Amy Teaches Her Boss

As usual no one having sex is underage. No STD's or COVID or meddlesome mothers-in-law exist here.

This is the third in a series. Reading Amy Learns Control and Amy Is Still in Control will allow this to make more sense.

Amy sat at the bar with her back to the man and woman who had just come in the private entrance to Cuffs. She was still trying to adjust to the fact that her boss was in a sex club.

"Jesus Amy, what are you going to do?" whispered Lucinda.

Pam spoke over her asking "Are you going to get fired if she catches you here?"

"Don't be daft Pam, she would have to admit she was here. She's not going to do that."

Amy started to giggle, partly because the situation was funny and partly as stress relief. Lucinda was right of course, her boss would not want it getting out that she frequented a place like Cuffs.

"Without breaking any confidentiality rules what can you tell me about that couple," She asked Lucinda.

Lucinda thought about it for a minute then said, "They always use a common room. They seem to enjoy an audience. It is unusual for them to come in during the week. They come mostly on the weekends so there is a larger crowd to witness their performance."

"Anything else you can tell me?" probed Amy.

Pam piped up, "I have been on duty a few times when they have come in. She is the dom, he enjoys a caning and for such a small guy can take an incredible amount of punishment."

"That's true. They both seem to like it when a stranger gets involved and takes over the physical abuse. It lets her verbally abuse him. She acts like she really hates him but when it's over they walk out arm in arm," Lucinda confirmed.

"So, they use a common room so random people can observe or actually be involved?" asked Amy.

"Sure, you could walk in with that mask on and she would probably single you out and ask for your help in striping the sub," said Pam.

"Is there any finesse or quirks to their scene?"

Lucinda shook her head, "No, it's actually kind of weird. It's almost like they want to hurry up and get it over as soon as possible. I don't think they are ever here more than 30 minutes in fact. They never have a drink or talk to anyone outside of the room. It's just wham bam thank you ma'am see you in a month."

"Curiouser and curiouser," Amy said thoughtfully.

"Uh oh," Pam giggled "Mistress is thinking about something."

"Yesss," She agreed slowly, "Anyone have a rubber band or a scrunchie I can use?"

"I do but why?" Pam asked turning toward the bartender. "Jerry hand me my purse, would you?"

Jerry retrieved her purse from behind the bar and she rummaged through it and came up with a scrunchie.

"Ok, I get it, you want to change your appearance some more," she said handing it to Amy.

"Yes, I'm going to put my hair in a bun. No one at work has ever seen me except with my hair down. That and the mask should get me by if I don't speak. Also, these 5-inch fuck me pumps add a bunch to my height. I pretty much wear flats at work."

"What do you hope to accomplish by doing this?" Lucinda wondered.

"I'm not sure really, something tells me I need to do this. I better get in there, if they are as fast as you say, I don't want to miss the main event."

The two girls hugged her and wished her good luck. Pam and Lucinda sat looking at each other for perhaps five seconds before hopping off their stools and nearly running to the control room.

Amy started down the corridor wondering what room her boss was in. She needn't have worried, there was the sound of sobbing coming from the second room on the right. The door was wide open, Amy heard the crack of a bamboo rod hitting flesh and a short scream before she got within ten feet.

She peered around the door frame just as she heard her boss Wendy say, "Oh for god's sake Charles don't be such a wimp. You have taken much harder from me in the past."

Amy was stunned. When she heard the name Charles, she realized she also knew the mousy looking man. She had seen him at last year's office Christmas party. He had been introduced as Wendy's big brother. Amy thought she was becoming accustomed to the various ways people got off, but this was really off the wall.

Charles was naked except for his socks. Considering the various fluids that had been deposited on the floor of the room this was probably a wise decision. He was bent over a hard wood table with his wrists handcuffed to conveniently placed rings. As Amy entered the room Wendy brought the bamboo rod down on his ass hard. It raised an instant angry purple welt and had Charles up on his tiptoes screaming.

"That's what happens when you can't absorb a little pain you worthless worm," Wendy exclaimed nearly purring. "Every time you scream you get it harder. Are you almost ready to cum and end your punishment you spineless shit?"

"No please, not yet mistress," moaned Charles.

Just then Wendy glanced over her shoulder and saw Amy just inside the doorway.

"Would you like to come in and help me with this piece of human garbage?" Wendy asked.

Without saying a word Amy smiled and swaying her hips slowly moved to her side and took the bamboo from her hand.

She moved into position carefully inspected the damage that had been done to his narrow ass. He had very little meat on him, Amy thought the intense beating already inflicted might be deep enough to bruise the bone.

She moved to his head and used the rod under his chin to lift his head so she could look into his eyes. They were bright and shining, there was pain in them, but also anticipation. Amy nodded to herself and moved back to his side.

Her first blow was not very hard and came down right at the juncture of his legs and ass. It got very little reaction from the sub, but she had expected that. She continued her medium hard strokes hitting the exact same spot every time. After five strokes the area was turning a nice red. After ten it was beginning to turn purple and she got her first sob from the tight throat of her victim.

"I was wondering what you hoped to accomplish with those tiny baby swats but now I see," observed Wendy.

"How about you, my worthless little turd? Are you enjoying your new mistress's technique?" she cooed into her brother's ear.

Almost as if it were against his will, he let out a moaning little sob.

Wendy smirked and drawled, "I think he likes it."

Amy turned and looked at her. She gave Charles another lick without turning and saw Wendy involuntarily clench her ass. Whoa, what is this she thought? She moved her point of aim down about two inches and began the same strokes as before, this time she watched Wendy out of the corner of her eye. The first few strokes had no effect on her but as soon as Charles made a noise she subconsciously reached back and caressed her leg right below her ass. By the time Amy had given him twelve strokes Wendy was breathing hard.

Son of a bitch Amy thought smiling to herself, my boss is a wannabe sub! That discovery had her very excited. Her tough as nails boss wanted to be abused! Did she even know that about herself? Was punishing Charles the way she vicariously experienced being disciplined? Her mind was whirling with the possibilities of this stunning revelation. If it were true what a perfect way to pay the hard ass cunt back. She had to do something to make sure she had read the situation correctly, but what?

She had the solution in a moment. She reached over and grabbed the woman's arm and brought her to the edge of the table. As she directed her blows to a spot at the very top of his ass, she carefully watched Wendy's subtle squirming. Amy timed it perfectly so that as Charles cried out, she used her free hand to land a hard blow on Wendy's ass.

The reaction of brother and sister was amazing. Charles started grunting and shooting his load on the floor without any other stimulation. Wendy, instead of grabbing her ass, bent over the table using one hand to hold herself up as the other went to her pussy. As Amy looked on, the tight gray leggings started turning dark from the juices flowing from her boss's pussy.

Amy smirked to herself, well I guess that settles that question, doesn't it?

Amy reached under Charles and jerked his cock to get the last drops of cum from it. He collapsed onto the table and mumbled, "Thank you, thank you, you are the best dom ever."

Wendy didn't say anything, only looked at Amy very thoughtfully. Amy gave her a nod and turned and left the room. She was met by Pam and Lucinda in the hall and hustled into the control room.

"We'll stay in here until they leave the building," explained Lucinda.

"My god, when you spanked her ass, I thought I was going to come," gushed Pam.

"So, it looks like you have a subbie slut for a boss, eh?" commented Lucinda.

"It kind of looks that way, it sure opens up a plethora of fun options I think," said Amy thoughtfully.

Amy was a little worried that Wendy may have guessed her identity so she dressed for work very carefully: ballet flats, hair long and hanging straight down, and a dark business suit with a blue blouse. After looking in the mirror she was satisfied that she looked nothing like the anonymous woman in Cuffs.

Wendy greeted her in her usual 'I'm The Boss' bitch mode. Amy carefully observed Wendy for the rest of the week. She couldn't detect anything in her behavior that gave away her secret. She knew it was there and it made the challenge of taming her boss all the more fascinating.

Relaxing in the tub on Saturday with her largest plug in her ass and her favorite dildo in her pussy she tried to come up with a scenario that would make Wendy her obedient sub. She rejected all the ploys she came up with finally climbing out of the tub and removing and cleaning her toys.

On Sunday she decided to start on the long put off chore of cleaning the basement. One of the few things her ex had agreed on was that there was nothing of value in any of the boxes and bags down there. She was going to fill both trash cans with some of the junk and haul them out to the curb for the Monday morning pick up.

As she was cleaning up, she opened a box that had some neatly coiled climbing rope, some carabiners and a couple of D rings. All were relics from her climbing days in college. The rope was nearly thirty years old and was certainly not safe anymore. That went in the trash the other hardware back in the box. When she lifted it off the table onto the floor it made a clinking noise. It reminded her of the sound her gym bag had made at Cuffs and she giggled to herself. Maybe she should open an in-home bondage business.

No sooner had the thought occurred than she paused and began to wonder why not. Not as a business but as a safe secure place to break her boss. If she cleared out all the junk there would be plenty of room to set up a very realistic torture dungeon. The more she thought about it the more excited she became. She knew it would take weeks to clear the basement out herself so she went online looking for a company to do the work for her. She found a company that would come in and remove everything and if they thought there were things of value in the junk, they would actually pay her to do the work. She wrote down the number so she could call in the morning. She would call from work, it would be fun to arrange while staring at her boss.

Her next problem was getting someone to build the room for her. She had neither the tools, skills nor desire to tackle that part of the process. Then she thought of Lucinda. Someone had built the rooms at Cuffs. They would probably be expensive, but they would be discreet. Lucinda seemed happy to hear from her and they talked for half an hour before Amy got to the point of her call.

"Sure, I know who built the rooms, they also do any maintenance or remodeling that needs doing. They are so discreet I can't give you their name or number but if you want, I can give them your email and if they are interested, they can get in touch."

Amy thanked her and after a few more minutes of idle chatter they hung up.

The next morning at work she contacted the cleaning company and made the financial and time details. It was a thrill to talk and gently tease her pussy while looking at her boss. On her lunch break she checked her home email. There was one from DBP and her heart raced a little as she opened it. It was a solicitation asking if the recipient needed any construction work done. She could either call or email if she were interested.

She practically ran to the elevator then impatiently rode it to the first floor. She entered the small park across from her building and called the number. A very polite, young sounding man answered the phone. She quickly told him what she had in mind, he told her he would be interested in doing the job. They made an appointment for the next night at seven.

The next evening Amy drank most of a bottle of wine trying to calm her nerves. Her doorbell rang at seven on the dot. She opened the door to a handsome 30-something man who introduced himself as Ned. After declining her offer of a drink, they went to the basement. After taking measurements and looking over the condition of the walls, floor and ceiling he had her describe what she had in mind specifically. Finally, he nodded and smiled, telling her he would have an estimate in two days and to keep an eye on her email.

She saw him to the door and as he was leaving said, "One more question, what does DBP stand for?"

He chuckled and replied, "Discreet Building Projects."

The next two days at work were torture waiting for a response from Ned. She seemed to be checking her email every ten minutes. At 3pm on Thursday she received the bid. She was right, it was expensive, but she thought taming Wendy was certainly worth the price. She emailed accepting the bid and asked when work could begin. Only ten minutes later she had a reply of 'next Monday if you like.' He sent a contract immediately and she electronically signed and sent it back. She was so excited she retreated to the restroom and fingered her pussy to a very satisfying orgasm.

The next three weeks were interesting watching the room take shape. She rushed home every night to see what had been done that day. She would hurriedly eat something then go online and order the whips, chains, restraints and other goodies she would need for entertaining her boss.

Amy had two sessions at Cuff's during that time. One was a new client, an older man, that had daughter issues and wanted to be whipped by his much younger daughter.

The other was a repeat with her first client. That time she had been dressed appropriately just by chance. This time she had time to prepare and charged into the room in an expensive evening gown. She berated her 'son' for being called away from a high society charity ball to deal with him. She wore elbow length cream-colored gloves that matched her gown. They were covered in rhinestones and made very satisfactory tiny welts when taken off and used as a whip. They were so successful that the client came within a minute of her starting his punishment. He begged her to have a drink and let him recover so she could continue to discipline him. She used padded cuffs to attach his arms to the legs of the table.

Lucinda was so pleased with her performance she called for a bottle of champagne on the house. While sipping the bubbly she related to Lucinda how her Wendy project was coming along. She confessed that she still had not thought of a way to lure her boss to her home. Lucinda had no ideas but said she would think about it and ask Pam for ideas. Her next problem was what to do for an encore with her client. After an hour she suddenly smiled and make her way down the hall.

One of the props of her costume was a long black cigarette holder. As she came into the room she make sure the tip was covered in saliva. Without a word she walked into the room, spread an ass cheek and inserted six inches of the holder into his ass. She slowly moved the remaining end in a small circle.

"Now you worthless little fucking worm mama is going to whip your ass raw," she quietly breathed into his ear. If this item comes out of your shithole the punishment will be severe."

"Mommy what will you do to punish me?" he whimpered in a tiny little boy voice.

Shw whispered even lower, "I will walk out of this room and never see you again."

A pitiful sob exited his mouth, "Mommy don't say things like that, what if it is an accident, or the pain is so much I lose control."

"You insolent little twerp, this is all about control, haven't you learned anything from me?" Amy hissed.

"I-I-I'll be good, I will control myself, you'll be proud of me." He said in a rush.

"Understand this, you will never, ever, make me proud you insignificant nothing."

"Whip me mommy, make it hurt, hurt your little boy."

Sitting in the bar later with Pam, who had just come in for a drink, she was stunned at the amount of money in the envelope the doorman handed her.

The doorman congratulated her saying he had never seen a man limping and obviously in a great deal of pain with such a huge smile on his face.

A week after the dungeon was completed the solution fell in Amy's lap. In fact, her boss brought it on herself. After work that Friday Amy was just sitting down to eat her supper when Wendy called. She was in a panic over some reports that had not been printed out for her.

"Thank God I found you. As you know this is a three-day weekend then I am taking a personal day before the conference in Jamaica starts on Wednesday," Wendy explained in a rush.

"I need you to go to the office and proofread, print and bind five copies of the Johannes and the Smith-Fines proposals so I can take them with me. My plane leaves at 11 pm."

"No problem boss, just leave it to me. I can access them from home, proof and print them. There is a print shop just blocks from my house that is open late. It's six o'clock now, come over at 8 pm and pick them up. My place is only half an hour from the airport. In fact, you can leave your car here and I will drop you at the airport."

"I can't believe how calm and efficient you are with this. I couldn't accept a ride to the airport, but I will see you at 8 pm," her boss replied as she hung up

Wow, not a thank you, or an I owe you or a goodbye thought Amy. Well, the days of not saying please and thank you would be over by 8:15.

Amy had no intention of doing any of the things she told Wendy she was going to. Instead, she used the time to make sure everything was perfect in the basement.

At first she used up her nervous energy arranging and rearranging her collection of well, tools. As the time crept closer to 8 pm she got calmer and more focused. A great deal depended on her doing this just right. Eventually, the security camera app on her phone showed a Jaguar pulling into the driveway. With a final deep breath she made her way up the stairs to her front door. She arrived just as the doorbell chimed. She smiled to herself, ask not for whom the bell tolls.

She opened the door and Wendy pushed past her saying, "I hope you got everything right, I don't have a lot of spare time."

"No problem, everything is ready for you in my office," Amy assured her.

"Well go get it then."

"My office is in my basement. It's a lot of paper. Could you give me a hand carrying it up?" Amy asked politely.

Wendy sighed and gestured down the hall.

Amy turned and led her to the stairs and then down. At the entrance to the dungeon she stepped aside and let Wendy enter first. As she entered she glanced into the four corners of the room to make sure the red lights on the cameras were on. As the door closed Amy picked up the rattan cane propped against the wall.

Wendy had stopped and started to turn around with a questioning look on her face. Amy slapped her across the face nearly as hard as she could.