Diary of a prison officer : Part 1

(Part 1 from 5. Fiction.)

*** All characters contained within are entirely fictional; any similarity to any real or fictional person living or deceased is totally unintentional. Do not read this story if you do not enjoy reading about consensual sexual activities of an exhibitionist nature. Otherwise read on......


Dear diary, this feels very strange indeed! I haven’t written a diary entry since I was fifteen; when filled with angst against the world in general and in particular that I was unable to lose my virginity no matter how hard I tried. I would fill page after page with my rantings. So here I am now some thirty years later making another go of it.... why? I hear you ask. Long story, let’s just say that after spending twenty years in the army and a failed marriage behind me I think it’s time to get my head together and climb out of the doldrums I have been wallowing in for the last eighteen months and this seems as good a place as any to start. So thank you diary, although you say nothing back to me you are going to help me put my thoughts down on paper and let me see the world as it really is, for a change.


I have decided the first part of my recovery plan is getting myself a job. Yes I know, financially, I don’t need to work full time thanks to my army pension and divorce settlement but a man needs to feel fulfilled and bouncing around these four walls and going down the pub is doing me no good at all. So I went down to the newsagent this morning and picked up last week’s local paper to see what jobs were available that might be suitable for me and of interest. Initially I couldn’t see anything at all, but then over a second cup of coffee it caught my eye. There tucked away in the corner was the strangest sounding advert I have ever seen, naturally it piqued my interest and I couldn’t resist giving the number a call. This is what the advert said, what do you make of it?

“Are you fit and of sound mind? Do you believe in tough love? Do you agree that everyone deserves a second chance but if they refuse to reform they should be punished? Are you available to start immediately? If so, why not start a new career with the prison service. Give us a call on 0800 012 3456 and ask for an application pack”

When I called the number I got an automated message asking me to leave my name, address and to list five attributes I consider the most important to me. Mmm, this was unexpected – five attributes, did they mean mental, vocational, physical or all of them? So I hung up, left it a few minutes before calling back and this is the message I left for them.

“Hi my name is Samuel Telby and my address is Flat 135, Berghouse Court, London, EC1V 4XA. My five most important attributes are: Fairness, Loyalty, Fitness, Open-mindedness and Stamina. I would be very grateful if you would send me the application pack as the job advertised sounds very interesting and I would like to learn more about it. Thank you.”

There, that’s it all done, on to the next job application; well it will be next week as there aren’t any other jobs that are any good. By for now diary, it’s the end of a mentally exhausting day and I’m just about beat, so it’s shower and bed for me. Night night.


The application pack has arrived through the post. All I can say, it seems the ideal job for me. I’m just worried it’s going to be too good to be true. I spent most of this morning reading and rereading the information booklet and job specification, then this afternoon I took my time and completed the application form with great care. I then raced down to my local post office to return it by recorded delivery.

In brief, this is what it’s all about:

HMP Ollerton is a failing prison and is in urgent need of modernisation and change in focus. The prison service is seeking a complete change of staff under the guidance of the new Prison Governor Liam Havers. He requires from his staff total trust and loyalty, ability to withstand the pressures associated with policing dangerous and difficult male prisoners, willingness to undergo professional and on the job training. In return a generous salary and benefits package is provided for the right candidates.

So diary, what do you reckon? Too good to be true? All I hope is that it is genuine because it’s right up my street and something I can sink my teeth into. At last I will have a job that I can utilise all my discipline and combat experience to a positive effect. I will just have to keep my fingers crossed and hope to hear from them.


Dear diary, major peed off that’s how I’m feeling right now. Still no news about this prison job but at least there’s been another job in the paper which may be promising, a Physical Education Officer at the local college. Only trouble is its part time, three days per week though with reasonable salary. I decided to go out tonight and hitch up with my long time friends Tom and Mike down at the Kings Head. I’ve known Tom since I was a kid and I met Mike through my ex-wife, we remained friends even after our divorce. I chatted about the two jobs and discussed the merits of each with them. It wasn’t a great surprise for me when they gave the thumbs down for the prison job but it was a big thumbs up for the college job. Their logic being that working in a college with nubile young females would be vastly preferable to working with pent up volatile male prisoners. I could see their point, when thinking with your dick, but thinking long term from the vocational perspective it would not be as satisfying. Tom changed the conversation slightly by bringing up the subject of his eldest son, Aaron, now 23 years old (crikey I remember taking a telephone call from Tom, proud as punch when Chrissie gave birth to him at home). Last week he’d told Tom, out of the blue, that he and his girlfriend were going to get married as she’d fallen pregnant and he wanted to do the decent thing. Naturally they were both shocked but pleased that he was doing the decent thing and now the wedding organising machinery had kicked into action. Aaron has been busy planning for his stag do and asked Tom to join him, mainly so that he could act as the responsible one to make sure everything ran smoothly and didn’t get too extreme. For Tom this is a double edged sword, yes it’s a sensible idea but he’s going to feel like a granddad surrounded by Aaron and his young friends. As he was recounting this to us Mike and I reached the same conclusion simultaneously and announced in unison, to our amusement, why don’t we join you and keep the old codger company? He was relieved with this idea and I have a sneaky feeling that he was hoping we would say that. He didn’t have precise details about the date or the venue but would give us a call once he had any more info. Over the next couple of pints we took a trip down memory lane, recounting all the escapades we had got up to..... It was a laugh but god, how old do I feel now thinking about the years that have flown by! After parting company with the guys I called into the local chippy and treated myself to a large back of chips and a battered sausage, I was starving.


Tom called; he says the wedding is going to be Saturday 6th March 2010 at 2.30pm at the St. Edmunds Church on Station Road. The stag do is going to be on Saturday 27th February 2010 starting at 8.00pm and going on till late. It will start off with a sit down meal at the local Indian restaurant before moving onto the Sundown Nightclub where a function room is going to be hired and a female double act are going to entertain the some fifty guests (I didn’t dare ask what the entertainment theme would be!). It sounded really good and I told him so, yes, he agreed Aaron has certainly swung into action now, it’s a shame he left it so late to tell us as it leaves little time to arrange things what with the baby due to be born at the beginning of April, never mind, life is never neat is it Sam he asked? Aah, that explains the closeness of the wedding date. We chatted for a bit longer before arranging to meet down at the Kings Head again next Friday, timetables permitting.


Dear diary, I’m as happy as a sand boy and the postman is once again on my Christmas card list. It finally arrived in this morning’s post, an official looking envelope marked “HMP Services”, with fingers shaking I carefully opened the envelope to reveal a single sheet of paper with three lines of writing on it and this is what it said:

“Dear Mr Telby,

We have received your application and can confirm that an interview has been arranged for you on Monday 8th February 2010 at 9.00am. Please bring with you your passport, driving licence and two proofs of address. You will be required to undergo a physical fitness test and medical examination so shorts should be brought with you.

We look forward to meeting.

Yours sincerely,
PG Liam Havers”

I literally danced for joy around my living room, I picked up the telephone to spread the good news but then remembered the reaction I had received previously and in any case I didn’t want to jinx my chances of getting this job, so I put the phone down again with a rueful smile. Shit! I thought to myself, what am I going to wear to the interview? All my suits have definitely seen better days and my shorts are a little worn. Tomorrow I will go into town and buy myself a new suit and sports shorts – and a pair of shoes that aren’t scuffed to hell......


I didn’t know clothes shopping could be so tiring. I’ve spent nearly all day going from department store to department store, bespoke tailors to bespoke tailors searching out the ideal suit at a reasonable price for me. Finally I made up my mind which one I liked the best and bought it, and then it was on to the shoes, then the shorts. It was all so expensive! Hopefully it will all be in a good cause if it helps swing the job for me, plus it’s been a long time since I devoted a whole day to retail therapy and paying attention to my appearance.

Looking in the mirror, I can see the tell tell signs of a forty five year old man; the ever deepening wrinkles around the eyes and across the forehead, the white hairs flecking my close cropped beard and showing up in ever increasing numbers on my head. My green eyes still twinkle but have that worldly air about them which only comes from a lifetime of experiences, some good some bad. I don’t think I’ve ever been described as handsome but I must be fairly pleasing to the eye because I’ve had my fair share of lovers (and wife) none of whom have ever called me ugly, but for me my best attribute must be my body. Ever since being in the army I have had a well toned body, not overly muscular but defined enough to draw glances when I wear just my shorts while jogging round the park or in the swimming pool. I’d be lying if I said I didn’t enjoy the attention but I’m not so egotistical to believe that I’m the best thing since sliced bread and the ground that I walk on should be worshipped!

On Friday I shall go and get my hair clipped short again which will make me look the part for a prison officer (not jumping the gun here am I?)


Dear Diary, nothing much to tell you to be honest, have been loafing around as usual. Gave the flat a spring clean, it’s a task I’ve been conveniently overlooking for too long and boy did it need it! Four bags of rubbish, three dirty dusters and half a can of polish later and the place was looking good as new. This has helped motivate me to get back into the fitness regime of jogging in the evening and going swimming in the morning starting from tomorrow..... but first a pint while Eastenders is on. After all I will want to be as fit as I look.


Oh boy, am I like a cat on a hot tin roof! I have sorted out my outfit for tomorrow twice so far, ironed everything and polished my shoes and now I am pacing around like a caged lion. I would go out for a change of scenery but it’s raining heavily and I’ve already been out for my jog round the park. I’ve been very good I have done my daily run every day since Thursday and been swimming twice. I have even cut out the beer, how dedicated is that? It’s going to be a long day tomorrow so I’m going to have an early night and try to get some sleep, over and out.


Oh diary where do I begin? I know I said yesterday that today was going to be a long day, I just didn’t know just how long it was going to be and what I was going to be put through. I’m glad I didn’t know in advance otherwise I think I might have changed my mind there and then. Sorry, I’m jumping the gun and racing ahead. I will start again at the beginning.....

My alarm clock buzzes, my brain wakes slowly but my body jumps to attention. I’m sitting upright by the time my eyes are fully open. Something doesn’t feel quite right. It takes a minute to register, I’m naked, and my T-Shirt I wear to bed is lying crumpled on the floor. I must have been hot in the night. Shrugging my shoulders I pick it up, fold it and place it on my pillow for later. I saunter to the shower, wash and have a shave before drying myself and going to the kitchen (still naked) to make myself some breakfast. Two coffees and a bowl of muesli later I feel human at last, checking the clock I see it’s time to get ready. So I get dressed and spend the next half hour perfecting my attire and appearance. Last job of the morning is to pack my bag with the necessary documents and the all important shorts.

Having studied the London A-Z I’d planned my route carefully but I had forgotten just how slow and irritating the rush hour traffic can be, nevertheless with nerves still intact and not too hot under the collar I arrived at the imposing front gates of HMP Ollerton Northern entrance. As I stopped the car at the barriers an armed guard walked up to my car indicating that I should wind down the window and produce identification. Trying to disguise my nervousness I handed him my letter from the Liam Havers, he quickly scanned the contents, looked me straight in the eye and said “Welcome on board Mr Telby” with a quirky grin. I replied that I was only at the initial interview stage and that his congratulations were a little premature. “Sure” was his only response before walking back to his station and pressing the release button allowing the barrier to rise and let me inside the prison car park. There were few parking spaces available considering its size but eventually I found a spot and pulled in. Finding the main entrance was a doddle, the prison walls were over thirty feet high and with only one small door the choices were limited. I went to bang on the door when I noticed a push button the right, duh! Who would have heard me knocking anyway? Pressing the button firmly I just hoped it was ringing somewhere because I couldn’t hear anything. Almost immediately I heard a whirring noise, turning my head in its direction I saw a CCTV camera pointing at me. I showed my letter to the camera which seemed to do the job as the door clicked open after a short delay and silently opened. Stepping inside I was greeted by the sight of a plain reception room with a large table facing me, with a sheet of paper upon it, a chair adjacent to the table with an empty box on the seat, in one corner was another metal door, in another corner was a large scanning device (just like you get in the airports) and the ever present CCTV camera watching me. Walking over to the table I could see that the sheet of paper was actually a set of instructions which read as follows:

“All job applicants are to read and follow the instructions exactly. Failure to do so will constitute a refusal and jeopardise your application. There is a purpose to each requirement, do not question them; they are also a test of your trust in your potential employer and the establishment.

1. Step up to the CCTV camera and announce your name, address and purpose for being here.
2. Return to the table, empty the contents of your pockets and place them on the table. If you have a bag, empty its contents also onto the table.
3. Remove all of your clothing until naked, fold them neatly and place them on the chair in the box provided. They will be returned to you after your interview.
4. Walk over to the CCTV camera, reconfirm your name before holding your arms out to horizontally from your sides turn slowly until facing away from the camera.
5. Spread your feet until they are two feet apart, place your hands on your buttocks and bend at the waist as far as is comfortable. Pull your cheeks apart.
6. When you hear a buzzer, stand up and walk slowly through the scanner before returning to the table.
7. You are permitted to wear the shorts you have brought with you but no other article of clothing is permitted. Personal possessions are not to be brought with you.
8. When you have completed these tasks knock on the door and you will be escorted to the interview room.”

I think it’s fair to say that I was surprised by the instructions and I read them twice over to make sure that my eyes weren’t deceiving me, but no, they were there in black and white. Whatever my personal thoughts on the matter were irrelevant and if I wanted to progress with my application compliance was necessary. So I walked over to the camera proceeded to give my name and address and a short speech about my aspirations of becoming a prison officer and how pleased I was to be given this opportunity.

Then returning to the table I emptied all of my pockets and the bag I had with me placing the items neatly on the table. Then with my back to the camera I removed my shoes placing them in the empty box; then my socks, rolling them up and putting them in my shoes; unbuckled my trousers then carefully stepped out of them before folding them and placing on top of the shoes; my jacket followed, then my tie and shirt leaving me standing in my pants. With a momentary pause I quickly pulled them down, added them to my other clothes, then turned round and walked back to the camera. Feeling a little foolish I restated my name before lifting my arms up and doing a slow pirouette so that I was facing away from the camera. Spreading my legs I dropped my arms and reached behind me lightly holding my cheeks. Bending over at the waist I felt my face flush, I’m not sure if it was from the position or the embarrassment of doing a moony to whoever was behind the camera. When I pulled my cheeks apart I felt cold air blow over my anus making it quiver and to my surprise my cock filled a little in response. I seemed to hold that position for an eternity as the camera zoomed in and out judging by the sound of the whirring noise behind me. Finally the buzzer sounded and I released my cheeks, stood upright stretching my back as I did so. As casually as possible I sauntered over to the scanner, stepped through it and quickly returned to the table where I retrieved my shorts. I was relieved to feel the material slide up my legs and the waistband fit snugly against my flesh. The one fly in the ointment was due to my semi-flaccid cock being of a decent size it flopped around quite noticeably within my shorts as I strode up to the door and knocked three times.

The door opened to reveal a uniformed prison officer, in his fifties who introduced himself as Archie after shaking my hand. He asked me to follow him (not much choice there!) down a long corridor, this judging by the signs on the doors lining the corridor was the administrative part of the prison, at the very end was a door signed “Interviews” and it was through this door I was shown. The door closed behind me, in front of me was a long table behind which sat three men, again in their fifties all in prison uniform reading their paperwork. At the sound of my entrance they slowly lifted their eyes and smiled in unison.

“Ah, Mr Telby, it’s good to see you” said the man in the middle. “Let me introduce myself and my colleagues. I am Liam Havers, the prison governor and the gentleman to my right is my twin brother Max, and to my left, my youngest brother Adrian.”

My surprise must have been evident on my face because all three burst out laughing and Liam started to speak again.

“An unusual situation I know, but it is all above board I can assure you. My brothers and I have been involved with the prison services all our lives and when the opportunity arose to reform this failing prison it was one we couldn’t resist. We have mortgaged ourselves up to the hilt to purchase this prison from the Government, it is the first venture of its kind and they are monitoring our progress closely. We will receive generous funding if we can restore law and order within these walls, reduce the rate of reoffending when the prisoners are released and eliminate the physical abuse between the prisoners. How this is achieved is our business. Unfortunately many of the existing prison staff are as corrupt as the prisoners and will be replaced as quickly as possible. We are adopting a fast track employment system so providing you pass this interview, the medical and the physical fitness tests today we will be looking to start your training and employment with us on Monday 1st March 2010. There are twenty prison officer positions to be filled and thirty applicants we will be interviewing today and throughout this week, so I don’t need to point out that competition is fierce and the slightest mistake on your part will affect your prospects.”

I gulped silently to myself, I didn’t realise how sought after this job was, mind you the wages and benefits were generous so I shouldn’t have been that surprised especially with the recent downturn in the economy etc. Doing my best to retain a confident manner I agreed that the position must be very attractive to a lot of people who want to do this type of job.

“Indeed.” Liam replied. “We are however looking for a certain type of person with the right experience, capabilities as well as attitude. This we saw in your application a great deal, however when it came to the first of the practical tests this morning we were a little disappointed in how you responded. We are looking for a 100% pass rate at this stage yet you only managed to score 85%. Would you like to know where you lost those percentage points and if you wish to, how they can be regained so that you pass that test?”

With genuine confusion in my voice I said “I am really sorry to hear that, I thought I had followed the instructions closely and did everything required of me. Yes I would very much like to know where I went wrong so that I can correct this situation as I want this job and don’t want any avoidable issues to stand in the way.”

“Excellent response! You’re correct in that you followed the instructions, yet we felt there was some reluctance on your part. This was demonstrated by the way you turned your back to the camera when undressing; you hesitated before pulling down your underpants and rushed to put your shorts on. We must have confidence when giving you instructions that you will follow them to the letter and you will not question them. Unfortunately with the type of prisoners we have in here, the slightest chink in our armour will enable them to break through and risk the success of our endeavour. I am going to ask you to remove your shorts, fold them neatly, hand them to me and then sit back down in your seat. Please do so now.”
Knowing what was at stake, I didn’t hesitate for a second. I stood straight up, pulled my shorts down, stepped out of them before folding them neatly and placing them in Liam’s outstretched hands. I then sat back down in my seat, trying to act as normal as possible in the circumstances and ignoring the fact that my cock was now semi-hard and I was the only naked person in the room!

It was very surreal, the rest of the interview carried on as if there hadn’t been an interruption, the questions were what I expected and I had little difficulty answering them. Then there was a knock on the door and a young Asian man walked in, from his uniform he was obviously an inmate, pushing a tea trolley. As he walked past me he did a double take at the sight of my naked body, but said nothing, merely bowing slightly as he left the room. I had little time to react, probably just as well considering how quickly I had dropped points in my first test. Just as the conversation was drawing to a close and I had finished my cup of coffee, Liam pushed a hidden button and a couple of minutes later there was a knock on the door.

“Come in!” was all the Liam said.

In walked two men, one in a white coat, the other dressed as a physiotherapist. I guessed my next two tests were about to begin. The guy in the white coat was introduced as Richard (the prison ) and James (sports coach). Liam smiled warmly at me, informing me that I had not only had I passed the interview but I had also regained the lost points from the first test. He then went on to say that I would first have a medical assessment with Richard, followed by the fitness test with James then a final short after exercise check-up again with Richard. If all tests were successfully passed then I would be invited back into the office for the return of my clothing and signing of the contract. Standing up I walked over to the table and shook all three interviewer’s hands before turning to follow Richard and James out of the room.

“Mr Telby, have you forgotten something?” Liam called after me with a chuckle.

I turned round at the sound of his voice looking in his direction I saw him pointing to my shorts still folded neatly on the table in front of him.

“No Sir, I didn’t forget about them. I simply assumed that you would tell me when I could have them back and didn’t give them another thought. Is it okay to put them back on again?”

“Mr Telby, you are growing in my estimation and I think you will be a valuable asset to the team. With that ‘can do’ attitude you will go far. Yes you may don your shorts again.”

Slightly embarrassed to have five pairs of eyes focused on me I was more than happy to pull my shorts up, and thanking them once again followed Richard to the medical centre. As I followed him up the stairs I guessed he must be in his late 60’s or early 70’s, presumably this job was to top up his pension. Richard made small talk as we entered his office/consulting room.

As I sat in the chair opposite him I felt more at home having had more medical check-ups than I care to remember while in the army and had a pretty good idea on what would follow. Sure enough Richard pulled out a three page document from his drawer and started filling in the standard information i.e. name, address, family medical history & personal medical history. Then he took my blood pressure, general stats, weight, lung capacity and temperature. Still sitting in his chair but leaning forward he asked me to stand in front of him and to remove my shorts. I followed his request and naked once again I calmly watched him gently roll my balls feeling for any unexpected lumps before turning his attention to my cock. He pulled the foreskin back and examined it closely for any abnormalities, so close in fact that I could feel his breath on my sensitive head. It pulsed and expanded in response until it was fully erect at just over eight inches long. Richard seemed very pleased with this result and commented on its healthy appearance and functionality. Not knowing quite how to respond I simply said that I had no complaints with it, he laughed and said he didn’t think I would or anyone else would for that matter! He turned in his chair; opening a drawer he retrieved a pair of latex gloves and a tube of KY. Uh oh, I know what they’re for I thought to myself.

“Please turn round, bend over at the waist and pull your cheeks apart.” Richard said in a neutral voice.

As I pulled my cheeks apart I heard the snapping of the gloves being put on and then felt the cold gel being applied to my anus. His finger felt large to me and my ring tightened in response as it smeared the gel around my ring.
“Relax please otherwise you will experience some discomfort.”

I did my best to relax, taking deep breaths as I felt pressure being applied. Eventually the finger pushed in up to the first knuckle.

“Mr Telby, you really must learn to relax. From your tightness I can tell you are not used to having objects inserted up your anus, I am not going to hurt you, now please try harder.”

“Yes Sir, you are quite correct I am not used to having things up my arse! My wife used to try to push a finger up me but I didn’t like it. I am trying to relax honestly but this position is uncomfortable for me.”

“Mmm, let me think.” Richard said deep in thought gently pulling his knuckle out. “Okay, hop up onto the couch, lie on your back and pull your knees up to your chest.”

Open to any suggestions to move this situation on, I did as I was bid. To be honest it was a new position to me but somewhat reminiscent of the missionary position! I said as much to Richard who smiled in response but said nothing, instead he picked up the tube of KY and stepped up to my exposed anus and slowly squirted a liberal amount onto my hole. It momentarily clenched at the cold jolt but slowly opened again as the gel warmed up. Richard looked down at me and started to ask me about my life in the army and seemed genuinely interested in the answers I gave. I give him credit for his distraction method worked a treat, I barely registered his finger’s entry into me until I felt his knuckles brush my crack and his finger tip was pushing against my prostate sending throbbing pulses into my cock. I looked up at Richard and grinned saying

“Well doctor you seemed to have reached the spot!”

“Indeed I have, well done. You have a perfectly healthy prostate and rectum. I often find this position is successful for those tighter than average rings, and yours has got to be about the tightest I have come across for many a year.”

“Really, I am surprised.” I replied quite genuinely. “I would have thought most of the men in this prison would be in the same position as me.”

“Oh you’d be surprised.”

With that he withdrew his finger, wiped it clean on a tissue and announced that the medical was over until the post fitness test. As I pulled on my shorts again I saw the figure of James standing in the doorway casually watching me or rather my crutch as it bobbed around behind the fabric as I stood up again. Richard told James that he would join us in the gymnasium shortly to carry out the tests. James nodded an acknowledgement.

“Are you ready Mr. Telby?” James asked. “If so, we’ll start your fitness assessment in the gymnasium downstairs, please follow me.”

Not waiting for a reply he marched briskly along the corridor, down the stairs and back along the main corridor, almost to the main entrance then through a side door into what had to be the best equipped gymnasium I had seen in a long time, it even had three frosted glass shower cubicles at the far end. For the next hour I used every piece of equipment with James watching intently and writing endless notes on my progress. By the time I had completed the last test I was hot and exhausted, sweat was pouring down my face and pleased to be taking a breather.

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