Tim Goes Undercover
By Moe
1) The Assignment
I picked up the phone and answered, “Accounting, Tim Bradley.”
It was my sister Tracee on the line and she said rather urgently, “I need to see you in my office. Something rather important has come up and I need your help.” My sister is eight years older than me at 30 and she is the president of our family company. She was working for our father who founded and ran the company when he suddenly died of a heart attack five years ago. Tracee was well qualified to take over the helm of the business since she was experienced in company operations and had an MBA degree from a well-known business school in the east. If there was any doubt of her capability, that went away when she more than doubled the company sales in the five years since she took over. The company is now owned equally by our mother, Tracee and me. In her grief, our mother decided to get away from everything and moved to the family vacation home in Barcelona, Spain shortly after father died.
“Tim, we are having a serious embezzlement problem within the company and so far I have not been able to determine where the drain is. I have already had a couple of outside audits performed but they could not find the source of the cash leak or any financial discrepancy” Tracee explained. “I am getting desperate to put a stop to this cash drain and find out who the culprit is. This situation needs to be resolved quickly. Having tried some conventional measures unsuccessfully, I am now ready to try something a little more unusual. I have been planning this for a couple of weeks and I need your help. You are family and so I can know I can trust you. Are you willing to help?”
What could I say but “Of course, whatever you need. I will be glad to help in any way I can.” Had I listened to her plan first, I might have reconsidered my response.
“Tim, I think we need someone to come into the office undercover that can observe the day to day business without raising any suspicion or alarms. The person doing this is not going to do something dumb in front of you or me. Since I need to continue to run the company, I would like you to go undercover and help find the culprit.”
“How can I go undercover; everyone knows me in the office? Besides, I am the VP of accounting and somebody needs to oversee the department,” I questioned.
“You are right of course and so we will need to disguise you so that no one knows who you are. As far as running the accounting department, I will assign Marsha to take over in your absence.”
“What kind of disguise could I possibly wear that would fool everyone in the office to thinking I was someone else?” I responded.
“That is why you need to become someone else who is totally different from the Tim they know. Tim is seen as a white, skinny, young man. If you came back as someone like that, it wouldn’t be long before someone figured out who you are. No, we need to make you over as a person who is completely different so that there can be no suspicion. So what is the opposite of a white, skinny, young man? Why of course it would be a curvy, middle-aged woman from Haiti. There would be no chance of anyone figuring out who you really are with a disguise like that.”
“Did I hear you right? You want me to go undercover and become a Haitian woman?” I was in shock and waited for Tracee to say that I misunderstood what she meant.
Instead, Tracee replied, “That’s right! Don’t you see? No one would pay any attention to a newly hired woman working in the accounting department. It would be perfect!”
“But … but I can’t. I can’t become a Haitian woman. I could never fool anyone into thinking that I was a Hispanic woman. I don’t know anything about being a woman let alone one from Haiti.” I was sure she could see that my arguments were strong and would change her plan.
“Don’t worry, Tim. I have been giving this a lot of thought this last week and I am convinced with the proper support and training, you will do great. I have already thought of everything and so over the next week and a half, you will undergo your transformation and learn how to be a convincing Haitian woman. My maid is from Haiti and she will help to train you after the physical transformation.”
I thought I could throw a wrench in her plans, “How do we explain my absence from the office during this undercover assignment?”
“No problem,” Tracee responded, “we will say that our mother is ill in Spain and that you are going there to be with her for as long as it takes. Tomorrow is Friday and you will not be coming into the office. Instead I will put out an office memo saying that you have flown to Spain and will be gone for an extended period of time to take care of our mother. Instead of coming to work tomorrow, you will begin your transformation process. I will pick you up at 6:30 am tomorrow and take you to the clinic so be ready to go. All the arrangements have been made with the clinic so we just need you to show up on time so you can become the new undercover accounts clerk. After the transformation and one week of training, you will come to the office on Monday a week and a half from now as the new accounts clerk.” It seems Tracee had thought of everything and I was committed.
My head was swirling with dozens of questions and I couldn’t believe that this was actually going to happen. My sister concluded, “I know you have lots of questions and concerns, but believe me I have everything covered. You know how thorough I am once I put a plan together so you really have nothing to worry about. See you tomorrow.” Easy for her to say I thought. I was dismissed from her office and went back to my own office with a million thoughts in my head.
2) The Transformation - Morning
I was waiting in front of my apartment building when Tracee pulled up right at 6:30 in her Lexus. I hopped into the passenger side and we took off. It took about twenty minutes to get to the clinic which was on the West side of town. The building was a fairly non-descript two story office building with no identifying name that I could see. We both got out of the car and walked through the front doors to the reception desk. Tracee stated, “We have an appointment with Dr. Knowles at 7.”
“Yes, we were expecting you and everything is ready. Are there any changes to the instructions you have given us previously relating to the transformation?”
“No.”
“Good then. I will let Dr. Knowles know that you are here.” After a couple of minutes, Dr. Knowles came walking down the hallway and into the lobby.
“Good morning, Ms. Bradley. I assume that this is Tim with you who will be going through the appearance reassignment process?” Dr. Knowles was a nice looking professional woman in a white lab coat and skirt who seemed to be close to forty.
“Hi Dr. Knowles. Yes, this is Tim. I want Tim’s appearance to be modified just as we discussed earlier this week. I understand that this will be a long day and so is it OK if I come back around 6:30 this evening?”
Dr. Knowles explained that everything was clear that had been requested for the transformation and that Tim should be ready that evening. I felt like a piece of meat since no one considered to talk to me and see if everything was fine with me. Apparently my opinions and concerns did not matter.
Tracee looked at me “Don’t worry about anything, it has all been arranged. Just enjoy the transformation and I am looking forward to seeing the new you tonight. Have fun!” To Dr. Knowles she turned and said, “Please take good care of Tim, he is the only brother I have.” With that, Tracee spun around and walked out the front entrance with her high-heels clicking on the hard floor.
“Follow me, Tim” and we walked down the hallway to Dr. Knowles office. “We need to take care of some paperwork and the billing before we can start the process. Please take a look at these consent forms and other documents and sign where indicated. Your sister has already reviewed and agreed to them so there shouldn’t be any problems. She also said you should put the bill on your credit card and then get reimbursed through a company expense report. She felt it would look strange to have our invoice billed directly to the company.”
I looked at the small stack of documents with lots of fine print legal mumbo-jumbo and decided to just sign them without looking at them too much since my sister had already reviewed and approved them. I gave Dr. Knowles my credit card and watched as she rang up the charge. “Now that the paperwork is out of the way, we are ready to start.” Dr. Knowles then picked up the phone, pushed a couple of buttons and asked the person at the other end to send Patricia in. A couple of minutes later, an attractive woman about my age walked into the office with a clipboard. Dr. Knowles introduced “Tim, this is Ms. Townsend. She will be taking care of you today through your journey in appearance reassignment. I will see you later today to perform a couple of very minor surgical modifications. Nothing to worry about, just enough to enhance the appearance results we are aiming for.”
Surgery? I didn’t know anything about there being any surgery involved. Before I could contemplate further, Ms. Townsend welcomed me, “Hi Tim, I am the technician and I will be with you all day as we transform you to the new you. You can call me Patty.” She reached out her hand to shake mine and then said, “Please, follow me.” I blindly followed her out the office door and down the hall. We entered a white tiled room with hard floors and populated with only a table and few chairs in the room. “Can you please take off all your clothes and put on this robe. There is no need to be embarrassed. I have done this many times before and like Dr. Knowles said, I will be with you through the entire process.”
I slowly stripped off all my clothes including my boxer shorts. “First let me quickly examine you to see what we have to work with and then you can put on the robe.” Despite her telling me not to be embarrassed, I couldn’t help being self-conscious as she looked me over head to toe. “Fortunately, there are no surprises and everything looks good. Please put on this robe and follow me to the next station.”
We walked out of the white tiled room and down the hall to another room with an entry door with ‘Hair Removal’ stenciled on it. “Are you going to remove my hair?” I stammered.
“Of course, women don’t have body hair,” Patty quickly replied. In the center of the room was a long shallow tub about a foot above the floor. Around the perimeter of the room were several stainless steel tanks and above the tub were large hoses connected to the tanks hanging down with nozzles. The tub itself was filled with about 6” of milky white liquid. Patty told me to climb into the tub and stay sitting up. Once I was in the tub, Patty handed me a snorkel-like device and told me to lie down completely and let the liquid immerse me all over. “Whatever you do, do not open your eyes,” Patty warned me. “You will be in here for about five minutes.” The liquid felt only slightly cool and the five minutes went by fairly quickly when I heard “Okay, you can sit up now but keep your eyes closed until I wipe your face off and shower.” I sat up, had my face wiped off and then Patty helped me out of the tub. Once I was standing up, Patty led me to a shower in the corner of the room that I had not noticed before. She turned on the shower water and it felt good to get the liquid washed off my body. That is, it felt good until I noticed that the shower water and drain had all kinds of hairs in it. I expected to see my arms and legs bare of hair but then it occurred to me that I had been totally submersed. My hands flew up to the top of my head and I could feel I was now bald. I couldn’t help but let out a loud groan.
“What happened to the hair on my head?” I almost yelled. Patty tried to comfort me that it would grow back eventually but it was a necessary part of the appearance reassignment process since I was getting the premium version of the transformation. Somehow, this did not comfort me at all but there was little I could do about it now. I dried himself off with a towel and put on the robe that Patty offered me.
“Come with me, Tim, to the next station,” which was in an adjacent room with another entry door just marked ‘Dye.’ Like the Hair Removal room, this room was similarly furnished with a shallow tub in the middle, stainless steel tanks along the edges and a shower area in the corner. Patty looked at the clipboard she held and then started filling the tub with a couple of the liquids from the tanks presumably with the right proportions. When the tub was filled to about 6” she topped the filling. “Like the hair removal we just did, you will again get in the tub and lie there for about five minutes. Do not open your eyes! I am going to apply a light coating of a grease on the palms of your hands and the bottom of your feet to reduce the dying process in those areas.” Patty helped me into the tub, handed me the snorkel device and I laid down again until I was completely submerged.
When the five minutes were up, Patty told me to sit up but keep my eyes closed until they could wash me off in the shower. She helped me out of the tub and guided me to the shower which was running. “Okay, you can open your eyes, Tim.” I opened my eyes and looked down. My formerly white body was now a nice light brown – all over. I was speechless at first but then finally thought that this was not too bad. When the excess dye had been washed off, Patty used a warm air blower attached to the wall with a 2” hose that she directed all over my body until I was dry. “We have to wait ten minutes to allow your skin to absorb the dye completely and you must remain standing so as not to disturb the results.”
“What happens next?” I asked.
Patty looked at her clipboard with the process instructions and informed me that we would have to repeat the complete dye process two more times. After the second dying I was a medium brown and after the third, I was a fairly dark brown. I could now see that I was truly becoming the color of a black person. It occurred to me that most Haitians a pretty dark skinned. I was glad that the dying process was over.
“Now the fun part begins! This is when we start to transform you from male to female,” Patty announced. She handed me the robe and we walked across the hall to another room with ‘Prosthetics’ clearly labeled on the door. She led me to the center of the room with a table covered with a thin cloth covered mattress. “Please lay down on the mattress face down and just relax. Your prosthetics will be here in just a minute” she told me.
Within two minutes, there was a knock on the door and two middle-aged female white-coated technicians walked in with a fairly large rolling cart. I could not see what was on the cart since it was covered with a white cloth. The two new technicians reviewed the clipboard that Patty held and then proceeded to begin their work. After putting on disposable gloves, they took a jar from the bottom shelf of the rolling tray, opened it up and then spread a layer of what looked like grease over my right buttock, hip, leg and inner and outer thighs above the knee. “This is very special bio-fusion adhesive that is used to adhere your new prosthetics to your skin so that they almost become a part of you and feel natural” one of the new technicians advised me. It didn’t mean much to me.
The cloth cover was removed from the top of the cart and I could see two large dark brown masses, two smaller ones and some others. I guessed these were the prosthetics. The second technician then took the jar of adhesive and began applying it to one surface of one of the large brown masses. When she was done, both technicians then gently lifted the large mass up from the cart and laid it carefully down on top of my right buttock and leg. The prosthetic was carefully positioned and then pressed down on to my skin covering my butt, my right hip and the back of my right leg almost down to the knee. The first thing I noticed was the weight of it. It must have weighed ten pounds or more. Medical gauze bandage was wrapped around my thigh I suppose to keep the prosthetic in place while the adhesive cured. Since I was lying face down, I couldn’t see much of anything. The process was repeated for my left side. I had no idea what I looked like now but it sure felt weird.
After waiting for what I guess was ten or fifteen minutes, the bandages were removed from my thighs and I was told I could sit up on the table. When I tried to sit up on the table, I couldn’t believe what had happened. I had at least 2” of padding covering my butt, hips and thighs. It felt strange to sit on the table with my new expanded butt. I felt and looked huge. Since the prosthetics matched my new skin tone fairly well, I had a hard time telling where my skin stopped and where the prosthetic took over.
“For the rest of the prosthetics application, we want you to lie down on the table face up” one of the tech women told me. I laid down as instructed on my new giant buttocks. It felt like I had a pillow under my rear. I did notice that in my little bit of moving around on the table that the prosthetics felt very natural when I moved my legs.
For the next part of the procedure, one of the technicians reached under the table and brought up and secured leg stirrups on each side of the table. I had not noticed them before. She then assisted me by putting one of my legs in each stirrup. I felt really vulnerable and imagined this must be how a woman feels at an ObGyn exam.
Like before, one of the techs took the jar of bio-fusion adhesive and slathered some all over my abdomen below the waist and on my genitals. At the same time, the other tech was doing the same on a brown prosthetic on the cart. When they were ready, the brown mass was gently brought over and set on my abdomen and they began work on putting my penis and testicles inside the prosthetic. When that was done to their satisfaction, they positioned the prosthetic carefully and applied pressure until the adhesive could start to hold. A water-filled pillow was laid on top of my abdomen and groin area to keep the pressure on until it was all secured. Since I was facing up, I was able to observe most of what was done and now knew I had what appeared to be female genitals. Patty kindly explained that since I was getting the premiere appearance reassignment, my pubic prosthetic actually had a ‘generous’ amount of black pubic hairs. I wasn’t sure if I should be grateful or not.
Looking at the cart, it wasn’t hard for me to figure out that the next step for me was to get boobs. Laying on the cart were what appeared to be two very large brown half cantaloupes. Seeing me eye my new boobs and knowing what comes next, Patty took the opportunity to talk about them. “These are not ordinary breast forms you will be getting. These breast prosthetics are more like a real women’s breasts and have a liquid-gel center. This means they will sag when you stand up, sag to the sides when you are on your back or hang down if you are on all fours. The size of the breasts is considered to be small ‘D’ size which is appropriate for a woman-to-be of your size and shape. Believe me when I tell you, you will not want to be without a bra after today.” That certainly is a strange thing for a man to hear.
It didn’t take long for the two technicians to install my new breasts on my chest. While I was waiting for the breast adhesive to set, I looked down at my new brown body. I now could see that I had two ample boobs, wide hips, a typical women’s abdominal belly below the waist and no penis. I was finally ready and told that I could sit up and then get off the table and stand up. I could feel my new boobs shifting on my chest as I changed position. When I finally stood up, I could not believe all the extra weight I was carrying. They told me all my prosthetics weighed a total of 33 pounds. That was a quarter of my body weight! I walked around the room a bit to get used to everything and surprisingly it was not too bad. There was no mirror in the room so I could not see what I truly looked like.
Patty handed me my robe since I was now a naked female at least below the neck. I thanked the two technicians as we left the room and Patty led me back to the Dye room. She told me one more ‘quick dip’ in the dye tub was needed so that the prosthetics color matched my new skin color exactly. Although the dip was only two minutes, I was now an even darker brown than before. I was amazed that I could not tell where the prosthetics were any longer since the transitions were now invisible. Walking around a bit, I could sense what Patty said to me about wearing a bra made sense even though I had never worn one before, of course.
3) The Transformation - Afternoon
Patty then informed me that it was lunch time and that we were about half done. We went to Patty’s small office and two lunch trays were delivered. “So what do you think so far?” she asked. I told her I had totally mixed up emotions and feelings about this but found the process fascinating. I was curious what I would look like when everything was done. It then hit me that I needed to pee after drinking the iced tea with lunch. Patty then said, “This would be a good time for me to teach you how a woman goes to the bathroom. With your new pubic prosthetic, you will need to do it sitting down like a woman does.” We walked down the hall a short way until we reached the ladies’ room. Patty stepped into the stall with me helped me through the process. As it turns out, it was pretty easy and I felt relieved.
Patty then told me it was time for the Cosmetic Surgery session. “This is where we do all the little things that make the results so perfect. We will be meeting Dr. Knowles again who is an absolute master at what she does. You won’t be disappointed.” I told her about my concerns about doing surgery and that I had not been forewarned that there would be some in this process. Patty tried to put my fears to rest saying it was all minor but important things as we walked down the hall. Finally, we reached a room where it said ‘Cosmetic Surgery’ on the door not surprisingly and entered. Patty called Dr. Knowles on the phone and told them we were ready. The room looked like a hospital operating room with a surgical table in the center and lots of cabinets, medical equipment and instruments around.
A few minutes later, Dr. Knowles came into the room. “Let’s see how you look. Open up your robe so I can check how you are doing.” I complied and she said I looked great, of course. “Please hop on table and lie down. My nurse will be giving you a light anesthetic to make you sleep and all the little surgeries we plan to do will be done with a local anesthetic. You won’t feel a thing and we should be done within an hour or so. I know you probably have lots of questions but everything we plan to do has been approved by your sister. We are a little pressed for time, so if we are going to be finished by the time your sister comes to pick you up, we really need to get started.” What could I say but okay?
When I woke up an hour later, I was not in any pain but some things just felt different. My nose, my lips, my ears, my eyes and my throat all felt strange and in some cases numb. I saw Patty standing nearby and asked “What happ . . . “ and couldn’t believe the sound of my voice. It was higher pitched, almost shrill, compared to what I was used to. I asked again, “What happened with the surgery?”
Patty replied, “Well I guess you’ve noticed your voice is different. Dr. Knowles made a small adjustment in your vocal cords to give you a more female voice as you can tell. She also enlarged your lips with Botox injections, flattened your noise by inserting metal bands in your nostrils and finally pierced your ears while she was at it. Afterwards, while you were still out, one of our staff cosmetologists gave you beautiful new eye lashes, eye brows and some long lasting makeup. You will get to see the ‘new’ you when we are done but believe me you are coming along fine. Since you are still naked under your robe, I think we should get you at least partially dressed so that you are decent. Please follow me, Tim. By the way, you certainly don’t look like a ‘Tim’ anymore. Do you know what your new identity is?”
It hadn’t occurred to me that I would need a new name and told Patty “I don’t know.”
“Well, I guess Tim it is for the time being then.” We walked down the hall and into a room labeled ‘Wardrobe.’ Inside the room were some open lockers with one identified as ‘Bradley’ where I could see there was some women’s clothes hanging as well as some small packages on a shelf. “Let’s start with these,” she said as she handed me a pair of white panties with some lace trim. They looked big until I remembered my new figure and they fit perfectly. I was then handed a long-line brassiere and shown how to put it on properly by Patty. I could see that my boobs felt much more comfortable being supported by the bra and understood why I should always be wearing one. I also noticed that I now had cleavage! The bra had four garters hanging from the waist that I was told to thread through my panties which I did. “Today you will be wearing stockings,” as she handed me a pair “but you can decide later on your own if you prefer stockings or pantyhose.” I was shown how to roll them up my legs and clip them to the garters hanging from my bra. It felt really weird to be thinking “my bra.”
Patty then removed a white full length slip from the locker, handed it to me and told me to put it on. I think this is when I first started to feel like a woman standing in my lingerie. “Now that you are ‘decent’, let’s head to the next station which is Cosmetology. This is where the miracle happens that makes you look truly female. Follow me.” So once again we walked down the hallway to the Cosmetology room. Inside were three beautician’s chairs and counters behind the chairs stocked with makeup item that could possibly be needed. I looked for mirrors but there were none on the walls.
I was told to sit in the center chair and that Sherry would be handling this stage of the process. Sherry introduced herself and said, “First we will be doing your makeup, then manicure, pedicure and nails and then finally your new wig. When you leave here, you will be a woman as far as anyone can tell. I think you will be truly amazed when we are done. Most women enjoy going to a beauty shop so please relax and enjoy the next hour or two.” Sherry had an assistant doing the manicure and pedicure while she did the rest. She was right and I found it very relaxing and enjoyable to be sitting there while they worked on me. The most exciting part was when they put my new black haired wig on me with more bio-fusion adhesive and styled it. I knew the transformation must be almost done.
Sherry announced that she was finished and invited me to come to the back room where they had a full length mirror. I couldn’t believe what I saw. I looked like a reasonably attractive older black woman from Haiti without any hint of being a man underneath. My body had a woman’s shape with large hips and butt, big boobs and a well made-up female face. I couldn’t tell I was a man and so I couldn’t see how anyone else could either unless I did something stupid.
Patty genuinely complimented me on how I looked and suggested that we should go back to Wardrobe to finish getting dressed. My sister would be here within an hour and we needed to be ready she informed me. Back in the dressing room, Patty took a sheer white lacy-front blouse out of the locker and handed it to me to put on. I had some difficulty with the reverse buttons but managed. I could see a hint of my slip and bra straps through the blouse in contrast to my dark skin. Hanging in the locker was a grey Glen Plaid women’s skirt suit. Patty removed the suit from the locker and handed me the skirt to put on. She instructed me to spin the skirt around so the zipper was in back and then reach underneath and pull my slip down firmly to smooth it out.
At the bottom of the locker were a pair of grey shoes which Patty retrieved and handed to me. “A woman sits down and crosses her legs to put on her shoes” I was told. So I sat down on a nearby chair, crossed my legs and put on one shoe, re-crossed my legs and put on the other shoe. It was a new experience to cross my legs with stockings on which I enjoyed. “These are 2” pumps so you really shouldn’t have much difficulty getting used to walking in them,” according to Patty. I stood up and walked around a bit and I thought I did pretty good. “You are walking like a man! You need to learn to take smaller steps and sway your hips when you walk. You are a woman now!” I practiced walking for a while under Patty’s supervision until she said I was doing pretty good but I should practice more later.
Finally, I was given the jacket to put on which fit perfectly. It was clear these people knew what they were doing. “We are almost there,” Patty announced, “but no woman is fully dressed without the accessories.” I was then handed a woman’s watch, two bracelets, a necklace and a grey purse with shoulder strap. Once these were all in place, Patty led me to the back of the room where there was a full-length mirror facing the wall. She turned it around and I could see myself as an office woman for the first time.
“If I didn’t know it was me, I wouldn’t believe it,” I said to Patty.
“Let’s go to Dr. Knowles office. We have a little time before your sister gets here and we can answer some of your questions and tell you what you need to do and not do now that you are transformed.” I had lots of questions and it seemed like their answers were somewhat evasive and I was often told to talk to Tracee. There weren’t really any significant restraints now as to what I could do and I was just told to enjoy living as a woman.
The phone rang and Dr. Knowles answered it, talked a bit and then announced “Tracee is in the lobby. Let’s go down and introduce her to the new Tim.”
4) The Training
As the three of us walked down hallway towards the lobby, I could see Tracee and another woman sitting in chairs waiting for us. When Tracee heard us coming, she looked our way and I could see she was startled when she put her hand to her mouth. She tried to hide her surprise but it was too late. We arrived at the lobby and Tracee exclaimed, “My God, Tim, is that you?” All I could say was that it was me. “Open up your jacket and let me get a look. Wow! Let me hug you, you look great!” We hugged each other tightly. It felt different to hug another woman now that I had boobs. After a long hug, she said, “I never thought my little brother would have bigger boobs than me. Please excuse my manners, let me introduce you to my home helper, Fabiola Dalisma.”
Fabiola rose from her chair and shook hands with me, Dr. Knowles and Patty. She was a woman in her forties I guessed and even darker skinned than me. She was nicely dressed in slacks and a blouse with a neat and trim appearance. Tracee announced that Fabiola had been helping with some of the preparations for my transition, arranged for new living quarters and would be helping to train Tim in his new role as a Haitian woman. I had seen Fabiola a couple of times before at Tracee’s house where she served mainly as a cleaning lady. Since she wore a grey uniform, maybe she was considered a maid.
After thanking the staff for all the good work they had done, we received a package with my male belongings and then Tracee, Fabiola and I walked out the front door to her car. I quickly figured out how to get into a car wearing a skirt. I looked over at Tracee in the driver’s seat and noticed that we were both wearing grey skirt suits. How often does an adult brother and sister get to dress alike?”
Tracee said, “I have made reservations at a restaurant so we can discuss what the next steps will be and so you two can get better acquainted. By the way, you will be living with Fabiola in your new two-bedroom apartment so that you can get full time training.” The surprises never seemed to end. We arrived at the restaurant in about twenty-five minutes, went inside and got a table in a corner circular booth with me in the middle. We ordered a bottle of wine and after it was served, we all toasted to the ‘new woman’ in the group. While eating dinner, Tracee explained all the preparations that had been done including getting a new Social Security card and birth certificate, leasing a new apartment and so on. I was told my new name was Roseline Moliere and that I was now 38 years old. In a way, I went from younger brother to older sister in one day.
I asked Tracee how long she thought I would remain disguised as Roseline. “I think this will be a fairly difficult investigation and so I am guessing at least four or five weeks. That is why I wanted you to get the premiere level of transformation with longer lasting results. When we are done, we can then reverse your transformation and you can be Tim again.” It was a longer duration than I had expected but I was relieved to hear that I would be Tim again.
“I think it is time to see your new apartment, Ti . . ., I mean Roseline.” After the bill was paid, we headed back to the car and drove to a ‘working class’ neighborhood. We parked in front of a hardware store that was closed for the evening and entered the building through a private entrance locked door, walked up a flight of steps and down a short hall to another door. Unlocking the door, we all entered the apartment.
The apartment was small, clean and furnished with older but functional furniture. There were two bedrooms and Fabiola had already established herself in the smaller of the two. The unit also had only one bathroom, a living room and a kitchenette. I went into my new bedroom and could see it was spartanly furnished with a full-size bed, dresser, small vanity with mirror and a nightstand. In the corner was a medium sized closet with a few women’s clothes hanging inside I could see.
Tracee told Fabiola and me that the next few days, in addition to full-time Haitian woman training, that I needed to get a wardrobe of clothes for both business and casual wear, get a photo ID, get checking and savings accounts, get bus passes and all the other stuff that normal people have. “I have set up a job interview for you next Wednesday morning at the company. This is obviously for appearance sake but you still need to do a good job which I am sure you will do. I do not want to tell HR what we are doing since the less people that know the better. However, I will inform Marsha who will be taking over for you in accounting since you will be working for her.”
Everything Tracee said sounded reasonable and well planned which is not surprising for her but I still was apprehensive about it all. As Tracee was getting ready to leave for the evening, she suggested to Fabiola that we should spend the Saturday shopping for clothes. However, she warned us not to go to Nordstrom’s or like place but rather to a JC Penney’s where real working women might go.
After Tracee left, I sat in the living room with Fabiola and talked with her for a while. I found her to be a smart woman with a broad background in a lot of subjects. When it was time to go to bed, she helped me find a nightgown in my dresser. She was going to show me how to take my makeup off and we found out that most of it was permanent and would not come off. At least the good news she said is it would be much easier in the morning to get ready to go out. I was thinking how long is permanent?
The next day after a quick breakfast in the apartment, Fabiola and I were planning to go to the mall. Since I had a limited wardrobe, I put on the only casual dress in the closet that I had over the same lingerie I wore home yesterday with clean panties of course. Since we don’t have a car, I learned we would be very frequent users of the city bus system and would take a bus to the mall. In fact, one of the reasons our apartment was selected is because of the easy access to a lot of bus routes including to the company office and Tracee’s home. Although I knew I absolutely looked like a woman, I was still a bit scared to step outside our apartment building and walk down to the bus stop in a dress. The bus arrived within five minutes and I followed Fabiola on board and we found a seat together.
When we arrived at the mall, Fabiola suggested we first shop for undergarments at her favorite lingerie store. Fabiola found a sales clerk in the store that she knew so that I could get professionally fitted for bras. It was quite an experience to have another woman help me put on all kinds of assorted bras and then feel, poke, prod and push my boobs to make sure the bra was fitted correctly. In the end we bought three longline bras and three regular bras that I was told fit properly. In addition, we also got a dozen panties in various colors and styles, half-slips and full-slips. To learn whether I would like pantyhose or stockings better we bought a few pairs of each so I could try out both. Who knew I would be doing a pantyhose test to see if I liked wearing them or not?
When the lingerie shopping was done, we went to a couple of women’s clothing stores. Fabiola reminded me that whatever we purchase would have to be carried home on the bus so we just should get enough for the next week or so. With that in mind, I tried on lots of clothes and ended up with a skirt suit, a pantsuit, a couple of skirts, blouses, casual pants and a couple of tops. It was nice shopping using Tracee’s credit card. We ate lunch at the mall and then brought home all our purchases with some difficulty on the bus. Once back at the apartment, the clothes were hung up in the closet or put away in the dresser.
That night we went out to a neighborhood restaurant and bar and had a great meal and I got to know more about Fabiola and her Haitian culture. My background story was that I was born in the States and had never been to Haiti so I would have an explanation for not knowing the language or details of Haiti but I still needed to know something. In the days that followed I learned a lot more than I ever thought I would about Haiti. In addition to more shopping, we opened up a checking and savings account, got a state ID card, got a cell phone and even a frequent shopper's card at the local food store. Roseline Moliere was becoming an official member of society. Surprisingly, I was becoming more comfortable in my new role as a Haitian woman and felt that Fabiola was a true friend.
When Wednesday came, it was time for me to get ready for my job interview with my own company. I put on my new light blue skirt suit and blue blouse for the interview and thought I looked very professional and Fabiola agreed. I took a city bus to the office which was a straight route but I still had to walk the final two blocks. Fabiola advised me to wear flat shoes while going to the office and then put on my high heels that I had carried in a bag once I had arrived. I now understood why a lot of office women did this. I told the receptionist who I was and that I had an appointment to meet with Karen in HR. I was told to take a seat and that Karen would be out shortly.
About five minutes later, Karen came out, greeted me and we shook hands. “Please follow me to my office and then we can get started,” which I did. It was strange to walk through my old office area dressed as a woman but clearly no one ever came close to recognizing me. I could sense that this disguise would work. It was a typical job interview with discussion about the company and the job and then wanting to know more about me and my background which all went smoothly. I was then asked to fill out some employee documents and background information. Karen told me that since I was recommended for the position by Tracee, it should be pretty smooth sailing.
Karen then informed me that I would be meeting with my new boss, Marsha, next. She put in a call to Marsha’s office and told her that we would be coming over to meet her. I couldn’t believe it when we walked over to my old office and there was ‘Marsha Graves’ name on the door with VP, Accounting underneath. Karen knocked on the door and then we entered. Karen introduced me to Marsha and explained that I was the candidate for the accounts clerk. Since Marsha had previously worked for me I knew her quite well. She was an attractive single lady in her early thirties. If I had been ten years older, I would have considered asking her out myself. Marsha thanked Karen and then suggested to me that since it was 11:30, that we should go out to lunch. We went down to the building entrance, hailed a taxi and took a short ride to a nice restaurant nearby. We made small talk along the way.
Once we were comfortably seated and had order a couple of iced teas, Marsha finally said, “I am amazed, I can’t believe that is you, Tim. If Tracee hadn’t told me, there is no way I could have guessed that it was you. Again, you look amazing and very natural.”
“Thank you,” was all I could say. This was the first person besides Tracee and Fabiola that knew who I was and I was in a bit of discomfort.
“Don’t worry, your secret will be safe with me. Tracee told me why you’re doing this and so I plan to give you a lot of freedom while you are in the accounts payable/receivable clerk position. This will be a good place to do your investigative work from. If you ever need anything from me, just let me know.” From there, Marsha went on talking about my transformation and how good I looked, how nicely I was dressed in my skirt suit, my makeup, hair, nails and on and on. When lunch was finally over, we returned to the office and I was dropped back off at the HR office to complete the interview process. I was told that I should hear from them in a day or two about the job. I took the bus back to the apartment where Fabiola was waiting and I told her everything that happened.
The next day around mid-morning I received a call from Karen congratulating me on getting the job. I tried to pretend that I was surprised and happy to get the job and looked forward to starting work the following Monday. The rest of the week was spent doing more shopping and errands to get me the items I would need to be the complete Roseline.
Fabiola then explained to me that when I went to the office, she would be returning to her duties as my sister’s cleaning woman as well as for others. Of course, we would continue to be roommates at the apartment. However, since it was not appropriate for President Tracee to meet with a lowly office clerk Roseline while at the office, she would want to meet me on Saturdays to get updates on the investigation. The best thing was for me to travel to Tracee’s with Fabiola dressed like her in a cleaning woman’s maid uniform so as not to arouse suspicion. I thought this was too much but nevertheless ended up going to a uniform shop and getting completely outfitted in a maid’s uniform just like Fabiola’s from the cap down to the shoes.
5) The Office
Monday morning finally rolled around and I thought I should look good on my first day of work as Roseline. I decided to wear the grey skirt suit, lacy-front white blouse with matching shoes and purse. Even after a week of dressing as a woman, I still couldn’t believe all the sensations I felt just going to work on the bus and walking to the office. I could feel my breasts moving up and down my chest against the constraints of my bra. I could feel the tug of the stockings on my garters as I walked along. The feel of my stockinged thighs rubbing against each other under my nylon slip. The feel of my smooth, silky blouse on my shoulders and arms and just the way my women’s clothes felt in general. Even the soft breeze under my skirt felt wonderful. Just carrying a purse over my shoulder made me feel very womanly. I never felt anything like this when I wore a suit to work as Tim.
When I arrived at the office, I went to Karen’s office to get in boarded with all the final paperwork, employee key card, personal computer information and so on. When everything was done, Karen walked me over to my old office where Marsha was waiting. She greeted me warmly, told me how nice I looked and then walked me over to my new work cubicle and said this is where I will be working. After Karen had left, Marsha told me that since I already knew all the procedures of the accounting department, I could just get to work. On the desk was a laptop computer, a monitor and a few company binders.
When I logged into the office computer as Roseline, I could see I had restricted access to accounting records. When I tried to log in as Tim Bradley, I saw that that name did not exist in the computer network. I would definitely have to talk to Tracee about this. I knew that I could not do anything about this during the work week but when we would meet on Saturday. I was given a small stack of accounts payables documents that needed to be processed and managed to take care of them quickly. I decided I would need an approach to conduct my investigation. Since it seemed likely any fraudulent money leaving the company would be through accounts payable, I decided I would concentrate in that area. I knew that for each transaction, I would need to look at the requisition, original purchase order, incoming freight documents and bill of lading, outgoing freight documents and invoice. Considering the number of transactions that occurred each month, I began to wonder whether four or five weeks would be enough time.
One pleasant surprise was how nicely I was accepted by the ‘other’ women in the office. They made me feel very welcome and I regularly went to lunch with them either in the lounge area or out to lunch. I especially became good friends with Kate and Janet and we even stopped after work a couple times for drinks. By the end of the first week, I had become used to the routine of going to the office and working and it frankly went better than I had expected. However, I never got over the sensuous feelings from being dressed as a woman. Every time I moved around, I could feel my breasts shifting in my bra. When I bent over to get a file out of a drawer, I felt the garters pull on the welts of my stockings. If I went to get a coffee in the lounge, I heard the click-click-click of my high heels on the hard floor. There were lots of constant sensual reminders that never let me forget how I was dressed. Surprisingly, even when I wore my Salmon colored pantsuit to work on Thursday, I felt very feminine probably because of my long-line bra and pantyhose I wore underneath and a silk blouse.
Today is Saturday and the first time I would have a chance to meet and talk with Tracee since she picked me up a week ago from the facility. Fabiola and I both got dressed in our white stockings, maid’s uniforms and white work shoes. We each packed a small carry bag to hold our apron, maid’s cap, extra shoes, rubber gloves, knee pads and so on. We walked to the bus stop and after a short wait got on the same bus line I usually took to work. However, instead of getting off at the usual stop, we took the bus to the end of the line which was in a suburban village center. From here we had to walk three blocks to Tracee’s beautiful, large home in a nearby subdivision carrying our bags and purses. Fabiola rang the doorbell and then just stepped inside as she usually did since she was expected. It was about 9:30 am, her usual time.
We were in the foyer when Tracee noticed us. She was with Marsha and George Brown of sales in the living room in the midst of a discussion. “Oh, the cleaning ladies are here. Excuse me, I need to speak with the girls for just a minute,” and then Tracee walked over to us. “I am sorry about this. I had no idea George would be here and we have a serious matter to take care of,” she said in a low voice. “Fabiola, can you please take Roseline with you and start your usual cleaning work. You can show her what to do,” she said looking at me. “It’s important that George think you are both here to clean.” With that she turned around and went back to Marsha and George.
Fabiola led me to the kitchen and said, “You heard Tracee, we both must do cleaning so you will work with me. I will show you how to do a good job of cleaning.” We opened our carry bags and put on our aprons and maid’s caps. “Let’s start with the master bedroom” and we walked down the hallway. We stripped the king-size bed down and then put fresh bed linens on and re-made the bed so that it looked perfect. We gathered up the old linens and took them to the laundry room and started the wash cycle. Returning to the master bedroom, we picked up any clothing that was lying around and hung it up in the giant walk-in closet. We dusted and wiped all the furniture so that it was clean and shiny, vacuumed the floor and then organized the makeup items neatly on the vanity. Instead of finding the work demeaning, I liked the idea of making things better and took a bit of pride in our work. I think Fabiola could sense this too and appreciated it.
Next was the ensuite bathroom that needed to be cleaned. I scrubbed the toilet and bathtub while kneeling in my knee-pads while Fabiola cleaned the tile walls. We went on to clean two more bedrooms, two more bathrooms and we were just starting in the kitchen when we heard Tracee call out, “Oh, girls. Could you come here please?” We dropped our cleaning rags, took off our rubber gloves and dutifully marched into the living room and ended up standing side-by-side like a couple of soldiers waiting for our orders. “Our meeting has run longer than I expected. Could you make us some sandwiches and bring in some cold drinks for my guests?”
We then returned to the kitchen where Fabiola began making sandwiches. I got two pitchers out and filled one with iced tea and in the other I made iced lemon water. When we were ready, we both walked out with me carrying the two pitchers. I asked each person what they would like and then filled their glass while Fabiola served the sandwiches. After everyone had what they wanted, we returned to the kitchen to finish cleaning it.
About an hour later Marsha and George left and so we were alone with Tracee. “I am sorry about what happened this morning but it couldn’t be helped. You both did a good job at cleaning and George I am sure has no suspicions at all about you being here, Roseline. Fabiola, can you finish cleaning the living room while I talk to Roseline?” I spent about a half an hour telling Tracee about my planned approach to the investigation and mentioned that it might actually take longer than she had expected. “That’s not a problem.”
When we were done, Tracee walked around the house to check our work I assumed and surprised me when she said, “You girls have done an excellent job cleaning.” She turned to Fabiola, “Would you mind if Roseline helps you every Saturday? I will pay both of you of course.”
“I would like that very much but it is up to Roseline,” Fabiola replied.
“I suppose that would be okay with me,” I said somewhat reservedly. Tracee went to her bedroom and came back a couple of minutes later with two envelopes and handed us each one. I think I have just become one of my sister’s cleaning ladies.
I must say that I enjoy going to the office more than when I was Tim. I really enjoy my camaraderie with the other girls in the office, the rather light and easy work load and frankly, the constant sensual stimulation I feel all day long dressed as a woman. I have been at this for six weeks and I was making no progress in my investigation. If someone was embezzling money out of the company, I felt I was no closer to finding that person than the day I started.
6) The Reveal
It was another Saturday morning at Tracee’s house and Fabiola and I had just finished all the cleaning and laundry. In addition, we had been asked to wash and clean all the windows so it had been a long morning. Tracee told Fabiola that she should go home but that I needed to stay around for a while since Marsha was coming over and we needed to have a discussion about the office. Fabiola was tired and so she was happy to go home.
Marsha arrived a short while later and so we all sat in the living room with cold drinks that I had made and served. After all, I was still a maid.
Tracee started out by saying, “I have to admit that I have not been truthful with you, Tim. First of all, I think that you will agree that Marsha is more qualified and experienced to be the VP of Accounting than you are. She has more than ten years of experience and an MBA where you just graduated from college less than a year ago. It makes no real sense that she should be working for you. Second, Marsha and I have been in a relationship for almost a year now and she will be moving into this house in the next week or two. I wanted Marsha to have your position in the company which she deserves. The problem was how to get you out of that position. Since you are a company owner, I cannot fire you or lay you off. Therefore, we devised this plan where you would willingly give up your position. The truth is there was never any embezzlement from the company and no investigation was needed.
“The second area where I was not truthful is in your transformation. I told you that when the investigation was completed, all of the transformation could be reversed and you could come back as Tim. I have to inform you that all the changes done at the transformation facility were not just temporary but are, in fact, permanent. The documents you signed that morning stated that you consented to these permanent changes. This means your skin will always be dark brown. The prosthetics are bonded to your skin and it would take major surgery to remove them. The cosmetic changes that were done to your face were done with permanent makeup similar to a tattoo. In reality, there is no going back to being Tim.
“All of your physical assets such as your car and furniture have been sold and your apartment lease terminated. The proceeds of the sale of your assets were put into an account under Roseline Moliere’s name. Your savings and checking accounts, investment accounts and any other financial assets were all transferred over to these same new accounts. We did save any personal items and packed them into a couple of boxes that you can have.”
I just sat there listening and I was stunned at what I was hearing. Finally, I asked, “What about my share of the company?” not knowing what else to say.
Tracee continued, “With Marsha’s help we had the company charter amended. Tim Bradley’s name was removed as a company owner and replaced with Roseline Moliere. I am not out to take away your rightful share of the company. I told our mother that this is what you wanted and so she willingly signed the amended charter along with me which represents two-thirds of the ownership and so it is legal. What this means is if you ever decide you want to be Tim Bradley again, you will lose all your personal financial assets and your share of the family company.”
My head was reeling. How could my own sister do this to me?
“I am sorry I did this to you and I sincerely apologize. On the other hand, I have never seen you so happy and contented as you were these last six weeks while you were Roseline. You must admit that there was a lot that you liked about being Roseline. I could see it in your dark brown face.”
I had to admit that there was some truth in what Tracee said although I hadn’t thought about it before. I did like a lot of things about living the life of a woman.
“When we created the extra position in the accounting office for you, we really didn’t need an extra girl in the department. However, business has picked up enough so that we would like you to continue in your accounting clerk position three days a week and with full benefits. I have already spoken to Fabiola and she said she would love to have you work with her as a cleaning lady when you are not in the office.”
I didn’t see what choice I had but to continue being Roseline since I wasn’t willing to lose everything. Besides being a black Haitian woman wasn’t so bad since I had a good friend in Fabiola and good office co-workers at the office. I really did like living as a woman. I told Tracee that “I will be Roseline from now on.”
The End