Our family situation had suddenly deteriorated. This morning Mother got word that her husband had died in an ambush in Afghanistan. That news was delivered by an Army Officer shortly after nine A.M. He relayed the news asking if her if he could notify anyone else to come and stay with her. She declined, then he asked if she needed help in explaining to her children about her husband and their father. She again declined, letting him out of the house a few minutes later.
I had heard the exchange from the top of the stairs. The military vehicle pulling up outside had piqued my curiosity, so I had moved to the top of the stairs to listen. Father and I were never close, for one thing I hardly saw him. He was military through and through, obtaining the rank of Major a few years ago. Come February it would be twenty-six years in the Army. Those years included three deployments to Europe, one to Southeast Asia, although he missed the Vietnam conflict totally. This supposedly was going to be his last overseas tour, already accepting a position with a defense contractor. All that meant was I wouldn’t see anymore of him later than I do now. I did shed a tear, what his death will do to the family now my main concern.
Mom was there for us most of the time, but her way of coping was to immerse herself in her business. Shortly after our birth, she had hired a nanny and that is who had raised us to our present seventeen years of age. I was one half of a set of fraternal twins, Tricia my sister being eleven minutes older than me. I got stuck with the name Trinity, according to Mom she had just spent eight hours in labor and James her husband was anxious to name the kids. He gave the nurse a couple of names, but soon after he left Mom told the nurse to use Trinity and Tricia, names her own sister had given her when she found that she was having twins. At the time the sister didn’t know that one of the twins was a male. James had a fit later when he found out, but by then it was too late. Even back then the bond between Mom and Dad was weak and deteriorating.
Jennifer, the nanny, was the one to raise us, helping us through life. She was the one we saw in the morning to get us ready, to make our meals and to help us with our homework. I don’t remember much before school started, I knew she was hired as a nanny shortly after we were born. She lived in the house with us, but I feared with Dad’s death all of this might change.
Jennifer and Mom met quite often over the next week or two, always behind closed doors. We were not included, even though we were nearing the legal age of an adult.
Sis and I were struggling through high school, so our time was pretty much taken with studies. In fact, without Jennifer’s constant help, I doubted either of us would have passed our junior year. Now only four weeks remained of our senior year, Tricia had done all right with her studies, but I was close to failing in three subjects. French, Geometry and World History were my bug a boos, causing me to fear the end of the year finals. We weren’t exactly dumb, but any lessons or learning always came with lots of struggles, especially for me.
My problem was I saw no use for what I was learning. I knew I would not be a part of the business world like my Mom, truthfully I couldn’t see myself in doing anything worthy of some type of reward. I hadn’t given up totally yet, but I was close.
After all the conferences with Jennifer, Mom had went to Europe, her business had several branches over there, apparently needing her guidance now. That left Sis and I with Jennifer. We could tell things had changed somehow, but no word on what was happening. Among other things I noticed a slight change in my clothes over the next few weeks, my jeans were tighter and the tops soft and silky. I mentioned it to Tricia, she just told me it was probably a laundry problem. Jennifer was there, but spent hours on the phone with someone. Maybe Tricia is right, a simple explanation that there was no one to do the laundry.
It all came to a head the first Saturday of May. I was already looking forward to the upcoming summer, some relief from the books and school. Jennifer called us down to the living room, asking us to find a comfortable seat. I immediately had bad feelings about this. After we were comfortable, she started with her little speech.
“Due to the nature of her business, your Mother is going to move to Europe, most likely Paris, France. This house will be sold, the money needed to pay down some of the debt that your parents had. Now we come to you two. Your Mother prefers that you stay with someone here stateside. Due to the family finances I will no longer be kept in the nanny position. Your Mom feels bad about this, but doesn’t know what to do about it. I suggested that you two live with me, something I would be quite happy with. I have found other employment at a private school for young ladies, a two year finishing school. The courses are geared to developing manners, confidence and finesse in the young woman, not necessarily book knowledge.”
“The school is furnishing me living quarters and free tuition for my children. I have talked to your Mom and her attorneys and we have come to an agreement to let me adopt you two. It isn’t because she doesn’t love you, just a way for you to be able to live with someone and continue your schooling. Actually she is lost, not knowing exactly what to do. We have talked about this many times, I tried to get her to be with me when I explained this, but she fears you will end up hating her and doesn’t want to face that possibility.”
“For Tricia there is no problem, however Trinity will have to live in the female gender to be able to take advantage of the schooling. Trinity, if you haven’t noticed I have changed a few of your clothes recently letting you experience some female clothes. You seem to adapt quite well, and in most cases nobody made any comments. One teacher called me about your female blouse one day, I told her you just grabbed the wrong top when dressing. I want both of you to talk this over, then tonight we will discuss this again.”
“I have always loved you two, and thought of you as my children. However, this is a lot of changes for everyone, so I want you to be sure that this is what you want. Save your questions for later and we will talk about them all, as a family. May I suggest a nice long walk in the woods, there are several places where you can stop and reflect on what I have told you. Dinner will be at six and then we will talk until we settle on something.”
Tricia always the decisive one grabbed my hand and we were outside in a matter of minutes. She started off for the trail that led us through the woods, ending up at a stream that filled a lake on a small plateau. She talked to me as we strolled along, her opinion is that we stay with Jennifer. Although not our birth Mother she has raised us for seventeen years, been there for us and openly expressed her love for us on many occasions.
Mom being unsure what to do, is a big question mark too. The fact that she spends so little time with us, not a good recommendation for our care giver. The fact that her home will probably be in Europe also a point to consider. After we got to the lake, we settled on an outcropping of rocks and stared at the ripples in the water. She leaned a little closer and hugged me. “I will love to have a little sister, much more fun that a bratty brother.”
I gave her a mean look and we both dissolved in giggles. Quiet for a while, both of us lost in thought. The only sounds were a couple of frogs or toads practicing their tunes for tonight. My mind was focusing on the female gender part, that along with learning to be a polished and sophisticated female, maybe not the best future for a young male. That for me might be the deciding factor, then not being with Tricia something I didn’t want to face either.
We talked a little more, but we decided to go with Jennifer, after finding out a little more about my role in this. Was it just dressing some or was it living the life of a female completely. The thought of living with Mom sending shivers down both of our backs. The fact that she chose her businesses before us a sure indication of her feelings for us. She might have gave birth to us, but her actions since have fallen way short of a caring Mother.
We meandered back to the house, Tricia dragging me upstairs to her room. As soon as we entered she asked me to strip. I had a feeling that she might try something like this, maybe a trial run would be good. I turned away from her as my shorts hit the carpeting, but she just turned me back and handed me a pair of panties. I slipped them on, biting my lip hard to keep from groaning in pleasure. Next came a bra, apparently one of her oldest ones since she is quite developed now. Her breasts now would not come close to fitting in these cups. A dress, a simple shirtwaist dress, with a flowing skirt in shades of pink and yellow. Then a pair of her flats, capped off with her putting my hair in a ponytail.
The image in the mirror was feminine, a few traces of the male persona still visible, but on first glance a female is all you see. Before I could take in my image Tricia dragged me out of the bedroom and down the stairs looking for Jennifer. I screamed bloody murder, but by the time she eased up I was standing in front of Jennifer, embarrassed and quite red in the face. If I had been a normal male I might have been able to hold my own with her, but Tricia has always been the athletic one, playing any sport the school offered. I was the official class weakling for the school, one that had a hard time pulling a door open by himself.
Jennifer moved towards me, enveloping me in a tender hug, I was leaking tears, not sobbing, just drops of water sliding down my face. Tricia wanted in on the hug too, stomping her foot in frustration. Jennifer pushed me back a little Tricia squeezing herself between Jennifer and I.
I liked that even more, the two people I cared for most in my arms. We held the hug for several minutes, then Jennifer led us to the kitchen and we got to help her make dinner. Tricia was all thumbs, both Jennifer and I giggling at her antics. Her task was to stir the pot of Chili on the stove and keep it from sticking to the pan. Well, a few minutes later a good portion of the chili was already stuck to the pan, she had turned the heat up on the burner, when she was supposed to turn it down to simmer. I stepped in, unsticking the majority of it and turned the burner down all the way. Then I finished helping cut up the salad, our complimentary dish to the Chili.
Tricia might need the finishing school, finding someone to support her, should be a prime directive. She is not going to be the mother type caring for a family and children. Jennifer asked us for some of our thoughts, to see what might be on our minds. We both mentioned Mother picking her businesses over us. Jennifer explained that is all she knows, never interacting with children, her knowledge of their needs and wishes nil. In the corporate world she knows what to do, and how to make it succeed.
“I have been with kids most of my life, raising my sisters when I was younger because Mom had to work. Then I came here and helped to raise you two. In the corporate world I would be lost, not knowing where to start or how to do it. So don’t be too hard on your Mother. She really is lost on what to do and how to achieve it.”
I then asked how far the gender thing was going to be carried out.
“That is a hard question to answer. I presumed you wanted to be with your sister. The two of you are very close, always seeking out the other for comfort and advice. To achieve that and get schooling for you it will require you to present as a female. That most likely will lead to living as a female. I don’t see you having any trouble doing so, your soul is female, always has been. If you count on your hand the number of male friends you have had during your schooling you will come up with a big fat zero. You maybe don’t have close female friends, but you interact with the female comfortably and they are comfortable around you.”
“I have always thought of you two as sisters, the way you act, your interests, and how you talk to each other. If you will try it, I will be delighted to have two daughters, to love and help them become young women. It will be all new surroundings, new people, and new experiences. I have every confidence that it will work out, but if it doesn’t I will do all in my power to help you become who you want. Unfortunately, that will probably be without Tricia at your side.”
In the end we decided to go with Jennifer, a much more secure life for us than with Mom. I helped Jennifer clean the kitchen while Tricia emailed her friends telling them of our departure early next week. Jennifer suggested that I dress as a female from tomorrow on, the practice necessary before I am enrolled in a girl’s finishing school. For the next few days of school I wore gender neutral clothes, my male clothes at home being donated to Goodwill. When the day arrived that the truck came to pick up the donation I was almost in tears. I kind of looked forward to the new school, but the finality of my male clothes disappearing was indeed a shock to the system.
I got over it though as we packed for the move to Jennifer’s residence. It turns out that her employment is as the head counselor for the school. She later confided in us that she has a Master’s degree in Psychology and the same in childhood development. Who would have thought? To us she was just a Mom, loving and caring but determined to see us become well educated young adults. Two weeks later we left our old home, headed to new adventures.
The school was quite large, spread over fifteen acres, most of the students were boarders, living in the three dorms on campus. There were five residences on the campus, the headmistress, the assistant, two of the professors and Jennifer’s. It was huge, two story and quite resplendent in appearance. We took a day or two to move in, then Jennifer started on her duties. Tricia and I just stayed busy trying to get the rest of our things put away.
Both of us were taken to the headmistress to be introduced as her daughters. I found out in the meeting that my situation had been discussed in detail and had the approval of everybody involved. Of course I was dressed appropriately as a young female, a knee length skirt, plus a white blouse with a vest that matched the skirt. Hair in a ponytail with soft curly curls due to the efforts of a curling iron. Lipstick and mascara, applied by myself, my lessons in femininity already beginning.
Classes were mostly about appearance and manners. Two hour classes of ten students, with a qualified instructor. I had to learn two languages, plus be able to express myself both verbally and in writing. There was some basic math, but once you showed you had the basics down, that was exchanged for other feminine skills. Tricia was definitely in her element, excelling in everything she did. I was better that I been in high school, but at times it was a struggle.
About the fourth week of school Jennifer and I had a little conference after normal school hours. I was sure what it was about, but didn’t see how I could correct the situation. Up to this point I wore female clothes all the time, although my breasts were not emphasized any. I wore a bra, an A cup with small chicken filets inserted to give me a semblance of a bust. No dresses yet, but feminine tops and pants or shorts. My body hair had been removed at a salon in town and I did use lipstick and mascara often. My voice was neutral, not quite feminine but no overtly masculine overtones to it.
Jennifer knew my IQ and my ability to learn things if needed, so she was puzzled at my difficulty in my classes and behavior. We talked for quite a while, it seemed to always revert back to the underlying masculine body under the female disguise. Whatever the reason she would not settle for my performance as it is now. She has a couple of ideas and unless I can show significant improvement in the next few days I will be experiencing them first hand. No daughter of hers is going to be satisfied with just passing, top of the class is the only position she will accept from me. Considering that I am a male in a girl’s finishing school that is a pretty hefty goal.
Over the next few days I tried hard to make a difference, I did manage a better test score in English, but a day later failed a math test miserably. Jennifer picked me up at school, not even allowing me to walk to our home. Tricia was at some after hour’s school club, I think it was a chess club, but was not sure. I tried to talk to Jennifer, even called her Mom a couple of times to get her out of her mood. When we pulled up in front of the salon, I got the distinct impression I had let her down, and now corrective measures would be taken, whether I liked them or not.
I was hustled in to the salon, not dragged, but pushed back to a treatment room at the back of the salon. Several times I tried to drag my feet a little, the hand on my buttocks pushing me forward was firm and unyielding. I am sure if I had flat out stopped I would have received several swats immediately. Placed in a dentist like chair and my feet and wrists strapped to the chair, I was now apparently ready for my penance.
The tech came in, gave me a smile and slid down my panties and lifted my skirt. A cream was rubbed in all around my male member, and left for a while. While that was processing, my blouse was undone leaving my chest exposed. A huge machine that left me breathless was pushed to my side and two cups were glued to my chest, right above my nipples. The cups were good sized, the nipple at the end of the cup made the conclusion that these were for giving me breasts pretty obvious. It was a couple minutes later when my mind finally figured out what was going to happen.
I just laid there in the chair taking all of this in, breasts and my penis done away with seemed to be the purpose of this action. I wasn’t alarmed or fearful, for some reason this just seemed to make me more relaxed. I would no longer be impersonating a female, I would indeed be one, at least, body wise.
Story Incomplete At Present
© 2016 thru 2021 Fran Cesca Walker