Detention Pt. 02

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The continuing adventures of Toby and his mother.
3.3k words
4.5
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Part 2 of the 3 part series

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

Susie Johnson had a sip of her chilled white wine as she got ready for a night out with a couple of her friends. She'd finished her make up and had chosen her sexiest black underwear with black hold up stockings. She had decided to wear her favourite little black dress. She remembered the last time she wore it. She would never forget the day when she was ravished by her son's headmaster and the school secretary. She was also forced to fuck her own son which thought sent a shiver down her spine and a tingle to her pussy.

They'd both agreed to forget it ever happened and to put it behind them. What they didn't know was that they both secretly masturbated at the thought of it late at night in bed.

Susie walked down stairs to find Toby lying on the sofa in his shorts watching the television. 'How do I look, darling,' she asked.

Toby was taken aback. The last time he'd seen her in that dress was when she'd walked into the headmaster's study and he'd been naked and tied to a chair while a fully clothed Mrs Smith, the school secretary, slowly stroked his cock.

'Y..you look great,' he said with a tinge of jealousy in his voice. He knew she would be out on the pull and more than likely end up with some bloke. He banished those thoughts quickly.

'Okay,' she said as she grabbed her purse. 'Don't wait up for me.' Toby heard the door slam and turned back to watch the television.

It was nearly midnight when Toby decided to go to bed.

Susie by then was in a club with her mates. She was getting annoyed at all the creeps that tried to feel her up on the dance floor. She was horny and looking for the right guy to go home with but she was getting more frustrated as the night went on.

Suddenly she had an idea and after shouting goodnight to her friends over the load music she jumped in a taxi and went home.

Sitting in the taxi she wondered if what she was about to do was a good idea but she was just on the right side of drunk and convinced herself it was.

Once in the house she tiptoed up to the bathroom and took off her dress. She used some mouthwash and combed her blonde hair, took a deep breath and headed to Toby's room.

Toby was sat up in bed reading when his mother walked in. 'M..Mum, what are you...' His voice broke off as he realised that his mother was wearing only her black silk bra, silk panties with black hold up stockings and high heels.

'Shush darling,' she said as she crawled up onto bed and took the magazine he'd been reading from him and threw it on the floor. She laid down beside him and stroked his hair. 'I missed my little boy,' she said. Toby could feel that his cock was very hard and it didn't go unnoticed by his mother.

'Oh, have you missed me?' she drunkenly giggled grasping his cock through the bed sheets. Toby just groaned. She slipped her hand under the sheets and down the front of his sleep shorts. 'Oh Toby,' she groaned.

She reached behind and undid her bra and threw it on the floor. Taking Toby's head she pulled him to her so he could suckle on her erect nipple. She went back to stroking his cock.

'M..Mum,' gasped Toby as he felt himself about to explode. His mother pulled him back to her breasts and wanked her son ever faster. Toby groaned onto her nipple as Susie felt him cum over her fingers. 'Good boy, now we'll have to get you out of those sticky shorts.'

She pulled back the bed covers and stripped him before pushing him back down and licking the remaining cum off her fingers and his cock. Susie spent a lot of time licking his cock which was beginning to resurrect. Taking his hardening cock she opened her mouth and began to gently suck him until he was at full mast again. Toby just laid back and enjoyed what she was doing to him. Susie took her son's cock out of her mouth and peeled down her panties where they joined her other underwear on the floor.

Susie then straddled her son and looked at him deep in his eyes. 'I really need this son. I'm sorry,' she said as she plunged down onto his hard prick until it was fully embedded in her dripping wet pussy. She slowly fucked him at first before speeding up and fucking him with careless abandon.

Soon Toby was fucking her back. She bent down to kiss him full on the mouth, her tongue seeking out his as Tony played with his mother's nipples.

Susie screamed in ecstasy as she came on her son's cock but kept fucking him hard. She could feel another orgasm building just as Toby began to pant and she could feel his cock expand inside of her pussy. 'Mummeee,' he groaned as his cock spewed out his cum coating his mothers walls which pushed her over the edge causing her to have an even stronger orgasm.

They laid there in silence until Susie said, 'Oh God Toby. I'm sorry I shouldn't have done that.' She started to sob gently and Toby put his arms around her and told her it was alright and that he wanted it as much as she had.

Susie kissed him gently on the lips and walked back to her own bedroom.

Headmaster Adam Jones was in a foul mood when he arrived at school on Monday morning. Cheryl Smith the school secretary hadn't been able to pay him a visit at his home on Sunday afternoon as planned as her husband hadn't been well and she couldn't leave him. Adam was frustrated and horny.

'Stay behind after school would you?' he barked at Mrs Smith who very politely agreed.

Once they were sure everyone had left the school Mrs Smith knocked on the door to the headmaster's study and walked in.

'You were a very naughty girl for not turning up yesterday.' he said. Before Mrs Smith could answer he dragged he over to his desk and pushed her face down over it causing her to scream in shock.

He slid her tight pencil skirt over her hips and marvelled at the sight of her buttocks framed by a black silk suspender belt holding up dark grey stockings. He took hold of her silky black panties and peeled them down her legs where he made her step out of them.

Mrs Atkinson felt him rubbing her bottom and was quite looking forward to getting a hand spanking from him when he brought down a leather strap he had in his other hand hard on her naked buttocks.

'Maybe you'll think better next time when you cancel our Sunday afternoons,' he said as he rained another slap down.

Mrs Smith was groaning in pain and pleasure as her pussy gushed with her juices.

'Next time you'll do as you are told,' panted the headmaster as the next two blows fell.

By the time she had suffered all six strokes she heard the headmaster fumbling with his belt and the sound of his zipper being lowered. As his trousers hit the floor he slid home his very hard cock into her very wet pussy and fucked her hard and fast until they both exploded together.

Once they had kissed and made up she told him that the strap-on cock she had ordered had arrived at the weekend and asked if they could try it out on Toby Johnson as they had discussed.

'When do you suggest?' he asked. 'How about Wednesday after school.' she replied.

'Sorry, can't do any night this week I'm at a series of headmaster conferences,' he stated. 'Doesn't stop you from having fun with him does it? You can tell me all about it when you come over on Sunday.'

Cheryl smiled at the thought.

After school on Wednesday Toby knocked on the door to the headmaster's study and was surprised to find only Mrs Smith there when he was shown in.

'Er..y..you wanted to see me, Miss?' he asked. 'Yes I do,' said Mrs Smith as she brushed past him and locked the door.

A nervous Toby waited to see what was going to happen. Mrs Smith walked up to him and started to undress him. 'Wha..what are you doing Miss?'

'Shush little boy, surely you know by now!' was all she said until he was totally naked. 'I want you to lie across the desk and hold on to the edge. Don't let go or you will be in big trouble.' she ordered.

Once Toby was in place she started to caress his bottom, seeking out his little hole. Toby shuddered as her fingers trailed down it.

She took a dollop of gel and using her middle finger slid it deep inside of him causing him to moan loudly. She did the same with two fingers and by the time she had three fingers inside him stretching his hole he was practically hyperventilating.

Mrs Smith then stepped back and pulled up her tight skirt. When the black eight inch strap-on she was wearing came into view Toby gasped. 'Don't even think of letting go of that desk,' she said menacingly.

She coated the fake cock with more gel and pushed it against the young boy's hole.

'No Miss, please Miss, not that,' he begged. With one push about an inch of cock slid into him. Slowly she kept up the pressure until the whole cock was buried to the hilt. Gently she started to fuck him, the end of the strap-on rubbing on her clitoris. Toby groaned as it slid in and out of him, rubbing hard on his prostate.

Mrs Smith quickened up her movement as she fucked the boy harder and harder. Toby was squealing as he was being fucked and Mrs Smith was moaning loudly.

With one hand she reached under him and was surprised to find his cock was hard and throbbing. The little slut likes being fucked in the arse she thought. This gave her an idea.

She peeled back his foreskin and used her gelled hand to stroke the crown of his cock making him groan as the fake cock pounded into him.

She was nearing her orgasm as she wanked him harder until she could feel his cock expand in her hand and she knew he was about to cum.

With one last hard push she impaled her cock deep into his arse as she shuddered to her orgasm and she heard him shriek then explode in her hand.

The following Sunday afternoon as she lay beside the headmaster after an hour of rigorous fucking and recounted to him what had happened the previous Wednesday with Toby she told him what her idea was. Adam just smiled and nodded.

On Friday Susie Johnson was surprised to receive a telephone call from the headmaster inviting her and her son to his house for afternoon tea on Sunday. She gracefully accepted and told him she looked forward to it. As she put the phone down she got a familiar tingle in her pussy as she guessed it wouldn't just be tea and cakes.

Susie Johnson anxiously rang the bell of a tall imposing townhouse, her hand gripped tight by Toby's. The door opened and the headmaster dressed casually in chinos and a polo shirt welcomed them inside. He thought Susie looked very nice in her yellow flowered summer dress with cream tights, cream handbag and shoes. Toby looked nervous in t-shirt and jeans.

When they were shown into the sitting room Susie was surprised to see Mrs Smith there and a man she had seen once before but wasn't familiar with.

'Susie, you already know Mrs Smith,' said the headmaster by way of introductions, 'and this is Peter Gaydon, our music master. I owe Peter a favour which is why I asked you to bring Toby.'

Toby groaned inwardly when he saw Mr Gaydon smiling at him. Everyone at the school had nicknamed him Gaydar Gaydon because of his predilection for boys. His mother looked a little confused but said nothing.

'Peter, why don't you take Toby up to one of the spare rooms while we chat to his mother?' said Adam.

As Toby was led away by the teacher Susie tried to stand and said, 'Wait..wha...' Mrs Smith held her back and told her not to worry as they would be going upstairs soon. She placed her hand on Susie's thigh and moved her hand under the sundress and found the tops of her stockings and her suspender clasp.

'Oh, I think Ms Johnson is expecting more than tea Headmaster by the underwear she has on!' Stated Cheryl Smith.

'Well then,' said Adam. 'Let's not disappoint her.' They took her by the hand and led her upstairs to the headmaster's bedroom.

In the spare room Toby was pleading with his music teacher not to undress him.

'Oh come on Toby. We both know what you like,' said Mr Gaydon.

'Bu..bu..but,' stammered Toby as his jeans were removed and placed next to his shirt on the bedside chair. Standing naked in just his trainers he tried to cover his penis which for a reason that baffled him was getting hard. Mr Gaydon removed his trainers and then took away Toby's hands so he could get a better look at the boy's cock. 'Mmmm, that looks nice,' he said.

He pushed Toby down onto the bed then joined him and started to slowly wank the boy. Toby could only moan but gasped as the teacher took his now hard cock into his mouth. Toby had never had a man suck his cock before but Mr Gaydon was doing such a good job he could only lay back with his eyes closed and enjoy the sensation.

Soon he could feel his loins stir and he knew he was about to cum.

'S..si..sir, I..I'm going to..' was all he could say before he unleashed the contents of his balls into his teachers mouth and straight down his throat. Mr Gaydon kept sucking until there was nothing left in the boy.

'That was yummy Tony, thank you,' he said. Toby lay back exhausted after his enormous orgasm and could see Mr Gaydon removing his clothes.

Climbing naked onto the bed he guided Toby's head down to his crotch.

'Your turn now,' was all he said as he guided the boy's mouth onto his straining cock. 'Mmmm, good boy.'

After a few minutes of being pleasured by Toby the teacher got him to lie down on his back. Taking a bottle of gel from the bedside table he squirted a dollop on his finger and rubbed it around the boy's hole before sliding it in deep. Toby groaned. He groaned louder when his teacher inserted two finger and was bucking his hips when he had three fingers inside him fucking his arse.

Mr Gaydon lubed up his cock, spread Toby's legs and knelt between them rubbing his cock around Toby's hole. Toby knew what was coming but he still moaned when the head of his teachers cock penetrated him. Mr Gaydon inched his hard cock slowly into Toby's arse until his balls were touching the boy's buttocks. He then slowly began to fuck him.

After a few minutes he pulled out and got Toby on his hands and knees before sliding his cock back into him. This time he fucked Toby hard and fast. He reached round and found the young boy's hard cock just as Cheryl had said. He wanked it as he fucked his hole, both of them moaning at the sensation. He could feel Toby's cock expand so he let go and grasped his hips to finish off inside him. Toby could tell that his teacher was going to cum inside him and the thought pushed him over the edge and he came without being touched just as Mr Gaydon filled his arse with his spunk.

In the Headmaster's bedroom Susie had been slowly undressed by Mrs Smith until she was standing in her cream suspender belt and cream stockings. She was forced on her back on the bed as Mrs Smith pushed her face between the young woman's thighs and began to lick her pussy as Adam undressed.

'Your turn.' said Mrs Smith when Adam was naked. He crawled onto the bed and started to kiss Susie whilst playing with her nipples and caressing her breasts. When he began to stroke her clitoris she began to moan and move her hips. She had her eyes closed as she was being pleasured and didn't see Mrs Smith strip to her black satin girdle and stockings or strap her black eight inch fake cock to her waist.

She climbed onto the bed as the headmaster stopped kissing and playing with her now wet pussy. 'I think she's ready for you now Mrs Smith,' said the headmaster. When Susie saw the strap-on cock she gasped.

'Be a good girl and get on your hands and knees will you?' She asked Susie, who obeyed.

Adam sat with his back to the headboard and guided Susie's mouth onto his throbbing cock just as Mrs Smith's rubber cock slipped easily in to her soaking pussy causing her to moan around the headmaster's.

The headmaster was holding Susie's head and fucking her face as Mrs Smith was pounding away at her pussy. Without any warning the headmaster gave out a grunt and filled her mouth with his cum which triggered her own orgasm. Mrs Smith pulled out and unstrapped the cock. She lay down and told Susie to pleasure her. By the time Mrs Smith had cum the headmaster was rock hard again.

Cheryl got up, strapped on the cock and laid down on the bed again. 'Come on Susie, come and ride me!' she said. Susie hesitated so the headmaster took her by the arm and told her to straddle Mrs Smith, which she did. She moaned as the cock easily slipped into her pussy.

Cheryl put her arms around Cheryl's neck and pulled her down to kiss her passionately on the lips, her tongue pushing into the younger woman's mouth. Susie groaned as Cheryl moved the cock slowly in and out of her pussy. She felt the bed dip as the headmaster came up behind her. With Mrs Smith holding her in place Adam was able to rub his hard cock around her little arsehole. A warbled sound emitted from Susie's mouth as she knew what was coming next.

She didn't have to wait long for the headmaster to slide his cock deep into her bum hole. Between them they both fucked Susie to three orgasms before Adam shot his load deep into her bowels.

All three collapsed on the bed and were resting when they heard a door close and someone walk along the hall and down the stairs.

'Sounds as if Peter has finished with Toby,' Mrs Smith said. 'I hope he's got at least one good fuck left in him as I've not had any cock so far,' she commented, unfastening the strap-on and walking out the door to the room Toby was in.

The headmaster fucked Susie for the rest of the afternoon and Mrs Smith took her urges out on Toby.

As they drove home Susie asked Toby if he was okay. Toby nodded but then said he never wanted to go back to the headmasters house ever again and that he just wanted his mother.

'Of course,' said Susie, knowing damn well she didn't mean it.

Croony
Croony
763 Followers
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  • COMMENTS
2 Comments
ToddHoffmanToddHoffmanover 6 years ago
Action Packed!

What a story! The headmaster and Mrs. Smith run a great school!

AnonymousAnonymousalmost 7 years ago

Complete and udder crap.

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Detention Previous Part
Detention Series Info

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