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So I had cross dressed my entire life. One of my earliest memories was stealing my mom's nylons and pulling them on. I don't know why but I loved the way they felt. As I got older and moved out I was able to dress in the seclusion of my home. It was not a daily or even monthly thing but it was something I did. Don't get me wrong, I never wanted to become a woman. I just liked looking liked one, feeling the caress of the dress and hose, and yes I got sexual pleasure from it. I would dress, masturbate, and then force myself to stay dressed until the shame dissipated. Most cross dressers immediately take off the clothing and vow that it is not going to happen again. For me I felt that I almost needed to punish myself for doing it and forcing myself to stay feminine after the desire passed made strange sense. The result of the practice is that over time the shame seemed to go away faster and faster until it just was gone completely. I got my pleasure and then just expected that I was dressing this way for the day. It created a normality to it. Another different thing about me was my preferred style of dress. Sure I had toyed with short skirts and even some sissy little girl dresses but what I really enjoyed was dressing as an older woman. At 35 I looked like a normal guy, a little short at 5'6", and had some pudge but normal for someone my age. When dressed I liked to look like a 60 year old woman. I wore a gray wig and called myself Mildred or Millie. All my dresses and skirts fell below the knee, most ankle length. Thrift stores in retirement areas were a great place to find beautiful long dresses with lace collars and wonderful lingerie from forgotten eras. Full girdles and heavy support bras were my favorite. Sometimes I wore stockings but I loved support hose. I don't know why being an old woman appealed but it was a way to get release and relax. I dated like most men and even was married for 5 years in my 20s, but we just grew apart. I never told her about my fetish but I think she knew, most men don't shave their bodies and watch Golden Girls like did. I worked for an advertising firm in production in Seattle. The job was easy. Most of my time was spent on my computers editing clips. My life was boring. Get up take the Metro to Federal way. Work from 8 to 4. Head to my apartment. Sometimes I would meet up with guys from the office for a beer after but not that regularly. Some weekends I would just sit and read or play on my computer and others Millie would clean the place then have her tea and watch her shows or crochet. In January the virus hit. We were all called into the conference room on a Friday. Ben Andrews, the 65 year old CEO, had us gathered to talk about how the company was going remote. He explained how the work load would be shifted to on-line platforms. It was discussed who would do what. At one point he looked at me. "David, from now on your duties will fall solely on editing. Your other duties will be reassigned. I will only be paying for one person to have the computers and equipment moved to their house and that is you. Do you understand young man?" I nodded and then he moved on. As the meeting was breaking he stopped me again. "I will expect daily updates and at times may need to come to your place to review products. I hope this won't be a problem." I knew he was being polite. If wanted my job I was going to comply. A week later the corner of my living room had a desk with four monitors and multiple computers. I wasn't sure I was going to like this but it was what it was. My days became mundane again. Up coffee, sit at the desk, edit, lunch, phone calls, video chats with Mr. Andrews, dinner, bed and then start all over again. By the end of February the routine had caused another change. Millie was no longer just occasional. I needed relief from never getting to leave work and being Millie gave me that. Every weekend I rose and preformed the ritual of becoming an elderly lady. I did David's laundry, cleaned his desk and put things together for his week. At some point, I don't know when, I was living two lives. I was two people. 35 year old man during the week and 60 year old woman on the weekends. This worked well until the end of March. By then we expected to be back at work but the virus was going crazy and there was no end in sight. The projects became more in-depth and intensive. I spent more and more time on the computer and was feeling the stress. It was Saturday morning. I was sitting by the window drinking tea rubbing my feet together. I dearly loved how the hose felt on my legs. Looking down at my dress I felt a surge of happiness. It was nothing special, just a light blue floral house dress but it was comfortable and was how I needed to be. I got up to go the bathroom an started the difficult part of pulling down the support hose and then feeding my little penis through the opening in my girdle, holding my dress out of the way I settled down to pee. As I did this a portion of my gray wig fell into my eyes. Absent mindedly I brushed it away. A thought occurred to me. Why am I still wearing a wig? Standing in front of the mirror I pulled it off and let my hair out of the wig cap I was wearing. My brown hair came free. I brushed it out and realized the over the last few months my once chin length hipster look had grown down almost my shoulders. I could actually style it into a woman's style. The color was all wrong but I could change that. True I had never bleached my hair or colored it but even if it didn't work out no was going to see. The thought of having my own gray silver hair was mesmerizing. I wanted to do it, no I needed to do it. An hour later my phone pinged that the order from Walgreens was outside for me to retrieve. There was three different boxes, one was bleach, the other silver dye and finally a set of curlers. My hands were shaking as I read the instructions. It was not difficult as I thought it was going to be. Wash my hair well then while wet, I pulled the hair into sections and combed the sulfur smelling solution through the strands. With a towel over my shoulders I sat with my tea and waited. When my kitchen timer went off I hurried to the sink and began washing again. There in the mirror I saw wet white and yellow hair on my head. While thrilling it was not quite right. Once again I was combing a gel in, this time it was a purplish blue. Back to the easy chair with my towel over my shoulders. The timer dinged again. This time I was presented with beautiful silver hair with just a slight blue tinge, I was a blue hair, I laughed. Methodically, using a website as a guide I began to tightly roll my hair into the bristles of the curlers. A pink plastic pin held them in place. It took about an hour but finally had neat tight rows of curlers. I put a plastic cap over them and went to make dinner. While cleaning the chicken breasts I was going to bake, the tightness of the curlers was constantly reminding of what I had done. More than once a shudder would pass through me as I would have a small orgasm just thinking about it. Thankfully I had used a pad that day. A 9pm I went to my bedroom and started to undress. With my hair still tightly up I took off my hose and girdle. Slipping on full coverage panties and new pad I settled a long flannel night gown over myself. I couldn't wait for the morning to take the curlers out. Sleeping in bristled curlers is not comfortable. That and my excitement kept me from sleeping well, but finally the sun came up and it was Sunday morning. My entire was body tingling with trepidation, but I forced myself to take my time. I showered in the plastic cap. Made sure to shave well, put on my foundation garments, a new pair of support hose in nude. I selected a high collar burgundy dress with a full skirt. Dressed it was time to see my hair. Slowly I took one curler out after another. The hair stayed up tight and curly. Following the instructions from the internet again I began to brush it up and away from my face. With each stroke it became fuller. I sprayed it to hold it in place. Finally I stepped back. There on my hair was not a wig but own silver hair high on my head in an up do. It was a style women wore in the 50's. I began to shake. I couldn't get my hand into my panties in time to touch myself before I came. It was so intense I had to steady myself on the sink. For the first time in a long time followed some regret and shame. "What have you done to yourself?" I said to my reflection. This couldn't be changed easily. I mean, I could shave it off but I could not even really consider it. I grabbed my brush and was just about to try and brush it out when a thought occurred to me. I was locked down, not seen as essential, so I wasn't even supposed to leave my place. Who knew when that would change? Finally, the shame just vanished. I smiled and decided to enjoy my hair. I had worked on it for two days. It was mine and I loved it. My day was wonderful. With my white button earrings, pearls and a cameo broche pinned to my collar I couldn't stop looking in the mirror. All day I would have to stop and touch my hair. I felt more like a woman than I had ever in my life. It was intoxicating, but mostly if felt right. Like this was the real me. That the young man David I shared my place with was the visitor. Monday morning presented a new dilemma. Normally I put on jeans and a polo and went about my work, but when I woke up and stood in the mirror I knew that even alone it was going to be awkward dressing like him. Carefully I slipped my gown off and panties. Pulling on boxers it felt strange. I picked up my shirt and was just about to try and get it over my beautiful hair without ruining when I just stopped. "This is stupid Mildred. You don't want to dress like this. There is no reason to. Get dressed the way you should be and stop playing around." I said to the mirror. An hour later for the first time ever I was seated at the desk in a pink and white house dress. The face of a 60 year old woman reflected in the screens. I had never done his work before but today was going to be an experiment. I crossed my legs at the ankle enjoying the feeling of my girdle and called into the conference call. The call was uneventful. Normal updates and tasking's. I gave my report then hung up. I felt good. Before long I was engrossed in my editing and seemed to have a new vigor for it. Nothing was new but I was comfortable and while not David any longer I was just fine doing the job as Millie. At noon I sat down to some tuna salad and put on Golden Girls. I especially liked the character that Betty White played, Rose. She was pleasant and kind. A little na?ve but still what I thought a woman like me should emulate. The next day was the same as Monday. Call work, talk with the team then computer tasks. I watched my shows. Friday morning Mr. Andrews explained that even after the virus was gone the company was considering making Tele-work a permanent thing. Production was way up. He called me out in particular and asked if I would be willing to forgo my desk and continue on in this capacity. I accepted without a pause. In my head I could be Millie fulltime forever if I wanted. In the back of my mind I knew I would have to go in to the office at some point and by then who would I be? But that was not something I was going to worry about. Another month passed and I was changing more and more. I had started studying the character Rose and practicing her movements. Her voice inflections. The terms she used. I would practice all day speaking out loud in a mature female voice. It got noticed on a call when I said "Oh your poor dear." To one of the art team girls when she said she had caught the virus. The call paused, then went on. It wasn't two minutes after the call that my work cell rang, it was Mr. Andrews. "Hello David, how are doing son?" he asked. It felt weird these days being called David. "Oh quite well, Sir. Actually splendid," I answered without a thought. "You don't seem to sound the same as the young man that left the office in January. Are you sure you are ok? Hell, if I didn't know better I could mistake you for a woman my age on the phone lately." There it was out of the bag. I paused and looked at my reflection. My hair was up and silver. I was wearing large ladies glasses that I had ordered on line. The skin on my face was starting to show the wrinkles I was trying to achieve through chemical scrubs. I was wearing a white blouse and a long broom skirt. Today I had on stockings attached to the bottom of my girdle while my hose hung on the rod drying. Finally I spoke with out trying to cover my now comfortable way of speaking or pitch of voice. "No Mr. Andrews I don't sound like him nor am I that young man that left the office in January at all. These past few months have given me the chance to really explore who I am. I have changed more than expected. But I feel delightful. I am still evolving I believe, but will hopefully become the person I am meant to be. I have made sure that my productivity has not suffered. I hope you are not upset with me. Are you?" "Not at all, you are just very different I can tell. In fact your work has been better than ever before. I commend you on it. I don't quite understand what you are trying to tell me but I won't push the issue as long as you continue this level of work. I may suggest that you start using text to talk from now on. Your voice has brought up some questions you may not want to answer. Oh and if you ever feel like you need to talk about things, please call me, you are not alone." "Thank you Ben. (Then I caught myself) Sorry, I mean Sir. Have a good day and thank you for the compliment," I responded. He may have said something else but I hung up. I was awash with a warm glow. "He said I sounded like a woman his age." I shuddered as a little leaking happened in my pad. The next morning I went on line and added the name Mildred Renee Jacobs to my address with the post office. Then I emailed the building and requested to add Mildred to the lease as David's aunt that was now living with him. I logged into David's bank account and added myself to the account. I expected that they would want ID from both and figured it would not work but within the hour I had a lease in my inbox that I signed as the new primary and two affidavits from the bank that we both had to sign and upload to the account. They wanted a copy of David's ID but did not ask for one from me. The next morning I logged in and saw Mildred on the account. I ordered new checks in my name. The virus was making it very easy to do things since everything was no contact. 10 days later my visa and bank card arrived. With them in my hand I made a decision that would forever change who I was. I went to an online pharmacy in Canada and ordered Estrodiol and Progesterone. I had been standing in the mirror naked that morning and began to weep. The body I saw was all wrong. It was soft but in a manly way. I had not dressed or acted like a man in months and I had no desire to be one. I needed to change and now. So I ordered the hormones. Work continued and no one seemed to question why I was only communicating using the text box now. My productivity stayed high and Mr. Andrews continued to sing my praises. He was such a dear man. One day when he was on screen I found myself looking more closely at him. His hair was short. Gray at the temples but still dark on top. He had kind eyes and laugh lines. I thought back to seeing him in person. He was tall, I would guess over six foot and still in nice shape. I almost missed a question from him because I was wondering what he liked in a woman. The thought startled me. Even after all the changes it had not entered my mind to find a man attractive, but here I was, getting flush looking at him. I fanned my face and said, "Settle down old girl," to which I laughed. In June things started to open up again. Grocery stores and finally salons. I had touched up my hair a few times but it really needed a professional touch. I also realized I was going to have to do something about a picture ID. After some research I decided that a senior citizen ID from the DMV may work. I wouldn't have to drive and I hoped that I could get away with my credit card and a print out from my bank account that I had uploaded a web cam picture too. That morning I made an appointment with the salon. I was nervous. While I had been out for walks and to the store now and was taken as the older woman I was now this was different. The stylist was going to have close looks at me, but I needed it done. So, I sat in the chair with a girl named Sam and explained I need my roots done and would like a cut please. Something shorter and more modern but not too modern just something to fit a woman my age. She commented once that I had done a nice job on my own but only once. I emerged ecstatic. I had the cutest little poodle cut, all silver, curly and easy to maintain. I couldn't help shudder at the permanence of my hair. When I got to the DMV I took a number and waited. The man behind the counter called me just as I crossed my legs. "Ma'am on Tuesdays seniors have priority. Now how may I help you?" I recited my practiced remarks. "You see I have just recently moved in with my nephew and during the pandemic my things were lost in transit. I am afraid that I have no identification. It is all gone. It scares me, it is like being a non- person. (I actually started to tear up for real) please can you help me?" He looked at me closely. "Are you sure you are really the person you say you are?" he said. Out of habit my hand went to my chest and I began to speak when he held up his hand. "Ma'am I am only fooling trying to make you smile. Now let's see what we can do." I was sitting on the bus stop bench staring at my new ID. "Mildred Renee Jacobs, Age 60 born June 25 1940. It had a number and my address and there on the corner was a big capitol letter F under gender. I had done it, Mildred was a real person she had picture identification issued by the state and she was me. Now remember in the background this all excited me sexually to no end. The fact that I had feminized myself and was essentially a 60 year old woman was amazing but I knew what I wanted to do to push it over the top. When I got home I went to the bedroom and turned on the light in the closet. There on the top shelf next to the foam head with my old wig was a green metal firebox. On my toes I reached up and pulled it down. Holding it I kicked off my Naturalizer shoes and padded into the kitchen and sat down at the table. I punched in the numbers and the lock clicked open. I sat there looking at the documents neatly spread out before me. David's passport, birth certificate, driver's license, SSN card, a copy of the divorce decree from Wendy, his library card and finally the badge he needed for access to the building at work. His entire legal identity was there. Next to it was one small ID, Mildred Renee Jacobs it read. Cute poodle cut picture. My original intent was to make a list and start working towards getting the same things he had, but then something came over me. I gathered them all up and stood up. Slipping my feet back into my sensible shoes I opened the door and went down the hall to the elevators. I pushed "B" for basement or boiler room, I don't know which. The building was old. Still being renovated and as such it was still heated with an oil burning boiler. It was hot and dark down there and it scared me, I didn't like it down there what if a man was hiding he could hurt me. I didn't even realize how much my personality had changed. I walked cautiously up to the big black beast and looked at the door with glass in it. I could see the fire behind it. Using the hem of my skirt I turned the handle and opened the door. The heat was intense and I stepped back, then in one motion I through it all in, everything all of David's legal person was gone in a flame. I hurried to the elevator when the door closed I was overcome with an orgasm more intense than the first time I saw my gray hair. I moaned in a female voice and pushed my legs together but it just kept coming. I shuddered and moaned and then it was done. As the door had closed so had David's life. I had just burned everything that said he existed I only had my ID, Mildred's ID, and it made me cum. It was July 4th and I was in the shower exploring my new sensitive areas, my nipples. I had only been taking the hormone for three months but my body seemed to be reacting quickly to them. There was little protrusions on the front of my fatty man boobs or as I called them lady growths. My areolas had increased in size from a dime to a quarter. My penis now stayed limp and I swore my testis were smaller, but most of all my nipples tingled and when I rolled them between my thumb and finger it was like a string was run from my groin and it was wonderful. My eyes were closed thinking of Ben. I had been fantasizing about him non-stop over the last two weeks. At first my changing sexuality concerned me but I was a woman and women liked men and I liked Ben. He had called me a few weeks ago and asked me point blank who was Mildred Jacobs and why was she on my accounts now? Apparently while doing an audit the accounting department discovered that a woman named Ms. Jacobs had been handling all my banking and he was concerned that it may be identity theft. I was quiet and was not sure what to say. I could lose my job if he took it the wrong way but at this point I knew I was never going to be David Jacobs again. I answered truthfully. "Mr. Andrews, I am Mildred Jacobs. I don't really understand why or how but I have transitioned to a woman and now live full time as Mildred or Millie if you prefer." I expected the worst but got the best answer I could ask for. "Well young lady congratulations. I welcome you to the company and thank you for being honest. I have to be honest, I have suspected as much but wanted to hear you say it." Tears began to well up, I was overcome with happiness. I could be open with him. "Thank you Sir, I am so glad you are ok with this. I have hated be dishonest or hiding from everyone, especially you." He laughed. "You don't have to apologize, I have a niece that started as my nephew. She is a beautiful person on the inside and outside, but I must say Mildred is quite an old fashioned name for someone your age." I made a decision and pushed the video call button. It took only a moment and I saw his face. His eyes got big and then softened. "My you don't look 35 or 36 anymore, and I know better than to ask a lady her age but I see you prefer a more, shall we say, mature look." "Yes I do, always have, and according to the state I am 61 now. I hope you approve." He smiled. "My dear lady you don't need my approval, you are an amazing person. Now would you please call me Ben, it seems strange to have someone my age call me Sir." I giggled and felt warm. We chatted some more and then signed off. The next day I got a call from HR and was informed that my records were being updated on the instructions of the CEO and forthcoming my checks would be made out to Mildred Jacobs. I cried. I don't know when it happened but within a week Ben and I started talking almost every day. He told me about his wife who had passed from cancer when he was 40 and how he just never found another woman he could connect with. How he threw himself into his work and became the man he is now. I told him about my past and how this all started we got the messy stuff out of the way early and soon he and I just talked as a man and a woman. Friends of the same age, he was older, but I found myself wanting more. September the country opened up. A vaccine was widely being distributed and as a senior I was one of the first group to get one. I ran into a problem when I decided that now I needed to make things legal and petitioned the court for a legal name change. Part of the process was to provide David's records of which I had burned all of them. I had removed him from my lease and was the only person living there. In court I told the truth how that during the pandemic I had become overcome with despair that I had to wait for this and burned everything. I told him the truth about my ID and that I understood I was basically committing fraud. With tears in my eyes I begged him to forgive me and not send me to jail. He looked at me stoically and then told he was not in the practice of sending senior citizens to jail. He gave me a fine and signed my decree of name and gender change. That afternoon the county clerk reissued my birth certificate and used the birth date on my ID. Walking out of court I realized that I truly was a 61 year old woman now. I felt amazing. No I did not have an orgasm. Those seemed to have stopped, right around the time that I realized I was a heterosexual woman and this was no longer a fantasy. I was not cross dressing I was who I was supposed to be. The next month we started to come back to the office and the day finally came that I was going to have to come in. To say that I was nervous was an understatement. So far the only person that had seen me was Ben. I had sent an email to the rest of the team explaining my transition. I even let them know that I was living as a much older woman that my birth age. I enclosed a picture. Those that responded where very nice and those that didn't I just ignored, but that day I would be sitting with all of them to see me. I don't think that anyone would have recognized me if I hadn't told them. The hormones had changed my body considerably. My breasts were C cup without any help. I loved them but my favorite part was how round my butt and thighs had become. I felt my bum move when I walked and loved how my support hose had become just that, support. My skin had been damaged just enough by the chemicals I used giving me the cutest crow's feet and soft wrinkles. I had chosen an ankle length dress in dark blue with lace trim on the bodice. I wore my pearls and button earrings. My hair was freshly colored and done in my favorite poodle cut, silver full and curly. No man would ever have this hair and no young woman would want it either. I felt and looked like a mature woman that was still in the work force and I loved it. Yet I was still a little scared. Ben and I had been out a few times for lunch and started to spend more time together. I wouldn't say he was my boyfriend but he was definitely more than a friend. Friends don't kiss at the door or hold hands. Since this was the day he offered to pick me up and we could arrive together. My heart was warm with his generosity and accepted. We walked into the building together. The security greeted us both and smiled. Once we got to the floor I went straight to the ladies room. I seemed to have to pee more often these days and since I had my testis removed I felt better about my little shrinking appendage. When I came out and looked through the glass walls of the conference room I saw the entire team waiting. Ben was talking already and I felt awful to be late. With a deep breath I opened the door and smiled. Ben smiled at me. "Ladies and gentleman let me please introduce Mildred Jacobs. She has taken over for David who is no longer with us. I expect her to receive all the same courtesies he was given." As I sat and smoothed me skirt he said something that caught me off guard, actually everyone seemed a little shocked. "One more thing, Ms. Jacobs and I have started seeing each other outside of work. I am quite fond of her and think her of me. I don't believe it will effect this office, but if it does we will reexamine the way forward. I tell you this because you all know who she was at one time and if I so much as get a whiff of negative talk or laughing you can pack your desk that day. Any questions?" Not one person said anything. Throughout the rest of the day he would stop by or put his hands my shoulders to reassure me. I resigned two weeks later. I just had no interest in the old person I was or his life. Ben tried to convince me to stay on is a smaller capacity but I wanted nothing to do with it. Besides I could now use Social security and I wanted a simple life of feminine things. I had Thanksgiving with Ben's family and it was wonderful. The house was full of cheer and grandchildren. I have no idea how it happened but I found I was overjoyed with the little ones. Little Monica especially would wrap her arms and legs and hold on. It was glorious. By Christmas I was spending more time at Ben's than my place. I guess it was inevitable that he asked me to move in. A few weeks later I was neatly hanging my dresses in our shared bedroom closet. He was a gentle and attentive lover. We were not spring chickens so we took things slow. He never once acting like my little soft member was out of place. He treated it as what it was, my clitty. I talked about SRS but it was not a priority. The day came that laying in his arms he whispered in my ear, "Millie I love you would you please marry me." It came to pass that I became Mildred Renee Andrews. Or to the grandkids, Grandma Millie. When the virus hit we were all scared and terrible things happened to people, but for me it was a blessing. I went from lonely young man to a loved and happy older woman, married to a wonderful man. Yes I aged and I would want it no other way.