Diary of a Prison Officer Ch. 02

"Would you like a beer? Can I offer you anything else?" I asked as innocently as possible.

"Anything else?" Jason replied, voice raised just a little. Something must have been lodged in it because he had to clear his throat before continuing "What do you have in mind?"

"Dunno really, I've got some chips in the freezer, or I can do us a salad. Actually, if you want to have a look in the cupboards and let me know if there's anything you fancy. Personally I'm going to have a salad as I have to watch my weight these days, I don't want to get belly or fat bum!" I patted both as I said this.

I sensed a deflation in him as he realised I wasn't suggesting what he thought I had. His towel still had a slight tent pole but he ignored it as he stood up straight and said "If a salad is good enough for you then it's good enough for me, after all it's me who needs to lose the weight. Look at you, there's not an ounce of fat on you anywhere!"

Smiling in acknowledgement I set about preparing a ham salad, not giving my nakedness another thought but making sure that I struck suggestive poses wherever possible. Jason didn't say anything untoward but his tent pole never went down one little bit. Once we had eaten we moved into the living room and watched the 10 O'clock news on ITV. I sprawled out on the sofa, making sure that my tackle was nicely displayed and Jason sat in the armchair, for some reason he seemed to have trouble concentrating because out of the corner of my eye I noticed he kept glancing in my direction. After the news he decided that he needed to be getting home and so retrieved his clothes and got dressed before bidding me good night. Poor boy he just couldn't help but look at my body one more time as he shut the door behind him, on the other side of the door I was grinning to myself knowing that my intuition had been right all along.

FRIDAY 9TH APRIL 2010

Last day of the week thank God! My poor hole will be getting a rest for a couple of days, from prying fingers at least.

Richard and Liam were waiting for me in the consultation room as I arrived, and it was straight down to business. I was told to strip and assume the position for being cleaned out. I won't bore you with the details but it was exactly the same process as yesterday, although a little easier as I knew what to expect. The I was told to hop onto the couch but this time stay on all fours with my head on my hands (actually this position was identical to the one I got Jarek to assume last Tuesday).

It wasn't long before I felt latex covered fingers tickling my anus, making me wriggle a little before I felt the familiar sensation of cold Crisco being pushed into my hole and smeared all round it. First one finger went in, then two, all the time they were rotating and massaging the anal ring. Their movement was hypnotic and I was almost in a trance when I felt a third finger join them. I shifted my weight a little and was asked if I was okay, all I could do was respond with an affirmative grunt. The three fingers massaged their way for what seemed an eternity, my hole was getting looser and I was just beginning to feel restless when they were withdrawn and I was told to climb off the couch and stretch my body for a minute while Richard fetched the next piece of equipment. Did I say piece of equipment, more like a cross between an item of clothing and an instrument of torture!

As I was limbering up, touching my toes and then the ceiling etc, Richard walked back into the room carrying what looked for all the world like a leather thong. I said as much to him and he nodded in agreement.

"You are right Sam. That is exactly what it is, although not one you are able to buy in Marks & Spencer! I just have to connect the attachment and we're ready for your first fitting."

Fitting for what? I asked myself. I didn't have long to wait before I found out. Richard reached into a drawer and pulled out a box of what looked like black rubber objects, light bulb in shape with a metal screw thread at the neck end. There followed a brief discussion between Liam and Richard before an agreement was reached and the required object selected. Richard then picked up the throng and appeared to screw the "light bulb" onto the narrow part of the thong. Sometimes I can be so thick because I still didn't have a clue about what was coming next! When he was satisfied that all was in order he knelt down on the floor and asked me to stand in front of him facing away, which I did. He then asked me to step into the outstretched thong, which I did, only then did it occur to me what the bulb was for.

"Please pull the thong up to your waist and maintain that position." Richard instructed.

I did as I was told, then I felt a hand reach between my legs and take hold of the bulb before placing it against my anus and gently pushed it upwards. It felt bigger than it looked and was certainly bigger than the three fingers I had just accommodated.

"Spread your legs a little and push out as if you're about to drop a log." I heard Richard advise from behind me.

Well that paints and interesting picture I thought, but again did as I was told. All I can say is it worked, by spreading my legs I ended up squatting slightly and as I pushed out I felt Richard apply more pressure. In less than a minute the head of the bulb made its abrupt entrance into my rectum and my ring clamped shut tight around the neck.

"Aaaaaargh! That hurt!" I groaned.

"It's okay, your ring will calm down in a minute or two, it's just not used to stretching that extra bit" Liam assured me. "What we want you to do is to wear this thong when you go to bed each night, leave it in place all night and then remove it in the morning, okay?"

"Um, yes, okay I guess. Can I take it out now?"

"Is your anus still aching?" Richard asked.

"It is a little, I also feel very full like I need a crap badly." I admitted quite frankly.

"In that case you need to keep it in a little longer to allow your body to adjust to the intrusion. Please climb up on to the couch and lay down on your front as if you're going to have a massage, then RELAX." Liam instructed.

As I lay there relaxing doing my best to ignore the object within, I felt fingers slip underneath the thong and explore the boundary between the neck of the bulb and my ring. For a couple of minutes they massaged all the way round several times before withdrawing and grasping the neck. I then felt the bulb being gently tugged, then pushed in further, wiggled around and then the cycle started again.

"How does it feel now?" Liam asked as Richard continued his ministrations.

"Okay actually thanks, I no longer feel any discomfort at all which I am surprised about" I replied.

"Good, that is progress indeed. We're now going to take it out now so just relax and as before push out gently." Liam said.

It came out with a plop, slightly uncomfortable but certainly not painful like it had been going in. I was then told the training session was over, I could clean myself up and get dressed. As I was dressing Liam reminded me that I was to wear the thong & insert the bulb each night until the next training session on Monday. Then it was back to work, this time George didn't bother asking where I'd been as he knew I wouldn't say.

This evening just before bed time in the privacy of my own bathroom I tried to insert the bulb again. Although I was using the same grease that Richard had given me, this time it just seemed so much harder! No matter how I tried it just wouldn't pass my golden gates. I was getting very frustrated. Then I recalled the trick about squatting and pushing out at the same time, I am so glad no one was there to watch, it was all rather undignified. There I was squatting over the toilet with rubber bulb in one hand, the rest of the thong in the other hand to prevent it trailing in the water and me pretending to have a dump! Mind you, once again the trick worked, in it popped as quick as you like, but boy did I break out in a sweat and groan. It wasn't so much painful more like a throbbing toothache which slowly faded away. With the bulb inserted I stood up and pulled the thong on and made my way to bed. What I do in the name of duty.......

SATURDAY 10TH APRIL 2010

Dear diary, if I am honest I thought today was going to be one of those unremarkable days but actually it ended on a high note so I guess I can't complain.

Woke up this morning after a good night's sleep, I had totally forgotten about the thong and bulb so was a little confused by the feeling as I normally sleep in bed with just a T-shirt on.

Went to the bathroom to remove it using the same trick as last night, I was surprised to find that my ring really didn't want to let go of it but after a bit of huffing and puffing it shot out along with a load of shit behind it – major yuk! Not the best sight or smell first thing in the morning; I retrieved it from the pan and gave it a very thorough washing along with my arse which felt strangely loose. It was, I could easily stick two fingers up inside with no problem or lube!

Having recovered from that shock I got dressed, shaved, had breakfast and went shopping for the mundane things in life like food and groceries. Then home to more mundane things like housework, washing and ironing.

By late afternoon I was totally bored so I called Tom to see what he was up to. He said he was glad that I had called because he and Chrissie were entertaining Mike, Aaron and his wife Sally, Jason and his girlfriend Kirsty this evening and if I could join them it would make the numbers even. I leapt at the chance to have dinner with my two best mates, they're always good for a laugh and Chrissie is lovely as is Sally. Kirsty I don't know but knowing Jason she is bound to be pretty and educated. We chit chatted for a while before Chrissie came on the line and begged me to come as we hadn't seen each other since the wedding, that was settled then!

Eight O'clock on the dot finds me knocking on the front door, which opens to reveal a laughing Chrissie (already half cut) holding a glass of red wine. She squeals in delight (that's Chrissie for you) and gives me a hearty one-handed hug before dragging me inside and shutting the door behind me. By the sound of it I'm the last to arrive as the house is buzzing and rather noisy. I tell Chrissie that she is one swell looking lady in that little black dress, which only causes her to giggle all the more and informs me that my smooth tongue and an eye for the ladies hasn't changed one little bit over the years (if only she knew the half of it!).

The sound of our voices in the hallway attracts attention and Tom sticks his head round the living room door, shouts hello and tells me to join the crew in the living room while the ladies finish preparing dinner. I do as instructed and as I walk into the room I am greeted by a united "hello" from Mike, Aaron and Jason all trying to offer me a can of beer or glass of wine. Holding my hands up in mock surrender I take a can of beer and proceed to make small talk with them until dinner is announced.

Dinner (or rather a three course banquet) was truly scrumptious, for starters it was homemade potato and leek soup with croutons. Main course was roast duck breast served with a medley of green vegetables, rosti potato cakes and a rich port sauce. For dessert homemade vanilla ice cream marbled with dark chocolate and a raspberry sauce followed by the obligatory coffee and mints.

It was during the coffee round that attention turned towards me and I received a good natured grilling over my current job as a prison officer. I talked about my role and the inmates I came into contact with (without revealing their real names) and some of the incidents that I had encountered. I successfully managed to avoid mentioning the sexual nature of some of my encounters and the new prison rules etc. I also managed to avoid any reference to the fact that I was no longer 100% heterosexual in my thoughts or activities. After what seemed like ages the attention turned to physical fitness and finally Kirsty came out of her shell. She thanked me for taking Jason under my wing, although he has only just started his training with me she has already noticed a difference. He has started to eat more healthy food, drink less alcohol (this night being an exception) and has been religiously doing all of the exercises I had given him. She thinks in the right light she can make out muscles underneath his belly! This brings resounding laughter from all except Jason who pulls a hurt expression before throwing me a sly wink. Then Sally nudges Aaron and makes it clear that he has no room to laugh as his middle is beginning to spread! Tom regains control of the situation by expressing the fact that really all the guys in the room (except me, of course) could do with a little more exercise and less girth round their middle, perhaps Mike and he could join the rest of us on Sunday at the swimming pool and see how they get on. I thought this was a splendid idea, but what about the ladies though? By the end of the conversation we were going to be a group of eight in the pool on Sunday, I wonder if we can get a group discount?

I finally staggered in through my front door at about 1.30am (technically Sunday I know but I don't count it being the next day until I've been to bed and woken up again) and was all set to collapse into bed when I saw the rubber bulb waiting on the side for me. I ummed and aahed over it, thought sod it one day won't make any difference, then changed my mind and picked it up on the way to the bathroom.

I sat on the toilet and emptied out as best I could then greased my arse up and also the bulb. Perhaps it was the alcohol in my system or my deadened sense of time but it (the bulb) seemed to disappear up inside me more easily and quickly than I expected. It did have one unexpected side effect, it gave me a raging hard on as it gently rubbed and banged against my prostate from the inside. There was no way I could go to bed like this, so with one hand feeling the neck of the bulb and my ring clamping hard round it, and the other wrapped round my cock I jacked myself of to a pretty earth shattering orgasm over the bathroom basin. Deciding now enough was enough I really needed to get to bed I washed myself off (and the basin), pulled up the thong and made my way to the bedroom where I quickly succumbed to oblivion.

SUNDAY 11TH APRIL 2010

If I'm honest diary, today didn't actually start until about 11.45am when I woke with a jolt to the sound of my phone ringing about six inches from my ear – not a good way to start the day if you've got a little bit of a hangover....

I was just a little groggy when I picked up the phone and mumbled a hello down the line only to be greeted by the chirpy tones of Chrissie.

"Morning Sam! I just thought I'd give you a quick call to make sure you got home safely & that we're still on for the swimming session this afternoon. How's the head this morning?"

"Urrr morning Chrissie, I think, what time is it? Yeah got home okay and yes I'll be there at the leisure centre at 2pm as agreed! My head is still on my shoulders but feeling distinctly tender, I guess that will teach me to finish up that last bottle of red with you... how's your head by the way?" I asked as I came to, slowly.

"I'm just fine, thanks" Chrissie assured me "must get on, still got some clearing up to do before we meet up. As to the time, it's nearly mid-day. See you shortly, byeee!"

And then she was gone. Just as well she woke me up as I didn't have all that much time to get spruced up etc. First things first, into the bathroom to shower and remove a certain object. Crikey, my arse must be getting like a bucket because it's getting easier to take the bulb out, I didn't have to squat over the toilet and strain, I simply started to squat down and as I did so it popped right out with little discomfort. Curiosity got the better of me, I just had to assess the damage to my hole, not only did two finger slide right on up inside with no trouble but so did three! Progress indeed, I'm sure that Liam will be pleased. However I had no time to dwell, I quickly showered and shaved before getting dressed and packed my bag with my swimming gear.

I got to the leisure centre just before 2pm to find Jason and Kirsty waiting outside for me and the others; we made small talk and recounted the events and conversations from the previous evening. Throughout our conversation I monitored discreetly Jason's behaviour towards me, but he acted impeccably and not once did he act in anyway other than being Kirsty's partner, to my relief. Ten minutes later the others had arrived and we made our way into the changing rooms.

With the five of us (Tom, Mike, Aaron, Jason and myself) getting changed it was a very relaxed affair, even Tom seemed at ease and managed to joke around as we undressed and got into our swimming trunks. Privately I had to agree with Tom, both he and Mike were carrying a decent sized spare tyre round their middles. They will definitely need to go on a diet and exercise regime before they can join Aaron, Jason and myself jogging round the park on a Tuesday and Thursday. An hour later after a mixture of hard swimming and relaxed messing around in the water the eight of us are sitting round a table in the cafe overlooking the swimming pool. I was lost in thought when I felt a sharp nudge in my ribs bringing me back to the present.

"Well Sam, what do you say? Are you up for it?" Aaron asked with a slightly exasperated tone to his voice.

"Up for what?" I asked in all innocence.

"Having a last lad's night out this Friday before we cut out all the booze and grub as part of our diet and fitness regime" Tom explained.

"Yes, sounds good to me. Is it down the Kings Head shall we make it a special night and go into town?" I asked the group in general.

"Oh it's got to be town if it's going to be our last night out for a long time!" Jason cried out all enthusiastic like a big kid.

"That's decided then" Chrissie announced "girls we're going to paint the town red too! Kirsty and Sally, get your thinking caps on, we have four days to plan our night out."

Shortly afterwards the conversation naturally dried up and we went our separate ways.

MONDAY 12TH APRIL 2010

Back to work already, oh how the weekends pass so quickly. The alarm clock went off and I swung into action on autopilot, even removing the rubber bulb from its night time lodging in my rectum had become part of my routine. I hate to admit it but I could insert and remove it with ease....

At the prison I made my way directly to Richard's consultation room and knocked on the door before walking in to find that Richard was alone. He greeted me with a warm smile and explained that it would just be the two of us to start off with as Liam had been called away at the last minute but he hoped to join us later. With the preamble over we got straight down to business, I stripped naked and Richard cleaned me out thoroughly using the portable colonic irrigator. Then having climbed onto the couch, kneeling on all fours in the usual position Richard examined my anus to assess my progress with the rubber bulb. I felt him smear the Crisco round my hole and then fingers moving around the outside and inside of it. The movement was constant and I had difficulty keeping a track on how many there were and what they were doing, it all became a pleasurable blur.

"Well Sam, I can see that you have followed our instructions and the result is very pleasing indeed. You should be proud of your achievement, your progress is excellent." Richard announced as he withdrew his fingers from me.

"Thank you Richard, I must admit it was not easy at first but by this morning I really become accustomed to it and I was even finding its presence pleasurable in a weird kind of way. When you say I have progressed, by how much and what is the target you have in mind?"