Rideshare

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An out of work programmer finds a side job with benefits.
6.9k words
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Part 1 of the 2 part series

Updated 06/09/2023
Created 11/03/2019
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(c) 2019 All Rights Reserved.

This written work is Not Safe For Work! You have been warned.

Fictional Disclaimer:

i. This is a work of fiction. This work is intended for adult audiences above the age of 18. It is prohibited to provide access to any portion or entirety of this work or any information or description of the contents to any minor. This work is not intended to be read, provided to, or accessed by anyone under the age of 18 years old, age of majority, or the age of consent whichever is greater. All the names, places, businesses, incidents, characters, locales, and events herein are either the products of the authors imagination or used in a purely fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. (Unless you have video that proves otherwise, then I want to see it.)

ii. This work contains descriptions of acts that may be sexually graphically descriptive, erotic, immoral, illegal, condemned by some church, politician, state, or just unsafe.

iii. These acts may result in injury, castration, death, impotence, marriage, or worse if attempted in real life. Your admission into the Darwin Awards due to any act based upon this work is your fault.

iv. Do not take the events in this work as proof of the plausibility, legality, sanity, or safety of any particular description or practice.

v. The content of this work may not be considered or read as a depiction of the desires, opinions, or fetishes of the author.

vi. By reading, accessing, or otherwise utilizing this work you agree to wave all compensation in the event of any loss, inconvenience, damage, injury, or death to any person or property because of or while making use of the information in this work. The actions and events in this work shall not be construed as promotion or approval of those actions in real-life situations by the author.

vii. All acts, actions, and descriptions in this work are whole cloth fiction; said acts, actions, and descriptions appearing in this work may be illegal if performed in real life and can result in prosecution by law enforcement. It is your responsibility to comply with all laws, rules and regulations that are applicable.

viii. This work is not intended to be used as an instruction manual.

ix. Do not drink-drive while snogging or fucking.

x. Drinking while fucking may increase risk of pregnancy.

xi. Drinking to excess may result in injury, death and YouTube videos that you can never live down, or live to see.

xii. Drinking to incest is just bloody wrong and you deserve to be in dock. (I hope your solicitor sucks.)

xiii. Any legal ramifications are completely and totally your fault due to your actions or inactions and are not in any way the problem of the author, this includes the introduction by prison staff of any cell mate named Bubba that may have designs on your arse-hole.

xiv. Any god-like, tree-based, or blue life forms were not harmed in the making of this work.

xv. Several politicians, and the managers, accountants, and solicitors of said god-like, tree-based, or blue life forms were tormented mercilessly and left to rot following a vicious ostracising by a dull ostraciser. But they had it coming.

I am Groot.

*

~ONE~

"A ride share driver? Bloody hells, why do you think I need to be bloody cabbie? I have more than enough in the bank account to live comfortably for a few years and it's not like I can't find another job as a programmer!" I complained to my wife as she sat across from me at the kitchen table.

"Well darling, like I said, you have not found a job in the last three weeks and sitting in your office doing nothing but sending out CVs all day is driving you, and me, up the wall." Lisa said as she sipped her morning coffee.

Lisa was right, as usual. I was getting a bit uptight about not finding a new gig. Not that I had been slacking, every day I was applying for several programming positions in the city. I had sent out so many CVs in the last few weeks that I had started a spreadsheet, when one HR told me to stop sending them my information, after I applied for the same job three times from three different job boards.

Being an out of work 55 year old programmer is not something I would wish on anyone. The field is full of fresh out of university 20-somethings that are willing to put in 80 hour weeks for 45 thousand a year, thinking they will get up the corporate ladder by being a harder worker than the next guy. There were not many women in the field, so most of the young pups ignored them, to their peril. The women programmers I knew were just as aggressive as the next man and often had a sneaky way of using the female body as leverage for the next promotion. I knew several that had made lead programmer on a project through "creative manipulation" of a male supervisor. Yes, dear reader "creative manipulation" means they fucked their way to the promotion. Not that I blame them. Most of the women I know are just as horny as men and if getting stuffed full of cock comes with a promotion, that's just bonus.

"Lisa, you know I hate traffic and most humans. Why would you suggest I become a ride share driver?"

"Because it will get you out of the house for a while, and the money is good. I told you that James is driving for them in the Northwest part of the county and he's making about $200 a day. When I talked to him last night he had just dropped of a group of four at a pub and they tipped him $50. He made over $500 last night alone." She said.

"OK. I'll do it for a couple weeks, unless someone pisses me off or the money is not worth my time and gas." I said. "I don't know about going all the way over to Ramapo, but if there are fares around here I'm OK with it."

"Deal. And you get to pick and choose what fares you want. Let me see your phone."

I handed my phone over and Lisa loaded the ride share app to the device.

"Here, all you need to do is tap this icon. I've already done all the rest." She said as she smiled at me. "It's already logged in and running."

"You what?" I asked as I realised that my lovely wife had once again preplanned my life for me.

"The X5 is full of gas, so you should be good for the day. Go get dressed and go meet some people." Lisa came around the table and kissed me. "Have fun on your first day at work, darling. I'll be at the salon with Candice, see you tonight."

With that she picked up her purse and headed out the door.

"Bugger." I mumbled under my breath.

I went back to our bedroom and changed out of the old shorts and t-shirt that had become my daily wear, unless I had a video interview when I would put on a nice Brooks Brothers suit and tie. Well on top I was all BB C-Suite professional, but under the table I was in a pair of shorts or sometimes just a pair of boxers.

Several days ago, I even skipped the boxers for one interview. Lisa had walked past the office during that one, realised it was not going at all well, and had slid under the desk from the other side. Before I know it, my wife had started sucking me off as I tried to keep a professional look for the lady who was doing the interview over the Linked-In VTC service. It was all I could do to not look like I was passing a stone when Lisa took my entire cock in her mouth and gargled with the head of my cock past her tonsils. I had to ask the interviewer to repeat a question when Lisa made me cum in her mouth. The woman ended the interview after that and disconnected with curt good by and a look of disgust at the end.

Lisa had gotten out from under the desk by then and was sitting on the corner of the desk with her legs spread so I could see she was wearing nothing under her short skirt.

"Good interview darling?" she asked, clearly knowing the answer.

"Better than most, all things considered. I'm quite sure that bitch would be in my supervisory food chain and she needs a few hours in a smelter before the ice queen could defrost her cunt enough to get fucked." I replied.

Well, you are in luck," Lisa said as she opened her legs wider. "My pussy is nice and warm and in need of a good hard fucking right now."

I slid out of the chair and turned Lisa around as she bent over the desk. Even though she had just gotten me to shoot a load of cum in her mouth, I was already hard again. I lifted her pleated skirt and after a sharp spank on her exposed arse cheek I stuffed my shaft all the way into her cunt. She was right, her pussy was hot and she was wet as always. Lisa was one of those women who never needed any lube, her cunt dripped at the slightest hint of arousal. More than once she had needed to excuse herself to go and dry up and change panties because she got aroused at a party or even if we were just out shopping if I started teasing her.

I fucked her to several wet squishing orgasms before I came in her. After I had pulled out, she stood up and sat back on the corner of the desk and put her fingers in her now cum dripping pussy and pulled out a dollop of my sperm. Licking her fingers, she commented about how I was a bad boy for leaving a nice big wet spot on her skirt.

~TWO~

For my first day as a ride share driver I had dressed in a pair of Brooks Brothers slacks, a dark blue polo and pair of Red Wing casual dress shoes. After thinking about it for a few moments, I pulled my Sig Sauer P365 out of the bedside gun safe and slid it in the shoulder harness then checked to make sure the two spare magazines were full on the counter balance side. I pulled a tan jacket on over the holster and checked in the triple mirror to make sure I did not print or show that the rig was under the jacket. Satisfied that short of a pat-down, no one would know I was carrying, I headed for the BMW.

I had just put the phone on the induction charger when the ride share app chimed. I pulled the app up on the cars infotainment display and saw that the ride was from just down the street to the local market. I accepted it and headed to the address.

I pulled up to the walkway and stepped out to open the rear door for a young woman and her son.

"Good morning, madam. I am James and I'll be your driver for today." I said, considering that a proper Englishman should know how to butler, chauffeur, footman, and chef. Knowing how to do the laundry and dishes was just a bonus.

The lady seemed taken aback. "Um, hi. I'm Mary and this is Michael." she said as she climbed in and started getting her son buckled in.

I closed the door once she was settled and returned to the drivers seat. "The A&P this morning, madam?" I asked to verify her destination.

"Yes please, James."

"Very good, ma'am." I said as I pulled away.

The store was only a few miles and traffic was light. As I pulled up to the store enternce I turned on the four-ways and then got out to open the door for them. Mary seemed surprised at the treatment.

"You know something James, I have been using ride share and Uber for a while and I can't think of a time that any driver has opened the door for me."

"Ma'am, it is my pleasure. A proper thing it is." I said.

"Mom, he has a funny accent and talks odd." Michael said.

"Well dear, he is British and the Brits tend to be more refined. You remember that the more refined you are, the more women will find you more attractive." Lisa told her son. "Again, thank you James."

"Will you be needing my services for your trip home, madam?"

"Um, well I guess yes. I usually just use the app for another driver but I should not be more than 20 minutes, if you don't mind?"

"Not at all, ma'am. I shall await your return." With that I closed the door and pulled around to park in a spot where I could watch the exit from the store. While I waited I scanned the professional jobs boards still looking for something back in the programming field.

Almost to the minute, I saw Lisa and her son walk out of the store with a shopping cart holding several paper bags. I drove up as Mary just got to the curb.

Once again I got out and having already hit the button to opened the X5s hatch I walked around to open her door.

"I'll load the bags ma'am." I said as I walked up to her.

"Um, thank you James. I must say that this is really different. All the other drivers just sit there and wait for me to load and unload everything. You are spoiling me."

"Just doing my job as I see it, ma'am."

Bags loaded and Mary and Michael in the back, headed back to their house.

Pulling up to the front walk, I again got out and opened the door for them. Then, I stepped back to the hatch to retrieve the grocery bags. "Ma'am, would you like me to carry these in for you?"

"Um, if you don't mind? Michael you get two of the bags, please?"

I handed her son two of the lightest and took the remaining three in my arms then followed her and her son in the home. Mary lead me to the kitchen and asked that I just leave them on the centre island.

"Thank you, James. You really have been a huge help." Lisa handed me a $20 as a tip and then gave me a quick hug and a soft but brief kiss on the cheek. "I hope I have you as a driver again."

"It was my pleasure, ma'am. Today is my first day as a driver, so I don't know if you can request someone but I'll keep your address in mind if I see it come up again I'll be sure to accept the fare if I am available."

"Well I use the service quite a bit, I hate driving, so it's quite possible I'll see you again." She said with a smile.

"I look forward to the next time. Good day to you ma'am, young sir." I said as turned to head for the door.

The next few hours were much the same, pick up a fare, drip them off. Always with the curb side service that I was raised on growing up in England. Granted, my family carried a Title and I was technically a 'Sir' having been Knighted KBE for actions taken in a combat tour during my service in Her Majesties Royal Air Force. A tour that just happened to allow me to meet Lisa, an honour most high. The KBE was just a side event.

~THREE~

Several days went by with much of the same. Lisa was right, the pay was not bad, but much of it was from the tips. The actual pay from ride share was enough to account for gas, wear and tear on the car, daily washes and the occasional vacuum between fares with a couple dollars per hour left over. Without the tips, a ride share driver was not going to be living on much but pot noodle and crackers if they had a rent more than few hundred a month.

Just as I was getting started one Friday, I saw Marys address come up in the fare call app. I quickly accepted it and although I was over ten minutes away, I was still the closest free driver. As I pulled up to the curb in front of her house Mary came out talking to a young girl. She gave the girl a quick hug then started to walk to the car with her head down looking at her phone. As she approached, she realized I was her driver and a big smile lie up her face.

"James! Great to see you again." Mary said as she came and gave me a hug and a kiss on the cheek. "I completely forgot to look to see who the driver was on the app. I am so glad it's you."

I could tell she already had a few drinks this evening and was glad that she was smart enough to call for a ride rather than drink drive. "Hello Mary, out for an evening on the town, are we?"

"Yes, girls night out. Look out boys!" She said as she hugged me again.

I returned the hug gently, noticing she did not seem to have a bra on under her short tight dress. "Well, I will say that the 'boys' have their work cut out for them this evening."

Mary got in and after she had her seatbelt on, I closed the door and got back in the driving seat. "Mary, I can't help but notice that you listed Feathers as the destination."

"Yes, one of my girlfriends heard it's a hot little bar and wants to check it out for prospects."

"It's not my place to say what someone's lifestyle is, but I think I should caution you that Feathers is a, well not to put too fine a point on it, but a bar where the men are not exactly looking for ladies."

Mary took some time considering my comment. "Wait, what? What did you just say?"

"Mary, Feathers is a queer bar." I said simply. "I thought you should know, as you don't, if you don't mind me saying, seem the type."

"What? OH my GOD!" Mary was quickly on her mobile talking to another of the group that she was off to meet.

"Did you know what bar Sue has us meeting at? Yes, Feathers. No, it's not. No. It's a gay bar! Yes! Yes, I'm looking it up now. Oh my god, no! No, I'm not going there. No. Well if you want. OK, I'll meet you there. No, I'm not calling her. Well, OK. I'll do that. See you soon, bye."

"Oh my god, I can not believe her. James, can you take me to the West Gate in Nyack? I know it's a bit of a drive, but.."

"Not a problem, Mary." As I took the next turn to head to the NY border, I looked in the back to see Mary texting. She spent the next several minutes texting as I drove.

"Well, Sue is still going to Feathers without the rest of us. I'll be interested to hear what she has to say tomorrow." she said after putting her phone in her purse.

"Mary, I am sure it will be a story of a very boring evening, or a story that she may not be willing to share." Either way, I hope she stays safe. That is not a very nice area and one that I encourage no one visit after dark."

A bit later, I pulled up to the front of the WG. A nice salsa dance club that that I been to several times with my wife and some friends who worked across the river at I've Been Moved. Decent food, a good bar and usually 'interesting things' to look at on the dance floor. Here we are, Mary." I said as I got out to open her door.

Mary opened her clutch and gave me another $20 as a tip, "Thank you James. I don't think you will be my driver for the ride home, but I want to thank you for keeping out of Feathers. I don't think that would have been a good time." then gave me tight hug and a kiss in the cheek.

"You are very welcome." As I hugged her back I heard my phone chime for another fare. A moment later it chimed again. "Well, Mary, it seems as there is quite some business in the area so I may still be around when you are ready to go home." Without really thinking about it, I handed her my business card with my personal cell number. "If you need anything, give me a ring."

Mary took my card and slipped it in her purse. "James, thank you." Giving me one last hug she went inside to find her friends.

I got back in the BMW and looked at the fare waiting list. There were over a dozen within a five mile area. I selected one that was just up the road and continued on with my evening.

Several hours and more than a dozen fares later my phone rang. "Hello?"

The girl on the other end was one of Mary's friends who had called to see if I was available to take her home. Mary had reached a point of drunk that they were not comfortable letting just any ride share driver come get her. Mary had been telling them about her 'regular' ride share driver and how he was the perfect English gentleman. The business card convinced them that I was not a threat to her in her current condition and consented to calling me.

I had just dropped off my latest fare at a pub up the street and told the girl I was just two minutes away and would meet them in front of the pub.

As I pulled up, I saw Mary and a blond sitting on the bench out front. Mary had definitely had one drink too many and was unsteady as I opened the car door for her.

"No, I want to sit up front." Mary said as she reached for the other door handle.

I glanced at her friend who just shrugged.

"Very well, Mary. Let us get you buckled in." I said as I helped her with the seat belt. As I leaned over her, Mary leaned forward and kissed my neck.

"Thank you James."

"It is my pleasure, Mary." I said as I stood back up and closed her door. "I'll take her home and make sure she is safe." I said to her friend.

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