Diary of a prison officer : Part 2


(Part 1 from 5. Fiction.)

*** All characters contained within are entirely fictional; any similarity to any real or fictional person living or deceased is totally unintentional. Do not read this story if you do not enjoy reading about consensual sexual activities of an exhibitionist nature. Otherwise read on......

THURSDAY 1ST APRIL 2010

A new month has begun and the Easter holidays lay ahead of me, a whole four days of freedom from the usual routine of work. On the one hand I’m lucky because I’m one of the few Prison Officers who has been granted the whole weekend off (favouritism I have heard muttered by some), on the other hand having four days off with nothing planned seems a waste of time when I could be earning double time. But as they say all work and no play makes Sam a dull guy so I will just have to find something to occupy my time, starting with housework and ironing tonight so I don’t have that chore hanging over me for the rest of the weekend!

FRIDAY 2ND APRIL 2010

Well diary, I have had a more interesting day today than I thought I would, or perhaps curious would be a better term.

This morning first thing I jumped into the car and paid a visit to the local supermarket and stocked up with some groceries, I don’t know if I’m being paranoid but I am sure that I caught more than one person giving me the eye up. It got to the point that I stopped and checked my reflection out in the shop window. No, everything seemed in order, just my usual jeans, trainers and tight fitting muscle top. Okay, I know that my physique has improved since I started at the prison but I didn’t think it was that much improved! The other thing which has occurred to me is that perhaps I am developing what I have heard called ‘gaydar’, that is being able to sense when another guy is interested in you.

When I was bent over one of the freezers trying to decide which pizza to have tonight, something made me look up and straight into the eyes of a cute looking shop worker, he must have been all of eighteen with big blue eyes and a thick mop of blonde hair. He flushed bright red having been caught in the act of staring at me and gave me a weak smile in an attempt to cover up his embarrassment. I winked in response and gave him a broad grin before looking back at the pizzas on offer. When I had made my choice and looked up again, the young lad had disappeared. Feeling a little disappointed I silently chided myself because he was far too young for me – I was old enough to be his father!

Then as I was queuing up at the checkouts, I was lost in idle thought when something caught my eye and as I looked over to the next till a guy, perhaps in his thirties gave me a sly smile before quickly looking away as his wife looked up from what she was doing and spoke to him. I was so surprised I failed to respond and stood there in a daze, until a loud cough behind me brought me back to reality and I started to unpack my shopping onto the conveyor belt. Finally the checkout girl was all touchy feely and overly friendly. Enough was enough! I had to get out of there quick before anything else happened.....

Back home, having unpacked and made myself some lunch I felt bored and lonely. Refusing to give into this self-defeating frame of mind I decided it was time for some company, and I knew just the place for it – the leisure centre. It’s always guaranteed to be busy; I could get some exercise and was bound to bump into someone I know. Which is exactly what happened and led to an interesting meeting with Jason (Aaron’s best friend, who went to the stag do).

I paid the entrance fee and made my way to the male changing rooms as normal, found the locker I had been allocated and followed the routine I always do. Call me OCD if you like but I have always done it since being in the army. I opened the locker; then removed my trainers and socks before stuffing the socks into the trainers and then into the locker; off came my jeans to be folded neatly and placed on top of the trainers; next my muscle top and finally my boxer shorts, again both were neatly folded and placed into the locker. Standing there comfortably naked I retrieved my towel and swimming trunks, placed them on the bench, then put my sports bag into the locker, spun the combination lock and turned back towards the bench. As I reached for my trunks I heard my name called and looked over in the direction of the voice. Walking briskly towards me was Jason with a Cheshire cat smile on his face; reaching me he dumped his bag on the bench, gave me a great hug and a hearty slap on the back, seemingly oblivious to my state of undress.
I coughed loudly to draw his attention to the situation as a couple of guys were beginning to stare and I was feeling distinctly uncomfortable.

“Sorry Sam!” Jason chuckled stepping back, “I didn’t mean to embarrass you but I am just so pleased to see you. I’ve been meaning to catch up with you ever since Aaron’s stag do but I’ve lost your mobile number and felt a little awkward asking the other guys for it again.”

As I listened to him I donned my swimming trunks and slung my towel over my shoulder before replying “I didn’t know you had my number in the first place, not that I mind you having it, I’ll give it to you now if you wish.”

“Oh that would be great! Let me just get a pen out of my bag and I’ll make a note of it” he replied doing exactly that.

Closing my eyes to aid concentration I gave him my mobile number and got him to repeat it back to me for accuracy, only then did I ask him what he was doing here.

“I have been putting so much weight on recently that Aaron and his dad has started to pull my leg about me getting fat and no longer being a babe magnet. They suggested that I follow your example by getting out and exercising more, which is why I am here. I thought I would start off gently by doing some swimming, gain a bit of confidence and see if there’s anyone who can give me some guidance on doing things the right way. That’s why I’m glad to have bumped into you. You’re exactly the right guy for the job, that is, if you don’t mind.....”

“Well, I’m flattered naturally, that you feel I’m the man for the job” I replied, a little surprised by what I had just heard “but I must warn you that I’m only an amateur and not qualified as a sports physiotherapist. I can tell you what’s worked for me and what hasn’t; then the rest will be up to you. Anyway, you don’t look overweight to me.”

“Oh I am, believe me” Jason retorted with a frown. “You’ll see in a moment.”

Without further ado he removed his Jacket, slung it on the bench and then started to remove his jumper.

“Before you go any further Jason, have you located your locker yet?” I asked with an amused smile.

“Oh shit, no I haven’t! Thanks Sam. See I know I’m going to be in good hands..... Now where is it? Ah there it is. That’s handy; it’s only a couple away from yours.”

Having opened the locker Jason threw in his jacket and jumper before his shoes, socks and jeans joined them. He paused momentarily standing in just his T-shirt and pants, then apparently having summoned up the courage he removed his shirt, threw it in the locker before slowly peeling down his pants and stepping out of them. As he stood up straight again his huge cock swung pendulously from side to side above his hairy balls.

I could not help myself but to whistle appreciatively and mutter “You sure are a !”

“I know, this is exactly what I meant” Jason responded prodding and poking at his developing beer belly.

I chuckled before saying “Okay your stomach could do with a little toning up but that wasn’t what I was referring too....”

By now Jason had put on his Speedos but his ample package was still very evident for all to see (should they wish to look), he glanced over to me with a strange expression on his face before it lifted to be replaced by a smile and a slightly camp “All the girls say that!”

In a more serious tone he asked me to have a look at him and let him know what parts of his body I thought he needed to pay attention to and then did a slow pirouette with his arms lifted slightly. I deliberately took in every part of his body; his muscled hairy legs, slightly prominent beer belly, his hairy chest and arms were decently proportioned, his bum was masculine in it’s squareness as was his jaw line. He wasn’t classically handsome but all the same was very pleasing to the eye and was sporting a trendy haircut and razor thin goatee and beard. I was slightly envious of the fact that he could sport that style of beard due to the blackness of his hair whereas my hair had always been too pale a brown to carry off such styling, made all the worse by the increasingly common white hairs.

“All in all” I announced “you’re not in bad shape, you’ve just got to lose that tummy of yours. Cutting out the beers and junk food along with some decent exercise should sort out in no time. Now shall we go for a swim before we get done for loitering?”

We spent the next hour in the main pool alternating between serious length swimming and getting our wind back breaks treading water and making small talk. By the end of the hour we were both exhausted and glad to stand for a few minutes under the invigorating hot showers. While we were towelling ourselves dry and dressing once more we talked more about the exercises he should be doing on his own.

“Well, what are you doing tomorrow for exercise?” Jason asked casually.

“Oh, I shall probably do a couple of laps of gently jogging around the park, but that will be all. Why? Would you care to join me?” I replied just as casually.

“Would you mind? I haven’t done any jogging for years. Well not since school at least.”

“Of course I don’t mind. You know where I live, just call round, say 10.30am and I’ll break you in gently, so to speak” I said with a smile.

“You’re on! See you tomorrow then.” Jason said clapping me on the shoulder and headed for the car park.

I went in the opposite direction having walked to the leisure centre from home. Well, I only live a mile and a half from there; it seems crazy to drive that short distance to a place you’re trying to get fit in! Twenty minutes later and I was back home again with my mind focused on locating all of the men’s fitness magazines and books I had stashed around the flat and never quite got round to reading. If I am going to be a fitness coach I must at least sound like I know what I am talking about!

So my Friday night has not resulted in me being down the pub as usual talking to Tom and Mike in the Kings Head over a pint or two of beer, instead I have had my face stuck in umpteen magazines and books formulating a fitness routine for Jason.

SATURDAY 3RD APRIL 2010

Woke this morning bright and early with the sun streaming in through a chink in my curtains, lay there listening for a few minutes to the cheeping of a couple of sparrows on my bedroom window ledge before passing traffic drowned them out. Oh the joys of living in central London I thought to myself, one day I hope to be able to move out into the suburbs and away from the traffic and pollution. In the meantime I am enjoying the facilities and convenience that living here offers, who knows one day....

Having got up early I had time to enjoy a leisurely breakfast and pop down to the newsagents to fetch the daily newspaper. I was still reading it when there was a ring on the doorbell, leaving the paper open where it lay (to make it look more casual) I answered the door to a bright eyed and bushy tailed Jason, wearing jogging bottoms and sweatshirt, clearly raring to go.

“Come in, come in young man” I greeted him with a smile.

“Morning Sam, I hope I’m not too early.”

“No you’re right on time, I’m actually running a little behind time, so please make yourself comfortable while I just get my running gear on” I said as I wandered into my bedroom and retrieved a pair of shorts and a muscle top from my chest of drawers. I quickly shucked my tracksuit bottoms and T-shirt, throwing them on the bed and was in the middle of putting the muscle top on over my head when I heard Jason’s voice close behind me asking if he could use the toilet before we go for our run.

Not turning round I said “Sure, of course you can. It’s the door straight in front of you.”

“Thanks.” He replied.

Strange I thought; I’m sure he’s been here before so he should know where the toilet is. Shrugging my shoulders I thought no more of it. I quickly pulled on my shorts and was tying up the laces of my running shoes when Jason returned. Without further ado we made our way out of the block of flats and over to the park where our run would start in earnest.

Poor old (or rather that should be ‘young’) Jason, he was clearly out of shape and by the second lap of the park he was flagging. I looked over at him, he was red faced, sweat was pouring down his face and his gelled crest was distinctly wilted, his shirt looked like it had been in a wet T-shirt contest. Finally the ordeal was over for him as we reached the park gates and I told him he could stop and take a breather. His expression was a picture, there he was totally exhausted and here was I nearly twice his age scarcely panting.

“Let’s go home Jason, you’ve earned a rest, how about you have a hot shower when we get back to sooth your tired muscles before we look at some exercises you can do before next weekend.” I said as briskly as possible.

Jason didn’t have the energy to say anything; he simply nodded, stood up straight and tried to match my pace as we made our way back to the flats.

In the bathroom I showed him how to operate the shower, where the soap, towels etc were kept and left him in peace while I laid out the light lunch I had prepared earlier on the kitchen table. I was just pouring the fruit juices out when I heard the noise of gently padding feet behind me, turning round I saw the naked frame of Jason walking in with just a towel wrapped round his waist, his lunchbox was making a distinctive bulge at the front.

“Does that feel better?” I asked, doing my best to keep my eyes off his crotch.

“Yes thanks, I almost feel ready to go again!”

“No I don’t think so, one run per day is quite sufficient that is unless you wish to injure yourself. I thought we would have a light lunch and then I will show you those exercises before you leave.” I said as I handed him a glass of apple juice.

“Sure, sounds good to me” he replied, making himself comfortable at the table and quickly started tucking into the salad and French bread.

When we’d eaten sufficiently I ran through the sit ups, press ups, squats and stretching exercises demonstrating each one to him. As I was showing him each one I got the distinct feeling his mind was elsewhere and asked him if this was the case. A little embarrassed he admitted he was a little distracted but wouldn’t divulge any further information so I didn’t press him as it was none of my business.

“Okay, let’s see how much you have taken on board what I have said. Please join me down on the floor and I want you to do some press ups.” I said in the best coach voice I could muster.

“I know how to do that.” He responded.

“You might think you do but I want to be sure that you are doing it correctly.”

With a sigh he laid down on the floor, feet towards me, head away and started to do a couple of press ups.

“No you’re doing it wrong” I admonished him. “Your feet should be a apart to give yourself greater stability and place less strain on your wrists. Try it again please.”

He did as requested and started once again, this time I had a good view between his legs and could see his balls swinging gently with each movement. I could just make out his cockhead hanging just below his balls. My cock twitched a little at the sight.

“Okay, that’s fine. Now let’s see you do some sit ups. I will hold your feet to provide you with stability, say do five for me.”

Not saying anything, he simply sat in front of me with his feet flat on the floor; knees bent and then lay back on the floor with his hands behind his head. If I thought the previous view was good, then this one was fantastic! Jason’s towel had slipped under gravity down from his knees to around his waist fully exposing his cock, balls and arse crack. I couldn’t help but lick my lips in response. As he carried out the sit ups he kept his eyes focused on the wall behind my head, only when did he complete all five sit ups did he look down and realised that his towel had slipped exposing his assets.

“Sorry Sam, I didn’t mean to give you an eyeful! It’s my fault I should have got properly dressed and not been lazy by keeping just this towel on. I hope I didn’t offend you in any way.” He said as he quickly stood up and rearranged the towel to cover himself once more.

“Hell no!” I replied “I’ve seen it all before, both in the army and more recently in the prison service. Nakedness has never bothered me, don’t give it another thought. I often walk round here naked when I’m alone, though not so often when I’m in company!”

“Cool! It’s just that some people are bit stuffy when it comes to men’s bits, for example my girlfriend. How she hates the sight of my bits on display except when we’re having sex, says they’re disgusting. Me, I can’t see what’s wrong with them personally.”

“No, I can’t say that they look wrong in anyway. Certainly nothing to be ashamed of, and if I remember correctly you didn’t seem too averse to taking your kit off during the stag do!” I remarked with a chuckle.

“True. But it’s amazing what a little bit of alcohol in your system can do for your courage! I hope you don’t mind Sam but I really must be going now. It’s nearly 2pm and I said I’d meet Kirsty at 2.30pm, if I’m not careful I’m going to be late and she doesn’t like to be kept waiting.”

“That’s fine with me. I think to be honest we’re just about done; I can see that you know what you’re doing. Run along and get dressed, I don’t want you to get into trouble on my part. Regarding ongoing training, how about we go swimming on Sundays and do jogging on Mondays and Thursdays. How does that sound?” I asked. “That way you get a couple of days rest in between each activity.”

“You’re the fitness boss. I’ll do whatever you recommend.” Jason replied as he hurriedly put on his rather damp and sweaty running gear.

“Next time we go running it might be worth bringing a change of clothing; that way you won’t have to put on those rank sweaty clothes afterwards.” I suggested.

“Good idea, I should have thought about that. Right oh, will do, I’ll see you on Monday then? Will it be okay if I bring Aaron with me next time? It’s just that he said if everything went well he would like to join us.”

“Sure, more the merrier” I replied and shut the front door behind him.

MONDAY 5TH APRIL 2010

Dear diary, sorry about not writing an entry yesterday but nothing happened. Literally! It pissed down with rain all day, spent most of the day lounging around on the internet and watching old movies on the TV. Waste of a day, I guess but I enjoyed it in a way.....

Back to today, went for our planned jog round the park with Jason and Aaron. This time Jason was more prepared, they both had a change of clothing and like me they wore shorts and muscle vests for coolness. To be frank neither were particularly fit and this time they were exhausted after one lap, so we had a five minute break slowly walking before picking up the pace again. The dynamics with the three of us was different and I felt more like a father out with his two sons; slightly distanced as the two guys are such close mates.

Back at my flat we took it in turns to have showers. Jason went first, then Aaron and finally me. Jason, as ever took the lead by returning from the shower wearing just his towel as he had on Saturday. Aaron looked slightly surprised and looked at me in askance.

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

“You’re cooler than dad you know.” Aaron called out on the way to the bathroom.

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

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

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

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


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

“As you’re back now, I’m just going to have my shower. I’ll be back in five.”

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

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

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

TUESDAY 6TH APRIL 2010

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

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

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

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

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

“Yes” was our simple answer.

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

“It’s embarrassing Sir, is there anywhere I can talk to you in private?” Jarek asked.

“What’s wrong with talking here?” I responded.

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

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

“Thanks Sir”

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

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

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

“Right Jarek, how can I help you?”

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

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

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

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

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

“In what way are they special?”

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

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

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

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

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

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

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

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

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

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

“And what is that?”

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

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

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

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

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

“Yes Sir” was all he said in response.

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

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

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

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

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

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

“How does that feel? Any discomfort?” I asked.

“Fine, no discomfort at all” came the calm reply.

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

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

“What do you mean?” Came a slightly breathless reply.

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

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

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

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

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

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

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

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

“Aaaaaargh! I’m cumming! Eeeeeergh!”

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

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

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

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

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

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

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

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

“Yes Sir, of course I trust you.”

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

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

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

“Okay.” Was all he said.

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

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

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

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

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

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