Rylie; Accepting A Female Challenge

My Aunt had made the offer years ago, an attempt to get the male of the species to appreciate how different it was for a female to live and work in this world. When she first announced the offer it was in all the news media, our local paper doing a whole section on the female lifestyle, the inequalities between the sexes, anything and everything connected to the challenge. That is how Aunt Julia had made the offer, as a challenge.

The challenge was simple, live and work as a female for a year with no financial support from anybody else. Complete that year and she would award a four year scholarship to any University in the country and a quarter of a million dollars tax free. There were rules, of course, fifteen pages of what is required for the challenge.

The challenge was open to any male high school student that had graduated in the last three years and had a 3.0 grade average. The male had to be between five foot six and five foot ten, weighing between 140 and 170 lbs. and relative normal in body build and appearance. The male had to possess an androgynous figure, one that when feminized would have the ability to pull off the challenge at least physically.

Everybody in the state knew of the challenge, Julia was well known, active in politics and head of a multi-national corporate entity. The challenge had been issued ten years ago, no male having the nerve or possessing the minimum requirements to partake of the challenge. The requirements were not the problem, the nerve required to follow through on this challenge was the problem.

When the challenge had first been offered I had just had by eighth birthday. Of course, at that time I had no interest in it, don’t even remember anything about it. As I progressed through grade school and high school, several times it came up, was discussed and quickly forgotten. I was now in my senior year of high school, with college and my future career choices paramount in my mind.

I would probably be described as being almost a radical, favoring different viewpoints and lifestyles often. My opinions never approached anything mainstream, the wilder it was the more likely I would embrace it.

It was at a family Easter gathering that Julia and I had out first significant exchange of words. I had met her before, several times as I was growing up. My Mom and her were less than the best of friends, I think interest in a boyfriend, that both were enamored with in college caused the split. Since then they were civil to each other, but there was no close bond between them.

At the family dinner, someone brought up the challenge that Julia had issued years ago. Her daughter gave her opinion on the topic, believing that no male had the where with all to make it as a female. Then if he did accomplish the physical part, living as a female would be his downfall. Being the instigator that I was, that statement required a comeback.

I made my opinion known. “A female’s life is so simple and basic, that it wouldn’t even be a challenge to live as one for a year. Looking pretty and having a male support and fawn over her is really all it’s about.” As soon as I made the statement Julia had a smile plastered on her face.

“Well we seem to have an applicant for the challenge, if you believe what you say, fill out the application and we will get started. You seem to possess most of the qualifications, so what do you say?” I noticed some snickering from some of the girls around me, then several disappearing upstairs with my sister suddenly.

The topic did progress to other subjects, I made my way outside to the patio, to escape more boring conversations. It was twenty minutes later when Sis and her entourage approached me. Several sheets of paper were set down in front of me, along with a pen. I glanced at the paper, an application for the challenge. I blushed a little, but Sis and her friends set down next to me and started filling out the application. I answered a few questions, Sis handling some of the answers I was reluctant to divulge. That had always been her goal in life, to make her brother’s life as miserable as possible.

Then when it was completed, one of her friends went and brought back Julia. She glanced at the completed application and smiled. Looks like we have our first qualified applicant for the challenge. I have to run it by the committee, but I think it will be approved. Now once approved you have a four week acclimation period, then your year starts. The foundation allows fifty thousand dollars for your transformation, wardrobe, makeup, and you first month’s rent on a house or apartment. After that you are on your own.

I will have my secretary notify you of your acceptance tomorrow after school is out. Your four weeks start then. I suddenly realized that I will be a female for the last of my senior year of high school, or at least partially so. I tried to find an excuse to back out, but my sister’s friends were already texting my acceptance to all of their friends. I am sure by tonight the whole school would know. I pulled Julia aside and told her that maybe we should think this through before I accept. Her smile said most of what I need to know.

“I have already accepted your application, so once the committee accepts you are ready to go. I am sure that is only a formality. You need to make your plans, all that happens is up to you, no help from anybody, since females have it so easy, I doubt you will have any problem in your quest for femininity. I am sure your male superiority and knowledge will have you sitting pretty within a few days.”

I retreated to the bathroom, I now had to go, maybe my nerves were getting to me. I know any confidence I had as Rick had vanished. I tried desperately to think of some way to get out of this, but nothing came to mind. Then the rest of the disaster came to mind. A young female with no job skills, only a high school diploma, and living on her own. Luckily I was in the bathroom, my Easter dinner came up with a vengeance. I cleaned up some, made my exit and headed for my room. I had no interest to see or talk to anyone else today. This disaster occupying any brain cells that were still functioning. The fact that I walked into this proving that I had very little activity up there anyway.

I was ignored, thankfully, until I went downstairs right before bed to get a glass of water. Mom was sitting there, doing some of her paperwork from her job. She pointed to the chair across from her. I got my water and parked my butt on it. She took a few minutes to compose her thoughts, then laid it all out for me. “You are of the age that you can do what you want in life. In this matter you have bitten off more than you can handle. Once Julia gets back to you, the commitment is there. The female life might look easy to you, but that is far from the actual fact.

I suggest that you research this very carefully, not like you do for a school project. I would like you to succeed, but it will be a hard life to master. You do realize that we can’t help you once this starts, a single adult female for a year. One of the caveats is that the starter money has to be returned to the foundation unless you complete the year. That is fifty thousand dollars that has to come from somewhere. I will be glad to help you with advice if you want me to, but I expect you to fulfill your commitment to the fullest.

Maybe a little restraint might have been a better way to approach this. You have always spoke first and thought about what you said much later. Good luck this time. When I was pregnant with you, the name I had chosen for a female would have been Rylie if you want to use it. Keep me in the loop and I sincerely hope you learn something from this, otherwise it is going to be a long miserable year for you.

The next day I was at school physically, but mentally I was not within miles of the place. Shortly after the last bell rang signifying that the school day was officially over I received a call on my cell phone, I was to come to Julia’s downtown office as soon as possible and they would get me set up so that I could start. I didn’t respond, my knees were almost to give out, my nerves were fried and I was beginning to sweat. This can’t be happening to me.

I decided to go down there, plead insanity and confess my stupidity and end this farce. The drive downtown seemed to take forever, the fact that I almost hit a car at one of the intersections proving how out of it I was. I took the elevator up to the fourth floor and told her receptionist that I needed to see her. She came out to get me a few minutes later, that sickening smile of hers in full display. We set on one of her sofas to the side of her office and I started pleading my case immediately. She didn’t say a word, listening to me, but her smile remained unchanged. I finally wound down, waiting to see what she might say.

I was handed the check, as I was trying to give it back to her. “Rylie you need to listen to me, keep quiet and I will tell you a little story. Once upon a time there was a male like you, had some reasonable intelligence, but still acted like you did today. A close relative offered a similar deal to him and after a great deal of soul searching he accepted it. The first few months were a disaster, he got thrown out of his apartment, lived on the streets a few days making a total mess out of his life. Somehow he managed to correct a few of the problems, a lady felt sorry for him offering him a job and a place to stay. He decided he wanted no more of the poor life and started to apply himself to everything he did.”

“Fast forward eighteen years to the future. I now have the chance to allow another member of this family to learn and experience life from the viewpoint of a female. I will not allow you out of the challenge, you are committed now a year to experience the joys, frustration and tribulations of a female. Think things through, forget about the rewards at the end, concentrate on the life and you will be richer and happier as a result.”

I was trying to understand what she was saying, wondering who this person might be. Then it hit me, Julia is this person, a former male in her life. She always impressed me with her knowledge, but most of all by her confidence. Never a doubt in her decisions, her actions never doubted by others. I tried to see the male underneath, but there was not a single sign that hinted that she was ever a member of the male sex.

With check in hand I dragged my butt out of there, well let’s just say that I made the trip to her office door faster than I thought possible, someone’s hand in my back pushing pretty hard. The reality of all of this was making itself known. Where do I start, four weeks to get transformed into a female, find somewhere to live and clothe myself? Finding a job as a female, to support myself now seemed to be impossible. Prior to my stupid remarks I had already explored the job market as a male, not finding anything remotely close to a job that I could support myself with. Now add in the new female gender and I could see where I had really screwed up.

My mind kept coming back to Julia’s confession. I wonder if her story was true or just something fabricated to get me to stay in the challenge. Before I had left her office I had repeatedly tried to get her to take the check back. Her simple comment was it is made out to you we can’t take it back. Since my stupidity was still with me after the fiasco yesterday, the fact that she could just void the check never entered my vacant mind. I made my way home, having to face Mom now on my mind. I entered the house and announced my arrival. She called out from the hallway so I made my way down to my bedroom. She had boxes spread all over the floor, packing up my clothes. Several were already sealed up, labeled Goodwill.

My legs gave out and I collapsed to the floor. My clothes gone, my life as Rick over and it has been just a day since the disaster that now dominates my life. She helped me to my feet, gave me a hug, then suggested that I get on the internet and start making plans. She pointed to three outfits on the bed that will carry you through to next Monday, Goodwill will be by tomorrow to pick up your things. “This will take all of your limited intelligence and all of your perseverance to make a go of this. Drop the huge male ego, delve into this with some desire and just maybe you will survive.”

I looked at her, mouth partly open, wondering why she was doing this to me. I had a month to get this all together and this is only the first day. Oh, I need the clothes you are wearing now, so strip. You have work to do and I need to get these boxes to the garage. I started to take off my long sleeved t-shirt, but my arms got tangled in the sleeves. Actually Mom was holding the ends of the sleeves together so that I couldn’t see what she was doing. While I struggled my pants were down at my ankles and my boxers soon followed. She jerked my sneakers off, grabbed my pants and boxers and left the room. I set on the floor naked except for a pair of socks. Before I could do anything she was back with a dolly, loaded the few remaining boxes and grabbed my socks. Now naked in my room with nothing masculine to wear. I leaned up to see the three outfits she left me, shaking my head as I settled myself on the floor again. Talk about a disaster this one is shaping up to be a doozy.

I was getting cold, the AC running like always, but the lack of clothing of any kind leaving me chilly and covered in goose bumps. I got up, checked the outfits on the bed, then slipped on the panties, followed by a long dress, one that was almost to my ankles. It helped with the chill, but one look in the mirror confirmed that I had a long way to go to look even remotely like a female.

Another hour was spent wallowing in my misery, then I managed to get to my computer to see if there was any help out there for my situation. I typed male to female in the search box and I got one million three hundred thousand possible matches. The Turnabout Gurl Salons were number three on the search, their ad saying they could easily convert a male to the female gender, offering help, advice and even wardrobe choices to prospective gender benders. I called their local branch, talked with one of their consultants and ended up agreeing to an appointment early the next day.

I slept in my panties that night, that or a dress the only choices available to me. I felt all alone, I knew Mom still loved me, but her packing up my male clothes before I even got home from Julia’s office seemed harsh. Then I thought of what Julia had told me, Julia had been Mom’s brother, so this is not the first time she has been through this.

I did make the appointment on time, a shirtwaist dress my choice out of the three outfits at my disposal. No makeup, but I did manage a brush through my longish hair. The image of me in the mirror was far from feminine, but maybe I could make it to the salon without getting beat up.

As I entered the salon I breathed a huge sigh of relief. The bus ride was okay, although everyone was obviously staring at me. I know I heard a lot of whispering, most of it as they were looking my way. I was taken back to one of their private rooms and a distinguished lady came to talk to me. I told her about the challenge, about my efforts to get out of it and also about Julia’s insistence that I would do it no matter what. The lady suggested that I remove my clothes, let them do a full body scan, then she could advise me of my choices and the cost involved.

I reluctantly complied, as the panties slid off my legs I was instantly beet red all over. The lady approached helped me to stand erect and in the proper position for the scan. The machine came to life, and soon my image was projected on a screen on the far wall. I was given a robe to slip on, then she went over each treatment and the computers projection appeared on the screen. Several treatments and the image displayed was female.

She continued on, till she had covered everything the salon offered. Then a printer to the side of her desk came to life and it printed out the cost of all the treatments. I was handed the sheet, my eyes bugging out at how much it was going to cost to become this female. The figure for the clothes alone almost twenty thousand dollars.

She suggested that I give it a lot of thought, then come back tomorrow and talk to her. She is sure something can be worked out. I left in a daze, I might be able to obtain the look, but living as a female for that year now was the problem. Obtaining a job would be a necessity, there would not be enough money left to handle rent, food, and other female needs.

Story Incomplete At Present

© 2016 thru 2021 Fran Cesca Walker

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