in a way that Valentine's Day Creep should not have surprised him. He just still hated Valentine's Day. It seemed that since high school every lover Jude ever had expected some plastic chintzy crap on Valentine's Day. He thought it was all probably thrown out on February 15th, but if you didn't buy the crap, according to Madison Avenue, you were an indifferent lover.

Jude had tucked away the memories of most of his life before Boston; they no longer seemed relevant. Today's actions and choices were what was relevant. It was best not to dwell on the past. The present was pertinent, the questions had immediacy. What to do? Where to go? Whom to spend the day with? Jude wondered, though, why he only had questions and no happy answers seemed to lay before him.

The day was cold and gray. A freezing and foul-smelling wind swept up off of Boston Harbor and into the city. A Nor'easter was on its way. The news had said to expect a bad one. Jude was in low spirits and his soul ached in loneliness. Suddenly a big gust of wind blew a visibly pregnant woman into Jude. He was knocked off his feet, but miraculously the woman was still standing. She was holding out a Dunkin Donuts cup and was apparently begging.

"Sarah?" questioned Jude astonishingly as he looked up at her remembering that Sarah had been his boss Avery's secretary just two secretaries ago.

Jude had liked seeing Sarah in the mornings. She always snuck coffee and Dunkin Donuts down to the "mid-level" office workers from Avery's top-floor office area. Jude remembered his little crush on her and felt that his feelings had been reciprocated, even though they'd never been on a "romantic couple's date". He still remembered her Valentine from the previous year. Though he realized it had just been an office friendship, still, small actions like sharing donuts can have a far-reaching impact on the feelings of others. With Avery they had results even Sarah couldn't have expected or predicted as to her it was such a small thing to share.

"Oh! Hi Jude," said Sarah, as she clutched her tattered coat tighter around her bulging belly. She sounded so weary.

"What in the world are you doing out here in the cold? This freezing weather is bad for you, let alone your baby! Come with me to the office where you can put your feet up. When my little sister was pregnant that's all she wanted to do." Jude was firm in his demands, clutching her bare hand, and practically dragged her toward the office. Sarah, after briefly hesitating, followed him.

When they arrived at the warm office, they entered and he lead her to the employee break room near his station. ."

"Please come in and sit down," said Jude as he pulled out his worn office chair.

"Coffee?" Jude questioned, but noticed her frowning. "Well, obviously not coffee but something hot that can warm your bones?"

Sarah nodded. Jude brought her a cup of chamomile tea and a frosted donut. He put one in each of her freezing hands.

"Ank you." said Sarah. Her mouth was soon full of dounut. "I didn't eat breakfast this morning."

Jude sadly looked at the pregnant but emaciated Sarah. 'Why wasn't she eating?' he wondered. Remembering the type of person she had been, brought back more memories. Jude knew Sarah's kids always came first. She existed for them and only for them. Sarah had either one or two kids at home, he couldn't remember. He didn't ask Sarah any questions as she sat next to him still shivering. He certainly didn't ask who the father of her baby was but natural curiosity caused him to wonder.

There were a million questions, but ultimately they were not essential things, such as her kids' names, her birthday, or where she had gone to high school. Jude knew he could find these out in time. The point was that he felt that he truly loved Sarah and wanted to help her.

He looked at his friend who suddenly started retching up the sugar doughnuts into a trash can. This Valentine's Day season, Sarah was as far from looking "sexy" as a woman could be. Still, because Jude truly felt in love with Sarah, it was not sexiness he wanted to see, but her beautiful warm smile. Even more, he wanted Sarah in his life again. Selfishly he wanted her to be his.

Then reality hit him. His dream was wildly impractical. It was crazy! Jude knew he would advise all his friends not to think what he was thinking. Yet, still, Jude was sure he loved just Sarah. He didn't care about the practicality. Somehow, he was drawn to Sarah as if by some primal and unknown force of nature.

A strange thought came to him: What causes swans to come together and mate for life? This was Sarah, she was his swan! The fact that she was pregnant and had two kids didn't deter Jude. Somehow all those relatively unimportant things would be figured out. The main thing was, he just wanted to show Sarah how much he loved her. He wanted to love her like the swans loved each other. For him, it was really as simple as that.

Jude often had had a dream of him and Sarah living somewhere in Boston's suburbs. In his vision, there was a large yard with a treehouse and a white picket fence flanked by Boston Ivy and flowers that Sarah planted. He visualized her boys are playing catch in the backyard; he saw Sarah nursing a new baby, the baby she had with him.

Now, instead, here she was at his office and she was freezing! Jude leaned closer and gently swept a stray strand of hair from her eyes and tucked it behind her ear. He gently kissed Sarah's forehead. Her skin was still freezing! This was just not supposed to be in so many ways.

He blurted out, "Fuck, all of this. All of this office work doesn't matter, ultimately lots of things don't matter. It's all inane bullshit. But you matter to me Sarah, I'm taking a sick day and we're going home. We're going to get you and that baby better... and. if it's alright with you, your kids can rough it on my Lazy Boy and sofa for a while. We will figure this all out.

"Now come home with me," insisted Jude, as he held out his hand to help Sarah up.

Sarah just nodded. She was tired and her feet hurt so much...well she was pregnant, so really everything hurt. She also felt guilty as she didn't want to impose on Jude or take advantage of his friendship. But it was too cold outside to continue begging for money and she was simply exhausted. Sarah was ashamed to be out begging, but the rent had to be paid one way or the other. No one would hire a woman who was seven-months pregnant.

Begging was a last resort. She had visited all the social help programs, and the social workers all gave her the same message or variations of the same answer. Denied! Not applicable No benefits available! Sarah felt stuck between a rock and a hard place. She had her baby to think of...and her two boys. Somehow the rent had to be paid and her boys needed to be fed.

Feeling faint, Sarah sank into Jude's protective embrace as he reached over her big belly to button her coat and straighten her ponytail. Sarah had always sensed, that, though often silent, Jude was one of those rare men who wouldn't press his advantage or take liberties with her body. She believed Jude was a true gentleman. He had always treated her kindly and always kept his word. She sensed a man of true honor, even though in many ways he was almost a stranger. In desperation, she knew she had to trust someone.

Before she fully realized it she found herself in an Uber and then in his small Cambridge apartment. To her surprise, she was sitting in a lounge chair and he was hanging up her coat in the closet.

"Uhmm...welcome to my apartment, Sarah. I know it's a bit messy but I wasn't expecting guests. How about a cup of peppermint tea? I have a box of excellent peppermint tea from when my little sister stayed here, you can have some of that...I guess." Jude shrugged showing he was nervous. He'd never had had a woman he'd cherished in his apartment before and he ached to have things just right for her. Still, prepared for company or not, Sarah was here. Oh well, for better or worse, it was make-or-break time.