Cheri; Oops A Mistake Then A Female

My girlfriend and I had been going steady for almost six months. I was already working, though I had only recently graduated from college. Sherry was still in college, finishing up her last semester. I was working in the IT department of a local corporation. The job was fairly easy; the only problem was the hours around the weekend. If the gods were with us, the weekend could be enjoyed, but if the servers were acting up on a Friday, the hours piled up as we had to make sure that all was back up and functioning normally for Monday morning.

My birthday was coming up this Friday, making it a special treat for me. I was allowed Friday off, a company rule that you got your birthday off, but still had to work the weekend if needed, that we wouldn’t know until late Friday evening. Sherry had made me an appointment at her salon for a spa day. I have been a crossdresser for most of my life, and that information had been shared with her from the start.

At first, she was not enthused about dating a crossdresser, but over the months, she has seen the other side of me, the feminine side. We get along well, sharing a lot of things that most couples never have the chance to. She loves to shop with me, where I am usually more excited about the choices than she is. My foray into dressing like a woman is pretty much confined to the house, my job keeping me from doing things that would allow me to pass in public.

I headed to her salon that bright Friday morning, excited to be able to experience some of my deepest desires. Sherry had talked to her stylist telling her that she wanted me to be able to see the girl in me just once. She had made a note, informing Jenny, her stylist, of what she wanted to be done for me. She had classes, with tests, later that day keeping her from attending with me. Since one of the classes was a big test she couldn’t just ditch the class for the day. All of the tasks performed would be temporary and easily washed off or out before I had to go to work. I carried the note with me, although it was in a sealed envelope. Sherry wanted my birthday present to be truly a surprise, something that I might remember for quite some time. The anticipation alone making everything seem much brighter and almost alive.

I made it to the salon a little before my appointment; Jenny was already there waiting for me with a glass of wine. She wished me a Happy Birthday and took me back to her station. I passed the note to her, then waited for her to read the contents. She got called to the front for a phone call, ten minutes later she returned ready to start. She leaned the chair back, so she could wash and condition my hair. The receptionist came back to see her, handing her the note she had forgotten up front.

As she washed my hair it felt so good, I was purring inside as she pushed the chair back to its upright position. I had finished the wine while she was upfront, so she refilled my glass. She ran a comb through my hair, getting out the tangles, and then snipped off my split ends (her words). She consulted the list, made a mention that the list was quite detailed, but quickly lowered the chair back down. She mixed a solution in a bottle, then started squirting it on my roots then massaged it into the rest of my hair.

The one thing that I had managed to do with my job was to grow my hair longer than it has ever been. Since IT department usually means nerds, a nerd with long hair in a ponytail is not an unexpected occurrence. My hair reached my shoulder blades, a brunette although the sun had lightened it some. Other than brushing it daily, it has not had anything done to it in years. When Jenny finished applying the solution, she refilled my wine glass again and then moved to the next item on the list. In the meantime, a large plastic bag had been placed over my hair to help process the treatment.

I was told that the hair treatment had to be left on for thirty minutes, so now would be a good time to work on my nails. She soaked my hands in a bowl of solution, according to her to soften the cuticles. I had almost finished the last glass of wine, so she waited as I tipped it back and drank all that was left. My head was already fuzzy, and this last drink put me out of it. As if you can’t tell I am not a drinker, but the nervousness from being made feminine had me knocking the glasses back one after another. Anything more than a glass of wine shuts down any mental functions. I was still awake, but no coherent thoughts were being processed by my brain. I watched as she worked on my cuticles, filed my nails a little then applied extensions to my fingernails.

The extensions were way longer than my fingertips, but looked good, like they should have been that long from the start. A coat of a base polish, then a coral pink polish and finally a topcoat were applied over the next twenty minutes. Then it was time to rinse my hair, again her fingers massaging my scalp felt so good. I took a peek in the mirror in front of me; my hair was so blonde almost a whitish blonde if there is such a thing. It did look good, though; my brain failed to notice that my brunette color was gone for good since all the color had been bleached out.

Back to my nails as my hands were placed inside a lighted box to set the polish. The only fleeting thought was that those nails are so feminine, even though they were on a male. It seemed like the fuzziness was getting thicker, like being stuck in an early morning fog, thicker and thicker, then only dissipating after the sun popped its head up. No sun here to dissipate the mental fog.

Back to the here and now, I think, as Jenny pointed a gun-like object at my ears. Six clicks later my earlobes felt funny, the heat from the laser warming up my earlobes as the light made a perfectly sealed hole for the studs and hoops. The earrings looked so good with my light blonde hair, their gold and ruby coloring making a nice contrast to my new hair color.

She had wrapped my hair in a towel and reclined my chair so she could work on my face. She used something to work on my eyebrows, as I felt little stings as she removed hairs that did not belong. The only thought I had was that I didn’t have many eyebrows to start with and now even less. When she moved from in front of me I hardly saw any eyebrow at all; my face looked so much better with a thin fine brow line instead of what I had on entering the salon.

I felt several creams and masks over the next hour being applied to my face, massaged in and then cleaned off with an astringent. Then false eyelashes were applied to my own eyelashes. These were individual lashes glued to my own eyelash, although much longer and thicker. The image in the mirror looked so perfect, even through the fuzziness of my mind I liked what I saw. It was just that I was feeling so good, the female inside me is emerging, and I was ecstatic. The fact that all of this was too much, too soon, and would cause such havoc with my life never gaining a foothold in my mind.

Jenny removed the towel from my head, using a spray bottle to moisten the hair again. Then lots of curlers were wound into my Champagne blonde hair, varying in size but with only one purpose, to turn my semi-straight blonde locks into a curly, bouncy feminine hairstyle. Under a dryer to get the hair dry, then thirty minutes later the curlers were removed. In their place, the tightly wound hair returned to the way it was in the curler. Jenny used a brush to loosen the curls, a soft, bouncy feminine hairstyle that framed my face the end result.

More than half of the day had passed, Jenny did ask me if I wanted anything to eat, but spoken words were getting harder to understand, so I declined, at least that is what I thought that she had asked. My next treat was to be makeup, something I had wanted to wear for ages, but time and inexperience had prevented that treat. Jenny went through a wide range of cosmetics from concealer to lipstick, applying each with precision. The image that was in the mirror was not what I was used to seeing, it was what I wanted to see, but never got the chance to visualize.

Jenny left me shortly after that; there was some commotion in the front of the salon between several ladies. There were several phone calls made and then Jenny returned. She told me there had been a mishap, and my girlfriend had been called. She told me to relax and get comfortable until she arrived. For some reason, I just closed my eyes and was soon asleep. Jenny was asking me to wake up, shaking my shoulder to get my attention. I glanced around quickly remembering that I was in the salon, then seeing Sherry in the back talking to another lady.

They went into the ladies office; then shortly Jenny came to get me. As she led me to the office, I kept getting glimpses of an attractive female in the mirrors as we passed. As we entered the office, Sherry hugged me tightly, almost too tight, as I felt like she was squeezing the life out of me. I was offered a chair and with a few wobbles, I managed to get seated. The other lady introduced herself as Francine, the owner of the salon. She asked if I was clear-headed yet, my funny look answering her question.

She talked with Sherry instead telling her that the lists got mixed up, and the end results are what you are looking at. Since the hair is so light, we can’t put another color on for a couple of weeks, the facial and masks were using the new technology that stops and prevents any hair growth. Since the eyebrow area was also treated, he will not have any more hair there than he has now. The nails are fused on, and the polish is one of our longest lasting. In other words, what you see is going to be his look for the near future.

Since the salon is the one that made the mistake, there is no charge for any of this. Jenny remembered that you had told her that he is employed, so if you give me his work number, I will call and explain all that has happened. I suggest with his looks that she dress as a female for a couple of months until we can access whether to reverse the changes, the ones we can or proceed with more to complete the look.

If his work doesn’t allow him to return as a female, I will match his salary until we can find him other employment. Her clothes will come from our boutique. Jenny will go over there now and pick out a set of clothes for her now. After I have talked to her work, we will decide what next to do. I sat there in a daze as Francine made phone calls and Sherry just stared at me. Several times she tried to start a conversation with me, but my answers made her aware that I was still not with the program.

Jenny came to get me, and we went back to the treatment room. She helped me out of my clothes and laid me back on a flat table. Two breast forms were laid on my chest and their proper position marked with a marker. She added glue and the forms were re-positioned within the marks. She placed one of my hands on each and then slid a pair of panties up my legs. I lifted my hips to allow them to be brought up all the way. She tucked my member so that the front is smooth and flat. I am aware of all of this, but it is as if I was watching a movie, not thinking about anything but my new look.

I am helped up, and a bra is slid over my shoulders. She fastened it in the back, adjusted the straps and settled my breasts more comfortably in the cups. A camisole is next, then a cute sweater. I am fascinated by my image in the mirror, the image I have hoped to see for years. A skirt is added to the mix and fastened in the back and zipped up. A pair of low heels are slid on my feet, and then I am taken back to the office. Sherry and Francine are talking as I enter and all conversation stops. Sherry hugs me, trying to squeeze my insides out once again.

She gets right in front of me, telling me that I have to work tomorrow, the main servers are down, and only Mark is in town to help me. Melissa, the department head will be there also since they are three technicians short. I guess that is what it took to sober me up, I looked down at my body and broke into tears. Sherry comforted me; everything has been explained to Melissa, she doesn’t have any problem with it, but mentioned that I might kidded a little next week by a few of the good old boys.

Sherry took me home, the drive there totally in silence. I was shocked at my looks, the image that I always wanted is now exhibited on my body, except things like work and real life has not changed. I find my way into the house and go straight to our bedroom. I stare at the full-length mirror on our closet door trying to see if anything masculine is hiding somewhere in that image. Sherry comes into the bedroom, hugging me and getting me to sit on the edge of the bed. My head still hurts, maybe a little more coherent, but not by much. I must have drank way too much, my head has never hurt this much before.

She assures me that Melissa is alright with my new looks, and she will speak to the guys before Monday to keep the teasing down to a dull roar. In a way she is anxious to see the new you, maybe something she could get used to and keep for the future. Another female in the department would be most welcome.

Between the wine and the stress of finding out I have to work and the gorgeous female image that I see in the mirror, sleep comes pretty easily. Sherry had laid me back on the bed, gave me a sensuous kiss and told me to sleep tight.

When I wake up the next day, it all comes back to me, along with a dull ache in my head due to the wine. Sherry is already up and helps me get dressed in another outfit. I get to wear a pair of her pants and a sweatshirt, but the breasts make the image very feminine. She helps me with my hair, adds some makeup after she cleans off the old then hands me a purse with my wallet, lipstick, and mascara for the day. I look at her, she points to my lack of pockets, gives me a kiss and tells me to have a good day. The stare I returned to her wish for me to have a good day caused her to erupt in giggles.

I walk out of the house and get into my car, then head to work. By the time I get there my nerves are frazzled, but Melissa pulls into the parking lot at the same time and opens my door. She compliments me on my hair, loves my nails, then just leans forward, and I get a hug from her. We walk in together, and she shows me where to put my purse. I start on the main server running diagnostics trying to pinpoint the problem. Melissa had walked up behind me, and was watching me run the different tests. She commented that the longer nails don’t seem to be bothering you, in fact, she thinks I am faster than without them.

About this time Mark shows up, he also steps behind me and watches me work. I know he is there, but I don’t want to acknowledge him since I fear his teasing and wise ass remarks. However, none of that happens, he spots a broken link, caused by one of the switches and heads there to check it out. As he leaves, I let out a big sigh; I feel like I had just been able to walk away from a firing squad with no blood present on my body. Melissa goes to check the hard drives to make sure one of the connections have not come loose.

Shortly, Mark returns telling me that the switch was okay. I had only two more diagnostic tests to run; then I would be done. If it wasn’t on the main server, we would have to check the other servers where some of the data is stored. He stood behind me watching the code scroll across the screen. His next comment surprised me. “You are pretty good for a girl, fast, accurate and pretty to look at.” Melissa giggled in the background; I think she is taken unless you want to tangle with Sherry. Mark blushed red, said he would start checking the other servers, but I still think you are quite attractive, as he walked away.

The last diagnostic test found an error in one of the modules, so I started re-installing the data from the latest backup to overwrite the error. Other than taking quite a bit of time, it is easily fixed. Five hours after we had started the repairs we were able to walk away from the office. I had run some tests to make sure all was operating properly, the success of these making us feel pretty good. Failures on a weekend don’t always have solutions, and especially as uncomplicated as this. Melissa thanked me for coming in and told me she would see me Monday. I pointed to myself; she got the hint.

“It might be nicer if you wore a skirt or dress, but other than that we hired you for your skills not how you look. Today showed me I had made a good choice when I hired you. Thanks again for your help, maybe Sherry could use a little extra loving tonight, you know her good for nothing boyfriend skipped out on her. Since you know how her boyfriend can be, maybe you could ease her pain a little.” She giggled and pushed me out the door.

The drive home seemed to take longer, maybe since the crisis had been taken care of the urgency not there anymore. I parked in the driveway, then made my way into the house. Sherry came running from the kitchen to greet me; I think she is more worried than I am that I might lose my job. She wanted to know what happened, so with the diet soda she had handed me, I sat on the couch and filled her in. She giggled about Mark’s remarks, but I could also see where they bothered her a little too.

She had made us some supper, so we adjourned to the kitchen to consume some of her cooking. It was superb since I hadn’t eaten anything this morning because of my nerves. It turns out I was famished, even taking a second helping of one of the dishes. I helped her clean up, something I had never done before. It somehow seemed like the right thing to do now. We headed to the living room where we sat and talked into the wee hours of the morning. One more day to go before Monday, a day that I was already dreading with a passion.

Sherry had made a trip back to the salon to get me more outfits for the upcoming week; I was apparently going to be one of the best dressed IT people come Monday. She had me practice walking in heels, also sitting and keeping myself modest. We had another tasty meal, and I again helped her clean up and put away the dishes. She told me right then she would never let me return to being a male, my actions the last two days making her love the new person in her life that much more. That is, if that was even possible.

We talked a lot that night, mainly of what to do about my work. The consensuses at the salon is that it would be at least a month before some of the changes could be reversed or undone. I asked her about losing her future husband; her reply startled me. He was alright, but the person sitting by me is so much more loving and caring, I would gladly trade him in at the first opportunity. I smiled, maybe this might work out, I know I am ecstatic at my new look, the feminine me locked in the closet for years finally seeing a little daylight. That is when I forget about all of the problems associated with this, most likely to surface tomorrow.

On Monday Sherry helped me dress, did my makeup and hair and then I headed to work. In a way, I was more nervous today than when I had to come in on Saturday. Lots of people to deal with, and explain why I am dressed the way I am. I got to my office and started doing my daily routine getting all the servers up and running, making sure that all the virus protection is functioning. I checked my email, finding one from Melissa explaining about me. It was short and sweet and sent to the entire company. Chad is now dressing as a female, still performing his tasks as before. They will be no harassment of this employee, failure to abide with this will result in termination of your employment immediately.

By now most of the employees had arrived at work and were signing on to the system. There is a little more traffic in front of my office, the curiosity of some of them requiring a look at the new female in IT. After getting the servers up and running I kept working on a new addition to one of our programs, letting the outside sales force to tap into our system, to utilize the warehouse inventory figures and check on available shipping dates. I was making sure it was functional before I uploaded it to the main server. Melissa called and asked me to come to her office.

As I walked that way I began to get nervous, I know she had made it a lot easier for me, but that was before the corporate executives could put their two cents into the mix. I knocked then entered, noticing she had another female with her. I thought I recognized her, but wasn’t positive. Melissa introduced me to Sheila, the head of personnel, Human Resources for those requiring a more politically correct term these days. They both greeted me, and I was able to sit in the other chair without making a fool of myself. Melissa smiled. “Relax; this is good news; we just need to run this all by you.”

Sheila explained that the company had been fighting gender requirements for several years. The government requiring more females in higher level positions in the company. Finding qualified females to fill those positions, quite difficult at times. When Melissa called this morning, explaining your problem this weekend, I asked to meet with her; this might help us solve several situations that we are faced with now.

Melissa is going to be promoted to head of all computer operations for the company. This leaves her old position vacant. You were already slotted for her old job, before this weekend. What we would like to talk to you about is declaring yourself transgendered with regards to your employment with the company. Thus allowing us to use your new female status to ease our restrictions with regards to gender quotas. You can, of course, change your mind later, a lot of transgendered individuals do, so you would not be sacrificing your gender permanently. It would require you to dress and act female here at work for the foreseeable future.

I know this is sudden, but it would help us out and ensure you a hassle free time in the future. Melissa has told me of your success this past weekend, and your presentation now is quite professional. Of course, you will receive a substantial raise, a few more perks health wise, and some retirement benefits not previously offered to your job description. We would like you to take the afternoon off and talk with your girlfriend, then give me a call later today with your decision. Melissa will remain your boss, both of you just stepping up one level. The CEO has already been told of this offer, she agrees with our suggestions, so now all you have to do is let us know your decision. They asked if I had any more questions, since I had none, Sheila then leaving to go back to her office.

Melissa smiled, see what happens when you dress as a female at work. She congratulated me on the promotion, quite confident that Sherry will approve of my gender change. I left her office and returned to mine. I closed out my work, shut down my computer and got ready to leave. Mark came into the office, shaking my hand, but looking a little sheepish. He had already heard of the promotion but wanted to make sure he apologized for his words over the weekend. He admitted he was out of line making comments about my attractiveness; his opinion has not changed, but he now realizes he can no longer publicly make that statement. He appreciates my experience and knowledge and feels fortunate to be able to work with me in the future. I give him a little smile, but tell him his ability to shovel the crap around is still first class. I start to giggle, as he relaxed some.

I tell him to call me at home of there is any problem, otherwise, I will see him first thing tomorrow morning. The drive seemed much longer than normal, but getting home, I did feel better. Sherry would not be home for several hours since this is her long day. I made my way to the den, a favorite spot for me to stop and think through problems that affected me. The window at the back of the room is overlooking a quiet, serene spot in the backyard where squirrels and birds often played splashing around in the birdbath and trying to bury the nuts they harvested in the ground surrounding the area. I sat there for quite some time when I heard the front door close. I had intended to fix dinner, but my zoning out had nixed that idea. I gave her a big hug, she wanting to know how my day went. I told her I was home at one, being sent home by the powers to be.

She grabbed me and tried to comfort me, thinking I had been fired. I suppressed a giggle, much harder to do then when Sherry managed the task. I told her since I had wasted my time this afternoon, I would take her out to dinner. She looked at me strangely, suggesting that it might be better and save what money I had left. This time, the giggle won out, she hit my arm hard, wanting the truth and all of it. I told her to change clothes and I would confess all at the restaurant. I called the restaurant I had in mind and made reservations, they had several private rooms that would be perfect for my surprise.

I even went and changed into my only other female outfit, a red business suit, with a pencil skirt. I almost changed back when I tried to walk in the skirt, but decided to brave it out. When Sherry emerged, she took one look at me, and raised her arm, but I told her no, she had to be a good girl and wait until we got to the restaurant. I could see she was frustrated and often when she got that way she wanted to hit something, and since I was withholding information I was the one to hit.

Since I did not have a proper driver’s license she drove when she saw where I had her drive too, she gave me a look, and I could see tears sliding down her face. She managed to find somewhere to park, and we entered the restaurant. I gave my name, and we were shown to the private room. The waiter helped us with our chairs and took our drink orders. I think I figured out what Sherry thought might be happening, so I changed directions a little. I had been contemplating asking her to marry me for quite some time, finances and my go nowhere job holding me back.

I figured out I would lead with that, at the same time slipping off my mother’s ring off my pinkie finger. She had given it to me with the intent that I would give it to my fiancé when and if I asked her to marry me. I think Mom had doubts whether I would marry, she also aware of my need to dress in female clothes. Our drinks were brought, and the waiter took our orders. I ordered two of their house chicken salads, a favorite of ours when we ate there in the past. They were expensive, but more than one person could eat.

I took Sherry’s hand and held it in my own, telling her how much I loved her. I told her I would normally get on my knee, but the pencil skirt might not allow that maneuver, so she would have to accept this. I asked her to marry me but wanted to make sure she would have no trouble with me as Cheri. She mouthed yes, I had managed to leave her at a loss of words. I slipped the ring on her finger and kissed her on the lips. I had scooted my chair closer, and we played tonsil hockey for quite some time. The waiter had noticed and had returned our food to the kitchen to be brought back out when we were through kissing. I presume he figured the kiss would take some time.

It did require quite a bit of time for us to return to the here and now. A lot of kissing and quite a few tears shed by both of us. The food was returned when the waiter saw our faces for more than a few seconds. We nibbled while maintaining hand contact with the other hand. Like two new lovers, we couldn’t get close enough to each other or allow any distance between us for fear of losing one another. The salads were good, though anti-climactic to the proposal. When we finished, she remembered me being home early and asked what I was going to do now that I didn’t have a job.

I looked sullen, like if I had been reminded of something I wanted to forget. The giggle escaped anyway, and Sherry hit me again. I told her she was damaging the merchandise; she just stared at me, good, now tell me the truth. I told her about the promotion, the pay, and the better benefits. She was thrilled; then I told her Cheri is now here to stay. She stared at me trying to understand why Cheri is here to stay. I explained what Sheila had said, about the fact that I could change my mind later, but also why I thought that would never happen.

Number one it involved the government, once I am listed as transgendered, it would take an act of quite higher power to actually allow me to dress as a male again. Then most likely they would just fine the company for noncompliance. Two, to live as a female for any length of time will require what I have now undergone and much more. Changing back to a male is not going to be easy at any stage of this deal. I told her I love her with all of my being, but she needs to know that she is marrying Cheri, not Chad.

She thought for a minute, then in a normal tone told me that she accepts, but if she carries the baby to term, I have to agree to breastfeed the little darling when it pops out, also the diapers. The biggest smile I have seen on her face since we started going together is plastered there; then she starts giggling as she reaches for my breasts.

I guess everything went alright; Sherry did agree to marry me, the Cheri me, and with the new job, I will be able to support us much easier than before. It took me several weeks to get used to the changes. Each day it became easier to become Cheri, I soon acquired the skills to maintain my hair and do my own makeup. The job is much easier than I anticipated, the work primarily what I had already been doing, although a little more of it. Mark had quietly spread the word about me, warning the other guys about what they said to me. I got a reference to my male self once in a while, but when I didn’t comment the subject was quickly dropped.

Sherry never flinched once when I appeared every day as a female. She treated me the same as before, although the loving and romance side of things got more interesting. When I made an appointment to get my roots done, it was suggested by Sherry that I go ahead and make the full change except for junior. The day before my appointment she called me late at the office wanting me to go by the sperm bank and make a donation. Melissa was in my office at the time, and when I mentioned sperm bank she broke out in giggles.

After hanging up, Melissa asked if she could come along and help me make the donation, then broke out in uncontrolled laughter. I reminded her of the company rules on harassment, but she said that didn’t apply to females. Then more laughter. Red in the face I closed up my computer and got ready to leave. I had gotten the address from the internet and was on my way. I arrived about thirty minutes later, entered the lobby and told them I wanted to make a sperm donation. The receptionist looked at me, wondering if this female standing in front of her is nuts. I finally figured out the problem and quietly whispered to her that I am a male, and my girlfriend wants me to make a contribution to be used later.

She gathered up the forms necessary for the donation, had me sign in the appropriate places than handed me a vial to use to gather the donation in. All the time she is straining not to break into laughter. I went into the room designated, lifted my skirt and removed my undergarments until junior is free. It took me a while, but finally thinking of Sherry sucking on my breasts made the donation possible.

I went back to the reception desk, handed her the vial and thanked her for her help. She had calmed down quite a bit, apologizing for her actions, and thanking me for the pleasant break in her day. Jokingly she asked who is going to have the baby, with a straight face, I responded that it is up in the air at the moment; Sherry wants me to do it, but then she doesn’t want to breastfeed, so it looks as if I will be doing the breastfeeding and diaper changing. She made me promise to keep her informed of who is doing what, now that she knows part of it she is dying to hear the eventual outcome.

I made it home about forty minutes later, the traffic is horrible, the sperm bank being on the other side of town not helping in my commute. Sherry had dinner ready but had to find out what happened at the sperm bank first. I conveyed the story, even giggling myself some now, it did sound quite unusual, and my remarks about possibly carrying the baby made Sherry break into raucous laughter. Her only comment is we might just do that; I know I would prefer it that way.

The last few days her cooking has reached epic proportions. She has always been a good cook, but the last few nights I have felt like I had died and went to heaven when consuming her meals. We talked some about getting married but decided to hold back a while to make sure that my promotion was genuine, not just a maneuver by the company to keep from getting in trouble.

Even though I cross-dressed most of my life living full time is quite different. It is another whole routine that females go through every day, makeup, hair, clothes selection, and the biggest, body maintenance. At night, removing my makeup, cleansing my face, then moisturizing, all just so that I can put on a nightie and get some sleep. Sherry, however, is not content with me getting some sleep, my new equipment is constantly being stimulated by her, her whispering in my ear that all of her foreplay is leading up to getting me pregnant, then I can stay at home and raise our children. I do have an opinion on that, just not sure what exactly it is or if it should be voiced.

I know me getting pregnant is not possible, although it has always had a place in my dream fantasy. I think most males who worship being a female wish they could experience that aspect of the female life, but maybe wanting it and actually experiencing it are two different things.

Another morning, an extra hour is required every AM to get me ready for a day at work. As a male, I just pulled on a pair of pants, a shirt, did my bathroom things and strode out the door. Not so for a female, picking out something to wear, doing my hair and makeup, then getting dressed, checking my purse for the essentials to make it through the day, then the appropriate shoes before I head to the door. I forgot to include numerous checks in the mirror to make sure my female image is up to standard, a usual application of another coat of lipstick or gloss to make the image perfect.

I had managed to get a driver’s license with female as the gender and my first name changed to Cheri, so the drive to work is less stressful. At first, I was petrified at being pulled over and asked for my I.D. Then being arrested and taken to the station to be interrogated about my identity. I know, an overkill, but the fear was real. On the way to work any police vehicle, even going in the opposite direction, causing me a lot of grief and worry.

Work went well, my staff and I were caught up on everything, now working on new programs to be added to the servers. I worked several more Saturdays, even a Sunday or two, when the servers gave us trouble. There was never any remarks made again by any of my male staff. I think the one occurrence with Mark was enough to prohibit any others. Melissa and I got along even better, even eating some lunches together from time to time.

The best part was the relationship between Sherry and me. We were much closer than before, she was teaching me to cook, among other things. We went out shopping, my enthusiasm and her practicality a good blend. Our late night conferences in our bedroom were always looked forward to. We snuggled, kissed, licked, and otherwise manipulated each other to great heights. Then we would cuddle, enjoying where we had been, and looking forward to many more days ahead. A truly fantastic future, all made possible when a list got mislaid. A lifelong adventure now unfolding.

It was about a year from when I was promoted when I was called into the CEO’s office. The visit worried me, seldom do any of the lower echelon staff ever have any interaction with upper level management, especially in this company.

As I was shown into the office, Melissa was seated to the right, and a new representative from Human resources to the left of the desk. The only chair left right was in front of her desk. I nervously sat down placing my hands in my lap, like a proper lady is taught to do. “Cheri, my name is Janice, and we are here to discuss some changes in the computer department. Melissa is returning to her original job, as per her request. I will let her tell you why, when this meeting is over. That leaves her present position open, you are more than qualified to fill the position, and we just have one minor question to ask first.”

“H.R. and myself are quite happy with how you have handled yourself, over the last year, and we hope we might be able to persuade you to continue your employment here as a female. Technically we shouldn’t be having this conversation with you, but we do care about the relationship here between the company and you.”

Of course, if you accept there will be more money, a much better benefit package, and a fully funded retirement package. Please take a few hours to think about this, I am sure you will want to talk to Melissa as to her reasons to step down, then maybe your fiancé also. Come back to the office later, or send me an email once you decide. I do hope your answer will be in the affirmative.

Melissa and I left the office, with me staring her down as we walked back to her office. She set in her chair, gave me a big smile and told me she is pregnant, wanting to deal with a lot less stress as she carried the baby. Besides you are doing so well, it won’t even task you brain to handle the job. Of course, I hugged her congratulating her on the baby, asking when it is due and if she already knows the sex of the baby. Have you taken the time to do the baby’s room yet? Is papa excited about the new arrival? A bigger smile, “you are such a girl Cheri, I wondered why I didn’t see it from the first time I met you.”

I knew I would accept, what I was living now a wonderful dream come true. Whether to ask Sherry first is now the question, Chad would have not gone to the trouble, just accepted the position and went on with his life. The fact that Sherry had supported me through all of this not lost on me. We were a team, and she needed to be consulted. I think I knew her answer ahead of time, but still needed to confide in her. I made the call, wanting to know if she was busy. She had one of her big finals earlier today and I am sure she was stressed out.

She was free, what did I have in mind, I suggested a meal out and a movie afterwards. I had kept my appearances limited initially, not confident enough to go around in dresses and makeup. At the office I felt that everyone knew me, so I did wear feminine clothes quite often, not dresses every day, but at least a skirt and top or feminine pants and a top or sweater. Everybody assured me that I was quite passable, but I still had lingering doubts. Tonight I was going to get rid of those doubts.

I had made reservations for dinner, a nicer restaurant that served a variety of cuisines. I made the trip home, made up a bath of heavenly scents and dove in. I was soaking when Sherry came in. “Oh, a delightful bath that smells so good, what is the special occasion? I take it that something went right today, or is it the other way around? The fragrant bath to make a bad day go away.”

“You will have to wait for that answer. We have time, should I fix one of these for you?”

“A mystery huh, yeah I might as well smell wonderful for this occasion too.”

I removed myself from the tub, drained out the water and fixed her one exactly like mine. Before it had even filled up she was in the tub, luxuriating in the fragrant and oily water. I started dressing, anxious to trap all those wonderful scents next to my body. No holding back tonight, garter belt, stockings, corset and the classic LBD and I do mean little. When Sherry finally emerged she took one look at me and hurried to her closet. “You could have warned me it was a fancy affair, I will not tolerate my spouse looking better than me.” Giggling sporadically as she threw clothes everywhere trying to decide what to wear.

I moved on to makeup, the last year I had become pretty skilled in applying my own makeup, it took me a while but the results were worth the effort. I even added false eyelashes and several colors of eye shadow blended to match my lipstick and lip liner, a burgundy and dark red combo. I never did get the ability to do my hair in a myriad of different styles, the mind was willing, but the hands never could perform the tasks. Maybe now I could afford a weekly salon appointment for my hair. I went with my usual a high ponytail at the rear of my head with dangling ribbons to secure it.

I walked over to the full length mirror, did a spin to make sure all was as it should be then switched my things to a purse that matched my dress. Sherry had been silently watching me, a smile and a smirk evident every once in a while. She looked equally stunning, a strapless crème lace piece of nothing that molded to her figure perfectly. After getting her purse she grabbed my arm and led me to the car. She made sure I didn’t mess up anything as I entered the vehicle, then helped me buckle my seat belt. I think she just wanted to show off her boobs, keeping them directly in front of me, seemingly about to escape her next to nothing dress. Believe me I was tempted.

I took over once we got to the restaurant, the Maitre’D having my reservation. I had asked for one to their private dining rooms, off to the side but easily accessible. We were seated and the waiter promptly waited on us. I ordered for both of us getting lobster for her and lasagna for me. Once our drinks and salads were delivered she leaned forward and that thousand watt smile came to her face. “Okay spill the beans, I want the truth you little vixen. Someone is extra happy and looking oh so hot. I would have been just as happy staying at home and getting you out of those clothes, but some allowances have to be made for loved ones. Now start talking.”

“Your hot little vixen now runs the computer department at work. Melissa is pregnant, wanting her old job back so she is less stressed. They asked me if I wanted the job, but I told them the decision had to wait until I asked my significant other what she wanted me to do. There is a stipulation though, I need to still present as a female, a transsexual in transition. The money is quite a bit better, so maybe we can now buy that house we have wanted. It is all up to you, can you stand being with the female me for the rest of your life?”

Well her attacking my lips might just be an affirmative answer. Her tongue instantly part way down my throat. I did see the waiter look through the door and I held up a couple of fingers to delay any delivery of our food. He smiled and withdrew. I guess a lesbian relationship still is a little rare, especially the showing of affection in public as we were obviously engaged in.

I was amazed that they were able to keep the food hot for that long. Sherry eventually ended her attack on my lips. We both had to fix our faces, the lipstick smeared real good. We had adjourned to the ladies room, this major a repair a little much for a compact at the table. When we returned the waiter went and retrieved our food. Even kept warm it was delicious. I told Sherry everything that had happened, making sure she was well informed on my job and my looks for the future. As soon as we finished dinner, Sherry wanted to go, her agenda could not be completed while we were in a restaurant. She offered to drive, completing the trip in record time.

I was hustled in the house, my clothes strewn along the floor from the front door to the bed. She jerked her dress up, pushed me back on the bed and was straddling me in an instant. I barely had a chance to get situated before her sex was being rubbed all over my mid-section. Of course, that had the desired effect, soon she had swallowed my male organ into her warm moist lips. It was a few minutes before I needed to get up to prepare for work the next morning before the romantic interlude ended. That day seemed particularly long, no sleep and the memories of all that we did that night wandering around in my mind.

Shortly after I had been promoted to head of the computer department, Sherry decided I need to take the feminine look up another step. She made the arrangements and took me to the salon. My old breast forms were removed my chest cleaned, then a clear cup was glued to my chest bigger than my original breast forms. Hoses were hooked to the cups and then a pump was started pulling my flesh up into the cup. It was a steady pull, then switched to a cyclic pull as the cups slowly filled with my tissue. I was lying there watching what was happening, and was about to put a stop to this. Sherry leaned and kissed me hard, then ran her hand over my groin. That is all it took, my mind went blank, my next thought is if my new assets would fit in my present bras. Six hours later I now had realistic breasts, breasts that are definitely mine.

After the pump shut off, two syringes of liquid were inserted in my nipples, one in each nipple. The hoses were disconnected and I was helped up and into a new and bigger bra. Dressed again Sherry hustled me out of the salon, I apparently had an appointment with her in our bedroom, and she wanted me there quickly. I felt secure knowing the cup was still protecting my new orbs, but when I was undressed a little while later there was nothing but soft flesh there, the nipple hard and erect. As soon as she got the one nipple in her mouth, my world suddenly exploded. Gawd, that feels so good.

So now after very little sleep for two days, but also sexually worn out I still had to go to work. As usually happens when you are tired, the problems of the world make themselves known. As I entered the office Mark announced that the servers were down, not responding to anything they were doing. When I entered the server room Melissa was busy trying to get any response she could from the unyielding machines. I glanced around looking for anything out of place. Then I saw the end of a cable in a space between the server and one of the work tables. I smiled, probably the cleaning crew, caught the cable and unplugged it. Not knowing what to do they tried to hide it to keep from getting blamed. I went over to the cable stooped down, quite a feat for such a tight skirt and plugged it in. The room came alive as the servers began to boot up, lights flashing everywhere. I looked at Melissa, as Mark smiled and I went back to my office. I wish everything was this easy these days.

Unfortunately, the day continued in that vain, one of the hard drives stopped mid-stream, we had to install another one this one fried to a crisp. Then load the backups by hand since it was still midday and the complete backup had not been made yet. Two more minor disasters late afternoon, software freezing up and having to be re-installed. By quitting time we were all ready to leave the building.

As head of all computer operations I found out that numerous public appearances were mandatory. I attended all of the executive meetings, having to update the others on what our status was. Then once every quarter the company board meeting, explaining to the board members what we were doing and future hardware needs. I had to make and maintain a budget, hardware and labor for my department. I now understood why Melissa wanted to regress back to her old job while pregnant. The tasks were not hard, but time consuming and a little bit stressful.

The first board meeting I attended was stressful for me. I am not sure how much they knew about me, so I was on pins and needles as to what would be asked of me. It turned out to be a non-event, budgets and long range computer needs the only things discussed. I did notice several of the older gentlemen admiring my boobs more than once. I guess that comes with being a female. Not something I had contemplated when I dreamed of living as a female earlier in my life.

My times at social events, executive meetings and the board meetings were interesting. I had to dress nicer, usually in a dress with jewelry and makeup. Of course, the mandatory salon appointment before the event, can’t have my appearance be judged as inadequate. I did enjoy the female part, now wearing dresses to work almost every day. Sherry seemed happier now, I was around more, in a better mood most days, and of course we no longer had to worry about money.

I know in the bedroom she was the dominant one now, my place now below her. A position I was enthusiastic about. On more than one occasion I found myself moaning, even some screaming as she manipulated my new assets to her satisfaction.

This also transferred to our free time. At the drop of a hat we would hit the stores to shop. Not a lot bought, but we managed to keep up with incoming arrivals of new merchandise at every store we normally shopped at. Of course she made me try everything on, to see how it fit. I later learned even if it was for her, I had to try it on. Turns out we are the same dress size, only I have a little larger bust. Besides she loved to make me model everything, and decide if what I was modeling would work for her.

Eventually all of my male clothes found their way to a thrift store, now both of our closets jammed with our female clothes. The last time I looked there was only two pair of pants, all the rest either skirts or dresses. When Sherry finds our dream house, the one requirement is lots of closets.

Work settled down and after a very successful year in my department I was promoted again. This time to COO of the company. Melissa after having a couple of kids came back to run the computer department, her hubby being the mother and housewife of the relationship. Sherry and I have them over often, Melissa talking with my wife and Jamie and I comparing notes. Jamie has adopted the female dress and mannerisms, we often meet at the beauty salon when we have our hair done. Since she has kids to watch during the week and I have my job leaving only Saturdays to be our only time to get beautiful.

Would I change anything if I had to do any of this over? Nope, life has been nearly perfect, and Sherry and I have never been happier. It has been an adventure, but well worth the time and effort. A never ending adventure, I might add.

My secretary entered my office, announcing that the CEO was in a plane crash and was being flown by helicopter to a hospital at this moment. I made a few calls to get people to cover for me, then headed to the hospital. Janice the CEO is one of my dearest friends, but I have called Sherry to keep tabs on her till I can get there. It turns out Janice is only suffering from the trauma of the plane crash, nothing broken or severally damaged. She had me take over for her until she gets back, so now I am the acting CEO and my usual COO for a while. I visit her daily, but all we talk about is her recovery. I try to tell her how things are going back at the business, her only remark to me is that she has someone handling things for her, not to worry.

A female life to be sure, never knowing what will happen next, this just the latest episode. It all started with an Oops. I do realize how blessed I am, good friends and a wonderful lover who has always supported me unequivocally.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

Leave a Reply

Your email address will not be published. Required fields are marked *