Detention

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Toby was caught at school in a compromising position.
2.8k words
4.28
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Part 1 of the 3 part series

Updated 06/08/2023
Created 06/22/2017
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Croony
Croony
758 Followers

Adam Jones had just finished screwing the school secretary over his desk.

Adam was the headmaster at a prestigious boys school in London. He was in his mid fifties, tall, slim and handsome in a boyish type of way.

Cheryl Smith was in her early forties, also tall and quite curvaceous. She was married with no children and had been fucking her boss for over a year.

As they dressed they made polite conversation. 'Did you hear about young Johnson?' she asked the headmaster. 'No, who is he and what's it about?' replied Adam.

'It's rumoured that he was forced to suck off one of the other senior boys after gym last Monday. The PE teacher made him do extra training for next weeks cross country tournament so he was alone in the shower room when some of the other lads came in from rugby practice. Apparently he sobbed the whole time but swallowed the boys cum and had a hard on all the while!'

'Is he worth looking at to maybe have some fun with? asked the headmaster.

'Oh, he's very cute. I should think so,' replied Cheryl as she was pulling her tight skirt on over her hold up stockings and thong.

'He's also on a bursary and if it is true he would have to leave the school,' she added.

'Do I know his parents?' the headmaster asked.

'Parent, he lives with his mother. A one parent family.'

'What's she like,' asked Adam a thought twirling through his mind.

Cheryl could see where this was going and painted a glowing picture of Ms. Johnston. 'Slim blonde in her mid thirties. I've met her at a couple of school meetings,' she said. 'She certainly gets the boys hot under the collar.

'Is she someone we could play with?' he asked. 'Oh I think so.' replied Cheryl. 'Ring her and ask her to come in to see me after school, say Thursday could you,' said the headmaster with a knowing smile.

Susie Johnson was waiting outside of the headmaster's study on Thursday when Mrs Smith beckoned her to enter.

Adam thought she was indeed a rather attractive young woman who had dressed in a short denim skirt and wearing a tight white t-shirt which accentuated her small round breasts. Her blonde hair was tied back in a pony tail and she looked a lot younger than she was.

'Thank you for coming Susie, is it alright if I call you Susie?' the headmaster asked as he walked towards her offering his hand. Ms Johnson just nodded and shook it. 'You're probably wondering why we've asked you here?' Adam put his other hand on Susie's shoulder and paused until Susie answered in the affirmative.

He then explained the situation to her, and kept his hand on her shoulder to comfort her.

'So as you can see we have no choice but to expel your son,' he stated.

'Oh no, please. You can't do that,' pleaded Susie Johnson.

'Unfortunately we have to, unless...,' he said.

'What? What can be done?' asked an anxious Susie.

'Well that's down to you!' the headmaster said as his hand slid off her shoulder and on to her right breast. It remained there until Ms Johnson grasped what he was doing.

'N..no, I..I can't,' she said as her hands went to remove his. She hadn't realised that Mrs Smith was standing right behind her until she felt her hands grabbed and pulled behind her.

'Unfortunately you have no choice, my dear,' said the headmaster in a devilish tone. Mrs Smith leaned closer and whispered, 'you might even enjoy it!'

'W..what are you going to do?' Susie asked nervously.

She had an idea when the headmaster pulled her t-shirt out of her skirt and Mrs Smith began to unbutton it from behind before it slid to the floor.

Adam began to caress her breasts while Mrs Smith with one hand still holding Susie's wrists expertly undid her bra allowing the headmaster access to Susie's naked tits.

'Oh God,' cried Susie as the headmaster lowered his head and took one of her large erect nipples in his mouth. Mrs Smith used her free hand to stroke the front of Susie's shiny white silk panties.

Susie moaned as the older couple kissed, sucked and stroked her body. When Mrs Smith kissed her neck and she slid two fingers into her pussy she lost it completely and came as the headmaster gently bit into her nipple.

'There, I told you that you would like it,' said Cheryl as she pushed Susie down to her knees by her shoulders. 'Now it's our turn,' she said as the headmaster unzipped his trousers. Susie gasped as she saw the headmaster's thick nine inch hard cock appear from beneath his boxer shorts.

He walked over to where Susie was kneeling and ordered her to suck it. In a trance she took it deep in her mouth. 'Get it hard so I can fuck you properly,' he said.

While Susie was sucking the headmaster's cock Cheryl was slipping off her thong. She slipped a finger over her shaven pussy and moaned at the thought of Susie's tongue licking her to orgasm.

She hopped up onto the headmaster's desk and as soon as he was ready he led Susie over and told her to bend over. Cheryl grabbed her hair and guided Susie's face between her open thighs. 'Lick!' was all she said. Susie began to lick and she could feel the headmaster rubbing his hard cock up and down her pussy lips.

She moaned into Cheryl's pussy as the headmaster slid his cock home.

Her groans were muffled by Cheryl's pussy as the headmaster pounded her hard from behind. Adam watched the young lady's bottom wobble as he fucked her and decided he had to have it. Cheryl sensed what Adam was going to do so she wrapped her stocking clad thighs around Susie's neck pinning her to her sopping wet pussy.

When Adam was sure his cock was well lubricated with Susie's juices he pulled out and quickly pushed it up against her arsehole. Susie guessed what was about to happen and shook her head trying to get free and shouted a muffled 'Nooooo' which nearly caused Cheryl to cum but when he slipped his cock deep into Susie's arse her scream sent Cheryl over the top and she came all over the younger woman's face.

Susie started moaning as the headmaster's cock slid in and out of her backside. Cheryl slid off the desk and knelt down beneath them. She began stroking Susie's pussy lips as Adam shagged her arse. 'Oh God.' moaned Susie. She groaned even harder when Cheryl slid two fingers into her pussy and exploded when the older woman sucked hard on her clitoris. This caused her hole to tighten and the headmaster to shoot his load deep into her bowels.

After they had straightened themselves up the headmaster explained that they were going to have to speak to Toby, her son, and get his side of the story. He also went on to say that her son may need to be punished.

As she was leaving the headmaster told Susie that they would need to see her again soon. What they didn't see was the smile on Susie's face as she closed the door and left.

The next day eighteen years old Toby Johnson was summoned to the headmaster's office by Cheryl. He was told to enter and saw them waiting for him.

'Ah Johnson, so good of you to come,' said the headmaster. 'I hope you don't mind Mrs Smith being here but I felt it wise.'

Adam went on to tell Toby what Cheryl had heard and asked for his views on the situation. Toby explained what had happened.

'Did you enjoy the experience?' asked the headmaster. Toby looked aghast and tried to answer. 'I..I..er..'

'I heard you had an erection while you swallowed the senior boy's jism,' the headmaster countered. Toby hung his head in shame.

'You're a naughty boy Johnson and you need to be punished.' The headmaster nodded at Cheryl who approached Toby and said, 'let's get you ready shall we?' as she started to undress the now nervous boy.

'W..what are you going to do to me?' he asked 'Oh you'll see,' replied Cheryl as she stripped him.

Soon Toby was naked and standing with his hands in front of his crotch.

'Put your hands on your head Toby,' asked Mrs Smith nicely. 'Do it!' barked the headmaster. Toby's hands flew up to his head giving the older couple a good view of his flaccid prick.

'Come here!' said the headmaster walking to the center of the room. Toby did as he was told and when he was told to kneel he did.

The headmaster took hold of his trouser zip and slowly lowered it in front of Toby. He took out his cock and slowly stroked it inches from Toby's face.

'You seem to like sucking cock and swallowing cum so let's see what you can do with this.'

Toby leaned forward with his hands still on his head and took the headmaster's stiff cock deep into his mouth and started to suck it.

'Oh, he's a natural, Mrs Smith,' the headmaster stated. 'Put your hands by your side,' Toby was told. The headmaster then took the boy's head in his hands and face fucked him hard. Toby could feel the older man's cock expand in his mouth and knew what he had to do. Soon the headmaster's cum was flowing down his throat as he fought to swallow it all.

Satisfied the headmaster pulled out and tucked himself back in his trousers.

'I think it's correct what they say Mrs Smith,' said the headmaster as he saw that Johnson was sporting an erection. 'Maybe you can do something with that?'

Toby was told to lay on his back on the carpet while Cheryl hoisted up her tight skirt and removed her soaked black thong. She straddled the prone boy, took his seven inch cock in her hand and guided it into her pussy as she sank down on it. He wasn't as big as the headmaster but it fit nicely as it had a bit of girth. It didn't take long for Toby to shoot off inside her but Mrs Smith kept riding him until she had at least two orgasms and Toby came again.

Toby was told to dress and expect another summons.

A week later Susie Johnson walked into the headmasters office. She was wearing a little black dress, stockings and high heels. Since she'd had the call from Mrs Smith to attend another meeting regarding her son she had been looking forward to seeing the headmaster and Cheryl again.

'Why, Ms Johnson, you look delightful,' commented the headmaster. Susie blushed and said thank you. Behind her, naked, tied to a chair and gagged was her son.

'Maybe you'd like to take your dress off so it doesn't get stained,' said the headmaster. 'Mrs Smith why don't you help Susie get ready for today's punishment?'

It was only when Susie turned towards Mrs Smith did she see the mature school secretary kneeling down and stroking her restrained son's hard cock.

'Oh, my God, what is he doing here?' screamed Susie.

'All part of your punishment my dear, do hurry and undress so we can start,' said the headmaster. Mrs Smith went up to Susie and started to unzip her dress. 'Oh please no. Not in front of Toby,' she pleaded. Mrs Smith continued to ease the dress from her shoulders until she was standing in her black half cup bra, tiny black silk panties and black stockings held up by a black satin suspender belt. In her high heels she looked like a porn star and Toby couldn't take his eyes off his mother.

Cheryl took hold of Susie's arms so she couldn't cover herself up and turned her to face her son. They heard the sound of the headmaster's zip being lowered as he walked towards Toby. With his half hard cock in one hand he pulled down the young boy's gag with the other. 'Show your mother what you are good at boy and suck me hard so I can fuck her.'

'Nooo,' moaned his mother as Cheryl plunged her hand into Susie's panties and found that her pussy was dripping wet. Cheryl continued to stroke her pussy as Susie watched her son fellate the headmaster. Cheryl pushed her to her knees and spread her own legs. She pulled her thong to one side and pulled Susie's face hard between her thighs. Toby watched as his mother licked Mrs Smith, the school secretary, to orgasm as he sucked on the headmaster's now hard cock. As soon as Cheryl let out a long groan of satisfaction the headmaster pulled his cock out of Toby's mouth and both he and Mrs Smith marched Susie over to the headmasters desk where they pushed her gently over it so she was lying on her back. Cheryl grabbed hold of her black silk panties and drew then down her thighs and off. She couldn't help but push her face into Susie's freshly shaved pussy and lick her clitoris until she was moaning with pleasure. 'I think she's ready for you now headmaster,' she said as she stood up and walked over to Toby.

The headmaster was as hard as he'd ever been after watching that and without a pause slid his cock deep into Susie who groaned and wrapped her stocking clad thighs around the headmasters back.

Mrs Smith slowly stroked Toby's cock as he watched the headmaster fuck his mother. She took the black silk panties and rubbed the crotch under his nose. 'Oh Toby, I think your cock just got harder. Do you like the smell of your mother's pussy?' she asked. Toby could only groan as Mrs Smith masturbated him. He watched as the headmaster fucked his mother hard and when she squealed as she had a huge orgasm Toby came all over Mrs Smith's hand.

By now the headmaster was pounding Susie through another orgasm when he felt his balls tighten and twenty seconds later he unleashed his cum deep into Susie whose pussy walls milked him dry.

Mrs Smith untied Toby releasing his gag and walked him over to where his mother was lying. 'You like cum so much why don't you clean your mother up?' she said pushing Toby's face into his mothers pussy.

Toby began to lick his mother as Mrs Smith held his face in place. He could taste the headmaster's cum as it seeped out of her pussy.

'Noooo,' groaned his mother as she realised what was happening. 'Oh God.' she exclaimed as another orgasm started to build.

'Aaarrgghh.' she cried as her orgasm hit and she clamped her legs tight around her son's head.

Cheryl pushed Toby down on the carpeted floor, his erection sticking up. 'Oh I think you liked that didn't you Toby?' asked Mrs Smith.

Susie looked down to see her son on his back on the floor with his hard cock bobbing up and down.

'Come on,' said the headmaster as he lifted Susie off his desk, 'We're not finished with you yet!'

Both he and Cheryl dragged her over to where Toby lay and forced her to straddle her son. 'Nooo, please. This isn't right. Oh my God,' she cried as she was forced down on to her son's cock. Automatically she began to move her hips.

'That's right, go on, fuck him.' ordered the headmaster as he held on to her.

Soon she was riding her own son without the headmasters help. 'Oh God, fuck me darling, fuck mummy. Oh no, I'm cuuuuummminngg!' she shouted as she picked up pace. 'M..M..Mum, I..I..' stammered Toby as he shot his spunk into his mother's pussy. Susie rode him to one more orgasm until she collapsed on top of her son, smothering him with kisses.

After they had dressed and left the headmasters office hand in hand Cheryl turned to the headmaster and said, 'look at what we may have started!'

'Yes.' said the headmaster. 'I'm sure they will be a lot closer in future. You know, watching that has made me quite horny.'

'Me too,' answered Cheryl as she slipped off her thong and the headmaster removed his trousers. 'Lie down. I want to ride you,' she said.

As she was fucking the him she said, 'I'm thinking of buying a strap on,' 'Dear god,' said the headmaster. 'What on earth for?'

'Well Toby has got such a cute little bottom I could really bugger him senseless with it,' she said.

Just then both of them came imagining it!

Croony
Croony
758 Followers
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  • COMMENTS
11 Comments
AnonymousAnonymousover 6 years ago

I stopped reading after the lame blackmail attempt and the not so implied male on male gay stuff. Pick a category and stick to it. If you wanted a forced non consent put it there. If you want the male head master and the male student to fuck put it the gay section. Jesus I cant stand when authors cant put thingsin the proper categories. Why so much hate? because most people dont really care for those subjects especially combined and most dont find it erotic or sexy.

AnonymousAnonymousalmost 7 years ago

sick

AnonymousAnonymousalmost 7 years ago
Need a part 2!

Gotta have little Toby take it up the ass from both the secretary and the headmaster. Maybe the secretary can pound his ass while he sucks off the headmaster and his mother sucks him off

sniffpantiessniffpantiesalmost 7 years ago
Nice

I loved it....no idea why so many negative comments...keep on writing!!

AnonymousAnonymousalmost 7 years ago
Is this writer projecting?

This was one of the worst stories I ever read. This was so ridiculous and non erotic. Who finds rape and faggots erotic? Maybe you were molested by your headmaster or something and this was your way to vent.

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Detention Series Info

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