Diary of a Prison Officer Ch. 02

"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.

Week 3:This week it steps up a gear. Each contestant now has to don the uniform of a Volunteer Punisher and start training in all aspects of the role. During the day they will learn the theoretical aspect of the role; then in the evening the contestants will receive training in the practical aspects in the Chapel's punishment room. The whole session will be watched by the inmates in the auditorium area and at the end of the training session the inmates will vote off the least favourite or capable contestant. This will be repeated each day until there are seven contestants left.

Week 4:The final week sees the volunteers carrying out their duties for real, each day they will be moved to another wing so that all inmates can assess them in action before the final vote at the end of the week.

That gentleman is the outline of my selection process. Do you have any questions or concerns?" I asked.

"Thank you Sam" Liam spoke up "that was well presented and I like your idea very much. However I do have a question, you mention management selection but I can't see where in the weekly elimination schedule our influence can be exerted."

"That's a good question Liam" I replied smiling. "My intention would be that ahead of the competition we will select a number of inmates who we consider suitable, meet with them in private and feed them the right answers so that they will make it through to the final twenty four. It is then down to them if they make it to the final."

"I like it!" Max announced "A cunning way to get our favourites into the final, yet we will appear to be totally open in allowing the inmates to democratically choose their punishers."

"Well said Max, I think we should run with this one" Adrian said thoughtfully "What does everyone else think?"

There was a unanimous decision to accept my proposal so it was signed off by Liam there and then. Next came the nitty gritty stuff, sitting round the meeting table we thrashed out the timetable, the design and wording of the competition, the questions to be asked at the audition round and what the tasks the contestants would need to complete. Last on the agenda were the inmates we would like to see included in the final twenty four contestants.

After much discussion and at times heated debate, the twelve inmates we agreed that should be included were Tyler, Flick, Eduardo, Dinesh, Jarek, Tony, Bert, Darren, Carl, Martin, Gus and Sayeed. The timing for the individual briefings would be within a couple of days of the posters going up. It would be done discretely so that no one, least of all the inmates would suspect that anything untoward was going on. The posters will be put up on Friday 16th April 2010 so that the inmates have the weekend to discuss and think about entering the competition. With that agreed the meeting was over and it was back to work for us, however with most of the morning gone it was a just short stint for me before my shift finished.

I got home and the first thing I did was to step into the shower with a cold can of beer, I wanted to wash the last traces of the grease from my body that tissues just simply couldn't do along with the accumulated sweat from my pre-meeting nerves. With the beer warming my insides and the hot water pounding my body all my cares and thoughts about today's events slipped away down the shower's plug hole.

Towelling myself dry I turned my attention to this evening and the impending arrival of Jason and Aaron for our jog around the park. The two lads arrived a little later, dropping off their change of clothing and we made our way to the park. I decided to be kind to them tonight and started the jog off gently only starting to pick up the pace in the latter half of the lap. Just to add a little pressure to the exercise I engaged them in conversation while jogging, they quickly sussed my tactics but I wouldn't allow them to let the conversation drop. At the end of the first lap I let them catch their breath while jogging on the spot before we carried on with the second lap, as it happened they led the way and I let them dictate the pace which I didn't mind in the least. Who would? I had two pairs of pert buttocks straining beneath running shorts, muscular thighs and arms pistoning back and forth in unison. They were a sight for sore eyes indeed! By the end of second lap I came to the conclusion that their level of fitness had increased perceptibly. I kept this thought to myself as I didn't want to boost their egos too much! To extend the exercise I insisted they jog back to my flat much to their moaning.

As they staggered up the steps to my front door I was chuckling inside, the sight of their sweat soaked clothes and bedraggled appearance was a far cry from their normal cock sure attitude that comes with guys in their prime. I unlocked the front door and held it open for them, as they passed by all I could smell was very sweaty bodies – Yuk with a capital Y!

"Right you two, no lounging around on my nice clean furniture with your sweaty, dirty clothes until you have showered and changed. I mean it. Run along while I sort out some refreshments." I said before walking off and headed for the kitchen to raid the fridge for fruit juice and whatever I could find to eat.

A minute later I heard the shower running and the familiar sound of Aaron whistling floated in from the bathroom, it was such a trivial domestic sound that it caught me by surprise when I started to wonder what it would have been like if I had had children with my ex-wife. I was still thinking about it when I heard footsteps behind me and a "can I do anything to help?" brought me back to the here and now with a jolt.

Looking in the direction of the sound, the sight that greeted me made me lick my lips in reaction, I caught that action in mid motion and discreetly pulled my tongue back in. There stood Jason as cocky as ever, smirking, stark bullock naked, framed by the doorway using the lint to hold onto. I took a moment to take in his physique, his hairy muscular legs and finally his cock which was standing at half mast and bobbing to erection under my gaze.