Diary of a prison officer : Part 2

“In a word no, for several reasons; firstly, it wouldn’t be ethical on a professional front. You came to me asking for advice and guidance, which I have given as your prison officer. To go along with your suggestion would cross the professional boundary and potentially cause both of us problems by blurring the basis of our relationship. Secondly, on a personal front, and this is to remain just between the two of us. I’ve only ever been fucked up the arse once and that was in the line of duty, so to speak.” I replied a little gruffly.

“Sorry Sir, I didn’t mean to speak out of turn, you don’t have to give me an explanation after all I’m the inmate and you’re the officer.” Jarek said suddenly all petulant.

“Look there’s no need to be like that. Personally I like you, but I think it’s best to keep things simple and I am just being honest with you as I have always been throughout our interactions. Right back to business, now you know the reason for your hole’s condition did you want to tighten it up or leave it be?” I asked.

“I think I’ll leave it be for the time being if you don’t mind, I can see that there may be some advantages to being able to accommodate large objects, at least I won’t have to fear advances from any of the larger endowed prisoners!” he said with a chuckle before adding “Oh, and by the way it doesn’t change how I feel about Marita you know.”

“Of course not, now if that’s everything I think it’s time we got you back to your cell before they think you’ve done a runner.”

With that I escorted him back to E-Wing and went for lunch, I was famished as well as parched (too much dribbling I think!). After lunch I submitted my report to Max detailing what had been said, what happened and the results before resuming my normal duties for the afternoon which passed without incident.

WEDNESDAY 7TH APRIL 2010

Dear diary, another interesting day at the office and one that has given me much to think about! This morning I turned up for work as normal, made myself a coffee and checked my pigeon hole for mail. Normally it is empty but this morning there was an official looking envelope with just my name on it. Sitting down on a nearby chair I tore open the envelope to see a note from Liam asking me to see him immediately at the beginning of my next shift.

Having spoken to George and asked him to go on the morning prison rounds without me (showing him the note as I did so) I made my way up to the Governor’s office and knocked on the door wondering what he wanted to see me about.

“Come in!” called the familiar voice of Liam.

As I walked in and smiled in his direction he gestured for me to sit down at the desk in front of him, I was a little surprised to find that there was only the two of us in the room with no sign of Max or Adrian. When I made a comment to this effect I was told that this was a confidential meeting and was to be kept secret until a definite outcome had been reached. I was intrigued by this statement and asked him to elaborate.

“Okay Sam, I will explain. Do you remember the post-punishment meeting we had with Tyler? You do? Good. Well I’ve been doing a lot of thinking since then and the report you submitted to Max yesterday crystallised the matter for me and I’ve decided to put my plans into action but I wanted to run them past you for your input. I have decided to create the role of ‘Volunteer Punisher’, one for each wing, they will be responsible for the implementation of inmate punishment under the new rules introduced in March under the close supervision of the Volunteer Co-ordinator. It will serve two purposes, firstly it will free up our own officers and secondly it will lock our tougher prisoners into a role which should restrain their more unruly tendencies.”

“Right Sir, but where do I fit in your plans and why do you need my input?” I asked, still none the wiser.

“Well, I am seriously considering making you the Volunteer Co-ordinator. If you are interested in this role I will elaborate further, there’s no pressure but I am very impressed with your attitude and popularity with the inmates. I believe you are an ideal candidate.”

“Thank you, it’s fair to say that I am interested but what is involved and will it affect my normal duties?” I replied deep in thought.

“Once I have assessed your training needs and brought you up to speed, then you will be responsible for the selection, training and supervision of the volunteer punishers. You will also be responsible for their punishment should they break the rules of their roles. As you are no doubt aware the prison philosophy is to lead by example, so we will expect you to do so too. Your behaviour must be exemplary while on duty and be able to perform all the tasks you expect the inmates to do. I have drawn up for your reference a manual outlining the volunteer role and the sexual activities they will have to be adept at. As to it affecting your normal routines it is impossible to say at this stage as we have no idea about the amount of time the role will require. This is something we can assess as we go but there’s no need to worry, we have no intention of overloading you!”

“Sounds good to me, I’d love the opportunity to increase my experience and value to the prison service so please count me in. Is there any chance of seeing the training manual?”

Beaming broadly Liam reached behind him and pushed a posh looking presentation black folder with my name on it, I guess they had every intention of me taking on the role. I guess my ambition must be a little predictable?! Opening the front cover I scanned the introduction and turned to the volunteer role section and started reading avidly. From the corner of my eye I could see Liam watching me with a slight smile on his face, ignoring it I carried on reading. I was intrigued to read that the volunteer’s uniform was to be simply a red beret and a leather belt worn around the waist to which attaches two small tubes, one of KY and the other Crisco. No other items of clothing are permitted.

Looking up I asked “Will I be expected to wear this uniform and what about the inmates who are not permanently naked?”

“Absolutely not, your uniform is that of a prison officer, that doesn’t change in any way. As to the inmates, if they want to be volunteers then they have to wear the uniform, there will be no exceptions on this point. The uniform is designed to set them apart from the other inmates, be distinctive but at the same time not give them too much authority. After all compared to prison officers and the majority of inmates they will still be virtually naked.”

I nodded my understanding and carried on reading through the manual, I was just getting to the section about sexual activities when the phone rang breaking my concentration. Liam spoke on the phone for a couple of minutes, hung up and announced that events had overtaken us

“Please feel free to take the manual and read it at your leisure when you get home, but please keep it to yourself as the contents are confidential. I have scheduled your assessment for first thing tomorrow morning, I will get Max to reschedule your morning timetable to accommodate the assessment. Okay then? I’ll see you tomorrow morning in Richard’s consultation room”

With that the meeting was clearly over so I stood up, shook Liam’s hand and made my exit with my folder under my arm. I discreetly put the folder into the boot of my car for reading when I get home and went back to work.

This evening I made myself comfortable and read the manual from cover to cover. It was very well written and covered all the areas I could think of when it came to the volunteers and the role. However when it came to the sexual activities expected to be carried out I couldn’t believe what I was reading, it was very graphic and left nothing to the imagination! I must admit I was sporting a hard on until I remembered that Liam had told me that I would be expected to be an expert in all areas of the manual both on the giving and receiving as I would be training the volunteers.

Ho hum! I could always back out but that would be the coward’s way, after all I have been happy to undertake some of the activities listed in the manual so why not go with the flow and see how far I can stretch my boundaries? Not only that, my standing in the eyes of Liam and his team would be diminished and possibly jeopardise my shining new career. I went to bed wondering what tomorrow would bring.

THURSDAY 8TH APRIL 2010

Oh diary, where do I begin? It has been one hell of a long and exhausting day. Starting at the beginning would be the best place I guess, here goes.

Got up early, showered and shaved in preparation for my assessment with Liam, had breakfast and got to work twenty minutes early. I clocked on, checked my pigeon hole and then made my way over to Richard’s (the prison doctor) consultation room in the medical centre. Knocking on the door I waited for an answer as I could hear muted voices on the other side. Finally I heard a “come in” and I opened the door and went in to be greeted by Liam and Richard who were sitting round Richard’s desk discussing what looked like a medical form much like we had completed for the inmates during the post punishment sessions.

“Ah do come in Sam, sit on the couch for a moment please while I explain what this morning’s assessment is going to consist of” Liam said looking up from the paperwork.

I did as I was told without comment.

“Did you read the manual I gave you yesterday?” Liam asked.

“Yes Sir, from beginning to end. It certainly made for interesting reading and quite an eye opener!” I replied smiling.

“Indeed! I’m glad you liked it. Richard is going to do the usual medical checkups on you, we will then assess your body’s capabilities so we can determine what exercises you will need to undertake in the following days. Okay so far? Good. As before all we ask is for you to trust us, follow instructions and know that whatever you are asked to do is for your own benefit. Right let’s make a start. Firstly, would you please remove all of your clothing; you can place them on the chair in the corner and then stand facing us by the couch.” Liam said with a deadpan face.

I remembered what he had been like during the interview process and how he could change from being affable one moment to very hard and stern in the blink of an eye. He wasn’t the Governor of the prison for nothing! So without hesitation I disrobed as quickly and efficiently as possible, neatly placing my uniform and underwear where indicated. In less than two minutes I was standing in front of the couch, naked as the day that I was born with my hands behind my back (well I wanted to appear as relaxed as possible).

Richard then spent the next ten minutes going over my body with a fine tooth comb (I don’t mean literally) noting down every statistic, measuring my heart rate, blood pressure, peak flow etc. You name it he checked it with great care and fed the results back to Liam who faithfully wrote them down on the form. When he was satisfied he left the room for a moment before returning with a familiar contraption. I gulped quietly to myself, it was the portable colonic irrigator and I had seen this device in operation only nine days ago on (or rather in) Jarek so I knew what was coming next!

“Sam” Richard said “please turn to face the couch and bend over resting your elbows on it, then spread your legs apart as far as is comfortable.”

I did as I was told without saying anything, what was there to say?

Before long I felt greasy fingers feel between my cheeks and explore the length of my crack before finding their target, my anus. Then with one deft movement I felt a glob of grease being pushed inside and a couple of fingers massage my ring before they too were pushed up my rectum. I groaned in spite myself and was told by Liam to relax as much as possible, it would make it a lot easier for me if I did.

I was just getting used to the intrusion when I felt the fingers being removed to be replaced by the cold metal douching tube making my hole twitch in response. I looked over my shoulder out of curiosity; the tubing looked a lot smaller than it felt! Richard looked up at me and winked before returning his concentration to the task at hand. He switched the motor on and the irrigator started humming and vibrating, within seconds I felt warm water flow up into my rectum. Just when I started to feel full, the flow reversed and the water/faeces mixture left my body before the tube was pushed further up inside me, from the feel of it my inner ring had been breached and the tube travelled up into my bowels. It felt strange, not exactly painful but not comfortable either. I can only estimate that this went on for about fifteen minutes before Richard announced that the whole of the tubing had been inserted and no more faeces was coming out. He then slowly withdrew the tubing, I was relieved when it finally left and my hole was once more free to close up.

“Well done Sam, that went very smoothly” Liam announced, stepping over to me as Richard removed the machine from the room. “Now I would like you to climb up on the couch, lay on your back, bring your knees up to your chest and hold them in position using your arms.”

“Yes Sir.” I said and did as I was told.

“How are you feeling so far?” Liam asked as he snapped on a pair of latex gloves and started to grease them up.

“Okay, a little exposed. It’s not the first time I’ve been in this position Sir, Richard can vouch for that.” I said trying to sound as confident as possible and grinned in Richard’s direction.

“He’s right” Richard confirmed. “I had him like this just about a month ago in fact.”

“Good. I am now going to assess your anal ring’s tightness. You are of course familiar with the process because I know you have carried out those tests yourself on the inmates during the post-punishment assessments. I won’t waste breath explaining them to you, I am going to get straight down to business, so nice steady breaths Sam, try to relax and enjoy the experience!” Liam said chuckling as he smoothly slid one finger up my exposed rectum.

I didn’t actually find one finger uncomfortable; I guess being fucked by Sayeed put paid to being tight in a virginal way. I closed my eyes and practised relaxation methods in head which helped enormously when Liam inserted two fingers, there was distinctly less room available for them. He is skilled at his art I thought because I expected him to immediately try for three fingers but no, the two fingers slowly rotated and pushed in and out of my hole relaxing my ring remarkably quickly. As I felt three fingers attempt an entrance all thoughts of mantras and relaxation methods flew out of the window, I was now getting curious about the action going on at my backdoor. Lifting my head I looked between my knees to find that I couldn’t see very much as my cock and balls were neatly blocking my view so I let my head fall back onto the couch. All the while those three fingers were rotating and pushing inwards but my ring was now at full stretch and I was groaning loudly in protest.

“How much have you got in there because I don’t think I can take any more Sir” I asked with a slight trace of worry in my voice.

“I have currently got three fingers fully inserted but don’t be alarmed I am stopping there, for today at least. We have a lot of work to do on your hole to get it in shape for the task ahead. There’s just no way you can train the volunteers at present, this because you cannot demonstrate all of the techniques and you will risk serious injury if you attempt to. Starting from tomorrow morning, you are to come straight here at the beginning of each shift and we will start your training in earnest. Do you have any questions?” Liam asked as he withdrew his fingers, removed his gloves and wiped his hands on some tissue.

“No I don’t think so.” I replied quite truthfully.

“In that case, you’re free to wipe yourself clean, get dressed and return to normal duties for the rest of the day. Don’t forget Sam, none of this is to leak out yet.” Liam announced all smiles now.

“Thank you, I won’t forget.” I replied rolling of the couch and walked rather stiffly over to the box of tissues to wipe my bum clean of all the grease before getting dressed as instructed.

Back of the prison wing George tried fishing to find out what I had been doing but despite his best attempts I managed to avoid any slip ups and evaded his traps. Eventually he gave up and the day carried on as normal. At long last my shift was over and all I wanted to do was to have a long hot shower and vegetate in front of the TV with a beer or two or maybe surf the internet for an hour or two.

It wasn’t until I was halfway home that I remembered that I was supposed to be going jogging with Aaron and Jason, damn! Perhaps they might cancel and I will still get to have my evening on the couch after all. No such luck! At 7.00pm on the dot there was a ring on the bell and I opened the door to be greeted by two grinning young men telling me I must be getting past it as I took so long to answer the door. Past it indeed! I’ll show them I thought to myself. While they sat in the living room watching the TV I quickly got changed into my running gear, then we were off for a deliberately brisk jog twice round the park. Mission accomplished, I had two exhausted young men panting like there was no tomorrow by the end of the jog, while I had hardly broken into sweat.

“Never mind boys” I said with just a very slight smug tone in my voice “I’ll get you as fit as an old man like me before much longer.”

“Ha ha ha” was all they could manage between gasps for breath. Walking back to my flat we had to stop a couple of times due to cramps and stitches but eventually we got there and their mood lifted a little. As I turned the key in my door they were back to being their joking selves.

I let them shower first like I did on Monday, this time Aaron went first as he had to get home early to baby sit. By the time Jason returned from his shower with as usual a towel wrapped round his waist, Aaron was dressed and flying out the door with a “See you guys on Sunday at the Leisure Centre, bye!”

I decided it was time for my shower and invited Jason to make himself comfortable while I took my shower, he accepted my invitation with a nod and sat down on the sofa with the TV remote control. Five minutes later I was in the shower soaped up and just about to rinse off when there was a knock on the bathroom door and before I could call out I heard the door open.

“Sorry Sam, I know you’re having a shower and I really hate to invade your privacy but I’m bursting for a pee and I can’t hold on any longer. Do you mind if I quickly use the loo? I won’t be a minute.” Jason said with a pleading tone in his voice.

What could I say? He was already in the room.

“Sure go ahead Jason. Just be careful where you look, you might see more than you want to!” I said trying to be as jovial as possible as I rinsed the soap out of my hair and eyes.

“Don’t worry about me, I’ve seen loads of naked men, don’t forget I’ve always played loads of team sports and you get to see plenty in the changing rooms afterwards.”

I carried on rinsing off, I kept my eyes closed because I have this hatred of getting soap in my eyes (have had ever since I was a kid). By the time I turned the shower off I had expected the bathroom to be empty again, but no Jason was still very much present and was even offering me my towel! At a little loss for words I simply took the offered towel with a smile and started to dry myself off. There was little point in pretending modesty when he had just about seen everything there was to see. I couldn’t help but have the feeling that he was enjoying seeing me naked so I asked him outright.

“Jason, do you always hang around in the bathroom when someone is having a shower?”

“Guilty your honour!” he said without hesitating. “Unlike Aaron’s old man, mine is very liberal. Ever since a kid we, that is my dad and brothers, have always been very relaxed about our bodies, none of us think twice about walking into the bathroom when another is having a shower or using the loo. Okay with my mum it’s a bit different but then she has her own en suite bathroom which makes things a lot easier. She’s even used to us walking around the house naked, okay that’s normally after a night on the tiles or during hot weather admittedly. I guess that is why I feel so comfortable here; you and dad are very similar in some ways. I hope I haven’t made you feel uncomfortable by acting like this and please don’t say anything about this to Aaron because he wouldn’t understand and he’d only get the wrong end of the stick.”

“Fair enough, I hear what you’re saying, however I would prefer that you be upfront about things like this, people can get the wrong idea you know.”

“Okay Sam, I hope I haven’t offended you at all.” Jason said contritely.

“Offended? No not at all. Surprised? Well, yes I guess so.” I replied as casually as I could manage.

Well, I suppose I must be a bit of an exhibitionist (as if you hadn’t guessed by now) and decided that I would play a game with Jason to see if my feelings were correct or if he was being totally genuine and innocent in his actions. Having towelled myself dry I sprayed some deodorant on and then walked out of the bathroom, still starkers heading towards the kitchen. Behind me I could hear Jason’s footsteps following me not too far behind. Judging him to be visual range I opened the fridge door and reached in for a couple of cans of beer which were on the bottom shelf at the rear. In order to do this without crouching I had to spread my legs a little and bend at the waist, unfortunately this action exposed my hole and my tackle dangled nicely in the space between my thighs. I heard a stifled murmur so having hold on the cans I quickly stood upright and turned round in one smooth movement, catching Jason by surprise. There he stood, leaning against a work counter, feet crossed at the ankles, towel around his waist and just the beginnings of a tent pole!

“Would you like a beer? Can I offer you anything else?” I asked as innocently as possible.

“Anything else?” Jason replied, voice raised just a little. Something must have been lodged in it because he had to clear his throat before continuing “What do you have in mind?”

“Dunno really, I’ve got some chips in the freezer, or I can do us a salad. Actually, if you want to have a look in the cupboards and let me know if there’s anything you fancy. Personally I’m going to have a salad as I have to watch my weight these days, I don’t want to get belly or fat bum!” I patted both as I said this.

I sensed a deflation in him as he realised I wasn’t suggesting what he thought I had. His towel still had a slight tent pole but he ignored it as he stood up straight and said “If a salad is good enough for you then it’s good enough for me, after all it’s me who needs to lose the weight. Look at you, there’s not an ounce of fat on you anywhere!”

Smiling in acknowledgement I set about preparing a ham salad, not giving my nakedness another thought but making sure that I struck suggestive poses wherever possible. Jason didn’t say anything untoward but his tent pole never went down one little bit. Once we had eaten we moved into the living room and watched the 10 O’clock news on ITV. I sprawled out on the sofa, making sure that my tackle was nicely displayed and Jason sat in the armchair, for some reason he seemed to have trouble concentrating because out of the corner of my eye I noticed he kept glancing in my direction. After the news he decided that he needed to be getting home and so retrieved his clothes and got dressed before bidding me good night. Poor boy he just couldn’t help but look at my body one more time as he shut the door behind him, on the other side of the door I was grinning to myself knowing that my intuition had been right all along.

FRIDAY 9TH APRIL 2010

Last day of the week thank God! My poor hole will be getting a rest for a couple of days, from prying fingers at least.

Richard and Liam were waiting for me in the consultation room as I arrived, and it was straight down to business. I was told to strip and assume the position for being cleaned out. I won’t bore you with the details but it was exactly the same process as yesterday, although a little easier as I knew what to expect. The I was told to hop onto the couch but this time stay on all fours with my head on my hands (actually this position was identical to the one I got Jarek to assume last Tuesday).

It wasn’t long before I felt latex covered fingers tickling my anus, making me wriggle a little before I felt the familiar sensation of cold Crisco being pushed into my hole and smeared all round it. First one finger went in, then two, all the time they were rotating and massaging the anal ring. Their movement was hypnotic and I was almost in a trance when I felt a third finger join them. I shifted my weight a little and was asked if I was okay, all I could do was respond with an affirmative grunt. The three fingers massaged their way for what seemed an eternity, my hole was getting looser and I was just beginning to feel restless when they were withdrawn and I was told to climb off the couch and stretch my body for a minute while Richard fetched the next piece of equipment. Did I say piece of equipment, more like a cross between an item of clothing and an instrument of torture!

As I was limbering up, touching my toes and then the ceiling etc, Richard walked back into the room carrying what looked for all the world like a leather thong. I said as much to him and he nodded in agreement.

“You are right Sam. That is exactly what it is, although not one you are able to buy in Marks & Spencer! I just have to connect the attachment and we’re ready for your first fitting.”

Fitting for what? I asked myself. I didn’t have long to wait before I found out. Richard reached into a drawer and pulled out a box of what looked like black rubber objects, light bulb in shape with a metal screw thread at the neck end. There followed a brief discussion between Liam and Richard before an agreement was reached and the required object selected. Richard then picked up the throng and appeared to screw the “light bulb” onto the narrow part of the thong. Sometimes I can be so thick because I still didn’t have a clue about what was coming next! When he was satisfied that all was in order he knelt down on the floor and asked me to stand in front of him facing away, which I did. He then asked me to step into the outstretched thong, which I did, only then did it occur to me what the bulb was for.

“Please pull the thong up to your waist and maintain that position.” Richard instructed.

I did as I was told, then I felt a hand reach between my legs and take hold of the bulb before placing it against my anus and gently pushed it upwards. It felt bigger than it looked and was certainly bigger than the three fingers I had just accommodated.

“Spread your legs a little and push out as if you’re about to drop a log.” I heard Richard advise from behind me.

Well that paints and interesting picture I thought, but again did as I was told. All I can say is it worked, by spreading my legs I ended up squatting slightly and as I pushed out I felt Richard apply more pressure. In less than a minute the head of the bulb made its abrupt entrance into my rectum and my ring clamped shut tight around the neck.

“Aaaaaargh! That hurt!” I groaned.

“It’s okay, your ring will calm down in a minute or two, it’s just not used to stretching that extra bit” Liam assured me. “What we want you to do is to wear this thong when you go to bed each night, leave it in place all night and then remove it in the morning, okay?”

“Um, yes, okay I guess. Can I take it out now?”

“Is your anus still aching?” Richard asked.

“It is a little, I also feel very full like I need a crap badly.” I admitted quite frankly.

“In that case you need to keep it in a little longer to allow your body to adjust to the intrusion. Please climb up on to the couch and lay down on your front as if you’re going to have a massage, then RELAX.” Liam instructed.

As I lay there relaxing doing my best to ignore the object within, I felt fingers slip underneath the thong and explore the boundary between the neck of the bulb and my ring. For a couple of minutes they massaged all the way round several times before withdrawing and grasping the neck. I then felt the bulb being gently tugged, then pushed in further, wiggled around and then the cycle started again.

“How does it feel now?” Liam asked as Richard continued his ministrations.

“Okay actually thanks, I no longer feel any discomfort at all which I am surprised about” I replied.

“Good, that is progress indeed. We’re now going to take it out now so just relax and as before push out gently.” Liam said.

It came out with a plop, slightly uncomfortable but certainly not painful like it had been going in. I was then told the training session was over, I could clean myself up and get dressed. As I was dressing Liam reminded me that I was to wear the thong & insert the bulb each night until the next training session on Monday. Then it was back to work, this time George didn’t bother asking where I’d been as he knew I wouldn’t say.

This evening just before bed time in the privacy of my own bathroom I tried to insert the bulb again. Although I was using the same grease that Richard had given me, this time it just seemed so much harder! No matter how I tried it just wouldn’t pass my golden gates. I was getting very frustrated. Then I recalled the trick about squatting and pushing out at the same time, I am so glad no one was there to watch, it was all rather undignified. There I was squatting over the toilet with rubber bulb in one hand, the rest of the thong in the other hand to prevent it trailing in the water and me pretending to have a dump! Mind you, once again the trick worked, in it popped as quick as you like, but boy did I break out in a sweat and groan. It wasn’t so much painful more like a throbbing toothache which slowly faded away. With the bulb inserted I stood up and pulled the thong on and made my way to bed. What I do in the name of duty.......

SATURDAY 10TH APRIL 2010

Dear diary, if I am honest I thought today was going to be one of those unremarkable days but actually it ended on a high note so I guess I can’t complain.

Woke up this morning after a good night’s sleep, I had totally forgotten about the thong and bulb so was a little confused by the feeling as I normally sleep in bed with just a T-shirt on.

Went to the bathroom to remove it using the same trick as last night, I was surprised to find that my ring really didn’t want to let go of it but after a bit of huffing and puffing it shot out along with a load of shit behind it – major yuk! Not the best sight or smell first thing in the morning; I retrieved it from the pan and gave it a very thorough washing along with my arse which felt strangely loose. It was, I could easily stick two fingers up inside with no problem or lube!

Having recovered from that shock I got dressed, shaved, had breakfast and went shopping for the mundane things in life like food and groceries. Then home to more mundane things like housework, washing and ironing.

By late afternoon I was totally bored so I called Tom to see what he was up to. He said he was glad that I had called because he and Chrissie were entertaining Mike, Aaron and his wife Sally, Jason and his girlfriend Kirsty this evening and if I could join them it would make the numbers even. I leapt at the chance to have dinner with my two best mates, they’re always good for a laugh and Chrissie is lovely as is Sally. Kirsty I don’t know but knowing Jason she is bound to be pretty and educated. We chit chatted for a while before Chrissie came on the line and begged me to come as we hadn’t seen each other since the wedding, that was settled then!

Eight O’clock on the dot finds me knocking on the front door, which opens to reveal a laughing Chrissie (already half cut) holding a glass of red wine. She squeals in delight (that’s Chrissie for you) and gives me a hearty one-handed hug before dragging me inside and shutting the door behind me. By the sound of it I’m the last to arrive as the house is buzzing and rather noisy. I tell Chrissie that she is one swell looking lady in that little black dress, which only causes her to giggle all the more and informs me that my smooth tongue and an eye for the ladies hasn’t changed one little bit over the years (if only she knew the half of it!).

The sound of our voices in the hallway attracts attention and Tom sticks his head round the living room door, shouts hello and tells me to join the crew in the living room while the ladies finish preparing dinner. I do as instructed and as I walk into the room I am greeted by a united “hello” from Mike, Aaron and Jason all trying to offer me a can of beer or glass of wine. Holding my hands up in mock surrender I take a can of beer and proceed to make small talk with them until dinner is announced.

Dinner (or rather a three course banquet) was truly scrumptious, for starters it was homemade potato and leek soup with croutons. Main course was roast duck breast served with a medley of green vegetables, rosti potato cakes and a rich port sauce. For dessert homemade vanilla ice cream marbled with dark chocolate and a raspberry sauce followed by the obligatory coffee and mints.

It was during the coffee round that attention turned towards me and I received a good natured grilling over my current job as a prison officer. I talked about my role and the inmates I came into contact with (without revealing their real names) and some of the incidents that I had encountered. I successfully managed to avoid mentioning the sexual nature of some of my encounters and the new prison rules etc. I also managed to avoid any reference to the fact that I was no longer 100% heterosexual in my thoughts or activities. After what seemed like ages the attention turned to physical fitness and finally Kirsty came out of her shell. She thanked me for taking Jason under my wing, although he has only just started his training with me she has already noticed a difference. He has started to eat more healthy food, drink less alcohol (this night being an exception) and has been religiously doing all of the exercises I had given him. She thinks in the right light she can make out muscles underneath his belly! This brings resounding laughter from all except Jason who pulls a hurt expression before throwing me a sly wink. Then Sally nudges Aaron and makes it clear that he has no room to laugh as his middle is beginning to spread! Tom regains control of the situation by expressing the fact that really all the guys in the room (except me, of course) could do with a little more exercise and less girth round their middle, perhaps Mike and he could join the rest of us on Sunday at the swimming pool and see how they get on. I thought this was a splendid idea, but what about the ladies though? By the end of the conversation we were going to be a group of eight in the pool on Sunday, I wonder if we can get a group discount?

I finally staggered in through my front door at about 1.30am (technically Sunday I know but I don’t count it being the next day until I’ve been to bed and woken up again) and was all set to collapse into bed when I saw the rubber bulb waiting on the side for me. I ummed and aahed over it, thought sod it one day won’t make any difference, then changed my mind and picked it up on the way to the bathroom.

I sat on the toilet and emptied out as best I could then greased my arse up and also the bulb. Perhaps it was the alcohol in my system or my deadened sense of time but it (the bulb) seemed to disappear up inside me more easily and quickly than I expected. It did have one unexpected side effect, it gave me a raging hard on as it gently rubbed and banged against my prostate from the inside. There was no way I could go to bed like this, so with one hand feeling the neck of the bulb and my ring clamping hard round it, and the other wrapped round my cock I jacked myself of to a pretty earth shattering orgasm over the bathroom basin. Deciding now enough was enough I really needed to get to bed I washed myself off (and the basin), pulled up the thong and made my way to the bedroom where I quickly succumbed to oblivion.

SUNDAY 11TH APRIL 2010

If I’m honest diary, today didn’t actually start until about 11.45am when I woke with a jolt to the sound of my phone ringing about six inches from my ear – not a good way to start the day if you’ve got a little bit of a hangover....

I was just a little groggy when I picked up the phone and mumbled a hello down the line only to be greeted by the chirpy tones of Chrissie.

“Morning Sam! I just thought I’d give you a quick call to make sure you got home safely & that we’re still on for the swimming session this afternoon. How’s the head this morning?”

“Urrr morning Chrissie, I think, what time is it? Yeah got home okay and yes I’ll be there at the leisure centre at 2pm as agreed! My head is still on my shoulders but feeling distinctly tender, I guess that will teach me to finish up that last bottle of red with you... how’s your head by the way?” I asked as I came to, slowly.

“I’m just fine, thanks” Chrissie assured me “must get on, still got some clearing up to do before we meet up. As to the time, it’s nearly mid-day. See you shortly, byeee!”

And then she was gone. Just as well she woke me up as I didn’t have all that much time to get spruced up etc. First things first, into the bathroom to shower and remove a certain object. Crikey, my arse must be getting like a bucket because it’s getting easier to take the bulb out, I didn’t have to squat over the toilet and strain, I simply started to squat down and as I did so it popped right out with little discomfort. Curiosity got the better of me, I just had to assess the damage to my hole, not only did two finger slide right on up inside with no trouble but so did three! Progress indeed, I’m sure that Liam will be pleased. However I had no time to dwell, I quickly showered and shaved before getting dressed and packed my bag with my swimming gear.

I got to the leisure centre just before 2pm to find Jason and Kirsty waiting outside for me and the others; we made small talk and recounted the events and conversations from the previous evening. Throughout our conversation I monitored discreetly Jason’s behaviour towards me, but he acted impeccably and not once did he act in anyway other than being Kirsty’s partner, to my relief. Ten minutes later the others had arrived and we made our way into the changing rooms.

With the five of us (Tom, Mike, Aaron, Jason and myself) getting changed it was a very relaxed affair, even Tom seemed at ease and managed to joke around as we undressed and got into our swimming trunks. Privately I had to agree with Tom, both he and Mike were carrying a decent sized spare tyre round their middles. They will definitely need to go on a diet and exercise regime before they can join Aaron, Jason and myself jogging round the park on a Tuesday and Thursday. An hour later after a mixture of hard swimming and relaxed messing around in the water the eight of us are sitting round a table in the cafe overlooking the swimming pool. I was lost in thought when I felt a sharp nudge in my ribs bringing me back to the present.

“Well Sam, what do you say? Are you up for it?” Aaron asked with a slightly exasperated tone to his voice.

“Up for what?” I asked in all innocence.

“Having a last lad’s night out this Friday before we cut out all the booze and grub as part of our diet and fitness regime” Tom explained.

“Yes, sounds good to me. Is it down the Kings Head shall we make it a special night and go into town?” I asked the group in general.

“Oh it’s got to be town if it’s going to be our last night out for a long time!” Jason cried out all enthusiastic like a big kid.

“That’s decided then” Chrissie announced “girls we’re going to paint the town red too! Kirsty and Sally, get your thinking caps on, we have four days to plan our night out.”

Shortly afterwards the conversation naturally dried up and we went our separate ways.

MONDAY 12TH APRIL 2010

Back to work already, oh how the weekends pass so quickly. The alarm clock went off and I swung into action on autopilot, even removing the rubber bulb from its night time lodging in my rectum had become part of my routine. I hate to admit it but I could insert and remove it with ease....

At the prison I made my way directly to Richard’s consultation room and knocked on the door before walking in to find that Richard was alone. He greeted me with a warm smile and explained that it would just be the two of us to start off with as Liam had been called away at the last minute but he hoped to join us later. With the preamble over we got straight down to business, I stripped naked and Richard cleaned me out thoroughly using the portable colonic irrigator. Then having climbed onto the couch, kneeling on all fours in the usual position Richard examined my anus to assess my progress with the rubber bulb. I felt him smear the Crisco round my hole and then fingers moving around the outside and inside of it. The movement was constant and I had difficulty keeping a track on how many there were and what they were doing, it all became a pleasurable blur.

“Well Sam, I can see that you have followed our instructions and the result is very pleasing indeed. You should be proud of your achievement, your progress is excellent.” Richard announced as he withdrew his fingers from me.

“Thank you Richard, I must admit it was not easy at first but by this morning I really become accustomed to it and I was even finding its presence pleasurable in a weird kind of way. When you say I have progressed, by how much and what is the target you have in mind?”

“I’m glad you are finding the insertions pleasurable, that is one of our objectives, you will then be able to pass this knowledge on and be able to demonstrate it to the trainee volunteers at the appropriate time. As to progress, on Friday morning you were just able to take three of Liam’s fingers, however this morning you were able to easily accommodate three of my fingers and so I am moving on to the next step of your training. By the end of this morning I expect to be able to insert at the minimum four fingers, but hopefully depending on your ability and willingness to stretch I will be able to insert the whole of my hand into your rectum. Then for the next couple of mornings we will be working on depth before moving onto width. How does that sound? I bet you’re glad you asked that question now aren’t you?” Richard said with a hearty chuckle.

“Mmm I think I will reserve judgement on that for now, if you don’t mind. To be honest, I’m not in a position to protest; after all I’ve had my fist up Jarek a couple of times now. He’s survived the experience intact and even seems to enjoy it despite being straight.” I replied looking over my shoulder at him as I spoke.

“Okay, shall we carry on then? Before we do, are you comfortable or do you need to stretch your legs because it may be some time before we can stop again.” Richard asked.

It was a good idea so I climbed down off the couch and did a number of stretching exercises under the watchful gaze of the doctor. After five minutes I climbed back onto the couch and assumed the customary position.

“Sam, I’m going to start stretching your anal ring further than it’s ever been to date, so relax as much as you possibly can. If at any time you feel pain you must let me know immediately. Discomfort is to be expected but pain is a big no no, do you understand?”

“Gotcha, I will do.” I mumbled with my face half buried in my hands.

Almost immediately I felt more Crisco being packed into my rectum and then pushed further inside by a couple of fingers, I could feel the grease softening and melting because it’s presence seemed to diminish gradually until I could no longer sense it. Unlike the fingers! There were definitely three fully inside me constantly twirling around, pushing in and then pulling out and repeating the whole cycle. I gave up counting after the fifth cycle and my mind began to wander all over the place. I was broken out of my trance with the sound of the door opening and Liam’s voice greeting us both.

“So guys, how is the patient doing?” Liam asked laughing at his own joke

Richard, without slowing or stopping his hand movements in any way, proceeded to discuss his findings and plans at great length. It was all very technical and made me feel like an object or piece of stock, as a result I quickly lost interest and started drifting away again. That is until I felt a hand reach beneath me and take hold of my bollocks, giving them a quick massage before moving onto my erect cock. I didn’t even realise I had an erection.

“So Sam, I see you’re not adverse to the treatment the good doctor has been administering, this is excellent news and I hope you are as proud of your progress as we are. You will make a very good Volunteer Co-ordinator, as you have a prison officer, your can do attitude has not gone unnoticed I can assure you. Just out of interest, do you know how many fingers are currently in your hole at the moment?” Liam asked.

I tried to count Richard’s fingers which were still moving round in their usual cycle but my anus had become so desensitised that I had no option but to guess so I said “Three?”

“No, Richard actually has four fingers fully buried inside and from where I’m standing I don’t think it will be much longer before his thumb will be joining the other fingers.”

“That’s good” was all I could think of to say.

After what seemed an eternity I began to feel a new sensation in my rectum, it was one of fullness and my ring felt tight like it hadn’t felt since the day I was fucked by Sayeed. Richard’s hand had stopped its motion and was stationery, no, that’s not quite true, it was moving very slowly if at all in the direction of my rectum. My ring was finally putting up some resistance and so he applied a little more force to his pushing resulting in me moving a little up the couch.

“Sam” Liam said with a serious tone to his voice. “I want you to breathe deeply and do your best to relax as much as possible, we’re almost there.”

“Yes Sir.” I said through gritted teeth as it was getting distinctly uncomfortable now.

Then all of a sudden as I was doing as I was told, it hit me like a tidal wave, drawing an “aaaghh!” from my lips, my ring gave up its resistance and allowed Richard’s coned hand to slide inside, as it did so his hand balled into a fist and my ring clamped shut around his wrist.

“Jeez! Is that really your fist inside me?” I growled.

“Oh yes, it certainly is.” Richard confirmed “I’m going to hold it still so that you can get accustomed to its presence then I’m going to move it around and I want you to tell me how and what you feel okay?”

“Okay” I said panting heavily “For a start it felt like my ring was on fire, then I felt I desperately needed to go to the loo. Both of these sensations are fading now leaving me feeling very full down there but not unpleasantly so. As you move your hand around I can feel it both from the inside and also the outside which seems very strange indeed. Ah, now you’ve just brushed my prostate because I’ve felt a surge of blood to my cock which had started to go soft again.”

“Excellent feedback Sam, you’re really in the zone now. Keep those memories secure because you’re going to need them when training the volunteers so that you can tell them what to expect.” Liam said before continuing “In a few moments Richard will start to withdraw his fist, there may again be some discomfort at the point of exit, but as with the rubber bulb the more you do it the more you get accustomed to it and the less discomfort there will be.”

Richard then added “Start breathing deeply, relax and imagine you are going for a dump, push a little but not too much. Ready? One, two, three here we go.”

“Eeeeeeyooow!” I cried as Richard’s hand was released from my hole, leaving it gaping wide before it slowly closed up again. I collapsed slowly onto the couch in exhaustion, sweat pouring from every pore in my body. I laid there motionless, my mind was all over the place as if I’d had too many pints on a Friday night, however my peace was abruptly disturbed a couple of minutes later by a pair of hands pushing my thighs apart and then exploring the crack between them. Before long once more I felt fingers exploring my hole and then smoothly glided on inside; my poor ring was too exhausted to put up much resistance. At the same time Richard lifted my hips and slid a pillow underneath me to raise my bum slightly into the air and provide Liam with easier access to my hole.

“Well done Sam, that’s it, push out a little, welcome my fingers. Great! That’s now four fingers inside, let’s tuck that thumb in behind them and see if you can take my hand too.” Liam encouraged me.

I backed onto the invading fingers as best I could while pretending I wanted to evacuate my bowels, the technique seemed to be working because before very long I felt the cone of his fingers getting wider than ever and then came that sticking point when the widest part is reached. That moment seemed to last forever but then with a momentary burning sensation his fist slid inside me with my ring closing slowly around his wrist. I reared up in response but this time was able to keep the desire to growl almost within, just a little bit crept out between my gritted teeth.

“Excellent work!” was all Liam said in response before saying “Right then, I’m going to pull out now and then that’s today’s training session over with. I know I’ve said it several times already, but very well done Sam, I’m proud of you.”

“Thanks Liam, it would be great if we could call it a day, my arse is getting a little sore now!” I said quite sincerely.

Five minutes later after a bit of pulling and puffing (on my part) Liam’s fist vacated my rectum to my relief and I was provided with several wads of paper towelling to wipe myself clean of all the grease which had been smeared over my nether regions. As I did so Liam asked me to take some time out of the normal routine today and draw up a plan and schedule to select the six Volunteer Punishers out of the prison community ready for presentation to him in the morning. No pressure then! As I got dressed back into my prison uniform Liam reminded me that this is still highly confidential so no talking about it, he didn’t want the inmates to get wind of it before the prison is ready to roll it out. I agreed that I would keep it strictly to myself.

Back on the prison wing George asked me if I was okay as I seemed a little quiet, I grimaced and said that I had a stomach ache (which was true). He was genuinely concerned and said that I should take a break after the rounds had been completed this morning. I took him up on his offer as this would be an ideal way to somehow draw up a “beauty contest” come competition to select the six “lucky” volunteers. By the time I returned to work I had at least half an idea about what I was going to suggest, the rest of it I would think about tonight, which I did over a large pot of coffee and all distractions excluded i.e. no TV, the answer phone twitched on, my mobile switched off and the door bell disconnected. There was no way I was going to be disturbed!

TUESDAY 13TH APRIL 2010

It was a late night last; I was up until 1am putting the finishing touches to my presentation until it was polished to my satisfaction, so when the morning alarm went off I wasn’t really ready to get up and face the ordeal waiting for me at work. But like the trooper that I am I got up and was actually a little early for work, down to the traffic I’m afraid not my superhuman speed.

I will cut out the repetitive bits diary, after all you know that each day this week I will be going straight to the consultation room where I will be cleaned out and fisted by either Richard or Liam or both in order to ‘educate’ me. Actually this morning it was only by Richard and his sole mission was to get my anal ring totally used to being stretched wide by a fist, so for thirty minutes he methodically pistoned his fist in and out of my hole until it no longer caused me any discomfort and in fact I was actually beginning to enjoy it despite myself and the situation I was in. All too soon it was over and after withdrawing his fist for the last time Richard showed me techniques for closing my hole up again as if nothing had ever happened. I was impressed and my regard for Richard has increased immensely as a result.

Dressed once more I made my up to the Governor’s Office and knocked on the door, decidedly nervous and holding my presentation folder under one arm.

“Come in!” Liam called out.

As I opened the door and strode in trying to appear confident I was in for a shock, I was expecting to be making my presentation to Liam. Instead I was greeting by the smiling faces of Liam, Max, Adrian, Archie (the prison officer who had greeted me when I arrived for my interview) and George.

My face must have been a picture as I stopped in my tracks and stammered out a “Hello guys, I wasn’t expecting to see you all here this morning.”

After he had stopped chuckling Liam said “Sorry Sam, sorry about the lack of warning about your audience. I decided that you were nervous enough about doing the presentation without having the added pressure of knowing that you would have an audience too. You are no doubt wondering why the others are here.”

“Yes Sir, I am more than a little curious after all that you have told me.” I said quite frankly.

“As you know Max and Adrian are my deputies and business partners so are always included on major decisions like this volunteer business. Archie is here because he is an ex-union representative and his experience will be invaluable in ensuring that all we do is legal and above board i.e. make sure that the relevant rules and regulations are adhered to. Finally George is here as a witness and will be taking minutes for the meeting, he has also been part of your assessment to see if you kept your vow of silence. I am glad to learn that not one drop of information has George received from you and so you have passed that test with flying colours. Right then if everyone would like to make themselves comfortable Sam will start his presentation.”

Gulp here goes I thought!

“Okay, please bear with me for this is the first presentation I have done in a long while so I apologise if I appear a little nervous.” I said after clearing my throat a couple of times. I looked down at my notes to give myself breathing space and time to gather my thoughts before continuing.

“My assignment has been to establish a method to find six Volunteer Punishers, one for each prison wing. It will allow us to identify which inmates have the drive, desire, ability and the right attitude to carry out this important function. After a lot of consideration I realised that it will need to be a combination of management selection and peer selection, you know a bit like the TV show ‘X-Factor’ except the voting public will be fellow inmates. This is how I envisage it will run.

Week 1: We announce the competition and make it clear that it is open to all willing applicants with the auditions being held in the Chapel. The method of selection will be by answering questions, those that get the answer wrong will be eliminated; inmates who answer correctly go on to the next round of questions. By the end of the evening the number of applicants will be whittled down to twenty four applicants.

Week 2: This week each contestant will be given a task to complete which lasts all week. At the end of the week the inmates will vote on who carried out the tasks most successfully. Twelve inmates will be eliminated by the voting to leaving twelve remaining contestants.