Olivia; A Trial In The Female Gender

I was back in town for the first time in two years. The last two years of college consuming that time, my degree in business economics finally obtained. I finished junior college in my home town, but wanted my degree to have a little more clout than just a state university. Beckham School of Economics had that clout that I desired. I found these last two years to be quite a challenge, the courses they offered were very challenging, covering every nuance of the economic spectrum. I graduated fifth in my class of twelve hundred, bringing with me a list of prospective employers that would like to meet me in the area. This was part of the Beckham experience.

My sister met my plane when it touched down at Sky Harbor International Airport. I was hugged tenderly, the two of us the only remaining part of our family. Our parents had died when their plane crashed while on a second honeymoon. I still took the plane when I had to, but was always very uneasy doing so. We picked up my luggage and she drove us to the home we had been raised in. It was located to the south of Phoenix, just around the corner from South Mountain Park, near the town of Guadalupe. Enough out of town to be out of the hustle and bustle of the city. The house is located on ten acres, so there is some privacy from neighbors. The acreage never developed before my parents built their house here, still spotted with some cactus and the native mesquite trees. It was slightly rolling land, as was all the land around South Mountain Park.

I carried my things in the house, and up to my bedroom. Hung up my clean clothes and sorted the ones needing washing. After I started a load we adjourned to the enclosed patio to drink some iced green tea and catch up on each other’s lives. Since it was still early April the weather was warm but not obtrusive in the valley.

We got around to my list of prospective employers, Jean, my sister, circling several that I should interview with first. She had helped me with hanging my clothes, suggesting that I might want to buy a few new threads, a good impression very important with a new employer. I agreed, but didn’t say anything more on that subject.

Ever since we were children, she took an inordinate interest in how I dressed. She was always meticulously dressed, never a thing out of place. Her hair styled to perfection, her makeup always perfect. I guess it has served her well, five promotions in the last three years, and now head of a division of her company responsible for over five hundred employees.

Where we differed was her opinion of how I should dress. I am small for a male standing five foot six inches. I have a reasonable build, with moderate width shoulders. I tip the scales at one hundred fifty-three pounds on a good day, less than that most of the time. Sis favors the androgynous look, a pant suit with blouse underneath in a Grey or tan for me. Most male suits look huge on me, the shoulders so wide it seems to swallow me inside of it, so she has insisted on a female pantsuit. The cut is usually not very feminine with her choice of colors it could loosely pass as an item of male apparel. I did stress loosely, a female would notice a difference right away, any male probably missing the obvious connection.

I had already conceded to longer hair, most of the time at college it was worn in a low ponytail tucked into my shirt. This has always been one of her first requirements of me, short hair and me, she says, looks absolutely awful. I tend to agree, the few times I have had short hair it did nothing for my looks. With short hair my refection in a mirror showed an image I had no idea who it belonged to. If a guess had to be made most would figure I was still in high school and most likely a nerd.

When I started yawning she dragged me off to bed, kissed me and told me to get a good night’s sleep and she will help me get ready for the interviews in the morning. Again an appropriate place for a comment, but I kept quiet and headed to bed. By the time I managed to withdraw myself from the bed the next morning, she had already lined up three interviews for later in the day. My clothes were laid on a chair in my bedroom, I sighed when I saw them, but maybe I could stand the embarrassment today. There would be additional opportunity tomorrow or the day after for other interviews.

She brushed my hair for me, something I had missed while away at college. There is nothing more relaxing then somebody running a brush through your hair. When I lived at the house it was a frequent treat for me, she loved to do it, a way that a sister could show her love for a sibling. You noticed I said sibling, I really doubt she saw me as a brother, more likely a younger sister.

Next a pair of sweats, some sneakers and I am dragged out of the bedroom, down the hall and into the garage. The color of the sweats an indication of what she has in mind for me. Bright pink, with girl power emblazoned on the chest. I shrug my shoulders, she is in one of her moods, so all else is irrelevant until she gets her way. I am driven to a salon on the edge of Phoenix, very near to Arizona State University. I grab the car door handle, holding on tight shaking my head no before she can say anything. She turns me toward her until I have to look at her face.

“If you remember I helped pay your expenses for your schooling. Today is some of my payback for that feat. I have taken time off from work to help in your presentation so you will embrace this totally, do what they tell you to do, then attend the interviews this afternoon and do your best to sway them into hiring you. If this fails I will leave you alone for a couple of weeks so you can try your way. After that we will stop and talk about what next. You need to enter the salon, ask for Stacey and do as she says. This can be accomplished with your cooperation or I can handle it other ways, but you will end up doing as I wish today. Now are you going to cooperate, or do I need in employ other methods?”

I swallowed hard, opened the car door and got out, I watched as she drove off, leaving me in the hands of Stacey. I had a pretty good idea of what Sis wanted for me, I was not particularly happy about it, but she did pay a lot of my expenses at school, to insure that I got the education I wanted. I walked through the door and asked for Stacey. As she approached from the back I got my first look at the sign on the back wall of the salon. Curls for Gurls in bright pink letters almost three foot high. Another sigh, I am sure of my earlier thought, it will be a very difficult day for me. Led back to a separate room and seated in a stylist chair. The chair is leaned back and my hair is washed and conditioned. A towel is wrapped around the wet hair and the chair is set back upright.

Not much conversation from Stacey, she seems really focused on what she is doing to me. I ask a couple of general questions of her, she smiles and responds then surprises me with her next statement. “Jean said you would try and engage me in conversation so that some of what is planned could not be finished in time. I will gladly talk to you, but you will be done in time for your appointments, that I can guarantee.” I sighed, Sis knows me well, and is apparently determined to get her way today at all costs.

Stacey separates the hair into sections pinning the sections to my head. Then she works through each section combing it then cutting it to the proper length for the style. She does engage me in conversation from time to time, but is determined to finish her tasks. She did ask what college I went to and what I studied. After making it through all the sections she wets the hair with a spray bottle and then starts winding the sections into curlers. Yep what I feared is happening. I asked nicely what style she has been requested to give me. She giggles, I see your sister, Jean, has not told you anything, so why don’t you just wait and be surprised. I am sure you will look fantastic, much better than when you entered the salon.

With a head full of curlers I was expecting the hair dryer, but I was led to another room and laid on a table. I was furnished a small pillow, keeping the hard curlers from pressing against the table. My sweats were removed, then my shorts, now naked and feeling very vulnerable on the table. A cream was rubbed all over my front, including junior, then thirty minutes later wiped off. With it what little hair I had been able to grow came with it. Now as smooth as a baby, I was turned over and my back side handled in the same way. That apparently included my rosebud, a very humiliating experience indeed. Luckily, I was facing down, the red on my cheeks shared only with the table.

Next was my eyebrows, this time hot wax was used, most of my eyebrow coming out with the first pull of the cloth strip. Looking in the mirror at the end of the room, that side of my face is definitely feminine. Once the other side is handled there was no doubt that Oliver had gone missing.

The name Oliver was a moniker that I truly despised. I did everything I could to get people to use anything else instead as I grew up. Oli, O.J. and several others got limited use, my sister Jean had always used Olivia, knowing that I hated that too, so I pretty much went through life answering to anything except Oliver and I do mean anything.

Back on subject, now that I was hairless, with a feminine face, the feminine hairdo that I figured was coming would fit right in the scheme of things. The hair dryer was next, forty minutes of warm air blowing over me left me drowsy and not with the program. Stacy removed the curlers, the large curls falling out all around my face. I knew at that point it would be worse than anything I had envisioned.

The fact that I was setting in her stylist’s chair naked as the day I was born with just a cape around my shoulders left me bewildered and confused. The curls were manipulated into an ultra-feminine hairdo, with curly tendrils at the back of my hair and over my ears. There was no male image in the mirror, nothing but gorgeous female to be seen. Several diamond encrusted barrettes were added to the sides of my hairdo, keeping the hair on the side of my head tight and smooth.

As I looked into the mirror again, my sister Jean appeared with a garment bag over her shoulder. I looked for the clothes I had worn to the salon, they were suspiciously missing. Another sigh, what she has for me in the bag is my only choice apparently. Then I thought back to when we left the house, my wallet, keys and credit cards and ID all left at home. Another big sigh, I guess it will be her way today, all other choices now seemingly unavailable.

Her choice of clothes was worse than I expected, an Ivory ladies suit with a pencil skirt. I gave Jean such a look, but she was holding all the cards. My cape was yanked off, and a pair of panties was handed me. I thought about it for a minute, then when she held up the thong panty, I slipped the ones I was handed on quickly. A bra was next, thankfully not sexy, although it was an underwire. After she helped fasten the clasp behind my back she came around front and reached into the cup and grabbed some flesh and pulled sharply up. A lot of the flesh stayed in the cup leaving me with a noticeable bust. A slip came next then the skirt. A lacy blouse was added, then she showed me how to slip the blouse under the waistband of the skirt. The jacket next, then the cape again as Stacy added some mascara then some blush to my cheeks followed by several coats of lipstick.

The cape removed, then I was hustled out to her car. As I sat in the passenger seat I was handed a purse, looking inside I found everything I might need, the list of interviews and several copies of my resume and college transcripts. I did notice that my wallet was devoid of cash and credit cards, although I did have my ID. No keys to anything, apparently a car and the house were off limits until I had attended the interviews.

I gave up, might as well do as she wants, any other options or choices seemingly denied me. Twenty minutes later I was dropped off at the first place on the list, I was to see a Ms. Townsend, take a test or two, then have the interview. I found her office, her secretary handing me the test and showing me to an unused desk. It only took me a half hour to complete the test, the secretary graded it and then took it to her boss. A few minutes later I was called back and spent the next hour being interviewed. None of the questions were difficult, I was expecting most of them, so I gave quick concise answers. I think I did well, Ms. Townsend said she would call me later today after she had reviewed the test and interview questions.

That sounded familiar since we were taught that approach in school, a way to evade telling the applicant that they cannot use them. Jean was waiting for me when I exited the building, and promptly drove me to the next interview. I was again dropped off in front of their offices, looking at my list I was to see a Mr. Johnson at two o’clock. I was a few minutes early so I waited in his outer office.

No test this time, just him going over my resume, my classes and the recommendations of some of my professors. I doubt he was interested in me other than my apparent gender. Several times his eyes was on my chest and not on me the person. Even though I had little up top, it was enough to occupy his interest. Jean was waiting again, this time a longer trip to Scottsdale and my next appointment. This time another female, a Ms. Walker was the one to see.

I was surprised she didn’t even look at my resume, my letters of recommendation, or the classes I took in school. Instead we walked through her company offices talking to employees and what projects they were working on. Several times I was inserted in the conversation, asking an opinion or how I would tackle the problem. We ended up in their accounting department, where she introduced me to Julie the head of the department. Several examples of their accounting were shown to me, I looked them over then made a suggestion to them. I figured that was why I was in the department in the first place, them wanting to know if my knowledge was all from a book, or based on real life circumstances.

All during the conversations I had the funny feeling that Sis was in on this, the way the interview was handled, and that none of my pertinent details had been looked at. I imagined she had approached this lady, laid everything out and waited to see if I would be chosen. Maybe the lady owed Sis something, a favor that she was calling in. Not the first time something like that has happened, with Sis involved.

Back to her office, I was shown to a seat in front of her desk. I sat properly as befits a female in a skirt and decided I needed to confront her and find out how much Sis had to do with this.

“Ms. Walker, just exactly what has Jean and you discussed. I am not that mentally challenged that I can’t figure out she has quite a lot of input in this before I arrived for the interview. I want the job, but based on my merits and not on what Jean has told you. If that can be accomplished I will be glad to work for you.” I got a huge smile from her.

“Okay, let’s lay all the cards on the table. Yes Jean has talked to me about you. What she has clearly stated is what I have seen in person today. I know of your true gender, how you are dressed today is actually a request of mine. For the position I have in mind for you, it is essential that you present gender female. I wanted to see if your presentation as a female is adequate for the position. If I were to offer you the position with those requirements would you be interested?”

“I might be interested, depending on the reason that I need to present gender female. Heavens knows I have had enough practice due to Sis’s involvement in my life and I am sure it would tick several boxes for Sis if I did take the position. Now for the reason that I would need to portray a female at work. Inquiring minds want to know.”

“Several years ago this company was a family owned and operated business. The grandfather was the CEO and served as such until he was in his early nineties. There were members of the family that he did not want in any supervisory positions. These were mostly males, including his second son. At one of the board meetings he amended the progression of the company if he died. Any employees in a supervisory position must portray the female gender 24/7 or be excluded from any and all dividends or stocks, no exceptions. His one daughter was who he wanted to follow him as CEO, so he figured that would ensure his wish. Of course, the son tried to legally fight it, he thought the position was and should be his. The attorneys for the company won out, and he moved away in disgust a few years later after spending most of his inheritance fighting the rule.”

“It has worked well for the company, a lot of infighting and jockeying for top of the heap never materialized. When the daughter retired she made sure that the owners of the company stock were all like minded, and even though we have had several challenges in court the rule has persisted. Incidentally the entire stock of the company is owned by females, daughters and granddaughters of the two CEO’s. The present position is filled by an outsider, a quite capable and smart young woman hand-picked by the daughter.”

“In simple terms if you want the job, you are going to be living and working as a female for the duration. My opinion I think you will do quite nicely, your actions and ideas today proving my theory. I see before me another young woman, intelligent and gifted wanting to make a success out of her career choice, I think here will be an excellent place to start. No telling where this may take you.”

I asked her if I could think about it overnight, then get back with her. She smiled, apparently the exact response she was expecting from me. We shook hands, then she invited me to return tomorrow at nine A.M. tell her of my decision and maybe work a day to see if what she has in mind for me is something I can live with. I was handed a stack of forms to be filled out, and told to just fill them out and return them to her in the morning. I guess everyone expects me to take the job with the required dressing as a female requirement. We shook hands and she welcomed me to the company as she held my hand and squeezed it, her huge smile conveying the fact that she knew I would eventually accept.

Back out front as Jean was waiting for me, that same smile on her face as on Ms. Walker’s face when I left her in her office. I had kept the forms I needed to fill out in my purse, not wanting Jean to see them . I was quizzed immediately if I got the job, I sighed and told Jean I had to continue the interview in the morning, then I will be told of her decision. It was already quitting time so I doubted Jean could call Ms. Walker to confirm my story. On the way home I was asked lots of questions, Jean trying to find out how I had screwed the interview up. I imagined once home the interrogation would continue, Jean obviously miffed at things not working out as she had intended. I had a hard time controlling a smile and giggle that was just below the surface just waiting to bust out.

I did get questioned for most of the evening, I could tell Sis was frustrated, my answers not adding anything to the equation. I contemplated trying to keep her from finding out that I was offered the job for a longer period of time, since this banter back and forth was fun. I did fill out the forms in my bedroom that night, deciding that the job offered was better than anything I might be offered to my male persona. I thought often about the requirement to dress as a female, then looked down at my body, suddenly realizing that I had stayed dressed as a proper woman in business attire all day and had managed to live though it, truth be known I actually enjoyed the time dressed, even straightening my hair do and applying another coat of lipstick after we ate dinner.

I knew I had a sharp learning curve to accomplish in the next few days, I though I could handle the clothes alright, but doing my makeup and hair everyday might be a bit more than I could master in the ensuing days. I definitely wanted to work a day or two at my new job, making sure it was as described and that I could handle it easily. I think my main concern was if I could handle the female portrayal, not if I could perform the work.

The next morning I got dressed earlier than I had told Sis my interview was for, slipping out of the house as she was just getting up. I had found a tan suit to wear today, the only heels that matched color wise were five inches tall. It took me several trips around my bedroom before I felt confident enough to wear them out.

I had arranged to borrow her car, since I knew where I was headed and had nothing else on the agenda for today. I had just arrived when Ms. Walker came into the office, I got a huge smile, as she apparently liked employees being prompt. I apologized for my looks, telling her that I needed to learn some more about makeup and hair styles, something I intend to do in the next few days. I was told that my appearance was satisfactory, no worse than a female having a bad hair day.

I handed her the completed forms asking her if I could work a day or two to see if it is something I would like while hopefully able to contribute to the company some. She processed my forms, filled out my social security forms and had me sign them, then led me to where I will work today.

For the first day I was placed in my own office, given two very sizable stacks of data and shown how they needed to be added to the accounts data base. Although it was such an easy task, it allowed me to see some of the economic aspects of their company and not be overly stressed out at what I was doing. I did find several mistakes, gathering that information up to give to Ms. Walker later. The morning flew by, doing something seeming to occupy my mind, allowing me to forget that I was dressed as a female out in this world.

I took my lunch at the appropriate time, using a fast food place a few blocks from work. I ate in their dining room, then fixed my lipstick as if I had been doing this my whole life. When I got back Ms. Walker was waiting for me, wanting to know how I was progressing. I showed her the mistakes and then the corrected data. As she left to go back to her office she had such a smile on her face.

I finished the data entry by three, and went to find out what next. She handed me a disc with all of the companies information on it, asking me to give it a scan so I could see what was involved in their operation. It had their current relationship with several customers on it, along with info on most of their other customers. I spent until six that day looking it all over, making several notations where I thought some changes might improve their profitably and noting one glaring mistake that needed to be corrected. As I was straightening the desk I used and gathering my purse Ms. Walker came in and set in the chair in front of the desk I had used. I showed her my recommendations, then the mistake and noted that I had corrected it, the new figures printed out on a sheet for her to see. She looked it over, then suggested I head home, she wanted me back tomorrow at eight A.M. where she will show me to my office and introduce me to my staff.

I was hugged as we left the office, her telling me that she would not take any excuses from me. I will be into work tomorrow and that is final. She gave me a hug and went back to her office, while I headed to the parking lot and my car. I made the wild assumption that I had been hired, a smile coming to my face. The drive back to Sis’s home not taking near as long as the trip into work this morning.

When I entered her house Sis was right there wanting to know how things worked out today. I tried to play it down, telling her I needed to make a few more copies of my resume, and ditch the female attire, getting with the list of employers the school had given me. I thanked her for her help, but no one was interested in me as a female and working for them.

Well that approach lasted for a whole five minutes as she stared at me, then when a smile started on my face, she hauled off and hit me hard. I was rubbing my arm as she dragged me to the couch by the ear. Pushed me down on the couch and parked her tush right next to me. Her look of frustration quickly had me divulging all before she decided I needed another remainder of her strength. Once all was told, she grabbed my hand and we were off. Out the door, in her car and at the mall before you could count to a hundred.

Up and down the mall, as she expanded my wardrobe to the nth degree. I had to make several trips back to her car laden down with bags, shaking my head as I did so. I will have to work a year to just break even. It wasn’t just taking my new things to the car that afternoon, I had to try each piece on, making sure they fit properly and looked good on me. By the time she decided I had enough for the first week I was pooped. Fifteen business suits plus skirts and blouses for after work. I would have to change suits twice a day to be able to wear them all during my first week at work. I did mention that thought, but Sis did as she always did and totally ignored my thought.

Up early, getting my bath and making sure I was presentable. Selected my underwear and put it on, having to take in a large breath to keep from making a mess in the panties. I got the suit on over an ivory blouse that allowed my bra to show through. When I tried this suit on at the store I don’t remember it being this short, I presume it shrunk as it hung in my closet overnight. I though Sis might have gotten up to send me off, but she had other ideas. Since I was dressed as a female her job was satisfactorily completed, so an extra forty winks was called for on her part.

At work I was shown to my office, introduced to my staff, then she went over some things she wanted accomplished from my group. Nothing was complicated, I assigned the work based on the short history they had supplied when introduced to me. They seemed to be a good group of employees, all of them pitching in to get the job done. I checked on them often, pointing out a few things I preferred in what they were doing. I got looks of awe, apparently none of their previous bosses looked over their work, or made suggestions on how it was presented. That was probably why there was mistakes present in some of the previous work.

Since they had done real well this morning I offered to take them to lunch, my treat. I had seven females with mouths open, staring at me. I had to make the offer twice before it made it through their shocked mind. I tried to convey to them that we are a group, not single employees out to climb to the top, no matter how many people we had to climb over to get there. After lunch I noticed a difference as they started working with each other and asking questions of each other. I smiled as I went back to my office, maybe just maybe this job will be alright.

I did notice later in the afternoon that I was fixing my lipstick and powdering my nose if needed. Something never mentioned to me or taught. I guess my trial in the female gender can be called an unqualified success, since Olivia has been totally assimilated. I hope Sis will be as happy as I am, a female for the rest of my life.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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