The Retired Prison Spanker

I'm retired now, but when I was working I really liked my job. I loved it in fact. I had been a guard at the big prison, just outside of Edmonton, for more than eighteen years, and in that time I managed to work my way up, paying my dues and doing what I was told. For as long as I can remember I had had the goal, to be the one who gets to have the fun, to burn their bottoms and to make them glow. Yes, I've done that all now, and it was certainly worthwhile. God it was fun to be the one that swung the strap and paddled their rears. I loved doing it too, strapping the misbehaving prisoners until their bottoms were the color of ripe cherries.

Now, I never was the one who decided who got the strap. No, but when the prison rules were broken, and a prisoner refused to do what he was told and to do it immediately, then I often got to see them, as they were fastened to the table and their bottoms were exposed. It was always done on the bare, always, and so I got a good look at them, and their balls. I loved the way they would swing, once I'd started their strapping and after that they could only jerk within their restraints and bob their bottoms up and down. I loved watching them struggle, jerking and thrusting into the table as if it was a woman. Still, no matter what they would do, I would strap their bottoms relentlessly, and even though they wiggled them and jerked them and tried to move them side-to-side to dodge the blows, it didn't really matter. I would lay the strap on them just the same, one stroke after the other, piling them on top until their bottoms were crimson and they sang for mercy.

The punishment room was off the main cell block, through two locked doors and down the main hall beside the warden's office. It wasn't that big of a room, but it was big enough, and usually when I was doing a strapping there were at least six or seven people in attendance. I think they came to watch the show, to see the prisoner beg and squirm, thrusting his hips and swinging his balls. I was really good at what I did, and I had a well-earned reputation, so whenever a prisoner got sent to the table it meant something. All of the prisoners feared the strap back then, all of them, and that of course helped to keep them in line. If they screwed up, then I got to see them, and each time it happened I enjoyed every minute of it. It's a shame that it's not used anymore, but back then it was, and it did the job and the prisons were a lot safer than they are today.

The table we tied them to was old and worn, and had been a part of that institution long before I came there. The old leather cuffs were dark and well aged, and the leather was worn smooth from all the many men that had fought and jerked against their restraints, straining with every muscle to stop the onslaught they felt in their rears. The man's legs would be secured down one side, and were cuffed at the ankles to the legs on the table, so that his ass was on top, right on top and in the middle of that little table, where it was a perfect target for my strap. The man's chin rested on the other edge, with his hands secured on the other two legs, hanging down. He could lift his ass upward if he wanted, to the extent his bonds would allow, and many men did that as they tried to escape the blows. Oh how they would buck and jump! I've seen the entire table shaking on a really big man, as they jerked and slammed their hips and dodged the strap as best they could.

The surface of the table was worn totally smooth, as smooth as a baby's ass even. It wasn’t done with sandpaper either. No, it was worn smooth, over the years, from all the desperate movements of the many men that had been strapped to it. We would throw a towel down over it, before we would lash the prisoner down, so that if they messed during their strapping it was easier to clean up. I've seen some men piss their bladders as I worked the leather strap into their skin, and that was always funny and it did generate a lot of comments and certainly got everyone's attention. Of course, that was pretty rare. I'm glad most men held their piss, because even the towel couldn't contain the contents of a man's full bladder.

However, there are other messes that happened more often, and for those the towel was very useful. You wouldn't think it would happen, but it seems that many men, in fact, most men even, would mess the table if they were strapped long and hard enough. I guess it was the friction of their punishment more than it was anything else. They would fight, and as they did they humped against the table, dodging the strap and in so doing they would jerk their hips up and down.

Below them, for the majority of them, their cocks grew stiff in spite of the pain in their bottoms. Soon enough they were jutting under them, upward, and along their bellies, stiff and hard and oh-so-eager. As I would strap them they would thrust and jerk, struggling, desperate, to dodge the blows, and as they struggled their stiff cock moved under them, smashed into the table's surface and rubbing within the terry cloth towel. If they did that long enough, with enough blows to their bottoms, more than a few would actually ejaculate while I was strapping them. That always grabbed their attention, and when it happened I make sure to increase the speed, so that I was paddling their bottoms in a frenzy as they squirted their loads. When a man did that he usually grunted it out, embarrassed as it was happening, and when I detected it, which I usually did, I always intensified the blows and worked the strap up and down their naked bottoms even as they were pumping out their wads.

In the last few years, after I got good with the strap, if I was in an especially foul mood, or a particular prisoner deserved a special "treat", then I would work the strap with a twist of the wrist, bringing it up between their legs as they were squirting. As I did that, the tip of the lash would catch their balls, which were totally vulnerable and swinging beneath their legs. Most men would scream if they were shooting and their balls took a hit, and when that strap struck a swinging scrotum it made an impression that no man could ignore.

I remember this once when one of the younger, cockier prisoners was sent to the table, for throwing his food in the cafeteria. He was cute as hell, nineteen and with a muscled, well-toned body, and I remember his legs how they fought and jerked after he was on the table and feeling my strap. His asshole was oh-so-tight and ringed with his hair, which had grown down over his balls and upward, forming a thick patch over his thin teenage cock. Other than that, his chest was totally smooth, and except for the two little matching patches of hair under his armpits he would have passed for a much younger teen.

Oh how he screamed when he felt the strap! You would have thought he was dying from the way he yelled. I didn't give him any mercy though, and I'm sure it was a long while before he played with his food again. I strapped him and strapped him, and soon enough he was begging for mercy, his ass going up and down and wiggling side to side as he struggled and fought and begged. I never slowed the strap, but just kept it going, and of course as I did his entire ass got redder and redder. I think I strapped him for about ten or fifteen minutes.

We never used a specific number of blows when I was there, so it was all left to me and I did it by color. When their bottoms were bright red, cherry red, and they were crying and blubbering out their begging, then, and only then did I let up on them. They were almost never sentenced to a specific number of blows, at least not for in-prison transgressions. Instead, they were warned, and then if a warning didn't get their attention, then they just were told they had earned a strapping, and after that it was done and I was the one that did it.

Right away I would try and make them very sorry for whatever got them to the table. I usually got them begging pretty quickly, and I always tried to get an apology out of them as well. I was almost always successful too. The trick to giving a quality punishment was to show them no mercy, and so no matter how hard they would cry or beg or jerk, once I began it I just keep it going, blow after blow, criss-crossing that leather down and across their naked ass, up along the inner crack and even over their hole if I felt it was necessary.

I do remember some of them, perhaps from the way they looked or the way they yelled. I still remember that misbehaving food thrower, and the way I let the lash lick his hole, just flick-flick-flicking it there since I wanted the lesson to stick with him. The fifth or sixth stroke in that spot got him shooting, and after that he was grunting out his load as he screamed for mercy. His thin cock was off to the side, and the circumcised tip was exposed, jutting out under him, so as he shot his load it missed the towel and shot out under him instead.

I never stopped their spanking when they shot their wads. While I was hitting him his belly rubbed in his cream and his pubic hair mopped up his load as he squirmed and jerked and fought. I almost burst out laughing, as he grunted and yelled and ejaculated his teenage load. His cream shot out in lines of jism, and because of the angle of his prick they shot out under him, across the table top, and everyone watching watched as it happened. I think the kid was totally humiliated. By the time I finished the boy's face was as red as his ass; in fact they were both so red they looked like they had been painted.

I remember the first time I hit a man on his balls. I'll never forget the look on his face when he felt that strap. What I remember about him was that he was the first one, the very first one, where I decided to bring the strap up and into his nuts as I was doing his ass. I don't know why I started doing that, but it was so effective and it made such an impression that I just felt it was part of my job. He was a really big man, a hell of a man, who was in his late thirties and was one of our biggest troublemakers. I had seen him around, and he was a bully, always picking on the new prisoners. Whenever one of the younger ones came into the institution he would chase them like they were a woman. Plain and simple, he liked to fuck the boys.

I had strapped him before, for another thing, and after I had finished that first time and his ass was red he had laughed as they untied him. Yeah, even after I had finished he hadn't been really fazed by it. Knowing that, I knew I had to do something else to make sure he didn't laugh at me again. Finally, I got my chance, when he took his liberties on one of the young prisoners. The warden had had enough of him too, and when they dragged him down fighting like a maniac to the punishment room he told me to give it to him good. So, I strapped him for the rape. Needless to say, I laid it into him without mercy.

His balls were big, really big, and swinging, and as I was strapping his ass I couldn't take my eyes off of them. They just made a hell of a target, and he was so arrogant he started laughing as I was hitting his ass. So, well, I just let the strap slide upward, between his legs. He wasn't arrogant after that! No, he yelled so loud then and bucked his hips, that I knew I was getting to him and after that he was mine! He was so shocked! After that his nuts started swinging as he jerked and jumped, and as they swung I got into the rhythm of it. So, at least every second blow I just let the strap kiss them as they swung. He was screaming like a banshee then, a terrifying inhuman scream that seemed to echo through the room and carry down the halls. He fought so hard! His ass was big, and made a hell of a target too, and I painted it with the leather until it glowed.

He was the first one I ever hit on the nuts. It wasn't every blow, and his ass was still the main target. Still, since he was on the table for rape, I snap-snap-snapped that leather strap right into his balls and at full force too, getting his big sac swinging as I laid that leather into them. He jerked and pulled inward with his knees, trying desperately to close his legs together and to protect what made him a man. I didn't care; he was well tied and he was exposed and oh-so-vulnerable. I liked watching his naked ass go up and down. I just never let up, and I blistered it, letting the holes in the strap do their damage as I worked the leather and flicked my wrists. He was bucking like a madman, and his thick cock could be seen whenever he raised his ass upward, high in the air, and jerked against the restraints. As his bottom would come up I would strap in between his legs, even catching his big dick on occasion. He didn't like that! Still, he deserved it, and so he got it, and as he babbled out and begged for mercy I had to stifle my laugh.

The last boy he had assaulted was allowed to watch. That was the warden's idea, and it was a good one. So the teenager was in and watching as the big man took his hits. The boy was new to the prison system, in for grand theft, and so it was a good lesson for him and served to keep him in line in the years that followed. I had the boy stand so that he was looking right into the face of the man who had raped him, so he could catch his expression and see what the strap did to him. As the boy watched his assaulter being punished I noticed that it made him hard. I never let up, and never slowed the pace of the strapping. The man's big ass got redder and redder, and was soon glowing like a cherry tomato. Still, I kept it going, smack-smack-smacking the leather into his nuts too when it seemed appropriate. Before I was done, he was gasping, and as he slammed his big hips up and down the entire table jerked, bouncing as he screamed and fought and grunted.

Before I was finished with him the big man ejaculated, shooting his mess into the towel. He was grunting out as he shot, squirting out his man-load as we all watched him do it. As he emptied his balls I laid the strap up between his legs, so that the curve of the leather went clear across his scrotum, from underneath, and curved upward to catch the base of his cock even as it squirted. I flicked it there several times, one after the other, and the end of the leather kissed the tip of his dick as I did so. That made him buck his hips even more as he gasped and begged and with a look on his face of total disbelief. Soon, he was just screaming, yelling out words as he begged for mercy in an incomprehensible blabber. The boy, watching, was grinning then, relishing the misery of the man who had dared to fuck him.

The prison strap I used was standard issue, and was used in most of the Canadian institutions. It was two inches wide and eighteen inches long, with holes running straight down the middle. The leather was attached to a wooden handle, which was well worn, as was the leather. It was designed to hurt, and it did do that and always made an impression. I never did see a man that could ignore the burn, as it was intense and deep and over time it consumed their soul. I was good at using it, and I knew how to make it go where I wanted it too. With the right flick, you could twist the tip, causing it to curve upward or downward, kissing a scrotum or popping a hole. I loved hitting a man directly on his asshole, and as the ring of muscles reddened the man would always scream and fight it, the feeling more intense than anything he could ever have imagined. No wonder they would do virtually anything to keep from seeing me again!

I almost always enjoyed punishing a man. Almost always, but there were some exceptions. Sometimes the prisoner I was told to punish looked a little too young, or perhaps undeserving, and those were harder to do well. Still, it was my job, and if they were brought to the table for me to punish then I would do it. There was this one time when they brought in a boy, who was crying already before I ever picked up the strap. He was just barely seventeen, a kid really, and he looked so young and so innocent it was hard to get into his punishment. He was there because a robbery had gone bad, and a man had died, and even though he hadn't had much to do with any of it he had been there and he had been a part of it. So, there he was, in a man's prison, when he probably deserved to be in a juvenile facility or even out on probation instead.

He had spit on one of the guards, and that had earned him the table. I don't know...the kid seemed so damn innocent. His unkempt blond hair was long, and he had a wisp of a mustache trying to sprout. He wasn’t even shaving yet, not really, at least not daily. His armpits hardly had anything growing there, and for a minute I thought he had shaved them, before I finally saw the few strands and realized he was still in the middle of his adolescence and his blond hair had only recently begun to sprout there. Even his sac of nuts was small, just boy-nuts, hanging below him and oh-so-visible between his stretched out legs.

I probably wouldn't have done much, except the guard he had spit on was in the room too, and because of that I had to do what was called for. As soon as I started swinging the strap the boy just howled, and he bucked his hips then in a frenzy, up and down and up and down, jerking his teenage bottom that was oh-so-cute. The kid had a nice bubble-butt, and as he bounced it up and down he would raise it high in the air in his desperation. His cock was young, a thin boy's cock that seemed to jut out from him like an eager little pole. Still, he was a teenager, and well enough into manhood, and his cock did grow hard and after that it looked a little more substantial, especially as it was jutting out from his little patch of pubic hair.

Thinking back I'm sure he was a virgin. Yeah, I'd be very surprised if he had ever had a woman. Still, he bounced his ass up and down, almost as if he was fucking something, and as I was watching him do that it I remember that it occurred to me that it would be many years before he would get the chance to do it for real. I strapped him and his bobbing ass, and as I did the boy just fucked that towel, literally, and grunted as he did it. I slowly worked the strap over the cheeks of his ass, and after a while they turned pink, and then finally red.

He was crying and bucking his hips, and he shot his first wad after only a few minutes. We all saw it come out, as it was shooting down into the towel when his ass came up high. It was a typical teen boy's wad really, mostly clear, and watery, and yet he squirted it out with an intensity that only a youth can deliver. At the time it seemed such a waste to me, meant for a girl and squirted into a prison towel instead. He was at the prime age when he should have been discovering girls, fucking his first pussy and becoming a man. Instead, because of a mistake and a few bad choices, he was tied to my table and humping it instead, squirting out his teenage load while a group of men watched him waste it. It just seemed so wrong! Still, I had to keep the strapping going, because his bottom wasn't red enough then, and so I did, hitting his bottom again and again as he screamed and bucked and struggled and shot.

All the while he was oh-so-sorry, apologizing, and I finally just stopped because I felt the kid had had enough. I asked the guard if he would agree that the teenager had learned his lesson, and I pointed out that he had been blubbering out his apology the entire time. Unfortunately for the boy, the guard shook his head, and said "No...I want to see his ass RED, and it's barely pink now! GET ON WITH IT!!!!"

So, well, I had to lay it into him then, painting the boys bottom as he humped it up and down. A few minutes before I was done the boy shuddered and shot a second wad, just ejaculating it into the towel as he gasped and screamed. His eyes were so wide! His back glistened with his sweat, and his hair darkened as it grew wet. The boy was shaking after that, just shaking and begging, and I was actually relieved when his ass finally turned tomato red and I could stop. When they took him down I looked at the towel and the boy's two wasted wads that he had shot there one after the other. His teenage spunk looked out of place, and it occurred to me that there were many girls his age that would have willingly spread their legs and allowed the boy to shoot it into them. Of course, by the time he would get his chance he wouldn't be a teen anymore and that would no longer be true. Oh well. As I stared at his wads of wasted goo, it made for a hell of a thought. I can still remember him like I did him yesterday.

As I said, normally we didn't count the strokes, but instead just spanked them until their bottoms were the right color. Sometimes it might be twenty strokes, sometimes more and more often, less. The only exception to the no-counting policy is when a prisoner came to us with a court-ordered strapping as a mandated part of his sentence. I didn't especially like those, but of course I did them when we were told to. Usually they had a sentence somewhere between twenty and one-hundred strokes, with half to be delivered within the first two weeks and the other half to be held to the end, after they had served their time. The second half usually had to be given within the last thirty days. That always seemed cruel to me; to get whipped on arrival is one thing, but then to wait, as the months or years go by, for a second strapping, was always extremely difficult for them. Once a man had been strapped, the fear of it being done to him again would often tear apart his soul. The worry just ate them up, and soon enough it was all they could think about.

The double strapping sentences did serve a purpose though. The second half that was mandated was usually at the warden's discretion. Of course, the warden soon let it be known that if the man was "really" good, and did "exactly" what's he was told to do, then the warden would take that into consideration when it came time to give him his final strapping. Of course, there were never any promises given, but even so, it offered the opportunity for the prisoner to partially control what was going to happen to him. It was something they could hope for, and for many a man it was that hope that got them through. They always behaved themselves, thinking that if they were "extra good" then they might get out of the pain they otherwise knew with certainty was awaiting them.

In reality, most prisoners that had a split sentence got their bottoms burned before they left anyway, regardless of how they did their time. The reason was simple enough, because the nature of the crime that got them strapped in the first place usually wasn't the type of crime you would want to let go only partially punished. The last man, that finally forced me to retire, was one such example. Of course, I can never forget him! He first came to us with sixty strokes times two a part of his sentence. It turned out he had abused a young teenage boy, a lad of just barely thirteen. He was just a neighborhood kid, and the man had lavished gifts on him until he had finally made his move and forced his dick down the boy's throat. He did it more than a dozen times before he was caught, splashing his wad of jism into the kid's tonsils as he laughed. God he made me sick!

The judge was less than pleased too. They should have locked him up for life. However, since the man was a "good citizen" in the community, and this was his only trouble with the law, ever, the judge has been restricted on what he could do. It turned out the max he could give him was five years. So, to avenge the abused boy, and to send a lesson to others, the judge sentenced him to the maximum sixty months, but then added a second sentence for sixty strokes done twice, with the first sixty given within thirty days and the last sixty to be given at the end of his jail time. He was one prisoner that I wanted to strap, and because I despised him so much I'm sure it was part of what led to my downfall.

I still remember when I saw him, and thought about what he had done to that kid. I remember wishing I could just pulverize his rear, and I remember thinking he deserved a lot more than sixty strokes of a piece of leather. Still, it was a pretty stiff sentence. Usually when we had to do that many we would it on two visits to the table, about a week or so apart, but for some reason we gave them all to him in a single session. I just hated him, for what he had done, so I'm sure that was part of my reasoning. I do know for certain that as soon as I saw him I was looking forward to giving him his first strapping. One thing I was pretty sure of, was that no matter how good he was in prison, he'd get the other sixty at the end. I remember smiling as I had that thought. I was wrong of course, but I didn't know it then.

As it turned out, once was enough, even if he did get out of the rest of it afterwards. Yeah, he was the last man I ever strapped, and of course I wish I had done it differently. Well, at least he got what he deserved.

He sure didn't like that strap one bit. Just before I started giving him his sixty strokes, he had been so confident and arrogant that he acted like sixty lashes wasn’t going to be that big of a deal. When they had him secured to the table he started cussing at me as soon as I entered the room, and he was cocky and it pissed me off even more than I was already. I gave them to him, all sixty at one time, as hard as I could and without any mercy what-so-every. His mood changed right away! Oh how he screamed when he felt that leather! He shook so hard that the entire table rattled, and I slammed that leather into his ass and across it, flick-flick-flicking the end of the leather right against his hole, stroke after stroke after stroke.

I really wasn't thinking. I just let that strap speak for the boy he had abused, burning it into his soul, and as I was laying it into his ass the welts that I made were ugly. I've never seen a man so shaken as he, as soon as he felt the burn. I don't think he had any idea that anything could hurt that much, and so when I slammed that strap into his bottom he screamed like there would be no tomorrow coming. He just couldn't believe it.

The entire time I was doing it to him he was begging, ranting and raving about how sorry he was and how he would do anything if we would only stop. As his legs were spread wide, the way they are when they are tied right, when he raised up his ass I could see his entire sac of nuts. The man had a huge sac of balls, really fat, and as I looked at those big balls and thought about him empting them down the kid's throat I just got madder and madder.

His thick cock was jutting out, under him, and I imagined it rammed down the young teen, shooting his wad as the boy gagged on it. I knew from the size of his balls that he'd shoot a big wad, and the very thought of the young kid being forced to drink it, his mouth stuffed with man's big prick, just pissed me off in a way I can't describe. So, I know I stared at it, and watched him as he slammed his hips up and down and pushed his cock into the towel that was waiting under him. I knew right away he was going to squirt, and the thought of him getting any pleasure, even if it was just from a towel, just wasn't acceptable to me. I hate pedophiles, and so I made him pay.

I had never struck a man quite the way I struck him then. I lifted the strap way up, and as I brought it down fast I did it with an underhand movement, moving the leather in an upward cut, right up between his legs, the strap snapping with a vengeance into the bottom of his big sac. Each time I did that his balls took the full force of the leather, with the tip snapping, moving so fast it was blurred, and I laid into it with perfect precision. I didn't hit his nuts with every stroke, in spite of what was said later. I'd crack the strap into his bag, and then on the next stroke I'd come down, across his ass, sideways, making a welt that rose up like a railroad track. Next, I'd come straight down, across his hole, burning the tip of the leather into it until it was puckering, swelling even, puffed up and oh-so-red.

Still, it was his fat sac of balls that held my attention. So, I'd go back to the man's big scrotum at least every third stroke, each hit literally lifting his balls with the leather as I laid it into him stroke after stroke. Back and forth, from one direction and then the next, down and across his naked buttocks, the leather strap painting lines of bruised skin with every stroke. After that he stopped talking, at least with words that were understandable. Instead, he just screamed and screamed and screamed, bucking his hips and screaming, literally, like a crazed maniac.

What I didn't know of course was that the strap ripped his bag. From the angle I was standing I had no indication, other than the intensity of his screaming, and so when that leather split his scrotum I didn't know it. I don't know when his testicles actually fell out, but I do know that I would curve that strap between his legs and strike it up and into his bag with all the strength I could muster. Eventually his balls were just hanging by their cords, and so when the strap hit them then full force there wasn't any way they could survive it. I guess he squirted into the towel as I castrated him.

I saw him shuddering, as he was cumming, and when I saw that I remember that I just laid it into his sac blow after blow after blow until the thing was an empty flap of skin. I just wasn't looking at it that closely, and so I didn't see what I was doing until it was done. By the time it was ended and the sixty strokes were finished, he was a babbling maniac, crazed, just struggling and fighting with a desperation that can't really be described.

Of course, as they dragged him off the table he just collapsed, and that’s when we saw it then, the blood under him and his last and final wad wasted in the towel. His balls were gone! The strap had just split his sac wide open and then turned them into mush. Only the end of his severed cords were visible, hanging out of his empty scrotum, and I remember as we saw that I knew I was in big trouble. I had castrated him, and there wasn't anything the prison doctors or anyone else could really do for him to change that fact.

Of course, I was in a hell of a lot of hot water, and so I put in the papers and retired as fast as I could. The warden approved it right away of course, to get me out of there before all hell broke loose. Luckily, they didn't come after me, and so I got lucky there, even though I would have rather stayed and kept swinging the leather. As far as the man I nutted goes, well, I heard that eventually they had to pay him something, although it didn't get him out of his sentence. They never let him out until he had spent his five years there, although by the end of that the punishment room was already history.

I had hoped they would strap the eunuch before he left, but of course that never happened and by then they weren’t strapping anyone anymore. Still, he paid. I learned the other prisoners were merciless on him, and he spent most of his time with his legs spread and his limp dick hanging free, feeling his ass as the other inmates filled it with their loads and used him as a woman. I do know that he was forced to suck a lot of cocks while he was there, and so in that sense I guess he got what he had given.

What can I say? I like being retired, and I have my memories and I will relish them forever.

[Authors note: © Copyright October, 2003. All rights reserved. Not to be copied without the consent of the author. [email protected]]