The choice is yours

Jason and Chris stood awkwardly, hands behind backs, eyes downcast. The principal was mad – if not, he was a pretty good actor.

“Senior boys acting like juniors!” he raged. “Fighting in the corridors!”

Jason looked at his partner in crime through the corner of his eye. “Too true,” he thought. “And if that faggot looks at me that way again, I’ll cripple him.”

Principal Golightly rose from his chair. He was an elegant man in his fifties, with premature silver hair. He was lean and fit, which is more than could be said for most of the other teachers at Rosewood College. Golightly took care of himself.

He ambled across his office and stopped by the far wall where his eyes ran along the shelves as if he had never seen his books before. Jason hopped from one foot to the other. His legs were tiring. He wished Golightly would just get on with it. What would it be? Detention? An essay? Why it is wrong to settle our differences with violence – a title like that.

Golightly turned his attention away from his book collection and faced his two eighteen-year-old students. He paused, weighing his words carefully. “I shall give each of you a choice,” he said, his voice sonorous. He paused again as if for dramatic effect. He had both teens’ attention. “You may take swats or attend Saturday morning class.” He paused once more before reiterating, “The choice is yours.”

He delighted at their shocked expressions. Jason’s eyebrows arched. Principal Golightly could read the boy’s eyes. “What the fuck?” they said, but Jason himself remained silent. Chris was the first to speak. “It’s against the law.”

I am the law at Rosewood,” Golightly drawled. He delighted in the ensuing silence as Chris’s face blushed scarlet.

“Well Manor, what’s it to be?” the principal stared intently at Chris although he already knew the answer. What eighteen-year-old would submit himself to the principal’s paddle. Taking a spanking was beneath their dignity.

“Saturday detention,” Chris croaked, and then after a beat or two, he added the obligatory, “Sir.”

Principal Golightly’s nose wrinkled. He turned his attention to Jason. “And you Taylor?”

Jason mind whirled. Saturday morning detention. No way. He had discovered a neat little bar off Main Street where the university girls went. Jason was five-feet-ten, with broad shoulders and trim waist and the most beautiful ass. The girls loved him. He could have his pick. He would be screwing some girl on Friday night and be in no fit state for school on Saturday.

His choice was not as the principal put it. For him it was not detention or the paddle; it was sex or no sex. A no brainer. Jason took a deep breath and as confidently as he could, he said, “I’ll take the swats, Principal Golightly.”

The principal hoped he didn’t look as astonished as he felt. This hunky eighteen-year-old was prepared to offer up his ass to the wood. To let a much older man blister his buttocks. Well, well, well, he thought, and he had supposed that Chris Manor was the gay boy here.

Principal Golightly straightened his shoulders. “Very well,” he intoned imperiously. “Manor, you should leave us.” He needed no second telling and within seconds Chris was on the other side of the door. Realising he was quite alone in the corridor, he put his ear to the door.

Inside the office, Jason stared ahead, determined to go through his ordeal with some dignity. He had never been paddled before; nor to his best recollection had he been smacked. Not ever. Not even as a little kid.

Principal Golightly walked slowly across the office to a long, narrow table. He delved his hand into his pants pocket and found a key. Jason watched intently as the silver-haired man unlocked the drawer, opened it, reached in and withdrew a heavy wooden paddle. It was awesome; easily eighteen inches long and maybe four wide. And drilled into its blade were a dozen holes. Jason wouldn’t know this (not yet, at least) but the holes were there to combat wind resistance and make the paddle fly faster through the air. The holes would also add to the blisters that he would carry on his backside for some time to come.

Principal Golightly caressed the wood, rubbing the tips of his fingers along its entire length. It was as if he had never before seen it. Then, he tested its weight and seemingly satisfied, he held it in his right hand and smacked it firmly into the palm of his left. Jason watched transfixed. It needed little imagination to conclude this was a mightily effective punishment tool.

“Put that chair in the middle of the room,” Principal Golightly nodded to an ordinary office chair. The command startled Jason and at first he was unsure what had been said. “That chair. There.” The principal waved his paddle at an area of rug. Jason fully awake now took hold of a small straight-backed chair. It was very light and he had it in place in no time.

Principal Golightly caressed the paddle some more. Jason watched him closely. The old man seemed to be contemplating. Was he having a discussion inside his head? Perhaps he was, and very soon Jason discovered the outcome of the interior dialogue.

“Stand in front of the chair.” Jason did as he was told. Why was his heart thumping? The palms of his hands were sweating too. “Now take down your jeans and bend over.”

“What the …” Jason’s mouth formed the words but no sound passed his lips, but his astonished look spoke volumes.

“Take down your jeans,” Principal Golightly repeated, slowly. “They are far too thick,” he said. “Besides, you are a senior boy and you deserve a senior boy’s punishment,” he added, but immediately regretted it. He owed this boy no explanation. He was the principal of Rosewood College, one of the most prestigious educational establishments in the state. He answered to nobody.

Jason blinked hard. Jeans down. Stand there in his underwear. And he thought Chris was the faggot.

“I am waiting,” Principal Golightly, intoned. “Or do you wish to change your mind and take Saturday School,” he sneered. He knew Jason would not back down. His pride would be hurt.

The eighteen-year-old bit his bottom lip and with fingers that trembled more than he wished, he unbuckled his belt. He felt the principal’s glare burn into him as he fumbled with the metal buttons and allowed the front of his jeans to fall open. He paused, summoning the courage to go further.

“Take them down. Right down. To your feet,” Principal Golightly waved his paddle menacingly. Jason released his hold on his waistband and the jeans slithered over his thighs and down to his knees. The weight of his belt and the denim cloth took them further south where they puddled at his feet.

Principal Golightly’s eyes shone. The teen wore rather old-fashioned white cotton briefs that were tight enough to demonstrate to him that Jason was no boy. “Bend over. Take hold of the seat of the chair. Make sure you stick your bottom out.”

If looks could kill. A mixture of contempt and defiance clouded Jason’s usually bright, open face. He turned his back on his tormentor and in one swift, athletic movement he positioned himself to perfection to receive paddle swats.

Principal Golightly took the paddle in his right hand, stood close up to the boy and tap-tap-tapped it across the centre of Jason’s rear end. The term “buns of steel” might have been invented for the boy. His muscles stretched to present a solid target. There was no “give” anywhere. The principal lifted the heavy blade away from the cotton-covered ass and with all the strength he could muster – which was considerable – he returned it at speed pounding it into the proffered buttock cheeks. The crack!! echoed around the office. Its intensity startled Chris who stood on the other side of the door. He heard Jason’s startled yelp as the pain shot through his buttocks and raced up and down his legs. Chris touched his own backside with his fingertips in an involuntary act of solidarity. His dick stiffened.

Inside the office the paddle rose and fell once more. Now, every square inch of Jason’s buttocks seemed on fire. He wriggled his hips, stomped his legs and gripped the seat of the chair as if his very life depended upon it. Principal Golightly pressed his left palm firmly into the small of Jason’s back to steady the boy. He was going nowhere; not until the principal said so. Swat three landed lower and a red mark imitating the paddle blade instantly formed on the back of Jason’s thighs. His wailing was terrific. He did the wriggling and the stomping thing again and this time wrapped his left foot around his right ankle in a desperate bid to stop himself from jumping up to rub away at the terrifying agony. It felt like Principal Golightly had poured boiling water over him.

Tears flowed with the fourth swat. Jason despised himself, but the tears and the wailing were his body’s way of coping with the enormous battering it was getting. He gripped the chair’s seat and waved his head backward and forward, rather like horses do when they neigh. Snot dribbled from his nose, his heart raced and it felt like blood would burst through his ears.

“Last one,” Principal Golightly announced quietly. He pushed his left hand firmly into Jason’s back, steadying the teen. Then he raised the paddle high and with tremendous force landed it across the underside of the cheeks. Bam!! He let go his grip and Jason shot to his feet jumping up and down rubbing furiously at the seat of his briefs, tears soaked his cheeks. He hopped from foot to foot  in the traditional spanking dance. Principal Golightly pretended not to notice Jason’s dick has swollen and was staring against the front of his tight cotton underpants.

“Get dressed.”

Jason pulled his jeans up, wincing as the heavy denim rubbed against his scorched flesh. Soon he had the belt securely fastened.

“You should leave now,” Principal Golightly spoke softly, “And no more fighting.”

Jason hobbled to the door, opened it with shaking hands and exited. The corridor was empty, he did not know it but Chris was at that moment locked in a lavatory cubicle furiously jerking off. Jason ruefully rubbed at his rear end. The agony had gone, replaced by a dull ache. Within fifteen minutes or so that would become a tender throbbing. The pain would disappear quite quickly, but Jason did not yet know that it take until after the weekend for the bruises to disappear. Friday would be devoid of sex after all.

z used paddle white pants chair office

Picture Credit: Man’s Hand Films

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Charles Hamilton the Second

The boy in the front row

used drawing paddle hold (5)

I am quite alone. The door is locked from the outside, it will not be opened until morning. Soon the light will go out, plunging me into darkness. My eyes are awash, but tears are not yet falling. Someone seems to have put my temples in a vice.

Let me try to explain what is happening. I am (sorry, I was) the headmaster of C_______________ College, the most upscale school in this part of the world. You will have heard of it; old money and tradition.

I first saw John in my English class. He is eighteen years old and a new boy. That is not unusual. We often take brilliant young scholars for a year and prepare them for a top university. John aced every test there was in his state. He is destined for great things.

It happened in the third class of the semester. John always sits at the front of the room. He reads voraciously and answers my questions with a confidence belying his years. He has his hair cut military style but has an unusual habit of running his fingers across his scalp as if he had long, flowing locks. Perhaps his crew cut is recent; a new look to go with his new life at school.

He has the most piercing green eyes I have ever encountered. They sparkle when he thinks. They are set symmetrically either side of a button nose, which hovers above slightly crooked lips. When he smiles he exposes uneven teeth. They are not tombstones, but they reflect his family’s lower income status. John is most certainly a scholarship boy.

What is it about those damn eyes? They began to haunt me. Almost literally. I dreamed of the boy night after night. As I recall nothing much happened, but he was constantly in my thoughts, beguiling me. I have a drink problem – there I confess it – but it wasn’t the wine that drove me forward. Indeed, most unusually for me, I had not touched alcohol all day.

Don’t ask me why I did it, I still don’t know the answer to that. I could have understood it had I been rip-roaring drunk. I had asked my secretary Mrs. Crabbe to bring me Mr. McAlpine’s file – we are always so formal when referring to our students. I found the number of his room at the boys’ dormitory and set off just before lights out. My wife has already gone to her bed in her own room. When did we start sleeping apart? I can’t be certain; sometime after our only son went off to the war, I think.

It is quite a trek from the headmaster’s house, through the quadrangle, and across the playing fields to the outlying buildings that comprise the dormitories. Boys and girls are kept separate, of course. It is not usual for the headmaster to visit the boys’ dormitories, but not entirely unheard of. Mr. Albertson, the dorm master, seemed a little flustered when he saw me approaching the building, suspicious perhaps that I had come to spy on him. I don’t know what goes on in the boys’ dorms at night and it would probably be injudicious to inquire.

John’s room was on the third floor at the far end of a corridor. His door was ajar and he was alone. He lay on his bed reading a book. He wore only khaki shorts, adding to his general military appearance. He looked up from his book as if he had been expecting me.  He smiled, those eyes dancing. Quietly, I closed the door behind me.

John is short for his age, I think. Maybe five-seven or so. His waist is narrow and his chest broad. I suspect he uses the gym. His torso is hairless, but a fine down covers his legs. He wriggled to a seating position and reached over and set his book down on the nightstand. It was then that I noticed the whisky bottle. My, how I wanted to grab it and glug down its contents. John saw that I had spied the bottle. His crooked lips parted.

It is against the rules for students to have alcohol. The penalty is strict: expulsion. John knew that, but I reminded him all the same.

He ran his fingers through his almost non-existent hair. I watched the muscles on his arms tense. He gazed at me. “Oh,” he said, “Couldn’t you just paddle me instead.” My jaw must have dropped, or at least I gaped disbelief.

“Paddle me.”

I cannot explain what happened next. That is, I can describe what happened, but I am still unsure why it happened. I am the headmaster of C_______________ College, I am fifty-five years old and have been around young men my whole life and have never given their bodies a passing consideration. I pull him toward me awkwardly, clumsily, unannounced. I am about to do something that will change my life forever. It will in all inevitability be my ruin. He is in my arms and I kiss him forcefully on the mouth.

But, John does not retreat from me; he kisses me back. Passionately. My hands run across his scalp, it feels like petting a hedgehog. Our teeth meet, tongues grope for each other. I run my hand over his warm, smooth naked flesh. My erection presses against the front of my underpants.

Then the lights go out and we plunge into darkness. The boys’ dorm can be like a prison. It is ten-thirty and all must be in bed. John gently pushes me away. I must leave. It would be unseemly for the headmaster to be caught in the dark in the bedroom of an eighteen-year-old male student.

I fumble for the door and as I leave I whisper, “My study, after school tomorrow evening.” It is a rendezvous with the paddle.

We haven’t used corporal punishment at the college since my father was headmaster. He was a devotee of the paddle, but once he retired it fell into disuse. Times, I suppose, have changed. The boys in the athletics clubs continue to use it. I believe the rowers especially paddle each other’s rear ends when they lose a race, which, now I come to think of it, is very often.

We still have my father’s paddles in storage and it is no problem for me to blow the dust off one of them. I have a fretful day. The college governors are in town and I am forced to sit through interminable committee meetings when all I want to do was stroll through the campus in the hope of catching a glimpse of my beloved John.

At last, the afternoon draws to a close. Mrs. Crabbe is tidying her desk when he arrives. She passes me a quizzical look, when she announces Mr. McAlpine is here to see me. Mrs. Crabbe keeps my diary and nobody, not even the chairman of the governors himself, gets to see me without her say-so. Why do I feel like a naughty boy found out in some misdeed? I croak that she should leave; her services are no longer needed.

I wait until from my study window I see Mrs. Crabbe pass through the quadrangle and then I order John into my study. It is a huge room befitting a man of my status at the school. At one end is my desk and cupboards for my official paperwork. At the far end are leather armchairs, a small table and bookcases. I order John to stand close to a chair. He does so without a murmur.

He is dressed in a blue jacket and cream chinos which passes for the school uniform here. His white shirt is immaculate and a wine-coloured tie is tightly knotted at his neck. His face shines. I imagine he is having second thoughts. But, it is his idea to be here. He could face expulsion and disgrace. I am sure his impoverished parents are extremely proud of him. They would die of shame.

I had placed the paddle in a drawer. I didn’t want it to attract attention, not with Mrs. Crabbe snooping around. I remind John of why we are here. He chews his bottom lip. My heart skips a beat. I want to pull him towards me and put my tongue down his throat. Instead, calmly I open the drawer and pull out the paddle. John’s eyes widen.

And, so they might. It is an awesome specimen. It is more than two feet in length and maybe four wide. Large holes have been drilled into the blade to reduce wind resistance during the swing. John appears to be sweating. His eyes follow my movements when I hold the paddle by its handle and smack the blade into my left palm. I have never spanked a boy before, but I know that this wood is capable of inflicting great pain.

“Take off your jacket, put it on the table,” I have decided he should put himself across the back of one of the leather armchairs. It is low and his buttocks will be presented perfectly. He slips the coat from his shoulders and folds it neatly on the table. The tail of his shirt is poking out of his chinos. I see they fit him tightly at the waist and a fold of cotton covers his buttocks snugly, separating each cheek.

I tap the paddle against the back of the chair. “Bend over.” I say this calmly although my heart is racing and my palms sweat. He gazes at me with those intense green eyes. I flinch a little. Then he does something truly remarkable. He moves into position behind the chair, unfastens his trousers and sends them to his ankles. He is wearing sparkling white boxer shorts. His fingers pinch the cloth at his hips and with the merest flick of the wrists he sends them south to meet his chinos. He swallows hard and bends over.

I have never seen a man’s bare arse so close. His cheeks are smooth and as bald as his torso. His ballsack dangles and I see it too is hairless. His flesh tautens as he stretches over the leather chair. He keeps his head low and his legs apart. I feel that this is not the first time he has submitted himself for a spanking.

I had been dreaming of this moment all day. Except in my version I am paddling the seat of John’s chinos. That in itself is an erotic vision that has my cock tingling. The sight of the eighteen-year-old’s naked buttocks has me hard. I lick my dry lips, take up position a little to John’s left and gently tap-tap-tap the wood against his flesh. His cheeks clench a little. I raise my arm away and bring the paddle down with a resounding crack! I am please Mrs. Crabbe has departed for the day since surely she would have heard the noise and come running.

A dark pink imprint of the blade immediately appears across John’s bottom. It looks sore, but John makes no fuss, his face buried in a cushion. I make another mark, this time on his other buttock. The flesh wobbles. He feels that.

I put the next two swats in the underside of John’s cheeks. His knees buckle and he hangs on to the chair as the pain mounts. I admire the aesthetic effect the paddle has on his once creamy white flesh. By the time I pound home swat number five, some of the pink blotches are turning mauve. The imprint of the blade has been reproduced several times. No square inch of flesh remains untouched.

I appreciate the look of the teenager’s buttocks as increasingly they are battered, but (and I am very nervous to discover this) I also relish the fact that I am hurting him. He squirms with each successive blow and clenches his fists and shuts his teeth. Despite his best efforts he yaps like a dog when I hammer home numbers nine and ten.

I had planned to give him ten swats but I am loving this so much I whack home an additional two.

“Stand up,” I croak, as my mouth is as dry as a desert. I realise the back of my shirt is soaked. My hands are shaking.

John bounds up, his buttocks are sore and so is his cock. It points to the ceiling as he hops from foot to foot and kneads the raw flesh. I find myself staring at his dick and look away fearfully, catching John’s eyes. I think I can read his thoughts. I am on my knees sucking his hairless balls. He spreads his legs and takes hold of the back of my head, urging me on.

“Take it all,” he cries.

Then I have John’s entire shaft in my mouth and throat, squeezing my lips tightly around the base of the eighteen-year-old’s cock.

“Argh, that is so good.’’ John’s fingers dig deep into my scalp. The scratches will be sore for hours.

John gives a low groan, “I’m cumming,” he gasps. I don’t heed the warning. My head continues the  rhythmic up and down motion on John’s rock solid cock. It throbs and I feel spurt after spurt of sticky cum being pumped up his shaft into my hungry mouth.

John pulls away. I don’t see what happens next as I am lying on the floor in the foetal position choking. Should I spit or swallow? I have visions of Mrs. Crabbe’s disapproval as she inspects the stained carpet. That is a humiliation too far; I swallow.

When I look up John has his underwear and chinos back on. He picks up his jacket and without uttering a word, he leaves my study.

I do not see John for three days. The absence is agony. I crave for his body. I need to understand what is going on. He misses my next English class. Is he punishing me? I need to know.

In despair and with half a bottle of whisky inside me, once more I go to his dorm room. He is on the bed wearing the same shorts as before. He looks up from his book as I enter, his look of distain is profound. I mumble incoherently. I am more drunk than I realise. I think I say something about love, or at least lust.

He sneers. Yes, really sneers. He an eighteen-year-old student and me the headmaster of one of the most prestigious schools in the land. But, the humiliation has only just begun.

“It’s a list,” he says, trying to explain what is happening. “Things I want to do once,” he is still lying on the bed but rests on one arm. “Get sucked off by an old man.” His eyes shrug. That is all there is to it, they are saying.

Cry me a river. Tears course down my cheeks. Great sobs rage from my body. The arrogance of the beauty of youth. I stagger forward. I take him by surprise. I roll him so that he is now face down on the bed. He struggles, but even in my drunken stupor I am too strong for him. I dig my knee into his shoulders. He wriggles his hips and waist and flails his legs, but he is going nowhere. Not until I say so.

I tug at the waist of his khaki shorts. He resists but I inch them down over the mounds of his buttocks. His cheeks are bare. I see bruises from the paddling are still to heal completely. I wish I had a paddle. I don’t, so I smack the palm of my hand across his buttocks.

“Gerroff! Leave me alone!” he yells as I pound away at his backside. The flesh feels soft and warm. Soon my palm begins to tingle. It is probably hurting more than John’s rear end. I don’t care. I hate him so much. If I had a knife I would probably plunge it into his heart.

My cock is rock hard. My heart races. My temples throb. I loosen my trousers and find my dick. I climb on his back. John squeals with terror.

“Headmaster, headmaster!” Mr. Albertson, the dorm master, stands in the doorway, ashen-faced. I climb from the bed and without fastening my trousers, I push past him and stagger down the corridor, leaving John convulsing on the bed.

Picture credit: Endart

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Charles Hamilton the Second

Squirt: A spanking love story

It was probably the most inappropriate relationship in the history of sex. I was thirty when we first met, he was eighteen. I lusted after him: always. He loved me.

We first met at the Svengali Club. He hit on me and I wasn’t about to pass up the chance of some Spring Chicken. Squirt was the sexiest piece of ass in the club that night. Virgin, and mine for the taking.

I don’t believe in love, but I do believe in sex and I get it whenever I can: which is always. I have a successful career in television production and I rake in a lot of cash, which buys me a loft apartment, fast cars, clothes, all the drugs I want. And sex. I don’t want for anything and I get what I want.

I tour a lot of the clubs and I know everybody on the scene and I’d never seen Squirt before that night. He was a newbie, hot, horny, eighteen and desperate to get laid. I was happy to initiate him into the world of adult sex.

I wasn’t the only guy with an eye on Squirt, and who can blame any of us: he was blond, cute as a button; he had a beautiful twink’s smile and an ass to die for. And, most of all, he was a Virgin.

He only had eyes for me that night and was mine for the taking. My friends told me to steer clear. He was jail-bait, they said, and they were right. He was still at school for chrisake.

He willingly came back to my apartment. He was nervous, I could tell. Who wasn’t their first time? But, he pretended he knew his way around. That just made him sweeter.

I had my way with him and it was the sweetest sex I had had in years. When we had finished it was late, he had no car, so he had to stay the night. If I had thrown him out in the middle of the night, none of this would have happened and my life would have carried on unhindered by Squirt.

In the morning I knew he had to get to school and I wanted to get rid of him quickly and never see him again, so we showered together. But Squirt wanted to arrange a date: for that night.

“What about your homework?”

“What if I don’t do it?”

“Then, you’ll have to be spanked.”

He flashed me his cutest, sexiest, smile.

“Oh Yeah, who by?” Giggle!

Horny as hell, I grabbed him by the arm and dragged him out of the shower. We were both laughing as, soaking wet, I sat on the bed and hauled him over my lap. Then, I spanked his naked little butt. It wasn’t hard, it was a game.

“I was joking! I was joking!” he giggled.

His smiles and his laughter turned me on and I popped wood. I flipped him over on to this back and saw he did too.

He was late for school that morning.

That night about nine-thirty I arrived home after work and a few beers and there was Squirt, standing across the street from my apartment. He was still in his school uniform: had he been waiting all night? He ran across the street calling my name as soon as he saw my Jeep turn the corner.

This was getting embarrassing.

“Art! Art!”

I stopped the car and wound down the window. “Go away. It’s over. It was just a fuck.” I steered into the underground parking lot and took the elevator to my apartment.

Squirt wasn’t easily put off. He put his finger on the entry phone button and wouldn’t move it until I answered.

“What do you want?”

“You!” It was his giggle that got to me. I buzzed him in.

In truth, I had been thinking about him during the day. I usually don’t think about past conquests, I’m too busy looking for the next. I had quite a scorching time in the bathroom of the bar an hour ago with a dark, sexy stranger. Don’t ask me his name. No, I’m not being discreet, I just don’t know.

Squirt entered my apartment.

“Do you want a soda? Some candy?” I was trying to be sarcastic, but my pupils dilated at the sight of him close up in his school uniform. He was sex on a stick.

Squirt saw he had me hooked. He might only be eighteen, but already he was beginning to understand that his blond hair, that goofy smile and, oh, that ass, would take him a long way.

“I’ll have bourbon, thanks.”

“You’ll have a damned good spanking for your cheek.”

Squirt’s eyes shined and a grin split his face.

“I’d like to see you try.”

I rushed across the apartment and, squealing, he fled. I chased him over the bed, around the dining table, through the space that is my office. Shrieking with delight he hurdled the bed once more.

“Can’t catch me; can’t catch me,” he squawked like a seven-year-old.

But, I could and I did. I cornered him against the wall in the kitchen area. He slid down onto his haunches, making him just the right height for me to take hold of his left ear lobe and guide him, not too gently, back into the living area.

“Ouch! Ouch! Oooh! Aaah! Leggo! Leggo!” he feigned pain, but still maintained that incessant giggling.

Still holding him by the ear, I maneuvered myself onto a chair, spread my legs wide and heaved him across my lap. He wriggled, genuinely wanting to be free, but I held him firmly with my arm across his middle. He was a marvellous sight. His ass, in his tight gray school slacks, was superb. Squirt must be one of the few guys in the world whose butt looks as sexy in pants as it does naked.

I brought the palm of my hand down across the seat of his pants. Unlike this morning, this was no game. I spanked him like I meant it. Smack-smack! smack-smack-smack! He gasped a little under the weight of my hand, but I kept on spanking. Looking back, I think maybe I did mean it. Squirt was incorrigible; he wouldn’t leave me alone. I had told him to go home, it was all over; a one-night stand. But, he had persisted, he embarrassed me in the street and he was cheeky to me in my home. Yes, the naughty little boy deserved to have his bottom smacked. He should be thankful I’m not one of those guys who keep paddles and other toys in the bedroom or his butt would be well and truly blistered.

Once I had demonstrated to my satisfaction that I was his master, I let him up. His face was bright red, but I hadn’t spanked him so hard and I doubt his ass was the same colour.

“Go home. It’s over.”

He was breathing heavily and he danced up and down as he rubbed the seat of his pants in an exaggerated fashion, as if his buttocks were on fire. God, he was cute.

“You’re not hurt at all. Come here.” I grabbed at his belt and in no time I had his slacks and shorts down to his knees. There was some coloring on his cheeks, but not enough to warrant the little dance.

His dick was rigid and, never one to waste an opportunity, I took it in my mouth.

I was busy at work for the next few days and away from my apartment a lot. When things calmed down I went home and banged some guy, Alfie. I met him at a club, bought him some drugs, and we went back to my place. We’d been at it for hours (that’s what drugs can do for you) and were spent, when the entry phone starts buzzing. It’s three in the morning, so I ignore it. But, I know the buzzer isn’t going to stop until I answer. It is Squirt.

I get up and tell him to stop stalking me and go away. We start an argument.

“Who is it?” Alfie is awake and comes over to see what the trouble is.

I explain it’s some “newbie” I fucked and now he won’t leave me alone. Alfie looks at the entry phone screen. There is Squirt, cute as always, his pleading eyes staring into the camera. I knew he had been practising for hours. He’s wearing cargo pants and a very tight top that shows off his youth to perfection.

“If you don’t want him, I’ll fuck him,” says Alfie.

The drugs must still be in my system: I buzz Squirt in.

He looks cute, but sorrowful. He is dressed in a top that he grew out of a year ago, he thinks it makes him look hot, but it just shows his vulnerability. He looks like a rent boy. I feel my dick stiffen.

Alfie is drinking bottles of water; he throws one to me. We both have raging thirsts. My head is sore, I need sleep, not confrontation.

“Where have you been? Do you know what time it is? Why aren’t you at home?” Oh God, I sound like his mother. He tells me he’s been looking for me for days. I say I’ve been working. It’s what grown-ups do to make the rent. I tell him to go home, his mother will be worried.

Alfie thinks he has the chance of another fuck and comes on to Squirt. I have hurt Squirt’s feelings and he wants to get back at me, so he flashes Alfie the cute grin.

“I’m going back to bed. You two do what you want.”

In the dark I can hear voices and then heavy breathing, then groaning, then a scream. It sounds like someone is being killed. It is Alfie coming in Squint’s ass.

The next morning Alfie has gone, but Squirt has not. Will he ever leave me alone?

I saw Squirt’s photograph in the newspaper yesterday. There’s trouble at the up-scale private school he attends. The kids want to form a gay discussion club, but the school authorities won’t allow it. Oh yeah: “discussion club,” everyone knows it’s just an excuse for a lot of horny gay guys to meet up and fuck. The school is part-funded by the state, so a local councillor has gotten involved. The picture was of a demonstration outside the school. Squirt is there with some dreary lesbians and gay students. One guy, Chris, is really hot. Why don’t the two of them just find a room and screw each other’s brains out, what do they need to discuss?

I had a horny dream last night. I am the school principal and I am in my office brandishing a paddle. Squirt and Chris are bent over, pants down, butts bared, and grabbing ankles. I give them ten swats apiece and then take each of them up the ass.

The cops called. They had arrested Squirt. Did I know him? Jesus; he’s getting me involved with the cops. I was about to deny all knowledge of the little brat when they told me he had been found with one of my credit cards in his possession.

I checked. He had spent $400 of my money at some fancy designer clothes shop. And – wait for it – another two hundred bucks for a room at an up-scale hotel. Who the hell had he been fucking at a hotel on my credit card?

God knows why, but I told the cops he had my permission.

I was mad as hell. Squirt must have stolen the credit card when he was here at my apartment. It’s not the money: I can afford that (and more). It’s just that he told me that he loved me.

When he came to visit I told him straight: you will pay all the money back even if it takes you years.

He smirked. Yes, smirked: as if to say, “Yeah, whatever.” It was a sexy smirk. The brat. Why does this always happen. He knows he can turn on his sexy grin and I can’t resist.

Well this time I did. Kind of. I didn’t plan it, I just said, “You’ll pay me back all the money and right now you will pay with your ass.”

His eyes shone. He was almost begging, “Yes, please.”

But he’d not gotten the message. He thought I meant I was going to fuck him.

Not so. Well, maybe not yet. I meant I was going to spank his bare ass until his creamy-white fanny was fifty shades of pink.

When he realized what I had in store for him, he tried to run. I chased him round the apartment. I work out at the gym (a lot) and I soon overpowered him.

My heavy clothes brush soon had him yelping. When he’d stopped yelping; he went on to yelling. By the time every bit of his pert ass cheeks and thighs were the color of a light burgundy, he was screaming.

I threw him face down on the bed. He lay there panting. My dick was like a stallion’s. I wrapped on a condom and took him like he’d never been taken in his life.

When we were both spent, I told him that I loved him. But, I didn’t mean it.


More stories you might like

Caught in their underpants

My first spanking — aged 18!

High school reunion


More stories from Charles Hamilton II are on the MMSA website


Charles Hamilton the Second