Diary of a Prison Officer Ch. 01

So I spent the next half an hour massaging the ring and gradually increasing the number of fingers that I could insert from one, to two, then three and finally four. Gus was panting and sweating, his upper torso was flushed but at no time did he ask me to stop. So at long last I was ready to tuck my thumb behind the fingers and telling Gus to brace himself I started the final push. The resistance was great but slowly ever so slowly it gave way and with a growling groan from Gus the ring gave way and my fist slid past it and into his bowels. I carried on pushing and again my hand inched its way up inside Gus, by now three quarters of my forearm had disappeared. We must have forgotten that time was passing, Adrian was transfixed by the spectacle unfolding before him; so much so that he hadn't noticed that it was now 11.00am and time for the next inmate to arrive, until that is there was a knock on the door. All three of us instantly froze and held our breaths.

The door slowly opened and in walked Sayeed, the expression on his face was priceless. He had been looking down as he came in and looked behind him as he closed the door. Then he turned round and saw my arm buried deep inside Gus and Adrian looking on in awe. His mouth dropped open and he flushed a bright red clearly embarrassed by what he saw. Adrian looked away and back to his paperwork. I half turned and smiled and putting as much calmness into my voice as I could, I asked him to take a seat and we would be with him in a minute. He stammered an okay and sat down on the chair indicated. I did however notice that again his cock was slowly swelling between his outspread thighs.

Gus was getting restless so taking the hint I gently pulled my arm back, his anus gripped my arm almost lovingly as it exited. Again there was resistance from the inner ring but with patience it released my hand and the rest of my exit was a lot easier. My hand finally reappeared with a wet sloppy squelch, poor Gus collapsed in a heap with a quiet groan and a hole that still hadn't closed properly. Using a handful of tissues I gently wiped his cheeks, crack and hole clean, the tickling sensation produced by the paper caused his ring to clamp shut tight again. I then wiped my forearm clean and removed my soiled gloves. Anyone walking in now would never guess what had just happened.

When Gus had recovered he climbed off the couch and stood facing us with hands clasped behind his back as cocky now as when he had first walked into the room. Conscious of the over running of the session Adrian wasted no time in telling Gus that he was free to collect his box of possessions and get dressed again. I watched him step into his clothes and as his pert little bum disappear into his pants and then jeans I still could not believe I had been so far up inside him, part of me was wishing I could still be there or at least for a replay. Who knows one day perhaps.....

As Gus shut the door behind him we turned our attention to Sayeed who by now was getting a little restless, any sign of arousal had disappeared with his cock hanging flaccidly over his balls between his legs. As I donned another pair of latex gloves Adrian asked him the routine questions.

"Sorry to have kept you waiting Sayeed, hope you didn't find the show too shocking."

"Umm, it's not something I've ever seen before or thought humanly possible. I do hope that you're not going to try anything like that on me!"

"It's not on our agenda but we would seriously consider your request should you change your mind" Adrian replied with a chuckle.

"Definitely not!" came Sayeed's emphatic reply.

"Okay Sayeed back to the task at hand, I have some routine questions to ask you. Outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Straight"

"Have you ever had sex with a man?"

"Only On the odd occasion. When my needs have been too great to be resisted any longer."

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

"Oral several times, my cell mate gave me a blow job each time. Anal only once, in the showers late one night, a guy there begged me to fuck him, so I did."

"Okay, final question, when was the last time you ejaculated?"

"Last week in my cell, I gave myself a hand job."

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

"None of your funny business now, I've told you the truth to your very personal questions, so why do you need to do these tests?"

I beckoned him over to where I sat and informed him that these tests were to complete his medical records and for no other purpose, no other inmate has refused so far nor has anything been done against their wishes. Sayeed still seemed a little reluctant but chose to say nothing before walking over to me and standing in front of me with his hands crossed in front of him with a frown on his face as he looked down at me. I reached out and gently cupped his balls which in my mind felt heavy and possibly a little tender from the way he responded to my manipulation of them.

"I get the distinct impression Sayeed that you are suffering from a term we call Blue Balls i.e. too much semen stored in your balls caused by lack of release resulting in aching and soreness. Am I correct?"

"Yes Sir, they are indeed tender."

"I would recommend that you release it as soon as possible but first I need to complete the final test. Please turn round, bend over at the waist and grasp your knees." I said in the most doctor-like voice I could muster.

"Is this absolutely necessary?"

"Yes."

"Well, I suppose so but I have a proposition to offer you."

"Go on, what do you have in mind?"

"I really don't want you anywhere near my back door. However I will let you do what you want on condition that when you have finished I can do what I want to do?"

"Mmm. What do you think Adrian?" I asked looking in his direction.

He simply shrugged his shoulders before saying "We need to complete the tests so why not? I can't see what harm it will do and it will get Sayeed's co-operation."

"Okay, you have yourself a deal" I said returning to face Sayeed "now please turn round and bend over."

Smiling gently to himself he did as he was told, as he grabbed his knees he clenched and released his cheeks a couple of times before relaxing and giving me a clear view of his hairy crack. I located his anus nestling amongst the black hairs, it was pinkly glistening and really quite appealing in its obvious tightness. I unintentionally licked my lips before I applied a large glob of KY to the hole and smeared it round with my index finger before applying a little pressure and pushing inside up to the first knuckle. It was tight, but not as tight as Jarek's had been. So I left the finger there for a couple of seconds for the ring to adjust to the intrusion before pushing in a little further. After further massaging and applying pressure I managed to fully insert my deep inside him bringing a stifled groan from his lips.

All the time I was feeling around inside seeking his prostrate he was clamping down hard on my finger, I had to tell him to relax otherwise he would chop my finger off! Finally I found it and was satisfied that it was normal so I slowly withdrew my finger and wiped it clean. I told Sayeed that he could stand up the test was over, I was satisfied with the results, they agreed with his statement.

"Of course they do, I was telling you the truth, I am an honourable man and never lie. Now we had a deal, are you going to be as honourable as me Sir?" Sayeed said looking at me with a new found confidence.

I must admit I was a little taken aback by his statement and simply replied "Of course, we had a deal, you've kept your end of the bargain so why wouldn't I? Now what was it you had in mind?"

"First of all I want you to remove your clothes and then kneel down in front of me."

I didn't need to ask what he had in mind having been in a similar position before! I glanced over at Adrian who simply raised his eyebrows and gave a quirky smile in encouragement. There was nothing for it but to keep the promise so looking Sayeed back in the eye I slowly and confidently stripped off my uniform placing each item on my chair neatly folded. First the jacket, then the shirt, next my shoes and socks, then my trousers leaving just my boxers shorts to go; then with a faint smile on my face I pushed them down and stepped out of them and placed them with the rest of my clothes. Now fully naked I knelt down in front of him as instructed and looked up at him for the next instruction.

He didn't say a word; he simply held his erect cock in his left hand and guided my head with his right hand until my lips met his cockhead. The first thing I noticed was the smell; he certainly wasn't as fresh as Tyler had been. I guess he hadn't washed since the previous evening as it had a distinctly prawn-like smell but thankfully there was no sign of any smegma, I would have heaved my guts up if there had been! Instinctively I opened my lips and licked them with my tongue to wet them, just in time as his cock was shoved inside. I felt both hands grip my head; unlike Tyler he showed no consideration for me, as he thrust his cock straight to the back of my mouth and down my throat. I gagged reflexively but just managed to stop myself from being sick and then concentrated on breathing in time with his thrusts. I expected him to keep going until he shot his load but he obviously had other plans as he abruptly pulled his cock out of my mouth and told me to stand up.

Confused I did as I was told and asked "What's wrong?"

"Nothing is wrong." He replied very seriously, then, he cracked a smile and chuckled "You're doing very well, much better than I anticipated actually. But it's time to take it to the next stage and it's going to be even better. Have you been fucked before?"

My face blanched and I stammered "N-n-no. Is this really necessary?"

"Excellent!" He replied "A virgin hole! Just what I like! Yes it is necessary, this way you'll know the joy of having my cock from both ends. What could be nicer?"

A lot of things I thought to myself but wisely kept these thoughts to myself.

"Walk over to the couch, bend over and spread your legs wide."

I did as I was told and prayed to god that it wouldn't hurt as much I imagined it might. Just as I was thinking this I felt two hands grasp my cheeks and pull them firmly apart allowing cool air to waft down my crack; then before I could react a hot wet tongue made contact with my anus. It surprised me to say the least then I felt the tongue lap all round my hole and flicked in and out coating it lavishly with saliva, despite myself I moaned in reaction to the pleasurable sensations I was experiencing and began to back onto the tongue. This seemed to go on forever but was probably only a couple of minutes in reality and then it was gone. In its place was something much bigger, much, much, bigger in fact it felt enormous! Looking over my shoulder in alarm I saw Sayeed carefully guiding his erect cock between my cheeks and pushing against my back door. From the glistening appearance of the cock I guessed that he had lubricated the whole length of it. Seeing me watching Sayeed smiled and told me to relax, the more I relaxed the less it would hurt and the more I would enjoy it. Unable to think of anything worthwhile to say in response I looked away and closed my eyes to concentrate on relaxing as best as I could. The pressure was gradually building and eventually my ring stretched and gave way and allowing his cockhead to slide in. Aargh! I cried out at the intrusion, it felt enormous as my ring clamped shut around his shaft; all I wanted to do was get it out straight away. I tried to pull away but Sayeed had taken hold of my hips and leant all his weight on me effectively pinning me down and preventing me from moving. He remained motionless for a couple of minutes and slowly the pain subsided as I became accustomed to its presence, then I felt it move further up inside me and continue until I felt his thighs pushing against my outspread legs and his balls gently slap against mine. I had never felt so full inside and despite myself it began to feel strangely good.

Then the fucking started in earnest! Pain erupted through me again but quickly died down as it had come, in its place was an intense sensation, impossible to describe, with each thrust my cock pulsed and expanded until it was rock hard. Harder and harder, quicker and quicker he banged into me, until I could bear it no longer and with a load groan my cock exploded shooting jism out trapped between my stomach and the plastic couch cover. Sayeed was oblivious to all of this for he kept hammering away until he started to shudder and then with a growl he convulsed and shot his load deep inside me before collapsing on top of me. I could feel his hairy chest scratch my back and his hot panting breath on the nape of my neck. After a few minutes I felt him shift his weight and then push himself up, in doing so his shrunken juice covered cock slid out of my sloppy hole and I felt strangely empty.

"Thank you Sir, if you don't mind me saying you have one hot hole, it's a shame you're not a poof coz I could shag you every day and for me being a straight guy that is a big thing."

Standing up myself I gingerly touched my aching hole and said "Uh, thanks I think. That is everything now isn't it?"

"Yes Sir."

"Good. Well, in that case you're free to collect your belongings and return to your cell." Adrian informed him.

Having cleaned myself and the couch up I got dressed and watched Sayeed leave the room with a distinctly smug expression on his face.

Adrian turned towards me and said "That went rather well didn't it?"

"I wouldn't say it went quite as I expected! But I have had worse days I must admit."

That dear diary was the last of the excitement for that day, thankfully. The rest of the day was business as usual although I did walk rather stiffly for the rest of the day, can't think why can you? Oh and I found out that what goes up must come down. Yup, when I got home I found that my shorts had been soiled from all the spunk that had leaked out, yuk!

Needless to say that later that night down at the Kings Head with Mike and Tom I forgot to mention my sexual exploits, I really don't think they would have understood.....

MONDAY 29TH MARCH 2010

After a quiet weekend spent catching up with household chores, food shopping and then spending quality time watching Sky Sports and several cans of beer it was back to work.

As soon as I walked on to E-Wing I could tell something was up, many inmates seemed agitated and others withdrawn. I asked Mick (fellow prison officer) what was going on as we did our rounds checking the cells and inmates. He said that late last night things had kicked off between Jarek and Vince, a newcomer to the ward. Vince was a nasty bit of work and had taken an instant dislike to Jarek. He started shouting xenophobic insults across the wing and then went on to shout homophobic insults based on what he had been told by other inmates who had witnessed Jarek's punishment in the chapel. Jarek naturally took exception to this and waded in with his fists to put Vince in his place, which he did to great effect. The two men had fought like wild animals and by the time Jarek had beaten Vince into submission the wing had been trashed and most inmates had run for cover, except for a few that had been egging them on. The prison staff arrived just as Jarek was dealing his last punch to Vince's very bloody head, who then crumpled into an unconscious heap. Jarek was immediately overpowered and frogmarched into solitary confinement and checked over by the medical staff. Satisfied that he was okay they left him alone and turned their attention to Vince who was still unconscious. He was carried to the hospital wing where he was kept under close supervision until he regained consciousness and early this morning was fit enough to be returned to his cell. Jarek was still in solitary confinement waiting for his visit from the Governor.

I didn't see Jarek until later that afternoon; he was looking a little worse for wear with bruises beginning to appear all over his face and naked body. He carried himself with pride and confidence because he had won the fight and was still top dog on the wing regardless of the price he would no doubt have to pay for the fight.

And there was indeed a price to pay, which came as no surprise for anyone least of all Jarek. Liam walked onto the wing late in the afternoon and announced that Jarek will be punished on Wednesday 31st March 2010 in the stocks sited at the entrance to the wash area for two hours between 20:00hrs and 22:00hrs. There was little reaction to this announcement on the surface, but underneath there was a quiet buzz and word would no doubt get round very fast.

When he had finished talking to the inmates Liam spoke to Mick and myself asking us if we would volunteer to oversee the punishment and maintain order with overtime being paid. We confirmed we would, for myself I was more than a little curious to see what would be involved during the punishment.

TUESDAY 30TH MARCH 2010

After the morning round I was called to the wash area where Mick and Dave were already waiting for me. We had the delightful task of erecting the heavy wooden stocks, which took us the rest of the morning to do simply because of the weight of the components and the lack of instructions! When it was finally complete boy did it look imposing, I sure wouldn't want to be incarcerated in it for it had all the appearance of a medieval instrument of torture. Physically it was situated in the centre of the entrance hall of the wash area so you could hardly miss it but it was easy to walk round when not in use, apparently it was going to be sited there permanently as a constant reminder to the inmates of the ultimate punishment. It had two sturdy legs at either end of a horizontal bar, on top of which sat another bar attached by a huge hinge at one end and secured by a padlock at the other. In the middle of the bar was a hole cut approximately six inches in diameter and either side was another hole about three inches in diameter. These were where the neck and wrists of the inmate would be secured to prevent their escape. Set in the floor about three feet behind the stocks were metal rings where the inmate's ankles could be secured further reducing their range of movement. I was getting quite turned on by the thought of Jarek being placed in the stocks and several times I had to adjust my trousers discreetly as a result.

On the wash area notice board we put up a large A3 poster announcing the first ever punishment by stocks tomorrow evening at 20:00hrs with Jarek being the first participant. Inmates will be able to participate in whatever activity they wish but physical injury will not be permitted under any circumstances.

Within an hour word had gone round the whole prison and there was a constant stream of inmates to read the notice board and examine the wooden stocks. The whole prison was buzzing with excitement, except that is for Jarek who managed to combine a look of being major pissed off, total resignation and a determination to maintain control of his wing. Oh, and as for Vince, he was keeping a very low profile. He knew that he was responsible for Jarek's coming punishment and was worried what the payback would be afterwards. Not only that he had a problem of his own; while he had been unconscious in the hospital wing his punishment for starting the fight had been meted out. He had had his clothes removed leaving only the sheets to cover his modesty. Unknown to him he had also had his cell stripped of all belongings as was now the routine, no one took much notice any more except for the inmate involved. When Vince had recovered from his beating he was escorted back to his cell amidst vocal protests about his lack of clothing which did not go down well with the other inmates. They told him to grow up, he had been man enough to start a fight so he should be a man enough to take the punishment; at least he wouldn't be in the stocks tomorrow night. He seemed to realise that he was on dodgy ground so kept his head down for the rest of the day doing his best to avoid Jarek.