Diary of a Prison Officer Ch. 01

He smiled quirkily and said "Sure. I think I can do good."

Within ten minutes his cell was empty and the box was brimming full of his clothing and personal bits and bobs, the only items left was his bedding and the clothes he stood in. Now we turned our attention to Flick, telling him to remove the clothes he was wearing. Backing away from us he made for the doorway in a bid to escape, without success as Pete blocked his route and drew his stun gun.

"Now son, you can do it the easy way and do as you're told or you can do it the hard way. We will stun you, then strip you and you'll wake up aching all over. Either way you're going to be naked for the next 48 hours." Pete told him as he cocked the trigger of the gun.

Gulping audibly Flick thought for a second or two before pulling his prison issue sweatshirt over his head and handed it to me, quickly followed by his T-shirt revealing his smooth chest covered in green and red dragon tattoos with their tails trailing down his muscular biceps. Despite myself I could not help but admire his physique and thought he really was quite attractive in a bad-boy way. Catching my eye he grinned impishly before slipping his hands inside the waistband of his jogging bottoms and pushing them down to his ankles. As he stepped out of them he straightened up revealing the fact that he had been going commando and his decent sized cock bobbed at half mast indicating that he wasn't too bothered by this turn of events. Last to go were his socks which he threw in the direction of the box announcing that he had complied with our request so, were we happy now?

Pete nodded indicating that he was satisfied with the outcome and turned on his heels pushing the now padlocked box in front of him. As we filed out of the cell Flick followed us asking what he was supposed to do now and what about the box. Being the last one out I turned round, trying to keep my eyes on his face I replied

"You need to carry on with your normal routine, your prison job is to be carried out and meal times attended etc. Your box will be returned to him in 48 hours time."

"That's easy for you to say, it's not you who's naked!"

"True enough, but rules are rules and you broke them. Make sure you don't break them again otherwise you'll be in this state again and next time it will be permanent. Besides, I don't think you'll be the only one in this predicament by the end of today." I smiled as I walked out onto the landing.

Flick followed me clearly wanting to continue the conversation, momentarily forgetting himself until he realised he had the attention of the entire wing. Frowning he looked around before yelling out

"What are you lot staring at? Never seen a man's knob before? Get a life!"

I chuckled at this latest outburst all the way down the stairs and caught up with my colleagues before leaving the A-Wing and making our way over to B-Wing. Word gets round fast in our prison; the inmates on B-Wing were waiting for us including our next target, Tyler Abegundi. Flick had been our warm up in preparation of this man; Tyler would need more careful handling. He didn't bother with weapons or drugs to rule this wing, he didn't need to; he was a mountain of a man, tall and very muscular with huge fists which could break bones with ease. He was normally placid but when riled he went ballistic and his sadistic nature became evident. Self-confident as ever he casually leaned against his cell's door frame clearly in view of the wing as if holding court.

"Gentlemen." his voice boomed along the landing towards us "You won't find any prohibited items in my cell; you're wasting your time. So don't think of pulling that stunt you did on Flick with me."

"Come on Tyler, don't play dumb with us." Pete retorted with equal confidence "You know your activities have been closely monitored by us. Rule 2 - Prohibition of Violence & Abuse was broken this morning when you threatened to break the jaw of your new cell mate in the wash room because he hadn't yet agreed to spread his legs and let you shove your donkey dick up his arse. As this is your first offence under the new rules you will forfeit all of your personal possessions for the 48 hours."

"I don't think so and you can't make me!" was the gruff reply.

Peter walked up to Tyler and spoke quietly in his ear indicating that he had a proposition for him if he co-operated with us. This change of tactics clearly surprised him because Tyler's eyebrows rose momentarily before nodding his head in the direction of his cell and walked inside.

"So what are you guys offering me in exchange for my kit? It had better be good or I am going get real mad with you" he said, glowering down at us as if to emphasise his point.

"Relax will you." Pete replied in a calming tone. "What we have in mind you will definitely enjoy. You will no doubt be aware of the new rules and the penalties that will be imposed. We will need volunteers to assist in administering punishment for persistent offenders and you are the perfect candidate what with your physical attributes."

"What do you mean by attributes?"

"Firstly you're built like a brick shit-house so no one messes with you, we don't want any resistance from the inmate being punished and your reputation will be an advantage. Secondly you must have the biggest dick in this prison which when on show will put the fear of god up most inmates reducing repeat offending."

"So what's in it for me?"

"Basically you get to shove your dick or anything else you care to use up the arse of any repeat offender that is due to be publicly corrected. If I'm not mistaken you have to go to great lengths to persuade guys to let you shaft them, this way you get your way without having to break any rules and as often as corrections are required. So are you interested or not?"

"If this is for real then count me in, it's an effing nightmare trying to get my rocks off in this place. What do you want me to do then to make it look a genuine bust?" Tyler was all business now and even seemed keen to go with the sweetener offered to him, it clearly appealed to his desire for power over other inmates.

"For a start, we'll handcuff you, stand you outside on the landing while we strip your cell and pack the box up. You can curse at us if you want, we'll ignore it. Then I'll get my stun gun out and threaten you to comply when your handcuffs are removed. It would be better to strip on the landing so that all can witness your reluctance to comply."

"Well what are we waiting for? Cuff me and let's get the show on the road, my balls are getting heavy and I need an arse to break real soon."

Without further delay I brought his hands behind his back and handcuffed them before pushing him out of the cell onto the landing where the inmates were still avidly watching the proceedings betting on the outcome. As his cell was stripped and his belongings packed into the box I stood guard over Tyler as he cursed and swore at us acting his part really well. A few minutes later the job was completed and Peter joined us with stun gun drawn instructing me to release the handcuffs. He then told Tyler to remove his clothing voluntarily or be stunned and we'd strip him while he's out cold. Still acting in character Tyler snarled at us but started to undress as instructed. He crouched down and removed his trainers and socks, handing them to me before standing up and pulled his sweatshirt over his head revealing his heavily developed chest and arms. His black skin gleamed like polished obsidian in the prison lighting with just the odd curly hair dotted over his chest. Without pausing he took hold of the waist band of his jogging bottoms and pushed them down past his equally developed thighs and calves. Stepping out of them he stood tall and proud in just his boxer shorts, pausing to see if we were satisfied. Peter nodded to the shorts and indicated that they were to come off too. Sighing loudly Tyler pulled his boxers down slowly and stepped out of them. He was deliberately drawing attention to his cock which although was flaccid, hung down his leg some seven inches long and three fingers wide. No wonder no one wanted to accommodate it! His balls were equally magnificent like black polished billiard balls. Apart from a few discreet quiet whistles there was no reaction from the rest of the wing, whether it was due to being in awe or because of Tyler's fearsome reputation I didn't know nor particularly care. We informed that in 48 hours his box would be returned to him before leaving the wing to carry on to C-Wing, then D-Wing, E-Wing and finally F-Wing.

All in all it was very draining having to mentally battle with naturally reluctant inmates to persuade them to part with all of their possessions and clothes. In fairness to them, there was only one inmate we had to actually use a stun gun on, the rest saw sense and complied with our demands.

The final job of the day before heading home was to place an amnesty box on each wing with an additional warning that from tomorrow everybody's room will be searched. Today was a gentle warning; tomorrow the rules will be enforced more rigorously!

WEDNESDAY 17TH MARCH 2010

Day three of the new rules and if anything it was harder than yesterday, not so much mentally as physically. Due to time constraints we were working in twos with fifteen minutes allowed per cell. This meant that we had little time to chat with the inmate concerned other than to tell them what was expected of them and the consequences if they did not comply. Following yesterday's events everybody knew the score and each amnesty box had been pretty well filled up with weapons and drugs. As a result most cells proved to be clean of prohibited items and on each wing there was on average maybe only five or six inmates who had be stripped of their clothes and possessions, they had been foolhardy enough to believe that we wouldn't carry out our threats.

At lunchtime we finally sat down in the prison canteen which we share with the inmates. I was surprised how well the naked inmates were integrating with the clothed ones. I had half expected them to remain hidden in their cells waiting out their 48 hour punishment but I was wrong in my assumption. The ring leaders had gained some kudos by flaunting their nakedness, by showing that they had lost everything at the hands of the management yet carried on as if nothing had happened just added to their reputation. As to the other inmates it very much depended on their standing beforehand, but in general the lower ranks stayed where they were and subjected to the expected light hearted ribbing you get between men. I was just finishing my desert and chatting to George, a prison officer who had started at the same time as me, when I felt a tap on my shoulder. Turning reflexively I was faced with a black cock which all but slapped me on the nose, I recognised it instantly, it was Tyler's. Semi-erect it was now about nine inches long but still three fingers wide. Despite myself I couldn't help but notice that his cockhead was black as well, the only other black guy I had seen naked had a pink cockhead, I made the mistake of voicing this observation. He had clearly been planning to bump into me and this simply added to his amusement and he chuckled as he sat down opposite me.

"Well boss, you don't know that much about us black guys do you? I suppose you've only ever stuck to your nice white boys, eh?"

"No Tyler, I never had sex with either black or white guys. I am actually straight; I have been all my life."

"Yeah right, I've seen how you've been watching me when you think no one's looking and I'm not the only one who thinks like me."

"Really and who else is of the same opinion?"

"Well, Flick for a start and Dinesh from D-Wing thinks so too. We think it's cool to have gay prison officer, it's not often we get to have one."

"I've already told you I'm not gay. Why do you think I am and what difference would it make?"

"Apart from the way you look at us, it is the way you interact with us and the genuine interest you show in our well being. If you were totally straight you wouldn't give a shit about us. When you were outside my cell yesterday and as I removed my shorts you just couldn't take your eyes off my body could you? I'm not imagining it but I'm sure I saw you unconsciously lick your lips and adjust your trousers. Am I right? As to the difference it would make, perhaps none, who knows. It's just nice when a guy can be honest about himself, mutual respect can grow as a result, even friendship?"

"Like I said before I've never had sex with a man before but you're right lately I have been finding the male body strangely fascinating despite myself. I didn't realise that I had been making it so obvious, I apologise, it is unprofessional of me and it won't happen again. I do hope that we have mutual respect, it's part of my job to engage with inmates and help where I can."

"Okay Sir, I get you, well if there's anything I can do to help you out you just let me know." Tyler said with a wink as he stood up and joined the other inmates making their way out to the kitchen gardens for the afternoon shift.

I looked at George and asked him what that was all about.

"Dunno Sam, but just looking at his member makes my eyes water. How anyone man or woman could accommodate that thing is beyond me!" he remarked grimacing.

The afternoon bell rang indicating that lunch was over. The rest of my day was spent doing paperwork and supervising the art class.

THURSDAY 18TH MARCH 2010

Dear diary, much of today has been spent returning the confiscated possessions back to the gang leaders, or should I say they had been instructed to collect them from the governor's office. If I was of a suspicious mind I would think that my sexuality was being tested to the extreme. I'm not making much sense am I? Perhaps as always it's best that I start at the beginning. Then you can see for yourself if my suspicions are correct or not.

When I clocked in this morning there was a note in my pigeon hole that I was to report to the governor's office first thing. I knocked on the door and Liam's distinctive voice invited me in, I had a sense of déjà vu because Liam, Max and Adrian sat behind the long desk as they had at my interview. In the far corner of the room I spotted the six locked boxes containing the gang leaders' possessions. I sat down on a chair to one side as indicated by Liam before I was told that they wanted me to act as an assistant to the doctor and be a witness to the proceedings. Fair enough I thought; it would be a change from the routine so I said that I would be happy to oblige in whatever capacity required. This seemed to be the correct response and as three men smiled, Liam picked up his phone and spoke briefly into it before making small talk with me for a couple of minutes until Richard (the prison doctor) walked in wearing his familiar white coat and carrying a small leather bag I had often seem him with.

At 9:00am on the dot there was a knock on the door and in walked Flick, he hesitated briefly at the sight of the five of us but carried on walking until he stood in front of the desk facing Liam as instructed, with his hands clasped behind his back displaying the tattooed dragon's tails curling down his arm. Liam informed him that his possessions were to be returned to him but before this there were some missing details on his medical records which needed completing and this was the ideal time to collect the information. Flick nodded his understanding, I couldn't help but notice that he clenched his buttocks repeatedly as he nodded and I wondered if he was more nervous than he was letting on.

"Okay, Flick" Liam started apparently reading from a record sheet. "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, but only within the prison. You know how frustrating it can get inside."

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

"Oral, I was sucked off."

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

"Yesterday evening, I gave myself a hand job in the showers."

"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've got nothing to hide."

Richard took this as his cue, slipped on a pair of latex gloves and asked Flick to face him. He gently cupped Flick's balls in his hands and appeared to weigh them. He agreed that they seemed reasonably light in keeping with being emptied yesterday. He then asked Flick to face towards the desk and rest his elbows on it, thereby bending over at the waist and exposing his anus for examination. It also gave me a perfect view of it. Even to my untrained eye it looked small and tight, virgin territory a small voice said in my head. Richard retrieved a tube of KY from his bag and liberally lubricated his finger and Frick's anus. At this latest development Flick looked over his shoulder frowning but said nothing. I pulled my chair forward until I was within touching distance of his anus so that I could get a good view of the impending penetration. Richard nodded approvingly before saying

"Good thinking Sam, I want you to see exactly what I am doing because I shall require your assistance in a minute. Is that okay?"

"Sure." I said nodding, not taking my eyes off the small puckered pink hole before me.

By now Flick had stopped looking over his shoulder, instead he was looking straight ahead of him and as Richard's finger tip started to push against the tight entrance he bowed his head to disguise the discomfort or embarrassment he was experiencing. After a couple of minutes it was becoming apparent that Richard would be unable to enter further than the first knuckle without causing Flick pain. It was then I had an idea, or rather a memory floated to the surface.

"Richard" I said tapping him on the elbow. "Why don't you try the technique you used on me during my medical assessment? It worked for me, so I can't see why it won't work for young Flick here."

"Excellent idea!" he replied, gently pulling his finger out of the tight hole. "Flick, would you please stand up and turn around. No, really there's no need to cover your erection, we're all professionals here and we've seen it all before many times. That's better, please relax, it will make things a lot easier for you. Okay, now step backwards until you are sitting on the table. Okay, now lean backwards until you are lying on your back, bring your knees up to your chest and wrap your arms behind your knees. That's excellent, thank you."

Oh my god! I was now beginning to see what attracted men to other men..... and what Richard had seen the day he examined me. Flick's anus was being forced to relax due the position he had assumed and at the same time was more visible to all in the room. Flick was doing his best to retain his dignity as all five of us were now standing round him peering down at his hole.

Richard wasted no time in applying further lubrication to the hole and using the same distraction techniques on Flick that he had with me. He spent about ten minutes discussing with him his opinions of the new rules, at the end of which his whole finger was buried up to the hilt and gently stroking his prostrate which was bringing gentle groans from Flick. Adrian pointed out to the group that Flick was now sporting an erection which brought a chuckle from everyone except Flick.

"Oh man did you have to say that?! It's bad enough that I have a finger up my arse but I am sporting a boner too!"

Liam appeared to consider this for a minute before announcing

"That's a fair comment actually. Okay, here's what I propose. Flick, you can let go of your legs. Max, you take hold of his left leg and Adrian you take his right. That's it, hold them up and slightly apart that way Flick will be more comfortable and you see that his cock has now been released. Now Sam, what I want you to do is to slip on a pair of gloves and lubricate your index finger. That's right, now slowly insert it into the anus taking the same care that Richard took. When your finger is fully inserted I want you to feel around until you can feel his prostate."