Chapter 1

People always say "Jill, you get whatever you want". Things in my life have always worked out the way that I wanted them to. I was a successful businesswoman, Vice President of Marketing for a large company in the Chicago, living in the most elagant neighborhood in our town. At 36, I kept in excellent shape by working out 3 times a week and eating right. My figure was a tight 36DD-24-32 and I was proud of it. I felt that I looked as good now as I did back in college. I was married to my college sweetheart Don and things were pretty good between us. We have been married 14 years, no children and Don was having a pretty good career. I often felt that he was jealous of how fast I moved up in the corporate world. I was making 3 times his salary and yet it never really bothered me.

My neighbor and best friend Betsy, who at 50 has a better body than anyone I have seen. Large firm breasts probally 34DDD, a tiny waist, long legs and a flat stomach after giving birth) and I were sitting down one Saturday morning drinking coffee and chating about our life's when she told me that her son Jon would be moving back to Chicago from college. It seems that he wanted to take some time off and get an apartment. I asked Betsy "How do you feel about him leaving school?" She told me "Well, I am upset, but ever since Dave passed away two years ago in a plane accident, Jon has really been struggling. Then his girlfriend had broken his heart, so I am trying to understanding." Betsy then asked me a favor. She said "Jill, is there any way that you might be able to help Jon get a job with your company?". I knew that Betsy had been through alot, with the death of her husband and trying to get Jon to graduate and goto school, I knew that this was the least I could do. I told her that I didn't see why not and to have him call me later today and I would let him know what was available

We spoke of other things and then I said "Betsy I think that since I got this last promotion that Don doesn't want to sleep with me." Betsy laughed "That's silly Jill, of course he wants to sleep with you, you are gorgeous." I told her "we have only had sex twice in the past 6 months. I try to have sex with him all the time, but he is either too tired or not in the mood". Betsy gasped "are you serious, oh you poor thing". We carried on with our conversation and Betsy told me that if I ever needed a shoulder to cry on to let her know and we left it at that.

Jon called me later that afternoon and I barely recognized his voice. He had grown up a lot in the two years since he had been at school and he sounded like a nice young man on the phone. I told Jon about the openings that my company had and he said that he was most interested in working in our mailroom. Sorting and delivering the mail throughout the company. I put him on hold and spoke to the supervisor and set up an interview. A few days later Jon had the job.

Life continued on like normal with Betsy and I working out 3 times a week and me not getting any sex from my husband. I didn't understand any of this. I always dressed nice. I wore business suits that were knee length and jackets and I still saw men look at me. Despite how much I was in control of my life, I really felt that I had a submissive side to me. Betsy and I would talk about our fantasies and I would often tell her that I would love to be submissive for Don, let him take control and force me to do things. But Don never wanted to have sex, much less take control of me...

I would see Jon delivering the mail from time to time in the office building and soon realized that many of the girls in the office had the hots for Jon. They would look at his butt after he past them in the hall and whisper to each other. But Jon didn't seem too interested in any of them. Occassionally he would stop by and deliver my mail and we would chat about things. I was really glad that he was working for us.

The next week, I got an email from someone that I didn't recognize. It was to my personnal email account that only a handful of people knew. It said "You are so sexy and pretty. It is a shame to see such a wonderful body goto waste. I bet your husband isn't taking care of you the way you need to be taking care of. Think about this and I will be in touch with you soon..." I tried to see who the sender was, but whoever sent it blocked that part out. I was excited and nervous, how would anyone know about my private life. Despite what people may think, I never slept my way to the position that I currently held. I worked hard for it.

I didn't think much more about the email and didn't tell anyone about it. Not even Betsy who I share everything with. And then a week after I got the first one, I got another one. It said "You probally thought that I had forgotten you, well I haven't. I know how bad you want to have sex, I bet your pussy is dripping wondering who this is and if you will ever get to meet me. Or how about how big my cock is. Well if you are a good little girl and do as I say you will find out soon..." I was in shock. I didn't know who was doing this, but the joke was over. I didn't think that it was funny. But on the same note, I didn't know who was sending this.

The next morning, I got another email. It said "If you want to know who I am and want to experience what a man can do for you then you will do as I say. You will be recieving a box tomorrow at work. You will need to follow the instructions inside it. Before you can do that, you will need to make sure that your pussy is shaved bald. I don't want to see any hair." I still didn't know who this person was, but I knew that they had definately got me curious.

The following morning, I told Betsy that I wouldn't be able to work out with her. I told her that I had a meeting that I needed to prepare for. I turned on the water to take a nice hot shower. I usually kept my pussy pretty trimmed, but I had never shaved it bald. My hand was trembling as I shaved around my clit, it felt so wonderful that I played with my pussy for a few minutes before I decided that I needed to get going. I left the house without ever saying goodbye to Don. I usually don't get to the office until 8 a.m., but today I was so excited that I left 30 minutes early.

Today I dressed in my usual knee lengeth dress with a nice blouse and a jacket. I was wearing pantyhose and my usual 2" heels. When I unlocked the door to my office, I noticed that there was a box on my desk. The box was about 2' wide by 1' tall and was sealed with brown packing tape. It didn't have any return address on it, just my name and address. I began opening the box. When I got it opened, their was an envelope on the top. I opened it and it read "Inside you will find a better outfit for you to wear. I expect you to go and change when you finish reading this. You will remove your clothing that you are currently wearing and put it in the box. You will then sit the box outside your office door. If you chose not to do this then you will never know who I am. If you chose to carry on, I will be in touch with you soon via email..." With that I put the card down and finished unwrapping the contents inside. Inside was a gray colored short skirt with a matching jacket with silver buttons. Underneath that was a black lace garter belt and a pair of black seamed stockings. In the bottom of the box was a pair of black 4" heels. Their wasn't any panties and their was no blouse in the box.

I did as the note said and changed my clothes. I noticed two things as soon as I finished buttoning the jacket. One was that the skirt was not knee length, it was about 4" above my knee. A bit too risky and sexy for my peers to see. Second was that the jacket had a plunging neck line that really showed my cleavage. It was tight and really pulled my breasts together. I slid my feet into the heels and tried walking in them in my office. It is amazing what an extra two inches can do for your stability. I finally put my old clothes in the box and put them outside my office door and sat down at my computer.

Sure enough I had an email. It read "You have done very good so far and I am pleased. I want you to sit down now and play with your pussy. How does it feel now that you have a bald pussy? Do you enjoy the feeling of rubbing it? For the rest of the day you will find it hard to focus on work. You will want to play with your pussy. You will try to leave, but you don't dare walk out of your office dressed like this for your peers to see you. At the end of the day, I will have another surprise for you... enjoy playing with your pussy..."

Well whoever this was sure knew what they were talking about. All day long I played with my pussy. I fingered myself and rubbed my clit. It felt soooo good to have a smooth pussy. I didn't get any work done. Then at 5:00 p.m. my secretary knocked on the door and brought in a long coat. She said "I saw that you left this outside the door, you will need it today since it has gotten cold outside". I thanked her, not leaving my chair and looked at my computer. There was an email from the mystery person. It read "I thought that I would spare you some decentcy by allowing you to wear this home. When you get home there will be another package at your house. Inside will contain the contents of what you are going to wear to work tomorrow. This time you might not be so lucky as to get a coat."

When I got home, I noticed their was no package on my door step like the email said. I was nervous that someone may have found it and opened it. Then I got a knock on the door. It was a delivery man holding another large box. As I signed for it I noticed that he was looking at my dress and how my jacket was framing my breast tightly. I thanked him and quickly shut the door. I took the box and ran upstairs to my room. Don would be home soon and I wanted to see what was inside before he came home.

I opened the box to find another note. "You are doing well so far. Keep this up and you will soon find much pleasure. Inside will be the outfit you will wear tomorrow. If it isn't in the box, you don't wear it..." I opened it to find a short black skirt and a matching double breasted jacket. I held the skirt up to the one that I was wearing and noticed that it was about 2" shorter. This skirt was too short for me to wear to work. It would be something that I would only wear in the privacy of my home for Don. I didn't really pay much attention to the jacket. Further in the box was another pair of black seamed stockings and a black waist cincher with garter belts attached. At the bottom was a pair of black 5" stiletto heels. I was just getting the hang of walking in the 4" heels and now whoever this was added another inch. I noticed that whoever sent this to me didn't include any panties or a bra. I did not want to wear this to work tomorrow. What if someone saw me looking like this, the rumors would start immediately.

The next morning, I got up early and shaved my pussy smooth again and began getting dressed. I was being quiet so that I wouldn't wake up Don. I put on the waist cincher and attached my stockings to the garter belts and slid my feet in the heels. I was surprised at how well I was able to walk in them. I then put the skirt on. It was extremely tight. I looked in the mirror and noticed that you could see the garter belt straps outlined in the skirt. I then put the jacket on. As I was buttoning it, I noticed that I couldn't quite get the buttons to reach. I would have to tighten the waist cincher even tighter. It took a few tries with me sucking in my breath in order for me to get the waist cincher tight enough to button the jacket. I turned to look in the my full lengeth mirror and noticed that the two buttons just below my breasts was causing my breasts to push up and out. And that the skirt just barely covered my stockings. I didn't have a choice, I was curious to meet this secret person. I grabbed my long coat and left.

As I was locking the front door, Betsy came walking up. She had been out jogging and looked great in a tight sports bra that barely contained her nipples through the sweaty fabric. I was trying to avoid her and tried to grab my coat to close it, but instead this only caused it to open revealing what I was wearing. Betsy's eyes got wide and she said "Wow, look at how sexy you look. What is the occassion?". I didn't know what to tell her, so I said "I just thought that I would dress a little sexy to maybe spark Don's interest in me again". Betsy laughed and said "Jill, Don isn't even awake yet. Are you having an affair? I am your best friend and you have been acting strange the past two days." I ended up telling her about the emails and how excited I was about not knowing who it was. I told her that I hoped that it was Don trying to play games with me and make me horny as hell. Betsy laughed and said "well keep me posted". and with that she went home and I went to the office.

As I entered my office I got a call from my secretary telling me that she would be out sick today. As I sat down at my desk I noticed that something was under it. I looked down and gasped, under my desk was a dildo facing me. It was attached to a metal T shape pole that someone had bolted to each side of my desk. I decided that I should check my email to see what was going on and sure enough their was a message from him.

It read "By now you have found your new toy. At noon today I will be by for you to get your first taste of being my slave, but you will need to follow my instructions first. I put a blindfold in the top drawer of your desk and some rope. I want you to put the blindfold on and then tie your wrists to the arms of your chair before noon. Then I will come in and we will begin your training. Until that time, you will fuck yourself with the dildo that is under your desk."

By now I was extremely wet with anticipation of meeting this stranger. I slowly rolled my chair up to the dildo. It was quite long about 7" and about 2" thick, I was so horny that I took my hand and ran it along my slit and slide right onto the dildo. It felt so good to roll back and forth on this dildo with my chair. Now I know why he didn't want me to wear any panties. Throughout the morning I had countless orgasims.

Then at 11:40 I put the blindfold on and began tieing my arms to the chair. I wanted to make sure that I was ready in case I had problems tieing my wrists to the chair. After I had tied myself to the chair I impaled myself on the dildo and began rocking back and forth on it. It felt so good that I must not have heard the door open. But between my moans I did hear it close and then I heard the lock click. I couldn't see who was there, I soon felt someone unbuttoning my jacket and then I felt a gloved hand tweaking my nipples. "Ohhhhhhhhh" I moaned with pleasure. The whole time this person didn't make a sound. Then I felt them pull the chair back and turn it to the left. I then felt a tongue on my clit. Whoever this was could sure lick pussy. I was on the edge of cumming when the licking stopped.

Then I heard a different noise, a zipper and then some clanking. I then felt the gloved hands pick my legs up and pull my ass to the edge of my chair. Then without any notice I felt a hard cock enter my pussy. It felt thicker than the dildo and had a nice head that I could feel as he slowly fucked me. I was going crazy and moaning. While I was being fucked, I felt the gloved hand back on my nipples and could feel them harden under his touch. I started cumming and beganing begging "please fuck me, please fuck my pussy, I'll do whatever you want, just keep fucking meeeee... OOOHHHHH YYYEEESSSSS I'MMMMM CUUUMMMMMMINNNNNGGGGG!!!!" When I was finished cumming, I felt the cock leave my pussy. Then I felt it against my lips. I opened my mouth and started sucking my juices off this wonderful cock. Then the cock was pulled from my mouth.

A hand ran up to the blindfold that was keeping me from seeing my new lover and then they pulled it off. To my complete shock it Betsy was standing in front of me with a strap on dildo attached to her waist. My eyes wear huge with shock and she put her gloved hand to her lips and said "shhhhhhhh, I know that you needed that". "So you are the one that has been sending me all of those emails and making me dress like a slut?" I said. "No, when I saw you this morning dressed all sexy, I knew that you were up to something and I figured that I would stop by to take you to lunch. When your secretary wasn't at her desk, I opened the door and saw you all tied up and blindfolded. I knew that now was my chance to give you want you needed." I then asked her how she managed to get into my office and install the dildo?" She looked at me and said "That wasn't me either".

"Oh God Betsy what am I gonna do, I was suppose to meet this mystery person at noon today and that is who I was waiting for tied up and blindfolded. Because you showed up I bet they didn't come in." I barked. "Relax, I am sure that whoever it is will be in contact with you soon, I didn't mean to interrupt anything... Jill, have you thought about what you would do if it isn't Don?" "Betsy, I am sure that it is Don, how else would he know my personal email address and no what size clothes I wear." I replied. I really had not thought about what if it was somebody else. I then told Betsy that I had some work to do and that I would talk to hear tonight when I got home. With that she left and went to my computer to check my email. No new messages. Ummm that was strange. I checked back after 10 minutes and saw a new message from my mystery person. It read "I see that our meeting was interrupted. Maybe if you are lucky you will get another chance. I will send you a package with something to wear later..."

Chapter 2

It was almost 5 p.m. and I was fucking myself with the dildo under my desk when Jon knocked on my door and brought in a box. The look on my face was probally one of shock and pleasure and I was hoping that Jon wouldn't know what I was doing under my desk. Jon asked me if I was ok and I told him yes, that I was tired and just about to go home. He then placed both hands on my desk and looked me straight in the eyes and said "are you enjoying that dildo underneath your desk?" "Jon, that is no way to talk to me, I am your boss and your mom and I are best friends!" I shouted. Jon got this cocky grin on his face and said "you may be my boss in the eyes of your company, but you are so horny right now, you will do whatever I tell you to do. I know how bad you need someone like me to take over your life and now that I live and work near you, that is exactly what I am going to do."

With that he came around the side of my desk and said "Unzip my pants and suck my cock". I didn't want to because he was my best friend's son and I had never been unfaithful to Don, but he was also right he was just what I wanted in my a life, someone to control me, to make me do slutty things, I needed a master. I unzipped his pants and pulled out his semi erect cock. It was extremely thick and in it's semi erect state it was already 7" long. I slowly started licking his balls and running my tongue up and down his hardening cock. I then started to go down on his cock. I had a hard time sucking him as he was bigger than anything that I had ever seen before. When he was fully erect, he was at 10", nearly twice as big as Don's small little 6" penis and it seemed like the more I sucked the thicker he became. I sucked Jon for all I was worth and was really surprised at how long he was holding out. It must have been 20 minutes before I felt his cock start to twitch and then I felt a large blast of cum hit the back of my throat causing me to gag. Jon pulled his cock out of my mouth and blasted my face and all down my jacket. I had never seen anyone cum so much.

Jon then said "Tonight, you will goto dinner with me and then come back to my apartment. You will need to call Don and let him know that you will be working late and not to expect you until later". I just nodded in agreement and called Don to let him know that I wouldn't be home until late and he seemed ok with that. He told me to open the box and get dressed for our date. As I opened the box I still couldn't believe what I was doing and how I was behaving. I looked into the box and saw a short zebra striped skirt with a black sleeveless shirt that had a deep plunging neckline.

Jon then told me to stand up. I did and he helped me out of my jacket and then he pulled my skirt down. He handed me the zebra striped mini and I pulled it on. It was even shorter than the skirt I had been wearing all day. I could see the tops of my stockings and that was with me standing. He then helped me put on the top. It too was extremely tight and gave a nice view of my cleavage. I cleaned the cum off of my face and Jon said "Lets go". But I couldn't walk out of the office looking like this, what if someone saw me and what if they saw me looking like this and leaving with Jon, what would they say then. I begged Jon to let me at least wear my long coat. He agreed and we left.

As we road the elevator down to the parking garage, Jon stood in front of me and slid his hand under my skirt and was playing with my pussy. It wasn't so bad until the elevator stopped and more people filed in. Still Jon never missed a beat, I was on the verge of cumming when we reached the garage. I followed him to his car and he opened the door and let me in. As Jon let the car warm up, he told me "I was nice enough to let you have a coat to wear in the office, however, you won't be able to wear it anymore tonight. Jon helped me out of the coat and we left toward the resturant.