The Deal
It was 4:45 in the evening and Mary was just finishing things up for the day when a message popped up on the internal messaging system.
‘Please come to my office when you are done with your work, Mr. Brenner, CEO’
Mary was a bit startled. It wasn’t normal for the CEO to ask her to come to his office this late in the day. ‘He can’t have found out… no that can’t be it’ she thought. She logged off her computer and made her way to her boss’s office. She knocked on the door and heard him call out “Come in.”
“You wanted to see me sir.”
“Ah yes, please have a seat, Mary. There is a couple of things I wanted to discuss with you.” Mr. Brenner said.
Mary sat down on the chair in front of his desk. Mr. Brenner steepled his hands in front of him.
“Mary, do you know what my degrees are in? I majored in business of course but I also minored in finance. Now I don’t have the time to devote to all the accounting of this business which is why I hired you. An Accountant. But I do still like to check the books roughly once a month to make sure things are going smooth.”
As he spoke Mary’s face started to pale.
“And do you know what I found when I looked over the books today. Well, some of the numbers didn’t add up. So, I started digging and came up with a very disturbing conclusion. You’ve been stealing from me Mary. If my math is right, and I’m pretty confident it is, you’ve stolen nearly $100,000 from me so far. I have all the evidence here in front of you and it’s pretty damning. I called for this meeting so we could discuss your options before getting the police involved.”
“O-options sir?”
“Yes Mary, you do have some. Option 1: Pay back the money right now and I’ll let you resign though you’ll have a hard time getting another accounting job in this city with my contacts.” Mr. Brenner told her.
“Sir I-I already spent the money. I don’t have enough.” Mary uttered fearfully.
“Well then, we have option 2: I call the police and give them all this evidence. It should be a pretty easy conviction. You didn’t hide your tracks well at all.” He said gravely.
“Please sir, I’ll do anything to avoid prison. Please don’t call the cops.” Mary said sobbing now.
“Hmm, perhaps there is another option. Other than breaking my trust and embezzling from my company you are a good accountant. How about this, Option 3: For the next year you will serve me any way I wish for one hour per workday. And I mean any way I wish. Without complaint. There will be some pain but nothing permanent and much of it will be sexual. If you can manage to follow my instructions and serve me well for a whole year, then I will give you both copies of the evidence I have. I’ll also let you keep your job as I’m sure by then you’ll have learned your lesson. Or if after the year you decide to seek other employment, I’ll give you a glowing recommendation. But until that time you’ll continue working here and at the end of each workday you’ll come to my office. After everyone has left, I’ll have one hour to do whatever I wish. You will not be allowed to tell anyone of our deal, and I won’t speak of the theft. You won’t even have to pay back the money because you’ll be paying me back another way. This is the deal I offer to you. If you agree and then break this agreement the evidence will go to the police. Do you agree?” Mr. Brenner said sounding like he might have rehearsed that beforehand.
Mary was frantically thinking. She was in big trouble now. She could go to prison for embezzlement, or she could serve as a sex slave to her boss for a whole year. Although it’s only an hour a day 5 days a week. Surely, she could survive that. Mr. Brenner was known for honoring his deals. Once he gave his word he always followed through. It’s part of what made him so successful. He had a sterling reputation. But could she really debase herself so much to serve as a slave to him. She realized with cold certainty that she didn’t have much of a choice. Between that and prison it really wasn’t a difficult choice.
“I-I a-accept sir.” She finally said meekly.
“During our hour together, you will call me master. Now, it is Friday so we will start on Monday. After the workday is done, you will come to my office and wait. Once the building has cleared out, I will instruct you to undress. You will do so in as appealing a matter as you can manage. I will give you further instructions then. This weekend I want you to go to a salon and get your vagina and asshole waxed. I don’t want any hair there on Monday. For the next year you will keep both areas either shaved or waxed. Do you understand?”
“Yes Master.” She said with her head bowed.
“Good. You can wear your usual office wear into work. If I want you to wear something different, I will tell you. I have one copy of the evidence here and the other stored securely somewhere else so don’t get any ideas about destroying it. You’ll get both copies along with my oath that I didn’t make any others when your year is up. You may go for today. Don’t forget my instructions. I’ll see you on Monday.” He said with finality.
“Yes Master, thank you Master.” Mary said. She would do everything in her power to do as he wanted and keep from going to prison. If it meant she had to bow and scrape to him it wouldn’t be the worst thing. He was a fairly handsome man. Mid 30’s, same as her. Sandy blond hair and blue eyes. Standing about 6’1″ — 6’2″. Under different circumstances and positions she could see him being a potential hook-up. But circumstances being what they were she was downcast as she made her way home.
Mr. Brenner, or Greg to his friends and family, smiled slightly to himself as Mary left his office. He wasn’t the type to make moves on his subordinates. That’s bad for morale and opens up the company to scandals and drama. But he couldn’t deny being attracted to Mary since she started. Standing at 5’6″ and petite around the middle. With breasts that were just on the big side of proportional. Her long red hair and shining green eyes sparkling with intelligence really drew him in. He was a professional though and kept all their interactions business appropriate. But Greg was also a smart man, and he knew when he found the evidence she was stealing from him, that he could manipulate it to his favor.
He logged off his computer and locked up the office on his way out, arming the security system. He had preparations to make this weekend.
Mary did as instructed over the weekend. She found a salon that specialized in the kind of waxing Mr. Brenner wanted done. She also bought some lotion to soften the areas waxed and lessen the regrowth to make future shavings or waxings easier. She didn’t have a wild amount or anything she kept a neat landing strip above her pussy. She had tried going bald a few times but wasn’t a fan. Oh well, no help for it now, she thought to herself. With that done she went home to try to relax as much as possible while dreading Monday.
Greg enjoyed his weekend. He stopped at a sex toy shop and bought a few things he thought would make the hour-long sessions more enjoyable. At least for him, he thought.
Monday
Monday came and Mary worked as she usually did. She showed no outward sign of distress except maybe being a little quieter than usual. At 5 o’ clock she logged off and while everyone else was heading home she made her way to Mr. Brenner, no Masters, office. She knocked on his door.
“Come in.” He said.
Mary entered the room and closed the door. Greg was watching the security cameras to see if everyone was gone for the day. When the last of his employees left, he turned off his screen and turned to Mary.
“Undress for me.”
“Yes Master.” Mary said
She started to unbutton her blouse as appealing as she could. Not quite a strip tease but as sexily as she knew how. Master seemed to be pleased. She continued until she was in her underwear. She unclasped her bra and bent at the waist to hide her tits while she pulled down her panties. Finally, she stood up fully exposed for him to view.
“Good job, now spread your legs and put your hands behind your head with your back straight.” He commanded.
“Yes Master.” Mary said as she got into the position he told her.
Greg walked around Mary admiring her. He bent down and pulled her ass apart to check for hair. Finding none he was pleased. He came back around to the front of her.
“I see you followed my instructions well Mary. I’m pleased. Here’s how this is going to work. On Mondays you will be getting the punishment portion of your sentence. What that means is spankings, paddling, and sometimes caning. As I said I won’t do permanent damage, but I will make sure the lesson really sinks in. We will go until I feel the lesson is concluded and you will finish the session by sucking me off. The rest of the week will be played by ear, but I want your sore ass to be a reminder all week that stealing from me is a bad idea. Do you understand?” Greg said.
“Yes Master, I understand.” Mary said trying not to cry.
She was scared but was trying not to show it. Greg pulled a chair to the center of the room. This chair had no arms on it, and he sat down and made himself comfortable.
“To start, you will lay across my knees. Put your hands on the ground on the other side of my legs and keep your ass up.” He commanded.
“Yes Master.” Mary said as she got into position. It was uncomfortable but she knew it was about to get worse.
Greg caressed her ass for a few moments, enjoying its softness before lifting his hands and bringing it down with a crack.
“Ahhh!” Mary screamed.
Greg started smacking with abandon. He’d smack one cheek a few times than switch, or he’d alternate between each smack. He wasn’t hitting with all his force, but it was still powerful blows. Mary let out short screams or whimpers as the beating continued. After 10 solid minutes Greg slowed to a stop and admired the redness of her ass.
“Stand up slave.” He said.
“Yes Master.” Mary said sobbing quietly as she stood a little shakily.
Greg pulled a longer padded table over from the corner.
“Lay on top of this.” He said to her.
Mary walker over to it and laid facedown when he indicated to do so. He fiddled with something under the table and pulled up some straps. He strapped her down and then began manipulating the supports of the table until it started changing shape. He dropped down the part under her legs presenting her sore red ass. It also slightly lifted her torso.
“My hand is starting to sting a bit from the spankings, so I thought I’d move on to this guy for a bit.” He said as he walked into Mary’s view with a leather covered paddle. He swung it in the air a few times to show her how well it moved. With that he walked back out of her view.
He ran the paddle along her red ass drawing a gasp from her as the sting from the spankings came back with the dragging paddle. Then the first swing came.
“Ahhhhhhh!” Mary gave another scream. This hurt worse than the spankings.
Greg didn’t focus exclusively on her ass he also made sure to tan her thighs. Inside and out. Another ten minutes of this and he put the table back to right and unstrapped her.
“How are you doing slave?” Greg asked her.
Mary was sobbing but she answered. “It hurts sir. Thank you for teaching me my lesson.”
Greg was pleased with her answer. “You’re almost done Mary. You’re doing very well. Take the position I had you in when you first got undressed. Legs slightly spread, hands behind your head, back slightly arched this time.” He said soothingly.
Mary Stiffly moved into position. Her ass and legs were on fire, but she told herself she could get through this, and she would.
Greg came up in front of her and said, “this will be your last punishment for today.”
With that he struck down on one of her tits with his palm. He left a big handprint shaped welt. Then he did the same to her other tit. He hit each one 5 times before stopping. Each tit was now red and throbbing in pain. Mary whimpered as her body shook with pain.
Greg walked back to the chair with no arms. He undid his pants and pulled them down before he sat.
“All that’s left is to get me off slave. Once that’s done you can get dressed and go home for the day. You will swallow my load and clean my shaft before I’ll consider this task done.” He told her.
“Yes Master.” She panted out from the pain as she walked over to him and dropped to her knees. She reached out and took his rapidly expanding cock into her hands. She opened her mouth and lowered her head onto his rod. Mary wasn’t a stranger to sucking cock. She’s done it for previous boyfriends and a couple hook-ups. She doesn’t love doing it, but she doesn’t hate it either. It’s something that made the guys in her life happy, so she did it for them. She knows how to make a guy cum. She took his cock deep into her mouth until her lips were at his pubic bone. Then she bobbed back and forth a couple times before pulling all the way back till just the head was in her mouth while she swirled her tongue around the head. This whole time she was fondling his balls with her hand. She popped the dick out of her mouth and used her other hand to continue stroking it while she lowered her head and took each ball into her mouth one at a time and giving it a sensuous lick before diving back down on his stiff member. She worked her tongue as she bobbed up and down taking it all the way into her throat before coming back up. Soon he was bucking his hips and moaning while running his hands through her hair. Then without warning he erupted into her throat. Several ropes shot onto her tongue and down her throat and she dutifully swallowed them all. She wasn’t the biggest fan of the taste, but it was tolerable. She used her tongue to clean his shaft as it started to deflate before sitting back, being careful not to actually touch her ass to her heels.
“That was great. Well done slave. You are done with your first day. The rest of the week should be less painful but no less strenuous, so try to get some rest tonight. Oh, and I have a request. This isn’t an order and its up to you. Have you done anal before?” Greg asked her.
“No Master. I haven’t found the right partner for that yet.” She replied.
“Hmmm, pity, because you are going to get fucked in the ass during your time serving me. I bought something that might make it easier for you.” With that he pulled out a little box and opened it showing her a sterling steel butt plug.
“I figured I’d let you decide if you want to wear it, but as I said, you will be fucked in the ass so working on stretching it would probably be a good idea. I’ll let you take this and the bottle of lube I bought. You can decide later if you want to use it or not. That’s all for today. You can get dressed now and leave. I’ll see you tomorrow.” With that he turned his monitor back on and started working on something on his computer.
A little stunned at the quick dismissal Mary dressed as quickly as she could while still throbbing all over from the beating she took. She grabbed the butt plug and lube before she left and stuck them in her purse. She headed home to draw a warm bath and try to soak some of the pain away. After her bath was done she considered the butt plug. She wasn’t too sure about it but what Mr. Brenner had said was true. She didn’t have a choice in whether or not he fucker her ass and stretching it before hand would probably make it easier on her. She decided to wear it for the night and see how it goes.
She lubed up her finger and slowly pushed it against her asshole. She slowly worked it in before pulling it back out and applying more lube. She kept up this process until she got one finger in to the second knuckle then repeated the process for a second finger. When she felt she had enough lube in her ass and it was sufficiently prepared she covered the butt plug in lube and slowly pushed it into her asshole. It was bigger than her fingers and made her feel uncomfortably full back there, but she pressed on. Finally, she felt her sphincter close around the flared edge of the plug. She still had the base sticking out and it didn’t seem to be coming out. It felt weird but it was stable for now.
She dressed in a loose fitting t-shirt to not aggravate her throbbing nipples and a pair of soft panties. She went about the rest of her nighttime routine. She made dinner, watched some TV, tidied up the house a bit. She was unable to find a position to sit that didn’t cause her bruised ass to throb. The whole time she was aware of the butt plug but it was becoming more normal as time went on. It didn’t feel as uncomfortable and while it wasn’t natural, she was thinking about it less and less. Finally, she went to bed. She would need a good night’s rest to let her body recover and be ready for tomorrow.