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Girl Mode, Part 2. It is fall now. We have had a warm summer and fall. It has been fun. Hanging out at patio bars, and having barbeques. Last weekend we had a barbeque with 20 guests. It went on late, with lots of drinking and dancing. There were Teresa's friends, some of my co-workers, and of course Sandy and Bob. It was a warm day, so I wore a red over bust corset with a skirt and 3 inch wedge heels. Over the corset, I had a Bolero jacket. It covered my shoulders and the back of the corset. It had one button at the front, which was just enough to cover, without looking slutty. I looked awesome. Sandy wore a dress and flat sandals. Most of my co- workers were dressed a lot flashier than one might have expected for a barbeque, but Teresa is now a VP of sales, and they know that she always dresses to kill. And one should always be dressed the same level as the hostess at a party. I got lots of compliments about my look. It never gets old being told how pretty you are. I woke up quite hung over. It was quite a night. I drank a few more than I should have. I flirted too much and danced a lot. More than once a man used a slow dance to cop a feel. I was a bit drunk so I did not object much. Or perhaps I liked it. Maybe I am just a party girl at heart. We left work early today. The company lets people go 2 hours early on Fridays. I am now at a spa with Teresa. I just had my eyebrows waxed. They took off more than I wanted, but they do look good. It used to hurt a lot. Now, it just stings for a moment. I don't know if my skin is getting used to it, or I am accepting it a normal. I think the latter is the reason. They are doing my nails now, and I love it. I never used to like having somebody fussing about me before, but I have changed. I put on a dress that I picked out. It is a pale blue wrap dress which is loose at the bottom. It flows when I walk. I matched it with high black stiletto pumps. They contrast with the dress, to draw the eye to them. Teresa is wearing a silk top and leather pants with high heeled boots. As always, she looks hot. Now we are off to the bar to meet Patrick. In the car, Teresa asks, "Are you looking forward to seeing Tom again? Have you got your outfits planed out?" I exclaim that I am not gay. "I don't want to lead him on since I can't go anywhere with it. It would not be fair. And yes, I have thought about outfits." Teresa says, "You are mostly a girl now. You should try men. I could help you change your preferences." I reply, "You can't change sexual preferences like that. It is not like learning to like Sushi or play a piano." "You once said you would not pass as a girl. Now look at you. Would you let me try? Give me until Tom gets back." I don't see how she can do it, but I agree. "Wonderful", she says. "We will start tomorrow. You and I will spend an hour or two each night. If you do not want to date Tom when he returns, you don't have to. The only thing I ask is that you have to trust me, and do what I ask until then." "Ok. But I this is between us. Nobody else can know. Nobody else will be involved." I figure that will prevent her from asking me to do something with a boy. I don't like that idea. She says that is ok. And we arrive at the bar. We go in. Patrick is not here. We have a table reserved, but we are early so it is not ready yet. We wait at the bar. It is one thing to dress up, but sitting perched on a high bar stool with a hottie like Teresa beside you screams out for attention. Bar stools had to have been designed by a guy. They have no backs on them, so you can't slouch. They are too high to put your feet on the ground, even in heels, so you end up propping your feet on the bars at the bottom, which shows off your shoes, and pushes your knees up high enough to make your skirt ride up and flash some leg. The bar is mostly full of the after work crowd. And many of them take a shot at picking us up. Finally Patrick arrives, and we get our table much to the dismay of our would-be suitors. Our hero saves two damsels in distress from the dragon's lair. Ok, that is a bit over the top. Tee hee. I am screwed up. I have noticed that when I look at girls now, I think more about what they are wearing and whether I would look good in it, than about having sex with them. We have supper, and then a movie. After this we go home. It is not late, but Patrick is leaving early tomorrow for his annual 2 week fishing trip with some friends and wants to get home early. When I get up, Patrick is loading his fishing gear and tents and coolers of food and cases of beer into his friend's pickup truck. I would love to go with them, but it is a "guy trip". Rats. That is one of the disadvantages of being a girl. I don't get to do the fun boy things I used to. After they leave, Teresa says "It is time to start your training. I have thought about it a bit, and it will be 2 hours per night, plus all weekend long. We don't have much time. 4, maybe 5 weeks until you have to be ready." "We are going shopping." I don't see how shopping is going to make any difference to my orientation, but shopping is fun, so let's go. Teresa takes me to a specialty leather store. "Specialty" means that they have leather skirts and dresses and pants. They also have all kinds of corsets, ranging from plain white Victorian styles to dangerous leather ones. There are some with a buckling front with locks on it and D-rings at the waist. In the back of the store they have French maid uniforms and a huge collection of shoes and boots. Teresa suggests that I try on an old fashioned white corset. She picks out one that has lots looks plain, but has a lot of boning. Teresa is heading straight to an area where they have bondage gear while I go into the change room to try it on. It takes a time to try on a corset. First I have to unlace and take off the one I am wearing, and then get the new one on. Not to mention that I have to unclip the garters and reattach the ones on this new corset. I lace it up, but it has a smaller waist than I am used to. I stick my head out the change room, and call Teresa. She is paying for a bag of items. She said, "I will be right there. Just wait." She comes into the change room after a few minutes holding a pair of ankle strap pumps. "What's the problem? "It's too small. Go and get me one with a bigger waist. This one is 25 inches. I need at least 28 inches." "Let me see. Turn around." I do, and she starts to pull the laces tighter. I protest, "That is too tight. I can't breathe." She responds, "If you can talk, you can breathe. Stop complaining." And she pulls more. I can see my waist getting smaller in the mirror. Finally she stops, and ties off the laces. I can only breathe from the top of my chest. "You look perfect. Look at yourself," she says. She is right. It does look good. I look good. Next she helps me put on the shoes she brought in. I need help, because I can't bend over in the corset. I was wearing t-strap sandals, so I could not even kick those off with taking off the straps, and I certainly could not do up the ankle straps on the new ones. The heels are really high. They are about 5 inches high, and have no platform. Lots of girls are wearing high heels at the moment, but most of them have high platforms to make them easier to wear. She says, "You should wear it home." Before I realize what she is doing, she pulls off the tags. She picks up the corset I wore in here, and leaves the room with the tags. Now, I have to buy it. I put my dress back on. My dress has a gathered elasticized waist, which is good because it clings to this new corset. Funny, but Teresa suggested this dress this morning when I was getting dressed. I leave the change room, and head to the cashier. I have to take small steps in these shoes. A year ago, when I was a boy, I could not have even walked in these shoes, but now they just feel a bit higher than they used to. I remember how I had learned to walk in heels back then. I guess I can do these shoes. Teresa informs me that she has already paid for everything. She has bought herself a pair of strappy sandals with really high heels. We leave the store, and make our way to her car. She sways seductively in her high heels and her butt looks amazing in her jeans. She drives us to the mall next for more shopping. I love shopping, but it is a long walk across the parking lot. I would not have considered this far this morning, but now with these shoes, I am walking slowly. Soon, I am also slowed because I cannot breathe deeply in the corset. We end up walking around the mall going into store after store. Teresa has me try on dress after dress. I love this part, but it is tiring clicking around on the hard floors and struggling to get dresses on and off in this corset. All the time Teresa is asking me what I think Tom would like and where I want to go on our date. We pick out a dress. Actually, she picked out the dress. I was not asked, so much as told. It is a beautiful red, tailored dress with a back zipper, and long sleeves. It fits perfectly, everywhere except at the waist where it is a bit loose. The staff at the store tells me that they can alter it. They call for a seamstress. A lady comes out of the back, with a tape measure dangling around her neck and carrying chalk and pins. This is the uniform for seamstresses. When I used to be a man I learned this while buying suits. The seamstress measures me and pins the dress at the waist to get it taken in. She can tell that I am wearing a corset. She comments how nice it is to see girls wearing traditional clothes. I pay for the dress, and leave it at the store. I will have to get it in 2 days when the alterations are done. Finally we go into a department store and to the makeup counter. I end up getting a blush and lipstick. Once again Teresa is doing all the deciding, and telling me what colors to try. After all this shopping, we head for home. I am carrying a pile of bags full of clothing and makeup. It is early afternoon when we get home, and we skipped lunch. We make a light lunch and open a bottle of wine. I do not eat much, because it is hard to eat when I am wearing a tight corset. After lunch, Teresa says, "It is time to start your training. Take off your dress and come to the movie room. Don't forget to pee first." I go to my room and take off my dress, and put away the new clothes that I bought. I am wearing the corset, stockings, high heels, and control panties. I always wear the control panties to pull all my boy bits in and give me a smooth look. I go to the bathroom to pee, and I check myself in the mirror. Dressed this way, with my perfect makeup, with red lips, I look like a man's wet dream. I am getting hot just looking at myself. Then I go to the movie room in the basement. It is a room that Patrick has built, with a projection television, and comfortable couches and chairs. He spent a lot of money on this room. Teresa is there. She has me sit down in a chair. She picks up the remote control and starts a movie playing. The movie is a series of short porn flicks. They are all about transvestites having sex with men. I tell Teresa, "Watching some movies is not going to do anything to change me." She replies, "Time will tell, and I am not through here." She slides her hand into my panties, and pulls my penis so it is pointing up. Then she starts rubbing my penis through the panties. It takes a few minutes but I am getting pretty hard. The porn is not arousing me, but Teresa's hand sure is. It feels good. After about an hour of this, I am ready to explode, but Teresa stops rubbing just in time every time. I grab my penis, but she pushes my hand away. She keeps doing this. Soon I am begging for release. Teresa says, "Are you a boy or a girl?" I reply, "I am a boy." "Do boys or girls wear dresses?" "Girls," I reply. I am reaching that point where I will say anything for relief. She keeps going, both on my penis, and with the questions. "Do you wear dresses?" "Yes." "And does that make you a girl?" "No I am a boy." At this she stops rubbing. I can't think straight. I just want relief. "I am a girl. Please don't stop," I beg. She now starts rubbing again, but a bit more slowly. "That's a good girl. Do boys or girls wear high heels?" "Girls do," I reply. She goes on, "And do you wear high heels all the time?" "Yes." "And are you a boy or a girl?" "I am a girl." She keeps going. And the movie keeps playing. There are transvestites kissing boys. There are boys screwing transvestites from behind. There are transvestites being forced to give blow jobs. My head is swimming with all this. She is keeping me aroused, but not letting me cum. I try to get hands on my penis, but she keeps pushing them away. Teresa keeps up with the questions. Do you wear makeup? Do you wear corsets? Do you wear lipstick? Do you wear skirts? Do you wear stockings? Do you have smooth legs? Are you growing your hair long? If I don't answer yes, she stops pleasuring me. And she keeps making me say, "I am a girl." Finally she pulls out a document out of the bag and has me read it. Girl Contract. This contract will be valid until I have had 3 dates with Tom. Until this time I will remain dressed as a girl. I will wear skirts and dresses a minimum of 5 days a week. I will only wear pants 2 days a week. My heels will be a minimum of 5 inches high. My waist will be laced to 25 inches except when I am bathing. My makeup will be perfect every day. I will watch movies and read material as directed by Teresa. I will act like a feminine girl. Signed Tina "Are you going to sign it?" she asks. "Yes, just let me cum. Please." "As soon as you sign it." She hands me a pen. And I sign. I have no choice. I must do this. She giggles, and says now you can finish. And I do. It only takes about a minute. After which I collapse. The post orgasm release saps all my strength. She puts a blanket over me. Then she turns off the movie, and says, "You can have a nap now." And in a few moments, I am asleep. Sometime later I wake up. She tells me that I should get cleaned up. I go to my room and look in the mirror. I am a mess. Also the contract I signed is taped to the mirror. I strip to get in a shower. It feels so good to be out of the corset and heels. After I shower, I start to get dressed again. As always, I start with the control panties to keep my boy parts under control. Not that they are giving me any trouble. My penis is still flaccid from the orgasm. I realize that I have to put the corset back on. It is the only one that goes to 25 inches. I put it on, but I don't lace it up yet. First I put on stockings and my shoes. Once it is laced up, I won't be able to bend over and reach the ankle strap without a lot of effort. Then I lace up the corset part way. This is the best way to put on a really tight corset. Do it in stages. I do my makeup. Then I tighten the corset some more. Next, I put on my wig and comb it out. My hair has been growing and soon, I will be able to style it and not have to wear a wig. I am looking forward to that. Wigs are not comfortable. Of course none of the girl stuff is. Well maybe some dresses and skirts are if they are not too tight. I finish tightening the laces, and put on a skirt and top. The top bunches a bit with the corset. The elastic waist of the skirt still fits well. I find Teresa in the kitchen. She is cooking supper. She pours me some wine, and I help cook. Teresa is a good cook, and I enjoy helping in the kitchen. She is making perogies and schnitzel. I can pound the pork until it is thin, while we chat. Finally, I ask, "So what was all that about?" "What?" she replies faking innocence. "You know. The movies, the orgasm. All of it." She tells me, "You have to start getting used to the idea of sex with a man. The movies should help. The orgasm was to make you enjoy it. If I and not held your hands, you would have cum in a few minutes, and it would have been over. And you can't tell me that you didn't like it. You were begging for it." "Ok, but why the corset and heels and the contract?" "That is just part of the process. A teaching aid. You just have to trust me on that. Also, you are getting too comfortable in heels and corset, so I have to up the bar a bit. The contract is to keep us from cheating. " I am just about to say that heels and corsets are not comfortable, but she will probably then claim that I need more practice. I can't think of any other arguments against this other than, "5 inch heels are too high for the office. They look slutty, not professional". She disagreed, and told me that I would look great. All the girls would be jealous, and the men would love them. "If they are so perfect for the office, they why don't you wear them?" I had her now. "Ok, I will wear them. You know I am comfortable in heels anyway." She always claimed to be comfortable in heels, but I think it is just a way to make other women jealous. But, "in for a penny, in for a pound". Let's see what fun I can have. "You also need to wear a corset. Then you will know how I feel." Teresa exclaimed, "I don't need a corset. I already have a small waist." I counter, "You don't need waist reduction. You need to feel what it is like to wear stays all day. You have had me in a corset for nearly a year now. Or is it too much for you?" I know that Teresa is very competitive. She would not be able to resist. She did not get this far in the business world without being that competitive. In this respect she is a bit like a man. She exclaimed, "Ok, I will wear a corset too." I think she will regret that. But now I have her. "Let's add that to the contract." So now, the contract has added to it: Teresa's Contract. This contract will be valid until Tina has had 3 dates with Tom. Until this time I will remain dressed as a feminine girl. I will wear skirts and dresses a minimum of 5 days a week. I will only wear pants 2 days a week. My heels will be a minimum of 5 inches high. My waist will be laced to 22 inches except when I am bathing. My makeup will be perfect every day. Signed Teresa She signed it. She said it would not be a problem since she always wore a skirt suit or a dress to work, and always wore heels. I think she will rethink that after some time in really high heels and corset. She forgets that she wears comfortable clothes when she is around the house. I made her change. I can see that we will have to do some shopping for her. The next day we go shopping. The contract is a good excuse. Most of the shopping is for her. She has a couple of corsets, but they are more decorative than functional. She doesn't need much since she already has a 26 inch waist. Only a 4 inch reduction is needed, but that may be a bit hard. It might be harder on her than on me, since she is such a hard body with no fat to move around. We both need shoes. But what girl doesn't need shoes. But this time, we only buy shoes with really high heels. I even got a pair of pumps with an ankle strap with a tiny lock on the strap. Now I convince her that she should also get some boots with locks on them. I also buy a few new blouses, with smaller waist sizes, since with the new tight corset, they look better. We go to a store that specializes in leather goods. They also sell satin corsets. It takes hours to get corsets for her. It always takes a long time to buy corsets. First, you have to try on many to get a good fit. Also, it is not like buying shoes. You can't just slip a corset on. First you have to take off the one you are wearing. Then you pull the laces on the next one loose, and hook the bust around your waist. Then you tighten the laces bit by bit. Fortunately, there are two of us, so I can do her. We finally get three corsets for her. We also got measured for custom made ones. It will take a few weeks for delivery. Teresa and I both wear our new corsets out of the store. She is wearing pants and a blouse. We put on the shoes we bought earlier. She puts on the boots with the locks on them, and I wear a pair of blue sandals. The pants hide the locks. I am wearing a skirt, so I am not going to wear my locking shoes in public. Lastly, we stop and pick up my new dress that has been altered. I try it on, and it fits perfectly. It follows my curves, or I should say corsets curves, but it does not pull too tight anywhere. I can't wait to wear it somewhere. Since we have finished shopping, we decide what to do next. It is a nice fall day, so we decide to go to the waterfront area. The waterfront is a walkway along the lake with restaurants, bars, and stores on one side, and a grassy area with park benches and play areas between it and the water on the other side. It is a popular place for people to walk, bike, roller skate and for families to take kids. We plan to window shop, and stop for a late lunch. It is busy today. We look at a few stores, and decide to find something to eat. We end up having to walk quite a ways to find a place that was not too busy. We are a bit out of place. Other women are wearing pants, and a few in skirts. Some have little heels, and most wearing comfortable flats, or running shoes. We are wiggling along in our stilettos. It is the usual scenario. The men watch us, and try not to look too obvious, while their wives give that "What sluts! I wish I could walk in those shoes", look. My feet are hurting, but I am not going to admit this to Teresa. I am sure she is in pain too. Of course boots are a bit easier to wear than the high pumps I am wearing, due to the extra support. But she is not used to such high heels, and the locks on her boots prevent her from flexing her foot to stretch her calf. When we finally find a place to eat, we get seated. It feels good to get off our feet. I stretch out my calf muscles a bit, while making sure Teresa can see what I am doing. I know she won't say anything, due to her competitive nature. It is a small, but enjoyable revenge for the terms of my contract. We have something to eat. Neither of us can eat much due to the constriction of our corsets. After a couple of drinks, we wiggle our way back to the car to go home. It seems to be a long walk. We had strolled quite a ways looking at stores, and finding a restaurant, and now we are walking back in our too tight corsets, and too high heels. Once we arrive at home, Teresa informs me that it is time for another "Teaching Session," I protest. "How about doing it later. I am tired, and my feet hurt." She says "That's too bad. So do mine. Now get to the movie room and get that dress off." I obey, and we repeat yesterday's session. I am again in the easy chair, but this time she puts a penis shaped gag in my mouth. I am not going to talk back now. She puts porn on the big screen. First it is transvestite porn. Then it changes to transvestite bondage, and then finally some girl on boy blow job porn. Teresa teases me throughout this. It seems to go on for hours, but in reality it is less than an hour. She made me suck on the penis gag. I had no choice. As soon as I stopped sucking at the gag, she would stop rubbing my penis. It is a very effective method when I am on the edge. She let me cum while the male in the movie came all over the girl. After I cum, she reaches into her "toy bag" and gets out a blindfold. She puts it on me, and tells me that I need a timeout, and to think about the movies. I realize that she has put a blanket over me. It feels nice. Then the movie is turned off, and it is quiet. I can't tell if she is still in the room. I make a few grunts, but the gag is very effective. It holds my tongue down, and jaws open. After an orgasm, I am always sleepy. I am startled awake by Teresa removing the gag and blindfold. My jaws hurt. Apparently I slept for an hour. After my release, I put on a comfortable skirt and top and do my laundry, and some cleaning around the house. The rest of the evening is spent watching some television and relaxing. Monday morning comes, and it is back to the grind. Get up, shower, some coffee, then makeup, and decide what to wear. Of course today I will be wearing a tight corset and my 5 inch pumps. Other than that, I make sure my skirt is not too short, and my blouse does not show any cleavage. The difference between business professional and office slut is pretty small, and these shoes are pushing the envelope a bit. At work, I get a few comments on how nice I look. Some ask if I have lost weight and several of the women comment "How can you walk in those shoes? I could never wear them." I give the same answer, "Practice." They usually laugh. Some are jealous. But Teresa is also wearing really high heels. One girl dressed this way is a slut. Two is a trend. I would bet that by the end of the week, several of the women here will be struggling along in their highest heels. Work goes normally, but I have noticed that several of the men seem to be hanging out by my desk a bit. I can catch them checking to see if they can sneak a peek of my legs under the desk. I now know who likes high heels. Surprisingly, one of the men that seems to be here more often than usual is the CEO. His name is John. He came in the first time to talk to Teresa about a customer, but came back later, because he, "had one more question", and later for a signature on a sales proposition. Teresa was not there, so I tell him I would have her sign it and I will bring it to his office. Just before noon I go to his office with the papers. I am curious to see if he is really checking out my legs, since he is one of the few people here that know my little secret. I enter his office, and walk up beside his desk to put the papers on it. I bend over a bit to make sure my skirt is tight so he can get a good look. I watch his eyes when he thinks I am looking at the papers on his desk. Unlike the other men here, he is not looking at my legs. He is definitely checking out my shoes. This is interesting. Maybe there is more to him than meets the eye. He tells me that he wants to discuss something with me in private, and suggests that we should go out for lunch. I say that I will go and get my purse. He tells me to bring Teresa. I fetch Teresa. We stop at the women's to check our makeup. I tell Teresa what I noticed about John. She says, "Then we should put on a show for him." Being a gentleman, John holds the doors for us as we leave the building. But we know that it gives him a good look at our behinds. Teresa offers to drive us to the restaurant he suggested. As we walk to the car, our heels click on the pavement. It is a sound that drives any man crazy. Both of us are making sure that our heels hit the pavement harder than normal. By the time we arrive at her car, I can tell he is having trouble following our casual conversation. Her skirt rises up when she gets in the car. I know that it is up higher than it needs to. She attempts to smooth it back down, but a lot of leg is left showing. She is a good actress. When she drove me to work this morning, she did not have this much difficulty with her skirt. Since I am in the back seat and John is in the front, I can see whenever he tries to get a better look at her legs. Once we are seated at the restaurant, John starts the conversation with an instruction that everything he is about to say is not to be repeated. He informs us that he is planning on retiring from day to day control of the company. He wants Teresa to take the reins. She jumped at this opportunity. This would all be made public in 2 weeks. In the meantime, he will help Teresa learn what she needs to know for the position of CEO. I ask how whether the board of directors knew about this. He says "They don't know, but it doesn't matter. I hold 70% of the stock in the company, so I can tell them what to do. Their jobs are voted in by the stockholders, and I have majority control." Then he asks, "What do you know about the software department?" I reply, "I know it exists, but I don't know where it is, and I have never met anybody who works there." John explains, "Yes. I have kept it that way deliberately. The department writes software for use with our products. It runs autonomously. Financial, HR, purchasing, everything is done out of their office. This is because it is a special office. All the employees there are girls like you. They are all crossdressers and transvestites. Not all of them are passable. That is why it is a separate office. I am the only person from the head office that has been there, and the only people from that office who have been in head office are passable as girls. It has been quite a success. Opportunities to work while dressed as girls are hard to come by. While labor laws protect the transgendered, it can't force employers to truly break the glass ceiling. So the girls who work there work hard. They are producing great software. Most people at the head office don't realize how much profit they are generating. Software is something we can't charge for, but it enhances many of our products to make them more valuable. And the girls there love to come to work. It is very professional. There is none of the usual egos, and screw over your co-workers for a piece of the pie attitude that seems to form in offices. They love the business professional dress codes. I get an office full of employees who can't wait to come to work every day. It is a win-win for everybody." Now he comes to the point. "They report directly to me. But since I am retiring, they will need a new manager. Tina, I want you to take over that position. I realize that you have been a faithful assistant to Teresa, but she will get a new assistant when she takes over as CEO. You will be working out of the software office." "I am going to make sure you both get some significant stock options and of course raises appropriate to your new positions." He continues to explain the details of the changes over lunch. I wasn't asked about the changes, I was told. But it would be hard to turn down this sort of promotion. At least for a normal person it would. But I am a not exactly normal. I say, "I am a bit unsure about my ability to take on this role." John assures me. "Don't worry. The girls there will love you. And if you can manage Teresa's office, you will be able to run this with no problem. I will be there on a part time basis as your assistant to guide you along." Now it all comes together. If John is going to work there, he will have to crossdress. He hired me when he knew I was a boy. He has a crossdressed office. He is a crossdresser. I wonder how many other girls like me there are in the head office. I know better than to ask. That is confidential HR information. But I will be a bit more observant in future. I bet I can spot them if I look carefully. After lunch, John has Teresa drive us to the software office. It is about 15 minutes away from the main office in a commercial office unit. They occupy the second floor. We park in the underground parking lot. The spaces there are all reserved, and he has his own spot. As we walk across the underground garage, our heels echo loudly. With a smile, John says, "I love your shoes." Now I know for certain he is a crossdresser. We go up to the third floor. Our office occupies the whole floor. There is a receptionist. A pretty girl named Susan at a desk by the door. John takes us for a tour of the office. I am introduced to many people, and by the end, I can't remember most of their names. There are about 25 girls here. I notice that most of them are wearing skirts, dresses, and skirt suits. A few are wearing dress pants. All of them have perfect makeup. All but one, are wearing high heels. The girl not wearing high heels is wearing 2 inch wedges. She is the janitor, office girl, do everything girl. She looks quite young. I would never have guessed she is a boy. Her name is Virginia, but everybody calls her Ginny. After seeing the whole place, we go to John's office. He suggests that I shadow him for the day. Teresa says she has work to do, especially now that she has to start training her replacement. She goes back to the main office. John says we will get a ride back from one of the girls here. I spend the rest of the day watching and learning from John. My experience in software helps here, and by the end of the day, I am feeling confident that I will be able to take over in a few weeks. I am so wrapped up in the work that I almost forget that I am wearing a skirt and corset and heels. That is "almost". You can't forget that you're wearing a corset, as it is always squeezing you. And I end up walking a lot around the office. Thankfully it is carpeted. It is a lot easier to walk on carpets than hard floors. The washrooms are tiled, and when I use them I click loudly. I use a washroom often, because I can't hold a lot of urine when my bladder is squeezed by my corset. At the end of the day, John and I get a ride back to the main office and Teresa takes me home from there. My feet are killing me. Or I should say these shoes are killing me. Teresa says that she is fine in her shoes, which are as high as mine, but I think this is for two reasons. The first is that she was probably sitting for the rest of the day after she left me, and second is that she is lying. She is very competitive, and loves to tell how she is "comfortable in heels". Tonight with my training session, she pulls out a leather collar. It has a strap attached to it, and two wrist cuffs attached to that. She put the collar on me. The surprise is that the strap hangs down my back. She puts my wrists in the cuffs, and buckles them snugly. My arms are completely immobilized. And the collar is quite wide, and keeps my neck straight. I can barely turn my head in it. I ask why the restraints and she says "I don't want to keep fighting with your hands to keep you from rubbing yourself." And then she adds the gag and starts the session. The teasing is driving me nuts this time. When I finally cum, it feels like an explosion. She blindfolds me and puts a blanket over me just like last night. I am almost asleep when I am startled by a sound. I can't see, but I am sure it is Teresa breathing heavily. She is masturbating too. She is somehow getting off on this whole thing. The next month goes by. I work at the software/crossdresser office about half of the time. I like working there. The girls are all sweet to me. Of course being the boss is kind of fun. John announces that he will be retiring at the end of the current week. Teresa and my promotions are announced, and a notice is put out for a replacement for my position as Teresa's assistant. I was right about the office dress code. The women all started wearing higher heels, and more dresses, and less dress pants. Women are like that. They put subtle pressure on each other. Not to mention that they observed that Teresa and I, who are always dressed in office professionals or as I like to call it, office sluts, got the big promotions. And quite a few want the position of Teresa's assistant, especially now that she will be CEO. The training sessions continue. Teresa adds a butt plug. She says I need to get used to this. She gets larger ones. And a vibrating one with a remote control so it can be controlled from something that looks like a key ring remote for a car. Let me tell you, it is hard to think clearly when you are bound, gagged, porn in front of you, teased, and your ass is stretched, and stimulated by the vibrator. The scary part is that I am looking forward to the sessions. I am getting used to the gay part, and the orgasms are great. Patrick came home from his fishing trip. I wonder how Teresa is going to explain the training sessions to him. It turns out the she doesn't. She just changes the schedule to mornings, before work. Patrick goes to work before us, so we just get to work a bit later each day. But being the boss has its privileges. He asks about why we were always wearing heels, and corsets, which I might add he likes. Teresa told him that is a bet between us, and that it goes on until I have been on three dates with Tom. I can tell that he likes it, because I came in from grocery shopping, and caught them in the kitchen. He had her bent over the table, and was screwing her from behind. The table had slid and was wedged up against a cupboard. They did not notice me, because he was too busy pounding her, and she was yelling. "Fuck that hurts. Oh please don't stop. Oh yes, fuck me, fuck me, fuck me!" What language. I will definitely be having a talk with her about how a lady behaves. Maybe I will have to give her a disciplinary spanking in the morning. Then I think, is that what Tom is going to do to me? Screw me. Is that why Teresa is using the butt plug in our sessions? And I think I might like it. So after Patrick went to work, Teresa and I went to the media room for our usual training session. But this time, I have a surprise for Teresa. I go ahead of Teresa. I have a pillowcase hidden in the room under a pillow on a chair. I pull it out and the neck to wrist harness. When she walks in, I am waiting behind the door. I quickly throw the pillowcase over her head, and push her onto the couch. She is caught totally off guard, and when her knees hit the couch, she bends forward, and falls onto the couch. I jump on top of her on the couch. She starts yelling, "What the fuck do you think you are doing? Get off me." She can't see because of the pillowcase over her head. Before she can recover, I get the harness buckled loosely around her neck. Then I grab her right wrist and get it behind her back and buckle it in. I repeat with the left arm. Then I get off her, and stand back to admire what I have done. I sit her up on the couch. I slide the pillowcase off her head. Now she can see, she starts up again. "Let me go now. I am going to punish you." I tell her to be quiet. "If you don't stop with that, I will gag you." And she responds by calling me a bitch. I take care of this by picking up the gag and start pushing it into her mouth. And she opens up to receive it willingly. After this, I tighten up the collar. I left it loose before to let me remove the pillowcase, but now it needs to be tightened, so she will feel what it is like to have your head immobilized in a collar, like I do every day. I get her up off the couch. She is standing in front of me. "Spread those legs." She obediently does. I walk around her. I like this. I can touch her anywhere I want. I squeeze her nipples. She squirms and wriggles, but I can tell she really likes it. Then I push her over the arm of the chair, and bend her over so I can grab her ass. She has a really nice ass. She likes to wear little when she trains me. As usual she was wearing panties and a corset. She also has on stockings, and high heels. She once told me that you should never walk around in stockings without shoes, as it is too easy to catch them and cause an expensive run. I pull her panties down, and insert her favorite vibrating butt plug. When I say favorite, I mean the favorite one she likes to insert in me. She squeals nicely. Next I pull up her panties, and sit her down in the chair, which I have come to know as the training chair. This pushes the plug a bit further up her ass and makes her squirm again. But I know all about the plug. I get stuffed with it every day by her. I also know how she will feel when I turn on the vibrator. It is so cool to see her eyes get big. I take a rope that I had hidden and tie it to the rear leg of the chair, through the ring on the back of the collar, and back to the other back leg of the chair. Now she can't get up. Lastly, I put on one of her training movies, and sit down on the arm of the chair to enjoy the show. Teresa is the show. I expected her to try to beg, but I don't get pleading eyes. She is enjoying this. She squirms and crosses her legs tightly. She once confessed she can get off by crossing her legs and squeezing. I don't know if it is true or just bragging. As I have indicated, she is competitive, just like a man, and sometimes exaggerates to be alpha male. But I am not taking chances. I use a bit more rope to tie her ankles to the legs of the chair. Now she is really immobilized with her legs spread. And I am going to take advantage of it. I turn on the butt plug, and then I touch her everywhere. I lift her breasts out of her corset so I can rub the nipples. I run my painted nails up the inside of her thighs and around her pussy. She squirms and moans into the gag. I tease her clitoris, and she is going wild. But I don't let her cum. I spend some time berating her for calling me a bitch. Then I discuss the bad language I heard before. All while teasing her cruelly. This is also making me hot. I start rubbing my penis, which is quite hard by now. I can't hold off much longer. I have one hand on her clitoris, and one on my penis. Suddenly, I feel her jerk as she orgasms. And a few moments later I cum. I get that post orgasm weakness. I flop into another chair. After a few minutes, I get up and remove her gag. I am not sure what to expect from her. What she says is "Please turn of the butt plug." I switch off the plug. Then I release her ankles and the ropes to her collar. After getting her up, I release the wrist restraints, and she removes the collar. Then we just hug. I say, "I think we are both going to have to shower and redo our makeup today." And adds "bitch". She liked it when I teased and lectured her. I will have to punish her again. I tell her that we will have to do our training sessions in future, before doing our makeup. The next morning, it is my turn for to be in the chair for training. Teresa teases me more this morning. I think it is sweet revenge. She made sure I was completely immobilized today. Then she teases me for even longer. The butt plug is driving me wild. I love the stimulation. I feel like I can almost cum from it alone. But I can't quite get there. I need her hand on my penis. But what an orgasm! All while watching videos of transvestites getting screwed in the ass, and giving blow jobs. This is really messing with my mind. I am getting turned on by the thought of getting butt fucked, and even the idea of a blow job is starting to sound good. I keep thinking what it would be like to be kneeling as a man holds my head, and forces his penis into my mouth. And all these fantasies involve me being in tight bondage. Her training is working. We get into a new pattern now. We are alternating with her being bound in the training chair one day, and me the next. John retires. The whole main office goes out for lunch. It is the usual speeches, and welcoming to Teresa as CEO. Later the software office goes out for dinner with John and Teresa and I. We go to a restaurant. We have reserved the whole place. It is quite an affair. None of these girls are in casual clothing. They all wear at least 4 inch heels. Even Ginny the office girl is in a suit with a short skirt with stiletto sandals. But they have another surprise. It is announced that Ginny will be taking my position as Teresa's assistant and a new girl Sarah will be taking Ginny's place on Monday. This is news to me. The weekend goes by. Patrick has to work on Saturday morning and plays golf on Sunday, so we have time to continue our "training". When she releases me, she has something new. She leaves the butt plug in and has me put on a tight panty girdle which holds it in place. Over the rest of the day, she occasionally turns on the vibrator in the plug. She seems to like doing it when I am not expecting it, and especially when I am standing up. It makes my knees weak. She loves watching me squirm. When Patrick returns after his golf game, he has no idea about what is going on, so I just have to deal with it. She lets me take it out when I can't take it anymore. I feel like I am going to explode. I follow it with a big shit. After this, I feel empty. I almost miss it. Monday, I take a taxi to the office. My office. I have been thinking about a few changes I want to make. First, no pants, except Fridays. And pants are only to be worn with the highest heels. No pantyhose, only stockings. And most importantly, corsets. About half the "girls" wear corsets. They need to. But I don't see why the ones who are skinny enough to get by without a corset should be more casual than those that are not so blessed. And they shouldn't be more comfortable than me. I have a slightly sadistic side, but I am sure they will all love it. Ok, they may not, but I am the boss now. The new girl Sarah is waiting for me. She is dressed in a tailored suit with a narrow corseted waist. Her pumps are very high. I figure she wants to make a good impression on the first day. I introduce myself. Then I see it as I look at her immaculately made up face. It is John. He retired from male CEO, and is now pretty office girl. This is going to be interesting. Clearly he is a submissive sort. I take him, oops; I should say "her" around the office and introduce her. Some of the girls recognize her, but most don't. I know they will all know by the first coffee break. I have her type out a notice of the new dress code and post it on the bulletin board. I also have her email it to everybody in the office. Several of the girls come to my office later to ask about the new rules. Some of them think they should not have to wear a corset. I explain how I believe that we should look professional in the office, and it is only fair that everybody has the same rules. They seem to accept this when I point out that I always follow those rules. Later in the day I get a package from the HR department. It contains my stock options. I read through the details. It is a standard package. Enough options that I will be rich enough to retire if the stock goes up at a modest rate, and quite rich if the stock goes up a lot. The only catch is the 5 year vesting period. I have to work here for 5 years to collect. Another 5 years as a girl. And I really can't say no. The problem is that if I went to some other job, I would be starting over from scratch, and I couldn't use this place as a reference. That is more money than I would ever earn if I were to start again at another job. Looks like I am going to be a girl for a long time. But it isn't bad. I have a pretty assistant, Sarah, who knows everything about the office to help me. And she is totally happy to fetch me coffee or do any other menial tasks. In fact, she seems to love it when I have her do stuff like that for me. I could have fun with this. It has been two weeks now, and things are going well. The office is running smoothly. Fortunately, I do have experience with software, and the girls in the office are easy to work with. And Sarah is fun. I have found that the more I degrade her, the happier she is. Yesterday, she was wearing a dress, and pumps with 2 inch heels. Quite professional in any office setting. But this is my office, not just any office. I called her to my private office, and close the door. I told her that I expect her to wear higher heels than that. I had her bend over my desk and I lifted up her skirt, and spanked her with a wooden ruler. I didn't really hurt her. Just a little stinging. Then I got out of my purse a butt plug and high rise open bottom girdle. I had been keeping them in my purse for a week, for just this reason. I told her to go to my private bathroom, and put in the plug, and put on the girdle. I also make her change into a pair of pumps I keep in my drawer. Of course they have 5 inch heels. I keep them as a spare in case I break a heel. They are close enough to the correct size for Sarah. I think they are maybe a bit small, but that will help her correct her ways. Sarah came out after a few minutes of struggling with the tight girdle. She is walking differently. She usually has a graceful swing to her hips. Now she is not as smooth. She is almost struggling. It is partly because of the heels, partly because of the butt plug, and partly because of the tight girdle. I love it. I find reasons for her to come into my office all day long. Bring me a coffee. Photocopy this file. I also make sure she is walking a lot. I send her out to a nearby sandwich shop for my lunch. I am sure all the boys love seeing her wiggling and clicking down the street. By the end of the day, I am completely horny from watching her. This just gets my creative juices running. I tell her we will be working late tonight at her house. My real reason for this is that I can keep her in her plug and heels longer. That evening we both arrive at her house. It is a large house, almost a mansion. She made lots of money from the company stocks. There is no pretence any more about work. As soon as we walk in, she starts to take off the pumps. I tell her, "You will stay in high heels until I tell you otherwise." I have her make me a drink. And then I get her to show me all her shoes. As I suspected, she has quite a collection of shoes. Mostly with high heels, and some with very high heels. I have her bring me a shopping bag and some masking tape. I put all the shoes without high heels in the shopping bag. I wrap the tape around the bag several times, and sign it in a few places. I say, "You will not wear low heels again without special permission from me. I will be inspecting this to make sure you have not opened it." Looking around her huge walk in closet, she has so many dresses. And at one end, I spot a leather dress. And then I see 4 maids' uniforms. They are all frilly with short skirts. Clearly these are not practical cleaning outfits. She says she does not have any cleaning staff. You can't have staff, and privacy. So she has to do her own housework. And the uniforms make it more fun. I ask what else she has. Sarah looks almost embarrassed as she opens drawers on one of her dressers, and they are filled with corsets, and bondage toys. There are collars, cuffs, gags of every type, and even a straightjacket. She is one kinky chick. She says "I just wish I had somebody to put me in these things." I respond, "Be careful what you wish for." I have her take off her dress. Then I remove the girdle but I leave in the butt plug. She was wearing a tight panty girdle under the girdle I had her wear. It is perfect for holding the butt plug in. I have her take off my pumps that she has been wearing all day. I can see lines in her skin, where they dug in. She thinks she is being released, but she is in for a surprise. I have her put on a pair of her shoes. A pick a pair of strappy sandals with very high heels. She looks hot. Next, I put a belt on her. It has a rings at the side attached to a set of leather manacles. I put her wrists in these. Her arms are now pinned beside her. She cannot escape. Also she cannot cover herself. Her bum is exposed for any type of punishment I want to issue. I add to this a ball gag. Then I have her kneel in front of her bed. I bend her over the bed and spank her. No pretence of this being a punishment for some behavior, just a plain spanking. After her bum has had enough, and she is moaning into the gag, I stop spanking and start playing with the plug. Most people think you have to pull it out and jam it in as if you were fucking, but in reality, all that is necessary is just a bit of jiggling on the bottom of the plug. And I can do this through her panty girdle. She is squirming a lot. Suddenly she thrusts a few times, and explodes. Cum is leaking through her panty girdle. She will have to do some laundry. She goes limp. I give her a few minutes. I want to grab myself and jerk off too, but I know if I do, I will lose my edge. So I control myself. Anyway, I would have to take off my skirt and tight panty girdle and garters to get to my cock. I remove her panty girdle and the corset she was wearing all day. I go through her drawers and find a Victorian looking corset, and a clean panty girdle. The corset is plain and white, but heavily boned. First I put the panty girdle on her, and get her tucked. I still don't like touching her boy parts. It takes me a while to get the corset on her, and laced up. There is something amazingly sexy about pulling the laces tight on a corset. And doing it on a helpless victim is even better. Now she looks just like a girl again. I take her downstairs. She can't say no, as she is still gagged. I order a pizza. While we wait for it, I spend some time on the couch with her. She is still bound, so I can run my nails all over her body. I love watching her squirm and wriggle. We must look a sight. Me torturing her in my blue suit with matching pumps with ankle straps and high, high heels, and her in a corset and high sandals and of course her bondage. When the pizza arrives, I answer the door and pay for it. The pizza delivery boy can't seem to look me in the face. He is either shy, or fascinated by my legs and heels, or maybe both. I take Sarah to the kitchen table, and remove her gag so she can eat. She begs me not to tease her any more. I have to feed her pizza and wine. I have to do this by hand. She still has her arms bound. Eventually it gets late, so I call a taxi to take me home. I release her hands from the cuffs before I go. The next day, a Friday, Sarah comes in wearing a pink suit, with matching high heels. She looks very cute and girly. Mid afternoon, I ask her for the project status report. I have her put this together every week, so I can make sure everything is on track. I notice that she has mixed up loose and lose. It is a common mistake in English grammar. Normally, I would not worry. But Sarah is a special case. I have her close and lock the door to my office. I love the look in her eyes. Fear, and anticipation. She knows what is going to happen. I have her lift her skirt and bend over my desk. But she has a surprise for me. She is wearing a tight panty girdle, and it is holding a butt plug in place. I pull the panty girdle down as far as I can. Her stockings get in the way, but they go far enough for me to get access to her plug. I was planning on giving her a spanking with a ruler. A ruler makes less noise than my hand. And I don't want to break a nail. But first I spend about 5 minutes playing with her butt plug. Then I spank her, then I play some more. I can tell she is about to come. So I stop. I stand her up, and pull up her panty girdle, and straighten out her skirt. Then I send her back to her on an errand to get me coffee. She is having trouble now. Her ass hurts from the spanking, and she is so horny she can barely walk. When she returns with my coffee, I send her back to her desk to correct the report. I really don't care about the error in the report. I just want her to sit at her desk on the plug, and then walk to the printer to get a new copy, and then bring it to me. I make sure I have lots of tasks for her that involve walking around for the rest of the afternoon. I am getting incredibly turned on by this. There is something about totally dominating a pretty girl that is amazing. And I have at least five more years of this. I love my job. Then I get a surprise. A text from Tom. He is back in town and wants to meet for a dinner tomorrow at a restaurant near our house. I panic. I call Teresa, who immediately drives over to see me. She tells me that I have to respond to his text. I reply and say I will be there. He replies with a time. What have I gotten myself into? Teresa drives me home. We talk. I am scared. I want to see Tom, but I am afraid, since I am not gay, at least I don't think I am. What if he tries to kiss me, or more? Teresa tells me that I will do fine. She says, "You have already kissed him, and liked it. Tomorrow, we can spend the day getting you ready for your date." "Date! Who said this is a date?" I reply. Teresa says, "Dinner at a restaurant. This is a date girl. You had better accept it." I spend the evening worrying. I want to go, but I don't. I like Tom, but I I am not gay. What will he wear? What should I wear? I start thinking about my dresses. Or should I wear pants. I don't want to appear too eager. No, a dress is better. Just not too slutty. But I should show some leg. Teresa, help! Teresa and Patrick have disappear into their room early tonight. I can hear sounds of a butt getting smacked, and Teresa begging, then silence. I bet she is on her knees with his penis filling her mouth. She loves that. I spend some time on the internet. I start looking at dating advice sites. I don't find much advice for crossdressers going on a reluctant date. I end up looking at fashion web sites. This does not help much, as I don't think I am going to be walking the red carpet of the Oscars. The next morning at breakfast, Teresa informs Patrick that we are going to be doing girl stuff all day. He decides to spend the day cycling with some friends. He will probably end up at a bar all afternoon with his drinking buds. I remember when I used to do boy stuff like that. I miss it too. Once he leaves, Teresa takes me for a "training session". But this time, she does not let me come. She comes. When she is done, she takes me to a shower, and gets in with me. This is to make sure I don't masturbate in the shower. She wants me horny all day. After we dress, we head off to the hair dressers. She made appointments last night when I told her about Tom. We spend a few hours getting waxing (ouch), manicures and pedicures eyebrow tweezing, and finally having our hair done. It costs a lot of money, but we have it now with our promotions. By the time we get home, it is late afternoon. And I am still horny. We drink some wine, and have a small snack. It does not look good to for a girl to scarf down a huge meal on a date. Lastly, we spend an hour trying on different dresses and shoes. Of course I end up changing my lingerie several times. It is a lot more complicated than it is for boys. This corset leaves a lump that shows under one dress. That panty girdle shows lines under another. The red dress is nice, but red is too much for a first date. The black dress has a slit that goes too high. I finally settle on a blue skirt and white blouse combination. The skirt ends above my knees, and is wide enough to be called "flirty". I match it with black strappy sandals with 4 inch heels. Teresa informed me that my heels are not high enough, so I put on my black strappy sandals with 5 inch heels. Then Teresa has me take off the blouse and skirt so she can do my makeup. I tell her I can do my own, but she is not having any of that. She does a wonderful job as always. But she adds some red lipstick. While I always wear lipstick, this is different. My lips are stained red, but she puts fire engine red long lasting lipstick on my lips. She says, "The long lasting lipstick will not rub off on a wine glass, or his lips." This doesn't help the butterflies that are happening in my stomach. When we are done, I put my blouse and skirt back on. I am careful not to get any makeup on the blouse. No spaghetti for dinner for me. When I look in the mirror, I realize, I look perfect. I am ready for my date. Teresa drives me to the restaurant and drops me off. She has to go and pick up Patrick, as he has been drinking all afternoon, and can't drive his car home. I go into the restaurant. I am very nervous. My stomach is doing circles, and I can't even think about eating. Tom is waiting at the bar. I walk over to him, carefully putting one foot in front of another to get a nice butt swing. This is where the flowing skirt really works. I can feel it flowing around my legs, and I know it looks good. Tom stands up as I get to him, and I put my arms around him and kiss him. At first, my head is swimming with the feeling of his lips, and his arms around me. But I realize, he is not kissing me back. At least not with any passion. When the kiss ends, he says, "Hi." That is it. Just Hi. He tells me he has a table reserved. So we walk to the table and get seated. We order drinks, and start small talk. I ask him about his business trip. He tells me about the work, and where he was staying. Finally he seems nervous when he says "I have some news for you. I didn't want to tell you over the phone. I met a girl while I was traveling. Her name is Linda. We have been seeing each other for a few weeks. We really hit it off, and just seemed to connect together. She is going to move in with me in a few weeks. I hope you are not too mad at me." I feel my face burning. I can hear the blood throbbing in my ears. But I remain cool. I tell him I am happy for him. He says, "I am so glad you understand. I am so happy with Linda. As soon as we met we knew there was chemistry. I can't wait for her to arrive. You have to meet her. I know you will like her." I don't really hear the rest of the conversation. I just want to run to the bathroom and cry, but I don't. I put on a brave face. I am glad for all the makeup. He can't see my cheeks burning red. I suppose I shouldn't be upset. We were never dating as such. I put more into this than I should have. And Teresa did not help with all the "training". I just assumed that Tom and I would be an item. I don't consider myself gay, so I should not be upset, but I am. I ordered the most expensive item on the menu. The surf and turf dinner. I know it is petty, but I think I deserve it. I know I won't eat much of it. I can never eat a large meal with a corset on. After dinner he takes me home. He kisses me on the cheek at the door and left. I go in. Patrick and Teresa are watching TV. Teresa took one look and said, "What's wrong?" At that, I let it all out. I tell them about Tom. All the time, my tears are ruining my makeup. Teresa and Patrick do everything they could to make me feel better. Thank goodness for friends. The next morning I wake up. A good night's sleep works wonders. I am feeling much better. I come downstairs to find Patrick cooking breakfast. I am not wearing a corset, so at least I can eat a meal. Teresa is still in a tight corset and high stilettos. Patrick looks at me and says, "I thought you were going to keep wearing corsets and heels until we you have had three dates with Tom." I object. "That won't happen now. Tom has a girlfriend." But Patrick replies, "The deal did not say anything about that. It just said that you and Teresa will wear corsets and heels until three dates are up. Teresa showed me the contract. And it reads, Girl Contract. This contract will be valid until I have had 3 dates with Tom. Until this time I will remain dressed as a girl. I will wear skirts and dresses a minimum of 5 days a week. I will only wear pants 2 days a week. My heels will be a minimum of 5 inches high. My waist will be laced to 25 inches except when I am bathing. My makeup will be perfect every day. I will watch movies and read material as directed by Teresa. I will act like a feminine girl. Signed Tina And Teresa's reads, Teresa's Contract. This