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The Management Trainee Gets His Reward Part 1

"The new trainee is cheeky and gets his just deserts."

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Author's Notes

"A management trainee is cheeky to the staff trainer. She threatens to report him but they reach a compromise. He gets strapped by the staff trainer who rewards him with a dirty weekend."

My name is Peter Brown and I am eighteen years old. I started work three months ago at a large retail store as a trainee manager. Today I am on a one day course taken by Miss MacDonald, the staff trainer.

Miss Ann MacDonald is in her thirties, straight blond hair, five feet tall, slim with large tits and wearing a low cut tight fitting red dress, stockings and red high heels. She is gorgeous and knows it.

I had got bored in the course and starting being cheeky to her. The result was that she ordered me to see her after work.

After everyone else had gone, I approached her.

“I am sorry, Miss. I didn’t mean to be rude,” I started.

“It does not matter about your apology. You were vulgar, and the group even laughed at one of your comments. You are a very impertinent young man, especially when you wolf whistled at me as I bent down. I will have to report you,” she stated.

“Please, Miss. I will get sacked and struggle to get another job,” I pleaded.

“I was only rude once, and that was to a teacher when I attended secondary school. I never did it again because I got my bottom thrashed,” she said.

“Perhaps I need my bottom thrashed,” I quipped without thinking,

“Are you seriously suggesting that I whack your bottom?” she enquired.

“If that means I don’t get reported, yes. I have never been punished like that before. You got a second chance at school and weren’t expelled,” I clarified.

“Oh. I need time to consider that. Come back when the store closes tonight,” she stuttered.

I left the room and reported to my counter until the end of the day.

&&&&&&

Ann sat at her desk after Peter left. She had a dilemma now. Did she take him up on his suggestion or just report him?

On one hand, she knew her duty and responsibility to the store. But she liked Peter’s free spirit, and it reminded of her, before she got thrashed. She also fancied him, he was tall and handsome. She knew he fancied her. The bulge in the trousers gave that away. Also, she felt aroused at the idea of thrashing him. However, there were practical difficulties. How would she get a strap and when could she do it?

Ann went online and, to her delight, she found a website that sold Lochgelly Tawses at reasonable prices. Even better was the fact they could deliver the next day. She immediately ordered two, one lightweight and one heavyweight, to be delivered in a plain package to the staff entrance the following day.

Next was the question of where. Work was obviously not an option, but she had a large house in the country with a cellar.

She realised that she had subconsciously made a decision and relaxed.

&&&&&&

At six o’clock, Peter returned to the training room and knocked.

“Come in,” Ann shouted.

“Have you decided, Miss?” he asked eagerly.

“Well, Peter. I have given the question a lot of thought. I do not want to ruin your career, so I will whack you. It will be one whack for every year, so eighteen,” she said.

Peter gasped as she said eighteen.

“It will be tomorrow evening at my house. I live in the country and you don’t drive, so I will take you. To save you the embarrassment of returning home that evening to your family, you can stay until Monday afternoon. I have spare rooms, so that is not an issue. Also, you will have two days to recover before work. Are you in agreement?” she continued.

Peter hesitated before agreeing.

“Bring some spare clothes, wash gear etc. and tell your parents that you are staying with a friend for the weekend,” Ann suggested.

“Thank you, Miss,” Peter said.

“You had better go now. I will see you tomorrow outside the staff entrance after work,” Ann said.

Peter headed off and rushed home.

&&&&&&

Next day, after work, Peter collected his bag from his locker and walked outside. Ann was waiting and swiftly ushered him away.He noticed that she was carrying a brown paper parcel.

“No one must realise we are together. Follow me at a distance,” she urged.

Peter followed and admired Ann as he walked behind. She was dressed in a tight fitting blue skirt, blue stockings, white clingy top and blue high heels. Her bum wiggled as she walked, and Peter was getting aroused.

Shortly after, they entered a car park and went to Ann’s car. It was about a ten-minute drive to Ann’s house, and Peter was shocked when he saw it.

They entered, and Ann showed him to his room. He returned soon after to discover that Ann had prepared a meal. After the meal, they went into the lounge.

“I thought that we would have a nice evening with a drink and then whack you before bed. Is that OK?” Ann asked as she poured two glasses of wine.

“This is some place,” Peter commented.

“It was my parents, and I inherited it,” she replied.

“I am pleased that you agreed to whack me. I am surprised that you got whacked,” Peter said.

“I was at a sixth form college in Scotland. I was eighteen like you and cheeky and got the strap a few times on my hands. That day, one teacher wound me up, and I ranted at her. She took me to the Headmistress, who told me it was eighteen whacks, one for each year, or expulsion. I took the whacks. She used the heavyweight tawse and on my bare bottom. It was done over a spanking bench in her office. I had never felt such pain. I learnt to behave after that. My parents spanked me when I got home with the note to add insult to injury. How about you?,” she explained.

“I was too young. It had been banned by the time I got there. Just detentions for me,” Peter replied.

The evening progressed, and Ann was pleasantly surprised how well they were getting on. It was a long time since she had been so happy with a man.

At ten o’clock, Ann looked up.

“Time for your first punishment. I decided it will be nine whacks tonight and nine tomorrow afternoon. I don’t think you will take all eighteen in one go,” she said as she stood up.

Ann went to the table and picked up the parcel, and opened it. Peter watched in amazement as she removed two leather tawses.

“Where did you get those?” he asked.

“Online by special delivery, especially for you,” she replied with a grin.

“Follow me,” Ann ordered as she marched to the basement door.

Peter followed closely and realised his cock was bulging now.

When they got downstairs, he was even more shocked. Ann had set up a full-length mirror on one wall and placed a chair and table in front of it.

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“I couldn’t get a proper spanking bench. You can kneel on the chair seat and reach over the back to grasp the table,” she explained.

Peter grinned. She had obviously thought this through.

“Strip off and bend over,” she commanded.

Peter slipped off his clothes but hesitated at his pants. His bulge was visible, but he did not want her to see it. Ann glared, so he took them off before bending over the chair. Ann smiled as she saw his erection.

Ann stood behind him and had the heavyweight tawse in her hands.

“Before I start, there are some rules. If you jump up or rub your bum, the whack does not count, and it will be repeated. You can wriggle and fidget between strokes. Every time you get a stroke, I will remove one item of clothing, hence the mirror. I am wearing nine articles of clothing. So I should be naked finally. In addition, if you take all nine strokes without any repeats, you will get a reward. Understand?” she said.

“Yes, Miss,” he replied.

Ann touched the tawse and Peter tensed. Before he knew it, the tawse had been raised high and hit his bum.

WHACK!

“Oooowwwww!” Peter yelled.

As promised, Ann removed her top before lifting the tawse high again. She crashed it onto his bum hard.

WHACK!

“Oooowwwww!” he yelled again.

Ann put the tawse down and removed her bra. Peter gawped at her in the mirror through tear-stained eyes. She picked up the tawse again, and it soon cracked onto his bum.

WHACK!

“Fucking hell!” he hollered.

Ann grinned as she slowly removed her tight skirt, revealing blue stockings, suspender belt and skimpy panties. Peter watched in the mirror but could not see clearly because of his tears. She lifted the tawse again and brought it down hard onto his bum.

WHACK!

“Oooowwwww!” he yelped loudly.

Ann slipped her panties off, revealing a blond mound. She continued, and the fifth whack followed.

WHACK!

“Oooowwwww!” Peter yelped as his bum was burning.

Ann carefully removed the suspender belt before delivering the next two whacks in quick succession.

WHACK!

WHACK!

“Bloody hell! Aaarrrrggggghhhh!” he screamed.

Ann then removed her shoes before lining up her tawse again.

WHACK!

WHACK!

She delivered the last two swiftly, to Peter’s surprise.

“Oooowwwww! Oooowwwww!” he cried.

Ann then kept her promise and removed her stockings. Peter lay motionless in position.

“Come on. I’ll help you down,” she offered.

Ann eased him off and wiped his eyes. Peter rubbed his burning bum before looking at Ann. She looked gorgeous, but he was unsure if he could touch her. One thing did stir, his cock. It was fully erect now and pointing at Ann.

“You took it better than I did. Now it’s time for your reward. Follow me,” she said.

Ann walked upstairs and then onto the first floor into her bedroom. She flopped on the bed, pulling Peter beside her.

“Your reward is shagging me,” she said with a big grin.

Peter could not believe what he heard. He slowly stroked her boobs, and she fondled his balls. He was not sure what to do next, so Ann eased his hand onto her mound. Peter slowly stroked her, and Ann started stroking his cock. Peter seemed unsure if he should put his fingers in her slit, so Ann pushed them in. Ann realised Peter was inexperienced and had to whisper into his ear. Peter stroked her clit and Ann started moaning. She was now desperate and pulled him onto her, slipping his cock inside her as she did. Peter slowly thrust forward before rhythmically moving in and out. Ann wrapped her legs around him, pulling him into her. Peter’s thrusts became harder and faster. Ann started panting and moaning louder until she screamed to an orgasm. Just after, Peter climaxed deep inside her, causing her to screech in delight.

They lay there for a while until Ann eased him off and cuddled up to him. They fell asleep in each other’s arms.

&&&&&&

The next morning came and Ann woke first. She cheekily stroked Peter’s cock until he woke up. Ann continued, and Peter teased her nipples with one hand and her clit with his other. Ann was in charge and pushed him onto his back, causing him to wince in pain. She swiftly straddled him and eased his cock inside her wet hole. Slowly she started riding him, pushing down hard and deep. Peter stroked her bouncing tits as she pounded away on his cock. She moaned and groaned loudly until she loudly climaxed. Harder and harder she pounded until Peter fired his love juice inside her. Ann slipped off him and licked his cock until it was dry.

After an hour, they got up and Ann made breakfast.

“Thank you for last night and this morning,” she said with a grin.

“Thank you. That was my first time,” he replied.

“I know,” she said.

“My bum’s sore. Do I have to be whacked again?” Peter asked.

“Certainly. But I will use the light one this time. Come on, let’s get it over,” Ann replied as she led him downstairs.

Peter did not wait when they arrived and jumped on the chair. Ann had grabbed the tawse and stood ready.

“Same rules, but I can not remove my clothes this time,” she said.

“Any reward?” he queried.

“Maybe tonight,” Ann replied.

Ann did not hesitate this time. She knew he was in pain so lashed the tawse down nine times in quick succession.

WHACK!

WHACK!

WHACK!

WHACK!

WHACK!

WHACK!

WHACK!

WHACK!

WHACK!

“Oooowwww! That’s unfair,” he yelped.

“It’s all over now. You can get down,” Ann said.

Peter slowly got down and rubbed his bum. His cock was now fully erect again.

Ann jumped up on the chair and bent over, revealing her blond mound.

“Now you have a choice. Whack me with the lightweight tawse six times or fuck me,” Ann exclaimed.

Peter did not need to think. He stood behind her and slipped his cock into her vagina. He slowly pounded away while holding her hips. In and out he pounded as she moaned loudly.

“Harder, harder, harder,” she shouted.

Peter pounded hard, pulling her hips towards him as he thrusted in her. Ann screamed as her orgasm came, just as he shot his juice inside her.

“Wow. Thank you,” Ann gasped.

“Thank you,” he replied. “You are a brilliant teacher.”

&&&&&&

The rest of the weekend passed with lots more lessons for Peter. On Monday she dropped him off near home in the evening.

He walked into his parent’s house with a grin.

“Good weekend?” his mum asked.

“Certainly was,” he replied.

“Are you seeing her again?” his mum enquired.

“May be,” he replied without thinking.

To be continued:

Published 
Written by OldPete2024
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