Contessa; Making The Wrong Impression

Gawd, I sure hope they get hold of Dad and not Mom. I was setting in a department store security office, after I was caught walking out of the store with a bra tucked inside of my sweatshirt. Jackie, my girlfriend was going to shoplift it, when I caught her near the same store entrance that I was apprehended at. I snatched it from her and slipped it inside of my sweat shirt to keep her from getting in trouble. As I was making my way into the mall two females approached me and grabbed my arms. I was brought back into the store and asked to accompany them to the security office, Jackie was well ahead of me, so she escaped being caught.

I have been seated here for over two hours, waiting for my parents to show. After I gave them my name, the one gal asked if I was Patricia Chamber’s son. I nodded my head, this can’t get any worse can it? Mom is a leading attorney in town, and known to almost everybody. She is not only an excellent attorney, but involved in every organization or social group in town. She handles all kinds of cases but specializes in divorce cases. She represents both females and males, and researches her cases thoroughly, digging deep into what her clients tell her. If it is not the truth, she drops them quickly, suggesting that they agree to any settlement rather than taking it to court.

I heard some commotion in the outer office, then in walks Mom and Jackie. I can’t look directly at Mom, getting into trouble after all the time she has spent making sure I avoided it. She walks right over to me, pulls me up from the chair and gives me a huge hug. Then turns her attention back to Jackie, who had been standing there red faced and staring at the floor.

“Well we seem to have some matters that needed handling here. My son attempting to steal a bra, rather than pay for it like a good customer would. Then we have his girlfriend that thought she could steal a bra so easily, again not lacking for any money to pay for such an item. Maybe we can work how to handle this without getting the police involved and Jackie’s parents. I doubt that Jackie’s father who is the head of the school board would be thrilled to find out his only daughter is a thief. Then we have my side of the story, to be called and notified that my son is a thief, trying to steal a bra is a little earth shattering.”

“I suggest that now might be a time to speak up, to admit your actions have been stupid and idiotic. Then tell me what you are going to do about it. Conner, I can’t hear you.”

I knew better than to try any silly excuse why I had taken the bra from Jackie, there was a cashier twenty feet from the entrance where I could have walked over and paid for the bra. Instead I shoved in under my sweatshirt and tried to walk out. It was stupid and idiotic, actually the dumbest thing I have done in my eighteen years here on Earth. I could see Mom waiting for an answer, so I swallowed hard, then suggested that I might be allowed to buy the item, then do whatever the store wanted to atone for my actions. I could work for them free of charge, or clean bathrooms, or whatever they wanted.

Mom spoke first, I have talked to the manager of the store, a friend of mine and have worked out a suitable activity for you and Jackie. I am sure you will not like it, but then again to make a suitable impression on you it would be better that you didn’t like it. Here are two copies of the agreements that you and Jackie will sign stating what you will do to make up for your attempts at shoplifting. I suggest that you sign them immediately, we still have quite a bit to do before the store closes. The agreements were placed in front of us along with two pens. I was starting to read mine, before Mom cleared her throat. Jackie had already signed and handed the agreement to the security lady. So I signed, knowing full well I would find out what it said sooner than I might have wished.

The agreements were placed in a file and locked in a file cabinet, told that if we didn’t honor the agreements we would be turned over to the authorities and fully prosecuted as shoplifters. The accompanying pictures taken from the security cameras were added to the file before it was locked up, proof positive that I indeed had tried to leave the store with the bra underneath my shirt. Mom grabbed Jackie while telling me to follow her. We exited the security office, then down a long hall and right out to the sales floor. A few minutes later we entered their ladies wear department.

Mom addressed Jackie while keeping an eye on me. “Find suitable underwear for Tessie here, all of it to be ultra-feminine and sexy. She needs everything from panties to bras to stockings. She will need a C cup in her bras, all the stockings ultra-denier, and nothing that would be considered normal for a female. She will accompany you and after your selection you will help her try them on to make sure they fit. She needs enough for at least three weeks, fresh underwear for every day.”

Then she looked at me, her stern look conveying to me that I had better cooperate. “Since you wanted that bra bad enough to steal it, I think I can handle your apparent desires quite comfortably. Conner does not exist anymore, only my cute daughter Contessa, Tessie to people close to her.” I started to protest, but her slap to the side of my face ended that right away. It was not hard, but what hurt the worse was her doing it. I knew I had crossed her, now I was back to the starting point in my relationship with her. I shed a tear, but Jackie pulled me away, after watching my mother she was quite motivated to do what she was asked to do about my new underwear.

Once we were clear of her, Jackie apologized to me, for trying to steal the bra and for getting me involved. I gave her a hug, telling her to do as she was told, I will somehow get through this. I was soon in a fitting room, trying on lingerie. Just the look of it was enough to get me hard, but Jackie pushed me to keep trying on things and soon it was just another piece of clothing to try on, but such wonderful pieces of clothing. Mom did check on us, on the last check she gathered all of my male clothes and disappeared. The few tears I had succeeded in holding back came in torrents, the full impact of what I had done now making itself known.

Jackie held me close and allowed me to shed the tears that had been bottled up in me. She also knew that my days dressed as a male were over with, at least for quite some time.

I feared I would lose Jackie too, we were a couple but a male/female couple. I doubt she would be interested in me now that I will be dressed as a female, a sexy female from the selection of lingerie that had been set aside for me. Mom returned a little later, empty handed except for a dress that she was carrying. Jackie helped me slip on the dress, then zipped me up. I looked in the mirror on the dressing room wall, shocked at what I saw. Jackie was releasing my ponytail, suddenly Tessie was front and center, Conner no longer around. Mom pulled me from the image in the mirror, and we carried all of my new lingerie to the cashiers.

They rang it all up, a whopping four thousand one hundred and fifty one dollars and sixty-five cents. She reached into her purse and pulled out my credit card, handed it to the cashier and the sale was rung through. I signed for the purchases and we left the store carrying all of my new purchases. We loaded everything into Mom’s trunk and I started to head to my car. Mom smiled and told me it had been towed away, to be placed in storage until I complete my agreement. I let out a groan, then quickly put a smile back on my face as Mom gave me a withering look.

Jackie was very quiet, lost in thought of what might still happen to her. Mom drove to Jackie’s house, told her to go in and pack a few clothes for two weeks, and any makeup and hair products she needed along with a toothbrush. Her father has already been told she would be staying at our house to take care of some matters that needed attending to. Jackie gave me a help me look, but I was not in any position to help, just surviving myself would be a monumental task. She was gone about forty minutes, with Mom spending a few minutes talking to her father on the front porch. I can only imagine what was discussed. Her father did look my way a couple of times, expecting to see Conner but seeing a female sitting there instead. Jackie did appear with her suitcase a little while later and we continued on to our destination.

When we pulled into a salon’s parking lot, another huge sigh was caught before it was expressed, I didn’t need to give Mother any more reasons to be upset with me. I had caused all of this to happen indirectly, given her plenty of reasons to find a different approach to handle the problem I created. It is apparent she had indeed found something quite unique to teach me a lesson. A lesson I hoped to survive. I was dragged into the salon and taken right back to a treatment room at the back. Introduced to my technician Bev and then told by my Mother that I better be on my best behavior. If she hears from Bev that I have been other than super cooperative what had been scheduled could always be made more permanent, a situation that she doesn’t think I would want to experience.

Mom stayed with me as what was going to be done to me was explained. The whole time my mouth was wide open in shock. Then I was asked to sign the permission slips, I hesitated only briefly, maybe somehow I would survive this, just think what I can tell my children someday about my adventures as a female. Well if I survive and two if I find someone to marry me after this little adventure.

Mom left me there and Bev started right in on me. I was undressed, but complimented on my choice of lingerie, that causing an instant reddening of the cheeks and face. Over the next few hours I was relieved of any hair below the top of my head, then breasts were glued to my chest, Bev telling me about their new adhesive that lasts for months without causing any damage to the skin it is used on. The breast forms were heavy, and instantly jiggly on my chest. While I was occupied with them my male apparatus was glued behind a very realistic vagina, my first look down there causing an instant intake of breath. He was gone, my friend for eighteen years now hidden away for who knows how long. I hoped that this was just for a month or two, maybe I could survive for that long but longer I really doubted I could cope.

Bev went back to work, there was more in store for me apparently, I had lost track of what had been told me to be done, I guess you could call it selective hearing. My hair was washed and conditioned, then set in curlers and a dryer placed over them. While under the dryer my toenails were manicured and painted a deep red, then she moved to my fingernails and they were handled the same way after extensions were glued to each nail. As I sat there contemplating all that had happened to me I knew that I would never even think about stealing anything again even if it was for a blood relative. I wondered what Jackie was having to do, alone with Mom for this long can’t be good. I was finally dry enough for her to finish my style, so that was handled and I was again allowed to dress in my sexy lingerie. Then the dress, and who shows up but Mom. Again I ended up paying for my beauty services, another large chunk of my savings now gone, and then we headed to the car.

Jackie was sitting in the back seat, and that was where I was led. I sat next to her as she had her mouth open in awe at my new looks and figure. I was red, having my girlfriend see me sitting there just a pretty as her. Neither one of us paying attention to where Mom was driving. When we finally came to our senses we were parked back at the mall right in front of the store I wished I had never seen before. The scene of my recent downfall.

We exited the car, Mom’s stern look getting us out of the car quickly. Into the store and then back to the ladies wear department. I was introduced to the manager of that department and then led to a larger dressing room. It held rack after rack of dresses, skirts and blouses. I was told to undress, then Jackie helped me into the first outfit, a very short skirt and a fancy camisole meant to be worn as a blouse. I was to walk the aisles of the store, both floors for fifteen minutes. Jackie handed me a sign with a short hand hold to carry, telling about the outfit, its prices and where it could be found. The bad part was the sign acknowledged the model as Connor Chambers. I looked at Jackie, then at Mom and then started on my walk of shame. Meanwhile Jackie was led off by the department manager to do her penance. The heels that I was given to wear were not too bad, but it was several minutes into my walk before I managed to not stumble or trip.

I had no watch, so I was guessing when the fifteen minutes was up. I had re-entered the ladies wear department to find Jackie on one of their display platforms in another one of the outfits from the dressing room. She had her sign too, stating her name and the facts about her outfit. One of her girlfriends had already found her, wanting to find out why Jackie was modeling here in the store. When her friend saw me that interest died, her mouth wide open when she saw how I was dressed. Her phone was out in a flash and several pictures were taken and I presume circulated throughout the student body where we attended school. Once the word spreads I am sure I will have more than just her to watch my modeling attempts. I am sure the store will benefit greatly with all the free publicity.

With different outfits this went on for three hours, unfortunately pictures were taken of me in each outfit, to be used in the store advertising. At the time I had no idea how intrusive that advertising would be. When Jackie and I were led to Mom’s car, we were pooped both physically and mentally. In a way Jackie was able to survive better than me, since all her friends just thought she had got a job at the store modeling. Since I was a male, the job excuse would not be as believable.

At home things had changed just as drastically. My room was converted to a young girl’s dream, canopy bed and vanity, along with several mirrors placed around so that almost anywhere I looked I saw the female me. Apparently Dad had been busy as Mom handled me and Jackie. Once the shock of my new bedroom wore off a little all of my new clothes had to be hung up and put in drawers. That seemed to take forever, Jackie did help a little, after she hung her few things in the small closet in the room. I was told to take a bubble bath, then dress in my nightie. Jackie followed me and after she had put on her nightie we were called to the kitchen.

Dad on one side of the table and Mom on the other. There were pictures of us modeling at the store, plus copies of the agreements we had signed spread out on the table. I did get a hug from Dad, then he pushed me down in my seat. Mom as usual was the spokesperson, going over how it will be for the near future.

Since tomorrow is a school day both of you will be attending, Contessa the student now. I let out a low groan, but quickly put a smile back on my face after the look I received from Mom. Jackie was told it was her job to stick with me, helping me stay safe from the bullies at school. Since you were involved in this from the start it is the least you can do. I was told that my classes had been changed, now all of them to be female related, except for the basic math, history and English. That would include a class in Home Economics, Female Sexuality and of course P.E. with the girls.

One of them would pick us up after school and deliver us to the store, where we would spend the evening modeling clothes. Three one hour periods were set aside for us to do our homework, then one of them will pick us up when the store closes. That is Monday thru Friday with Wednesday off. Wednesday would be set aside for home work that required research or more time to put it together. Your grades will be looked at regularly, we both expect straight A’s. If that is not achieved you can figure you will be modeling for a lot longer than you have in mind. This is open ended, how you act, your grades and the reports from the store will determine how long you are doing this.

I might remind you that Contessa is my daughter now, failure to be a model of poise, deportment, beauty and honesty can make you my permanent daughter. Your car is to be kept in storage until you live up to your agreements, if after six months you are still Contessa, it will be sold. Getting to school will be on the school bus, plenty good enough for two young high school girls.

Now we come to dating. Any dates will have to be approved my us in advance and they will have to be double dates. Your young males will have to show up here to be approved and you have an eleven P.M. curfew. That goes for you too Jackie, your father leaving us to keep watch of you since your stunt. He still loves you, but you have greatly disappointed him.

You will sleep in the same bed, since you think you are a couple, with Contessa now having the same parts as you we do not have to worry about any fooling around. She asked if there were any questions, since both of us were in shock we had none. We both got huge hugs from both Mom and Dad then we headed to my bedroom, pardon, our bedroom.

When we arrived we sat on the side of the bed, then embraced each other. There were several tears, the impact of everything finally catching up with us. We used the toilet, then cuddled in bed, holding each other did help a lot. There were no words spoken, but our minds were busy trying to process everything we were told. It would have been so much easier for me to just pay for the bra, but no I had to try and sneak out with it. Well I got a lot more than I expected, now if I can just live through it.

The next morning arrived, the alarm waking us from our sleep. I won’t say it was a restful sleep, there were too many things yet to figure out and try and adjust to. Mom showed up telling Jackie to pick an outfit for me, while I was to take a shower, keeping my new hairdo dry. I complied, it was an experience in itself, my first shower as a female. Lots of different things to wash, several of those items I had no prior experience with.

When I dried myself off and made my way to the bedroom, I saw the clothes laid out for me. Whether these were solely Jackie’s selections or she had help, I would obviously be the center of attention today at school. I got dressed, still struggling with the bra and stockings, but finally got the selected items on. I couldn’t think of a single girl at school that wore dresses or stockings, so I presume I will be starting a trend. I just hope I live long enough to see if it catches on.

At least, I won’t be the only one in this attire, Jackie after finishing her shower donning an identical outfit. She offered to help me with my makeup, but I told her I wasn’t wearing any makeup to school. Who was standing behind me listening to my statement, yep you guessed that one correctly, dear old Mom. Not only did I wear makeup, but I got a liberal amount of every product on the vanity, including false eyelashes. One look in the mirror confirmed that I will be the girlest female at school, sure to standout in any crowd.

As we waited for the school bus to come, I almost threw up. My nerves were on edge, I was sweating and my stomach was doing flip flops. The bus finally made it, then the hard part. I climbed the steps to the bus, knowing that every set of eyes was glued to my new look. I feared a lot of kidding, but instead all I got was lots of greetings. Hi Tessa was the common greeting, with a few of the girls getting up and giving me a hug. My mouth was open in astonishment, why is this happening?

I actually pinched myself to make sure this was not some weird dream. I felt it, in fact I have to learn to not pinch myself, it hurt like hell. As I got off the bus at school the weirdness continued. Lots of greetings from the females, and every single male eyes glued to my feminine figure. No wise cracks, no attempts at bullying me, just lots of stares and attention in my direction. Most everybody knew my name, that is the Tessa name, and I was greeted favorably every where I went. I checked in at the office, according to Mom I had to pick up my new schedule, since she had arranged for more classes pertinent for a young eager female.

Off to my first class, female sexuality. That was eye opening for sure, a lot of things I never thought of were introduced into my mind. As I was heading to my next class I found out why everyone was treating me as Tessie. One of the girls who had seen Jackie modeling managed to find out why I was doing the same. Jackie told her a few things, the girl made several posts to her Facebook account and it went viral. Most of the females at school admired me for what I had done to save Jackie from even worst trouble. The few guys that tried to ridicule me were soon facing the ire of their girlfriends and any attempt to bully me died right there.

Girl’s P.E. was also eye opening, I had thought I might be allowed to take a shower afterward or in private, but since I had the same equipment as the other girls I was told to shower with them. The girls crowded around me wanting to see my assets closely, until the teacher told them to get their showers, Tessie is just another female. They went to get their showers, but I had a lot of eyes focused on my curves, I guess the fascination of a male now looking exactly like them body wise was the attraction.

I almost enjoyed the Home Ec. class, we were learning to cook and I quickly got immersed in learning all I could. The rest of the day passed without incident, by early afternoon I was getting accustomed to my new female role, interacting with the girls and giggling just like I was one of them.

Jackie and I had no classes together till the last class. She was quiet as she watched me interact with the others, then when the class was over she grabbed my arm and pulled me closer and kissed me deeply. “Don’t get any ideas, you belong to me and I will not have you flirting with any of the others, either male or female.” I tried to pout a little, but apparently that action will require a lot of practice before it will work for me.

That discussion ended as Mom pulled up in her Beamer to take us to the store. She also was watching how I behaved, a smirk followed with a huge smile plastered on her face. Jackie and her exchanged a few eyebrow maneuvers, but I dismissed it as just the two of them thinking of something different. We were taken into the store and Mom exchanged a few words with her friend as Jackie and I got changed to do our modeling.

Jackie was to be the model on the dais, only getting off to change outfits. While I was the one to walk through the store with my little sign dressed in some of the latest female fashions. I was recognized often, some of our school classmates stopping and talking to me. Then on one of my walk throughs. Chad took my arm and walked with me. Chad was the school jock, participating in most of the school sports and starring in a lot of them. I looked up at him, since he was a least six inches taller than me, and tried to free my arm. He smiled at me. Can’t I escort you around the store, it will do me good to be seen with such a pretty female. I was floored, saying nothing in return since my mind had turned to gush.

As we walked past where Jackie was perched on her dais, I got a look, then daggers as she saw who I was with. Chad figured out what the problem was and let go of my arm and stepped up on the dais and took Jackie’s arm in his. She got a hug from him, now I was jealous. I shot Jackie a look and we both busted out in a giggling fit. Chad soon joined in, I saw him in a different light now, not just a macho male but someone who cared and tried to show some of that caring attitude with others.

Some of the clothes I ended up modeling that evening were a little risque. A lot more of my body was exposed than I was comfortable with. The evening ended with me in a bikini, the only saving factor was the cover-up that I wore over the top of it. I was sure that the red in my face and neck didn’t lend itself to show off the bikini very well. I did get Jackie’s attention though, since it was the last item worn I wore it home. We both received outfits every day for our efforts, Jackie more appreciative of free female clothes than me. Already my closet had several changes of female clothing at the end. If this goes on for very long I am sure Mom will do away with some of my male clothes to make room for the female ones.

She has softened up a little, but I still get the hard looks and requirements for me to be feminine at all times. In the last day or two I have got a hug and kiss on the forehead, maybe in time I will be allowed to resume my male life. The deciding factor is when that may happen, are we talking about months or years? I was hoping for the months but feared the years was more likely.

There were no changes in the upcoming weeks the same thing everyday. On the first Wednesday, Mom revealed that she had approached the school and got an appraisal of what our grades would be come report card time. Jackie had managed a B in most of her classes, her Algebra class a C at the present. I was not so fortunate, C’s in all my classes and one D in English. Mom laid it all out, plain and simple. If that is the grades come report card time we will be working at the store for six more months and I will have all of my male clothes thrown away. If it continues to the end of the year, we will be taken out of school and home schooled, then found jobs as some type of clerical help for jobs, since it will be apparent that might be all we can handle in life.

Mom suggested a beauty salon appointment for both of us, since there is a good possibility we might end up as a dumb blonde types, a dye job to the blonde hair color and some enhancements to our breasts would be a wise and pertinent investment. I was also told that most of my money in my savings had been used for my clothes and beauty services, so a paying job in the near future would be advantageous. College for me was no longer an option, graduate high school and find a job my only path in life.

After she left Jackie and I cried together, but did resume our homework with a lot more enthusiasm. I thought Mom might be bluffing, but after the slap to the face I was no longer sure of her intentions or her love for me. I hoped she still loved me, but now that was a large question mark.

She did make the appointment, our now very light blonde hair causing quite a change in our appearance. Jackie looked much better as a blonde than me, but all of our girlfriends liked the color change, a few even envious. The breasts were another matter. Jackie had a hollow breast slid up over her breasts, giving her another cup addition in size. For me it was much different. My breast forms were removed and clear cups were glued over where my breast should be. Hoses were hooked up to a machine and the pump started pulling extraneous tissue into the forms. I shed a few tears, even I could see where the resulting breasts would be with me for quite some time if not forever.

I spent a lot of time thinking of events and what has been done to me. I actually had a revelation, all of these things were accepted by me with very little arguing or protest. Not something a male would have allowed to happen, even if his parents were behind it. So now there might be something else at work here.

Our grades did improve Jackie now straight A’s except for Algebra which she got an A minus in. I also improved a lot

but still two B’s were on my report card. I was so depressed when I had to hand my report card to my Mother. Jackie had already shown hers and received well done from both of my parents. When Mom looked at mine she reached out and pulled me closer to her. My manicured hand held tightly in hers.

“Did you try your hardest in these classes?” I nodded my head in the affirmative, then quickly stared at the floor again. Her hand under my chin raising it so I had to look into her eyes. She went over my grades class by class, mentioning that my female orientated classes were all A pluses. Then she brought up my two B’s, one in Organic chemistry and one in Calculus. “Well maybe I should have changed you out of those two classes when I signed you up for the female classes. I was hoping for a scientist or maybe a physicist, but will be more than happy with a cute daughter that can look so good in a dress.”

I looked at her, my face cocked to the side trying to figure out what she just said. I got a giggle from her, not a big one but still a giggle. Finally she sat both of us down and revealed a few things we were not aware of.

“There was never an agreement with the store, I paid for the item and the store made more than enough profit off of my purchases for you to satisfy them. You were compensated for your work there, the money put in a bank account for you. After I saw how you were adapting to the role the hair color change, the more permanent breasts, and several other treatments were added to see how far you would let me go in changing your gender.”

“You never hesitated, and have been happier that I have seen you in years. I let Jackie in on this after the first month, she was thrilled in getting a girlfriend in the deal and has advised me of some of the discussions that you two have had. I never did use your college money for your clothing and beauty services, those I paid for myself. The reports from your teachers are the most telling though. All of them so impressed in your behavior, your caring for others and your interaction with other students. I understand you now belong to quite a few school clubs and help the junior class with charitable fund drives and planning for upcoming events. So I will accept my cute daughter as she is, the B’s will be over looked but not forgotten.”

“The store would like you two to continue working there, but that is your choice. Now I have a need for a great big hug from my daughter if you can see your way to do so.”

I squealed, launched myself in her direction and was kissing her and hugging her tightly. I leaned in placing my head on her shoulder and silently shed some tears, my Mom still loves me. Even though I had made the wrong impression initially, I can now see a bright future for me, a future as a female and the love of a family and a special girlfriend.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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