Diary of a Prison Officer Ch. 02

"It's fine by me, as I've already told Jason I run a relaxed house here so wear what you please or not as the case may be. Just do whatever you feel comfortable with" I said.

"You're cooler than dad you know." Aaron called out on the way to the bathroom.

"Really? I always thought Tom was a laid back guy." I said to Jason who by now was sprawled out in my arm chair.

He must be comfortable in my presence I thought to myself because the position he has assumed leaves him totally open to view and he must know this. While the towel was still wrapped round his waist, one leg was draped over an arm and the other was lying straight ahead. His balls hung low almost touching the seat with his cock draped over one thigh held in place by the towel.

"He is, except when it comes to matters of the human body or sex, then he gets all prudish big time" he replied.

"Oh ok." Was all I said as I distracted myself with preparing lunch and drinks.

By the time I had finished laying up the table Aaron had returned wearing a towel wrapped tightly round his waist and walked over to the window commenting on the views I have from the flat.

"As you're back now, I'm just going to have my shower. I'll be back in five."

Nearer ten minutes later I walked back into the room feeling refreshed and a lot more fragrant! Deciding to be one of the lads I also wore just a towel, after all I have to live up to the rules I had set out.

Sitting round the table, lunch was a relaxed affair, the main topic of conversation being Aaron's wedding, honeymoon and how they had been getting since their baby had been born two weeks earlier than expected. I wondered if Aaron's keenness for the keep fit was to get some 'me time' away from mum and baby. I kept this thought firmly to myself.

Two hours later I had my flat back to myself having arranged to meet them on Thursday evening for the next jogging session. I spent the rest of the day trying to get the image of Jason sprawled out in my chair out of my mind, it was a task I found very difficult!

TUESDAY 6TH APRIL 2010

First day back on the shop floor, so to speak, and it was all systems go from beginning to end. As ever we did hand over first catching up on events over the bank holiday weekend. It seems that on the whole the prison was quiet with the inmates being calmer; it might just be something to do with the fact that a large number of them had shot their loads either inside Jarek or over the shower floor. The only person who hadn't calmed down was Jarek, after spending most of Friday and Saturday inside his cell he had finally surfaced and kept asking when I was back on duty.

Despite being offered assistance by the other prison officers he wouldn't talk to them, insisting that he only wanted to talk to me. Flattering I'm sure, but I was a little apprehensive about what a previously angry young man wanted to say to me who's just been publicly fucked and fisted for two hours. Well he would just have to wait until the prison wing rounds had been completed.

Finally mid-morning I walked onto E-Wing with George and we went from cell to cell checking in on the inmates, I didn't see any sign of Jarek until I walked into his cell. He was lying sprawled out on his bed, naked obviously because this was now his permanent state of affairs, reading a girly magazine. He was surprised by our sudden arrival and looked distinctly uncomfortable.

"Come on Jarek, look lively" George boomed out "you know you have to stand to attention when your room is being checked."

"Er, do I have to Sir?" Jarek responded, flushed with embarrassment.

"Yes" was our simple answer.

Reluctantly he closed his magazine, climbed off his bed and stood up straight. The reason for his reluctance was obvious; he had a hard on which he was doing his best to cover up with his hands. Being the considerate people we are we chose to ignore this fact and proceeded to inspect his room. Once we were finished I turned to Jarek and asked him what he wanted to talk to me about.

"It's embarrassing Sir, is there anywhere I can talk to you in private?" Jarek asked.

"What's wrong with talking here?" I responded.

"Well, I need your advice and I want to show you something of a personal nature. You've been straight talking with me and I will trust what you say."

"Okay, let me finish the morning rounds, I'll then be back and we can talk in private in one of the interview rooms."

"Thanks Sir"

With that George and I resumed our rounds which we completed without further incident. Before I collected Jarek I cleared it with Max to make sure that it was okay to use one of the medical interview rooms. His response was positive and appeared pleased that I had gained the confidence of a previously troublesome inmate, I was free to use any room that Richard wasn't planning to use.

With the formalities over with I went over to E-Wing and escorted Jarek back to the main building and into one of the spare interview rooms. My impression of him was although he was still clearly a force to be reckoned with judging by the other inmates' reactions, the angry fire burning in his eyes I had seen previously had gone. In its place was a concerned expression and just possibly a little bit of maturity.

Closing the door behind me I gestured for him to sit on the examination couch while I pulled up a chair and sat down opposite him assuming as relaxed a posture as possible.

"Right Jarek, how can I help you?"

Jarek made no immediate reply. He sat on the edge of the couch, legs slightly spread with his hands gripping his knees and feet gently swinging backwards and forwards. He studied his feet intently for a minute or two before looking up at me.

"I've been doing a lot of thinking over the last few days, okay since my night in the stocks, and I have some questions I want answers to but I don't know where to look for them or who to ask."

"Well" I answered slowly. "How about asking me any question you might have. If I have the answer I will be honest with you, if not then I will investigate and come back to you. How does that sound?"

"Okay, I guess. The first question I have is; my girlfriend, Marita, has a visiting order and wants to see me but how can I let her see me like this? She will want to know why I'm naked while the other inmates are clothed. What am I supposed to tell her and how far do I go with the explanation?"

"I think you will find that when members of the public visit you will be provided with suitable clothing. In fact I am sure management have bought in specially designed boiler suits for inmates who have been permanently prohibited from having personal possessions. That way she'll be none the wiser and you won't have to tell her anything, unless you want to that is." I advised him.

"In what way are they special?"

"They are all in one and don't have any pockets into which items can be smuggled, if you catch my drift."

"Yeah yeah" Jarek sighed. "My next question is, after my night in the stocks, is that quits? When do I get my clothes back?"

"That's an easy question Jarek. You won't be getting your clothing back until the end of your prison sentence. You know from the rules. You lost the right to have clothing after your second infringement; you went on to commit two other infringements resulting in the stocks. The only time you will have any clothing will be for visitors."

"Mmm, shit. I thought that might be the answer." Jarek said scowling.

"How have you adjusted to being naked?" I asked, trying to get him to open up and express his inner feelings.

"At first I hated it, found it degrading and felt that everyone was laughing at me. It made me feel very angry and I wanted to fight anyone who reacted in any way to my nakedness. It is only during this weekend I have come to realise that it is only myself I have to blame for my predicament. I was given enough warnings and I chose to ignore them in my pride and bravado. Having been in the stocks and endured what I had to endure, my nakedness seems less significant now and something I am beginning to accept. To be honest I have other things on my mind."

"What things are those?" I asked becoming curious as to what those might be.

"During Thursday and Friday last week my arse and throat were very painful, I didn't want to eat or use the toilet it was that bad."

"Did you notice any bleeding?" I was now getting concerned.

"Not that I saw, if I had I would have called for the doctor straight away I can tell you. But by Saturday things were getting back to normal and Sunday everything was fine except for one thing."

"And what is that?"

"My turds are now like horse dollops and I'm sure my arsehole is bigger than it was before. I want you to check it for me to make sure that it is still in working order. I know I got fucked up the arse that night and I know some of the guys are pretty big but I've never heard of a guy's arse stretching so much just from being fucked!"

Well I had to smile to myself, he didn't have a clue that he had been fisted at all, no wonder he was surprised by the looseness of his hole!

"Regarding the size of your turds, it's probably a side effect of the stretching your rectum and anus recently experienced. As long as there's no bleeding when you go to the toilet then I wouldn't worry about it, you may find that they will shrink in size as your hole tightens up again. Have you tried pelvic floor exercises?" I asked trying to maintain a serious and concerned demeanour.

"I don't even know what they are" he replied, "nor do I know if my hole's working properly. Will you check it out for me please?"

"If that's what you want, then sure. Okay, let's do it. If you would please climb up on the couch, get on all fours with your head resting on your hands. While you do that I will get prepared."

"Yes Sir" was all he said in response.

Turning round I opened desk drawer and retrieved a box of latex gloves and a small can of Crisco. Slipping on a pair of gloves I opened the can of Crisco and turned back towards the couch to find that Jarek had obeyed my instructions and assumed the required position.

"Okay Jarek, I would like you to help me here. Please reach behind you and using both hands pull your cheeks apart, you may need to spread your legs a little to stabilise your position. It will make it easier for me to assess your hole."

Jarek made no comment but did as he was asked. It was a sight to behold, he arse cheeks glowed white under the harsh lighting. His balls swung freely and like his crack were virtually hairless. His cock was flaccid and diminutive in size; clearly he wasn't finding the situation erotic. I stepped up to the couch and took a closer look at his anus. It didn't take an expert to see that it had seen a lot of action! The hole was fully closed but the puckered skin was distinctly pink and enlarged.

I took a small glob of Crisco and smeared it all round the rim, already I could feel that the muscle tone was laxer than would normally be expected.

"Please try and relax, I'm about to assess your anus's elasticity. I will be as gentle as I can, let me know if it gets painful or uncomfortable." I said as I started to insert my index finger, up to the first knuckle to start off with.

Getting no response from Jarek or resistance from his ring I slowly and gently inserted the whole finger until it could go no further.

"How does that feel? Any discomfort?" I asked.

"Fine, no discomfort at all" came the calm reply.

I withdrew my finger and then introduced a second finger and inserted both fully with virtually no resistance; however I did notice he shifted his weight a little. Again I asked the same question and got the same answer, so I withdrew the two fingers and introduced a third having applied some more Crisco to his slightly open hole. As I pushed the three fingers in up to the hilt I saw him shift around again, not saying anything with my free hand I felt between his legs and found that his balls had tightened and his cock was now a raging hard on! Deciding he was enjoying it so far I took it to the next level. Again I withdrew the three fingers and started to introduce the fourth.

As a method of distraction I said "I am very impressed with you Jarek, your whole attitude turnaround is remarkable considering what you were like when we had our first encounter in the Governor's office." All the time I was slowly pushing the fingers in deeper and deeper.

"What do you mean?" Came a slightly breathless reply.

"Well, for a start you were very unhappy with the thought of another man simply touching you let alone having anything as intrusive as this done. Today you seem very relaxed and are taking it in your stride. What's brought about this change in you?"

By now all four fingers were in as far they could go, I let them rest there for a minute so he could adjust to the intrusion.

"I dunno really. As you say at the beginning I found the very idea repulsive and against everything I have ever been taught. But having spoken to other guys and experienced things I didn't think possible my viewpoint has slowly shifted. What has surprised me the most is that some on the experiences are pleasurable, even this one I guess. Does this make me gay? Because I still fancy and miss Marita like crazy."

I withdrew the fingers and noted that the hole was slow to close; I smeared some more Crisco round the hole and plenty on the whole of my fist up to the wrist. In for a penny, in for a pound I thought to myself. I coned my fingers and thumb then gently started to push them inside. Again to keep up the distraction I hesitated as the fingers started to enter his hole before replying.

"I'm glad you're finding this pleasurable and I am close to letting you know the findings of my assessment. No, I don't think it makes you gay at all, simply more in tune with your body. I think it's important that you keep Marita close to your heart because you will need her when you are released. Now, tell me, are you feeling any discomfort?"

By now my hand was in up to the widest part of the hand, I stopped pushing while I awaited his answer and again to allow for its accommodation.

"Umm, only a little, a bit like near the end of my time in the stocks. It doesn't hurt, I just feel full. Yeah that's it, like when you're bursting for a dump. I think I'm about to shoot my load any time soon. How many fingers have you got inside? I've lost count while we've been talking."

As he asked this question, his ring gave up its slight resistance and the whole of my hand slid smoothly inside until it was buried up to the wrist.

"Aaaaaargh! I'm cumming! Eeeeeergh!"

Jarek's cock shot three large globs of spunk over the couch, all the time his ring spasmed and gripped my wrist tightly. His body shook several times and then he slumped forward until he was lying flat on the couch. As my wrist was still being firmly gripped I had no choice but to go with him, finally the anal spasming eased off and so did his grip. Pulling my hand out slowly it exited with a quiet plop leaving a ruined hole behind. I unpeeled the gloves and threw them into the bin and wiped my wrists clean of a little bit Crisco and juice, then sat back down in the chair to wait for Jarek to come round from his dazed state.

After a minute or two he lifted his head and looked at me with slightly glazed eyes.

"Jeez, I haven't experienced an orgasm like that since the night in the stocks! Sorry about the mess Sir. Have you come to a conclusion about my hole and exactly how many fingers did you have up me? Was it two or three?"

"Hey, don't worry about making a mess" I replied "the couch cover can be washed later. I'm glad you enjoyed the experience, like I said before it's a real turn around as far as I'm concerned. In answer to your question, yes I have the results of my assessment and what can be done about it. As to how many fingers I used, it was more than three; in fact I was able to insert the whole hand."

"What do you mean your whole hand? That's not possible! Are you really saying that you've been able to fist me? I've seen it done in a couple of blue movies but I always thought it was fake. Tell me you are kidding me, right?" Jarek fired at me all animated now.

"No I'm being completely serious. By the description you gave me towards the end of the assessment I strongly suspect that you were fisted during your time in the stocks, which is why your arse was so sore afterwards. Clearly no permanent damage has been done although there are obvious side effects which may be a good thing or not depending on your view point. There are a couple of exercises to tighten your anal ring if you wish or you can leave it as it is to allow easier entry in the future."

"I'm sorry Sir, but I really don't believe what you're saying is possible. It would surely have hurt me if you had; all I felt just now was a little discomfort but nothing more, then an incredible fullness before I orgasmed."

"Okay. I hear what you say but I have been honest with you. I'm going to ask you to do something, will you trust me? If you do as I say then you will have your proof."

"Yes Sir, of course I trust you."

"Right, get up on your knees facing away from me and put one of your hands behind your back." I instructed him.

Once he was in position I took hold of his hand and covered it liberally with Crisco, then brought his hand down to his crack, he had to twist slightly to do this but not very much.

"Next I want you to concentrate solely on the sensations received from your fingers, keep your anus relaxed at all times."

"Okay." Was all he said.

I coned his fingers for him and guided them towards his open hole and pushed them in until his first knuckles had disappeared.

"Now keep pushing your fingers in until you meet any resistance."

Looking at his hand I doubted if there would be any resistance as his hand was smaller than mine, sure enough, in less than a minute his hand had disappeared from sight up his rectum. He looked over his shoulder with a startled expression on his face, I noticed with a grin his other hand was at the front and was making jerking movements.

Within a few minutes his body was jerking and crying out he orgasmed for a second time. Once he had finished he pulled his hand out of his backside leaving a hole very slow to close. Grabbing a large wad of tissues I helped him clean himself all over until he was gleaming clean once more. His expression was hard to define; partly of satiation and partly of amazement.

"I believe you Sir, I apologise for having doubted you. Fuck, I can't believe how good that feels! I don't suppose there's any chance I could try it out on you is there?"

"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."