Diary of a Prison Officer Ch. 01

"So, would you still describe yourself as being straight or bisexual now?" Liam asked with a raised eyebrow.

"I guess, if I'm being honest I'm swinging more to being bisexual if this morning's experiences are anything to go by" I replied, before continuing with "Why? Does it make any difference?"

"No, it makes no difference at all. I was curious that's all."

It was now 12 Noon and right on time there was a knock on the door and in walked Dinesh, the other inmate who thinks that I am gay (I was beginning to wonder what he knew that I didn't). I think it would be fair to say that his is striking rather than handsome in the classical sense, not only in his looks but also in his demeanour. Authoritive would be a good way to describe him. I would put him in his early forties, of Indian origin, dark skin with a full head of hair cut fashionably short and a close cropped beard, again trimmed in a fashionable style. His body was hairy but he clearly kept it neatly trimmed, he was heavy set without being overweight, toned without being overdeveloped. He carried himself well; with confidence as if being naked was the most natural thing in the world. Perhaps this isn't surprising considering the fact that he was a master fraudster!

As before, while he stood before Liam with his arms crossed before him, I took my time to study him and wondered if I would get to fuck him like I had Eduardo.

"Okay Dinesh" Liam said having done his speech "Outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Gay"

"Have you ever had sex with a man?"

"Yes, of course I am gay."

"Was it anal or oral sex, were you passive or active?"

"Both oral and anal, I have done everything you can think of and have enjoyed it all."

"Okay, final question for now. When was the last time you ejaculated?"

"Yesterday, I fucked and sucked off one of the guys on my wing."

"Thank you, if you don't mind the doctor is now just going to carry out a few physical checks to verify your answers."

"Be my guest, I have no reason to lie to you."

Richard and I worked smoothly as a team, he weighed Dinesh's balls concluding that they had indeed been emptied recently, while I donned on a new pair of latex gloves and retrieved the KY. By the time I was ready Richard had instructed Dinesh to bend over the desk and spread his legs for our inspection. He was more than happy to oblige and even helped us by resting his chest on the desk and using his hands to spread his cheeks. I could tell that his hole had seen action because as with Eduardo it wasn't clamped shut tight, if anything it was slightly more open which I found curious.

I liberally applied the KY to his anus, which quivered in response and my fingers. I gently pushed my index finger inside and met no resistance, so I withdrew it and inserted a second finger, again I met no resistance. It was time to lube up a third finger, I was expecting the same resistance that I had with Eduardo but no, the three fingers slid in easily. With the three buried fully inside Dinesh I asked him if he was okay, he replied that he was and that there was plenty of room for more. I glanced and Richard who raised an eyebrow and encouraged me to continue, so withdrawing once again I applied some more lube and started to insert four fingers, again they slid inside quite easily. I now had the attention of the whole room; Max, Liam and Adrian along with Richard were now standing round me to get a good view of the proceedings. Richard told me to leave my fingers inside Dinesh and to tuck my thumb in behind them making a cone before pushing my hand further inside. I carefully followed his instructions and was surprised to find my hand sinking inside up to the widest part of my hand, where at last resistance was met. Dinesh was breathing heavily and now supporting himself on his elbows, looking over his shoulder he told me to keep going because he could take it and started to push backwards against me. I kept up the gentle pressure from my end and slowly the resistance from his ring gave way and my hand slid in smoothly up to my wrist bringing a sigh from him and the guys standing next to me. For a while his ring clamped tightly against my wrist, once it had relaxed I gently pulled my hand out with a quiet slurp and the hole slowly closed behind me. Dinesh stood up and turned to face us; I was a little disappointed to find that his cock was flaccid rather than being stiff like the other guys had been after I had explored their arse.

"Welcome to the noble art of fisting Sam, I think you're a natural, well done." Liam said patting me on the shoulder.

"I would agree with you there" Dinesh agreed. "Will that be all Sir, or can I help you with anything else? Like return the favour perhaps?"

"Er, no, that will be all for now but thank you for the offer!" I managed to reply, my cheeks had clenched so hard I was getting cramp in them.

Liam intervened and thanked Dinesh for being so amenable, his medical records were now complete and that he was free to collect his belongings from the box and get dressed. Dinesh nodded in response before striding over to his box and quickly got dressed. He repeated the invitation to me with a wink and then left the room with his possessions before I could respond.

Still puzzled by the state of Dinesh's cock I asked Richard for an explanation, if there was one.

"Sam, it's simple physiology really. Dinesh was concentrating so much on relaxing his anus that his arousal levels were suppressed. You will find that in a more relaxed situation and prolonged activity that his arousal levels would have risen again and it is common for recipients to orgasm spontaneously as Eduardo did earlier on this morning."

"You're absolutely correct Richard. I have witnessed this and indeed experienced it on several occasions." Liam added.

I was stunned by this latest comment and could only look at him in surprise. Ignoring my expression Liam announced that it was now 1pm and time for lunch, we had one hour before the next inmate was due. As we made our way down to the dining hall small talk was made and continued until we sat down in the private area for senior staff. We sat in silence eating our food before Liam started talking business. He asked Richard for his opinion on this morning's proceedings and whether or not I would be able to assume his role for future sessions. Richard gave his feedback on the morning and to my relief gave me a big thumbs up. However I had a couple of issues to raise.

"Future sessions? You mean that there will be more of these? I thought this was a one off!" I said in all seriousness.

"Good God no, this is simply the first one, we will be carrying out cell searches randomly for the foreseeable future in a bid to eliminate the prohibited activities. We predict that these type sessions will be repeated on a weekly basis and with training this is something you and Adrian will be able to do without the need for Max, Richard and myself to be present. As you can appreciate this is time consuming and we simply can't spare the manpower, plus we need to explore the processes for the next level of punishment."

"The next level?"

"Yes, the public corrections but this is a little further down the road, we haven't even reached the stage of repeat offenders yet but that will come soon, probably within the next month when we have a new batch of inmates. The new ones always try to push the boundaries." Liam announced with confidence. "This afternoon I want you to assume Richard's role, he will be there simply to advise you if necessary. You know what's required so I don't think it will be too much of a problem and you have shown a great deal of competence, a willingness to learn new skills and expand your experiences beyond your comfort zones."

"Thank you. I will do my best this afternoon."

By now lunch time was nearly over so we made our way back to the governor's office and prepared ourselves for the last two sessions of the day.

At 2pm there was a knock on the door and in walked Jarek from E-Wing, I could tell immediately that he was of Eastern European origin, Polish in fact, just by his colouring. He was of average build and height with light brown hair and pale skin. As he stood with his back to me listening to Liam's speech I couldn't help but look at his white cheeks, clearly they had never seen the light of day. Unlike the four guys before him he didn't appear comfortable with his nakedness judging by the way he kept his genitals covered by his hands despite Liam's invitation to relax.

Then Liam started to ask the same questions he'd used this morning.

"Okay, Jarek, outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Straight"

"Have you ever had sex with a man?"

"Never, it is disgusting and against God's rules."

"How have you felt about being naked for the last 48 hours?"

"Very uncomfortable, it is degrading having others stare at your body all the time."

"Do you think the punishment will deter you from offending again while in prison?"

"Definitely, I cannot tolerate being like this again."

"Okay, final question for now. When was the last time you ejaculated?"

"With all due respect that is none of your business; however I have to admit I had a wet dream a few days ago."

"Thank you, if you don't mind Sam is now just going to carry out a few physical checks to verify your answers."

"What do you mean physical checks?"

It was at this point I stood next to Jarek and explained what I would be doing. He frowned and was clearly unhappy with this, however he did place his hands behind his back when I asked him to and made no comment when I gently cupped his balls to weigh them. I decided they did feel heavy and wrote this down against his records indicating that he hadn't ejaculated for several days. But when I asked him to turn round and bend over this was a step too far for him and he point blank refused to despite my assurances that it wouldn't hurt. In the end I had to get assertive and pointed out that if he failed to comply with my request he would not be permitted access to his possessions until he did so, in other words he would remain naked until then. His jaws were clenched tightly as were his fists but slowly he turned round and bent over at the waist. I slipped on a pair of latex gloves, lubricated the index finger of my right hand and with my left hand spread his cheeks. Even with my untrained eye I could tell his hole was virginal, it was so tight and clearly clenched that I had to tell him to relax several times. When that didn't work I resorted to teasing it gently before pushing my finger tip just inside. He reared up in response and clamped down hard on me pushing me out, it actually hurt my finger! I stood up and announced that the test was now over, as far as I could tell nothing had ever been up there.

His relief was immense and when Liam invited him to collect his belongings he ran over to the box and scrambled into his clothes, muttering in Polish all the time, before quickly disappearing out the door.

Liam asked me how I thought it had gone; I concluded that it had been good experience for me to show how different the reactions can be to what is asked of the inmates, he nodded in agreement. With that it was time for the final inmate of the afternoon, Tony from G-Wing.

When Tony knocked on the door and walked in I was sure I was going to have the same difficulty with him as I had had with Jarek. I would say that he was probably an ex-Hells Angel in that he had tattoos all over his arms and neck, still wore his hair in a ponytail despite being in his fifties and had numerous piercings all over his body. He had a decent body except for the beer gut which he wore with pride and had a reputation for being handy with his fists.

In his defence his manner was easy going and appeared completely comfortable with his nakedness; standing quite casually listening to Liam doing his speech, then came the questions to which I listened with interest to see what the answers would be.

"Okay Tony" Liam said. "Outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Straight"

"Have you ever had sex with a man?"

"Yes, inside here only, not much choice is there?"

"Was it anal or oral sex, were you passive or active?"

"Both oral and anal, I have fucked a few guys and been sucked off too but that's my limit."

"Okay, final question for now. When was the last time you ejaculated?"

"This morning, I received a blow job in my cell."

"Thank you, if you don't mind Sam is now just going to carry out a few physical checks to verify your answers."

"Whatever, it's all the same to me."

Gaining confidence, this time I decided to be seated and had already slipped on a new pair of gloves before I asked Tony to stand in front of me while I weighed his balls. Although they were large in size I gauged that they were quite light confirming his statement that they had been emptied this morning. With this new confidence I asked him to turn round, bend over and support himself by holding onto his knees which he did with no hesitation. This presented me with a hairy crack and an anus which looked to me like anything but virginal! I applied a generous amount of KY to his hole and deftly inserted my index finger up his rectum bringing a little sigh of contentment from Tony. Withdrawing it I inserted two fingers again with relative ease, I was beginning to wonder if I had another Dinesh on my hands, but I needn't have worried because Tony was unable to accommodate three fingers. This led me to the conclusion that Tony was actually taking it up the arse despite his assertion to the opposite. I wrote these thoughts down on his report by made no comment to Tony himself.

I decided that I had finished testing him so invited him to stand up and clean himself off using the tissues on the side. As he did so he swung round revealing an erect cock of average length but with a comparatively large head, anyone on the receiving end of that would certainly feel it I thought to myself. He must have read my mind because he invited me to sample it any time I like as I was just the type of guy he liked to fuck with, I thanked him for his offer but declined it as tactfully as I could. He smiled and shrugged his shoulders then asked if he could have his possessions back now. As with the other five inmates Liam thanked him for cooperating with us, that his records were now up to date and yes, he could collect his belongings and get dressed.

Ten minutes later I was sat round the table with the other four for a thirty minute discussion on my progress this afternoon. At the end of the meeting I agreed to give running the post-punishment sessions a go as I was confident of my abilities to handle the punished inmates.

And that diary was the end of my long and tiring day at work! Driving home I mulled over the day's events and my reaction to the different situations I had come across. By the time I got home I hadn't reached a conclusion other than to take each day as it comes and make sure that I don't get pressurised into doing things I don't feel comfortable doing.

FRIDAY 19TH MARCH 2010

Dear diary, compared to yesterday work was uneventful, business as usual you might say. Everyone apart from Tyler was dressed as before and you would have been forgiven for thinking nothing had changed, and yet it had. There was a degree of calmness about the place and there was a little more respect for the staff, at least on the surface and just as importantly there was less bickering between inmates. As I walked back to my car at the end of the shift, I was both glad the week was over but at the same time I was looking forward to the next week too! Went down the King's Head and met up with Mike and Tom for our usual get together. It was great to let my hair down and talk about things other than law and order, the only trouble I had was as the beers flowed it got increasingly harder to keep my mouth from spilling the beans over the unorthodox events in the governor's office.

WEDNESDAY 24TH MARCH 2010

I think it would be fair to say that today was another eventful day at the office, so to speak. It was visiting day and one that will go down in history as the first real test of the new regime and I am relieved to say we pulled it off to great effect. The inmates concerned have been left in no doubt that the management mean what they say and that the rules will be implemented.

The day started off as usual with a briefing meeting for the day ahead, after that we did the rounds on the wings before getting ready for visiting period. As the inmates filed in and greeted their visitors waiting for them I took my position at one end of the room along with three other prison officers spaced around the room. Our role was to provide a visible deterrent to any obvious misdemeanours, but it was the hidden CCTV and microphones which would be used to detect any rule breaking. Our CCTV control room would feed back through our ear pieces if any inmate was to be detained after the visiting session.

For an hour I stood there carefully watching the inmates but for the life of me I could not spot any wrongdoing, however as the visitors filed out of the room my earpiece crackled into life and informed me that Jarek, Sayeed and Gus were to be detained. Jarek indeed! It was only yesterday he had declared that he had learnt his lesson, clearly not. I'm going to enjoy this I thought to myself. As was prison policy we had to have two officers per inmate for our own protection and also to prevent possible claims of abuse etc. George and I selected Jarek (at my suggestion) and as he made to rise from his seat I walked over to him and placed a hand on his shoulder and said.

"Not so fast Jarek, we need to have a word with you."

"Oh shit guys, what now? Why do you keep hassling me?"

"You were observed on CCTV receiving a small packet from your visitor and slipping it down the front of your trousers. As you are well aware this is against prison rules and you are required to surrender it immediately." I replied in the most authoritive voice I could muster.

"I haven't done anything wrong and I don't have to prove anything. This is typical, you're just targeting me because I'm Polish and think I will take your crap." Jarek said getting agitated.

"Come on Jarek, you can do this the easy way or the hard way, which one do you want?"

"Just fuck off and leave me alone! I'm going back to my cell; now get your hands off me." He growled and stood up shaking my hand off his shoulder and marched off.

We couldn't let him get away with this unacceptable behaviour and rebelliousness, so in unison we ran after him, caught up with him and pinned him to the wall, with his back to us. Before he could react we had his hands behind his back and quickly handcuffed, then turned him around facing us.

"So it's the hard way then." George said sternly before continuing "You do realise that you have just broken another rule which is refusing to comply with a request made of you by a prison officer. By my calculations that is the third infringement since the new rules came in, so not only will you be permanently losing all your personal possessions you will also be the very first recipient of the public correction in the chapel. I hope that you are proud of yourself."

Wisely Jarek said nothing but I could tell from his expression that he was majorly pissed off by this announcement, in fact he must have been boiling inside because he suddenly blurted out

"You are corrupt and perverted you pigs. I thought this country was fair and lawful but it's not, it's disgusting and you make me sick!" Having got this out of his system he stood there glowering as if to dare us to take the next step. We had no option but to continue and show that we meant business. With a nod from George I knelt down in front of Jarek and undid his belt and pulled it free from his jeans, then undid the button and unzipped the flies before pulling them down to his ankles. There was no sign of the packet seen on the CCTV.