A Summer on the Road Pt. 01

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The boss's daughter wants a different summer experience.
4.3k words
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Part 1 of the 9 part series

Updated 06/08/2023
Created 01/10/2017
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Dear readers, this is the first chapter of a multi part story. I hope you enjoy this and come back for the rest of the story.

*****

Jane looked down at her legs, shifting them from side to side, assessing her tan. They were still very pale, not unusual for early May, but she liked what she saw. Her long legs, highlighted by the black bikini bottom, were one of the features she liked about her 5ft 7 in frame.

Sitting beside her on another of the pool loungers was Tara, her BFF all through high school. They had been catching up on their lives which had diverged when they had chosen different universities.

Jane was indulging in a Margarita while Tara sipped a diet coke, alcohol free as she was driving, having lost the coin toss. At least they could purchase alcohol at 19 even if the law stipulated zero percent blood alcohol when driving under 21. Jane could never understand the drinking rules her cousins from Connecticut lived under. Their government had no problem sending 19 yr old soldiers to very dangerous parts of the world but still thought a Coors light was too risky at their tender age.

She looked over at Tara and sighed deeply.

"What?" Tara asked, frowning at the sigh.

"Freedom's over. I start work tomorrow. Back to the drudgery."

"Well at least you don't have to look for a summer job like most of us."

"Sometimes I wonder. Working for the family company isn't all its cracked up to be," she mused.

Jane was the only daughter of Henry Robertson, the CEO and President of Roberson Industries, a privately held corporation. The main business was transport with warehousing and logistics as secondary businesses. A smaller but growing air freight business and a packaging company rounded out Roberson Industries. Henry had started as a truck driver and then an owner of his own rig and then an owner of several rigs which he grew steadily until the company was one of the major players in the transport industry in the region.

Henry had two older sons. Neither had shown the slightest interest in working for the family firm even though Henry had tried to induce them in every way. Henry junior was deeply interested in music and guitars in particular. He and two friends had formed a guitar manufacturing operation specializing in custom high end electric guitars. David was a biology major heading for medical school. His summers were spent working with his professors on research projects.

Leaving the country club and its pool the two girls headed home with Tara driving.

Jane sighed deeply. Tara looked over at her and said, "What? Still pissed about having to work?"

"You know, its not that I mind working, its just so boring. l don't think I do anything real. The people in the office never forget I'm the owner's daughter so they just give me some papers to push around. I never see the point of what I'm doing." Jane ran a hand through her thick chestnut coloured hair, a frown settled over her pretty features.

"Yeah I can see that would be frustrating. Can't you ask your dad for something more interesting?"

"He doesn't really see my point. Maybe I'll try again," Jane replied, staring out the window.

Tara pulled into the left lane to pass a semi. Jane snapped up in her seat. "Hey that's one of ours. Look at the new cab. Dad is really proud of his new Volvo trucks."

"Hmm ... just looks like a truck to me - lots of chrome and colours though. Must be fun to drive one."

Jane waved to the driver as they passed. She continued to watch the semi in the rear view mirror. Suddenly she snapped up in her seat and looked at Tara. "You know what? Driving one would be fun. Definitely more fun than shuffling papers in the office."

Tara nodded her head. She looked over at her friend who appeared deep in thought. "So are you thinking you might go for it? Really though, I can't get the image of you behind the wheel of one of those monsters.

"Why not? I wouldn't be the first woman driver in the company. Dad says the modern rigs all have power everything - not a lot of strength required."

"What about all those guys? Are you sure you want to hang out with a bunch of truckers?"

"I've met some of them at the company picnic. They're all okay. Dad says he only hires the best drivers."

Jane was silent for awhile, slowly turning the thought over in her mind. The more she did the more she liked the idea of spending the summer behind the wheel and on the road. She only saw one hurdle and that was her dad. Her mom would come around okay but Henry Robertson was a very stubborn man and Jane was sure he wouldn't react well to her request. It would take some work but the more she thought about it the more she wanted to become a transport truck driver for the summer. She was determined to get her dad on side. Jane knew that in the end he couldn't say no to his little girl when she wanted something.

****

Days later.

Henry Robertson sat down in front of George Simmonds, the director of the trucking division. He looked at George, leaned back in the chair and let out a big sigh.

"Hmm, that bad is it?" George mused, somewhat concerned about why the big boss was in his office. The body language rolling of Henry was unsettling.

"Naw, nothing wrong on your end. My issue really," Henry responded.

"Okay, anything I can do to help."

"Yep, you can. Its about my daughter Jane, she wants to become a driver. I can't talk her out of it."

"Whoa, you mean that little girl I last saw at the company picnic. Don't tell me she's grown up."

"Almost 20. She's worked over in Head Office for a couple summers but somehow got the idea she wants to go on the road. Long haul no less, " Henry said.

"So are you going to let her do it?"

Henry just nodded his head. "The little princess always gets her way in the end. I shouldn't have bothered trying to talk her out of it."

"So, how can I help."

" I need the best driver you've got to train her up. And more importantly, I need someone I can trust with my little girl, if you know what I mean. The driver has to be patient and ready to take some crap. She can be a bit of a brat at times. She knows she's the little princess of our family and her mom and I haven't helped a lot. We've always let her get away with stuff. But in the end she's our one and only princess and nothing is going to happen to her that I can help. So, I need your best guy to train her and then take her on the road," Henry laid out his request.

George got up from his chair and paced behind his desk nodding his head and muttering to himself as Henry watched him. After several minutes of thinking, George turned to Henry with a frown. "I think I have the guy but I just don't know if it'll work for him. Do you remember Paul Cain? He's the driver who worked for us between semesters of university until his wife died very tragically in a car crash. He was left with two small girls. To make it work he dropped out of university and came to us full time. He's my best guy and has done a lot of instruction and training of new drivers. He's very safe and I believe is very trustworthy in all respects."

"Sounds like the guy I want. And now that you mention it I do remember him and what happened to his wife. His two little girs were at the company picnic last year. They're adorable. So whats the issue with Cain?"

"Well right now he's almost exclusively working the load prep and dispatch end. He makes the driver's schedule up and checks out new guys. Keep in mind this is one very smart and competent guy. After his wife died we tried to help him out by keeping him around the yard. He needs to be home for his kids. At the same time Joe retired and Paul moved into the dispatch office full time with some driver training to round out his work. He's made changes here and there, all very good for us and he's becoming indispensable."

George continued,"Bottom line - it would be hard to ask him to go out onto the road again. His mom helps him out with the kids but it would be tough on us somewhat but mostly on his family."

Henry leaned back in his chair and stared at the ceiling. "But he's the best, correct?"

"Yep."

"And would he keep his hands off my little girl?"

George was startled at the directness of the question. "I think so. The guy's got integrity and smarts. He needs the job badly for his family."

George frowned and then continued, "As for the other guys, well ... I'm going to be delicate here but lets face it, your daughter is ... well, lets just say she's exceptionally attractive. If she was mine I wouldn't want to see her loose out there in the yard."

"Yeah, I know. My baby girl is a hot little number. What about Joe - would he come back on a short term contract for the summer?"

"Yeah, thats what I was thinking too. He stops by now and then. I think his wife is getting to him - she wants him working in the garden."

"Okay, good. I'm thinking that I might be able to get Vera, my wife, to help out with the kids. I know she saw them at the picnic and the mother juices were flowing. She's seriuosly in need of grand kids and she thought the Cain kids were super cute."

George looked optimistic, "That would certainly help."

Henry jumped up, "Lets go for it. If he's the best I want him for Jane. Who knows, maybe after a day or so she won't like it and give it up. You never know.'

"Do you want me to talk to him or you?"

"I'll do it. I'll lean on him a if it comes to that."

****

Early the next week Paul Cain was moving between trailers sealing up loads. Looking across the yard he saw his boss, George coming towards him.

"Morning Paul," George greeted Paul. " How are we looking?

"Morning loads are ready. Most are on the road. The rest are ready to go," Paul said.

"Good .. good. Could you spare a few minutes? Henry would like to have a chat with you. He's up in my office now."

"Umm ... Henry ... would that be Mr. Robertson by any chance?" Paul said, his voice betraying some anxiety. What would the big boss have to chat about with him? Whatever it was he didn't think this was a social call and that couldn't be a good thing.

"Yep but don't look so worried. He's not out after your ass. I think he has an offer he would like to run by you."

"Offer?? Okay. I'm mostly done out here so I'll head upstairs."

****

Henry Roberson jumped up as Paul walked into the office sticking out his hand to the young man. Paul had married young and he and Gillian, his young wife, had two young children very quickly after their marriage. Paul was only twenty seven and fully on his own with three and five year old daughters.

He had grown up fast.

"Paul, I'm Henry Robertson. We met at the last company picnic. Your kids were adorable. How are they now?" Henry asked as he launched into his sales job.

"Very good sir all things considered. Thanks for asking," Paul replied. somewhat warily, still apprehensive as to where this was going.

"Yeah, I get it. It must be tough on them not having their mother."

"Yes," Paul replied, a distant look on his face. "We're getting a lot of help from friends and family."

"Look, speaking of family, let me get to the point. I'm sure you're busy. My daughter Jane wants to learn how to drive a transport and go on the road and I need someone to partner up with her."

Paul visibly startled. Where was this going he thought.

After a brief hesitation he responded, "Okay, so you need a partner for her. I know the drivers well. I could help you find a good one." Paul was somewhat relieved at where this seemed to be going. It wasn't about his job which was his first concern.

"Paul, I want you to take this on. George tells me you're the best man for the job," Henry said while looking hard at the young man.

Paul was taken aback. He had just been asked to drive with his big bosses daughter. Besides the fact of who she was he knew it would seriously complicate his life. How do you tell the sole owner of the entire corporation that you can't do it?

"Whoa Sir! Thankyou for the confidence, but there are lots of guys who could do a good job."

"Look, this is my little girl we're talking about. I don't want just anyone. You're considered the best driver and instructor in the firm and if you want the other reason thats big for me I'm told you're a guy who doesn't let his dick do his thinking for him. I would be trusting you to keep it in your pants. Got it?"

"Sir, I assure you I've no time for a relationship of any sort. As you know I'm on my own with two small kids. Thats my life now and my focus is taking care of them. It would be tough to go on the road and take care of them at the same time. Also, with Joe retired my role is on the dispatch side of the business."

"Paul, we've got you covered. Joe has agreed to come back on contract for the summer while you're out with Jane. As for the kids, we'll cover that as well. My wife Vera has agreed to help out We can hire a nanny if necessary. Anyway, its just for the summer or until my little princess has had enough."

"Wow! Your wife! I think i'm getting the idea no isn't an option."

"Yeah, I really want you to do this. I think its a dumb idea but Jane won't give it up. If its really going to happen I want the best guy to take her under his wing, so to speak. And George says you're that guy."

Henry continued, "The first couple of weeks will be teaching her how to drive a rig and getting her licenced. That'll be day shift work so shouldn't impact picking kids up at day care or whatever. So say yes and let's take this one step at a time."

"Okay lets start with the training and see where it goes," Paul said, sensing he really wasn't given a choice.

"Excellent! Thanks a bundle!" Henry said.

He jumped up and headed for the door. He stepped out and then stopped. Turning around he looked squarely at Paul. "Just let me underline one point again. This is my little girl we're talking about. I'm expecting you to keep her safe. And that includes keeping any grubby paws off her. And Paul, we're clear that means you too, right?"

The look in Henry Robertson's eyes were such that no man alive would miss the meaning.

"Yes sir, your daughter is safe with me."

***

Jane walked in from the employee parking lot in a sulk. There were no reserved spots for Robertson family members. She had to park her Beamer at the back beside a couple of grubby pickup trucks.

The guard at the main gate handed her her picture pass, already delivered by HR, and she strolled confidently into the yard looking for her contact person. She knew his name and the fact that he was fairly young but didn't know anything else about him. He would be her driving instructor.

Jane spotted a guy standing by a rig with a clipboard in his hands and talking up to the driver. He stepped back and the truck started to pull away. Walking up to him she asked if he knew where Paul Cain could be found. He turned and looked at her closely and finally said, "I'm Paul. And you must be Jane, our new driver?" He stuck out his hand towards her.

"Well if you think you can turn me into one then yeah, thats me," Jane replied with a bit of a smirk, taking his offered hand and shaking..

She looked at Paul intently in the eye but stole a quick look down to the open neck golf shirt he was wearing and particularly at the well developed chest underneath the shirt. She smiled at him. She definitely liked what she saw. She focused back on the intense brown eyes and his medium length dark hair curling on his forehead and ears. His strong jawline was covered in a slight stubble over an otherwise clean cut face. She lingered just a bit too long drinking in his features before smiling again and asking, "So when do you want me ... umm, to start that is?" She gazed at him, not sure herself if the flirt was accidental, or not. She was also thinking, 'Thanks Dad, this could be more fun than I thought.'

"Now would be good if you're ready to go. I'll give you a quick tour of the machine you'll be training on and then I'll give you your homework for the next couple of days."

"Whoa, no-one said anything about homework. I'm out of school for the summer, I just want to drive."

"This is essential stuff, firstly about the controls and features of the rig and then the Ministry of Transport rules and regulations that you will need to know to get your temporary license."

"Really! I need to do this just for a summer job? Can't we just say I read the stuff and we go straight to driving?"

"No. Your dad would never let you out of the yard without the basics. Don't fuss about it now, lets go see the vehicle."

Jane walked behind Paul, deliberately falling a few steps behind so she could get a better look. Her eyes flowed over the six foot plus frame and stopped at the tight ass in his well cut khakis and then to the wide shoulders and muscles on his upper arms. He was so much more solid then the guys she knew at school. Paul wasn't at all what she expected. She wasn't quite sure what she expected to find in a truck driving instructor but this guy was simply yummy.

****

Paul had watched the chestnut haired teenager stride towards him like she owned the place, which in a way she sort of did. He saw a very attractive young woman and a lot of attitude conveyed in a wry smile. When he stuck out his hand towards her she held onto it longer than necessary while staring into his eyes. Yes, she was the big bosses daughter but he wasn't going to let that rattle him.

Did he really think she could learn to drive? He was sceptical she would stick with it but regardless, he had promissed to do his best. Straight off, however, she rebelled against the required technical and regulatory reading. Not a good start.

Taking her over to the instructional truck he helped her into the co-drivers seat. He held her hand and then placed one on the small of her back as she clamored up into the cab. For a moment her rear was in his face and he stared at the beautifully curving ass enclosed in a very tight pair of jeans. He involuntarily sucked in a mouthful of air.

Up in the seat she swung around and saw him staring at her momentarily before turning to move around to his side. "What?" she glared at him. "Something wrong?"

"No, just remember when you are getting up into the cab by yourself to use all the hand holds."

"Yes coach," she smirked in a desultory manner.

Paul shook his head and thought, 'Smart ass.' and walking around got into the driver's seat.

"How bout we start with where I plug in my iPod?"

Paul took a deep breath, shook his head and looked over at her. "How about we start with going over the controls," he said sharply.

"Okay boss," she replied contritely, looking down at her knees. Paul's tone had registered on her. She backed off in the minor battle of wills that was apparently emerging.

After over an hour of him describing the controls and features of the cab he relented. She had been taking it all in and repeating the names and functions of the controls. There were the expected ones, gear shift, clutch, gas and signaling but the controls for connecting up and enabling the braking system on the trailer were new as were many of the other features of a modern transport.

"Okay, now we can review the stereo system," he smiled over at her with a chuckle.

She beamed. Maybe she was forgiven for being pushy.

After an overview of the impressive sound system she hooked up her iPod and dialed in a song. The beautiful ethereal voice of a woman singer flooded the cab. They both leaned back and listened. The music was beautiful.

Paul looked over at her and asked, "Laura Nyro?"

"Wow, very good. Most people our age have never heard of her," Jane responded enthusiastically to Paul's musical knowledge.

"True. How did you come across her music?" Paul asked.

"Its from my dad's collection. I know most people wouldn't think of him as liking anything other than Country and Western - he's really just an old school truck driver at heart - but he has some really interesting tastes in music."

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