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First Published: 14 February 2023

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New Clerical Apprentice
by Isabella

Story Codes: M/F, oral, Voyeurism, Exhibitionism

I'd been struggling with my new assistant for a year, his name was Simon and I say was because he upped and quit in the middle of last week, leaving me in the lurch but as he wasn't a very good assistant, I didn't have any more work to do, in fact my workload diminished slightly because I wasn't having to check his work all the time and sort his messes out.

An email from Human Resources promised me that I'd get one of the new starters who were due to start work on the first of the next month, I phoned Tony Cooper our HR manager to see what he could tell me about the new bunch of employees but the phone was answered by a new voice. Tony had been moved to head office down in London. I introduced myself and asked what information they had on my new assistant.

"Well, we have three students fresh out of university, all with reasonable degrees and keen as mustard to get on and we have one local girl, she's joining us as an apprentice so now I have to find out all about the rules for clerical apprentices!"

Well, there was no gender mentioned for the three older prospects...people in HR generally careful to de-gender their conversations but he had let the 'Local Girl' slip out...now, if Tony Cooper had still been sitting in that chair, I wouldn't have got a look in at a female assistant, he wouldn't have even mentioned that she was coming. Tony knew that I was a bit of a player...actually, I was a rampant horn dog, I would sniff at the arse of any bitch that happened to walk past me and if she took the bait, I'd waste no time getting her into bed or, failing that, any private spot to shag her, even if it was standing up in the bus shelter in the middle of Kettering High Street.

"Erm, I still have links with the local adult education centre from when I was teaching business studies at night school, I could sort things out for the apprentice to get going on the training course!"

I'd been very careful not to mention 'Her' or 'She', keeping my offer gender neutral so that it didn't seem like I was trying to get my hands on the only female assistant if there was only one female that is.

There was a moment's silence from the new HR manager, "Well, I would be lying if I said that I had time on my hands to look into this, taking over from Mr Cooper at the last minute has left me with a massive amount of work to catch up on...if I'm honest with you I wouldn't have taken on an apprentice if it was my choice but Mr Cooper had already given her the position...so, if you're happy having a totally inexperienced assistant on a four day week and the extra work of managing her college course as well, I'll assign her to you!"

I thanked him and put the phone down...I didn't need to ask anything else, I knew that it was a girl, I knew that she was only sixteen years old and I knew that she would have no experience at all so I would have to teach her everything that she needed to know. I knew that it would be a lot of hard work but I also knew that as a sixteen year old girl, she could be fun to teach her a few facts of life...mind you, it had been a long time since I last fucked a girl that young and I knew that I would have to play my cards carefully.

I checked Simon's work computer, there was almost nothing on it, he had worked for me for just short of a year but there seemed to be little to do with work on his old PC, there was a massive search history on the web browser though, it looked like he spent more than four hours a day looking at stuff on the internet and as I was about to clear his history, I had an idea...when my new assistant started work, I would need to give her something to do to assess her computing skills, I could get her to search the computer's hard drive and clean out all of Simon's files that she found.

That little voice right at the back of my head popped up with, 'She won't have much to do, there are only three documents in the docks folder and no pictures in the picture folder at all...perhaps we should 'Salt the battle field' to give her something to look for and assess her reaction to what she finds!'

I had until next Wednesday to find a few 'Interesting' pictures to pop into Simon's picture folder, it would be a fag...well, a pain in the arse really but I had thousands of nude and rude pictures at home, I could reset the internal date on my computer at home back six months and scan a picture, then add a day onto the computer's internal date and scan another picture and so on until I'd made a collection of pictures suitable for my new assistant, whoever she was, to find under my loose supervision, just so that I could observe her reaction to pornography, from the very mildest, woman in a bra and knickers, woman in just knickers, naked man, man with a woman playing together, two women playing with each other, man and woman fucking and for the last picture, something special, I had a few pictures of women being covered by a rather large dog.

All of the pictures that I'd use were my own, not just belonging to me, actually taken by me on one of my thirty-five millimetre cameras and then developed and printed by me in my own dark room.

It took me several hours to pick out just the right pictures, make the changes on my computer to add the wrong date to the pictures that I'd scanned, I even found a few pictures from almost twenty years ago when I was a night school teacher in my free time, I ran a photography course and I got a hell of a lot of pussy from my female students after photographing them in compromising positions. I even found a bunch of my favourite hard core pornographic stories to add in to the mix

I popped the thirty pictures onto an old memory stick along with the pornographic stories and took them into work on Monday morning. Downloaded them into Simon's now unused computer and then formatted the memory stick to get rid of any evidence...I even wiped my finger prints off of the memory stick before dropping it into the top left hand draw of Simon's old desk.

On Wednesday, I found a schoolgirl sitting outside my office when I arrived for work, I unlocked my office door and then gave her a second look, 'fourteen...she can't be a day over fourteen years old!' popped into my head.

"Can I help you Miss?"

She jumped to her feet, I fought back a smile because she was so short she made me have a very inappropriate thought...'She's so short she could almost give me a blow-job without even bending over!'

"My name is Dawn Clarke and I'm looking for Mr Preston of the Future Contracts Department."

"Well Miss Clarke, you've found him, how did you manage to find my office in this rabbit warren of passageways, there isn't anyone in work yet to ask the way and there are no names on the doors!"

"My grandfather drew a floor plan of the building for me when I told him which office I'd be working in, he's been here several times in the past!"

"Your grandfather must have worked here sometime in the past if he could draw you a plan from memory...well, I'm glad that you're here so early, I can show you where the kitchen is and where my coffee and tea things are."

As we walked to the kitchen area, a small room with the usual sink, cupboards, hot water boiler, not just a kettle, at tea break time we'd need gallons of hot water ready and waiting for us. I pointed out the three tables with their twelve seats and also pointed out that there were around sixty people working in the building and only space for twelve people to eat their lunch. I told Dawn how I liked my coffee at morning break and my tea at afternoon break, because I was a department head, I had a metal locker in the kitchen to keep my stuff in but the milk was kept in the fridge, each manager was responsible for bringing in milk and if she spotted that the milk looked like it was about to run out, she had to tell the manager on that weeks milk roster.

As we walked back to my office I asked her who her grandfather was, "I've worked for the company for close to twenty years so I probably know him if he worked here recently!"

"No, he's never worked here but he comes here when he needs lifting equipment at Glebe Farm!"

I snapped my fingers, "He's not Ron Clarke from Glebe Commercial is he?"

Dawn nodded her head.

I smiled, I'd known her grandfather for a very long time, in the days before the internet came around, Ron was one of the main customers for my home produced pornography so he knew my tastes very well, when the wife of one of his son's wanted to do a few night school courses, he sent her to my school to take my photography course and I actually got her to pose for me in all kinds of disgusting photo sessions. I started to worry that I may have used Ron's daughter-in-law in some of the photographs that I'd popped onto Simon's computer to watch Dawn's reaction to pornography, that worrying thought caused me to need to clear my throat, "Did your grandfather mention me...at all?"

Dawn shook her head, "When I went to my grandfather's house all the family were there so he just drew me the floor plan and told me to have fun at work today."

We were approaching my office when the thought popped into my head, 'If Dawn does recognise one of her relatives in the pornographic pictures...her reaction to seeing the picture will speak volumes as to Dawn's character!'

I opened my door and pointed to Simon's old desk, "My previous assistant's name was Simon, that was his desk, it's yours now, go through the drawers, if there's anything that you think might belong to Simon, you can box it up and mail it out to him and once you've sorted out your drawers, you can start on the computer files, there shouldn't be any personal files on the internal hard drive but you'll need to check it and delete anything that shouldn't be there!"

I watched as Dawn took her jacket off and hung it over the back of her chair, I grew a smile on my face as well as an erection in my pants when I saw how thin her dress was and the fact that I could see a faint glimpse of her bra and knickers through the thin material, they looked white but with flowers either printed on them or embroidered in them.

I was very distracted as I went through my morning post, checking through requests for new contracts or requests for variations to existing contracts. Usually, I'd write a little note on the back of the letter and pass it over to my assistant to type out a reply and once typed, I'd read through it and then I'd sign my name on the bottom of the page. Often, I'd have to correct the response because Simon often screwed things up.

As dawn was clearing out Simon's stuff from her drawers, I started to type my own responses to the contract requests, not that there was a lot of typing to do, I had several pre-written answers, usually I'd write in my notes, 'P2', 'P1', 'P5' and any little additional items to a standard paragraph and any salutation that I wanted to add so it just took a few seconds to write each answer.

I watched Dawn place a few items in a small cardboard box and she stuck a label on it with Simons name and address on it.

"Does your grandfather's floor plan show where the post room is Miss Clarke?"

She looked on her sheet of paper, "Over here, next to the loading bay?"

"That's right, drop your parcel off at the post room and come back by the kitchen, make us both a coffee each and we'll have two biscuits each as well as a treat."

I finished my day's post, I'd written and printed all the letters and was reading through just to make sure that every thing was okay when Dawn came back with a tray with our coffee and biscuits, "Do you know Sid Paxman?" she asked.

"I do...why?"

"He stole two of your biscuits, he said that you wouldn't mind, that you often shared your things with each other!"

"Well, he's the Managing Director's brother so I don't mind him having a few of my biscuits...did he say anything else?"

Dawn laughed, "He asked me what time my bus home left the station tonight and because it leaves town at six o'clock and six thirty, he offered me a lift home in his car tonight to save me a thirty minute wait in the cold."

'Crafty bastard!' jumped into my head. He could have told her to have a word with me, we were quite flexible, if any member of staff needed to leave work at a quarter to six to catch their bus, we would allow them to take a reduced lunch break to allow them to leave early for public transport.

We just chatted in general as we drank coffee and ate biscuits, I asked Dawn what she had planned for her lunch, "I've brought a sandwich and an apple for my lunch, I was planning to eat it at my desk or in the kitchen if there's room in there."

"Eating lunch at our desk is frowned on but if the kitchen is full, there are benches on the park behind the office and more down by the river if it is dry outside and if it is raining you could go into the shopping centre and eat on the concourse."

After tea break, I set Dawn the task of making sure that all of Simon's private files were erased from her computer, "Start on the documents folder, there shouldn't be any work related files but just read them in case there are any contracts files in there and then go on to the pictures folder."

I'd already seen what files Simon had been holding in the hard drives documents folder and knew that there were no problems, just a few dirty stories that I'd put in it a few days earlier.

I watched as Dawn's hand flashed around the mouse pad controlling the cursor on the screen through the mouse, "There are three documents in the main folder, quite old, should I check the files to see if the letters have been sent out to the customers?"

"That sounds like a good idea, we file the newest files to the front of the customer's folder in the filing cabinet."

Dawn checked that the tree letters had hard copied in the reliving folders in our filing cabinet and once she was happy, she deleted the files off of her computer and then she said, "There's a sub folder called private and confidential...is it okay for me to look in it?"

"Yes, it is okay, Simon knew that he wasn't supposed to store any personal files on his work computer and he had a week after he handed in his notice to sort out any personal files...it could even be just an empty folder if he deleted his private files."

I was watching Dawn closely, a little smile curled her lips up a little, I said, "Was the folder empty?"

"No, there were four documents in it, this one is called dogging, it's been downloaded from Alt Sex Stories Text Repository written by someone called Rose Eastmann!"

Now that was a surprise, the file had the site's name on the top of it but I knew that it was just listed as 'ASSTR.Org' not its full name so Dawn obviously knew the site to translate the initials into its full name, "Dogging, what's that about, Crufft''s championships?"

Dawn gave me a pitying look as if she was saying 'Old people!' in her head, "No, it's where a couple go into a car park or someplace like that to have sex while other people watch them!"

I could see that Dawn's eyes were quickly flashing back and forth across her screen as she quickly read the story on her screen, "You can't be serious...is it an American thing?"

"No, there's a well known place quite close to here, you know the public toilet car park at Rush Copse in Salcey Wood?"

I played dumb and shook my head, "I don't think I've ever been in Salcey Wood."

"Well, they do it there regularly!"

"What, at night after a trip to the pub kind of thing?"

Dawn was still reading as she shook her head, "No, they close the toilet and car park at dusk so it all goes on during the day!"

"Probably better delete those files if they are pornographic!"

Dawn looked a little disappointed, "Can I email them to myself so that I can read them at home later...I could get them off of asstr.org myself but their search facility doesn't work very well and it could take hours to find the story!"

"If you have a web based email account you can but you can't use the company email account, every email is checked by IT before it goes out, the incoming ones are checked as well."

I spotted the screen turn darker as Dawn switched from the Microsoft Word screen to a web browser, a few seconds later, she had opened her email account to send herself the stories, I walked up behind her and placed a slip of paper with my personal email address on her desk, "Can you copy me in on the email so I can read about dogging when I get home please?"

I didn't really need her to send the files to me as I already had them on my computer at home but having her send me an email would give me her email address as well as put my email address into her contacts list so that when I sent her an email, her computer wouldn't throw my email into the trash bin.

I was still behind her when she opened the pictures folder, the first picture was the woman wearing a very sexy lingerie set, bra, knickers and stockings with matching suspender belt. I leaned over her shoulder, "It looks like Simon was a naughty boy!"

Dawn clicked on the right arrow to see the next picture, same woman, similar pose but she was topless this time, Dawn clicked the right arrow again. She clicked through the pictures quite quickly, I pretended to be busy behind her while she was looking through the pictures. When the picture of the woman with the dog filled the screen, she paused on that picture longer, "You know what...this could be my mother in this picture, she used to have shoulder length ginger hair like the woman in this picture before I was born and she had a skin blemish that's very similar to this woman but my mother's blemish is on the side of her left breast, not her right.

I pretended to turn at that point and I looked over Dawn's shoulder, there wasn't a hint of a blush on her face as she studied the picture of her mother being fucked by a Great Dane while her mother was sucking my cock, fortunately I'd cut my head out of the picture so that she wouldn't recognise me, "Oh my, that's quite...well, very strong, I think you'd better delete those pictures as soon as possible Dawn!"

I'd have to check my records when I got home, see what date I actually screwed Dawn's mother, the woman in the picture was definitely her mother but when I scanned that picture, I'd been standing on the left of the picture and the dog mounting Victoria was on the right of the frame, I'd flipped the picture in photo editor to put myself on the right just because people expect to see sinister things on the left and I wanted the massive dog to look sinister and not me....it was a really good thing that I'd cut my head off in the picture. Vicky's face was obscured because Vicky's face was in my crotch as she sucked my cock deep into her throat.

At lunch time I told Dawn that she was entitled to an hour off for lunch but if she wanted, she could take forty-five minutes break and leave work fifteen minutes early to make sure that she could catch her bus.

"I don't need to leave early because Mr Paxman is giving me a lift home, he's a friend of my mother's, he's going to pop in and have a coffee with her on his way home!"

That caused me to smile, of course Sid Paxman knew her mother, after I was finished with her, I passed her on to Sid for her to be his sex toy until he passed her on to someone else.

After lunch, I taught Dawn about contract reminders, I'd written a program that interrogated the contracts database and output a CSV file with all of the relevant details to form reminder letters and how to run that CSV file through the word processor 'Mail Merge' program to create the letters automatically to send out to our customers to remind them to renew their contracts, today's print run was one hundred letters...it took Dawn until six o'clock to print the letters, fold and stuff them into envelopes, she dropped them off at the postal department on her way to Sid Paxman's car.

I was already in the car park in my own car, I was in no hurry to get home so I slipped in behind Sid's car as he left the car park, I followed him out towards the 'A508' southbound, there was a slow crawl of rush-hour traffic so it was easy to keep two cars between me and Sid all the way to Wooldale Road, it was more difficult to keep out of Sid's rear view mirror but I stuck to his tail roughly five hundred yards behind him.

We took the third tuen off of the roundabout and into Quinton Road but Quinton Road didn't last long, as we crossed the bridge over the stream, the road turned into Wooton Road and after about five miles, there was a signpost for a car park and a public toilet ahead of us on the left hand side of the road, Sid started to slow and he indicated to the left so I had to slow down even more to stop myself getting too close to him.

Sid turned into the car park and drove all the way through the car park to the end spot, I followed but stopped in the first parking space, the space closest to the public toilet. I dumped my car unceremoniously and ran through the footpaths parallel to the car park to the space that Sid had pulled into.

I wasn't alone in the bushes though, another man was ahead of me watching Sid and Dawn in the parked car.

It had taken me so long to run from my car to the other end of the car park that Dawn and Sid were already in the back seat of his car, the front seats pushed out of the way to give them more room in the back of the car. They were kissing and Sid was unbuttoning the front of Dawn's dress, opening it like a coat, exposing her pretty bra and knickers.

I watched as Dawn wriggled her arms out of the sleeves of her dress and then she turned and got onto her knees on the seat, her bum against the window of the back door as she bent over to suck Sid's cock. As she sucked him, Sid pulled her knickers down and without taking her mouth off of his cock, she rocked from one knee to the other and her knickers sailed over into the front of his car, her bra following soon after.

Once Sid had Dawn totally naked, he leaned past her bottom and wound the window down in the door behind her and the man who had beaten me to the bushes stepped up to the door and started fondling Dawn's bum and reaching around her to play with her tits as she sucked Sid's cock.

I saw the peeping Tom pull the front of his trousers down and he started pulling Dawn towards him so that he could fuck her through the open window but she shook him off and jumped into a seated position on top of Sid's cock and while Sid fucked her, she leaned over and started to suck the cock now sticking through the open window.

A whistle was being blown by the toilet block, the ranger telling people that the car park and toilet block were about to close, I started walking back to my car and mused on how much fun it was going to be having Dawn work for me for the next three years while she trained to be an apprentice clerical assistant.

When I got home I went through my files, Ron sent his daughter-in-law to my photography class at the start of the twenty-zero-five and I started to have sex with her the following year, the thought hit me that Vicky had told me that she and her husband didn't have sex very often while I fucked her at least twice a week for two years so I had more chance of being Dawn's father than Ron's son John did...it was certainly going to be an interesting few years, now what I really needed to do was find a way to get a DNA test done on Dawn and myself, just to be sure and if it turned out that I was her father, I'd fuck the arse off of her for as long as I possibly could.

4,587 Words.

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