Summer Driving Job

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College student lands summer job driving rich single lady.
2.3k words
4.34
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Part 1 of the 2 part series

Updated 10/19/2023
Created 08/04/2023
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Summer Driving Job

First Student had helped me get my commercial license to drive school bus charter trips for some of their customers. Since I was seen as more responsible than some, I'd been given the additional training for diesel, air brakes, and passenger endorsements. I'd posted an online 'job seeking' page for some summer work, describing myself in the most glowing terms, touting my experience in driving large fully loaded school buses and explaining that I was looking to 'ferry' or move motor homes for people.

I'd traded a couple emails with a lady who was interested in hiring a driver for the summer. Seems as though she was retired and had recently purchased a very nice motor home, but her friend of many years had broken up with her, and she didn't really like driving anything that big. She liked taking summer vacations because even though she was retired and semi-actively oversaw a real estate brokerage firm she owned.

Arriving at her home in an upscale neighborhood of homes with three and four car garages on very large lots, I drove up the driveway to the garage nearest the front door. I was very pleasantly surprised when a not too old, attractive woman opened the door.

"Hi, you must be Kenny. I am Maggie, short for Margaret. Please call me Maggie."

"Hello Maggie, nice to meet you. Very nice place you have."

"Thanks you, yes it is nice. Partly from my hard work and good luck; and also a bit of a contribution from my ex-husband." Holding the door wide open, she beckoned, "come on in. Can I get you a coke or beer?"

"A coke would be fine. Thanks."

"Sure, no problem. Have a seat in there." As she pointed to the lounge to the side of the entryway, and headed for the kitchen. "Make yourself comfortable at the table, I'll be back in a minute."

I sat down facing the large picture window at the rear of the house, realizing that I was settling into a nice leather chair. Looking around I saw the room was tastefully decorated and while quite nice was not lavish or gauche.

"Here you are" as she sat a glass full of ice in front of me, with a full Coke can beside it. She sat in the chair across from me and sipped her glass of wine before continuing.

"Kenny, this summer is supposed to be hotter than last year...and that was hot enough. My summer long trip is to beat the heat as much as possible. I want to hit a few places going north east, but our objective is Canada. We'll go out through Maine to Nova Scotia and Prince Edwards Island which is as far east as you can go in Canada or North America. From there we'll work out way west and wind up 10 weeks later in British Columbia. That is nearly 6,000 miles before we come back home which makes it 7,700 miles and about 120 hours of driving. Think you can do that? Want to do that if I pay you well? Can you put up with me that long? Ha!"

"My gosh, that is a long trip. What a summer job that would be. Quite frankly, yes to all your questions. I'd find it exciting. I do love to drive and see places I've never been before. Once we get past Pennsylvania, everything will be new to me so yes, I'd love it."

"Do you have a passport? Ever been out of the country? To Canada?"

"Yes I have a passport and I've been to Mexico and Europe several times. My step dad has family in Germany and we've gone there every other year. But this year I'm free to do what I wish...especially to earn some money for college."

"Ah nice. Do you have financial assistance too?"

"Well I have some academic scholarships from my grades and scores on the national tests. I have a trust fund from my father's estate with part of it specifically for education. So I'm thinking I can get out of college someday...probably debt free. That is my goal."

"Awesome young man. Very good plans. Commendable, and congratulations on your good performance so far and I'm sure with your focus it will continue."

"Thanks, I sure hope so. Thank you for the nice remarks too. I appreciate the reinforcement."

"I've traded...returned would be a better word...my 45 foot Winnebago and purchases a 28' Born Free which is much more maneuverable and better suited for what I have in mind this summer. You ever driven one that size?"

"Yes, I've driven busses considerably larger...as large as your Winne...so the 28 footer would be nicer for that long of a trip, moving all the time. Yes, good choice. Born Free's are nice rigs. I've never been in one but have seen pictures and know they are well built and very nice inside."

"Want to see it? Best to lay eyes and hands on it to get a good feeling?"

"Oh fur sure. Is it in one of your garages?"

"Well not quite. It is in the 'barn' in back of the house. It is essentially another nice double garage with high opening doors. Come on let's go see it."

~~~~~

"Wow, this is really nice inside. I see it has a good sized gas engine which is good for this kind of a thing. Diesels get better mileage but are more problems and I'm glad it has a gas engine."

"Yes it is fully contained. The shower is nice sized and the kitchen is very adequate. The one slide out makes for a very nice bedroom." Putting her hand on my arm, Margaret looks directly at me, "and it is set up for one bedroom as you see...we need to talk about that later." With that she showed me the rest of the RV pointing out that it has a large fresh water tank, and both gray and black water storage tanks that are very ample in size. "We'll have to find places to dump every two or three days I'd expect, and there should be fresh water to fill up at the same place."

"Yes I understand. I've done some of that in the RV that my grandpa left me. It is very small but has all the same basic things in it. I've done some fun traveling in it and something this size could be a lot of fun."

"Oh nice, what is it?"

"It is a RoadTrek 190 Poplar."

"Well Kenny, I do know what those are. That is great that you have had that experience, and plenty of experience in big vehicles, I am sure you can do the driving part. Let's go back to the house and talk about the living part of the summer."

On the way back to the main house Maggie invited me to have dinner with her. She explained that she was not above some decadence and had a really good carryout and delivery place that put together good meals for her, and asked me my dinner choices. We quickly zeroed in on some Italian sausage lasagna and she ordered that before we got to the house. She explained that she had plenty of wines to choose from, and even a couple kinds of beer, so we were all set. My mind was wondering what the meant by the living part of the summer. I was also curious about the one nice bedroom in the slide out. I guess there was a drop down above the driver or somewhere that I would sleep. Or where?

We were well into the great lasagna when Maggie looked at me and asked, "Kenny you have a girlfriend that is going to be troubled by you being gone all summer?"

"No not really. I have dated several girls in school, and like some of them a lot, but I have not gone steady and prefer to keep my options open for a good while yet."

"That's smart. This is a lot more personal question, and I do not want to shock you but we do need to talk about some things."

"OK."

"I do not know how to really do this. I have an important objective...just do not know quite how to get there. So I'll try. Please be patient. You can give feedback too along the way. OK."

"Sure."

"Kenny, have you been 'with' a girl? Slept with a girl, or girls? Had sex?"

"Yes I have."

"Good. This is very personal and I won' t push this too far...but how many girls have you been with and did you have sex...say...more than 10 times total?"

"I have been with three girls, and yes more than 10 times...but that was with one of the girls. I like her best and...well...sex was really fun with her."

"Great. Kenny, there is really only one good sleeping facility in the Born Free. You by now are beginning to know where I am headed. We'd be spending three months in close quarters. It will be a lot nicer...for both of us I think...if we are 'friendly'."

"Yes. I understand. I agree."

"Kenny, do you find me attractive? Desirable? Just a little bit sexy? What do you think about sleeping with me most every night for the three months? Be honest please. You can think about it if you want to."

"I don't have to think about it at all. Yes. Yes you are attractive. Yes you are desirable...and hot. I'd say yes you are surly a MILF."

"Mmmm good reply, but I do not know what MILF means. Can you explain?"

"Oh...mmmm...well...it means Mom or Mother I'd Like to Fuck."

"Oh wow. Nice. Now I'm the one who has to think about what I want to say or ask next." After a pause, "Oh yes, I need to say just because we are sleeping together every night does not mean we have sex every night. Does that make sense?"

"Sure, I understand."

"Kenny, I feel kind of weird about this to be honest...not that I don't want to do it...but how I'm going about finding someone to go with me. I had no idea but to run the ad, and then be upfront and honest about what I expect. Makes me feel kind of cheap in one way...and makes me exhilarated in another since I think about what this summer might be like...with a man like you. Wow."

"Well it is very unusual...I never heard of anything like this...but it is not weird. You are not weird.

You are a bright...successful woman...who is going after what you want and have the capabilities to do it...so while it may be unusual...it is not bad, weird or anything but good."

"Ok, one last thing...which I think I want to come back to after we talk about money and things. That is a bit of a sample. Sex with you. Yep...before this becomes a deal...I want to spend some time with you...on a very intimate sexual basis. OK?"

~~~~~

"I'd like to leave here the first of June...as close to the first as possible. I've made a rough outline of the route and timetable, with us getting back here the last part of August. While I can drive the RV, it is important to me that you spend the entire time with me...I'll be counting on you."

"I understand that. We'll have cell phone service most places and internet too I assume?"

"Yes most places, but we'll be in some pretty sparsely populated parts sometimes and service will be very spotty there. Only around the towns."

"That will work just fine. I can keep in touch with friends, and do any school preparation I need, so it is good. Sounds nice."

"Kenny, I'll pay for all our food and expenses so you will not need to spend much money at all during the summer. So what you make will be all pretty much savings. This brings me to how you want to get paid. I can pay you basically in cash, and not do any W2 withholding...or I can pay you a bit more to offset the income tax, and more or less make you an employee and you'll get a 1099 statement for the wages and income tax paid at the end of our trip. You'll have to file Income Tax but I will make it so the tax is offset with the extra I pay you. OK?"

"That is great. I'd like to get paid so I have income to pay taxes on. With the income from my dad's trust and the things my grandpa has given me, I already file income tax so it is not a big deal."

"Kenny, I can afford to pay you well. I'd like to offer $2,000 a week, or basically $26,000 for the 13 weeks we'd be gone."

"That sounds great. Very fair."

"I'm not done yet Kenny, When we get back, I'll pay you an additional five weeks...$10,000 for a 'trip completion' bonus. I do want to insure you will be with me the entire time. Ha...just in case the pay... and sex...is not enough."

"Oh gosh Maggie, that is more than fair. I accept if you offer me the job."

Ok, good. Do you have the rest of the evening open? Did you bring a toothbrush? Can you stay overnight? I'd really like that...if we can sleep together...as our 'trial run'."

"Mmmm...yes to all of those. With pleasure. Absolutely!"

"Then as a way to start the rest of our evening, I suggest we take a 'low light' shower together and then get in bed. I have had my tubes tied, so I am safe from getting pregnant. I also am pretty sure that I have no STDs since I donate platelets regularly and they check me each time. If tonight works as well as I think it will, I would like to pay for you having a complete physical, including you getting checked for STDs...and then we can have sex without worrying about condoms all the time. How does that sound?"

"That sounds amazing. To be honest, I've never had sex without a condom...so that will be awesome."

"Oh, I agree. Let's get that shower now."

~~~~~

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27 Comments
maddictmaddict3 months ago

Let me think it over - OKAY

Master_Rocky106897Master_Rocky1068976 months ago

Very interesting and can't wait till the next chapter is written and submitted looks like a possibly long series

AnonymousAnonymous7 months ago

Yeah...

No

Doctor74Doctor747 months ago

Interesting storyline, please write the follow up.

Chimo1961Chimo19618 months ago

Awkward and unreal, and unfinished

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