Totally Tiffany free porn video

Totally Tiffany I I don't remember when it started. It seems as if my earliest memories are of wanting to be a girl. I grew up in a family that was typical of middle class America, mom and dad both worked to support us. I had an older brother and two older sisters. Being the baby of the family had both its advantages and its disadvantages. I learned to live with it. My brother Jake was five years older than me and was my arch nemesis. We fought more often than not, and I was the one who walked away with the bruises. My sisters Beth and Anna were one year and two years older than me and we were always much closer than Jake and I were, therefore I spent far more time with them while growing up. I do remember as early as first grade sneaking into my sisters' room and trying on their clothes when nobody was paying attention. It gave me such a thrill. Throughout my school years I continued this routine, even making up reasons to stay home when the whole family was heading on an outing. By the time I was in high school I was getting pretty good with make up and could pass for a girl as long as I stayed away from any direct scrutiny. My college years gave me freedom to explore, but I forever felt that I was going to get discovered. I acquired a decent wardrobe but stayed in my apartment out of fear of getting caught. After finishing college and law school, I got married to a girl I had met in college, and started working for a major law firm in Chicago. I assumed that my days of dressing were over and I tossed out my entire collection of clothes. Barbara and I had a wonderful marriage and started our life together with optimism and promise for the future. She had graduated with degrees in Political Science and International Affairs. She took a job as an advisor to a political action committee and frequently traveled. We bought a house, new cars and took vacations to exotic locations. In general life could not have been better. It was during one of Barbara's trips over seas that the old urge hit me. She had been gone for a week and was not due back for another two weeks. It was the longest that we had been apart since we were married. I started getting horny, and without her there to take care of my needs, one thing led to another and I soon found myself exploring her closets. That first afternoon, it started with a quick hour of dress up. Bra and panties, pantyhose and a dress, shoes, jewelry and makeup, and I was ready for some quick relief. I changed clothes as fast as I could, being careful to put everything back where it belonged. For the rest of the day I sat around feeling guilty, but when bedtime arrived, I headed right back to Barbara's dresser for a nightgown to wear. At 5' 10" tall and 155 pounds my build was rather slim. Barbara was 5' 7" and 126 pounds. She wore a size nine and although some of her clothes were a little tight, I could fit into almost everything she had. Since my feet are small, my size 7 men's fit into most of her 8 ? women's with just a little squeezing. It didn't take long for me to start looking forward to her trips out of town. Barbara and I both enjoyed success in our careers. For me, this meant promotions and a much larger salary. For Barbara, this meant a lot more travel and a little more salary. I was on the fast track with my firm and planned on being the youngest partner in the history of the firm. My long hours at the office were quite often offset by evenings and weekends exploring my feminine side. Over time, I became more confidant in my look when enfemme. I had purchased an expensive blond wig and felt that this was the final touch needed to make me totally passable. With my newfound confidence I started heading out into the world on a regular basis. At first, it was late night drives through town or a quick walk in the park. Later it became stops at the mall and trips to bars. I was very certain that I was good enough to never get recognized. This was my first mistake. At work, things continued to go well. The only problem that I had was when I let my ego get in the way. This seemed to happen more often than not with some of the female attorneys. I worked hard and so did they but I took every opportunity I could to put them down. It was that much less competition for the promotions. This turned out to be my second mistake. The one female attorney that did earn my respect was Stephanie Wilson. She was very bright, very good looking and for some reason very approachable. Most of the female attorneys tended to be quiet and within themselves. Stephanie was just the opposite. She was outgoing, easy to talk to and very, very competitive. She was not married, and I started having an affair with her. This was my third and biggest mistake. Stephanie and I had been seeing each other for several months and I now had another reason to look forward to Barbara's frequent trips. After our dates, we generally ended up at Stephanie's place for our sexual activity. She lived by herself and this gave us a higher degree of safety. I was not concerned about Barbara catching us, but you just never knew about nosey neighbors. Recently, Stephanie had started talking about a long-term relationship. She had even gone so far as to suggest a divorce so that we could get married. I tried to talk sense into her but she would have no part of it. She tried everything she knew to convince me, but in the end, I held firm. As part of Stephanie's plans to convince me to divorce Barbara, she started planning long weekends at her place whenever Barbara was out of town. This resulted in several things happening. First of all, since we were expected to work at least two Saturdays a month, I needed to have extra clothes at her apartment. Soon, I had six or seven different sets of clothes hanging in one of her closets to use after a Friday night spent there. Second, since my clothes were hanging in one of her closets, I started having chances to explore her closet a little closer. Third, since our monthly schedule was never fixed, I ended up with several Saturdays at Stephanie's apartment alone. This was a dangerous situation that ultimately blew up on me. Stephanie had great taste in clothing, and she had a great body to show it off on. She was 5' 10" tall just like me and weighed about 120 pounds. She wore a size 7 dress and a size 9 shoe. I was soon to discover that while most of her clothes either would not fit, or were very tight; there were enough that would fit to keep me happy. And best of all, her shoes fit perfectly. I even found a long brown wig in the back of her closet. I was in heaven, a whole new wardrobe to play with. It was a Saturday in March when it finally happened. Stephanie was scheduled for a marathon session with an attorney from out of town. They would start at 10:00AM and probably work through dinner. She left early before I was out of bed, "You don't need to stay around and wait on me. When I get done I'll give you a call and maybe we can meet somewhere for a drink." That was it, my free ticket to a full day of playing dress up. The weather was terrible and I had no other plans so it was a perfect day to stay inside and play. Stephanie was barely out the door when I got out of bed and headed for the shower. I was fortunate that I did not have much for body hair so shaving off what was there would hardly be noticeable. I really wanted today to be special. When I dried off, I used some of Stephanie's skin lotion and bath powder. I felt soft and smooth and wonderful. After drying my hair I headed to her closets to pick out my outfit. I already had a good idea of what I wanted to wear, but I wanted to do some browsing anyway. After spending some time checking out several different outfits, I settled on the one that I had in mind from the start. It was a dress that I had seen Stephanie wear several times to the office. It was both very professional and very sexy. It was red silk with a hemline that hit at mid thigh, perhaps a bit short but still acceptable in today's business world. The waistline was fitted and the skirt flared slightly from there. The top of the dress was cut low enough to be suggestive but not so as to be improper. With the dress selected, I went about choosing the rest of the outfit. The lingerie was white in soft nylon and lace. The bra was under wired and padded which helped to give me a modest bust line. I selected pantyhose in a suntan shade that helped to improve the look of my legs and then added a panty girdle to hold everything in place. A white slip helped to give me a smooth look in the dress. The shoes I chose were red pumps with a four-inch heel and ankle strap. I sat at Stephanie's dressing table for almost an hour trying to get the makeup just right. When I was pleased, I selected gold jewelry and pulled the wig into place. The wig was pre-styled and fell to shoulder length, so all that was necessary was to brush it a bit. I used some of her Shalimar perfume and was ready for anything. Well, at least I thought that I was. I walked around the apartment for a while and even tried to watch a little TV, but I wanted more. Finally I decided that looking this good, that I needed to get out. I grabbed one of Stephanie's purses, threw a little cash into it and headed to my car. I drove across town to the mall, one of my favorite places to be seen, with out being seen. I spent some time walking around doing a little window-shopping and even got some lunch in the food court. Finally around 3:00 I figured that I better be headed back. I was only a mile from the mall when disaster struck. A flat tire! Now I had changed flat tires before, but never when I was dressed like this. I pulled over to the side of the road and settled down my nerves. I was just preparing to get out and change the tire when the situation turned worse. There in my rear view mirror was a police car, red lights on and the officer getting out of the car. "Can I help you miss? It looks like you are having a bit of trouble," he said being ever so gracious. Well, he did call a towing service and they came out and changed the tire, so I survived that much. After paying the mechanic, I was about to leave when it got worse again. It was the police officer in his cheerful voice, "Miss, I am going to have to see your license. I need to fill out an incident report and account for my time. I promise, it won't take but a minute." I didn't know what to do. I stalled for time digging in the purse like I was looking for the license. Finally I looked up with as sad of eyes as I could manage, "I guess that I don't have it with me. I am sorry, but I changed purses this morning and I must have left it in the other purse." I smiled and tried to look helpless. It didn't work. The officer returned my smile. "I am sorry to have to tell you this, but I will need to give you a warning ticket for not carrying your license with you. You will need to take your license to the police department downtown within ten days to clear the ticket. If you don't, there is a $150 fine to pay. Now, could I have you name and registration for the car?" Now, my mind froze again. My name? The registration? What was I going to do? I looked at the officer and tried to smile, but that got me nowhere. My brain was racing 100 miles per hour. I couldn't give him my name dressed as I was, but what else could I do? The other problem was that the registration was in my wife's name since I was driving her car while mine was in the shop. Finally, that was the solution I arrived at, I reached into the console and pulled out the registration and handed it to the officer, "Here you are officer, and there is my name right on the card, Barbara Mears. I really am sorry for not having my license with me. I will be sure to get down to the station right away getting this taken care of." Finally, the officer warmed up just a bit. "OK Miss Mears, since I see that you have you registration and insurance requirements covered, I am going to cut you a break this time. I am going to run your plate for ID, and as long as it comes back without issue, I'll let you slide just this once." I sat there for another ten minutes while the officer ran the plate and came back to tell me that everything would be OK. He gave me another stern warning about carrying my license with me, and then gave me a smile and sent me on my way. I took a deep breath and pulled away. I drove carefully back to Stephanie's apartment just to make sure that I didn't risk another incident. By the time I got back to Stephanie's, it was after 5:00. My heart was racing knowing that my time was growing short if I was going to get changed and have everything back where it belonged before she got home. I had to park near the opposite end of the lot in order to find a place and hurried down the sidewalk not paying attention to the surroundings. If I had been just a little more observant, I would have seen Stephanie's car parked just across the aisle. I entered the main hall of the apartment building and made my way down the hall to Stephanie's apartment as I turned the key in the lock, my heart started to settle down. I entered the living room turned on the light and took three steps across the room when I met Stephanie coming out of the bedroom. We both stopped where we were. The look on her face went from shock, to confusion, to recognition. As I watched, I knew that I was screwed. No matter what, my life had just changed, and it was not going to be for the better. Stephanie smiled wickedly at me. "Well, well, it looks like my Thomas has been keeping a secret from me. Or should I say Thomasina? Well don't just stand there looking like an embarrassed little girl, come tell me all about this. I just can't wait to hear this story." From that moment on she owned me, and she knew it. We sat and talked for hours. I wanted to change but she would not let me. I told her everything there was to tell; from the time I was six and first pulled on my sister's panties, to the traffic stop this afternoon. She was totally enraptured with my story. She made me stop for a while and she got her digital camera. She had me pose in several positions and took a whole series of pictures. By the time I was done, I was in tears. I just wanted to change clothes and have it all be over with, and I told her that. She smiled and told me to dry my tears, "This is far from being over my little one, as a matter of fact; I believe that this is just beginning." I sat there grimacing as Stephanie laid down the new rules for our relationship. "First of all, I think that we shall find all sorts of ways to explore this new side of you. Secondly, you will dress when I tell you to, how I tell you to and act exactly as I tell you to or I will find all sorts of clever ways to provide punishment. Third, I think that our relationship overall should take on a more significant role in your life. I realize that you might be challenged to make up new excuses for your wife, but I would bet that she has no idea about this little game of yours. Last, I may choose at any time to provide you with challenges that you may find embarrassing, demeaning, unappetizing or otherwise distasteful. You will however in all such cases reply, respond and react exactly as I require you to do. In the event that you choose not to do so, just remember the pictures that I just took. I will be placing these in a very special location on the Internet where they can be made instantly available to anyone, including your precious little wife and the senior partners of the firm. Now then my dear little one, do we have an understanding?" I looked up at her with tears in my eyes. "Yes, we have an understanding." She looked at me scornfully. "I am sorry, but to whom were you addressing that comment. Was that to just anyone, or was that to your loving Mistress?" I looked up again, and then cast my eyes downwards. "I am sorry Mistress, I fully understand the agreement that we have reached." Now she smiled. "Well that was easy wasn't it? Now, I think that a little celebration is called for. Why don't you run out and pick up a good bottle of wine and some food to go with it. While you are gone I will bathe and change clothes. When you return you can pamper me for the rest of the evening. Then tomorrow, I believe that you would like to take me to dinner, wouldn't you dear? And you do know that my favorite place in the whole world to dine out is the new five star French restaurant downtown, don't you? I know that it is a bit on the expensive side, but I am sure that you want to make a very good impression on me, don't you my love? Now then, why don't you dry your tears, make the reservation and run and get the food and wine. Then come into the bedroom and we will pick you out an appropriate outfit and try to get you looking presentable." I had no choice. She had enough of a story along with pictures to ruin me. I found the number for the French restaurant and made the reservations. Then I looked in the mirror and repaired my makeup from what I had in the purse. I headed out to a gourmet food shop that I knew and pick up a light dinner for two. It contained a light salad, various cheeses with crackers and a fruit plate. I found an excellent bottle of Chardonnay to go with it. Just in case it would help to sooth her nerves, I picked up a second bottle of the wine. On the way back to the apartment I found a little flower shop that was open late and purchased some roses. Anything that I could do at this point that might help to improve her attitude I would try. When I made it back to the apartment, I laid out the dinner and put the wine to chill. Slowly, I made my way to the bedroom where Stephanie waited. When I entered, she was sitting at her dressing table. She was wearing a long white nightgown and matching robe. I looked at her meekly and stopped in the middle of the room waiting for instructions. They were soon forthcoming. "Strip!" she barked. "Then get over here where I can see you." I started to undress, and she turned to watch. Soon I was standing there wearing nothing but the pair of white panties. She got up and walked across the room checking me out. As she moved around behind me I suddenly felt a firm slap on my ass. "It is obvious to me, that there is much work to be done here. When I give you a simple order, and you cannot even complete it satisfactorily, it shows me that there is a great need for training. Now, get those panties off while I decide what your punishment should be!" With that, she slapped me firmly on the ass again. I dropped the panties and stood quietly. After several minutes, she ordered me into the shower, telling me to return when I was properly cleaned. When I returned, she was again seated at the dressing table. On the bed, she had laid what was to be my outfit for the evening. There was a red bustier that laced up the back and a pair of red stockings that would attach to the garters. There was also a matching thong panty. A pair of red slip on shoes, also in red, with four-inch heels set on the floor. Smiling, Stephanie headed for the door. "When you are dressed, make sure to do your make up and your hair. I realize that it is not very long, so you will have to be creative. You have seen girls with short hair before. Just try to remember how they did their hair. I am sure, that you will come up with something appropriate. Remember, you will be judged on your final appearance so do a good job. Make sure that you hurry, I will be enjoying the wine and waiting for you to serve me dinner." I emerged from the bedroom, ? an hour later. Stephanie was sitting on the sofa with a glass of wine, looking through a fashion magazine. "Oh my, don't you look precious? You know, with a little work, I think that we can make you into quite the presentable little lady. Now, pour me some more wine, and serve me my dinner. Then when I am satisfied, you can fix yourself some also." When I had served her, and obtained her approval, I fixed my own dinner. When I came into the room with my plate of food and glass of wine she stopped me. "That's totally wrong for a young lady like you. You will get fat and lazy if you eat that much. Now I want you to go back in the kitchen and remove half of everything from your plate. Then, you may sit with me to eat." On my second trip into the room, she inspected my plate and approved. As I moved towards the sofa, she motioned to the floor. "At my feet, you will kneel there as you eat. That is the appropriate place for a young slave girl!" After dinner, I cleaned the dishes and put them away. Stephanie watched my work from the living room where she had consumed more of the wine. I hoped that it was having the desired affect, but I was growing doubtful. When I was done, she motioned me to the bedroom. "We still have the matter of punishment to address before bedtime." Once in the bedroom, Stephanie removed her robe and climbed onto her bed. "You know slave girl, I would be in a much better mood, and probably much more lenient, if you were to find some way to help me relax. Why don't you crawl up here along side of me and see if you can put your tongue to any good use." An hour later she was coming down from her third orgasm when she decided it was enough. "You have done well. You almost, but not quite made up for your earlier indiscretions. Therefore, you must still be punished. Now, I want you to stand at the foot of my bed and wait, while I get things ready." When she returned to the room she was carrying a number of things. She stayed behind me so that I could not tell what they were. She ordered me to the bathroom to ?take care of any business that I required', and then back to the foot of the bed. Her bed was a metal-framed canopy style. When she had me bend over the footboard, I began to get nervous. Looking back, I saw her holding a large enema bag along with several types of fittings. "I believe that a slave must be clean both inside and out. Therefore, I will need to show you how to take care of the internal cleaning. Now, hold still while I get you ready." Stephanie hung the enema bottle from the canopy frame and got busy with the hoses and fittings. Suddenly, I felt her smear something cold on my ass. This was soon followed by her finger moving around and finally into my tight hole. Before I knew what happened, a plastics tip replaced her finger and it was pushed firmly inside of me. I squirmed and squealed, earning a sharp slap on the ass. I knew that I had better hold still. When I settled down, I heard a faint noise of air being pumped. As I felt it I realized what it was. Stephanie was using a small squeeze ball to pump up what ever it was that she had placed in my ass. "We just want to make sure that everything stays in place." She quit pumping and removed the ball. When she gave a taught pull on the hose that was now attached to me, I knew that it would not come loose. She connected the loose end of a hose to a fitting that was on the bag hanging over my head. She opened a valve and let the solution fill the hose replacing the air in it. She then closed the valve. She now reconnected the second end of the hose to the fitting in my backside. Before I even had time to think about it, she opened the valve and the force of gravity started the fluid moving again. I felt it inside of me almost immediately. It was cool and created a slight burning inside of me. "Don't worry my pet. You will soon get used to this feeling. I believe in regular thorough cleanings." It took only minutes for the bag to empty and for me to feel full. When it was done, Stephanie waited only a minute before she shut off the valve. She disconnected the hose at the bag and laid it up over my back. She had me stand upright and reach over my shoulder to grasp the hose. "Now, hold it firmly. As long as you keep it high, the solution cannot flow back out." She had me walk to the bathroom and then lower the hose into the toilet. The solution flowed out in a steady stream, propelled by the pressure of my contracting intestines. When I was done purging, I moved back into the bedroom. Much to my disappointment, Stephanie had hung a second bottle from the canopy frame. This bottle was much larger and the solution looked much more ominous. It was pink and looked thick and heavy. This time as Stephanie moved me into place, she tied my ankles to the rail on the footboard. She then pulled my hands over my head and tied them tightly to the canopy frame near the bottle. She stepped behind me, hooked the bottle to the hose and turned on the valve. Just as I thought, the fluid moved very slowly down through the hose towards its final destination. "This will be fun. With this solution, and the medium sized bottle, it should take 40 or 50 minutes to fill you up completely. When it is done, you will feel like you swallowed a pumpkin. That's when the real fun begins." She lay across the bed and watched. As the pink fluid found its way inside of me, I knew that this was going to be no fun at all. It had the feel of something solid, but slowly, bit-by-bit, it kept growing. It also had a secondary effect; it created an itch deep inside of me. The more it filled, the more I itched. Soon, I was wiggling my butt like a sex crazed schoolgirl trying to get some relief. Stephanie looked up at me and smiled. "Getting to be fun isn't it. Now let's add something more. She moved to the dresser and picked up two little shiny balls each about ? of an inch in diameter. As she approached me, I saw that they had small clamps attached to them. She quickly clamped them onto my nipples and gave them a little tug. As if the force of the clamps weren't enough, the balls bounced and swayed. "They are hollow, and filled with Mercury. The way that you are wiggling your ass, it is sure to keep these babies moving for you." I opened my mouth and started to protest, and she slapped me. "Slaves must always be quiet unless spoken too. Now open wide." As I did, she picked up a red rubber ball and pushed it into my mouth until my teeth clamped it. I tried to use my tongue to push it out but could not. "Now let's see just how well it works." With that, Stephanie reached out and pulled hard on the nipple clamps setting them bobbing to and fro. I screamed, at least I thought I did. All that came out from behind the ball was a long, low squeal. I hung there for the better part of an hour before Stephanie was satisfied that the enema bottle was empty. Finally, she stepped behind me and started to disconnect things. This is when I realized that there was another valve at the receiving end of the enema system. This time, she closed this valve securely maintaining the full load of pink fluid inside of me. By the time that she untied me, I was about to go out of my mind. The constant itch that kept me wiggling had also kept the nipple clamps moving. The pain was incredible, but at the same time, I now had an erection. "See my dear. Even the punishment comes with some rewards. Now I want you to kneel at the foot of the bed, and you can go ahead and relieve yourself." I didn't have to ask what she meant. I kneeled there, took a grip on my manhood and started to massage it. That was when I found out about her next surprise. "Oh, did I forget to tell you? That wonderful pink medicine not only creates that itch inside, but it has the added benefit of reducing your sensitivity to touch. It will probably take you a while before you achieve a climax, but you need to keep working at it. When you do, then we will see about getting you drained out and put to bed." Never in my life had it been so hard to achieve a climax. I worked at it every way I knew how. Stephanie just sat back and watched. Little by little, the feeling would build, and then my arms would be so tired that I would slow down and loose ground. At long last, she took pity on me. She moved behind me and reached around my waist grasping my member and helping me to finish. When I finally came, I thought that I was going to collapse. As I knelt there, Stephanie caught every drop in a small cup. When I was done, she reached up and pulled the red ball from my mouth replacing it with the cup. She poured it all into my mouth while telling me to swallow, and not to waste a drop. I moved to the bathroom and Stephanie removed the device from my ass. She had me sit on the toilet. The pink fluid came out almost as slowly as it went in. While I sat there, she removed the clamps from my nipples. This caused such a wave of pain that I almost passed out. She told me to sit until I was sure that I was empty and then clean up and come to bed. Almost an hour later, I made my way to her bed. When she saw me approach, she handed me a blanket and pointed to the floor at the foot of the bed. "That is the proper place for a slave girl to sleep." I threw the blanket down and curled up there falling to sleep quickly. I was tired and sore, and worse yet, I knew that there was more to come tomorrow, and the next day. Sunday started up right where Saturday night had left off. I had to fix a bath for Stephanie and help her to get dressed. I fixed breakfast and served her while still dressed in the red outfit from the night before. When she was done, she headed out to visit with friends, I was left there to clean up the apartment, take a shower and make myself presentable. When she returned, we would decide what to wear for our diner date. I spent the afternoon making the apartment look as good as ever. I cleaned and dusted, vacuumed and polished. The kitchen was spotless and the bedroom was put back together after last night's ordeal. I picked up the enema bottle and other pieces and laid them in the bathroom. When everything was done, I took a shower and picked out something to wear. I kept it simple, yet picked something that I knew Stephanie would approve of in her current state of mind. I chose a black skirt and white blouse that were both simple and subtly sexy. I added black panty hose and heels. I used her wig again and added simple jewelry and soft make up. When I was done, I thought that I looked quite presentable. I sat in the living room waiting for Stephanie's return. Minute by minute, I thought about how she was about to turn my life into a living hell. The problem that I had was that I could see no way to stop her. With the pictures, and the story that she could tell, I would lose my wife, my job, and my whole life style. I would just have to play along until the right moment. Life always presented opportunities to get even; I just had to be ready when it happened. When Stephanie returned, I had made the mistake of falling asleep on the sofa. She was irate. "This calls for another punishment! Now stand up here and let me look at you. We will take account of your appearance and the job you did cleaning the apartment. I will assign you demerits, and you will keep count. Do you understand?" I looked at her trough still sleepy eyes, "Yes mistress, I understand. You assign demerits and I keep count." "Good, then let us begin. Your clothes are wrinkled, that will cost you five demerits. Your hair and makeup are fair, that will only cost you two demerits. Your fingernails look terrible. Couldn't you at least have made an effort? Two more demerits." After the personal inspection, she proceeded to inspect the house. The toilets were not cleaned, five more demerits. The trash had not been carried out, two more demerits. And finally, the towels in the bathroom were not folded properly, another demerit. The total came to seventeen demerits. We sat in the living room while Stephanie decided on an appropriate punishment. I was genuinely worried; I did not want a repeat of last night. When she was done thinking about it, she ordered me in to the bedroom. I stood at the end of the bed as she instructed. She had me drop my panties and pantyhose to my ankle and lift my skirt to my waist. She then bent me over the footboard and told me not to move. She left the room for a minute and when she returned she showed me what she had gone for. It was an oak cutting board, one inch thick, eight inches in diameter with a long stout handle. It was part of a cheese cutting set, but would serve well as a paddle. "I want you to count out each swat for me in a nice loud voice. There is nothing like a good paddling to make a girl remember to try harder next time." Stephanie used all of her strength to swing the paddle. The first swat brought tears to my eyes and by the sixth one I was crying freely and pleading for her to stop. It was after the tenth swat had landed that she quit. My knees were buckling and I could hardly stand. She stepped back and surveyed her work. She rubbed her hand on my butt feeling the welts that she had left. "My but you are red on the cheeks, and very warm I might add. Now, get your self together, we have some shopping to do." I cleaned up as best as I could and Stephanie said that I looked good enough for now. We took her car and she drove out towards the mall. "We need to get you some things of your own. I don't think that it's fair that you should get to borrow my things. Most of them don't fit you properly and I don't want them ruined." I tried to argue with her but I knew that it would do me no good. When we got to the mall, the first place we went to was a small dress shop. All of the clothes were very pretty, and very expensive. We were looking at a rack with spring and summer dresses when a clerk walked up and asked if she could help. The girl was about eighteen years old and looked like a high school cheerleader. I tried to shy away and keep looking but Stephanie would have no part of that. "Yes, I am sure that you can help. This is my boyfriend and he is looking for a dress for a very special date tonight. It needs to be something of exceptionally good taste but at the same time something sexy. Do you think that you can find him something?" The young girl stopped where she was. She seemed to be thinking for a minute to make sure that she had heard correctly. She looked at me and smiled and then looked to Stephanie. "Well I think that we can find him something. Is his date with you, or does he have a boyfriend of his own?" She giggled as she asked this. "Do you know what size he wears, or do we need to measure him up?" By the time we left the store, I had purchased a white dress made from a soft shiny fabric that had a pattern of roses woven into the material. I had tried it on and it fit very snugly, but Stephanie said we would take care of that later. The skirt came only to mid thigh, and the neckline fell to bust exposing level. She said that we would fix that also. The next stop was at Victoria's Secrets. Stephanie walked right up to a clerk and told her what we needed. "My boyfriend just bought a new dress for our date tonight and he needs some help with his figure. I was thinking of an over bust corset with firm boning and added lift." The clerk looked at me and smiled, "Don't worry dear. You are not the first and you won't be the last. I have worked here for five years and I have probably fit as many men for corsets as I have women. The men always pose a bit more of a challenge, but I am sure that we can give you the curves that you are looking for." When we left the lingerie store, I was wearing the corset. It was heavily boned and gave me a slim waist that flared to my hips, which now seemed rounder. The under wire supports and padding in the bra section gave me a reasonable bust line. I had on the matching panties and shear white stocking that attached to the garters. Our next stop was the shoe store where I bought a pair of white multi strap sandals with three-inch heels. Stephanie wanted something higher but settled on these so that I would have an easier time walking in them. We bought jewelry, a purse, some makeup and perfume before we were done. At each store, the clerks would laugh as they saw the name on my credit card. "Here you are Thomas. Now enjoy you new dress, or your new shoes, etc". I blushed bright red every time but there was nothing that I could do. When we finally left the mall and were driving back to the apartment, Stephanie said, "Well, that will take care of five demerits, only two more to go." At the apartment, Stephanie was in a frenzy of activity. She showered and dressed, fixed her hair and did her makeup. She wore a midnight blue dress that looked great on her. She was the picture of elegance and femininity. She had me shower while she was dressing and then helped me to get ready. I could have gotten dressed myself with the exception of the corset. I thought that it had been laced tightly at the store, but Stephanie managed to pull it in another inch. By the time that she was through I wasn't sure that I was going to be able to breath. The dress now fit very well. The corset had pulled me in where it had been snug and added curves to fill it out. Stephanie spent extra time doing my makeup and then placed the wig on my head and brushed, combed and sprayed it into place. When I looked into the mirror I was amazed, I had never looked so good. Stephanie said that it was OK, but I would get better with practice. Dinner at the French restaurant went well. The prices were incredible, but I just shrugged and went with the flow. We had finished dinner and were having an after diner drink when Stephanie decided it was time to pay off the last two demerits. "I want you to go to the restroom. While you are there, take care of anything that you need to and fix your makeup. When you are done, I want you to take off your panties and put them in your purse. Then come back to the table and we will have another drink. Maybe we'll visit the bar for a nightcap before we leave." Her smile told me this was an order and I had better go. I made my way to the restroom and quickly took care of business. I was standing at the mirror fixing my lipstick when an older lady came in and stood next to me checking her makeup also. She touched it up quickly and then turned to leave. Before she left however, she turned and spoke to me, "I give you a lot of credit dear. It must be quite difficult to go as far as you have, and you are very near to being totally passable. Let me give you some advice, work on the way that you move. I noticed you when you walked across the restaurant, and I noticed your movements just now when you did your lipstick. Your movements are a little forced and stiff. Girls flow when they move. One motion leads into another. I am sure that with a little practice you will do just fine. I know you fooled my husband, he watched you wiggle all the way across the room." She left the room and I was scared stiff. If this old lady had figured me out, whom else knew? How could I go back out there? I was sure that everyone would be watching for me and would break out in laughter when I walked out. I stood there for several more minutes getting my confidence pulled together. When I did, I got ready to go, but stopped a step before the door. I still had my panties on. If I went back to the table with them on, no telling what Stephanie would do? I retreated to one of the stalls and pulled them down and stepped out of them. I picked them up folded them in half and tucked them into my purse. When I took my first step, I discovered my latest problem. With out the panties, I had nothing to hold my male parts up and out of site. It might not have been so bad with a different outfit, but with this short, tight skirt, there was little to provide cover. Worse yet, while I stood there thinking about it, I started to get an erection. Now, I was in real trouble. After standing there fore several more minutes deciding what to do, I chose to deal with it the old fashioned way, I masturbated. It didn't take long, and no one came in while I was doing it. When I was done, I used wet paper towels to clean up. I used cold water to help things shrink and it helped. I knew that I could stand and walk with out too much trouble, but I would have to be very careful when I sat. As I approached the table where Stephanie and I had been sitting, I could see that she was gone. Our waiter showed me to the bar, and there she sat at a small table on a high stool. This was going to make things very difficult. I walked over to where she was and stood next to the stool. It had arms and a back but was very tall and would require a step up on the footrest to get seated. I held my legs as close together as I could and stepped up. I rotated quickly to a seated position making sure to smooth my skirt under me as I did so. "Very good. I thought that you might have more trouble getting on the stool, but you handled it well. Now open your purse and let me see. Watching how you moved, I am quite certain that you did as you were told, but I still think that I had better check." She looked into my purse and smiled. "Now tell me, what took you so long in there? Even real girls don't take that long." I told her the story about the lady that had talked to me. "If she was able to figure me out, who else do you think could tell? She made it sound as if it were obvious to her." Stephanie smiled, almost letting go with a laugh, "Well, I would venture to say that any of the women here tonight could tell if they looked at you more than once. But I will bet that the only men that noticed were the gay couple sitting across from us. I think they figured you out quickly. I don't think any of the other men saw you as anything except a desirable woman. Now let's have a drink, and then we can go home. I have an itch that needs scratched, and you'll be doing that scratching for me." For the next year and a half we played this same game. Stephanie took advantage of the situation she had me in to provide her amusement and entertainment. She became increasingly more cleaver in finding ways to embarrass and expose me. She continued to document my torment by taking pictures every time I dressed and of the many little scenarios that she led me through. She pushed me to leave my wife, but I insisted that I couldn't do it. We would argue about this often. I could tell when she was upset about it because she became more devious in her punishments. Over time, I had acquired a French Maids' outfit that I wore while cleaning her apartment and serving her dinner. I also had a little girl's dress and pinafore that she dressed me in and took me to the park, taking my picture sitting on the swings. I had a number of dresses in casual styles as well as eveningwear. I had spent more than a few thousand dollars on the outfits that she had made me purchase. Also, she had made me purchase most of them in person, while letting the sales clerks know that they were for me. At work, things had gone much better. I had received another promotion, being selected as a department manager. Stephanie was upset about it because one of her best friends had also been in the running for the position and I was chosen over her. In general, I did not get along with many of the women attorneys in the office, so this gave me a little boost in the ego department. Stephanie warned me not to get too full of myself, but I didn't see it that way. Here at the office, these women reported to me, and I took pleasure in the fact that at least here, Stephanie didn't have such a firm grip on me. I was soon to find out how wrong I could be. Barbara and Stephanie had met at an Awards dinner that the law firm gave annually. Some of the awards were based on personal performance and accomplishments and others were just fun things to keep the evening interesting. I had tried to keep them apart, but in the end was not able to do so. By the end of the evening, they were chatting like old friends. Unbeknownst to me, Barbara confided in Stephanie that some of the spark had gone out of our relationship and that she was afraid that I was working far too much. "I know that I take long trips for my job, but I am afraid that Tom sees these as opportunities to put in extra hours at the office. Sometimes when I get home he is so worn down that he is not even in the mood for sex. Well, he has a birthday coming up in two weeks and I am sure that he is expecting the same night out for dinner that we always have, but I am planning something different. I am giving him a surprise party, and then a long weekend of every lustful activity that I can think of. That should get him back to his old self." When I ran into Stephanie the next day at the office, she was almost violent. "I want you to divorce her! You have been holding out on me for too long and if you don't do it now, I don't think that you ever will. I want your answer today, and it had better be the right answer. If its not, I am going to do something truly diabolical, I promise you that!" I spent most of my day thinking about Stephanie's threats. At last I had come to a decision. I would not give in. If she wanted to expose me, she could go right ahead and do it, but I was sure that I could deflect most of it and patch up the rest. I needed to get back control of my life. When I met her after office hours, I told her what I decided. The anger boiled, but then seemed to subside. She became apologetic. "Tom, I didn't mean it. You know that I would never hurt you. I am sorry. If you are willing to give me little pieces of your time, I am still willing to indulge in your games. Just don't cast me aside." Well, this was much better. At last it seems we had found out who had the stronger will. She could never expose me, because that would mean that she would lose me also and that was something that she was not ready to do. Now it seems that I had the best of both worlds. As it turned out, Barbara was leaving town on Thursday and would not be back until the following Saturday which happened to be my birthday. She had made reservations for dinner and a room in town for the night so that we could celebrate. This would give me the chance to use my newfound power to the best of my advantage. I would spend the entire week with Stephanie and meet up with Barbara on Saturday for what was always a great weekend of uninhibited sex. On Friday night, Stephanie couldn't wait to get to her apartment. When we arrived, we hurried and changed into comfortable but sexy eveningwear. She had planned dinner and for once she was serving me. Things couldn't be going much better. The wine that she served was excellent and I drank more than usual. By the time that dinner was over I was quite tipsy. We sat in the living room and talked for a long time. I wanted to get to the bedroom, but Stephanie had other ideas. When I looked her in the eyes, there was a new and different look about her. I started to say something about it but she cut me off. "Relax. Listen to my voice and relax. I want this night to be special, so just sit here and relax." I found that there was little that I could do but obey her. Every muscle in my body seemed to be in the relaxation mode already. I sat there looking at her beautiful eyes and listening to her talk. "I gave you something in your wine tonight to help you to relax. Now I want you to listen to my voice and continue to relax. When you feel that you are totally at ease, I want you to close your eyes and sleep." It was a while later when I woke up. When I did, I felt more relaxed than I had in quite sometime. As I came to, I became aware of another person sitting in the apartment with Stephanie and me. I knew that I should be concerned, but I was not. I was just relaxed and calm. Stephanie looked at me and smiled, "Well, welcome back. We have a visitor. Dr. Baxter, this is ?Tiffany', my boyfriend. Tiffany, this is Dr. Baxter. Say hello to her." I smiled and said hello. I wasn't sure what was going on, but Stephanie had called me Tiffany, and somehow that seemed to be right. I knew that I should have a different name if I was her boy friend, but she said my name was Tiffany, so it must be. Stephanie and Dr. Baxter talked for a long time mostly about things that I didn't understand. I felt so stupid. They would occasionally talk to me in simple words and sentences and I understood them completely, but then they would talk to each other about things that didn't make any sense to me at all. Finally I heard Dr. Baxter say, "Let me demonstrate." Then she looked at me and said, "Tiffany needs a nap." It was some time later when I awoke again. I remember hearing a voice saying, "Wake up princess." Suddenly I was wide awake again and sitting on the couch between Dr. Baxter and Stephanie. They talked for a while longer and again I didn't understand a thing that they had to say, until Dr. Baxter said, "Ready for the test?" She looked up at Stephanie who was nodding and said. "Tommy is back." With that simple statement, I was back. Me! Tommy! Not Tiffany! And further more, I was aware of everything that had been done and said tonight, at least most of it. All of the conversations that Stephanie and Dr. Baxter had shared were sharp in my memory. I had been drugged and then hypnotized. It had started with the wine, and when I was out Dr. Baxter had shown up and finished the job. While I was under, they had created Tiffany. Well, this was some kind of a joke and I was going to clear things up right now. I reached forward towards Dr. Baxter trying to get a hold on her. When I did, she would undo all of the things that she had done. "Freeze!" That one word stopped me cold. It wasn't just a reaction to the spoken word, I could not move. Stephanie smiled, as she looked me in the eye, "You didn't think that it would be that easy did you? Dr. Baxter has given me a number of simple command words to aide in your training. It will be so much easier when you realize that you no longer have a choice, but until then, it is best if we have these controls in place." Stephanie came forward with some rope and began to tie me. She tied my ankles together and then my knees. She tied my hands in front of me and then secured my elbows to my waist. As a final act, she placed a ball gag in my mouth and tied it behind my head. She checked everything to make sure it was secure and said, "Relax." Hearing this word, the freedom of movement was returned to me, except that I was now bound into position and was going nowhere. "Now while you are here, let me explain things to you. I need to do this, because once Tiffany is back, she won't understand a thing. She's a little slow sometimes." She smiled and went on, "It was very disturbing when you decided that you could take control of our relationship. I mean after all, look what I have done for you. When we started our adventure, you were nothing more than a cheap slut of a cross dresser. I made you into what you are today, a lovely very passable young lady. It was totally unfair of you to think that you could take away from me that which I had created. Well, with a little help from Dr. Baxter, I have things in hand again. I wanted you so badly when you were a man, now I will have you as a woman." The reality of what she said was starting to sink in. Somehow, I had let myself be programmed while under hypnosis. I listened as Stephanie continued to speak. "I will let Tommy come around occasionally, but most of the time you will be Tiffany. Do you like your new name? I think that it is very feminine, soft and sweet just like you. Your whole name will be Tiffany Olivia Mills. Isn't it pretty? Your initials spell Tom isn't that cute. Every time you think about that, or use your initials, you will remember for just a few seconds who you used to be. Now, how often you are allowed to become Tommy again will depend entirely upon your behavior, so it is important for you to always be a good girl. Now, there is one more thing that you need to do tonight. Dr. Baxter needs to be paid for her services. I am going to untie you so that you can sign the check, and then you will show how grateful you are to her. Do you understand? I want you to, ?Behave'. It was another of the control words. I was untied, but I just sat there. Stephanie handed me a check, telling me to sign it and I did. For what she had done to me tonight, I had just paid Dr. Baxter $5,000. When I handed her the check, Stephanie looked at me and gave the command. "Now that you have paid the bill, I want you to take Dr. Baxter into the guest bedroom and attend to her needs. Make sure that you do as you are told, or we will have to find an appropriate ?punishment'." Another of the control words. A wave of fear swept over me. I knew that I had better not fail to please Dr. Baxter, for whatever the punishment was, I wanted no part of it. When I woke up in the morning, I found myself tied hand and foot. I was wearing a diaper and a pink nightgown and sucking on a large pacifier. I tried to spit it out but I could not. It was not fastened in place but I still could not spit it out. Dr. Baxter was gone and I lay there remembering the escapades from last night. Her sexual appetite was enormous. Mostly she had me use my tongue to fill her needs but in the end, she had allowed me to enter her. She had yet another earth shaking orgasm and this time I joined her. Funny thing though, my orgasm seemed to disgust me. I felt dirty and cheap. The doctor had consoled me, and that is when she put the diaper on me. It was sometime later when Stephanie came in to release me. She smiled when she saw me there. "The doctor has a nice touch don't you think so?" I frowned and scowled and tried to spit out the damned pacifier but I still could not. "Well don't you worry, I can see that you are upset, but that's alright because, ?Tiffany is here!" With those words spoken, Tom was gone again and Tiffany was back. I was happy and felt relaxed. I reached up and took the pacifier out of my mouth and looked at it. "Stephanie, don't you think that I am too old to suck a pacifier? I mean it feels good at night when I am going to bed, but sometimes I think that I should give it up. What do you think?" "Well sweetie, I think that you can give it up any time that you want to. But I also think that if you need to wear diapers to bed, then you should use the pacifier also. When you are a big girl, you need to act like a big girl, but when you are not, we will have to see." I looked down at the diapers and turned red. "Did I have an accident again? I'm sorry, I try so hard to not have accidents, but sometimes it just seems to happen." I broke down in tears. Stephanie held me close to her and patted my head. That is OK dear. Accidents can happen. We will just have to make sure that when you feel like a little girl that we remember to keep you in diapers. She leaned forward and gave me a kiss on the forehead and everything was suddenly better. Going back to the office on Monday offered some relief from the torment of the weekend, but my sense that I had any control of my life soon spiraled downwards again. It was only 9:30 when I was summoned to the executive offices to visit with Mr. Jessup, he was one of the senior partners of the firm, and the one who controlled the division in which I worked. When I entered the office I noticed that Mrs. Karnow was also in attendance. She was from the HR department and it was never a good sign if she was present. Mr. Jessup started the meeting trying to be tactful and almost evasive of the issue that he was trying to present, but Mrs. Karnow was having none of that. She jumped right in and let me know exactly what was going on. "Over the last three months, we have received several complaints of sexual harassment from various women that you come in contact with on a daily basis. As you well know, this firm takes a dim view of this type of activity, as does the federal government. There are strict laws that provide both for protection against this type of behavior, and for specific actions that must be taken against those who violate the rules. I will be working closely with Mr. Jessup on the investigations into these matters. I warn you that this is a most serious situation, and suggest that you cooperate fully. Also, if for any reason you feel that this might compromise your position in terms of moral, ethical or legal standards which govern this company, you may choose at any time to terminate your employment with out loss of pay or trailing benefits. If however the investigation should find reasonable cause for dismissal, and you have not by that time made the decision to voluntarily leave, you will be terminated with cause and lose all benefits as well as any opportunity for unemployment benefits. Have I made myself clear? Do you understand?" I sat there dumbfounded. I didn't know how to answer. I knew that I did not get along with many of the female attorneys in the office but I had no idea of what I had done that could be considered that offensive. I left the meeting shaking my head. My world had just gone from bad to worse. I sulked back to my office and kept a low profile for the rest of the day. It was a little after 5:00 when Stephanie stopped by the office. This was the first time that I had seen her today. I had been afraid that she would have more surprises for me today after what she had pulled yesterday. By now however, I was starting to feel that I had regained at least some degree of control. She smiled and asked me if I had any plans for the evening, and I knew that even if I did, she would change them for me. As it turned out, she decided that I needed a refresher course in how to treat a woman properly, and that there was no better way to learn, than to be put into a situation that would remind me of what a pathetic man I was. By 9:00, I found myself dressed in a leather mini skirt, halter-top, five-inch heels and hooker makeup, being dropped off at a lesbian bar. I had strict instructions that I had to pick up the biggest roughest looking butch that I could find. I then had to have sex with her before I could leave the bar. There would be no mistaking whether or not I was successful, because she knew that I would ?behave'. That was it. Hearing the control word, I had no choice. Even though I was conscious of what I was doing, I knew what I had to do. There simply was no other option. I wiggled my way into the bar and surveyed my choices. There were a lot of them, but I wanted to be sure to choose the right one. Stephanie would not tolerate me making a quick decision and selecting the wrong girl. I ordered a white wine and started making my way around the bar. It only took one trip before I knew whom my target would be. She was a huge woman, probably 6 feet 3 inches tall and 250 pounds. She wore blue jeans, a denim shirt and had her hair cut in a long stand up spike. I worked my way to the end of the bar and positioned myself to where she could not miss seeing me. I talked to a few of the passer bys, and flirted recklessly. It didn't take long before my bait worked. "Hi, my names Melissa, can I buy you a drink?" She breathed down my neck as she asked over my shoulder. I looked up coyly as if I were thinking it over, and finally made up my mind. "Well, I don't see why not. If you are kind enough to offer, I should be kind enough to accept." We sat at a small table near the end of the bar. As I scooted up onto the stool I let my skirt ride up high on my thigh. This move was not wasted on Melissa. We exchanged small talk, but it soon became clear what was on her mind. She referred to it as needing ?a fix' to get her through the rest of the night. She suggested a back room at the club, and we were soon on our way. It was beginning to look like this would be easier than I thought, and I would soon be out of here. When we made it into the room Melissa, (call me Mel), locked the door and was on me like a lioness on her prey. With her first kiss, her tongue explored the depths of my throat. Her hands were all over me and her pelvis was grinding at mine. There was a small metal-framed bed in the corner and she pulled me towards it. As I sat on the bed, she pulled down her jeans to expose the men's briefs that she wore. She quickly disposed of them also. Before I could say a word she pulled my head to her waiting womanhood. Melissa lasted through two orgasms before she collapsed on top of me. I had no choice but to let her have her way. When she had finally pulled my skirt up and my panties down, I started to find out how much trouble I was. She hit me so hard with the back of her hand that I thought that I would lose consciousness. She learned hard against me putting her face right in front of mine and spoke I a low growling voice, "So, what we've got here is a prissy little fairy boy. Well fairy boy, let's see what you can do with that little piece of meat." When she grabbed me with her hand, I thought that she was going to pull it off. She massaged me until I was hard and then climbed on and rode. I came quickly much to her satisfaction. "I can see why you dress like a sissy boy, because you sure can't use that thing like a real man. Well, I hate to let you go with out trying to let you experience a little sex as a woman, so let's see what I can do to help you out." Before I knew what was going on, she had pulled a red bandana type hankie out of her pocket, tore it in two, and was tying my wrists to the frame of the bed. When I started to scream, she tore my panties off and stuffed them in my mouth. She tore off a piece of the sheet on the bed and tied my feet together and then pulled them against the leg of the bed. When she was done, I was in a half sitting position with my legs pulled to the side. She checked to make sure that her knots were tight and then left the room. I sat there for quite a while contemplating my fate. I struggled with the bindings but had no success if getting free. I was hot, sweaty and worn out when I finally heard the door open. Melissa walked back into the room but this time she had a companion. It was the bartender that had been out front when I had first arrived. He was tall and thin with an obvious gay look to him. He smiled and giggled as Melissa pulled him over to the bed. "Take a look Phillip. Other than your own little sissy boy, have you ever seen such a pathetic excuse for a man? Now, I want you to have this little sissy service you as a man. And if he doesn't do good enough, I will have to go out on the street and find another man for him." She pushed Phillip towards me and laughed as she again walked out of the room. Phillip just stood there looking at me as if he didn't know what to do. I tried to plead with him but the panties stuffed into my mouth cut my pleas to mumbles. Slowly, he made his way closer to me and when he was only a few steps away, he reached down and unzipped his pants. Before he moved any closer he reached into his pocket and pulled out a knife. He opened it, and set it down on the end of the bed. "Just a little precaution, incase you decide to bite! Now when I take those panties out of your mouth, I expect you to be quiet. Then, I expect you to act like a lady, and give me the best blowjob you can. Do I make myself clear?' I nodded my agreement. I had no choice in the matter. I now was not only in fear of what Stephanie would do to me; I was also in fear for my life. Phillip picked up the knife and used the tip of it to pluck the panties from my mouth. I gasped for breath as he did. When I looked up, he was still holding the knife, and now he was pushing his semi- erect penis towards my face. "Open up sweetie. This is what you have been waiting for." I opened my mouth wide enough for him to gain access but not full wide. He used his free hand to grab the back of my head and then he thrust forward with his hips. I gagged and choked, but he held my head firmly in place. Soon, he was pumping in and out, each time trying harder to penetrate my throat. It didn't take long when suddenly he pulled hard and thrust deep and held me tight. He pumped stream after stream into my mouth and down my throat. When he was done, he pulled away and