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Squirt: a Spanking Love Story

by Charles Hamilton II

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 24 Feb 2018

It was probably the most inappropriate relationship in the history of sex. I was avoiding becoming thirty when we first met, he was just turned seventeen. 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, young 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 Christ sake.

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 more desireable.

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 had a boner. 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 seventeen, 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 colouring 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 cock 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 mom 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 am called to the office of my boss. He was some kind of English gentleman before he came here. His name is spelt Mr Magdalen, but he says it Maudling. He circles the room a few times. He’s a large man. Very traditional. He’s got one of those bushy moustaches like fighter pilots used to have in World War Two. He tells me I have been upsetting a client. I don’t argue. I know what he means. I don’t suffer fools gladly. That’s how it goes. I know I haven’t upset anyone really. The client makes millions off my back. But that’s not the point.

I know what is going to happen. Mr Magdalen stops his pacing and goes over to a table by the wall. He pulls open a drawer, reaches in an takes out a cane. It looks like the kind of thing Charlie Chaplin’s Tramp used to carry, but it’s a bit thinner and much more whippy. He flexes it between his hands and then he swishes it. My eyes watch it travel through the air.

He nods towards an armchair he has already placed near the centre of the room. I slip out of my jacket and let it fall on the top of his desk. He swishes some more. I stand behind the chair. The back is low and the greenish seat cushion has a dent in it where someone has just been sitting.

Mr Magdalen taps the tip of his cane gently against the apex of the chair. It is my signal. With steady hands I unbuckle my belt and pop a button. My zipper descends smoothly and my pants open. I wiggle my hips suggestively and my pants slip down my thighs. Mr Magdalen is standing behind me for a better view. I lift up the tail of my dress shirt so he gets a good look at my smooth skin and muscular stomach. Then I bend forward over the chair. I place my hands firmly on the seat cushion with my feet apart. My body is angled like a partly open hair grip.

He takes hold of the waist of the tighty-whities I am wearing especially for the occasion and pulls them so they ride up in my crack. I breathe normally. Waiting for the pain. I am not usually a sub. Around the clubs I am well-known as an aggressive top. I am reminded of my high school. Coach Needham used to like to have me bent across a stool in the locker room. We wore tight white cotton shorts. His paddle was so large it covered both cheeks. He gave five swats or ten, depending on how horny he felt. After, he always let me suck him off in the showers. Happy days.

No such luck with Mr Magdalen. He gets off some other way. I feel him sawing the cane across the centre of my buttocks; he is getting his aim. I shiver as the cane rises and my cheeks clench. Then: Swipe! I hear the crack of the whippy rattan cane connect with my ass, but it is fully a second or more before the pain crashes through my buttocks. It’s just like he’s pressed a white hot wire into my flesh. I gulp in air and hang on to the seat cushion for dear life. The cane taps a second time, rises and takes off the underside of my cheeks. I screw my eyes tight. The cane taps again ...

As I inspect the damage in the washroom mirror I wonder where I can get a cane. I would love to get Squirt in his black school blazer and pale gray slacks back at the apartment. Bend over boy! Touch your toes. It’s six-of-the-best for you young man. English style. What Ho! Don’t you know.


I don’t see Squirt for a couple weeks. Then he is at the Svengali. He is dancing with a guy his own age. They are naked except they are wearing the shortest and tightest leather shorts. They are creating a sensation. I down my drink and head off to the back room to fuck someone I don’t know and can’t see.


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 hormonal 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 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 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.


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