Diary of a prison officer : Part 1

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.

WEDNESDAY 31ST MARCH 2010

Dear Diary, today I completed the first month of my employment at HMP Ollerton and it has been just as eventful as the rest of the month. It has given me much to think about. When I first applied for the job I thought it would be a good move for me, that I would enjoy the change in my career and hopefully the job itself. That thought has proved to be a total underestimation. I now know that I have found my vocation in life, I find myself acting as a father figure for many of the inmates; sharing their up and downs, providing a firm but fair and approachable point of contact for many inmates who know they can talk to me about anything on their minds. I also suspect that my activities in the post-punishment tests have been relayed amongst them adding to the impression that I am a decent guy willing to give and receive.

But what has hit me the hardest has been the seismic shaking of my previously rock solid heterosexuality. I knew man to man sex went on but it had never occurred to me that I would ever participate in it let alone enjoy it! Now if anyone asked me how I would describe my sexuality I would have to hand on heart call myself bisexual because as things stand at this moment in time I would have a hard time saying which gender I prefer, the jury is very much out. Men and women are different having their own flavour, if you’ll excuse the expression! Anyway, I am digressing; today’s events have sealed the fate of my heterosexuality.

I will skip the bit about my day shift, it was very much business as usual and I don’t want to bore you by repeating what I’ve already described before. So straight to this evening’s events, it really started at 19:00hrs when I escorted Jarek from his cell, again he was very quiet and subdued so I did my best to lift his spirits by giving him positive affirmations and a couple of light hearted jokes. The best I could draw from him was a quirky smile and he withdrew into himself once we walked into the entrance hall of the wash area and he saw the stocks. Mick had removed the padlock and the top stock bar; he had then attached a set of hand cuffs to each of the metal rings ready for Jarek’s incarceration.

I guided Jarek to the rings in the floor and attached the cuffs to his ankles, then got him to lean forward putting his neck and wrists on to the half-circle grooves on bottom bar. Mick then swung the top bar over and then gently down onto the bottom bar ensuring that Jarek’s flesh wasn’t nipped in the process. When he was satisfied that all was okay Mick attached the padlock locking the bars into position. Jarek was now bent over at the waist, not the most dignified of positions but then it wasn’t supposed to have been. We then called Richard to let him know that we were ready for him. Ten minutes later Richard came down pulling what looked like a very large vacuum cleaner, I asked him what it was. He informed me that it was a portable colonic irrigator designed for when a shower system can’t be used.

Not needing to explain further Richard got on with the job in hand, starting by reaching into his pocket and taking out a small tub of Crisco and smearing a load of it along Jarek’s crack and pushing a wad into his anus with two fingers and spreading it all around inside his rectum and anal ring. In response to this intrusion Jarek shifted his weight around but was unable to avoid the roaming fingers and his greasing up. After a minute he gave up and accepted his fate. Once Richard was satisfied that Jarek was thoroughly greased up he turned his attention to the metal douching tube attached to the end of the machine’s flexible hose (this actually had two pipes inside). When the tube was greased he deftly inserted it into Jarek’s anus, just a little bit, maybe an inch or two. He told me to turn the motor on, which started whirring, then the pipe flexed and water started to pour into Jarek’s rectum. It continued for a couple of minutes before stopping and reversing the flow allowing the faeces and water to exit through the other pipe. Richard then pushed the tube in further and the process started all over again. This cycle was repeated until some eighteen inches of pipe had been pushed up inside and Richard was satisfied that Jarek had been thoroughly cleaned out. Richard then withdrew the piping and re-greased Jarek’s crack and arse. He then packed up the machine and wished us good luck because it was going to be a busy evening for us; the timing of this punishment had been deliberate as these two hours were the peak time for the use of the washing facilities so the greatest number of inmates would be going past.

At about 19:50 the first inmate entered the entrance hall seemingly oblivious to the announcement that had been made on Monday because he was caught by surprise by the stocks and explanatory poster. He stopped beside us and asked for an explanation, by the end of it I was not convinced by his naivety because he asked all the right questions but his attention seemed very much focused on Jarek’s body. Either way he sauntered off into the wash area for his shower. For the next twenty minutes inmates filed through, some made a point of greeting Jarek with others simply looked either at the posted or at Jarek without comment. It wasn’t 20:30 that the pace picked up with the first inmate showing interest in using Jarek’s services, it was Eduardo who having thrown me a wink walked round to the front of the stocks and told Jarek to open his mouth. True to form Jarek began to protest until he was reminded about the poster, with a loud sigh he closed his eyes and opened his mouth. Eduardo wasted no time in slipping his cock into the waiting mouth, egged on no doubt by the gathering crowd; his action seemed to break the dam of their reservation. Within a minute or two another inmate had slipped his cock into Jarek’s arse and was pumping away with great vigour (again I suspect putting on a performance for the crowd). I couldn’t help but feel sorry for Jarek, I know he was being punished for a good reason but his humiliation was total, no longer was his pride intact. Eduardo and Bert (the one doing the fucking) seemed to be working in tandem plunging in and out at the same time. For nearly five minutes they continued until Eduardo started to shudder and then ejaculated down the throat, shortly followed by Bert. Again in unison they pulled out their still dripping cocks and went back to the wash area to clean up. Their positions were immediately filled by the next waiting participant who set about relieving their own needs with gusto.

I suppose this continued for the next half an hour until the imposing figure of Tyler made his entrance. His booming voice stilled the others into silence when he announced that it was his turn to partake of Jarek’s love tunnel, the guys stepped aside including the inmate who was already inside Jarek! Tyler was clearly turned on by the whole scene for his enormous cock was rock hard and standing upright. Standing behind Jarek he pulled his cheeks apart and from where I was standing I could see that his hole was getting very loose and sloppy from all the fucking it had received and jism was slowly dripping from his slightly puffy lips. Satisfied with what he saw Tyler aimed his cock at the hole and in one smooth thrust expertly inserted it halfway in. Jarek groaned in reaction and tried without success (because Tyler was holding him securely by the hips) to move away in an attempt to avoid the impalement. Then adjusting his position slightly Tyler continued to slowly push until his cock was fully buried up to the hilt. Remaining stationery for a moment he allowed Jarek to get accustomed to him before he started the fucking in earnest, slowly at first but gathering momentum all the time until he was really hammering away. On and on he went, Jarek was moaning in time to the thrusts, whether it was from pleasure or pain was impossible to tell but it didn’t matter he was getting fucked and that was that. With a loud cry Tyler bucked and shuddered before collapsing on top of Jarek having shot load after load of jism deep inside him. When he pulled out there was a squelchy plop and an audible gasp from the audience as the hole recently vacated seemed unable to close up, I could see deep inside him and now I understood the term “tunnel of love”.

If I had thought that was horny what followed blew my mind! Following Tyler was Gus, as cocky as ever; he knelt down, facing towards us, between Jarek’s legs and took his semi-flaccid cock in his mouth and started to give him an expert blow job. Then quite casually he reached up with one hand exploring along his crack until his fingers found the sloppy hole, finding their target they honed in on it. The finger tips disappeared straight away and then up to the second knuckle with ease. Four fingers were now fully inserted up to the palm and Gus used them to fuck Jarek in time to the blowjob. Almost imperceptibly he started to tuck his thumb in behind the fingers (I knew what was coming next) without missing a stroke. Any resistance from Jarek’s ring was disappearing fast and before we knew it Gus had inserted his whole hand and was gently fist fucking the hole. Abruptly a muffled cry (due to a cock already being in his mouth) came from Jarek and Gus enthusiastically swallowed the whole load of jism, except for a small trickle from the side of his lips. When Gus had finished sucking him dry and the cock had shrivelled to its normal state he gently withdrew his fist and took his time massaging and stroking the stretched anal ring until it had almost closed up again. Standing up he bowed to the stunned audience before slapping Jarek’s arse and disappearing into the wash area.

There was just half an hour left of his punishment period and the tempo slowed considerably, Jarek gave a further four blow jobs and received one more fisting – from me! I just couldn’t resist it. Liam’s words about me being a natural fister were echoing in my ears. As my hand slipped inside his rectum, I savoured the resistance giving way and the smooth slide into the enveloping silky warmth. I gave him a firm but steady fisting to loosen him up, then, a thought occurred to me which I brought to life immediately. Stepping up close using my free hand I guided my cock in beside my wrist and as it slid in I held it in my hand before fucking him until I orgasmed. After I had withdrawn and cleaned myself up it was time to release Jarek from the stocks and let him wash himself off in the showers. He walked away very stiffly in a slight daze, after all two hours is a long time to be bent over in the stocks especially when getting stuffed from both ends! Mick and I were still clearing up when he returned from the showers looking a lot fresher than before but he was unable to meet our gaze and quickly disappeared back to his cell.

Finally my shift was over and I was able to make my way home to a readymade meal care of my microwave and a cold can of beer from the fridge in front of the TV. Thinking back over the last month’s events all I can think of is how much I have enjoyed and learned from the journey I have been on. I can’t help but wonder what next month will bring!

I very much hope you have enjoyed my story and I would welcome any feedback. Please email me at: jaypbee at fsmail dot net Thanks.