This is my story of Jack becoming Jennifer

 

How Jack Became Jennifer

by Jennifer Bryant

 

Hi my name is Jack, I am a thirteen-year-old boy, born Jonathan Nathanial White, I like Jack better, and I am the youngest of four kids and the only boy in the house. My sisters Angela 18, Rebecca 16 and Amy 14 and my mom a very successful and highly paid criminal defense Attorney, Donna who I think is around 40, being a lawyer keeps her very busy for 16 hours a day and away from home several days or more each month,. I became very independent and self sufficient at an early age. I have no memory of my father, as he had died in a plane crash when I was just three years old, my mom never remarried or had many male companions; she involved herself only in her career or other woman friends that were also professional and single moms too. I am very close to my sisters as each of them looked out for me while I was growing up; being without a dad or any other male contact with the exception of a few teachers I've only known the female side of things. I am small for my age; in fact my sister Amy is my size or even a little taller. I am often the joke at school as being the runt of the litter, but I don't care I am easy going and just shrug it off. I am an "A" student and like school; this also causes many jabs from other classmates, but mostly the boys they call me an egghead and a sissy, I don't care for sports that the boys played, I felt they are much to rough, but I hang around my sisters when they play soccer or softball. I have enjoyed watching the girls play while growing up I often played with them and the other girls as they practiced. I knew how to play soccer as good as my sisters at the age of nine.

 

My mom has a twin sister, Denise that lives in the next town about twenty-five miles away; she was a nurse, and then became a doctor after she was divorced. She also has three daughters, Cynthia 20, Sara 15 and Michelle 13, born just two days after me. I always felt Michelle and I had a connection because being born almost the same time. We got along perfectly, growing up I remembered playing girl type games with Michelle. Aunt Denise and my mom would always spend holidays; vacations or just a weekend get-a-ways together whenever they could arrange their busy schedules. My cousin Cynthia is engaged to be married and all my sisters plus Sara & Michelle are in the bridle party, they are always going for gown fittings or planning for the wedding. I feel somewhat left out of the family as all the talk is about the wedding. It has been the only time that I really felt that way, everyone was getting older now and I still had very little male contact. All I here about on a daily basis is pantyhose, bras, dresses and high heeled shoes, proms, what to wear what not to wear, off the shoulder or bare shoulder, I hear it all at every meal we have together. My mom just looks at me, rolls her eyes, then smiles and tells me what an understanding son and brother I am.

 

One sunny Saturday afternoon I was watching my sister Amy play soccer. Suddenly she collided very hard with a member of the opposing team. I became very frightened as she lay there on the ground out cold, she did not move for several minutes. When the coaches finely got her aroused I could tell she was in a lot of pain, tears filled her eyes. One of the coaches called 911. Within minutes the EMT's arrived and started to work on her, they started an IV and talked on a phone to a local hospital describing her condition and steps they were taking to make her comfortable. It appeared that she has several broken bones and had a possible concussion. I was very scared and concerned for Amy. I told the EMT's that I was her brother and that I wanted to go to the hospital with them, but they wouldn't let me, said it was against the rules. I just followed on my bike; the hospital was not far from the High School. In the mean time the coach managed to get my mom on the phone and she said she would be at the hospital as soon as she could get there. It was really scary at the hospital, they took Amy to a room where I couldn't see her, and I became more frightened. Mom came in just minutes after we got there, but it seemed like hours. She asked me what had happened and I told her as much as I knew. It was just a few minutes later that a woman doctor came out to talk to my mom. Amy was headed up to surgery in just a few minutes. The doctor explained that Amy had suffered a severe fracture in her hip and it would take surgery to reset the broken bones. I panicked, but my mom remained cool and collected. We were able to see Amy before they took her upstairs to surgery. They had given her pain medication; she was much more comfortable than when I had seen her lying on the ground at the high school.

It was an hour or so later before the doctor came back and told mom what was done to Amy's hip and leg. As the x-rays had showed, she had several broken bones in the upper leg and hip from the collision, they had to place several pins and a cast which would remain on up to six months. She would have to remain in the hospital for as least a week with total bed rest, then only able to go home if placed in a hospital bed so as to keep the hip and leg from moving.

 

Amy was in tears as we got to her room, she was awake but very sleepy. "Oh mom", she cried, "What a mess I made of myself".

Mom said, "Don't feel bad, you're going to be okay and which is the only important thing anyway".

I just looked at Amy as she lay in the hospital bed looking so lost and broken. I had all I could do to say, "Hi Amy, does it hurt much?"

Amy just tried to smile and said to me "see you thought that the boys played rough, but look what happened to me".

"Yeah, you really crashed out there on the field" I said as I touched her hand. "You had me scared there for a few minutes sis."

Amy just smiled at me, but wanted me to hold her hand. Several minutes later Angie and Becky came in to Amy's room and now the whole family was together again. We all left a few minutes later as Amy was very tired and needed to rest.

 

Over the next several days I visited Amy every afternoon after school. On day three, she was in good sprits, as all her friends from the soccer team just arrived shortly before I got there. I knew all of them and they of course they knew me; after all I was at just about every practice and game. We lived in a small town and the girl's soccer team had only one girl more than was necessary to play in the state league. If they lost any one else they would have to forfeit the remaining seven games of the year and the team was headed to the state championships. Amy was there best scorer and was also good at defense. She would be missed and there hopes at the title were now dashed, but they still had a lot of spirit and didn't want Amy to get upset, she was already feeling guilty at letting the team down.

 

On day nine, mom and Aunt Denise made arrangements for Amy to be moved home, they had rented a hospital bed with all the equipment necessary to keep Amy's hip and leg immobile, for the next several months as required for proper and correct healing. Amy was bored already, she was an active young teenage girl that didn't like lying around, but she was grateful that I was there everyday after school to help her past the time. She would apologize to me all the time from keeping me from things that I wanted to do. I told her that I wanted to be with her and keep her company if she wanted. We played board games; computer games and we wore out my Xbox. We would watch TV and movies or just talked. I became even closer to Amy and we were all ready close anyway. Angie and Becky had job, boyfriends and lots more homework, so they did not have as much time as I did.

 

On day twelve the girls from the soccer team came again, but this time they were pretty sad. The girl that took over for Amy was leaving town in the next four days as her father had to leave the country for his job. This meant that the team was one player short of the requirements to compete in the league. With six games to go they would forfeit all those games and the entire season would be gone. Tears were abundant that sad day. They tried to recruit other girls but no one was interested or had the time. I just sat there and didn't say a word. I was as sad they were. Amy's new room was suddenly very quiet. Then they all turned to me. Vicky, the team captain, said, "wait just a minute, Jack knows all of us, he has practiced with us, and he knows all our moves and plays". Vicky stood and came over to Jack, she told him, "Jack, stand up"! I just looked at Vicky not having any idea was she was thinking. I stood and Vicky looked me over, up and down and all around. "You know I think we might just have a way to continue to play, if Jack is willing to help us out". Vicky said.

"How can I help? I can't play on a girl's soccer team". I said.

"Why not?" was Vicky's reply and the other girl's said the same thing, including my sister Amy.

"I am not a girl, for one". I said

'No one would know after we finish with you. You and your sister look almost like twins any way. You would be surprised if you let us try." Vicky said now with a strong conviction. Then all the girls began to plea with me now to say yes.

"How could we possibly fool coach Haverhill, she would know it was me a boy trying to be a girl replacement, how would you explain where I came from".

"The league is sponsored by the town not the school we can check the rules. We will come up with something, we'll just work in out, it the mean time Jack just say that you'll help us".

"Please!" all the girls said in unison. How could I refuse, I was stuck.

"Okay, I'll do it, if you can get Mrs. Haverhill to agree.

 

Next day was Saturday, Vicky told me to be at her house at nine o'clock that morning. Her mom would be working all day; the house would be ours for the day. I wasn't sure want to expect at all. I was nervous when I rang Vicky's doorbell, as the door opened I heard many voices coming from within. Five of the girls were there to help Vicky transform me to a member of the "Honeybees" soccer team. I had very light hair, nearly blond and I kept it long nearly to my shoulders, it always had a natural curl and was easy to take care of. I had little or no body hair, just a little fuzz on my legs. As the girls looked me over again I felt I was on display and was going to be sold to the highest bidder. Vicky took my hand and lead me to her room. She was the oldest of the girls at 15 almost 16 the other girls were from 13 to 14 like Amy and me. "This is going to be easier that I thought". Vicky said. Vicky pointed to the bed and shown me the uniform she had laid out for me. That was okay, but the rest of the garments had me concerned. A light pink bra and panty set were laid out next to the white pleated skirt and tank top that made up the soccer uniform that had "Honeybees" across the front at the bust line in yellow and black and a picture of a honeybee on the skirt. The knee-high socks were yellow with black trim with the same honeybee picture. Even though I had seen the uniform many times before the though of wearing it was now a scary feeling. Vicky said, "Go into the bathroom spread this cream all over your legs, let it sit for ten minutes then get in the shower to rinse off, this will remove any body hair. Put on the panties and robe, then come out and we'll help with the rest." I just stood and looked at the girls now speechless. I was becoming very scared and was having second thoughts about doing this whole thing. I said, "I really don't think this is going to work girls. I can't do this! This is nuts!"

"Oh Jack, come on you promised to help us out, think of your sister laid up in that bed helpless and feeling she let the team down, now don't you do it to us too." Vicky said.

All the girls pleaded with me now, begging me to help them out of there dilemma. Vicky took the pink panties, handed them to me and all the girls pushed me to the bathroom door and shoved me in, then closed the door saying I would be held captive until I at least got dressed all the way in the uniform. I was really stuck now; I didn't want to let the girls down. I thought of Amy and how hard she played and the pride she had for the entire team. I took off my clothes; standing naked I took the bottle of lotion, opened the cap and spread it all over my legs, up to my thighs. Looking at my watch I waited the ten minutes, my legs were tingling and felt very strange. I jumped into the shower, what little hair I had vanished as I stood under the warm spray. I had very little body hair to begin with and how it was gone. It felt really strange. I dried off, took the pink nylon panties, they were very soft and felt like nothing at all. When I slid them up my leg they stretched and hugged my body, what little manhood I had was pulled back and up and was very well hidden in the new undergarment. I was amazed at the feel and how it made me look in the long bathroom mirror. I put on the pink flowered silk robe; my heart was pounding as I opened the door. Vicky took my hand and led me over to a table with lots of lights around a mirror, with many bottles and tubes of make-up and all kinds of stuff I have seen my sisters and mom use. Vicky started to work on my long hair; another girl looked at my face, while another looked at my nails. They all started talking at once. They were going to do a complete make over of me to make me look like a girl. Vicky brushed my hair, Claire worked on one hand while Connie worked on the other and Chris worked on my face, I was surrounded by cute teenage girls all fussing over me like I was special. The feeling was very confusing but I was actually enjoying myself. At times I had no idea what they were doing to me as they were all talking at the same time, I couldn't see much as they had blocked my view of the mirror. On hour later they seem to be done but would not let me look. I was led over to the bed again and they took off the rope, I was slightly embarrassed as I stood there in my pink panties and nothing else. Vicky and the rest of the girls were so great they made on comments about my body they just kept saying that this is working out so great. Vicky slid the lacy pink bra up my arms and fastened it in the back, if felt very strange indeed as she made sure the straps were straight, the other Claire took some nylon stocking and placed them in the cups of the bra to give me boobs. That was really a strange feeling. Then came the skirt, I knew it was my sisters, because I saw her name inside the waist band, it fit snug but not tight and zipped up on the side. The top was a tank style with 1-½ inch wide shoulder straps that covered the bra straps but came just to the top of the bra in front. The feeling I was getting was overwhelming to say the least. The final touch was the knee-high socks and soccer shoes with rubber cleats. I was done, all I could hear were sounds of joy, as all the girls just said one word, "Amassing!" Vicky and Claire took my hand and led me to the long mirror on the wall. I was looking at my self in astonishment and disbelieve, I was transformed into a pretty teenage girl. I had long curly light brown hair, with just a little bang, my lips were pink and my eyes were aglow with pink shallow and black mascara. My nails were pink, I looked at the other girls and we all matched. I looked like my sister Amy, it was totally amazing I just stood there and barley moved. "Jack you look absolutely stunning, but we have to have a girls name for you now." Vicky said.

"Janet!" Claire yelled.

"Jan!" Cried Chris.

"Julie!" Was Connie's choice?

"I know we'll let Amy decide lets take Jack over there and show how remarkable he looks." Vicky said.

"I can't go out dressed like this; I'm a boy every one will stare at me!" Jack said.

"Are you kidding, no one will know you are a boy Jack, even your own mother won't know or your other sisters for that matter."

"Vicky I'm just not sure I can do this, I am scared." Jack stuttered.

"Jack if someone recognizes you on the street, I will date you steady for a year." Vicky said.

Wow I thought to myself, she must be pretty sure. Vicky is the most popular girl at the high school. She is pretty, smart and has a very outgoing and friendly personally. She is not stuck on herself like most 15 year old teenage girls. "Okay!" Jack surrendered.

They replaced the soccer shoes with regular sneakers, which were also Amy's new ones, and anyone who looked at them would know they belonged to a girl.

 

It was only a half-mile walk to home for me, but it seemed like miles. The feeling I got walking with the five other girls while dressed in Amy's soccer outfit and underwear was more than he could comprehend. I thought I was living a dream and that I was going to wake up at any minute.

 

The girls entered Amy's room; she was sitting up reading the latest copy of teen magazine. They had me hidden behind them so Amy couldn't see me. "Jack didn't do it did he? He skipped out I bet, where is he?"

"We don't know, we haven't seen Jack today, but we got lucky and found a girl who can play soccer and is willing to join our team, her name is Janet. Here she is!" Vicky said.

I stepped forward not by choice but by being pulled by the other girls. Amy took one look at me and said, "Jack is that really you, my God you look unbelievable, WOW!"

"Yeah, sis it's me."

Amy held her hand to her mouth and started to cry real tears, "Oh, Jack you look so good I can hardly believe it's you. If I didn't know I would swear I couldn't tell."

"Then why have you got tears in your eyes?"

"Because, dressing like that takes a very special brother, to do what you're doing for me and my team."

"Thanks sis." Amy and I hugged each other.

Vicky said, "Jack needs a new name and we thought we let you pick it out Amy, since he is going to be your new sister."

Amy thought for a moment, looking at her brave brother standing there in her uniform with boobs and all, and said, "This is hard, but I have always like the name Jennifer, so I think that's what I would pick."

"Okay, then Jennifer it is." Vicky said.

All the girls looked over at Jack and in unison said, "Hi Jennifer"

They were all in such good spirits and each girl gave Jack a big hug and said her new name Jennifer. Now all they had to do was convince Coach Haverhill to let Jennifer join the team and make sure that she believed that Jennifer was really a girl and not Jack, Amy's brother as the resemblance was very present.

 

I relaxed as the girls continued to talk, I was becoming use to wearing the short skirt, and the underwear kept reminding me that I was indeed dressed as a girl, the bra and boobs filed out the top of my uniform very nicely. He just didn't have the fluid bounce the other girls had with real boobs.

 

It was one o'clock when Donna decided to go check on Amy. She left her home office on the second floor; on the stairs leading to Amy's first floor room she heard that Amy had company. She knew it was the girls from her team visiting again; they were all such good friends. Donna smiled as she entered the room; she knew each and every one of them, most since they were babies. Donna did not recognize one girl in the group. "Hi girls, I see we have a new girl amongst us, and she is dressed in your soccer uniform, is she Amy's replacement?"

"Hi, mom, yeah, this is Jennifer my sub." Amy said.

"Yeah Mrs. White we are very lucky to have found Jennifer to take over for Amy." Vicky said.

"Well I am happy for all of you. Hi Jennifer welcome to the 'Honeybees'" Donna said looking directly at the new girl. "Have you lived in town long I don't think I have seen you around to much, but you do have a familiar resemblance, but I just can't place right now?"

"Yeah Mrs. White, but Jennifer goes to private school and doesn't socialize much, she is really shy." Vicky said

"Well, she shouldn't be shy; she is very pretty and looks like she'll fit in as a team member very quickly." Donna said.

Nobody said anything, I just stood there looking at my mom, but she did not know that it was me, I didn't dare say anything, but I just smiled and looked at Vicky who just smiled back and winked at me.

"Are you girls hungry, I was just coming down to see if Amy wanted me to order a pizza or something."

"Yeah, that would be great mom, I would like that, and I am sure that will give us the opportunity to get to know Jennifer better too." Amy said.

Donna left the room to order the pizza, Vicky turned to Jack and said "See what did I tell you, even your own mother didn't know it was you, to her you are just a shy 13 year old teenage girl."

"Yeah you were right, I guess." I said.

"Don't worry Jack, I still think I will date you anyway for not only helping us, but I am beginning to get a big crush on you too for being such a great guy. None of the guys I know would ever agree to do this as you have and I personally am very crateful what you have gone this far." Vicky said with a big smile and then gave me a big hug.

Donna returned to the room about an hour later carrying two large pizza boxes and placed them on the table, a boy, the girls all knew as Brad followed with several 2 litter bottles of diet coke and a bucket of ice, paper cups and napkins. He wore a uniform with his name on a tag and a hat that said, Pizza Hut. He, of course, knew all of the girls too, except for me. He just smiled and nodded to all the girls. Donna said, "This is Jennifer the newest member of the Honeybees, she is subbing for Amy."

"Hi!" Brad said, as he looked right into Jacks eyes. "Were have your been hiding, you're very cute, just like the rest of the Honeybees?"

"Jennifer goes to private school out of town, but she is willing to help us out for the team as Amy's replacement." Vicky said.

"Well, I am for sure going to come to see her play then." Brad said.

Jack blushed as Brad winked at him while the other girls watched.

Brad tipped his hat as the girls and left followed by Donna so she could pay him and give him a big tip. The girls, including me watched them leave.

"My god, now Jack is flirting with other boys." Vicky said.

"Let's eat" Amy said coming to her brothers aid.

They all dug in to the pizza box, except me, as I was not sure want to do. I was afraid to eat in front of the girls. Then my mom came back into the room and said "Come on Jennifer eat, don't be shy, these girls will eat all of the pizza without you, they can be vicious." I went over and Vicky handed me a plate with a slice of pizza and a cup of diet coke. "Amy, do you know where your brother is, I haven't seen him since early this morning." Donna said.

"Why no mom, I don't know where Jack is." Amy said, having a very difficult time not laughing as well as all of the other girls. I just stood there, I knew for sure that mom was going to figure it all out now; I think I turned ten shades of red. Donna just looked at each girl still not sure what was going on. The talk turned to something else; several minutes latter, Angie and Becky stuck their head in the door and wanted to join in the pizza party. They were introduced to Jennifer (Me), not making any comments but nice to meet you, then just joined the party. After drinking so much coke I had to use the bathroom real bad. I couldn't just get up and go I was a stranger in my own house. Vicky looked over at me, and saw my discomfort, she said she needed to use the bathroom and asked if any one else did. I whispered very softly that I did. Vicky immediately took my hand and led me away from the group. We walked to the other side of the house I was somewhat relieved to be away for a while. Vicky said, "See Jennifer, I told you no one would know a thing, your mother and your sisters still don't know who you are." Vicky squeezed my hand, "Jack, you are a real special guy to help us and your sister like this and I want you to know that I really see you in a much different light right now. Thanks so much for doing this."

"It's been a time to remember that's for sure, it's been okay so far, but I am not on the field yet playing a game." I said.

 

It was late in the afternoon when Donna brought up the fact that Jack was still not around and couldn't understand where he could be. The girls started to laugh again harder this time and Donna suspected that they all knew something that she was not privy to. "Okay girls, you do know something about Jack that you're not telling me, what's going on?"

Amy was laughing so hard that she had tears in her eyes. "Mom, take a real close look at Jennifer and then you'll know." Amy just couldn't hold back any more and had to let their secret out. Mom got up and came over to me and stared at me for a while then said, "Oh my God, Jack that you under there. Okay what's going on? Why are you dressed that way?"

I was speechless and just looked at my mom then at Amy for some support, "I just wanted to help Amy and the girls out that's all."

Amy was quick with a response, "Mom, we don't have enough girls to play the rest of our games, we thought that Jack could pass for a replacement for the rest of the season. The rules say that all members must wear the same uniform and be of certain age, but nothing is said of gender. We have read the rules twice. Jack agreed to do this we didn't threaten him or anything."

"Jack, are you really okay with all of this?" Mom said.

"Yeah, I am now, I fooled everyone into thinking I am Jennifer. I really want to help the girls out mom."

"I can't believe what I am seeing here, you really had me fooled, that's for sure, I must say you look pretty good, no one could ever tell, hey not even your sisters knew that was you when they were here."

"Thanks mom," I said.

"Yeah well, I am not sure you can get away with this, but I will look over the rules and talk to Mrs. Haverhill about you Jack, I mean Jennifer, becoming a team member, I am sure that this is just an oversight and you won't be able to continue with this masquerade."

Thanks, mom" Amy said.

"Yeah thanks Mrs. White," the girls all said.

"I am not making any promises, but I will look into this first thing Monday."

 

The girls left but I stayed with Amy, Vicky told me that I could pick up my clothes tomorrow if I wanted too. I sat with Amy still dressed, she just looked at me, "Jack you look so good as a teenage girl, you really do."

"Yeah, it's been fun, I really like Vicky she is really so cool."

"You can go change up now if you want." Amy said.

"I know, I will in a minute, you think I'll be able to play? " Jack said.

"I am sure that mom will do her best to help us and it will be all legal." Amy said.

"I was relieved that mom was not upset and that she was willing to help too." I said.

 

On Sunday Mom read and re-read the rules and found no mention of gender in any of them. They just stated that each team member had to wear the exact same uniform, be between the ages of 12 and 16 and maintain at least a B- average. The league charter only required that each team member must be listed as to name, age, school attended, school uniform type if it was required, and grade average. The charter was very clear that each member must wear underwear, including bra or training bra as all times under there uniform. Must be compliant with the uniform rules at there school and have no discipline problems for the past school year. Each member of the team is required to shower in the high school after each practice and game, and maintain proper conduct and hygiene. The list of items was endless but not of it said anything about being a girl or boy, female or male. It was just assumed the players would be female because of the write-up, it was a bad legal assumption. They had to let Jack play at long as he wore the uniform, the real kicker was the school uniform compliance part and the warring of the bra. Jack may not like that part if they were insistent. Playing soccer dressed in a skirt uniform is one thing, but going to school everyday dressed in skirt and blouse is another. She would have to look at the school dress code from a legal standpoint too. Donna continued in her research about the dress code at the school and again it was very vague on the definition or boy/girl, male/female. In summary the code was written a very generic way. Students had the choice of blue or black pleated knee high skirts and white blouse or short or long pants, with white shirt. Correct undergarments to be worn at all times, no sneakers allowed except for phys.ed. She was going to talk to Mrs. Haverhill later that afternoon; she was also, on the board of education and an administrator at Jack's school.

 

On Wednesday night at a special meeting of the recreation department sports league the subject of Jack playing on the girls soccer team was going to be discussed and voted on. I had to appear in full uniform as a witness. All the girls would be there, except for Amy of course, and my mom was my support. The rules committee was trying to find away to not let Jack play, but the rules did not say anything about boys playing on a girl's team. The discussions went on for almost 2 hours. My mom was winning; they really had no choice but to let me play. Mrs. Harris then mentioned the school uniform requirement. She felt since I was going to school as a boy I shouldn't be allowed to play on the girl's soccer team regardless of the charter or rules. Then the talk started about the school and its requirements. Things were getting way out of hand now. The girls were worried that the whole year's efforts were going to go to waste and they would forfeit the remaining games. Mrs. Haverhill said she would bring the topic up at the board of education meeting scheduled for the next evening. Mrs. Haverhill turned to me a started asking me questions about my willingness to play the role of a girl in order to play soccer. The rules were very clear that they didn't exclude boys from playing, but it was clear that I did have to wear the complete uniform including the required underwear. I said I would do anything to help the girls play soccer. I said I was even willing to go to school dressed in a girl's uniform if I had to. Mrs. Haverhill smiled at me and thanked me for my honest answers and that this meeting was over, pending the school board meeting and its decision about me going to school in a girl's uniform.

 

By Friday, the decision was in, I would be playing in Saturday's game. On Monday morning I was required to attend my classes as Jennifer. I was assigned a separate shower and changing area and the use of a separate bathroom. The girls were overjoyed. I was in shock. What had I gotten myself into? Mom just smiled at me saying well now you really got yourself into a pickle.

 

To be continued ………

  

  

  

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