Olivia

(Author's note: chapters 1 and 2 of this have been previously published, so if you have read them already, feel free to skip to chapter 3)

Chapter 1 -- Beginnings

(note: this chapter starts slow, with a background story, if that doesn't interest you, skip to the stars ***)

Hi. My name is Olivia. This is the story of how I went from secretary to slave to wife.

It all started about ten years ago, when I graduated from business school, and went to work for my fiancée Jimmy, and his partner Bill. The company was small, and they couldn't pay me much, but I was in love with Jimmy, and figured once we were married, I would profit from the success of the company.

Shortly after that, Bill met and married Mary, the widow of a successful business man. His children from a previous marriage had inherited his business. Mary received an allowance from the estate to take care of living expenses. While she didn't have much money, she was still friends with some of her husband's business contacts, whom she introduced to Jimmy and Bill. Through them, the business received some much needed advice, and access to cash for growth.

As the business grew, Mary seemed to be more interested in Bill's money than in him. Jimmy enjoyed travelling more than Bill, and would often be away meeting with customers, and business contacts across the country. I became the office manager, in charge of all clerical staff and reported directly to Bill.

Bill was very smart with his investments, and soon had several homes. Jimmy always seemed to spend more than he made, and was becoming enamored with gambling. Jimmy kept avoiding the issue of setting a date, claiming that we couldn't afford it.

About 5 years ago, things started to fall apart. When I look back now, it all seemed to happen at once, but I'll try to put it in some sort of order. As I already stated, Mary seemed to love money more than Bill, and around this time she began spending more time at the beach house, and less at home. But my world started to crash when I had a girl's night out.

Some of my friends from college were in town for a business trip, and I took Friday afternoon off to spend some time with them before they left. Since Jimmy was out of town on a business trip, I decided to accompany them back to their hotel after dinner. As we waited for the elevator, the doors opened to reveal Jimmy locked in a passionate kiss with a little waif that was barely legal. He was so into her, he didn't even notice me as I ran off in shame.

I realized that I couldn't work for Jimmy anymore, and went to the office to get my things. Despite the late hour, Bill was there pouring over the books, and I could tell he was extremely upset. He could also see how upset I was, and he got the question out first. Through my tears, I told him what had happened at the hotel. I apologized for leaving him shorthanded, but said I hoped he understood why I couldn't stay.

Then Bill told me what had him there so late. He had just discovered that Jimmy had been embezzling, and there might not be a company for me to work for any longer. He assured me that Jimmy would not be a part of the company going forward, and asked me to stay. He needed someone that knew the company, and that he could trust to help him figure things out.

We spent all day Saturday documenting everything that Jimmy took. We contacted a forensic accountant, and a lawyer. On Friday, when Jimmy returned from his "business trip", we confronted him with our evidence. I told him we were through, and I was keeping the ring for "pain and suffering". The lawyer had drawn up a contract for Bill to buy Jimmy out of his share of the business, for a fair price, less what we could prove he stole. If Jimmy didn't sign it, we were prepared to send our evidence to the police.

Buying out Jimmy strapped the liquid assets of the company, as well as Bill's personal resources. We had to lay off most of the staff, and move the company into smaller quarters. I took a pay cut, in exchange for a small share of the company. Bill and I put in many long hours saving and rebuilding the company, and for a little while, money was tight. I wanted the company to succeed as a form of revenge on Jimmy.

One day when Bill got home, he found a box of his stuff from the beach house, and a note from Mary. She was moving to the beach house, and would live on the allowance from her first husband's estate, but wanted nothing to do with someone as poor as he was now. She would not ask for a divorce, because she felt that was "beneath her".

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About a year later, we made a major breakthrough in one of our products, and were able to sell the patent for a huge profit. The company was now back on its feet, and we could look into rehiring some of the people we had to lay off. Bill took me out to thank me for standing by him.

We both got very drunk, and ended up back at his place. We started talking about some of our kinkiest sexual fantasies, and playing a game of "I can top that". I said that I couldn't understand what would possess a woman to allow a man to dominate her, and he said he could show me.

He ordered me to get undressed. To this day, I'm not sure what possessed me, but I did it. He took of his tie, and used it to bind me hands behind my back. He then pulled me across his lap, and began smacking my bottom, gently at first, but building in intensity. Just as I started to think that I couldn't stand it anymore, he stopped.

His hand slid between my legs, and ne began to rub my clit, and finger fuck me. Just as with the spanking, he started slowly, and increased in intensity. I could feel the heat building despite myself, but just before I could come, he stopped. Before my brain had even registered that he had stopped, the spanking started again.

The cycle repeated itself over and over until I was delirious with lust. I begged him to let me come. I offered him everything I owned, promised to do anything he asked. He roughly pushed me to my knees, and opened his fly. Before he could ask, I took him into my mouth. I had never done this without my hands, and it was far from my best, but eventually I felt him jam my head against his crotch as he exploded into my mouth and throat. I hungrily swallowed every drop.

He untied my hands, and gruffly told me to finish myself off before leaving the room. I was stunned, and desperate, and did as I was told. When he came back, he led me to a bedroom. There was a comforter and pillow on the floor at the foot of the bed. He tied one end of his tie to my right wrist, and pushed me to the floor. He looped the tie around the foot of the bed, and secured the other end to my left wrist, and climbed into bed.

In the morning, I awoke to find him spreading a cream on my butt. He apologized, and said that he didn't know what had come over him. I told him there was no need, because I had enjoyed it, and wouldn't mind doing it again. I kissed him, and he picked me up, put me in the bed, and made love to me.

Over the next few weeks, we went out more and more often. A few months later, after dinner, I said we needed to talk. I had realized that it had been over a month since I had set foot in my apartment. And while I realized that he was still married to Mary, I felt I could save a lot of money if I moved in, and gave up my apartment. I wasn't asking for a commitment, and he could still date other women. He said in lieu of rent he expected me to be naked around the house unless he gave me permission. I agreed, and the next day, we picked up my stuff, and I moved in.

And that is how my life as a slave began.

Chapter 2 -- The re-emergence of Jimmy

Bill was the type of guy, that when he got into something, he had to learn all about. We joined a local club, and at first, we mostly just watched. As we became known as regulars, some of the other Masters introduced themselves to Jimmy.

From them, Bill learned about hiring trainers. Bill wanted to try everything at least once. Often, he would quickly decide he didn't enjoy it, or was afraid of the risk of injury to me, and we wouldn't explore it any further. Regardless of the cash price, some form of sex from me was always a part of the deal. Some of the lessons also included some contribution from the trainer's slaves for Jimmy, so he could tell if I was performing adequately. It may have been my imagination, but Bill always seemed more affectionate to me after these lessons.

We had always avoided the monthly slave auction, but one of the trainers insisted that it was an experience Bill should partake in to get the full feeling of the community. He explained to Bill that he could control how much of me was up for auction, and Bill agreed to give it a try.

Bill chose to be very restrictive for the first auction. I was to be auctioned for one hour, no whipping, no vaginal penetration, and he wanted to watch. Then for a little more control, he secretly gave a friend of his money to bid on me. While this was not a common practice, it was not strictly forbidden. Sometimes a Master would use the auction as a form of punishment, with the slave not realizing the winner was pre-arranged, and spending the day imaging the worst.

Bill brought me in back to prepare me for the auction, and that's where we saw Jimmy. He was on display in one of the auction cages, completely naked as we all were. His back was covered in scars from being whipped. His body was covered in tattoos and piercings, many in places where the skin is quite sensitive, and that would have been quite painful to receive. Most of the tattoos were quite derogatory. The most interesting were "man slut" tattooed up the crease in his ass, and the knobby ball pierced in his tongue. We had learned in one of our previous explorations that this was designed for extra stimulus when performing oral sex, especially on a man.

Bill made some discreet inquiries, and found out that Jimmy had gotten into excessive gambling debt with an extremely sadistic loan shark who was part of the community. To pay his debt, Jimmy agreed to become the loan sharks property. But Jimmy being rash, he never checked out the terms of the contract. Every month, he is auctioned off for one week, no restrictions. Any money received, is taken off his debt. If he fails to pay off the debt completely, he receives a tattoo or piercing as a punishment, and the cost of that is added to his debt. In between auctions, he sleeps in a dog house, outside the kitchen door, and services any request by the household staff. To add insult to injury. The cost of his food is also added to his debt. We learned that the loan shark always has one "pet" in his debt, and by the time their debt is paid off, their self-esteem is usually so shattered, that they are in capable of leaving, and are sold off to some of the seedier brothels overseas. As much as we hated Jimmy for what he did to us, neither of us wanted to see him treated this way.

Before the auction, Masters who had registered to bid, would mill around the staging area, evaluating the merchandise. A certain amount of touching was allowed, and even encouraged. I endured twists to my nipples, slaps to my butt, and even a few fingers thrust in my snatch. By the time the pages signaled the start of the auction, and directed the masters out, I was so horny, I would even have let Jimmy fuck me.

We had signed up early, so I was one of the first lots, and because of all the restrictions Bill had placed on me, there was little interest in me. Bill's friend had no problem purchasing me, and I was immediately brought into one of the back rooms, and prepared.

I was placed in a flesh colored body suit, and my breasts were pushed through openings that weren't really big enough for them. My breasts were being painfully squeezed, and were forced to jut out. There was no crotch, and I was completely accessible. Next two straps were placed around my butt cheeks, and just like the holes for my breast, were painfully tight, and caused the meaty part to jut out. Oddly enough, I found the pain to be extremely stimulating.

In the middle of the room, was a devise that looked like a sawhorse, except that it had a padded cross bar. I had seen this before, and had heard it referred to as "riding the horse". The padded area was adjusted to my torso, and I was laid across it. This left my head and breasts available at one end, and my pussy and ass at the other. The wrists and ankles of the bodysuit were fitted with locks that were now fastened to the legs of the horse.

The page announced, "Test commencing". I realized that some form of audio recording must be occurring. I felt a pinch to both nipples, "breast responsive". I felt a slap to each butt cheek, "butt responsive". I felt two fingers quickly thrust in my snatch, "already wet". When those same fingers were placed before my lips, I knew what was expected, and cleaned them hungrily. "Mouth adequate. Test complete".

I was fitted with a blindfold, and an O-ring gag, and felt a ball placed in my cunt, and a plug in my butt, both of which suddenly buzzed to life. The page then informed me that the one hour time didn't start until either the purchaser entered the room, or the auction ended, whichever came first. The auction was scheduled to last another three hours, and I was already dripping. I didn't know how I would survive this torture.

What seemed to be about a half hour later, I heard the door open, and a chain of some kind being attached below the horse. Next I heard Bill's voice, and felt relieved. "Thanks for doing this Jerry."

I knew Jerry, and considered him to be nice, Maybe this wouldn't be so bad. I figured the chain I heard must have been for his slave Lassie, named because he dressed like the star of the old TV show. "No problem. I have wanted a crack at that mouth of hers for some time. How do you want to do this? When I buy a slave, I usually fuck the mouth, while Lassie retrieves the ball. But if you want to participate, I'll give you choice of holes, or if you prefer, I'll have Lassie suck you off."

I listened intently to Bill's answer. "Actually I've wanted to try a spit roast for some time, so I'll take her ass, and you can enjoy yourself." I felt Bill's hand on me gently rubbing my ass, and playing with the butt plug. Despite the gag, I moaned hungrily, I was ready to pop.

"I see she doesn't have nipple rings, have you experimented with weights yet?"

"No, but now's as good a time as any"

"I'll just use the lightest ones."

I felt a set of hands that must have belonged to Jerry pinching my nipples, only when the hands left, my nipples were still pinched. I could feel the weight pulling them down , and a wave of pain spreading through my breasts, and ,my whole body. When it reached my pussy, it exploded into intense pleasure.

I felt the butt plug being extracted, and a lube being gently massaged into my crack. Then in one jerk, Bill slammed his whole length into me, causing more waves of confusing pain/pleasure to wash over me. If not for the gag, I would have screamed. I could feel my orgasm building, as Jerry thrust himself into my mouth. I was drifting off to another world, as a vaguely heard Jerry command Lassie to "get the ball". Her tongue had barely touched me when a body was wracked by an orgasm so intense that I passed out.

When I came to, I was on the couch in the corner of the room. The body suit, and toys had been removed, and I was dressed in one of my favorite sheer negligees. I hadn't even realized that Bill had brought it with him. I was cradled against Bill's chest. And Jerry was cleaning my face with a damp cloth. Lassie was on the floor taking turns cleaning both of them.

Jerry noticed my eyes move first. He brought over a huge bottle of water, and ordered me to drink it. I did so gratefully. As I drank, I was vaguely aware that Bill and Jerry were discussing the benefits of exposing me to overstimulation, but my brain was too fuzzy to follow. I finished the water, and fell asleep again.

I woke up in Bill's bed, which was odd because whenever I was in that room, I was always sleeping on the floor. Bill was gently shaking me. He had made me breakfast in bed. I guess he found my performance pleasing.

From time to time we talked about buying Jimmy in the auction. Bill would make Jimmy pamper me, and not be able to touch me. We never did, but the fantasy inspired some very passionate nights. After Bill's inquiries, word got back to the loan shark about what Jimmy had done. We heard that two of his new tattoos were "embezzler", and "adulterer" were inspired by us.

Chapter 3 -- Susan

When we bought Jimmy out, and were forced to downsize the company, I became both the office manager, and Bill's executive assistant. Now that the company was doing better, Bill decided that I no longer needed to fulfill both rolls. Our offices were adjacent, and Bill reasoned that one executive assistant could handle both of our needs.

As office manager, I already knew the abilities of all the clerical staff. I selected the top 5 candidates for Bill to interview. Even before the interviews started, I was sure that Susan would come out on top. Her skills far surpassed those of any one else in the company (even mine if I'm being completely honest). Plus she had that easy charm that would come in handy when soothing ruffled feathers, and wooing suppliers into offering discounts. This posed two problems. First, Bill found her extremely attractive, and didn't care if I knew it. Second, I was already aware that she had a strong desire for me.

The interviews went as expected. Her typing and organizational skills blew everyone else's away. She was studying at night for an MBA, which would certainly make her a valuable asset as the company grew. Despite my personal misgivings, we both agreed to give her the promotion.

Prior to Susan's promotion, we had complete privacy where our offices were located. Bill took advantage of the, and had several tie downs discretely located around his office. We would often indulge in "stress relief" during the quiet moments. Once Susan started, this became harder to accomplish.

One Friday, when Susan left for lunch, Bill called me into his office. As I entered through the connecting door, he locked his door, and ordered me to strip. He pulled a stool from the corner of the room, and ordered me to bend over it. As he was fastening cuffs around my wrists, I thought I heard my office door open. Before I could warn Bill, Susan entered through the connecting door.

We felt like two little kids caught with their hands in the cookie jar. Bill began frantically begging Susan not to make and EEO complaint, and not to quit. Susan stormed back through the connecting door, and we figured we had lost her. Then I heard my office door close and lock. Susan reemerged, and took her own clothes off.

She placed her hand on my butt, and breathlessly whispered, "My dreams have been answered, I've wanted a shot at that since I got here."

Bill was unaware that Susan was gay, and was momentarily taken aback. "That can be arranged, for a price."

Susan became obviously flustered, as she looked down and started to blush all over. "I've never been attracted to men", she mumbled. Despite her unease, the lust in her eyes when she looked at my naked body was unmistakable. Bill took this fact as a sign that it was safe to continue.

"She's worth it, but if you think the price is too high, you can leave us alone so I can enjoy my lunch." Bill went to a hidden drawer, and pulled out a pair of incredibly tall stilettos. They were so tall, that I could never walk in them, but then again I didn't have to. There were grooves in the floor that the heels could be locked into, and padlocks on the ankle straps. Bill put them on me, and I was secured into the floor, my legs spread obscenely, and my butt was raised just above the seat of the stool. My wrists were then fastened to the legs on the far side of the stool.