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  1. The Headmaster's Daughters - Part 1
  2. The Headmaster's Daughters - Part 2
  3. The Headmaster's Daughters - Part 3

The Headmaster's Daughters - Part 1

Categories Fiction, Masturbation, School, Teen

Author: Dogbyte

Published: 09 January 2019

  • Font:

Part 1 – Silly games

I was 16 when our school headmaster moved in next door. It was the first week of the summer holidays and of course it was raining. I’d been down the street at my friend Tom’s most of the day and we’d been playing on his Xbox. As I walked back up the road I noticed that the ‘SOLD’ board, which had been in the front garden of the next house for a couple of months since the previous owners left, had gone.

As I turned into our driveway I saw the car parked on the adjacent one and my heart sank.

“You’ll never guess who’s moved in next door,” My mum said as I walked into the kitchen.

“Mr Kennedy,” I said. “I recognised the car.”

“Oh,” her face fell, I’d spoiled her big surprise. She recovered fast though, “You didn’t say he had twin daughters.”

I shrugged, “I didn’t know.”

“About your age too I should think.”

This was news but I figured you wouldn’t want to send your own kids to a school you were in charge of. I went up to my room and phoned Tom.

“You can’t get enough of me can you?” he said. “You’ve only just left.”

“Creepy Kennedy has only gone and moved in next door to us!” I blurted out my news.

“Fuck, that’s bad luck.”

“My mum says he’s got twin teenage daughters though.”

“Interesting. I wouldn’t get your hopes up though, Kennedy’s an ugly sod, they’re probably fat like him and with a face like the back end of a bus.”

“Two buses,” I joked.

I didn’t see anything of the Kennedy’s for the next few days. They were obviously busy moving in and unpacking and stuff and I was either round at Tom’s or out and about with other friends. The Tuesday of the following week though Tom had called round. It was a sunny day, too hot to play video games indoors so we’d pulled a couple of old lounger chairs out of the shed and were sitting in the back garden with our shirts off soaking up the sun and listening to music on our phones.

I was about to go into the house and get a drink and pulled out my earphones to ask Tom if he wanted one too. In doing so I heard female voices from nearby. I nudged Tom.

“Sounds like the fat Kennedy twins are at home,” I whispered.

He grinned. “Let’s take a look.”

“Tom, no!” I hissed, but it was too late.

He made a stooping run across the lawn and crouched by the fence. Between our garden and the Kennedy’s this was only about five feet high so it was easy to look over the top. Tom eased himself up, looked for a second then dropped back down and beckoned me urgently.

I shook my head but he beckoned harder and mouthed, “Get here!”

Curiosity got the better of me and I copied his commando run across the grass and crouched beside him. He put his lips close to my ear and whispered, “Well, they’re not fat.”

Slowly we both straightened up so we could peer over the fence. Two slim, tanned teenage girls in bikinis had beach towels spread on the lawn and were lying face down in the sun. Both had undone their tops to get an even tan on their backs.

I heard Tom sigh and out of the corner of my eye saw his hand start to rub the front of his shorts. I jabbed him with my elbow.

“Ow!” He said out loud.

The nearest girl turned her head with a squeak of surprise. “Why you...” She started to rise but then remembered she was topless. “Look away!”

Tom and I turned. Caught in the act. I’d seen enough to know the back of the bus comparison was false too. It was lust at first sight.

“You can look now.”

We turned, both of us blushing hard. Both girls had put on robes and were standing facing us with their arms folded defensively across their chests. “You little perverts, If our dad was here you’d be in real trouble.”

We both looked down at our feet. The girl continued, “We know you go to his school, what are your names.”

I lived next door, there didn’t seem any point lying. “Paul,” I muttered.


“A real life peeping Tom,” said the other twin.

“We weren’t peeping, honest,” I said.

Tom backed me up, “We just heard your voices and thought we should say hello.”

The first girl raised an eyebrow. “That’s not what it looked like.”

“Maybe we will tell our dad what pervy creeps he has at his school.”

“N… no,” I stammered. “Please don’t do that.”

“We’ll do anything,” added Tom.

The twins leaned close to each other and held a whispered conversation, punctuated with giggles and a couple of sly glances at me and Tom. “All right come round tonight for your punishment, but wait till you see Dad’s car’s gone.”

We slunk back to our garden chairs but we couldn’t relax. “What do you think they’ll do to us?” asked Tom.

“They’ve just moved in, probably want some boxes moved or something,” I said but I wasn’t convincing either of us.

That evening Tom and I sat in my bedroom and waited until we heard doors slam and saw Mr and Mrs Kennedy drive off in their car. I was scared stiff, I’d hardly been able to eat my dinner and Mum asked if I was feeling ill from having spent too long in the sun.

“You ready?”

Tom nodded.

“OK, let’s do this.”

We went downstairs, I stuck my head round the lounge door and told my parents we were off out and wouldn’t be late. Moments later we were on the Kennedy’s doorstep and Tom was pressing the bell.

One of the girls opened the door. She was dressed in jeans and a dark T-shirt, the points of her nipples clearly visible through the fabric. “Come in,” she said and directed us into the lounge. “I’m Leanne, this is my sister, Leona. You’re Pervy Paul and you’re Peeping Tom.” She pointed to us each in turn and we shuffled our feet in embarrassment.

The lounge had a leather three-piece suite arranged around a glass-topped coffee table, a TV occupied one corner. Along the back wall a stack of remover’s boxes stood waiting to be unpacked. Maybe I’d been right, they just wanted our help with moving stuff.

We stood nervously surveying each other. I tried to keep my eyes away from Leanne’s nipples. Although they were twins the Kennedy girls weren’t quite identical. Leanne’s hair was cut a little shorter and Leona had a small birthmark on her neck.

“I expect you’re wondering what your punishment is,” Leona said.

Tom and I nodded dumbly.

Leanne picked up a pair of Wii controllers from the coffee table and handed one to each of us.

“Wii?” I frowned.

“Wii tennis to be exact,” said Leona.

Tom frowned too. “How is that a punishment?”

Leona smiled and said, “You don’t know the rules yet.”

I exchanged a sideways glance with Tom.

“Strip Wii tennis,” said Leanne with a triumphant grin.

“S… Strip?” stuttered Tom.

“Yep, it’s quite simple, every point you lose you take something off. We reckon if you play best of three at least one of you should end up naked.”

Tom and I had played Wii tennis a lot when we were younger. We were pretty evenly matched. I reckoned they were right.

Leona picked up a remote and turned on the TV. The game was already loaded and they had set up avatars for me and Tom. Everything was well prepared. Both twins settled on the sofa. “OK, boys,” said Leona. “Let’s see what you’ve got,” they both giggled.

I slipped the safety strap of the controller over my wrist and looked at Tom. “Let’s get it over with.”

I served first but Tom took the first point and I eased off a shoe. He took the second point too, but playing in my socks seemed to give me a boost and I took the next four, 15-30, 30-all, 40-30 game, so Tom stood in his bare feet.

The second game started. Tom had a strong serve so I wasn’t surprised that after two points it was 30-love and I was barefoot too. I took the next point though, 30-15 and Tom slipped off the checked overshirt he’d been wearing on top of his T-shirt. Tom took it to 40-15, I was wearing a tracksuit and was quite glad to take off the jacket as I was starting to get hot. I scored the next point though, 40-30, Tom removed the belt from his jeans. Tom took the game on the final match point and I took off my wrist watch.

The third and deciding game. The twins leaned close to each other whispering. My serve again, I aced the first point. Tom blushed as he pulled off his T-shirt and the girls tittered. I won the next point too, 30-love. Tom undid his jeans slowly, allowed them to fall to his ankles and kicked them off. The twins whispered to each other more urgently. I glanced across at Tom and could see from the front of his underpants that he was getting aroused. I swallowed hard, one more point and he’d be nude, two and my dignity would be safe.

It wasn’t to be. Playing in just his boxers galvanized Tom, he took the next point, 30-15 and my T-shirt joined the growing pile of my clothes on the carpet. He won the next as well, 30-all, I inhaled deeply and eased off my trackie bottoms. Now we were even. I glanced at the Tom, the bulge in his pants had grown larger.

The next point was hard fought with a long rally, I could feel sweat trickling over my ribs, but I won. 40-30.

“Show us what you’ve got, big boy,” Leanne giggled.

Tom didn’t hesitate, he pulled down his boxers, allowing his erection to spring free. The twins whispered to each other and kept glancing at Tom.

I shut my eyes, “One more point, one more point,” I repeated in my head. I lost, deuce.

“Off, off, off,” chanted the twins.

I pulled down my underpants. My cock dangled.

“Well that’s disappointing,” said Leona and I blushed. Tom seemed to be enjoying himself now, he moved his hips so that his hard penis swung from side to side like the jib of a crane. The girls whispered and giggled again.

I served, freed from clothes and nerves I took the point easily. Advantage Paul. I also noticed that, with the twins’ eyes on me and with Tom bouncing around beside me, my cock was responding too. I took the point and won the game with a whoop and a full erection.

I slipped the controller off my wrist and reached down to pick up my boxers.

“Not so fast, Tiger,” said Leanne. “Don’t opponents shake after a game?”

I reached out for Tom’s hand.

“Ah, ah, ah, our rules,” said Leona. “You have to shake each other’s cocks.”

I looked at Tom, he shrugged. I took his penis in my hand it felt hot and smooth. He took mine, his fingers were sweaty. We gave each other a perfunctory shake and let go.

“You can do better than that,” said Leona. “We want to see a proper shake.”

“You mean you want us to...” I stood open-mouthed.

“Yep,” A wicked grin spread across Leanne’s face. “Wank each other off.”

“And face this way please,” added Leona. “We want a good view.”

I stood next to Tom and we gave each other a sideways glance. He shrugged again and took my cock in his left hand. I took his in my right. We started to run our fingers along each other’s shafts. I’d never been wanked by anyone else before and it felt good. I came quite quickly and my semen splashed out onto the glass table top.

I closed my eyes and sighed. “Don’t stop,” muttered Tom, with an edge to his voice. I realised my hand wasn’t moving on his cock and I started up again, faster. Soon his spunk was shooting across onto the coffee table too.

The girls stood up and applauded. Tom leaned close to me and whispered, “That felt good.”

“Now...” Leona said. The twins evidently hadn’t finished with us yet. But at that moment headlights swept across the curtains as a car turned into the drive.

“Shit, they’re back early. Quick, Leanne, get a cloth and clean that table. You two grab your stuff.”

We bundled up our clothes from the floor and Leona pushed us through the kitchen and, still naked, out through the back door. “Wait here until I tell you the coast is clear. And don’t think we’re finished with you yet.”

Tom and I exchanged glances and struggled into our clothes in the gathering dark. We stood shivering on the patio, even though it wasn’t cold. After a few minutes there was a tap on the window and Leona gestured a hand towards the gate. We crept out of the garden and down the drive.

I glanced at my watch. “Come round to mine,” said Tom. “I’ve got some beer stashed and I could use one.”

We were silent on the short walk to Tom’s. His parents were out but his older sister, Jenny was in, sitting in the lounge watching a reality TV show. “What have you two been up to?” she said as we entered.

“What makes you think we’ve been up to anything?” said Tom, defensively.

Jenny pointed to his chest. “Well, for a start your T-shirt is on inside out and back to front, I can see the label.”

Tom blushed, “It was just a silly game.”

“Maybe I can join in sometime,” Jenny smirked. She was always teasing us and I think she knew I found her disturbingly attractive.

“Come on, Paul,” Tom pushed me towards his room.

“No silly games, boys,” Jenny called after us.

With the door closed behind us Tom felt under the bed and produced a couple of cans of beer. It was warm but we gulped it down anyway.

“That,” said Tom. “Was weirdly enjoyable. I’ll never be able to look old Kennedy in the eye again though. And by the way you give a great hand job.”

“I’ve practised a lot on my own. Anyway you’re not so bad at it yourself,” I said. But Leona’s final words, ‘...don’t think we’re finished with you yet,’ nagged at the back of my mind.

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Last Stories author Dogbyte

The Headmaster's Daughters - Part 3

Categories Fiction, Consensual Sex, First Time, Oral Sex

Part 3 – Party time The following week the Kennedys went away on holiday. With out the twins to use and abuse usTom and I slipped back into our old routine of hanging out with mates or playing video games at each other’s houses, but the taste of the delights next door lingered. One...


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The Headmaster's Daughters - Part 2

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Part 1 ended here: ...Leona’s final words, ‘...don’t think we’re finished with you yet,’ nagged at the back of my mind. __________________________________________________________________________ Part 2 – The garden We didn’t have long to wait to find...


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