Control

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A retired headmistress has plans for an ex-student.
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Croony
Croony
758 Followers

Sara Scott was a sixty year old retired headmistress.

She had previously inherited a vast amount of money from her deceased uncle and now she was of pensionable age she wanted to spend more time doing what she liked to do, and that was dominating naughty young men.

She had always liked to tease the boys at her school but it was on her nights out with her friend Monica that she would snare a younger man and bring him unsuspectingly back to her home for a night of fun. She'd recently converted her cellar for just such nights.

She was always discreet and only targeted young men who she thought submissive. Her instincts had proven correct so far although she was getting tired of the chase as she got older.

Sara was tall, slim with short blonde hair and piercing blue eyes. Most people agreed that she was still a very good looking and classy lady.

Sara lived with her best friend Monica Nelson who was a fifty two year old legal secretary. Monica rented a room from Sarah. Monica was childless divorcee with a wicked sense of humour that Sara appreciated.

During the week Sara was becoming bored being on her own when Monica was at work. She had her swimming and yoga classes that kept her figure trim but other than that she felt she needed a hobby.

A few days before the school half term holidays Sara received a letter from a student asking if he could interview her for his GCSE A Level paper on life after retirement.

'Anything to relieve the boredom,' she thought so she wrote back with her telephone number asking him to call her to arrange a meeting.

On Friday afternoon her telephone rang and she answered, 'Hello!'

'Er.. h..hello Miss Scott,' came a stuttered reply. 'It's Tim Wilson here. I..er wrote to you about an interview for my examination project.'

Sara though he had a cute soft voice and that he was refreshingly nervous. Not wishing to prolong his agony she said, 'Ah, yes Tim. Thank you for calling I would be delighted for you to pop along and have a chat.'

They agreed that he would go round to her house at ten o'clock on Monday morning.

Sara decided she was going to dress up for the boy as she was feeling incredibly mischievous. She wondered if she dare lure him into her sex games.

On Monday morning Sara showered, put on some make up and dressed. She wore a tight crisp white silk blouse without a bra as her breasts weren't that big but her hard nipples pushed against the shiny material. This was tucked into a tight black pencil skirt that was held up by a thin leather belt and had underneath a black silk suspender belt holding up silky black nylons with seams running down the back. A pair of shiny black high heels complimented the outfit.

She stood in front of her full length mirror in the bedroom and admired the look. 'Yes definitely Headmistress material,' she thought.

At ten am there was a knock on her front door. Opening it she was more than pleased to see a good looking young man who nervously stood in front of her. 'Tim, good to see you. Please come in,' she said.

Sara thought Tim was very cute. Floppy blonde hair, blue eyes and a pouting mouth that looked even quite effeminate. He was slim and she towered above him in her three inch heels.

She led the way down the hall to the sitting room. Tim was enthralled by the way her hips rocked to and fro and almost groaned aloud as he noticed the seams on her stockings.

Once in the sitting room Sara motioned for him to sit on one of the couches. He was surprised she didn't sit on the one opposite but instead joined him.

'So Tim, what would you like to talk about?'

They chatted about her role in the running of the school and her involvement in many of the extra curricular school activities but when Tim asked Sara what she missed most he wasn't prepared for the answer.

Sara crossed her legs and as her skirt rode higher up her thighs she said, ' the control.'

'Er..w..what kind of control do you mean?' asked Tim.

'Young men need control. In fact they desire control,' said Sara recrossing her legs as her skirt rode higher up her thighs.

'Ho..how do you mean?' he asked.

'How old are you Tim?' Sara asked.

'Just turned eighteen Miss.' he replied.

Sara smiled that he had called her Miss but was surprised at his age as she thought he looked at least two years younger but then realised if he was finalising his GCE A Level examinations he would be about that age.

'Well you see most boys of your age and a few younger ones think that they are above authority.

They have to be put in their place and I found that by controlling them they went on to be better pupils,' said Sara.

'How did you control them?' he asked.

Sara crossed her legs again and paused for effect. She knew that Tim could see the tops of her stockings and one of the suspender clasps.

'I used to punish them, of course. They would be spanked hard on their bare bottoms until they cried. Humiliation was another good tool if I thought it necessary.'

'Humiliation?' asked Tim, staring at her long legs and the tops of her stockings.

'I used to make them strip completely and stand in front of me. Then I'd walk around them telling them what a naughty boy they had been. Often I would run my fingernail down their back or over their buttocks. Maybe on the inside of their thighs which would create the required effect. They would be standing in front of me sporting an erection which I would take in my hand and slowly stroke. Soon they would be begging me for release. I would then put them over my knee and spank them until they cried and they had lost their erection. That created the humiliation Tim.'

Tim snapped out of his thoughts when he heard his name and he realised he'd wrote none of this down.

'Usually though,' she continued, 'if one had been punished that way I would sit him on my knee and comfort him until he stopped crying then I would play with his cock until it was hard and jerk him to completion.'

Tim was silent. He couldn't believe what he was hearing but he'd never been so turned on in his life.

Sara noticed the bulge in Tim's trousers. She was having so much amusement at the boy's embarrassment.

Of course, none of it was true. She was having a bit of fun with the young man.

She decided to take things further though.

'Maybe you'd like to experience what they went through?' she asked. Tim went bright red and stammered some sought of negative reply, made his excuses and thanked Miss Scott before leaving.

As he was walking out of the door Sara called him back, 'If you want to experience what it is like to be controlled by me I would be delighted to show you. Just ring me and we'll set things up. Purely for research purposes, of course,' she smiled.

Tim slept restlessly that night thinking about what Miss Scott had said. Could he allow himself to be punished? Would she masturbate him? He thought about the spanking and came to the conclusion he wouldn't be able to take it but then he realised his cock was hard and throbbing.

The following evening he picked up the phone and called Miss Scott's number and nervously told her that he would like to experience a spanking from her.

She told him to go round at ten in the morning and she would be ready for him. He nearly groaned out loud on hearing that.

As soon as she'd put the phone down Monica asked, 'Who was that?'

'Oh just some work in progress.' Sara smiled and then began to tell Monica what had happened the previous day.

'Oh good you must tell me how it goes,' said Monica, mischievously.

Ten o'clock the next morning an even more nervous Tim knocked on Miss Scott's door. When she answered it he saw she was wearing the exact same outfit as the other day.

'Please come in,' she said as she again led him into the sitting room.

They both sat in the same places and Miss Scott asked, 'so Tim, why do you want me to spank you?'

Tim just shrugged his shoulders and whispered, 'don't know.'

Sara leaned back and crossed her legs. As she did so she watched Tim's eyes look at her thighs as her skirt crept up.

'Is it because you find it erotic Tim? 'Do you like the idea of an older woman controlling you?

Tim nodded.

'Strip!' was all she said. Tim sat stunned by what she had told him to do.

'Oh well, maybe this is a waste of time,' she exclaimed and made to stand bringing the conversation to a close.

'No, please wait,' panicked Tim. He sighed deeply and slowly began to undress.

Eventually he stood before her naked with his hands covering his rapidly swelling cock.

Sara stood up and told him to place his hands by his side then she stood up and walked around him, not touching him. He already had an erection.

She stepped behind him and pressed her body into his. Reaching round and taking hold of his cock in her right hand she began to whisper in his ear.

'You really are a naughty boy Tim, letting a stranger who is old enough to be your grandmother play with your cock.'

'You're all hard and excited about what I'm going to do to you, aren't you?'

'You want to cum, don't you Tim? Well you will but not until I let you. That's control.'

Suddenly she let go of his cock and told him to lean over the arm of the sofa.

As he did he saw Miss Scott unbuckle the thin leather belt around her waist and pull it through the loops of her skirt. 'Let's warm your bottom up first before I spank it,' she said.

Nervously Tim lowered himself over the arm of the sofa. His nose was on the cushion and his feet were flat on the carpet. 'Get that bottom up boy so I can see it.' she ordered

The first crack caused Tim to wince. The second was a little harder and he found himself inhaling deeply. The next three came in rapid succession but he managed to stay in position. The final one caught him at the top of his thighs and he moaned in pain.

'Good boy. Stand up.' Sara said.

When he did she noticed that his cock looked even harder. 'I think you like having your bottom strapped. Next time I must get down my tawse down from the loft.'

'Next time?' thought Tim

'Right. Time for your spanking,' she said as she unbuttoned her skirt and to Tim's surprise removed it. Tim could only gape at her long slim legs dressed in black shiny stockings with her equally shiny black suspender belt and tiny silk thong.

Sara sat down and beckoned Tim over her lap. He gingerly laid down, his cock slipping between her thighs that closed trapping his cock between them.

She started off by running her hand over his pale white bottom, feeling the contours and dragging her finger down his crack and over his little hole which made Tim shudder. He though he would cum if she carried on like that.

The first slap made him groan and pushed his cock deeper between her thighs. She wanted him to feel punished but she didn't want to scare him away so what followed was designed to be more sensual than painful. After five minutes it had that effect and Tim gasped that he was cumming and shot his load over Miss Scott's thighs.

She pushed him on to the floor and scolded him.

'How could you. Clean that up you little pervert.'

Tim went to stand to fetch a cloth or something but Sara grabbed his head and forced it between her thighs. 'With your tongue boy!'

Tim gagged as he licked his cum off Miss Scott's stockings and her bare thighs.

'Lick higher,' she ordered as his tongue found her panty clad pussy. Sara moved the gusset of her thong to one side to allow Tim's mouth access to her bald pussy lips.

'Pleasure me Tim. Lick my pussy,' she said as she pushed his face deeper into her thighs. Tim was then told where and how to give Sara the most gratification. Soon she was holding his head tight and fucking his face as his tongue alternated between delving into her moist pussy or licking her clitoris.

'That's it. Good boy. Oh God. Yes!' she said as she spurted her juices all over his face and into his mouth. After a few seconds she pushed him down on to the carpeted floor and marvelled at his cock which had regained its hardness.

She raised herself up and removed her thong then stood over the prostrate boy.

She undid the button on her blouse and slowly removed it. Tim stared at her small but perfect breasts with their erect nipples.

Sara sat down on Tim's lower stomach as Tim nervously waited to see what she would do next.

'So Tim, have you enjoyed me being in control?' Sara asked

'Ye..yes Miss,' he replied.

'Do you think you'd like me to control you a bit more?' 'I..I think so,' said a hesitant Tim.

Sara started to rub her bottom on Tim's cock that was nestled up against her arse. 'Can I ask you a personal question Tim?' Ye...yes okay,' he answered

'Are you a virgin?'

Tim nodded embarrassed.

'Oh good,' said Sara as she raised herself up and took hold of his cock.

Tim couldn't believe what Miss Scott was about to do but he groaned when she rubbed the tip of his throbbing cock between her wet pussy lips.

'Say goodbye to your virginity, young man,' as she sank down over his cock.

Tim was amazed at the feeling of having his cock encased by a warm velvety pussy.

Sara leaned forward with her hands either side of Tim's head and looking into his eyes she said, 'I own you now little boy. Do you understand?' Tim couldn't talk so he just nodded.

As she began to move her hips she told him how things were going to be from then on.

'When I text you to come to me you will. I will spank you, tawse you and flog you until I think you've had enough. I will masturbate you, fuck you and even rape your arse with my strap-on if I so desire.' When Tim heard that he moaned out loud and came inside her. Sara climaxed too.

Sara carried on riding him as she was pleased he hadn't lost his erection. She rode him to two more orgasms before Tim finally came again.

When they had dressed Sara gave Tim a long sensual kiss on the mouth. 'I want you here on Friday at six pm, please make whatever arrangements you need to. I'm planning a special evening,' she told him.

'Yes Miss,' was all Tim said before he left.

On Friday Tim arrived a little before six o'clock and knocked on the door. He was surprised when an attractive dark haired, middle aged lady answered.

'Hi, you must be Tim. Come in. I'm Monica,' she said. Monica hadn't been long back from work and was still dressed in her work clothes of a dark blue business suit, grey stockings and dark blue heels.

She led Tim into the sitting room but instead of offering him a seat she told him to strip. Tim looked alarmed and a bit scared.

'Oh don't worry. I'm fully aware why you're here. Sara has asked me to prepare you while she gets ready for you. Now come on, off with those clothes or do you want me to strip you?'

Tim slowly removed his clothes while Monica patiently sat on the sofa for him to complete the task. Once he was naked and was standing with his hands covering his crotch again she ordered him to come to her. She opened her legs so he could stand between them then she removed his hands. Tim's cock had began to swell.

Monica took hold of his cock and began to slowly wank him. He shifted nervously and wondered what Sara would say or do if she saw what the lady was doing to him. Monica saw his nervousness and told him not to worry.

'I'm only doing what Sara has asked me to do,' she told him. When Tim's cock was fully hard Monica leaned over and took it deep into her mouth. Tim couldn't believe what was happening to him. No one had done this to him before.

Monica slurped on his cock and took it deep into her throat, her head bobbing down and causing him to have the most pleasure he'd ever received.

'Oh God, I..I'm going to cum. Please you must stop,' he pleaded but Monica carried on her sucking until Tim groaned and tried to pull out of her mouth. Monica was ready for him and grasped his buttocks pulling him closer to her.

Tim erupted down Monica's throat. 'Mmmm, that was delicious,' she said licking her lips. Tim just stood there light headed.

It wasn't until he had calmed down that he realised there was a hard backed dining room chair in the middle of the room.

Monica led him over to it saying, 'I think you need to sit for a while until Miss Scott is ready for you.'

Dubiously Tim sat on the chair and Monica took hold of his arms and pulled them behind the chair back where she tied them together with a silk scarf and then with another secured them to the seat.

She then walked in front of the naked boy and secured his ankles to the chair legs.

Monica leaned over Tim and took hold of his cock. 'I hope you enjoy what she's going to do to you because next time you come over I'm going to be playing too.' Tim's cock was now rock hard as Monica kissed him deep on the lips and left.

Tim waited until he heard the click clack of Miss Scott's high heels on the wooden dining room floor before she came into the sitting room. The sight of her took Tim's breath away.

She was wearing a red leather corset that came up to just below her naked breasts, her nipples were hard. The corset held up dark grey stockings and on her feet were shiny red ankle boots. In her hand she held a black leather flogger.

'Hello Timmy,' she purred as she let the leather throngs of her flogger trail over his naked body. She walked behind him, leaned over and took hold of his throbbing cock.

'Now what shall I do to you tonight? Should I punish you first then fuck you or the other way round?'

Tim didn't move or answer. He was both excited and afraid.

'I know what I'll do. I'll fuck you first then punish you and fuck you again after you've worshiped my pussy.'

She threw the flogger to the floor and stood in front of Tim. She straddled his thighs and taking hold of his cock she lined it up with her pussy before sinking down on it. She placed her hands on the chair back, either side of Tim's head and started to ride him.

Her breasts with their large nipples were rubbing across his lips as she fucked him. 'Suck them Timmy, suck my nipples,' she ordered. Tim sucked and slurped on both of Miss Scott's nipples as she rode him faster and harder.

She looked deep into his eyes as she said, 'I'm going to cum Timmy. Oh God.' She screamed as her orgasm hit and she kept on fucking him until he finally erupted inside her. Sara climbed off him and untied his legs and released his arms from the back of the chair but kept them tied.

'Time for more fun Timmy,' she said as she led him through the sitting room and dining room towards the kitchen. In the kitchen she opened the door to the cellar and told Tim to go down as she held onto his arms so he wouldn't fall.

Tim gasped as he saw the room bathed in a soft amber light. It was pained in red and black, it had a wide bench with a leather top, a thick leather mat, what looked like a smaller version of a vaulting horse and many implements of torture on the wall.

'Impressive, isn't it?, Miss Scott asked. Tim was dumbfounded and said nothing. She stood him in the middle of the room and removed the scarf from his arms then held them up in the air and fastened his wrists to a bar above his head that he hadn't noticed. She pulled on a winch that lifted his arms up so he was standing on tip toes.

'Wha..what are you going to do to me?' he asked.

'I'm going to punish you.' was all she said before going to a shelf and selecting a small flogger and a horse whip.

She brought the whip down on his buttocks, not too hard but hard enough to make him shout in pain. 'Don't be such a baby Timmy,' she said before she delivered the next one. The third hit his meaty bottom and he gently sobbed.

Tim saw her go over to another shelf but couldn't see what she held in her hands. It was probably lucky for him that he couldn't. She squeezed a dollop of lube onto her middle finger and with one hand wrapped around his still throbbing cock she gently inserted it into his bottom. Tim moaned as she penetrated him and Sara was pleased to feel how tight he was back there. She finger fucked him for a minute while slowly wanking his cock.

Croony
Croony
758 Followers
12