Cassandra; Filling In For Sis

I was woken by the damn phone ringing. I did my usual, just ignore it and it will quit, I even threw a pillow in its direction hoping to make it quit ringing. Still it continued on, now fully awake I decided to get up and answer it, planning on giving the person on the other end a piece of my mind. As I rolled out of bed I looked a the clock on my nightstand, the small hand on the six and the big hand on the twelve. Gawd six o’clock in the morning, a Sunday morning to boot.

I picked up my cell phone and opened it almost yelling what do you want. All the hostility left me as my Mom broke down in tears. She was babbling as she often does, I did pick up a few words though. I think she asked if I had heard from my sister, but couldn’t be positive since it was speculation on my part as to the words in between the ones I did manage to hear. I responded no, hoping that was what she was asking. It was fifteen minutes later when she calmed down enough to tell me that she had not showed up for her first day of school at the fancy finishing school that Mom had paid for her to attend.

During the last few months that is all Sis had wanted, to attend this school, thinking that it would give her an edge on her future. With my permission Mom even used part of my college fund to pay for the school. I was planning to join the service, still not sure what branch, the Air Force the most likely one of the group at the moment. Then after four years of service with them I would get my college paid for by the government.

I could tell from how Mom was acting I needed to make the trip home, to sort out what Sis had done and restore peace to the free world. I told Mom I would come home, give me three to four hours depending on traffic. I was still living in the dorm at the junior college I was attending, a couple of hundred miles from our home. After I hung up, I decided to go ahead and pack, one less thing to do later after I enlisted. I had just completed the spring term, but had two weeks left on the dorm rental. I threw everything together in whatever I could find and loaded it into my car. Cleaned up a little, hoping to get the cleaning deposit back, dropped off the keys at the administration office and headed home.

During the trip I wondered what my sister had done this time. She tended to be scatter brained, doing several things in life not expected by anybody. During her freshman year of high school, she slipped away and traveled four hundred miles with a couple of her friends to a spring break destination, the only way we heard where she was was when the police called telling us she was in jail for dancing nude in a beach bar.

Then there was the time she spent her allowance on drinks, ending up drunk and who knows what else at a friends house several hundred miles away. No one had any idea how she got there or where she was able to get the alcohol, since she was two years younger that the legal drinking age. Her allowance was hefty, almost three hundred dollars a month so that amounted to a lot of alcohol. It was a week before she could function again, her hangover one of the worst in the history of western civilization.

While in transit I called all the numbers I had for her, including all of her known friends. They had not seen her in several days, the only clue I got was she was hanging with a male in his early twenties, and they seemed to be romantically involved by the amount of groping and kissing going on. This info from one of her school chums, who incidentally was now enrolled in the same finishing school as Sis.

It took me over an hour after getting home to debrief Mom and get her to bed with a sleeping pill to make sure she would relax for awhile. She had been up for over twenty hours worrying and trying to locate Sis. When she gets this way, sleep is about the only thing that restores the Mom we have been raised by. Since Sis has pulled this or similar in the past, it just made things worse for Mom, imagining the worse for her daughter.

I knew a couple of places that Sis often hung out at, so I decided to check them out while Mom hopefully recovers some. No luck on the first few places, nobody had seen her in several months. The last place I had a little more luck. The gal who ran the bar, had seen Sis there the night before, with her companion. She tried to get Sis away from him to warn her, but she was all but in his lap the whole time she was there.

I saw the lady swallow hard, knowing what she might say next would not be good. The lady told me he was a suspected recruiter for a brothel in the far east. More than several of his dates never seen again. He tended to date the more outgoing young women, they were usually an easy mark for him. The women were promised gifts, lots of money and travel all around the world. She gave me a couple of places he hung out at, maybe I could still find Sis before she got shipped out.

I was getting desperate now, making the trip to his hangouts in record time. I think I found him at the last place she had given me, but Sis was nowhere to be found. I asked the guy if he had seen her, showing him a picture of her I had on my phone. Sudden silence, then he took a phone call and soon thereafter left the bar. As I followed him out the door he was getting into a taxi and heading down the street.

I tried the police giving them as much info as I could, but I knew there was nothing they could do to help find my sister. Until she was missing for twenty-four hours there was nothing they could do anyway. I left the precinct station depressed and almost in tears. Now to face Mom and what do I tell her.

I tried a school chum of mine from high school, whose brother was a private investigator, a last minute desperate effort to still find her. I arranged to meet the P.I. in a few hours at the local restaurant in town. I was early but to my amazement he was already there. We had interacted a few times while I was visiting his younger brother so we knew each other. I explained everything to him, what I had found out and where I had found the guy and confronted him. He pulled his phone out, thumbing through some pictures stored on it, selecting one and showed it to me. It was the same guy, that I had confronted earlier.

Jake explained that another young female was also missing, and he was suspected in that girls disappearance too. I tried to hire him to track down my sister, he would pursue it for me, but at no charge. He was doing the same for the other girl’s family. He cautioned me about expecting a miracle, things like this take time, although he was going to the West Coast to try and intercept the latest shipment of the young ladies heading overseas.

I never did tell Mom everything, I don’t think she could handle the truth. I told her of my attempts to track her down, but until we hear something we pretty much had done all we could. It was four weeks later when I heard from the private investigator, He had made some contacts in Los Angles and heard of a shipment of young females being sent to China, the shipment never materialized, the girls escaped and our suspected male kidnapper was found badly beaten on one of the freighters in port. He has no idea if my sister was one of the girls, all he has found out is that the girls have totally disappeared, no messages to anyone and no one sure exactly how many girls were involved. His original case of the missing girl also left in hiatus.

He left some contact numbers if any of the girls show up, but other than that every lead ended when the shipment was aborted. He will let me know if anything turns up, but realistically don’t expect much if anything.

Mom and I had been discussing sis’s paid schooling at the ladies finishing school ever since she disappeared. We tried to get a refund on the money, but the original contract clearly stated there was no refunds at any time for any reason. Once they had your money that was it, take advantage of the school or loose the tuition monies. I could see Mom looking at me, she had some idea, but would not share it with me. Finally a week before I had planned to enlist she cornered me in the living room, laying out her crazy idea.

She had contacted the school. they would accept me as a student even though they were already into the term. Me being a male not that much of a problem. I would have to go through the same training as the other girls, but if I completed the year long course I would receive a certificate of completion and be able to use their job placement services. They were quite proud of their success in placing students, ninety-eight percent of their graduating students placed in jobs paying more than sixty thousand dollars a year.

I was against it immediately, but Mom had that wistful look about her. She missed her daughter, even though she was the source of countless hours of frustration. To keep from telling her no right at the start I told her I would go to the school and talk to them about any possibilities. I called and set up an appointment for the next day at ten in the morning. I really didn’t have any idea what I was going to say to them, we had already been informed they would not refund any monies paid for tuition, so that avenue was dead in the water. I was dead set against becoming a student there, having no desire to become a graduate of their school.

I worried about the meeting all night, what to say and if I was really considering going to the school in Sis’s place. Every time that thought entered my mind, I shuddered, still it lingered there, never going away completely.

I dressed nicely, then drove to the school. It was about an hour and a half from Mom’s place, that was the reason why Mom had paid for her a room there at the school. It was actually cheaper if you stayed at the school, I presume they thought you might be more focused without constant interference from real life. I made my way to the administration office and was soon greeted by the head mistress of the school. As soon as I entered I was appraised by her, a smile soon appearing on her face.

I mentioned why I was there briefly, then to my surprise she suggested that I spend the rest of the day as a student to learn exactly what goes on and about what was taught. I was doubtful, this is not what I had in mind when I showed up. She smiled. “Give it a try, then you will know what goes on here.” I nodded my head in acceptance, but still not sure why I had agreed to the day as a student.

Before we had left her office it was suggested that I leave any personal effects with her, my keys, wallet ID and credit cards. They were placed in an envelope and promptly put in her safe. I was kind of lost, not expecting any of this. It seemed logical since Ms. Davidson said some of the classes required a change of clothes, this way none of my valuables would be at risk. She reminded me that along with a room, my meals would be furnished and all clothing and makeup that I might require is included in the tuition. The word makeup should have clued me in, but my brain was not functioning well, if at all.

I kind of nodded in agreement and soon found myself being led down a hall to their nurse’s office. Before I would be able to enter a classroom I needed certain immunizations and a basic physical, something required of all students.

The nurse appeared and asked me to undress. I was not to sure about any of this anymore, but imagined a physical and some shots possibly necessary. After getting undressed I was helped up on a table face down and my hands were slipped in cuffs on the side of the table. The cuffs were tightened and she explained that the shots sometimes caused a muscle reaction and she didn’t want to get hurt. She gathered her things and soon I felt the first of fifteen shots to my butt. I did jerk some on a couple of the shots, so the cuffs probably a good idea. I was left there as she took my vital signs, then lowered the center part of the table and examined my male organ very thoroughly.

She prodded, squeezed and pushed my balls back up into my body, just leaving my penis itself hanging down. Something was hooked around my waist buckling behind me, with another piece being brought up between my legs. I was getting worried and I tried to free myself telling her to stop. When my mouth was open she used a bottle to aim a spray down my throat. That was it for talking, the nurse telling me that the spray freezes my vocal cords for a few days the resulting voice later would be higher and most feminine. I tried to scream, the only thing I felt was a coolness lower in my throat, but not a peep was heard no matter how hard I tried.

The piece she hooked behind me was a belt, a strap that was hanging down from the belt had been brought up between my legs, my penis inserted in a small tube and then the piece was connected back to the belt. I heard a click and realized I had been locked up in a chastity belt. As I was struggling again to get free, the nurse informed me that all students wore chastity belts 24/7, a requirement of the school. Once a month when you have your period you will come back here to have it removed, cleaned underneath and then replaced. All I heard was when I have my period, surely she can’t be serious. She double checked the tightness of the belt, and the strap going through my groin, using a finger to see if she could slide it under the edge of it. She was content with the fit, since her finger went nowhere.

I just laid back, let out several sighs and closed my eyes. My so called day of experiencing the school was turning into a total nightmare. Somehow the idea that I am now a full time student here, not just for observing, but I am officially replacing my sister entered my mind.

That did nothing for my fear that all of this was getting way out of control. I struggled but to no avail. I even tried to move my legs but having no support under the middle of my body kind of killed that action. then when the nurse tightened the strap across my lower legs right below the knees that stopped any thoughts of me getting loose. She forced my feet into a form that held my foot like I was standing on my toes, then two more shots one in each leg was administered. I could feel the tendons in my legs tightening, but was helpless to do anything about it.

Now that I had my shots and was properly outfitted in a chastity belt she released me and allowed me to dress again. Instead of my male clothes I was handed a sheath dress and a pair of panties. I debated putting them on, but standing there naked made me feel even more vulnerable. I looked around for my male clothes, but they had mysteriously disappeared. I hurried not wanting to spend any longer with her than absolutely necessary. As the dress slid down my body the head mistress appeared again, there to take me to my first class. The first attempts at walking caused me pain as I tried to put my foot flat. I was given a pair of high heels to wear. I stared at the heels and violently shook my head. I tried to scream no, but no sounds emerged. I felt helpless, frustrated and very alone. She did help me to get my feet into them, buckling the straps around my ankle securely.

Just like that I was locked in chastity belt, wearing a dress and strapped into some ridiculously high heel shoes. With no voice to complain with and all of my I.D. locked away in her safe I was totally screwed and scared to death.

I tried to complain about being put in the belt, not a single sound emanating from my mouth. I had to hurry to keep up with her, but with the way that the crotch strap was wedged between my legs made me walk funny, more of a sway to my walk even though I was doing everything I could to walk normally. The heels added to the swaying of my butt too as I tried to keep my balance in them. We walked right on into the class and I was shown to a desk near the front. She smiled at me and turned to go back to her office.

So here I am setting in the front of the class, as one of their students. I noticed there was no teetering as I entered the room, all of the girls focused on the teacher and what she was saying. It took me a few moments but I figured out the class was in deportment, how to stand sit and walk in a lady like manner.

I was called up front, but the teacher had to walk right next to my desk to get my attention. She took my hand and led me to the front of the classroom. I was shown the proper walk for a female, then had to duplicate the movements. The ruler was used to correct any mistakes, more than a few times I was swatted hard. Believe me I learned how to do a sexy walk very quickly.

For the rest of the class I had to walk around the perimeter of the classroom, practicing my walk. That is thirty-five minutes of circling the classroom. My feet were aching now, not used to the heels or the exaggerated walk they caused. As I was leaving the classroom I headed in the direction of the office instead of where she pointed. I made it a few steps then I felt my ear being grabbed and pulled toward my next class. Every few steps she would use the ruler to correct my destination. I was deposited in the next class, told where to sit and she left.

The other teacher was not in the classroom yet, so I got up and headed for the door. One of the girls stopped me, telling me to stay seated. Ms. Sherry will be waiting for you in the hall to disobey her, then you will be marched to the punishment room to spend the rest of the day. Take my word for it, it is not a place to be at anytime, especially your first day. I looked at her, she seemed to be genuinely concerned for me and decided to sit back down.

I went over the last hour in my mind, this school meant business. I have never seen students, especially young ladies so quiet and well behaved. I can’t say I approve of their methods, but I did learn to walk like a female in less than an hour. Now whether that was a skill I wanted to learn is another matter.

The class I was seated in was introductory makeup, each student taking turns sitting at several vanities at the front of the classroom. Of course, having never experienced wearing any makeup I was like a dolphin out of water. The teacher picked me to be singled out, again why not one of the other girls. Shit I am doing it now, including myself as one of the other girls now. I presume my appearance puts me safely in that category now.

She would apply the cosmetic on one side of my face and I had to duplicate it on the other. The class seemed to last forever, that supposed one hour class seemingly lasting all afternoon.

So now leaving the class I was looking quite feminine, my face fully made up, my eyebrows now much thinner and my lips quite plump and pouty. As soon as I made to the hall I headed in the direction of the offices, but was way laid by Ms. Davidson who pulled me into a vacant classroom. She appraised my looks, apparently satisfied that I was blending in well with the other students. She told me that my Mom had come by taking all of my clothes, ID and car back home with her. She left you a note and will see you on the next visiting days in three weeks. I sat down in one of the desks, now alone and without a means to leave.

Apparently this is what Mom wanted for me, I began to wonder how much of this was orchestrated by her. Since Sis had been missing for quite some time I wonder if she had changed her mind about attending this school, leaving me in the dubious position of a possible replacement for her. At least that seems to be what Mom had arranged for me. I can imagine after a few months that my female skills in perfecting my appearance will probably over shadow what little bit of masculinity might that have been there when I walked into that nurses office.

I realized I had been holding the note tightly in my right hand, so I retrieved it and read what she had to say.


I know this is not what you want, but for my sake please try and live with the situation. I am at my wit’s end the real Cassandra has tried my patience for far too long. With you there as her I can still hold on to the dream that she will amount to something in her life. I am aware that it is not your fault, you have been a real gem of a son, but I miss having a daughter, someone to share my life with. In a way you are the daughter I would love to have, acting responsible and with a purpose in your life. The only problem is you are not female. The headmistress has assured me that a year at the school and you will be that daughter. Please consider doing this for me, I know it is unfair but I have so little to be thankful for and this will mean the world to me.

Your loving Mother

I sat down in the empty classroom and cried, a first for me. The door was open to the hall and one of the girls saw me and came in to see what the matter was. When I opened my mouth to talk and nothing came out she realized I was new and my throat had been sprayed rendering me unable to say anything. I was hugged and she took me to her room, stopping and telling Ms. Davidson what she was doing. The head mistress saw the wadded note in my hand and guessed what had caused the tears. She told Nancy we will be rooming together anyway, so go ahead. I was led off, not knowing where we were going or who my friend was. I was so lost, Mom laying quite a guilt trip on me.

I was not a female, yet I am apparently enrolled in a girl’s finishing school for the next year. I did nothing but try and straighten out the mess my sister left, and look where it got me. I was dragged into a room and laid on one of the beds, while Nancy went to get me something to drink. I couldn’t tell her what had happened, no voice placing me in quite a predicament. Along with the drink she handed me a pad and a pen.

Ms. Davidson has said we are going to be roomies, so now is the time for us to get to know each other. I will go first since I think from what I see that you and I are a lot alike. Her name is Dana, a feminine version of her former male name of Dan. When she told me we were both born male, my mouth immediately was open and I was trying to talk, a feat not possible since the nurse used the spray on me. She pointed to the tablet and the pencil and I quickly expressed my amazement and confirmed that I was indeed a male like her. She explained why she was a student here, here parents frustrated at her behavior as a young male, deciding that a daughter would be much preferred. She fought them at first, but over time she has learned a lot and prefers the female side of things now.

She did most of the talking, while I answered her questions with my pad. After we had covered about us, she told me it was time for dinner, helping me to change into the official school uniform. The skirt was a light shade of pink, its hem only reaching mid-thigh. The blouse was ivory, very sheer showing off anything worn underneath. I looked at Dana her breasts quite prominent and obviously quite realistic. She saw my interest, telling me that tomorrow I will receive a pair just as nice along with losing all of my body hair. I opened my mouth in shock, but of course no words emerged. Dana told me to withhold judgment until I had a set. They are quite useful, and add much to the female appearance.

At dinner I picked at my food, all of the things that have been done to me weighing heavy on my mind. My plans for my

future now in ruins, and what lay ahead for me a big unknown.

Story Incomplete At Present

© 2016 thru 2021 Fran Cesca Walker

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