The Head Boy and The Girl. A More Enjoyable Punishment Story

The Girl is in trouble again. This time the Head Boy has her alone and he will decide her fate.

One of the benefits of being the Head Boy of a public school was the undisputed right to roam anywhere within the College grounds, without fear of challenge.
Bainbridge enjoyed this freedom and was particularly fond of roaming the playing fields on Friday afternoon, which just happened to be when the senior girls had their weekly Games lesson! All the most attractive students would be there, performing energetically in clothing that revealed far more bare flesh than their usual 1950’s attire.

He was trying to affect an air of nonchalance as he ambled across the grounds, towards Miss Carter’s Games class, when he was distracted by the unmistakable smell of cigarette smoke.

Further investigation led him into a wooded copse where he spied a female student. She had her back to him and was anxiously trying to put out her fag.
Bainbridge wasn’t very interested in her cigarette. He was more interested in her long, shapely legs – naked from her ankles to the very top of her thighs, where they met the tight blue gym shorts that hugged her firm, round backside.
It was backside he had met before and he announced his arrival with a hearty “smack”.

“Oy, what the hell..!
Oh it’s you.”
The Girl greeted the Head Boy with a kiss.
It was The Girl he had helped the Headmaster to punish, so severely, just a few days ago.
The Girl had a name.
Her name was Jemima and Jemima was Bainbridge’s girlfriend.

“Sorry. I couldn’t resist. You’re not still sore, are you?” he asked.

“Do you mean inside or out?”

“Either.”

“Well, inside’s not too bad now, even though you did ram your cock right up there. But my thighs are still sore from the cane. Seven bloody strokes. The bastard!
And where did you learn to stick your cock up a girl’s arse anyway? Do Head Boys get special training or something?”

He didn’t want to admit that a cock up the arse was the standard initiation for all the first year boys and he had been no exception. He decided to blame the Headmaster instead.

“It was the Prof’s idea. I had no choice. Sorry!”

“Well you can tell him that it bloody well hurts!” she told him. “I’m surprised he didn’t do it himself, the dirty bugger.”

“I suppose he was worried about getting into trouble with your parents. I mean, they’ll understand if he decides to cane their daughter, but they might have something to say if he decides to fuck her up the arse!”

“I suppose so. He probably uses that Sally, from the kitchens for that,” she sniggered.

“What makes you say that?”

“Oh, all the girls know he’s shagging her. Why else would she always have so many sweets? She’s got more chocolates than Cadbury’s!”

“Well, you never know. She might like it “up the bum”!
I’m told some girls do, but you have to use a load of lubrication so it slides in more easily.
I was thinking of getting some butter from the kitchen so we can try it out.”

“You can forget that!
I don’t mind you having my mouth or my cunt, but my arse is my own!”

“Okay” he laughed.
“Can I ask you something though? Why were you sucking those boys off in the bogs. It’s not like you need the money or anything?”

“Well I do need the money. For fags!
Daddy gives me a big enough allowance but, he doesn’t trust me to spend it safely. I have to account for every penny and he wouldn’t let me get away with spending it on cigarettes.
So I need another form of income. Some money that Daddy doesn’t know about.
A few minutes on my knees once or twice a term is more than enough to keep me in smokes and I always get away with it.
I only got caught this time because Baldwin squealed like a pig when I made him cum. That’s the trouble with virgins!”

“I see. Just bad luck then?”

“It was. Anyway, why weren’t you there ready to spend a shilling on my services?”

“I didn’t know anything about it. I guess they didn’t want the Head Boy to find out, in case I split on them.
Anyway, I’m your boyfriend. I didn’t think I had to pay.”

“Of course not.” Her hands went to his trousers to get them off.

“Hey. No. Not here. It’s too muddy. Come with me. I have a better idea.”
He grabbed her by the arm and dragged her onto the playing fields.

“No. Stop. Where are you taking me?” She struggled.

“I taking you to see Miss Carter. She’ll be wondering where you are!”

“Oh no. Please I’ll be in so much trouble. She let me off with 1000 lines last time, so she’s bound to whack me if she finds out I’ve been skiving again.”

There was no turning back.
The girls in Miss Carter’s class had already spotted the dishy Head Boy, that they met every night in their fantasies. They had abandoned their exercises to see why he was gracing them with his divine presence.

“Please excuse my interruption, Miss Carter. I came across one of your students hiding amongst the trees.”

“Oh so that’s where you got to Chelworth! (The Girl had a surname too). It’s not the first time you’ve done a disappearing act to get out of my lesson is it? I can see I am going to have to deal with you.” She set off towards Jemima intent on doing just that.

“Erm, if I may, Miss Carter,” the Head Boy interrupted, “I can see that you are very busy and I would hate to keep the rest of the class from their calesthenics.
When don’t I deal with Chelworth on your behalf?”

“That’s very thoughtful of you, thank you, Bainbridge. Are you sure I wouldn’t be keeping you from more important matters.”

“Nothing that can’t wait, Miss, I assure you. I’ll be happy to help.”

“Okay, well the equipment store is open. I suggest you use that. I’m not sure whether you’ll find a cane in there, but there are sure to be some old training shoes and a few tightly strung tennis racquets that you might wish to use. I’ll leave it up to your discretion.”

“Very good Miss.”
——–

Bainbridge marched his girlfriend sternly towards the storage shed, as she made a show of “struggling” to get away.
He pushed her inside “angrily” and slammed the door, wedging it closed with a heavy lawnmower.

They looked at each other in silence for a moment and then both burst out laughing.
They couldn’t contain themselves after deceiving the Games teacher.
And they couldn’t contain their urge to get eachother’s clothes off!

Bainbridge pushed Jemima back against the wall, pinning her there and kissing her hard on the lips.
She pulled off his tie began to unbutton his shirt.
He followed her lead, pulling her tee shirt off, over her head and pushing her bra up to release her breasts.
He loved them.
She was a well fed young lady and they all that he could wish for, large, firm, pert, with sharp pink nipples, but best of all – they were naked!
He devoured them with his hands and mouth, sucking hard and biting lightly.

She arched her back to feed them to him, delighting in his attentions and took her hands to his trousers, seeking her own prize.
She knew exactly what to do. It wasn’t the first time she had undressed a boy. She quickly dispensed with his belt, trousers and pants and claimed his cock as her own.

He loved the way she held it.

“Fuck me. Fuck my cunt.” She demanded.

He opened her shorts and pushed them part way down her buttocks, but he was reluctant to leave her tits. “Get ’em off,” he ordered, making her do the work.

She obliged promptly, stepping out of them and pulling on his dick, urging him to enter her.

“Put it in.” He was still making her work for it.

She straightened her legs and raised herself up onto her tiptoes, attempting to match the height of his cock with that of her pussy.
He was too tall, so she gave up and steered his cock down between her thighs and up, up into the mouth of her slit.

The Head Boy felt marvellous moisture of her female opening longing to be penetrated. It was time to take control. He drove into her. Pushing her up against wall with the power of his hips and the cock drilling deep inside her. He slipped his hands under her arse. Squeezing a d lifting her clear of the ground.

He fucked her against the wall, impaled on his dick and clawing at his back, as waves of sexual pleasure flowed through her young body.
The same pleasures flowed through Bainbridge too and they erupted into waves of hot spunk that splashed and shot inside her.

It was their greatest shag of their lives. And they soon performed an encore; naked, missionary style on the shed floor.

They would have loved to spend the whole day screwing eachother, but they knew the Games lesson would end soon and Miss Carter would discover their secret love nest.

Bainbridge dressed quickly and Jemima began to pull her clothes on too.
“Stop.” he told her. “Don’t put your knickers or shorts on yet.”

“Why not? Carter’s going to be here soon.”

“Yes and she thinks I’m giving you a whacking. Your classmates will want to see how red your bum is when you get back to the changing room.”

“So… Are you saying l’ll have to let you spank me?”

“Yeah, unless you want to explain to Miss Carter what we’ve been doing for the last half hour!”

“Oh, bloody hell.” she sighed in resignation, “I suppose you’d better get on with it then.
Not too hard though and stay off my thighs, they’re already sore.
Where do you want me?”

He pulled out a chair and made himself comfortable. “Sit astride me, as though you’re riding a horse, but with your back to me.”

“Ok. Like this?”

“That’s it. Now lean forward. Put your hands on floor like it’s a wheelbarrow race.
Good.
Feet either side of my hips.”

She shifted awkwardly. Uncomfortably.
“Come on then. Do it if you’re going too or are you just going to enjoy the view?”

“Ow!” The first smack hit her. Hard .”That bloody hurt! I thought you weren’t going to take it easy!”

“You deserved that one for your cheek!” He teased, although we view between her legs was wonderful!
He set to work, using both his hands to deliver rhythmic slaps to each cheek, building up a rosy hue without striking her too severely.

“How’s that?” he asked.

“Ok so far, thanks.
It feels like your having fun though.”

He couldn’t deny it. The erection pushing up into her belly was evidence enough.

He kept up the rhythm. Spanking her buns like bongos, but only using one hand now.
The other snaked down between her legs and strummed it’s own tune on her twat.

“She moaned her approval.”

“Is that good?”

“Don’t ask stupid questions,” she told him.

“Fair comment.”
He continued to tease her twat, pushing a finger up inside her.
The spanking stopped, unexpectedly as he abandoned her arse and reached behind him.

“You know I’ve got to beat you with more than just my hand don’t you?
I’ve got to leave you with some marks or Carter’s going to guess what we’ve been up to.”

“Ok. I was afraid you were going to sat that. Don’t use the cane, though. That really hurts.”

“Of course not. I can’t find one anyway. I have found a pair of pumps though, so I’ll just use one of those.”
He took the black canvas training shoe in his right hand and smacked it down firmly on her bare bum.

“Oooh,” she flinched away from the sting. As she did so shock drove her pussy down onto his probing fingers. “Oh!”

Bainbridge left his fingers inside she continued to ride them as he laid down the full “six of the best”

“That’ll do.” he announced. “You look like a well spanked girl now.”
He reached forward and grabbed hold of her tits to pull her back up onto her lap.

“Don’t think a spanking has ever felt so good,” she told him, with a kiss.

“You’d better put your shorts on. The games lesson will be over soon.”

“Just my shorts. What about my knicks?”

“I’m confiscating those.”

“What? You can’t just keep them!”

“As Head Boy, I have decided that they are not regulation gym knickers, as required by the college rules,” he stated, grandly. “I am therefore confiscating them. You may collect them from my room at 7pm this evening.”

She smiled. It was a clever ruse, but she had spotted a flaw in his plan. “I’m not allowed into the boys’ quarters, am I? I’ll get into awful trouble.”

“It’s okay. I’ll send a note to your House Mistress along with a pass. You won’t be in any trouble.”

“Oh very clever, I’m sure,” she said sarcastically, “and when I get to your room, I suppose you’ll just hand over my underwear without any questions…”

“Yes, so long as you ask me nicely, like a young lady should.”

“Will it help of I get down on my knees and beg?” was her saucy suggestion.

“I believe that is the traditional procedure. Should I expect you at 7?”

“On the dot sir!”

————-

It was time for Jemima to leave. Bainbridge gave her a farewell kiss, pulled the lawnmower from the door and sent her on her way, with a pat on the bum.

She met Miss Carter a little way down the track.

“I hope Bainbridge wasn’t too soft on you, Chelworth.”

“No Miss. He was very hard. Very hard indeed Miss. He gave me a very stiff pumping.”

“A pumping? What on earth do you mean by that?”

“Well he was going to give me a caning as you suggested Miss, but he couldn’t find one so he spanked me with a old black pump instead Miss.
Rubber sole, size 10, Miss.
Really hurt.”

She continued down the track, grinning at the memory of the other “stiff pumping”.
One that Miss Carter would never know about.

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