Diary of a prison officer : Part 2

Standing up straight I thanked Richard for his assistance and asked who wanted to go first. As no one volunteered straight away I randomly selected Eduardo and asked him to take my place in the shower area and assume the same position that I had a few minutes ago. I knelt down behind him and savoured the view of his glowing white cheeks in contrast to his brown back and legs, as he pulled his cheeks apart his ring glistened pinkly and opened very slightly. I took the tub of Crisco from Richard, placed it on the floor before smearing a glob of it around his ring and just inside, when I was satisfied he was greased up sufficiently I took the douching tube, greased that up and inserted it into Eduardo’s rectum drawing a quiet groan from his lips. As water flowed into him I gently massaged his ever increasingly bloated stomach, explaining what I was doing all the while, then when he could take no more I pulled the tube out and let him sit down on the toilet to release the water. The force in which it flew out made us all laugh releasing some of the tension in the room. Then it was time for Eduardo to assume the position again and the process was repeated for another two times before the effluent ran clear from his backside.

Deciding it was best to take charge I didn’t ask for a volunteer, instead I selected Dinesh, Jarek and Gus in that order because I knew that they had to be familiar with the process as they could all accommodate fists and there was no way to be able to do this without being cleaned out first. Sure enough they took the cleaning out in their stride and were comfortable enough with it to crack a couple of jokes with the other guys while it was going on. Then it was Tony’s turn and he was the last of the easy ones, all the remaining guys had only ever had a finger up their bums!

That was about to change, starting with Sayeed, I had a score to settle with him and he was going to be a tough one to crack. But crack he did, having seen five guys before him being cleaned out with no difficulty pride would not let him back away from this challenge. So after I crooked a finger at him as Tony rejoined the crowd he assumed the required position and obediently spread his cheeks wide. Once again I was given the treat of seeing his tight pink anus nestling amongst the black hairs of his crack. Not giving him time to react I started to grease up his hole with a generous amount of Crisco, I took my time in doing so savouring the chance to get my fingers up his arse. Slowly but surely his resistance broke down and I was just able to insert two fingers into his virgin hole, after some more warming up and words of encouragement he was sufficiently relaxed to be able to comfortably accommodate the two fingers. Deciding he was loose enough I inserted the douching tube, I made sure that there was enough of the tube up there that he knew what it felt like to have a cock inside him. He was panting from the exertion and I could see that his face was flushed as well as his neck and shoulders. Reaching underneath him, I accidentally brushed against his genitals and was surprised to find that he was erect, considering his attitude during his post punishment meeting this was not the reaction I had been expecting. However I kept my thoughts to myself and concentrated on the task at hand which was to massage his expanding stomach. All too soon he was fully loaded with water and I allowed him to empty himself out into the toilet under the watchful gaze of the other guys and the cameras. As with the preceding guys I cleaned him out a further couple of times before releasing him for his ordeal.

Flick and Tyler were next and just like Sayeed were anal virgins so they took some breaking into! With Tyler he was definitely a crowd puller (possibly because of his reputation) and when the douching tube was pushed inside more than one guy clapped and whistled. Flick was a different matter, he was more concerned with image and once he realised that he wasn’t about to lose face he readily submitted to the anal intrusion. Of the four remaining guys Bert, Darren, Carl and Martin only Bert seemed to show any reluctance in being cleaned out and he deliberately hung back until last. From my point of view it was game up for him, he had been the only one of the twelve guys to show any hesitation or reluctance, but that would be for the audience outside to decide not me, management no longer had a say in the matter.

Finally some two hours after entering the training room all twelve contestants had been cleaned out, allowed to don their uniforms again and were standing up on stage waiting for the results of the voting. I had to give the contestants credit, they all walked back up the aisle with heads held high and when other inmates called out to them they waved back in response with grins on their faces. They gave no sign of any tension as they waited for the votes to be counted. After five minutes of waiting with baited breath Liam handed me an envelope, I opened it with great ceremony and read out the one word written on the paper within the envelope – Bert. There was deliberately no indication of the number of votes he had got, it was sufficient for him to know that he was no longer in the competition. After a short thank you speech by Bert he removed the beret and leather belt and handed it to me as he was required to do. He stood there expectantly waiting for his clothes to be returned. I informed him that all the contestants clothing had been confiscated as soon as the training session had commenced and was locked away within the Governor’s office for safekeeping. Unfortunately this meant he would not be able to gain access to his clothes until tomorrow morning when the offices were open again. In the meantime he would have to remain naked until then. Consider it a booby prize for being voted off I suggested with just a trace of a smile. There was nothing he could do except shrug his shoulders and leave the stage with as much dignity as he could muster to the applause of the audience. As he left the room I closed the meeting by confirming once again that the next round would take place at the same time tomorrow here in the chapel where things will be taken to the next level.

I didn’t get home until late that evening and as I sat eating my supper I realised that I would not have time this week to join Aaron and Jason for their Tuesday and Thursday runs. I sent them both a text message from my mobile informing them that for this week only due to work commitments I would not be able to join them in their runs but they were not to use that as an excuse to avoid doing it! Aaron replied within minutes saying that it wasn’t a problem and that he’ll see me at the leisure centre as normal at the weekend. Jason however didn’t respond until much later, in fact I was just about to turn my phone off when his message arrived. He said that it was okay with him but hoped that I wasn’t getting cold feet with him after the weekend. Stupid boy! I thought to myself, I was a little more tactful in my reply however. I assured him that there was no way I was getting cold feet and it was simply down to being on late shifts all this week. He then came back asking if he could stay over tomorrow night as Kirsty was still away? Not having the energy to argue I agreed to his request, if I’m honest I was just a little bit pleased with his eagerness to sleep with me again.

TUESDAY 27TH APRIL 2010

Dear diary, I’m going to skip the boring bits of today and jump straight to this evening’s training session in the chapel. It was slightly different tonight in the fact that Adrian was acting as compere in the auditorium whilst I and the contestants went straight to the training room next door and as before they removed their uniforms putting them to one side. As with last night James, Max and George were the camera men and Richard acted as shower assistant.

Standing in front of the eleven contestants I explained to them that the first task of the evening was to clean themselves inside and out. They were expected to do it without assistance as they had been shown how to do it the previous evening. No one made a move until they heard the creak of a video camera moving, this seemed to jolt them into action and this time Tyler took the lead and stepped up to the shower and made a great show of soaping himself up and then rinsing himself off. It was hard not to stand and gawp at him, as I’ve mentioned before he is pure beefcake, black as coal and hung like a horse. Then, not bothering to dry himself he bent over spreading his legs a little and greased up his little puckered hole. Next he took the douching tube, adjusted the flow of water through it and the temperature before carefully sliding the tube deep inside him. He remained in that position until he felt enough water had flowed inside before removing the tube and squatting over the toilet. On my instruction he hovered over the seat so that I (and the cameras) could see the colour of the effluent. Naturally on the first clear out it came out brown but by the third clearout it was clear.

Not wanting to be out done Flick announced that he would go next. As he showered I could not help but watch his dragon tattoos move as his washed himself, they were quality tattoo s and seemed to have a life of their own. Before long he was cleaned out and it was then the turn of Gus, then Carl and so on until all eleven guys were done.

While the last few guys were busy cleaning themselves out I went to the metal cabinet and retrieved eleven dildos of average cock size along with five tubs of Crisco and placed them all on a nearby couch ready for the next stage of their training. Calling them over I told them that as adult males we knew that they had experience in the art of fucking in an active capacity, however in the role of volunteer punisher they may be required to participate in man to man sex in a passive capacity. The purpose of the next exercise is to introduce their anus and rectum to having an object i.e. a cock up inside them, and as a responsible organisation it is safer to do it this way than to allow them to be fucked by another inmate without having any prior experience. As I was talking I looked round the group I could see a couple of faces looking worried, one was Sayeed (no surprise there!) and the other was Martin. I mentally made a note of this to ensure they got special attention from me.

I then went on to say that I recognised that some guys had already got experience of having cocks up them and if they didn’t mind they would take the bottom role to start off with so the others could be taught the correct technique for inserting the dildos. There were no objections and I didn’t expect any given the nature of the competition so I asked Eduardo, Dinesh, Jarek, Tony and Gus to get down on all fours on the floor facing away from us with their heads on their hands. This had the effect of raising their bums in the air and exposing their holes to us, what a sight indeed, five puckered holes waiting to be stuffed. Next I instructed Flick, Tyler, Darren, Carl and Martin to collect a dildo each and a tub of Crisco and then kneel down behind a hole of their choosing. Sayeed asked me why he had not been included, I explained that I already knew that he was experienced in stuffing holes and that I wouldn’t insult his intelligence by getting him to do this exercise. His pride was intact with this assurance and he nodded his understanding. Walking over to the group I told them to liberally grease up the holes in front of them all round the outside of the ring and then to take another glob of grease and push it inside the anus with two fingers and smear it all around as much as possible. Next they were to grease up the dildo and place the head of it at the entrance, tell the recipient to breathe deeply and relax before very slowly and gently pushing the dildo inside. Keep pushing until the dildo is fully inserted up to the silicone balls, place your hand on the base of the dildo to keep it in position and let it sit there for a couple of minutes before slowly pulling it back out. I told them to leave just the head inside and then push it back in again, then, with the other hand they were to reach between the recipients legs and take hold of the cock. Next while they slowly fuck the bottom they are to stroke the cock and wank off the recipient until he cums, only then can the dildo be removed. I asked them if they understood the instructions, I simply got nods of agreement as the five guys were concentrating on the tasks at hand. It was reminiscent of a porn film watching the five guys in a row being fucked with the dildos and wanked off. After about five minutes I heard Tony grunting and then the distinctive splat of jism hitting the tiled floor, I told Darren to remove the dildo and clean Tony’s hole up using the tissue I handed to him. Watching Darren do so I noted that Tony’s hole closed up quite quickly indicating that he obviously doesn’t get that much bottom action inside! A couple of minutes later Eduardo came, followed by Gus, Dinesh and finally Jarek. However their holes were slower to close up (as I expected) because they saw more action and were capable of taking larger objects. Whilst their holes remained open I pointed out to the “tops” that this was a good sign and indicated that the bottoms were completely relaxed. Now that they were all cleaned up I announced that it was time to swap!

The “tops” were a little hesitant in kneeling on the floor but after words of encouragement from the “bottoms” they did indeed swap positions. Eduardo now knelt behind Tyler, Dinesh behind Carl, Jarek behind Flick, Gus behind Martin and Tony behind Darren. I told Sayeed it was now time for him to join the other “bottoms” and that I would be taking care of him today. He threw me a quirky smile in response before assuming the same position as the others. I asked the new “tops” if they had any questions and reminded them to take extra care with their “bottoms” as they were relatively virginal, all shook their heads before starting to grease up the waiting holes. Confident that they knew what they were doing I focused on Sayeed’s hole before me. Following my own instructions I greased up his hole and pushed two fingers inside, he reflexively gripped my fingers before relaxing again. I then replaced my fingers with the dildo and as the head pushed up inside him I am sure that I heard him sigh. I let him get adjusted to the intrusion before sliding the rest of the dildo up his rectum. As I started to fuck him with the dildo I reached between his legs to find that he was already erect and his cock was throbbing. It didn’t take many strokes of the dildo to bring him to a growling climax and a large puddle of jism lay on the floor beneath him. I removed the dildo, wiped him clean and congratulated him on doing so well. He looked over his shoulder and smiled weakly.

Once everyone had finished the exercise and donned their uniform again it was time to tidy the room up and make our way back to the auditorium for the results of the voting. This time I had no idea of who would be voted off as they all seemed to have performed okay, if pushed I would guess it would be either Darren or Martin as they had seemed slightly shy and quieter than the others. We stood on the stage in a row, with me at one side, like last night the contestants stood up straight with pride and their hands clasped behind their backs in a show of confidence while we waited for the results. Finally Liam came over and handed me the envelope, with slightly shaking hands I tore it open and read out the name on the paper – Martin. As I read out his name his face showed his disappointment but he gave me a nice smile as I shook his hand in commiseration before asking him to surrender his uniform to me. With good grace he handed me his red beret and leather belt before bowing to the audience and walking out of the auditorium to remain naked until the following morning. I congratulated the remaining ten contestants and once again closed the proceedings by inviting everyone back for the next session tomorrow evening.

Back at home I quickly ate and had a shower before texting Jason to let him know that I was ready for him to come round. Twenty minutes later there was a ring on the door bell and I let him in with a casual hello, his response was more energetic. He shut the door behind him then grabbed me in a bear hug before pushing me against the wall and kissing me forcefully on the lips.

Coming up for air, he took a step backwards grinning and said “Boy have I missed you! I’ve wanted to do that ever since I last saw you.....”

“But that was less than forty eight hours ago.” I pointed out laughing, his cheerfulness was very contagious.

“Can we go to bed now?” Jason asked taking my hand and pulling me in the direction of my bedroom.

“In a hurry or something? I thought you were planning to stay the night.”

“I am but the time for talking is later, I need you NOW!” he said hoarsely as we reached the bedroom.

He pushed me onto the bed and started ripping my clothes off. He was in a hurry but didn’t fumble once (I take this to be an indication on his experience) as my T-shirt, socks, jeans and boxers left me and flew across the room landing in a pile – quickly followed by his own clothes. By the time he joined me on the bed we both were sporting erections, there’s nothing like raw passion to get a guy turned on! He lay on top of me, supporting himself on his elbows and started to kiss me on the mouth before moving onto nibbling my neck and shoulders. Deciding to turn the tables on him I reached up and pushed his head down my body. He took the hint and kissed his way down my body and tracing my hairline with his tongue until he reached my intended target, my pulsing erection. Taking his time he repeatedly licked the shaft applying copious amounts of saliva as he did so before placing the cockhead between his lips and looking up at me with lust filled eyes. Before I could say anything he went down on me and swallowed my entire cock in one smooth movement. Aah! The feeling of his warm moist mouth and throat was heaven! I could not help but flex my hip pushing myself further (if that was possible) down his throat. He gagged a little but quickly recovered and then started to give me a fabulous blow job. Not wanting to be selfish I tapped him on his shoulder to get his attention and then told him to scoot round so we could sixty-nine.

Giving me a thumbs up he carefully manoeuvred his hefty frame round so that his crotch was immediately above my head without releasing my cock from his mouth and barely missing a beat in his blow job. I looked up to be greeted by the sight of his ten inch erection less than an inch from my face, I stuck my tongue out just managed to lick his piss slit. Reaching up with my hands I gently pulled his hips do towards me giving me easier access to him. I abandoned all restraint and energetically sucked on his cock. I don’t know how long we carried on like this because we didn’t stop after the first orgasm. The first warning I had was when Jason’s hips shuddered slightly and his cock expanded a little then suddenly my mouth was full of his salty jism. I struggled for a moment to swallow it all but manage I did and I continued to suck him until he started to soften. I thought he might pull off me but no, he lowered himself slightly so I couldn’t pull away and concentrated on my needs. By the time I was ready to shoot he was hard again and actively fucking my mouth. This cycle was repeated several times before we admitted that we were spent and exhausted by our efforts. As he crawled his way back up the bed and into my arms a thought wheedled its way into my brain and it was one that I couldn’t ignore. I looked at his handsome face and all I could think was that no matter how wrong it was or how much trouble it may cause, I was not going to let him get away from me. I’m not sure if I can at this stage call it love but the thought of letting him go is very painful to me.

WEDNESDAY 28TH APRIL 2010

Day three of the training and tonight we got the contestants, after the now customary cleaning out, to give each other blow jobs and swallow the jism before getting them to fuck one another to orgasm. Now that we were really getting down to serious action it was intensely erotic, I am sure that we could do a side line in gay porn films! Yet despite this I found I was going through the motions of being the trainer rather than being really into the scene as I had been the previous two evenings. In fact I was glad when it was all over and we were once more standing before the audience waiting for the vote. The result did not come as a shock to me, Darren’s number was up when he spat out Flick’s jism in disgust and walked over to the shower without permission to wash his mouth out. He seemed relieved to be handing in his uniform and marched off stage with barely an acknowledgement to the audience.

Back home I reflected on my distracted state of mind and I quickly realised that Jason was the cause. I just couldn’t him out of my mind nor decide what do to resolve the problems I could foresee surrounding our relationship if it were to continue. For tonight at least there is nothing to be gained by torturing myself, I will just have to have a candid talk to him at the weekend after swimming.

THURSDAY 29TH APRIL 2010

After a good night’s sleep and giving myself a stern mental dressing down I was more able to focus of today’s activities. Which is just as well as tonight’s session in the training room was a lot more intense and even more erotic (for me at least) than yesterday. We were now down to nine guys – Flick, Tyler, Eduardo, Dinesh, Jarek, Tony, Gus, Sayeed and Carl. The competition was heating up and they were clearly determined to outdo each other to ensure their place on the next round.

By now I didn’t need to supervise their cleaning out as they were now doing automatically and actually helping each other, possibly to gain favour with the audience I imagine. That left me free to help Richard get the toys ready for action as tonight’s aim was anal stretching. Each guy would have four butt plugs, ranging in size from small cock size up to large fist size, which by the end of the evening they had to be able to fully insert into their rectums with ease. I liberally greased each one with Crisco and arranged them in size order, smallest at the front and largest at the back, on the floor in a circle. This was so that the contestants could monitor each other’s progress and act as an incentive to do better themselves.

I explained what was required from them this evening, saying that each time they successfully inserted a plug they were to stand up and bend over displaying the buried plug for the group to see and for my inspection. It wasn’t a race but to pass this round each guy needed to have inserted all four plugs, failure to do so would mean instant disqualification without the need for the audience voting. The nine men looked at one another with expressions that ranged from confident to apprehensive but none had time to dwell on the matter as I clapped my hands and told them to get started.

In no time at all Dinesh, Jarek and Gus had inserted all four plugs (not surprising as they can all accommodate fists up their back sides) and were free to act as encouraging mentors for the remaining six guys who were still trying to expand their horizons if you follow my drift. Eduardo and Tony were quickly onto the third plug whilst the others were having a hard time on the second plug. It was time to lend a helping hand, so I instructed Flick, Tyler, Sayeed, Carl, Tony and Eduardo to get down on all fours with their bums in the air, as they had done on Tuesday. Then Richard and I each took the biggest plug and started to slowly and gently fuck Eduardo and Tony with them until with groans from each man the huge butt plugs sank inside and their rings clamped firmly down on the plug’s neck. We left them to get accustomed to the massive intrusion before starting to slowly pull them out and reinsert them. After about ten minutes their holes were totally stretched out and they could swallow the plugs with ease. Their ordeal was now over and were allowed to shower themselves thoroughly clean. Whilst we were doing this Dinesh, Jarek and Gus had taken the third plugs and mirrored our actions on Flick, Tyler and Carl. Sayeed was left waiting until I was free to assist. Progress was a little slower with these four as they were less anally stretched than the rest but after a lot of encouragement and words of advice they all managed to take in the third plugs. As with Tony and Eduardo we left them for a minute before starting the fucking actions. Finally they were ready for the largest plug and half an hour later even Flick was now proudly impaled on the fist sized plug. The highlight of the evening for me was when Sayeed spontaneously shot his load all over the floor as the widest part of the plug slipped past his protesting anal ring.

Tonight the audience voted off Carl, the only reason I can assume is that he perhaps showed the least enthusiasm with the butt plugs or perhaps was the least photogenic.

FRIDAY 30TH APRIL 2010

Dear diary, I can’t believe another month has flown past, how time flies when you’re having fun! Or should that be when you’re working like mad and only getting a little bit of fun on the side......

Thankfully for my sanity at least, tonight was the last evening of the training sessions and the contestants have been whittled down to seven with Tony being voted off. Again as with Carl I think it was more down to the way he came across with the cameras rather than anything he did wrong.

Last night was relatively easy as far as pushing anal boundaries go, well I think so at least, tonight was going to be the final boundary to be crossed. After being cleaned out I told them that they were going to stand in a ring facing the back of the guy in front. Then having liberally greased up one hand and the arse in front with Crisco they were going to fist each other until the recipient had cum with or without manual assistance of the fister.

Standing back I observed the daisy chain fisting with a rock hard erection, the only thing holding me back from whacking off was the fact that the three cameras were all over the place trying to record in close up detail each fist as it slid in and out of the hole it was impaling and I needed to maintain a professional stance throughout. By the end of the fistathon eight guys lay collapsed on the floor in a sweaty, dirty heap totally exhausted and spaced out for their experiences.......

Having cleaned themselves inside and out again under a hot shower, I handed them their uniforms again before we strode back into the auditorium for the final vote off. After Carl was voted off Liam and I thanked everyone involved in the competition for all the hard work that went into making it a success. Then we thanked the competitors for participating in every task set before them and pushing their boundaries so willingly, and finally we thanked the audience for their votes and we hoped they enjoyed the spectacle. We also pointed out that they had selected the volunteer punishers themselves so they had no room to complain should they not like the results further down the road! The final speech I had to make was tell the remaining seven contestants that from tomorrow onwards they will be assuming the role of a Volunteer Punisher twenty four seven and would be expected to act accordingly at all times. Next week will be their final assessment when one last contestant will be voted off leaving the six permanent punishers.

After that they were free to go and enjoy their last night of relative freedom, talking of which I was now free myself to go back to my normal shift patterns and get back to having a social life again. Okay, that can be read as seeing more of Jason........ Mmm, now that’s a problem waiting to be solved.

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.