Working at Boss's House Ch. 01

Due to Covid I agreed, as his secretary, to work at his house. We had always got on very well, lots of banter and just a hint of flirting. He was a very good-looking man in his mid forties. He played lots of sport and said he used his home gym most days. We had never discussed whether he was married or had been married. There certainly was no wife apparent in his life now.

As for me at 27 I had been married nearly eight years. I had been very immature and naïve when I married Steve. In the early days there had been plenty of sex but I had always felt there must be more to it than I was experiencing. My close female friends teased me calling me "Vanilla Vicki". It was not meant rudely as I had admitted that I had never tried many of the things they mentioned. I hadn't even heard of many of the things they mentioned. One of the girls said that if Steve was not delivering in the bedroom department she was sure that her husband would be delighted to widen my sexual horizons. When she mentioned things that we could try I was stunned. I thought at least a couple of the things she mentioned were pure fantasy. Nothing came of her offer for a number of good reasons but it had piqued my interest. Could I still experience sexual pleasure that had eluded me until now? At around this time I wasn't even getting much vanilla sex, as Steve seemed to have lost interest in me.

Working at my boss's (Tom's) home did change the atmosphere between us a bit. He was dressing more casually than he did in the office and said that I could dress less formally if I wished. I had always dressed in either skirts with a blouse or occasionally a dress. He seemed to notice my body more now that I was less formal.

He had an office set up in the house. I worked at a desk in the office but he said I was free to use the whole house. He qualified this by asking me to stay out of his gym, or as he referred to it his "playroom". His quizzical smile as he said this disarmed me a little. It was about the third day when he said he would be out for a couple of hours. He said to make myself some lunch and he would see me later.

As soon as the door closed I did what I had been dying to do since he had forbidden me to. My initial reaction was one of disappointment. At first sight it looked like I would expect a home gym to look. There was a frame designed to exercise the upper body in various ways from a sitting position and another to exercise the legs from a sitting position. There was a pommel horse that looked slightly out of place with various straps attached. One thing I could not identify was an eight-foot tall diagonal cross, attached to the wall. It looked like it could be rotated like a wagon wheel. This also had straps attached to it. Nothing prepared me for what I saw when I opened the large cupboard on the wall. There were canes, whips, handcuffs, blindfolds and some things I had no idea what they were. Although I had never seen one before I recognized what the large collection of penis shaped objects were. Some were massive far too big for any woman to be penetrated by. Some had switches on them. There was also a set of five mushroom shaped objects that varied from quite small to nearly eight inches tall. I was not to discover their purpose that day.

Now I knew why I was banned from entering the playroom. It was a gym but it was much much, more. The last thing that caught my eye looked like a saddle. From the middle of this protruded a small penis shaped object. Naïve as I was I was left in no doubt as to the saddles purpose. I wanted to mount it there and then. It would have been lovely to leave a sign of my sexual excitement but I thought better of it. Taking one last look back I went to the kitchen.

On the kitchen table was his personal laptop. I had never had reason to look at this as he used a different computer for all work matters. For some reason I could not stop myself from looking at the open screen. It appeared to be a story or at least the outline of a story.

There was a title and then a series of bullet points that went something like this.

Title: Working from home has its advantages.

Possible story line could include:

- Naïve but sexy secretary

- Secretary cannot resist going into the banned playroom

- She takes the initiative.

- Can he widen her sexual experience?

- Playroom activity recorded?

- He introduces her into the delights of ...........

Many of the things lists were the ones my friends had talked about. Now they seemed a little more real and alarmingly arousing. Was the story meant to relate to real life? Was I the secretary? Did he want to experience these outrageously exciting but daring things with me? I was shocked to the core by what I had read. I was intrigued, no sexually fascinated by what I had read.

I knew what I wanted to do and it was not getting myself lunch. I sat down at his computer and started typing.

"Chapter???.

She couldn't resist going into his playroom. Why had he banned her from it, she had to know?"

I typed exactly what I had experienced when I had investigated the playroom. I wrote the story in the third person as to write it in the first person felt too personal. Otherwise, it was just as detailed above.

I stopped typing knowing that Tom could be back within half an hour. I went back to the playroom wanting to take the initiative like the secretary in his notes had. All I could think of was to leave the door wide open. He would at least know I had disobeyed his instruction. I quickly grabbed a sandwich and returned to work. The main difference to the story was that my excitement was much stronger and my panties much wetter.

I heard him return but it was a few minutes before he came into the office. I could not look him in the face but he behaved just like normal. He had obviously not seen the chapter on his computer or the open gym door. My plan was not working out as I had hoped. It was a busy afternoon workwise. I spent the afternoon not only distracted from my work but also distracted from developing my fantasies. At about 5.30 Tom asked me if I was okay to complete typing the corrections to the report we had been working on. I had envisaged a number of exciting endings to the afternoon but this was not one of them. As he walked out of the room he added,

"I am going to send you a brief video I would appreciate you taking a look at it before you leave. Thanks for all your hard work this afternoon Vicki."

This intrigued me, as I couldn't think what the video would contain. I heard the ping to indicate an incoming message but finished the report before clicking on the attached file. The image that appeared was a view of a gym, an image of his gym. It was a few seconds before a figure moved into view. A female figure, my female figure. My body reacted as if I had been plugged into the mains. Had my initiative been what he had expected from his secretary in the story. Would it be enough for him to introduce me into the delights of sexual adventures and depravity the story suggested. I was excited to find out. I was transfixed by the video even though I knew exactly what it would show. As my figure disappeared from the screen Tom's face appeared on the screen.

"I loved your chapter for my story. I do so hope you will write another one tomorrow. Will the secretary succumb to the boss's charms? Will the naïve innocent woman enjoy the sex she had only dreamt of or will she crawl home to her vanilla husband?"

The picture of Tom zoomed out and I saw he was in his gym. I was standing in front of him within a minute. He looked me up and down as he sat on one of the exercise machines. His look was one of appreciation. He said nothing leaving me to make the first move. Remembering his story line I knew on this one occasion it was me that needed to make the move. It must have been the excitement flowing through my veins; I wanted him to see my body, all of my body, all of my naked body. What would he do if I was naked in front of him? I wish I could write that I did a striptease like a professional. Later he told me that it was the amateurism and embarrassment in my stripping that was very sexy. I started by taking my tight top up over my head. I have small boobs that mean I often don't need to wear a bra. At work I always wear one and today I had worn a seamless opaque one that showed my nearly black nipples clearly. My boobs may be small but my nipples are a good full size looking big as they point upwards from the gentle slopes. When, as they were then, they are erect they include the whole of the areola making them hard and long. They were feeling so tight that they were painful. I was tempted to take my bra off next but decided that I would keep him waiting a little longer.

I wished I had dressed more sexily. It would have been exciting to reveal stockings and suspenders but the next garment had to be my tight jeans. He had noticed them, or more accurately my tight bottom, the first time I had worn them to his house. I wondered how I was going to make the awkward job of removing them look sexy. I decided, slowly while facing away from him. I might have been naïve, but I did know that men more than noticed my bottom. Tom was no exception. I pealed the jeans down so that they just cleared my bottom. My panties were trying to go south with them but I was not going to let that happen. Looking over my shoulder at Tom he seemed to be loving the view. Getting each leg of the jeans over my feet was far from graceful but I did manage to avoid stumbling over.

After taking my jeans off I climbed back into my high heels because it was my belief that men find high heals sexy. I don't know whether Tom was one of those men but he gave me a lovely smile as I did so. I stood in front of him with my legs well apart in just my bra and pantie set holding his gaze. It suddenly hit me that this was not the finally. For the first time in many years I was going to show a man, other than Steve, my body totally naked. It scared me and excited me in equal measure. Would he get an erection if he had not already? Would he want to fuck me? Would I let him if he did?

I was suddenly in deep, very deep. It had been a bit of a game until now but now I was scared. If I backed down now I could be accused of being a prick-tease. I had asked for what had happened to happen. I had dreamt and fantasized about so much more. Did I need to stop things now? If I did I would never get to do all those things that sounded so different, so exciting and so beautifully disgusting. The more I thought about things the more aroused I felt. I was not going to let this opportunity pass me by it was far too good.

All these thoughts and questions flashed through my mind in a few seconds. On reflection I was never going to walk away from the excitement. The only decision was panties or bra first. I wanted to tease with the bra removal but it fell off my boobs as soon as I released the clasp. I grabbed my boobs and was shocked at how big and hard my nipples were. They felt wonderful and I wanted to show him just how sensitive they were. I rolled them between a finger and a thumb pulling them away from my small boobs until it became too painful. When I released the pressure my nipples were even more sensitive. I gently caressed them as a way of delaying the removal of my panties. I worried that, although I always kept myself well trimmed, I had never kept up with the trend to remove all or nearly all of my pubic hair.

As soon as I got my panties below my bottom I stopped worrying about my pubic hair. I had known I was very excited but I hadn't reckoned on that excitement soaking my panties. First I was embarrassed then I was kind of proud that I was that aroused. I did not hide my excitement I showed him how wet my fingers were. Having stepped out of my last garment I straightened up and looked Tom in the eyes.

"Are you going to fuck me?" I asked.

"Do you want me to?"

I couldn't look him in the eyes and dropped my eyes as I very quietly answered, "Yes".

"You have a choice do you want me to fuck you now or do you want me to start showing you all those things that you have never experienced? You can go home and be fucked but you may not have the option of going home and experience some of those, until now, forbidden fruits. The decision is yours Vicki."

My friends' nickname flashed through my mind. Was it me that had been vanilla all these years or was I right to be blaming Steve? Tom was right it was decision time and it was me who needed to make the decision. It was frightening but I knew I would never forgive myself for turning the opportunity down. I wanted to experience things like; oral, anal play, spanking, enemas, domination / submission and humiliation. There were other things that I had forgotten or had no idea what they were such as watersports and DP. It clearly wasn't swimming or waterskiing.

"I want it all. I can't wait, please show me all the things on that list and as many more as you can think of."

"Let's take it slow, tiger. There is time for you to experience everything you wish but let's start with something easy."

I felt a little deflated by his answer until he looked at me and said one simple word, "masturbate". I had never masturbated in front of anyone. I suspected he sensed this. The idea alone injected a shock to my systems. I was determined to comply with anything he suggested. I looked him straight in the eyes and found my swollen clit. It felt wonderful, forbidden and down right dirty. I was shocked at how aroused my pussy and clit were. I have never been quick to become aroused or to climax. This felt different, so different. I am sure if he had told me to orgasm I would have been powerless to prevent it. He didn't, in fact he said almost the opposite.

"If you chose to masturbate to orgasm you will orgasm three times before leaving this room."

Typically I experience three orgasms in about six to eight weeks. He clearly had no understanding of my body. Having said that I was being confused about my body myself. If I didn't stop playing with my clit it felt like I would explode within seconds. I was far too confused and excited to think rationally. My knees buckled, two fingers slipped easily into my pussy as my thumb strummed my clit with dramatic results. I loved it. I could not remember an orgasm so strong and long lasting. My knees gave in completely and I finished my extraordinary climax lying on my back fucking my flooded pussy with two or three demanding fingers.

I lay there stunned by the fact that this man had given me a life-changing climax without even touching me. What the hell would he be capable of when educating me into his list of frightening experiences? It was at this stage that I remembered that I had, kind of, agreed to have two more orgasms. I knew it would not happen but wandered how he thought he was going to induce such a reaction in my satiated body. He seemed to read my mind, as he had since we entered this room.

"You seemed to be fascinated by the Sybian earlier. I think it is time to introduce you to the delights of 'total fucking'. No man can replicate what the Sybian can do. I have seen women pass out riding the Sybian having cum so violently and so often their bodies could take no more. I will love watching you. I would love it if you took it as a challenge to beat the machine. If you can ride it for 20 minutes without cumming I promise to offer you any sexual pleasure you desire at any time. If you cum in those first 20 minutes I insist that you ride it for another 30 minutes or until you cum again. Do not worry you will not last another ten."

I thought my orgasm had ended any interest in sex that I could have harbored for the rest of the day. I was wrong. His words had ignited a flame, a small flame but a flame nonetheless. I wanted to know more about the Sybian. I suspected it was the saddle like thing I had seen earlier but was not certain. It was confirmed when he led me to it. He told me that there were lots of options and that the penis shaped attachment was the smallest dildo but there were also attachments that did not penetrate but only stimulated the clit. He said that I was to mount the saddle and let the small dildo enter me fully.

I was excited by the prospect and was soon in place. He had applied a clear lube to the dildo but I am not sure how necessary it was as I was still very wet and aroused. He told me to put my full weight onto the saddle. When I did it started to vibrate gently but devastatingly. Nothing had prepared me for this. Penises were not made to do this but the Sybian was. I was instantly interested, instantly buzzing and feeling far from satiated. Then I remembered the challenge. Why not take it on. The feelings this machine was creating in my body were wonderful. It would be a great pleasure to 'suffer' them for 20 minutes. I would prove I knew my body much better than he did.

How naïve I was. He simply turned the machine up and the game changed. Now it was a challenge I doubted I could win, but I was going to give it my best. He laughed kindly when he read my mind. My body was soon building towards a second orgasm. I thought I was having some success until I realized that he had turned the machine down to low.

"Only another 17 minutes to go. Do you still think you can win the challenge?"

As he turned the vibrations up I suspected he was playing me with no intention of allowing me to climax quickly. I suspected he knew he had me completely where he wanted me. On the brink of orgasm that he could induce whenever he choose. Part of me accepted my fate while a very small part of me kept fighting. It was an uneven battle one I was destined to loose. The vibrations were going to bring on a spectacular orgasm but when the small dildo started to rotate as well as vibrate I was helpless. Helpless to prevent myself losing the bet and losing any remaining control of my body. The spasms were violent and I found myself impaling myself as fully as the small dildo allowed. At that moment I wanted the dildo to be huge, to rip the orgasm out of me. The orgasm hit me but at the same time the pressure around my clit and bladder became so painful I lifted myself off the dildo. As I did so I exploded forcing fluids at great pressure onto the saddle below me. I squirted huge quantities of fluids in bursts that stopped and started in time with the spasms of my orgasm. It was both beautiful but also nearly too much pleasure.

He caught me from behind as I collapsed backwards into his arms. It was the first time he had touched me since we entered the room. He was undemanding until he whispered, "you promised". He was lifting me onto the saddle that had now got a much bigger penis attached. I was too exhausted to fight it and the huge dildo was soon deeper than anything had ever been in my pussy. He sat behind me and supported me. My body was floppy and I was unable to support myself. He supported me as my body became accustomed to being stretched by the dildo. Accustomed but also aroused by it. My pussy started to pulse as if trying to milk the dildo as you might a penis.

It was at this time that Tom started to quietly tell me a fantasy. He told me to imagine that I was leaning forward on the Symbian's cock. Behind me was someone who parted the cheeks of my bottom and licked my anus. They became more aggressive with their tongue as the dildo vibrated in my pussy. I was imagining it was Tom tonguing my bottom. When he whispered that I was to imagine the huge dildo penetrated my bottom it shocked but excited me. Was he going to ask me to actually do it? If he was he was too slow as the fantasy of it was more than enough to trigger a painful but pleasurable orgasm as the huge dildo found places never before found. I didn't pass out but understood how easy it would have been to slip into unconsciousness as by body was flooded with raw arousal.