Diary of a Prison Officer Ch. 02

"Jason, what on earth are you doing?" I asked in mock exasperation.

"I'm only doing what you told me to do." He replied, walking into the kitchen and standing rather close to me. "After all you did say that you didn't want us touching your nice clean furniture with our dirty clothes. I thought I'd prevent that from happening by making sure they were out of harm's way from the start. Did I do wrong then?"

"Noooo, I suppose not" I replied.

"And you did say that you run a relaxed joint here, did you not?" he continued.

"Yes, this is true. Okay okay, now that you're here why don't you help yourself to a drink while we wait for Aaron" I suggested trying to keep my voice on an even keel and resist running my hands over his pert buttocks.

Thankfully Aaron joined us within a couple of minutes with his towel firmly wrapped round his waist, he did a double take at Jason's nudity before shaking his head and wryly commenting "have you no shame boy?"

Laughing Jason said "None at all, now that you've finished hogging the shower I can perhaps use it myself!"

As Jason disappeared into the bathroom Aaron turned to me and asked "Doesn't his antics bother you at all?"

"No, not really" I replied "If anything, he makes me laugh and he reminds me of myself when I was his age. Why? Does it bother you?"

Aaron was thoughtful for a moment then said "Yes, I guess it does. He is so brazen in the way he flaunts his body, okay he's not bad looking but why does he have to do it so much?"

"Well, if you got it flaunt it I guess is the rule that he's working by. To be honest you both have great bodies and are decent looking so I am a little surprised that you are not more like Jason." I said sitting down at the kitchen table with a glass of orange juice in one hand.

"I've got Dad to thank for that, he's instilled in me a conservative view of exposing my body and it's very hard to overcome."

"I find that if you want to overcome a mental block then the best way to do this is to face it and do the very thing you find hard to do." I said in the most fatherly tone possible.

"So in my situation if I want to be more like Jason what should I do?" Aaron asked seemingly puzzled by my latest statement.

"Simple" I replied "remove your towel and let it drop to the floor. Remain naked until Jason returns and it's time for you to go on your way. I will ignore your nakedness like I did with Jason, I am sure that you will find that before long you will feel more relaxed. The more you practise being naked, the more comfortable you will become with your body."

"Are you serious? What just drop my towel? Okay, if you say so, but don't tell dad will you. I don't want him to think I'm queer or anything." Aaron said with just a touch of edginess to his voice.

"Yes, yes and of course I won't. You don't have to do anything you don't want to but I just thought it would help. After all at your stag do you stripped off in public happily enough." I said shrugging my shoulders and took a sip of my juice.

"That was different, I was drunk and I got swept up in the moment. Right now I'm stone cold sober but I hear what you're saying. I guess, we're in private and no one's going to see or say anything, so here goes."

Taking a deep breath Aaron unfastened his towel and let it drop to the kitchen floor but kept his crown jewels covered with his hands. Standing there a little self-consciously he looked at me for approval.

"That's all very well but my towel is getting dirty on the floor so please pick it up, fold it neatly and put it on the side over there please, then why not come and sit down at the table and have a juice with me. That way you will still be naked, getting accustomed to being so but not feeling like you're on display all the time." I said, deciding that I would not let him get off the hook so easily.

Sighing, Aaron did as he was instructed, picking up the towel and folding it necessitated him uncovering himself and as he walked back to the table I got a good view of him and his tackle. Although his hair was a blonde (dark straw if we're being accurate) his body hair and pubes were several shades darker, made all the more striking by his naturally fair skin. Whereas Jason was a very big boy (10 inches by my reckoning at the stag do), Aaron was more your average guy which I wonder is perhaps part of his modesty problem. He made a good attempt of appearing relaxed but it was clear that he was relieved to be sitting down covering his modesty.

I let him be and we made small talk, I was good as my word and made no reference to his nakedness. Jason sauntered into the room, still naked and flushed red all over from the hot shower. He looked a little startled at the sight of Aaron sitting at the table without a stitch of clothing on and started to smirk.

"Less of that young man, it's all very well for you to flash your tackle around without a care in the world but not everyone is as confident as you. Aaron is trying to overcome his shyness and you laughing at him isn't going to help. We're taking it one step at a time and the first goal is to get him accustomed to being naked." I admonished him and then smiled encouragingly at Aaron.

"Thanks Sam, I appreciate your support. Jason, as my best mate, I would also appreciate your support, this is not easy for me as you well know." Aaron piped up.

Putting his hands up in the air in mock surrender Jason said "Okay guys, I get the message and I am sorry for not being more supportive. A thought has just occurred to me, this is a safe place for us to be naked without judgement as we've already discussed previously. Why don't we make it a rule that whenever we come over clothes are not permitted and we all have to be naked, that way Aaron will get all the practice he needs and won't feel the odd one out. What do you reckon?"

"Sounds like a good idea to me" I nodded in agreement. "What about you Aaron?"

"Yeah, sounds cool to me, it will make things easier for me.... I guess. But no word of this is to leak out right?"

Both Jason and I nodded in agreement before I said "Well that's sorted then, perhaps I can go for my shower now then."

"Aren't you forgetting something Sam?" Jason asked; then added in response to my quizzical expression, "You are still wearing your running gear, if this is a clothes free zone; they need to come off NOW!"

Chuckling at his impudence I nodded in agreement, stood up from the table and proceeded to remove my trainers placing them under the table where I normally keep them. Then I peeled off my muscle vest, pushed down my running shorts, leaving just my jock strap to go. Then in one smooth movement I pushed them down too, stepping out of them I put all my dirty washing into the washing machine before turning round with a smile on my face and arms spread wide and saying

"Are you happy now? I think this is enough for one day, I could do with a shower and you guys have got women to get home to, so get dressed and vamoosh. I will see you on Thursday."

A little while later I had my flat back to myself and enjoying my second shower of the day. As the soap suds rinsed away I slowly stroked my cock thinking about Jason's hot body and all the ways I would like to ravish his body given half the chance. Just as my imagination had me on my knees, with my hands wrapped round his waist and my face buried between his cheeks licking his tight little heiny hole, my balls decided it was time to unleash their load sending several jets of creamy spunk arching across the shower to hit the glass shower door and slowly slide their way down.

Recovering from my intense orgasm I looked down at the slug trails with disgust and quickly showered the congealing cum down the drain. And that diary brings the end to a very tiring day indeed.

WEDNESDAY 14TH APRIL 2010

Compared to yesterday, today was average really. Well average that is if you call having your boss stick his fist and half his forearm up your arse! No word of a lie, I kid you not, by 10am this morning I had been cleaned out and prepped by Richard. Okay Richard had been loosening up my hole ready for Liam who then using his experience pushed his fist further up my rectum than I thought humanly possible. Apparently he had found breaking the resistance of my inner rectal ring a challenge, but one that he was up for, and eventually succeeded in doing. Unable to stifle the groan I growled like a grizzly bear, face flushed red and sweat pouring down my face my inner ring opened up and his fist slid on by up into my bowels. Only the width of his muscular forearm prevented him from going in all the way to his elbow. I looked down between my legs (I was laying on my back with my arms wrapped round my knees) with an expression mixed with awe and horror at the sight of his arm half buried inside me, while Liam had a look of pure angelic rapture.

"Sam, you are a star do you know that? I have never worked with a guy who is so willing to explore his boundaries and push far beyond them. I have seen you in action as a fisting top, now I have seen you in action as a fisting bottom and I am very impressed indeed, you are so versatile. There is absolutely no way that I will consider any one else for the role of Volunteer Co-ordinator." Liam said with a great deal of pride in his voice.

"Thank you Sir, I guess I have the army to thank for being able to push personal boundaries but I'm really not sure what the benefit of having your forearm buried in my butt will be in my role as Volunteer Co-ordinator." I asked as politely as I could.

"It's not so much the actual act you understand, although it must be said you have a very fine arse, but it is more of a test of your willingness to put your trust in me. Your level of trust is commendable, I couldn't ask for more" Liam responded and at the same time started to slowly withdraw his arm and fist.

As my inner ring was breached by his hand I arched my back in response, groaning as I did so. Some part of me must have enjoyed it as my previously flaccid cock slowly engorged with blood until as his fist finally slipped out of my anus my cock was fully erect and bursting to erupt. My ring must have been slow to close because I could feel cool air flowing into my rectum before being expelled as my rectum closed up along with my ring. I lay there relaxing with my eyes closed for a moment, I was about to get up when I felt something warm and wet enclose my cock's head.

Startled I looked up to see Liam's head slowly descending on my cock until he had swallowed the whole of my shaft in one smooth move, then slowly and lovingly his head started to bob up and down. Jeez it felt good! I let my head slink slowly back on to the couch, closed my eyes and gave myself up to the sensations of the gorgeous blow job I was being given. Finally with my hips bucking wildly I could hold back no longer and I gave into the impending orgasm. Load after load of jism shot out of me and straight down Liam's throat, not one drop did he let slip out and he didn't stop sucking until my cock had run dry and receded to its flaccid state once more. I looked up at Liam in askance.

"Sam, it's the least I can do considering how you have accepted without question all that I have asked you to do. I wanted to show you that as far as I am concerned this is a two way street and I have an inkling that it was an acceptable payback for you." Liam said with just a trace of a smile on his face.

"Yes Sir, it was an unexpected bonus that's for sure!"

"Right then, before we get back to normal duties is there anything you want to talk to me about?" Liam asked quite casually.

"Actually, there was as it happens. I know we agreed that we would speak to our preferred candidates once the posters have gone up but I'm concerned about timescales and I just can't see us getting through all the candidates in time without suspicions being aroused. I am hoping that you will allow me to start talking to them today" I said as I cleaned myself up and started to put my uniform back on.

"Sam, you're in charge of this venture now, if you think that's the right thing to do, then go for it. All I ask is that you keep me posted on events or if you encounter any problems. Okay?"

With that the training session was over and I headed over to the prison wings and pay the first candidate a visit, namely Flick on A-Wing. Since the 48 hour removal of personal possessions punishment Flick had been true to his word, he had behaved himself and not got into any more trouble, thereby keeping his possessions and clothing in the process. However he had lost none of his cockiness and as I walked into his cell closing the door behind me it was very much on show in his mannerism and posture.

After he bantered with me about why I was paying him an unannounced visit I got straight down to business and explained about the purpose of my visit. I outlined the role of the volunteer punisher, broadly what would be involved and that we actively wanted him on board. Once Flick made it clear he was interested I gave him a run down on the questions that would be asked so that he would have the correct answers to get through the qualifying round. As he never asked about the uniform I kept quiet on it remembering his reaction to being stripped naked for his punishment. I decided that he could cross that bridge when he got to it. My final comment was for him to keep his mouth shut about our little meeting and to remember to register his application when the posters were put up on Friday. Flick's mind was racing with the possibilities as I walked out of his cell.

On to B-Wing where I met just the person I was looking for playing snooker with a fellow inmate, who was just about to pot a red ball. Taking the opportunity while Tyler was waiting to play his turn, I walked up to him and whispered in his ear.

"Tyler, I know you're playing snooker but I need to have a private chat with you right now in your cell, alone. It will be only for a few minutes and then you can continue with your game."

Tyler frowned for a second, glanced at me but seeing that I was being serious nodded once in agreement and told his play mate that he would be back in a minute to continue the game. As Tyler was a force to be reckoned with there was no argument from the other guy.

As I followed him up the metal staircase to his cell I could not help but admire his muscular frame and jet black skin which had the optical effect of making him look like a moving obsidian statue. On entering his cell I closed the door behind me, turning round I was faced with the vision of Tyler sprawled out on his bed, hands behind his head, legs spread and his python of a dick snaking across one thigh. His balls hung loosely down between his legs. Despite my best intentions I could not help but look at them remembering the day that I had managed to accommodate the whole of his mammoth cock down my throat. Tyler chuckled loudly before inviting me to do the same thing again for him.

"Thanks for the offer" I replied "and as flattering as the invitation may be, I am here on official business not for personal pleasure. How have you been getting on since you voluntarily surrendered your clothing?"

"Oh man, I've been having a ball!" Tyler laughed again. "At first I was quite self-conscious, I know that might sound strange coming from me but it's true I really was. It's one thing when you are stripped as a punishment, you have no choice in the matter, but after the post-punishment meeting I voluntarily gave my clothing away in the hopes of becoming a volunteer punisher. I had to come up with a plausible story as to why you've kept my clothing and I'm not kicking up over it as the other inmates expected me to do. After a few days it was old news and the guys stopped asking me questions and simply accepted that I was going to remain naked from now on. It was made easier after Jarek's antics because suddenly I was no longer the only inmate to be permanently naked. Now no one takes any notice except those that are either gay or trying to usurp my position as top dog on this wing."

"Go on" I urged "I feel a story waiting in the wings just waiting to be told!"

"Do you remember how I told you when you first raided my cell that I had trouble getting any form of relief in this place?" he asked.

"Uh huh, I sure do"

"Well that isn't a problem anymore. There's a young lad on this wing, I'm sure you know him because he's received the 48 hour no clothing punishment too, by the name of Gus. He's very self-confident and easy going." Tyler said.

"I think I know the guy, he looks very similar to Jarek but his hair is paler." I asked pretending to be uncertain.

"That's the guy!" Tyler agreed nodding with a smile before continuing "It must have been the day he got stripped as punishment I first really got acquainted with him properly so to speak. I was sitting in the canteen during our lunch break, chatting as normal to a couple of old timers when Gus walks over with his lunch on a tray and sits at our table opposite me. I don't take much notice because up till now we've moved in different circles, however mid-way through his lunch he makes out that he's dropped his fork and crawls underneath to retrieve it, or so I think."

"What happens next?" I ask, genuinely curious.

"The next thing I know is a pair of hands pushing my knees apart and a pair of warm wet lips kissing my knob end. I don't know who was shocked the most; me, my knob or the guy I was talking to! I looked under the table in surprise while my cock rapidly stood to attention under Gus's expert administrations. No word of a lie he had swallowed the whole of my cock down to my balls within thirty seconds, and oh boy the feeling was out of this world! His head was bobbing, my body was sawing and I couldn't help by groan with pleasure. All too soon I could hold off no longer and with a shudder my balls exploded jism down his willing throat. He only came up for air when my cock ran dry and was back to its normal size, then he resumed his position at the table without looking at me, with fork in hand and continued eating his meal cool as a cucumber."

"Now that's what I call a lunchtime treat!" I laughed.

"From that day on any time that I've wanted to dump a load I've only had to nod in his direction and I get to plunge my cock either down his throat or up his arse. Tell you what though, he's a dirty bugger, he's even got me to shove my fist up his arse right in up to my elbow! My eyes nearly popped out of their sockets he got me to do it. I didn't think it was humanly possible, but he's shown me otherwise on several occasions since then. So I've got myself a regular little bitch now and I couldn't be happier. Well that's not strictly true, I wonder when I'm going to hear about this volunteering business otherwise I'm going to think someone's having a laugh at my expense and I won't be very happy if that's the case" he said throwing me a menacing frown.

"Actually that's what I came to talk to you about...." I said and then spent the next twenty minutes going through the details of the selection process, the auditions, questions, tasks etc. I got him to repeat the questions and answers so that there would be no mistakes made preventing him from being a finalist. I left him lying on his bed looking like the cat that got the cream.

My final visit of the morning was to C-Wing where I bumped into Eduardo enjoying a cigarette by the main door. This made things easier for me because I invited him to join me for a short stroll round the exercise yard where I made small talk before doing the whole sales pitch on the volunteering, after only a minute or two's thought he decided he was definitely up for the challenge so I gave him all the other necessary information before leaving him to finish his second cigarette while I went off for lunch.