What If?

A fantasy alternative to a humdrum life

Chapter 1 - Introduction

Eighteen year old Ted Watkins was a senior in high school. He ranked very close to the middle of his class academically. He was not that interested in sports. He blended into the middle of the crowd at school, not calling much attention to himself. His father worked in a large factory maintaining and repairing the industrial machinery associated with making automobiles. His mom worked behind the counter in a bakery.

Ted picked up his mechanical skill from his father, but was interested in cars and trucks. He started out at about age ten learning from his father how to change oil in the family car and expanded his knowledge from there. When his dad had purchased the family car he had also purchased a maintenance manual for the car. Ted read it from cover to cover. It wasn't too long and he was changing oil for his grandparents, aunts, uncles and neighbors. Then he branched out into doing tune-ups and replacing worn-out brakes. When some of his regular customers would buy a new car, he would buy a maintenance manual for that car and read the manual quite thoroughly. Ted had quite a business going on the side. If he did not have and could not afford the proper tools for a job, he would tell his customer and refer them to a reliable repair shop. But when Ted accepted a job, his customers knew it would be done right.

Ted had no interest in going on to college. He enjoyed math and science well enough and took the college prep pre-calculus course his senior year and had also taken biology, chemistry and physics. He was enrolled in a vocational curriculum. That meant that half of the school day was spent in a different building where the industrial ed courses were taught. Ted wanted to become a diesel mechanic, but the closest offering to that was automobile mechanics, so he took that. But because he had taught himself a lot of things over the years, they let him take some metals machining and electronics classes as well. The down-side to this was that he did not spend a lot of time with college-prep students, and he didn't spend a lot of time with auto mechanics students. He didn't spend much time with metals machining students or with electronics students. He was not on any athletic teams. So he had a lot of acquaintances, but not that many friends.

Carol Mather was a bright 18 year old. She had no plans for going to college. She attended the vocational school as a business student. Her math interests centered around accounting and bookkeeping. She learned a number of computer programs that were used in business and was fluent in them. She had taken some computer programming courses as well. Her vocational aim was to become an executive secretary for a CEO or COO of a large corporation.

Carol, too, did not have as many friends as you might expect her to have. She was one of those girls who, in grade school, carried a lot of "baby fat" around her waist. A lot of girls lost that when they hit puberty. Not Carol. So she was not cheerleader material. Nor could she keep up with the athletic girls when trying out for a team. Her clothes were not stylish. Many were bought at a second hand store and she fit better in women's sizes than she did in juniors. All her clothes looked like they were a size or two too big. Because she did not take college prep courses she did not hang out with the college prep crowd, and because she was such a superior student, most of the vocational education students were a little bit intimidated by her even though she tried to be nice to everyone.

She was a big girl: tall -- 5'10" with wide hips and broad shoulders. If she would wear heels, she would be taller than most of the guys in her class. No one knew if she even owned a pair of heels,

but that made little difference. She overheard, more than once, a guy saying that he'd rather not go on a date than go on a date with Carol.

If you asked someone who though he knew Ted, he might say that he thought Ted was afraid of girls. That wasn't quite it. Ted was afraid of himself. As soon as puberty hit, Ted had discovered masturbation. He masturbated several times a day. He felt guilty about it. He was also very worried

that if he would start going out with a girl, he would not be able to control himself and would maybe do in real life some of the things he imagined in his fantasies. So rather than put himself in that position, he simply didn't date, and when asked about it, smiled and said that he was a confirmed bachelor.

While Carol did not look the part, nor had she ever given anyone the impression that she was "boy crazy," she also had a very high sex drive. She would "diddle herself to sleep" (her term) more often than not. That, and the fantasies that went with it also filled her with guilt. Her parents had kept a tight reign on her, not wanting her to get in over her head during her dating years, but now wondered that maybe they had been to restrictive, because she had not gone on any dates at all.

Prom at their school was held shortly after Easter. In the lunch room the guys would talk about who they were going to ask. "Confirmed bachelor" Ted was told that he could not sit this one out. Ted even switched tables at lunch to try to avoid the question, but was unsuccessful. He then changed his excuse from being a "confirmed bachelor" to: he didn't know any girls to ask out. All the college prep girls had been asked, and there weren't any girls in auto mechanics, metals machining or electronics.

Just then, Carol walked by the lunch table. When she was out of earshot, one of the guys said, "Why don't you ask Carol? She's not that bad. You're tall enough that you will still be taller than her even if she wears heels. And after all, you're not asking her to marry you -- just go to prom. She'd be better than nothing."

Ted was not so sure. But that night as they were getting on a bus that would take them back from the vocational school to the high school, it just so happened that when Ted got on the bus the only seat left vacant was the one next to Carol. "Is this seat taken?" he asked.

Carol shook her head, "No."

Ted sat down next to her. The bus pulled out of the parking lot and drove several blocks towards the high school. Ted mumbled to her, "I don't suppose you'd go to the prom with me." They rode another block. He looked at her as though maybe he was expecting her to answer.

She looked at him. "Are you asking me?"

They rode another block. "Yeah. I'm sorry, I'm not so good at this. First time. Would you go to the prom with me?"

"I'm not so good at this either. Never been asked before," was Carol's initial response. She did not know Ted very well, but she had not heard anything negative. It was getting kind of late in the season and she had been worried that maybe she would not be asked at all -- or asked by somebody she just could not stand.

Carol found herself feeling scared. But it would be humiliating not to be asked to the prom at all. Ted would be better than nothing. There had been an awkward silence while Carol was mulling this over. Finally she said, "I would be happy to go to the prom with you." The bus pulled into the parking lot of the high school.

Chapter 2 - Prom

Time for prom came. Both Ted and Carol had done their homework. Ted had a nice income from his auto repair work, and so bought Carol a very nice corsage. He took her to a fine restaurant, but before he took her there he went there once by himself so that he would know what it was like. He had read that the best way to start a conversation was to ask the girl about herself and her interests, so he was primed with some questions that he could ask her, without prying into her private life -- questions about her business courses and plans for after graduation. So dinner at the restaurant went well.

Both of them had learned to dance in gym classes. They didn't learn enough to really be good. So whenever they danced they both concentrated on their feet more than anything else. Neither of them wanted to dance the fast numbers. Ted felt that he would just look awkward and Carol felt she would look awkward and fat. They sat the fast numbers out, sipping punch and talking more about their schooling. They eventually also shared their likes and dislikes about the music that was being played. They shared admiration for the good dancers and made fun of the ones who should have sat the dance out. They both mentioned that at some future time they might like to take dance lessons and become good like the people they were admiring.

At one point they were dancing to a slow number -- thinking about their feet, and between numbers, the leader of the band said something that struck Carol as being extremely funny and she broke out into an uninhibited laugh. She was still very close to Ted -- he still had one arm around her from the preceding dance -- and he couldn't help but notice, and say out loud, "You're very pretty when you laugh."

He was shocked that he had said it out loud. He half apologized: "I hope I wasn't being inappropriate."

Carol replied, "It's never inappropriate to give a girl a compliment."

But Ted did not know what to say next, and neither did Carol and soon the band started playing again and they went back to carefully thinking about their feet.

When Ted dropped Carol off at her front door, She said, "Thank you, Ted, I had a very nice time. Thank you for taking me to the prom. I'll never forget it."

Ted replied, "I was really scared about how the evening would go, but you've been very nice to me. So thank you." He had held her hand walking her up to her door. He held it for just a moment longer, then, not knowing what else to do dropped her hand and walked back to his car as she opened the front door to her house and walked in.

The first thing she did was take off her shoes. She had worn heels and her feet were killing her. She, too, had been scared about the evening, but Ted had been nice to her. She thought that this prom thing and dating was way overrated, and wasn't looking forward to being asked out again. But the highlight of her evening was when Ted had told her, "You are very pretty when you laugh." As far as she could remember it was the first time anyone had told her she was pretty since she was a little girl and her mom was putting bows in her hair. The way Ted had blurted it out -- and then almost apologized for it -- proved that the compliment was genuine. Those words would stick with her for a very long time.

Ted also recapped the evening in his mind. It wasn't the total disaster it could have been. It certainly was not a sexually stimulating experience. It left him feeling that he was definitely socially awkward and certainly not ready to sweep any girl off her feet. Carol was nice to him. He hoped that there were some parts to the evening that she would have enjoyed. She deserved that. Now he would go back to being the confirmed bachelor.

Chapter 3 - Life Goes On

After prom Carol was caught up in a whirlwind of experiences that had huge impacts on her life. Even before prom, before her senior year, Carol had started to do the family wash. Her mother, a relatively young woman, found it more and more difficult to go up and down the stairs that led to the basement where the washer and dryer were located. She would find herself short of breath after coming up the stairs. So Saturday mornings found Carol gathering up the wash and going down into the basement to sort the laundry and then load the washer, then the dryer, repeating the process until the week's worth of laundry was done. She would fold the clean laundry and take her parents' laundry into their bedroom on the first floor and her own clothing up to her room on the second floor.

Carol wasn't the only one to go into the basement on Saturday morning. After the family ate breakfast together her dad would go downstairs to his shop in the back of the basement. It was enclosed, so that if he used a power saw or sander that the sawdust would not fill the entire basement. He would stay in his shop until about 9:00 in the morning and then leave. In the winter he would go bowling with three friends. In late spring, summer and early fall, he would go golfing with the same three men. He'd go down to his shop right after breakfast. Carol would be down sometime later, having taken time to gather up the dirty clothes and strip the beds.

One Saturday morning, as Carol came down with the wash, she noticed that her dad's shop door was somewhat open -- not wide open, but open enough for her to see into the shop. What she saw almost made her drop the wash basket and scream. But she did not. Because what she saw not only caused shock on her part but also fascination. For what she saw was her father standing at a 90 degree angle from the door. He was naked. He was looking at what appeared to be a magazine that was placed on his bench saw, and he was masturbating. He was a handsome man, and in good shape from his work in construction. Carol moved as close as she could without giving herself away. She could hear him muttering under his breath, "That's it baby, take my big fuck stick up that pretty little fuck hole. I wanna fuck you so hard, baby. Oh you feel so good on my cock. I love fucking you and watching your huge tits bounce. Ohhhh, you're so fucking sexy, baby, you're gonna make me cum." On and on he went like that for about five minutes as he stroked his cock, and then he shot his wad. "That's it baby. You make me feel so good. Oh, fuck!" he murmured until all his seed was shot. He then proceeded to wipe up the floor where his cum had landed, wipe off his cock and get dressed.

Carol returned to the laundry area all hot and flustered and hurriedly started sorting the wash and filling the washer with water and soap. In a little while her father came through the laundry area and went up the stairs. "Off to play golf," he said.

As soon as the car pulled out of the driveway, Carol went into her father's shop. She looked in the cupboards and found a stack of magazines. Evidently her father liked blondes and big tits, because the preponderance of pictures were of girls like that. He also evidently liked shaved pussies. Many of the pictures were of girls being fucked in many different positions.

Carol got out a magazine and put it on the table saw. She took off her clothes. She fingered her pussy and her clit with one hand and pulled on her nipples with the other, all the time saying, in a quiet voice, "Fuck me, baby, Fuck me with that great big cock."

Carol's father continued this for about five more weeks, keeping the door ajar as he masturbated on a Saturday morning. Then, the following Saturday morning the door was closed while her dad was in there. Did her dad leave the door open on purpose? Carol never did find out. But when her dad left on Saturday mornings, Carol continued to go into his shop, remove her clothes, get out a magazine and bring herself to climax, until she bought porn of her own which she used in the privacy of her own room. Even then, when she wanted to feel especially naughty, she would invade her dad's shop and use his porn on a Saturday morning.

Chapter 4 - The Job Offer

It was during this same time frame -- the end of her senior year -- that Carol was called into the office of the head of the Business Department at the Vocational/Technical School. When she arrived at his door he invited her to come in and sit down.

"I have a wonderful opportunity for you," he began. "I just got a call from Francis Wainwright. He is the owner and President of a large company that deals nationwide with commercial real estate and also in purchasing failing businesses and combining them in such a way that the combined business becomes profitable. He has been very successful. He started this business about twenty-five years ago and has had the same administrative assistant from the beginning.

"That administrative assistant wants to retire at the end of the year. In talking with the head of his HR department, there is no one currently in their secretarial pool that they feel they can bring up and train for the position. A few are qualified, but will be wanting to retire in the next three to five years themselves. Others are good secretaries, but could not handle the responsibilities that being the administrative assistant to Mr. Wainwright would require.

"So he called me up. His daughter went through our program a few years ago. He was hoping that we might have an outstanding student that they could take on and train under the current administrative assistant over the next six months who would then be ready to fill the job come January of next year. I immediately thought of you. You've been an outstanding student in every way and I believe the job would be right for you and you would be right for the job.

"When I told Mr. Wainwright that I did have an outstanding student who would probably be the perfect fit for the position he just described, he made arrangements to interview you himself. So next Thursday he is going to send over a car and driver to pick you up from school here and take you to his headquarters so that he and his current administrative assistant can interview you to see if you are right for the job. I'm sure you will be."

"This is amazing," said Carol. "Do I have to get a note signed by my parents to get out of school or do anything else to be prepared?"

"You will not have to have a note, or bring anything with you," said Mr. Julius, the head of the department. "However, if I may be so bold, I'd like to suggest to you that you wear something more appropriate than what you usually wear to school. You are applying for a job as assistant to the President of the company. The office you will be working in, should you get the job, will be on the fifteenth floor, the Executive Suite. Your dress will want to reflect the prosperity of the company and the authority of the president of that company. So if you can possibly afford it, I would suggest you go to a major department store that has a department that serves professional women, and buy an appropriate outfit for the interview. If you get the job, you will be able to wear it to work. And even if you don't get the job, it will be a great outfit to wear to any other interviews you go to looking for a job as an administrative assistant."

"That sounds like a great idea, Mr. Julius," she said, "and I have some money saved up from babysitting and from a Christmas gift that I can use to make the purchase."

"If you're willing to do that, I know just the place to go and the person to contact. Go to the anchor store at the mall to the department that sells clothing for business and professional women, and ask for Cheri -- that's spelled with a 'C'. She used to attend here as a marketing major. She will be

able to help you find exactly what you're looking for. In fact -- let me give her a call right now. I'll tell her what's up and then you can arrange a time to meet her."

Mr. Julius got Cheri on the phone -- he had often sent girls over to her to get clothing appropriate for an interview -- and after a little small talk explained Carol's circumstances to her. Cheri asked him to put Carol on the line. Because Carol's family had only one car, Carol had to guess at her

parents' schedule as to when she would be able to get the family car and drive to the mall. Friday evening was the time that best fit both their schedules. She gave the phone back to Mr. Julius who thanked Cheri for helping another girl out, and then the phone call was complete.

"Oh Mr. Julius, I'm so excited! Thank you so much. What a great opportunity! My parents will be so pleased!" On and on she gushed.