Walking the Dog

Story Info
Young man working for an older woman, not the usual story.
4.2k words
25.8k
11
0
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

I was asked to write a story about a young man working for an older woman in a large company. For this story I put myself into the young man's point of view.

Story Code: M/F, MM/F, Voyeurism, Exhibitionism, Public Sex, Dogging

I left school at sixteen, went into an office, I was the only man, well, boy that started that year. The company took on ten office juniors each year and they had a two year training program and they never kept more than two of the juniors on after the training period. The company, which I can't name here for obvious reasons, was a long established, nationwide company with long established practices and procedures.

At eighteen I was given a post in Customer Services, a CA2 post, that meant that I got to do photocopying and filing and could be trusted to make coffee, it was made clear to me that I would have to work for five years as a CA2 before I would be considered for promotion to CA3, mainly because it would take five years to work my way around every section in Customer Services but also because that was one of the unwritten rules, minimum five years in post before promotion. The company was the kind of place that people started working for straight from school and worked for forty-five years before retiring and very few got as high as a CA6 before then, definitely a case of 'Dead-man's shoes'.

I hadn't planned on stopping, I wanted a more exciting job, something with freedom and travel but, I got a CA3 at twenty-three, which gave me a thousand pound pay rise and the chance to deal with customers on the phone and field staff on the radio. I had friends who had left school at the same time as I had and not one of them was earning anywhere close to what I was earning. I was a keen sports man plaid football, badminton and tennis, so I was fit and muscular, just over six foot tall.

Against all expectations I got a CA4 at twenty-five, by rights, I shouldn't even have been allowed to apply for it after only two years in my CA3 post and my workmates made it clear that they didn't appreciate my meteoric rise through the company. At twenty eight my team leader took me into a conference room, the company were looking at a different way of interacting with customers on the phone. We had two telephonists who sat in a quiet booth, the calls all went into them first, they decided who you needed to be connected with and put you through. The new idea was to have twenty staff who were experienced in all areas to take the call and deal with it without putting it through to anyone else. Because of the skill level and knowledge base required there would be twenty new posts created at CA6 grade, now that was serious money. "Mrs Benbow has asked me to have a word with you, nothing will be announced officially for six months and then it will take a further six months to get it up and running in every office, it's up to you, if you want to be considered, you have to get experience in dealing with enquiries in every area in just six months!"

Mrs Benbow was a principal assistant, if you believed the 'locker room' gossip, she was the youngest ever principal assistant and she had slept her way to the top to get there, at forty she was still very attractive, her mind was very sharp and from the little I had seen of her she had a wicked sense of humour. I told my team leader that I would be keen to try for it.

I had just six weeks in each area, I had to go into Engineering and commercial as well as customer services and get training in every kind of enquiry that was possible, the worst section was complaints. The staff in complaints were the worst in the business to work with, every one of them were as miserable as sin, totally negative about everything, comes from having people moaning at them all day, every day. I found myself agreeing with the customer ninety percent of the time, their requests often seemed very reasonable to me and I noticed that a recurring problem was that they had spent hours on the phone being passed from one department to another and when they lost their temper due to frustration they always ended up in complaints. I started to try and fix the problem instead of just recording the complaint and getting a letter of apology sent out. It was a good thing that I had been to all the other areas before complaints as I had the skills and knowledge to fix almost everything.

I was the only one in Complaints that had a good time, I actually looked forward to going in to work, I spent less time in the toilet, less time at the coffee machine and the day that I got a pensioner on the phone in tears because we had messed her about so much and to compound things we had inflated her bill for the work too, as she sobbed through her tail of woes, I asked her if I could look into things and phone her back, "Well, I know that you won't phone me back, I'll be back on tomorrow to go through it all over again with another faceless drone!" And with that stinging comment she hung up the phone.

I sat for a moment mulling things over, Mrs Benbow had started me off on this course of training and up-skilling, I could just have made a few calls, erased a few computer records, recalculate the bill and that would have been that, that would have been the 'face-less' approach. I called the complaints team leader and asked for permission to leave the group, then I searched for Mrs. Benbow's phone number and called her, I detailed the complaint, mentioned the lady's age and how upset she was, "What do you want to do about it?"

I was on my guard now, there was no signs of agreement with me, she just asked what I wanted to do about it. "Well, if it were my own company I think I'd be out buying a bouquet of flowers and delivering them to her and telling her that I'd wiped her bill!"

There was a long pause, "You have a driving licence?"

"Yes!"

"Have you been cleared to drive company vehicles?"

"No!"

"OH, that's a shame, give me five minutes!"

Two minutes later Ray Weston walked over to me, he was manual staff, it was hard to place him in the structure as manual grades didn't line up, well, we seldom did anything together, Ray was in total charge of all safety matters, "Get your coat on, it's cold outside!"

"Are we going somewhere?"

"Driving test!"

I jumped out of my seat, grabbed my jacket and followed Ray into the car park. I had to go through a series of manoeuvres in a Metro van, the same series in a maestro van and again in a Ford Transit van. Then Ray took me to a large black BMW six series saloon car. I didn't need to know the car, the parking place was marked Mrs Benbow, Ray got in the passenger side and I in the drivers, I was directed out of town and on to the dual carnage way and told to get up to speed. I had never driven anything like it in my life, the power, the speed and the handling were all impeccable, there was a bonus too, the smell in the car was wonderful, expensive scent from the car's usual owner.

Ray added me to the list of recognised drivers and gave me the ignition key to the BMW. "You need to pay for the flowers yourself and claim the cash back, if you come to me I'll counter sign the expense form and when you have the final write off figure for the bill, I'll have to counter sign that too, it's going against health and safety just this once!"

I was almost walking on a cloud, I was being allowed to deal with that vulnerable little old lady as if the company were my own. When I knocked on the customer's door and handed over a bunch of flowers and told the lady that the bill was being cancelled there were more tears, but this time tears of joy.

Overnight I was getting all the worst complaints, all the complaints that the rest of the team couldn't resolve and at the end of each day I had to go into Mrs Benbow's office to give her a breakdown of what I had cost the company each day, she was less interested in the problems or what went wrong, just what I had done to sort it out.

I was just coming to the end of my time with complaints team and I was in Engineering trying to talk them into replacing a cable that had been laid in a place that worried the customer in case they hit it while digging their garden. As an aside I asked if the engineer knew of any parking spaces close to Market Street as I had to pop out at lunch time to visit a shop there, Mrs. Benbow was in the room too, she came over, "Can you lend him your car John, your car has the electronic tag and can park in the substation in Market Street can't it?"

John just handed the key to his car and Mrs. Benbow took me by the arm and led me away, she needed something picking up from the fancy dress hire shop and wanted me to do it while I was in town for myself. I was even given extra time, the team leader in complaints was used to me nipping out to deal with complaints face to face so an extra long lunch break wouldn't come as a surprise.

I did my shopping and then went to the hire shop for Mrs. Benbow, I had just expected to pick up a suit bag and head back to the car, how wrong I was! I had to inspect the costume and sign for it, the costume was a very sexy nurse's outfit, not the kind of thing that a man would expect to pick up for his boss. In the office I was asked by several of my colleagues what I had fetched for the boss, I just told them that I had no idea and kept my mouth shut.

Mrs. Benbow must have had spies in the main office because when I went in for our daily meeting she thanked me for not breaking her confidence. That started a much closer working relationship, I had proven that I was trustworthy and knew how to keep my mouth shut. I had even been invited to lunch one day when Mrs. Benbow needed someone to unload onto. We were in a local pub, company rules stated that you were not allowed to drink while at work, Helen Benbow downed almost a full bottle of wine as she told me that things at home were strained. I was a single man, living alone in a one bedroom rabbit hutch so I couldn't offer any advice on relationships. I walked back to work and Helen drove home.

Well I didn't find out for six weeks that as she drove home Helen had been clocked doing one hundred and twenty miles an hour on the M6 motorway, I wouldn't have found out then but for the fact that she had to go to court in Birmingham and because of the speed and the fact that she managed to evade the police car that had chased her, she was banned from driving for six months. The first I knew of it was that my phone rang; I could see from the screen that it was a call from a mobile phone, "I need you to meet me in Birmingham!"

I had never received a phone call from Helen Benbow's mobile phone before, so I didn't recognise the number, "I'll have to check with facilities but I can see two pool cars in the car park!"

"No, I need you to come over by train, Find Ray Weston, tell him I'm asking him to get you to the railway station as soon as possible!" I was given the details of where she wanted me to meet her and she hung up on me.

I was about to call my team leader and tell her that I needed to go out when I saw Helen's number appear on the little screen on my phone, she was ringing my team leader, there was a very short conversation and then my boss came over with a hand full of papers, all complaints that I had dealt with in my own unusual way. "Mrs. Benbow needs these in our Birmingham office five minutes ago, you're turning out to be one of her 'Blue - eyed boys' at the moment, just watch your step!"

I put on my jacket and searched around for Ray Weston, as the head of safety and the manager of all customer service field staff he could be anywhere, anywhere that was apart from his desk. I found him in the garage workshop, Ray wasn't in charge of the garage but he was in charge of the garage staff, I told him that Mrs. Benbow needed him to get me, and that was as far as I got, "Not interested in the how, the where or the why, just tell Gordon where you have to be!" Then Ray called out to the junior mechanic, "Gordon, pop out now to get the parts and on your way, drop Mr. Roberts here off where ever he wants to go, and I don't want it recording in the vehicle log OK!"

So I found myself in a grubby old Transit van heading for the railway station, I had to take a taxi to a restaurant where Helen was having a liquid lunch, I was given the keys to her car and I got to drive her back to Nottingham, suddenly she changed her mind, she was supposed to be at a seminar to do with new ways of dealing with complaint resolution. Helen directed me to Coalville, as we drove along she was telling me that she was leaving her husband, the driving ban had sped things up a little though, there was a word of warning as well, "I expect the same level of discretion over this matter as you showed over my fancy dress costume, if you know what's good for you!"

Once in Coalville I was directed to drive to Snibstone Discovery park, the main car park was empty except for two busses, so the place would be full of school kids, "Drive on, go through to the overflow car park!"

I was told to stop at the side of a gate that opened into a footpath that went up and over a hillock and into a small spinney. We sat talking, thirty minutes later a car pulled up right next to us, there was just the driver in the other car, he had pulled up so that he was as close to Helen as possible, he kept trying to look down into Helen's car, as if he was trying to look at Helen's legs, he had a disappointed look on his face, then Helen turned her head, I could see from the reflection in Helen's window that she gave the other driver a sweet smile and a coquettish wink. The guy's face broke into a broad grin and he got out of his car, locked the door and headed for the gate.

"You have a condom?"

"What?"

"Do you have a condom?"

"No!"

I only said no because I had no idea why Helen was asking me. "Come along man, your young, free and single, you must have the 'just in case you get lucky' condom in your wallet!"

"Well, I have one but it's been in my wallet for four years!"

Helen did a double take when I said that. "Four years, I go crazy after four hours, come on, hand it over!"

I passed Helen the condom; the foil was cracked and almost broken through in places. Helen took the condom and opened the door, "Wait here for me!" Helen had left her handbag on the floor of the car and had set off along the path after the man from the other car.

Ten minutes later Helen's phone rang, I picked it up and answered it, typically, in situations like this, the one person you don't want to phone is the very one who does, the MD wanted Helen urgently, I had lied that she was in the bathroom and that I would wait outside the door and get her to phone him back as soon as she came out.

I took her handbag and the phone and set off after her along the path, I followed the path into the spiny and just a few yards into the woods I stumbled across both Helen and the man from the other car. Helen was bent over, both hands holding on to a Poplar sapling's trunk, her white cotton blouse was open and her bra was pushed up under her chin, her long skirt rucked up over her hips and no sign of panties. The man was humping her from behind, bent over her back as he fucked her and fondled her tits. They both looked at me as I crashed through the scrub, neither one of them seemed to care that I was there, the man continued fucking her for five more minutes before grunting through his climax.

I watched as the guy slapped Helen's bottom, then tied a knot in the condom that I had supplied and tossed it into the bushes, I followed the arc of the condom and saw it hit the top of a small pile of similar tied condoms on the ground. The guy rushed past me with a smile on his lips, Helen just stood there in the same position, hanging on to the sapling for support, breasts hanging free, she was just looking at me expectantly, after five minutes of me explaining that the MD had phoned and wanted to talk to her urgently. I wasn't sure if Helen had been waiting for me to follow the guy from the other car and stand behind her and fuck her, not the kind of thing that anyone would think of doing uninvited to their boss though.

Helen stood there, still naked on top, her skirt had fallen down to hide her neatly trimmed bush. She chatted to the MD for a few minutes and then looked around the footpaths and as there were no other men around she started to walk back to the car. I looked around the ground and the branches, she didn't have her knickers in her hands and they weren't covering her arse so I assumed that she must have put them down somewhere.

"What are you looking for?"

"Your knickers!"

"I never wear any!" And with that we were back in the car.

As I drove Helen home, plans were being made for Ray Weston to find an empty transit van, and put the keys on Helen's desk, I was going to drop Helen off at home and then take her car back to the office, I would go home in my own car and then return in the morning and pick up the transit to help Helen move into a new flat that had recently been built close to our office.

Officially we were both still in Birmingham at the seminar, I just had to be very careful while driving close to our office on each trip so that no one who knew me saw me, especially as I was driving a company van. I had left Helen in her house to gather her last few possessions while I took the van, filled with boxes of books, records, knick-knacks etc, as I left her house she told me to stop off on my way back and get a box of condoms.

There were only a few bits left for the final trip; surprisingly one of the items was a double bed mattress. I propped the mattress against the side of the van, Helen pulled it flat on the floor of the van. Helen didn't want to go straight to her new flat, it was lunch time and there would have been a greater risk of us getting caught by one of the other workers from our office. Because of the extra height of the van, the number of car parks that we could visit were limited but Helen seemed to know every one of them.

Once again, we had only been parked for a few minutes when a car drove in next to us, the man got out and stood, smoking a cigarette and staring through the side window at Helen. "Please tell me that you got some condoms!" I passed her the brown paper bag that had a ten pack of 'Mates' hidden inside.

Helen openly took the box of condoms out of the paper bag and held the box so that the guy could see them. "Reverse over there; get the back doors as close to the bush as you can!"

I started the engine and reversed across the car park, as the back of the van got close to the bushes Helen told me to stop. "Wait there!"

Helen got out of the passenger door and walked to the back of the van slowly, swishing her hips as she walked, Helen wasn't dressed in her usual tailored blouse and ankle length skirt, she had a very loose fitting summer dress on that showed off her voluptuous figure and flicked up extremely high at the hem with every step she took.

Helen opened the back doors of the van and stood in-between them as if she were looking for something in the back. The man who had just finished his cigarette walked over to the back of the van, he had to squeeze between the open door and the bushes to get into the space between them and the van. I got a grandstand view of the two of them through the rear view mirror as the man began kissing and fondling Helen, as he lifted her dress I could clearly see that she hadn't any panties on. Helen was stripped totally naked, fortunately no one but me could see her, eventually the guy opened his fly, skinned a rubber onto his cock that Helen, or rather I, had provided, the mattress was used for the guy to actually fuck Helen so I had a wonderful view of this older woman being royally fucked.

The guy was rocking the van quite a bit as he fucked her, the rocking had attracted a little interest from several men who were milling around. I was surprised to see a second man slip between the doors and the bush; he stood there watching close up as Helen was being fucked. The man in her finished off, it had taken him a long time to climax but Helen hadn't come anywhere close. After the first man, there was a constant stream of men, until all ten condoms were finished off and in all that time, all ten men, Helen didn't seem to come anywhere close to her own orgasm.

12