Diary of a Prison Officer Ch. 01

Saying nothing in response I did as I was instructed. It was the first time I had ever stuck a finger up a bum (including my own), it was very different to a vagina and in this case a lot tighter. I finally understood why the anus was called a ring; it was smooth just like the inside of my old wedding ring but a lot softer and warmer. It was so erotic feeling around knowing that my finger was the inside a living breathing person who by the sound of it was beginning to enjoy the sensations I was arousing.

"Now Flick." Liam continued "You have two options now. Would you like Sam to withdraw his finger and you will now be free to collect your belongings or would you like some relief for your aching cock?"

"Sir, I really need to shoot a load." Flick's reply was rather hoarse. "I don't think I can hold off much longer!"

"Sam, I want you to explore your boundaries and take a step beyond them. Firstly, keep your finger inside Flick, then with your spare hand I want you to take hold of Flick's cock and wank it off to orgasm. I know this is a new experience for you but think of the relief you will be bringing to our inmate."

Keeping my mind as blank as possible, not really taking in the enormity of it all, I did as I was told. Within a couple of minutes I felt his cock throbbing in one hand and his anus clenching round my index finger of the other hand, and then he shot load after load of jism all over his chest and stomach. As his cock subsided and started to shrink I gently pulled my finger out just as Richard came over a wad of tissues to wipe ourselves clean.

Max and Adrian released their hold of his ankles and Flick was allowed to stand up again, which he did with a sheepish grin saying "Thanks guys, I think!"

"No thank you." Liam replied. "You have complied with all that has been asked of you. We can now confirm that your records are fully up to date. Please collect your belongings from your box, you are now free to get dressed. We trust that we won't need to see you in this office again under these circumstances will we?"

"No Sir." and with that Flick went to collect his belongings and it was almost comical watching him scurrying over to the box with his name on it and rifling through it for his clothes. In less than thirty seconds he was dressed and making his exit. I was sorry to see his naked body clothed again. Liam must have read my mind as he laughed and assured me that it won't be the last time we see him in this predicament, well that was his feeling at least. It was 9.55am and we just had a couple of minutes to touch base and for me to be told that the next session would be run in exactly the same way.

Sure enough at 10.00am just as we had sat back in our chairs there was a knock on the door and in walked the massive frame of Tyler. Liam's preamble was word perfect and I took the opportunity to study the muscled frame of Tyler's back and legs. Evidently he was calmer than Flick because his massive hands hung relaxed down by his sides and his cheeks never clenched once.

Then the questions and answer session started.

"Okay, Tyler" Liam said, again reading from the record sheet. "Outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Straight"

"Have you ever had sex with a man?"

"Yes, but only when there's been no pussy to shag."

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

"Both oral and anal, I was sucked off and I did the fucking, the only way man."

"Okay, final question for now. When was the last time you ejaculated?"

"Last weekend, just before I got busted by you guys. My balls are nearly blue they're so full!"

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

"Uh huh? Go ahead, doesn't bother me none."

By now Richard had a fresh pair of gloves on and asked Tyler to face him. He gently cupped Tyler's balls in his hands and announced that they did appear to be very full and heavy. He then asked Tyler to turn around, bend over at the waist and with his hands pull his cheeks apart. Without hesitating the black guy turned round, bent over and expertly parted his cheeks for our inspection. I crouched down and inspected it closely with Richard by my side. We both agreed that it looked as tight and virginal as Flick's had.

"Damn right it is, nothing larger than a finger has ever been up there or ever will!" came the gruff response.

However unlike Flick, Tyler seemed to have little difficulty in accommodating Richard's finger nor mine when it slid in after Richard's had exited. I felt around until I found his prostate and started to massage it from the inside, this seemed to go down well with the patient because he clamped down on my finger before standing upright and taking a step forward leaving my finger behind. As I looked to Liam for guidance at this apparent defiance Tyler spun on his heels and faced me with hands on hips. In front of me standing erect was his humungous ebony cock, it had to be at least twelve inches long but still three fingers wide as it had been when flaccid. The foreskin had naturally pulled back revealing the equally black cockhead smooth and shiny under the bright office lighting.

"I think this is what you've been looking for, isn't it. Now be a good boy and give my cock a good sucking." Tyler said with a lustful gloating expression on his face.

I was in a quandary, the straight part of me was repulsed at the very thought of it yet, the new developing side just wanted to grab hold of it and lick it like it was the last lollipop in the world. I looked over at Liam hoping he would have an answer to my predicament; sadly it was not to be when he replied.

"Sam, it's entirely up to you. No one is forcing you one way or other. The only comment I would make is that by offering relief to Flick you got to know him a bit better, he respects you more which can only be a good thing and he will be a lot calmer now having shot his load. I dare say that will be true for Tyler."

"Oh man, if you could just do this for me then I would be the best behaved inmate on my wing, just a perfect pussy cat." Tyler confirmed as sincerely as he possibly could.

With a silent groan inside I nodded my agreement and indicated that he should step up to me. As the knob bounced in front of my mouth I could smell the faint aroma of the man, not strongly but just a little, clearly he had recently showered. For a moment I wondered if he had been expecting some action but then dismissed the very idea as being absurd and turned my attention to the task at hand. Tyler took a half step towards me, placed one hand on the back of my head and with the other hand guided his cock towards my lips. My mouth opened instinctively and waited for the inevitable, I didn't have long to wait. With a subtle thrust of his hips, the cock was in and completely filling my mouth, it kept on sliding in until it hit the back of my mouth making me gag reflexively. The head withdrew slightly before hitting the back again; once more I gagged to a loud tut above me.

Max knelt down beside me and in a quiet voice instructed me to breathe in gently through my nose as the cock entered, to completely relax my throat and breathe out as the cock withdrew. He also told Tyler to be patient as I this was the first blow job I had ever given. We tried again with me following Max's guidance, this time although I gagged slightly I was able to swallow more of his cock and after a few more thrusts was able to get about six inches of the cock in my mouth and down my throat. In the background I could hear words of encouragement. This spurred me on; I took hold of his hips and pulled him closer towards me. As a reward for my eagerness . upped the tempo and really started to fuck my face, with considerable concentration I was able to time my breathing to his thrusts and before I knew it my nose was brushing his pubes and his cock was buried fully within me. All of a sudden he started to shudder and growl, his cock pulsed (I guess he was shooting his load down into my stomach). Slowly it subsided and he pulled it out much smaller and covered in saliva and jism. It certainly came out easier than it went in! I gave a loud belch, which caused a round of laughter, licked my lips and in a rather a hoarse voice asked for a drink of water to wash the spunk down. Richard helped me to my feet and led me to my chair while I got my breath back under control, then hand me and Tyler a tissue each to wipe ourselves clean.

Liam glanced at Tyler who was busy wiping his now flaccid cock clean and said

"Tyler, I never thought I would say this but thank you for helping to educate Sam here. You have done all that was asked of you and you have shown a side of you rarely seen by us prison staff. Please collect your belongings from your box, you are now free to get dressed. We can now confirm that your records are fully up to date."

Tyler didn't seem in a hurry to get dressed, he walked over to box, unlocked it, retrieved a pair of shorts, holding them casually in his hands he turned towards us and said

"Pete mentioned something about my services being required to administer punishment to prisoners, was he being genuine or was he just using that as a ploy to get me to go along with the punishment?"

Liam looked at him thoughtfully for a moment, while Tyler pulled his shorts up and retrieved a T-shirt, before carefully replying.

"No Pete was telling you the truth about requiring volunteers, we're currently drawing up a shortlist of possible candidates and yes you are one of the candidates being considered."

"Seriously? That's brilliant, I've done nothing but think about it for the last two days and I think I would be perfect for it, don't you Sam? When will I know if I've been successful? "

"That very much depends on you to be honest, we will be assessing everyone over the next few weeks and your behaviour will be scrutinised meticulously, one foot wrong and you will not be considered further. We have to be absolutely sure of your commitment and that you will not abuse your position of power over the inmates."

"Okay okay, serious stuff then. Count me in though, I promise I will be as good as gold. What can I do to convince you of my sincerity?"

"Well, for a start, once you are a volunteer punisher your services can be called upon at any time, day or night and it is important that you provide a highly visible deterrent. All volunteers will be permanently naked except for a red beret (like the military police). So if you want to make a real start with your training and show us your commitment then I suggest you remove all your clothing from the box, you may keep your other possessions, surrender them to us now and remove your shorts and T-shirt you have just put on."

Tyler was cornered, if he refused to do so then his voluntary career was over before it began, however he thought quickly on his feet.

With a simple "Right you are then." He took off his T-shirt and stepped out of his shorts, once again revealing his magnificent cock, placed them on the table and proceeded to remove the rest of his clothes from the box. Within five minutes we had a pile of clothes on the table and one aroused Tyler wheeling his box out of the room. Liam called after him that we would be in contact with him. I asked Liam what the plans were, he replied that he had no plans but it seemed like a good idea at the time! He was sure that he would think of something soon.....

There was a knock on the door, it was 11.00am already! As we drank our second cup of coffee of the morning Eduardo from C-Wing walked in, as naked as the other two men had been. He was a handsome young man, slim and no older than twenty three. He was in prison for drugs offences and it was these that had been found in his cell resulting in him being stripped of his possessions. He had a certain juvenile cockiness which was endearing rather than annoying as can often be the case.

As he stood facing Liam listening to the preamble I studied the young man's figure. His jet black hair was cut short and his skin had the typical Mediterranean olive complexion except for his cheeks which were a glowing white, I guess from wearing Speedos when out sunbathing. His legs were hairy as were his arms but his back was quite smooth.

"Okay, Eduardo" Liam asked. "Outside the prison environment would you describe yourself as normally being gay, straight or bisexual."

"Bisexual"

"Have you ever had sex with a man?"

"Yes both inside and outside of the prison. I enjoy it, I like girls but I also like guys."

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

"Both and I am versatile."

"Okay, final question for now. When was the last time you ejaculated?"

"This morning, I was fucked by my cell mate and I came without touching my cock."

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

"I have told you the truth, I have nothing to hide."

As this was the third time we had carried out this scenario I knew what was expected so while Richard proceeded to weigh Eduardo's balls I slipped on a pair of latex gloves and started to lubricate them with the KY. Eduardo's cock rapidly expanded and became erect, from the corner of my eye I could see that he was watching me getting prepared; clearly the anticipated procedure was turning him on. I asked him to turn around, bend over supporting himself on his elbows and to spread his legs wide.

He smiled and said "Si, Senor" before doing as he was told. I squeezed a little of the KY onto his anus and carefully smeared it around his ring before gently inserting the tip of my finger as I had with the other two guys. I could feel the difference immediately, with Flick and Tyler there had been a lot of resistance and they had clamped down on my finger every time my finger moved inside them, however with Eduardo my finger slid in easily right up to the hilt. It was only then that he clenched momentarily, gave a little wiggle of his hips and looked over his shoulder at me with a smile on his face.

Richard stood beside me and quietly spoke into my ear suggesting that I try to insert another finger or two to assess how anally experienced Eduardo actually was. I withdrew my finger and applied more KY to my fingers before placing two of them at his entrance and smoothly pushed them inside until I could go no further and then pulled them out again. As Eduardo had shown no reaction I decided to try a third finger, as I inserted the three fingers I detected more resistance and as I sank in up to the third knuckles he started to clench down hard on my fingers and his body language made it clear he had reached his limits. In response I withdrew my fingers and wiped them clean on some tissue offered to me by Richard, who asked me what my conclusion would be to this exercise. I thought carefully for a moment before replying.

"Well, I would say that this young man is certainly comfortable with having objects inserted up his rectum and judging from the dilation he is more that capable of accepting most cocks up him."

Richard nodded sagely and agreed with me, he then invited Eduardo to stand up as the inspection was over. As Eduardo stood up and stretched his back and arms, Max whispered in Liam's ear who nodded and then turned to Adrian who also nodded thoughtfully after a couple of seconds. Max looked over to Eduardo and said

"You have done all that has been asked of you and we confirm that your records are fully up to date. You are now free to get dressed and can collect your belongings from your box; however we are curious about the statement you made about being able to ejaculate without touching your cock. We wonder if this is an empty boast."

Eduardo gave a nervous laugh and assured us that what he had said was the truth and if required he would demonstrate this fact to us. Max nodded and said that they would like to see this trick. Eduardo simply smiled in response then looked at me and said that he would like me to help him.

"Help you? In what way?" I asked, clearly naive despite me being a man of the world as my mates call me.

"Si, I would like you to fuck me. I will lie on my back on the floor and you will insert your cock up my arse and fuck me until I cum."

He left me in no doubt that he was serious, again I looked over to Liam who smiled and nodded encouragement. Mmm this was really pushing my boundaries; I had never fucked a bloke before. I've had anal intercourse with a woman and it was okay, at the end of the day a man's hole can't be much different to a girl's can it? So feeling just a little self conscious I removed my uniform, placed it neatly folded on my chair, I didn't look up until I was standing stark naked and playing with my cock to wake it up again. Richard walked over to me and with a wink squeezed a generous amount of KY onto his fingers before taking my cock in his hand and lubricated it from base to head. Well that did the trick! My cock was rock hard within a few seconds and I was ready to go! By now Eduardo was laying on his back with a chair cushion under his hips, with his arms wrapped round his knees exposing his anus to me which was still glistening from its previous lubrication and was just slightly open. It was the sight of this that drew my eye and all I could think about was sliding my cock into it and shooting my pent up load deep into him. Wasting no time I knelt down and then placed one hand on his thigh, with the other I guided my cock to his waiting hole. Then when my head has gently pushing against the ring I removed my hand from my cock and held onto his other thigh. In one smooth thrust I fully entered him and buried myself up to the hilt causing a groan of pleasure to escape from his lips. Giving him a moment to adjust to the impalement I looked down at his cock and it was throbbing with a life of its own, then slowly I thrust in and out gradually building up the tempo trying to reach further and further inside, only stopping when my balls slapped up against his cheeks. He let go of his legs and let his arms flop onto the floor, I moved my hands to his ankles and spread his legs wide so the others could have a clear view of his cock. On and on I banged his butt, it felt so good, never had I fucked a guy's arse before nor one so much younger than myself! Eduardo was constantly groaning and slowly he started to writhe around, then arching his back and a thrash of his head he yelled out as his cock suddenly spewed out jets of jism all over his face and chest. His anus clamped rhythmically down on me which tipped me over the edge and I shot my load too deep into his bowels before collapsing on top of him, smearing his jism all over my chest.

For several minutes we simply lay there catching our breaths, as I raised myself up Eduardo caught me by surprise by kissing me hard on the lips. My face must have been a picture because he chuckled as so did everyone else in the room. Once more Richard did the honours by offering us tissues to clean ourselves up with, as I wiped myself off I could not help but wonder what else could happen today, little did I know! As I put my clothes on again lost in my own thoughts I didn't hear Eduardo come up behind me on his way to his box, he whispered in my ear making me jump.

"Senor, any time you would like to fuck me again just let me know, your cock is very big and I love it!"

"Uh thanks, I'll bear that in mind."

"Please do."

Then without further ado he trotted over to his box, opened it and quickly got dressed before pushing it out of the door with a cheery wave to everyone in general. There was about ten minutes spare before the next inmate was due so Liam took the opportunity to quiz me on the last session and had I enjoyed fucking Eduardo. I gave my honest feedback and yes I had enjoyed myself.