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The Challenge

Author: 

  • TylerD

Audience Rating: 

  • Restricted Audience (r)

Taxonomy upgrade extras: 

  • Transgender
  • Fiction
  • Crossdressing
  • Posted by author(s)

The Challenge

by TylerD

The Challenge

Author: 

  • New Author
  • TylerD

Audience Rating: 

  • Mature Subjects (pg15)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

A man and his two sons have been selected to participate in a reality show. They think that they will take part in an "Amazon Adventure Challenge." In reality, they will transform into three black women and compete against other teams for the next six months. The guys will participate in girly challenges, dance classes, and learn how to be women. For the finale, all the contestants enter a beauty pagent and America votes for the winning family!
 
 

The Challenge

By Tyler


 
The letter had finally arrived in the mail from NBC studios. Our family had been selected to participate on the "Amazon Adventure Challenge" reality show. My dad Joe and my brother Kevin were very excited when they opened the letter. In one week we would be flown to an affiliate studio in Boston where we would begin preparations for our participation on the show. It was going to be exciting.

One week later, we were in the lobby of the studio with six other groups of fathers and sons. All of the Dads were between the ages of about 28 and 45 and the sons were anywhere from 12 to 18 years old. The secretary told us all to sit down and get comfortable and get our coffee. After about 15 minutes of waiting, a small man who looked like Michael J. Fox came out of the black door and introduced himself.

"Hi, my name is Matt," he said. "If all of you would please follow me into the auditorium.

All of us(18 guys total) formed up into a single file line and walked into the room. We took our seats in Movie-Theater style chairs.

Matt walked up on stage and stood at the podium. He began by saying, "I want to thank all of you guys for coming here to take part in our challenge. It was designed to test even the strongest of men and your famlies will go through an experience of a lifetime that you will never forget. Before I start, I want to introduce some people to you."

Then, 7 blindingly beautiful women walked out on to the stage from the left exit. Two were Japanese women, three were black women, with one brunette and one blonde white woman each. All were immacualtely made up and all were wearing tight, form fitting, desinger outfits with heels and stockings/tights. All the guys were asking to themselves what these gorgeous models had to do with any "adventure challenge."

"CBS aired 'He's a Lady', five years ago," said Matt. "However, that show was a joke. We misled you when we told you all that you would be taking part in a survival contest. Instead, the point of this show is to live as fully functional women for a period of six months. We will make every one of you as gorgeous as the women standing up here."

18 jaws dropped. You could hear a pin drop.

"However," Matt continued, "We have another twist. Not only will you boys all be made over into beautiful girls, but you will be changing race as well. Yes, every one of you will see what it is like to live life as a black woman. After six months, America will vote for the winner, and that family will receive a grand prize of 2 million dollars."

This was totally unbelieveable, I thought to myself. My dad was in absolute shock; he had a blank experession on his face. My 13 year old brother, I think, was a little too young to take it all in. But I was a 15 year old boy who played three sports. What was I ever going to do. I couldn't go to a school and wear tights and barettes and dance with boys and be girly. This was going to be so embarassing and I would be humiliated for the rest of my life when I went back to being a man. I couldn't stand the thought of my dad putting on those flamboyant outfits I usually see black women wear.

A couple times when I was 10, my mom dressed me in my older sister's ballet outfits but that had been a one time thing. I thought about how good those white tights had felt. My mom and sister were going to be all by themselves but Matt assured us that they would get an allowance while us guys were otherwise occupied. Matt continued to talk about how we would be taking ballet, charm classes, going to a prom, and so forth, but it was all a blur.

After a minute or to, my attention came back to Matt who was still speaking. "These 7 women up here will be your coaches. Relax, they are actual women, unlike you girly guys."

The cameras stopped rolling and we were filed out into a large back-room type area. One of the ladies who was on stage, one of the black ladies came up to us. She looked like Gabrielle Union, and she towered over my dad by 3 inches. She was wearing a white skirt suit with white tights and black heels.

She shook my dad's hand and said in a thick urban drawl, "Hi, my name is Fiona."

"I'm Joe," my dad replied, "These are my sons Kevin and Mike.

"Its nice to meet you girls," she said. "You girls have nothing to worry about. Everything will be all right. After we transform you into black girls, the four of us will all be moving to a small town in New Hampshire called Dresden where we will live for the next six months. Basically, I will be your coach and I will help you with all of your female tasks. I will help you guys do your hair and makeup and select outfits to wear every day. I will show you guys how to use feminine hygiene products and stay beautiful. I'll help you guys learn to dance like women and give you extra coaching with your ballet. At the end of the six months, there will be a pagent where you all will model some swimwear and a gown and perform some dance routines."

"She continued, you boys will attend school and after school you'll be involved in cheerleading, ballet, jazz dance, and future homemakers of America. Dad, you'll be getting a job at Hooters and you'll be my "wife". I'll expect you treat me as you would treat your husband, with the execption of sex, of course."

"Oh," she said, "I almost forgot. Joe, your name is now Monique. Mike, you are now Brandy, and Kevin, you are now Kendra. I will only refer to you by those names from now on."

So we were led back to an absolutely cavernous backstage area with all kinds of "stations". I could tell instantly that it was for makeup. First, we were led back to a bathroom where the three of us took all of our clothes off and put or guy clothes into boxes. We put on pink bathrobes and walked out wearing only the robes and some pink shower shoes. All 18 guys eventually filed out and every group was sent to separate stations with their coaches to begin their transformation work. Cameras were on hand to film the process intensively and conduct interviews during our breaks in the middle of our transformation.

My dad said to us, "I want to tell you guys that no matter what happens, we are still men. We may be girls on the outside, but we are men underneath."

"Its fine with me dad," Kendra said, "I want to get that money. I don't mind being on TV and being famous. Girls like androgynous guys anyway."

"I want to back out," said Dad, "but with the economy as bad as it is, if we win, all of us will be set for life. Besides, my company was downsizing, so I could be laid off and then we'd all be homeless. Also, we'll be able to pay for your college."

"I don't see what choice we have," I chipped in, "If we back out, the media will call us cowards for not participating."

We spent the next hour in a shower stall shaving all the hair off of our bodies except for our heads.

The three of us headed to the first station, which was a tanning booth. A Pakistani girl was responsible for giving us a nice ebony tan. She had each of us take our turns and go in with our robes off. Dad went in first and was sprayed for 10 minutes. He came out and was the color of a Hershey bar. He would have looked like a black man except for he still had his white-guy hair cut, so really he looked like a Sri Lanken. I went in next and I was sprayed the same rich color. I watched my white skin slowly turn dark and I wondered to myself how long that this effect would last. It was then I realized how fortunate I had been so far in life to be a white guy. Being a little black girl was going to be a challenge. I would have to listen to rap music and date black guys and wear thong underwear. I was kind of looking forward to ballet class.

Kendra then went in, and after she came out, we all looked totally different then we had that morning. The Pakistani girl explained to us that the spray-on pigment would last for 9 months before fading, so we would have to slowly adjust back to being our old selves.

We were led to the second station. A guy dressed in gothic clothes had boxes of some strange items. He opened up one of the boxes and there were some absloutely enormous brown blobs. It was clear at once what they were for. He told my dad to open up his robe and he took two breast forms in my dad's shade the size of cantelopes and glued them to his chest. Dad had absolutely enormous boobs. But I was petrified when the man grabbed two more forms that were only slightly smaller and he glued them to my chest. I could no longer see my feet, and these things were heavy and cold. The color of the breasts matched my skin perfectly. I knew then that I would have to wear big bras and it was going to be a huge challenge.

My little brother had a medium-sized pair of breasts glued to his chest. The guy told him that after about 3 months they might give him bigger ones, since Kendra might mature a little bit. He then handed us each a pair of shaper panties and he told us that these would "hold us in" Again, they were the same shade as our skin and we pulled them on. When we all had ours on, there was no trace of our manhood and we all were built like women from the neck down.
 
 

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We were led over to a salon area with three chairs. We were told to each take a seat in the high-chairs. Each of us were suddenly attended to by two makeup artists who came over to work on us. The two girls first trimmed my thick eyebrows down to thin wisps. They applied a beard cover to hide my peach fuzz and put some foundation on me. I was given mascara, rouge, the works. As I looked over, my father and brother were getting prettier and prettier.

Fiona said to us as they were making over our faces to look like pretty black girls just like her, "Later, I'll teach you guys the specifics of makeup for black women. But now, just sit back and enjoy this unique time in your lives. You boys are going to have some style and get your groove on. We'll all do some booty calls!"

The girls probably used about 20 strange products on my face and lashes. For the final touch, they put some purple lipstick on my lips. I opened my eyes and there was a hot black girl with short boy-hair staring at me.

However, soon, the salon girls came back with hair-extensions and weaves. They clipped a long mahogany fall into my short hair and soon I had long hair.and all my malehood was starting to vanish. My brother soon had long black hair and they were beginning to pull it into a mass of tight, short curls. In all of our hair, Fiona sprayed some sort of substance and explained it to us, "White people and black people have different types of hair. What I am spraying here will give your hair that fuzzy, nappy quality that all black people have."

My dad wasn't getting long hair. The short hair that he had was getting cut and styled into a short afro. He would look like a black lady from the 1970's. Fiona explained, of course, that he would grow it out as a matter of course and he would try some get different styles, such as weaves. Fiona was so protective and loving with dad, and she said that she couldn't wait to make him her little sister and watch her blossom as a woman.

My hair was going to be wavy instead of curly. The girls spent about a half hour using the wavy curling iron on my hair after putting the spray in it. To help the style, they pulled my hair into a ponytail and put a couple braids and barettes into my hair. Fiona told us that we would learn how to do braids later and that we would enjoy spending hours braiding eachothers hair and doing makeup and playing dress-up. We would have so much fun wearing our L'Eggs brown sugar pantyhose. No more football for us! It was all going to be kotex, ballet, and boys.

My dad was just about done and I thought he was absolutely gorgeous. There was no trace of Joe and actually, all three of us would have no trouble passing as girls or being gorgeous for that matter. Kendra's hair was a mass of curls and her makeup was done in a style perfectly appropriate for a girl her age. I looked in the mirror and saw that I was finished, and I couldn't get over the downright hot black girl that I was. When I was a white boy, I never thought that black girls were hot, but now I was getting excited just looking at myself.

"Okay girls," said Fiona, "Its time to change into your outfits."

Fiona took us into the girls restroom. Even though we were all a different genetic gender, we had no problem with a loving presence like Fiona helping us dress in the nude.
I was given a white lacy bra, a pair of white cotton panties and a pair of medium denier white tights and I was told to put them on. I got on the bra over my massive boobs fine enough but Fiona had to help me hook it in the back. She showed me the right way to put on my pantyhose and soon my lower body was solid white to contrast with my ebony skin. It had been 5 years since I had last worn tights and I realized then how sexy they were and how hot I really felt.

Dad got into some beige lingerie and sheer pantyhose, and Kendra pulled on some black tights over black undies. Fiona helped them as she had helped me. It was so strange to see dad being called Monique and seeing another black lady pull up his tights like he was such a helpless little slut. What had happened to the masculine man who had used to take me fishing and hunting? How could we ever go back to the way things were after doing all of the girly things we were ready to embark on?

Fiona brought in our first outfits. Dad put on a short purple halter dress with a hemline that ended mid-thigh and he wore a pair of purple pumps. Monique put some gold jewelry on him and spritzed him with perfume. My little brother put on a pair of tap pants over his tights and a tight white top to go with a pair of pink keds. I put on a short black skirt and a tight black top, to go with a pair of high heels. I put on a small silver necklace and a couple of bracelets. I looked in the mirror and I could not believe the finished product. I looked like a little model. My top really showed my cleavage and made my breasts look perky as hell. There was no trace of Mike. We looked like a cute little family of women.

Fiona put perfume on all of us and she sat us down an painted our nails purple. We walked out and had our after pictures taken to go with our before pictures. The whole time I had a small erection building in my tights and I was really enjoying being a girl. "I'm really proud of you," my dad said to me.

"Dad," I said, "What should I do. I know this is embarassing, but I have an erection in my tights?"

"You'll have to wait until we get to New Hampshire tonight," dad said, "Then, you can take care of it as soon as Fiona OKs it."

"You think Fiona is hot, don't you dad," I asked?

"She is really a very attractive woman, but I'm already married."

"Are you excited about being her 'little sister'," I asked him?

"It seems like it could be fun in a novel way," he said, "I'm not worried about you little brother, but you need to try your hardest to just go with the flow for the next 6 months and not complain about anything. The stuff might seem "gay" to you but we all have to do it to prove that we are men and can handle anything."

"Okay," I said sheepishly. I did a little swish.

While we waited to depart, Fiona was giving us a crash course in girly walking and talking. She was clearly enjoying herself treating my dad like her little sister. Dad seemed to be enjoying himself.
 
 

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I was quite anxious and nervous as we got into a helicopter and flew to our new home in Dresden, NH. The four of us were taken to a big suburban house were we would live. We were told that the school and town center were only two blocks away.

We went inside and looked around and it had everything, Internet, 600 channels, the works. We explored all of our rooms. The only downside was that there was nothing manly anywhere in sight, like a pool table or weights.

First, I went to the bathroom where I pulled down my tights and panties and was finally able to go to the bathroom. As I was going, Fiona knocked on the door and reminded me that next time I had to sit down to use the toilet. The toilet would not flush unless a butt had activated the seat. "Young ladies never stand," she said.

I pulled back up my undies and pantyhose and I looked in the vanity. Inside was everything from mydol to Massengil. Under the sink there were packages of Tampax and Kotex. "My god," I thought, "This is what I am now."

I went up to the room that Fiona had designated for me and looked around. In the walk-in closet I had about 40 tops, 30 dresses, and some other clothes that had all been prefitted for me to wear. They were all really colorful and girly looking. I had what seemed like 50 pairs of shoes of all styles on the floor. I noticed in there that I had a pink ballerina tutu with leotard, as well as a white tutu. I had a couple blue cheer uniforms and what looked like 5 prom gowns that one could wear to a dance. Some of the tops had lace or ruffles on them. I pulled out a random top and it was a red shirt that had SEXY spelled across the bust.

In one drawer, I had a stockpile of panties and bras of various styles to last for a nuclear war. In the drawer down, I had about 60 pairs of tights and hose in various colors.
In the next drawer, I had all of my ballet leotards and wrap skirts. I also had pants, skirts, and booty shorts, as well as anything else a girl might need.

Fortunately, the room was not pink, but plain white, so I could at least retain a little bit of masculinity. I did have my own private vanity with an arsenal of makeup and hair products.

Fiona knocked on my door but came in without invitiation. "Later," she said, "I'll teach you how to do your makeup and hair yourself. However, it is late, so you have to go to bed. Tomorrow is Sunday, so all we have is church and a ballet practice. Monday, you start school. It will all be OK, sweetie. Your mom, Monique, was tired and fell asleep as soon as she got into her bedroom."

So I showered, shaved, and washed my makeup off. Before I went to bed, I was cold so I put my tights and panties back on. I looked down at my huge boobs and this whole thing didn't seem real. I was a black girl now, not a white boy, so my big boobs were just a part of me. Soon, I was asleep.
 
 

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My dad wore a black skirt-suit to church with nude hose, and he wore a big floppy hat on his head, which I thought was hilarious. However, Kendra and I were put into white tights and matching flowery sundressses, and we wore white headbands in our hair. It was crazy, putting our hosed feet into dress sandels and trying to maintain our modesty in our dresses. It was kind of satisfying to feel our whole lower bodies in nylon. We were all carrying purses and handbags that Fiona had filled with our feminine essentails. None of us said a word in church, and we just sat there silently and wanted it to be over. We did notice, to our surprise, some other groups of black women sitting there ashamed who we recognized as our competitors.

On the ride back home, Fiona said to us, "Girls, Brandy and Kendra, you will be dancing the 4:00 PM class twice every week. Brandy, even though you are 15, you will need to dance some "remedial ballet" with the younger girls, so you can get caught up to the teen level where you should be for a girl your age. So Kendra will dance at 4:00, Brandy will dance at 5:00 and twice a week at 4:00, and Monique will dance at 6:00 with the adults." Monique just sat there in the front seat powerless as Fiona drove home. It was surely killing him to see his once masculine sons, his pride and joy, dressed as pretty black girls. How could any man with any pride stomach seeing his boys in little leotards and tights doing sexy little dances and booty calls.

So we got back home and I waited upstairs for Fiona to dress me. She spent some time helping Kendra and then she came into my room. She was wearing a blue camisole leotard, white tights, and pink tennis shoes, and she looked HOTTT.

"Brandy," take off your tights and dress, "She ordered."

I stripped down to my lacy white thong and Fiona said, "We'll change your tights just so you don't feel dirty." She opened my drawer and brought me another pair of white tights and she had me step my ebony legs into them. I rolled the hose up to my knees and then I wiggled them up my hips as I stood up.

"You're doing a good job putting them on. You don't want to run them."

I got the waistband all the way up to my waist. Fiona helped me straighten my tights out and she smoothed the pantyhose over my legs. I was getting so aroused. I mean, I was a horny teenage boy who was being dressed by some hot lady. She was in her tights and she was close to me, rubbing against my back as she was getting me ready for another girly debut. It was embarassing knowing that a hidden camera in my room was filming all of this but I was enjoying the moment and I would deal with the consequences when I was a boy again. But now, I was a hot black girl playing dress-up with her mom's hot friend!

Fiona grabbed a hot pink leotard with short sleeves and had me step into it. I put my arms through the sleeves and I looked in the mirror. I was a hot black girl ready for dance. Because of my shaping panties, I looked just like a smooth girl around my crotch. I was told that I would wear tennis shoes to ballet but that I would put on my slippers when class was ready to start. My legs looked sooo good in tights, and I thought it was cool how my white legs came out of the holes in my pink leotard and how the leotard covered my whole body. The leotard was really tight and was really pushing my boobs up and my bust looked really prominent. I was such a hot, shapely black girl with a cute ass. I wondered if there would be alot of hot girls at dance and if they would want to date a guy who was trying to be a black girl. I thought that all the girls would look really cute in their dance outfits, just as they had when my older sister had taken ballet.

I was going to be excited to see how my brother and dad would look in their ballet gear. I stepped into my pink keds and Fiona touched up my makeup. She tied my ponytail into a "ballet bun."

I was ready to debut for everyone my ballet clothes and I stepped out of my room. My dad was wearing a red cap-sleeve leotard with white tights and he had a pink "ballet bag" with a spare leotard and tights and his ballet and tap shoes. He was every inch a gorgeous ballerina. My little bro was wearing a baby pink leotard with white tights and his hair was styled in a ballet bun. He too had a ballet bag with "essentials." Fiona handed me an identical bag in case I had a run in my tights.

"Wow Brandy," you look so hot," My dad said with full conviction of a mother raising a teen daughter. Her daughter was ready to blossom and grow into a full woman. At ballet class, we would learn the grace and poise we needed.

Fiona pulled three small spray bottles out of her dance bag that looked like three small containers of mace. "This is girlie spray," she said. Spray this into your mouths twice every day and your voice will begin to register to that of a woman. This spray has all of the hormones you will use and soon you will start to see some feminine development. She explained to us that we would have some breast development and our hips would widen. This was designed especially for black women so our voices would develop that ethnic African tonation in one weeks time and our hips would get extra wide. Eagerly, we sprayed some into our mouths. I planned to use extra because I really wantedt that money.

So we marched out of the house like an army of ballerinas and drove to the ballet studio. Fiona told us that later, as we matured as girls, we would have the privilege of wearing wrap skirts or sweats on our way in so we wouldn't be so "exposed" to staring guys. For now, we would have to have our legs and buns exposed so we could empathzie with actual women.

We entered the studio and we were greeted by a petite blonde girl named Amanda, who was dressed in ballet-teacher gear. We said nothing more than "Hi," in our highest voices, since we would still sound like white guys. We knew we had to try hard to be feminine.

I felt bad for Dad who had to sit around for two hours to wait to dance while his daughters took their classes. However, Fiona explained that it was the woman's role to chauffeur her daughters to all the activities and that she had to put up with the irritants along the way. Dad/or Monique, would be the housewife in the family and he would be responsible for the domestics while Brandy and Kevin had to focus on being as girly as possible so we could have a good chance of winning.

My brother and I, dressed like little dancers, walked into the main ballroom where Amanda was getting the music ready. There were about 8 other little pre-teen girls warming up who were dressed in tights and leotards who were ready and eager to start class. They all looked so cute and eager. It was a far cry from my old football practices where the coach yelled at us all the time and made us run laps and do drills. It was going to be a refreshing change to get to do something halfway civilized and intelligent for a change. I thought I would have more fun learning dance steps.

Two of the girls were older-looking black girls around 14 years old whom I automatically assumed were in my situation since they were clearly here for "remedial" ballet. 2 of the girls were little Moslem girls wearing their head coverings but they still wore pink tights and leotards and showed off their legs(so much for modesty). The other two girls were little black girls but I was unclear if they were really boys or not.

The older black girls sort of shyly hid in the corner and were reluctant to talk, as was I. They seemed quite timid and ginger about this whole thing. I knew that the key was to relax and just have fun, so I was going to make the most of it. I walked up to the Middle Eastern girls and introduced myself as Brandy. I noticed that the one girl had an image of Princess Jasmine from Aladdin on the front of her leotard and the other had a Beauty and the Beast themed leotard.

"Hi Brandy," they said back to me. "You have really pretty hair." So I was on my way to acceptance. Hopefully the viewing public would see that I was trying hard to fit in as a girl.

The girls were ready to ask me questions, but Amanda said, "All right girls, everyone get to the barre to begin warmups." She put some waltzy piano music on the boombox.

For half of the girls it was obviously their first dance lesson and I had no clue what I was doing. Fiona, another coach, and Amanda would take turns helping me and the other girls do the basic moves. It was over my head but they were moving my legs and arms to put me in the right positions.

After 15 minutes of warm-ups, they told us to partner up. The little moslem girl with the Jasmine leotard chose me. I was glad because she was the only girl who seemed like she knew what she was doing in class so I would have an advantage over the other boys/girls. Even though, she was only 12, she looked really cute and I actually thought that if I was a guy I would consider asking her out, even though she was perhaps a little young. For some reason, I thought it was strangely arousing how she still wore her headcover but looked so good in her tights and had a nice, developing body.

"I'm so glad wer'e going to be ballet partners for the dance, Brandy," she said to me. "I'm Zafira, by the way."

"I'm glad you picked me Zafira," I said. I was glad it came out as smooth as it did. I tried to put a little urban inflection in my voice.

Amanda handed each group a little piece of paper with some song lyrics on it. I looked at the song.

I'm all dressed up in pretty clothes
And going out to tea
I get to wear my pink dress
All the boys look at me.

"I know this song, I'll work on the steps with you later," said Zafira.

Amanda changed the CD track and the song music with a babyish girly voice began singing the above lyrics. Amanda told us to follow the steps. It felt really weird trying to do the girly moves in my ballet slippers. I was trying to point my toes like a show girl and be graceful as i shased around the floor. I watched as the other boys/girls tried to keep up with some difficulty. Zafira took my hand and "led" me like a ballroom dancer as we went through the steps. She held my hand as we went off for break.

"See you next week," Zafira said to me after the class was over and she left the studio.
 
 

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The class was of course so much fun and was over with WAYYY too soon. But I still got to then keep going and dance with the older teen girls. 5 more black girls came in wearing ballet gear and four totally hot white girls were with them. These were the kind of hot girls who were WAYY out of my league at my old school. I assumed that the black girls were my male competition.

So with some basis in dance now, I was able to get through the young-teen class, even though it was much more difficult. But it was still fun, and I was totally going to do ballet, but as a boy, when I got back home. In any case, since the tan wouldn't wear off for a while afterwards, I would probably get to do some ballet back home as Brandy, and the girls at my High School would have no idea it was me, since the show wont even air until 2010! I'll get to change with them in the locker room and everything! It will all work out, and being a black girl in disguise will have some advantages.

But I was beat after my 2nd class, and I can't remember a football or wrestling class ever being quite that tough. Ballet would totally compensate for my other sports and I would totally be coordinated when I went back to wrestling. I went into the girls room and checked my makeup, and I wiped off some running mascara with a baby wipe in my purse.

My dad went in to start his class and my brother and I had to wait in the lobby for an hour. But there were the five other black girls/boys sitting out there who were waiting for their dads/moms. We all looked so adorable in our hot outfits and I was sure that the hidden cameras were having a field day with 7 white boys sitting around dressed as little chicas. Two of the boys were wearing black tights and black leotards with short attached skirts. Another was wearing a plain black leotard with thick nude tights. The other two got purple leotards and pink tights. I felt so ridiculously feminine sitting there. I had to constantly remind myself that I had to keep my feminine poise so I had to cross my tighted legs, sit up straight, and keep a smile on my face.

We all made some subdued small talk. No one wanted to show any weakness or actually admit that they might be enjoying this. I talked to Leticia, one 16 year old, who had been a computer geek kind of guy and he said that he never expected to do anything like this. He wanted to go on an outdoor adventure to prove his manhood to the world. He looked so uncomfortable in his spandex and nylon.

So after a long day, we drove home as a new family, missing our real mom and sister. We ate a quick meal, and Fiona told us to meet in the living room for our first feminine lesson. We kept on our ballet outfits and Fiona was ready with packages of Tampax and Kotex.

She explained female menstruation to us and the basics of female puberty. She told us how we would begin to see some breast development and our hips would widen and our muscles would soften. We would develop fat deposits in our hips and our body weight would transfer to our lower body. Though my dad was older, he too would redevleop like a teen girl would and our male puberty would come to a screeching halt. Not to worry, though, after all this was over our body would start producing testosterone like normal again and we would be back to our old male selves. But for now, our bodies would be flooded with estrogen so we could be hot ebony babes.

She told us how girls use kotex to stop menstrual bleeding. We wouldn't have to worry about tampons, since we had no female cavity, but Fiona wanted us to experience Kotex. Then, she told the three of us guys to take off our leotards and pull down our tights and panties to our knees. We had a breif chance to admire eachother's topless female bodies. My dad's bust jiggled whenever he moved. Fiona told us that from now on we would have to start wearing bras to dance class, since we were bouncing more than she had initially first thought we would.

Fiona opened up a package of Kotex as we all dropped our white tights and panties to our ankles and exposed our smooth black butts. I thought it was amazing how femininely dad was able to drop his tights. Fiona took my dad and showed us a thing that looked like a small diaper and put it over the top of my dad's shaper panty. She pulled his black french-cut panties back up to keep the Kotex on and had him re-raise his tights to his waist. As she had done on my dad, she put Kendra's kotex on him and got his tights back on straight. Then, she helped me with my Kotex and re-wiggled my tights back up over my sexy but. We all looked like we had some bloating down there.

Feeling as gay as could be, we put our leotards back on. I felt like a baby girl wearing a diaper, and my once masculine dad was now totally humiliated. We all looked so funny with the Kotex on but Fiona said, "This is what girls have to put up with all of the time, and you boys need the full experience. Just wait until we wear empathy suits to simulate pregnancy."

She continued, "For the first couple months, we will do thngs developmentally appropriate for younger girls. We will have tea-parties, play dressup, and play with dolls. We have to resimulate the female development process over six months. Tomorrow night, I will show you some basic makeup and hair tips for black girls so you girls can start to spread your wings. Right now you all are totally dependent on me, but soon, you will be confident, sexy women."

Class was over, but tomorrow I had my first day of high-school. My uniform had already been laid out for me, and I was going to have to be really careful not to let the boys look up my skirt, even though I would wear panties. But I took off my ballet gear, showered, and soon I was fast asleep.


 
To Be Continued...

The Challenge Part 002

Author: 

  • TylerD

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

The girls start school and Fiona eases them into femininity
 

The Challenge: Part 2

By Tyler


 
Fiona came into my room early the next morning and woke me up. She was carrying a cardboard box into my room and she began to pull out some pink plastic packages. I was groggy, but I sat up and saw some Barbie dolls, and I was intrigued. Yet, to my surprise, they were black Barbie dolls.

"This is Ballerina Barbie," said Fiona, showing me a black doll in a pink tutu and tights, "and she will be your new best friend." I took the doll, happy to accept the gift.

I looked in the box and saw barettes, fake jewelry, and toys that were clearly aimed towards 7 year old girls. I was given a dollhouse with all black dolls for the inside. Fiona said, "For a couple weeks, we will be living in little girl mode. You basically have to discard all your male traits and relearn everything girls do from the ground up."

I can't say I was terribly excited to have tea parties with my brother, but I would just accept. Fiona put up a couple posters of Barack Obama, Kanye West, and Jamie Foxx. As a white boy I had totally been for McCain, but now, I was beautiful Brandy. "From now on," we have to get you totally thinking like a boy-crazy black girl."

"Am I supposed to flirt with or date boys at school," I asked?

"That is up to you," Fiona said to me, "But the more you embrace being Brandy Washington and act like a teen girl, the better you are likely to do with the viewing public. In any case, we have to get you dressed for school. I have your uniform here for you at your vanity."

It was a schoolgirl uniform with a blue button-up blouse, a plaid skirt, and mary-jane shoes. Fiona told me that I had the option of wearing black or white tights on a daily basis. I was told that the school was a public school with a uniform policy.

So I grabbed a pink bra and pink panties and got them on quickly. I had to put on a kotex as Fiona ordered. I was hungry and wanted breakfast. I was hoping that Monique had gotten into domestic goddess mode and had started on some waffles. I decided on black tights since I had been in white tights for the last two days and pulled them on. Fiona put some makeup on me and brushed my hair. I put on my skirt, blouse, blazer, and cute little schools, and I caught an image in the mirror of a cute little black girl ready for her first day of school!

My brother came out of his room at the same time as I did, only since he was younger, he had to wear a jumper and he had chosen white tights. I walked into the kitchen and saw dad wearing a blue dress with an apron and he was slaving over the stove, trying to master the art of cooking which he had no experience with. Fiona was in a skirt suit and was getting ready to go to "work." My dad turned around and saw his hot little daughter and sad, "Wow Brandy, you make one cute girl."

"Thanks mom," I replied coquettishly. I was flattered that dad thought that I was feminine. I knew I would have no trouble passing.

Fiona only let me eat one pancake with syrup since I now had to stay slim. Dad packed me and Kendra in the minivan after we had eaten and he dropped us off at school, giving us each a kiss. I'm sure that the cameras were eating it all up.

So once I was going through my morning classes, I didn't think anything of sitting there as a black girl. The only thing kind of strange was the feeling of the kotex against my crotch and the tightness of my hose, reminding me of my girlishness. It had almost kind of skipped my head. My voice was still husky so I just said little. Fortunately, I wasn't asked to say anything longer than a sentence. At the school, though, there were a ton of cute girls. I tried to keep an eye out for any of the guys in my dance class but it was a huge school and I didn't see anyone.

At lunchtime, I went to the cafeteria and purchased a ham and cheese sandwich. I was going to find a quiet place to sit alone so I could hide better but as I walked past a table full of black girls, they called me over and invited me to sit down. I smoothed my skirt and crossed my legs.

"Heya Girlfriend, was your name," one of them said?

"Brandy," I replied, "I moved here from Tenessee."

"Hey, wasn u in my ballet class," another one of them replied?

"I sure was," I was quite nervous. But it was clear that this black girl, Krystal, really was female.

"Yous be a good dancer," she said, "Cheerleading tryouts are on Thursday. You should totally come. U'd definitely make our squad."

So I had gotten a head start! One of my challenges was going to be to be a cheerleader, and here I had basically an open invitation. I was definitely in the lead. The money was mine.

I kept my feminine composure and said, "I'm so exicted, I was a cheerleader at my old school." Even though I hadn't been I had had a crush on one of the cheerleaders and because I followed her around I had learned basically everything and could recite the cheers she did in her sleep.

I had made friends with the clique of black princesses, and I was on a high. Those girls were much nicer than I had expected. When I was a boy, the black girls had always seemed so alienating and threatening.

I got to change into a T-Shirt and Short Shorts at Gym Class that afternoon inside the girls locker room. It was really cool playing basketball with a bunch of girls instead of rough guys and I dominated the court. I just had to start shooting the ball like a girl or serving the ball in Volleyball with that girlish serve. But I had to be discreet about watching the girls change inside the locker room, lest I be branded a lesbian. I didn't really want anyone staring as I put my kotex pad back in. I put my tights back on and waited for my dad to pick me up.

When I got in the minivan with my little brother, my dad asked me, "So how was school?"

I said excitedly, "I was already invited to cheer tryouts. How was your day?"

"Fiona worked with me endlessly. I spent all morning cleaning when I used to play golf. There is so much to learn about being a woman. And I have to start work at Hooters in one week. When we get home, Fiona has us scheduled for a tea party, than another feminine lesson, and then we are going to practice some dance moves. And I am already exhausted."

When we pulled in the driveway, I jumped out of the car and ran up to my room. I decided to spend some time modeling some of my outfits. I had alot of tops that were clearly designed for black girls to wear. I put on a couple pairs of really tight studded pants that rode low around my waist. Friday, of course, was a free day at school, when students could wear whatever they wanted. On thursday, students could wear dressy outfits to school, but boys had to wear a shirt and tie and girls had to make themselves up. But now, I was so on my way towards becoming a ghetto princess. Even though I had hated rap previously, I put some rap music on my radio and danced around to it, shaking my butt. I collapsed, laughing, onto my bed. Then, I took my ballerina barbie and a small brush and spent 20 minutes just doing her hair. Yes, Mike was vanishing and Brandy was emerging. Mike would never have done all of this girly stuff. But, I didn't miss sports, or video games or anything like this. I was having alot of fun trying on all my tights and playing wih my dolls and toys. Ballet was the overwhelming thought in my mind.

I also had received some black Bratz Dolls and I paid close attention to their outfits and hairstyles and began to consider adopting them. Fiona had told us that soon we would go shopping at the mall and we could pick out some girls' clothes that we liked.

So around 5PM Fiona came home and called her happy little family together in the living room. My dad had gone and changed into a French Maid's uniform and he was wearing white tights under a very short skirt and apron. I figured we were going to play tea-party. I had already pulled on a navy blue leotard with an attached flowery skirt over my white tights, and my brother was wearing a forest green leotard and white tights.

"Kendra, Monique, and Brandy," said Fiona, "I'm going to need you to change. You girls can keep your white tights and ballet slippers on but I will need you all to go into the den and change into the leotards I set out for you. We eagerly went in to see what surprise was in store for us.

On the table were laid out three leotards, each in the correct size to let us know which ebony princess it was for. For Kendra, he had a light-blue leotard laid out for him with a Disney promo image of Cinderella on the front. My dad had a teen-sized aqua leotard with a scene from the Little Mermaid and Ariel depicted on the front. And for me, to my intense excitement, I saw a pink leotard with Pocohontas on the front. I had thought that the leotards that the Moslem girls were wearing yesterday were just so adorable and now I was actually getting a chance to wear one and just be ever so girly. I couldn't wait to wear one to my ballet class tomorrow. I guess Fiona was giving them to us so we could feel like grade-school girls and rewire our brains to think like little sweethearts. It was going to be tough to take a strong, breadwinning man like my dad, break him down, and rebuild him up as a mother, woman, and domestic goddess. But dad looked like a kid in a candy store when he saw Ariel on the leotard he was destined to wear as Monique Washington, mother of two darling teenage colored girls.

"Mommy, I'm so happy I get to be a little princess," I shrieked excitedly. It was not a desire to please the cameras but a genuinely girly desire that was overtaking me. I guess the hormones were working some magic on me. Being in tights all the time was confusing my brain.

My dad was an ebony goddess as he pulled off his Maid's dress, revealing a red lacey bra, and he took his little leotard and put his legs into the holes. He pulled the fitting nylon garment up over his tights and over his shoulders. He wiggled his arms into the sleeves. It was a little ridiculous; a grown black woman dressing up like an 8 year old ballerina. But dad had to learn how to be a little girl if he was ever going to be successful and this was going to do the trick. It was just so beautiful, a sable princess with long legs in tights wearing the cutest little leotard. It was hard to believe that he ever could be a father or a man with the smooth crotch of his leotard and his girly, effeminate actions. You could see Ariel the mermaid under his black breasts and I knew that the man my dad once was was gone forever. I imagined him in a tutu dancing Giselle on a packed stage, being held in the arms of a male danseur. There were a couple guys in the adult ballet class and I wondered if he had caught their eye.

I was so transfixed watching him that I missed my little bro pulling on his cinderella leotard. His leotard had a small attached skirt, and when he finally had it on he looked more like a 7 year old girl than a 13 year old girl. Kendra had no qualms at all about ditching his boyhood; he was far more secure than I. My dad pulled my brother's masses of curly hair back into a ponytail. It was such a sweet mother/daughter bonding moment that I knew we could never experience as males. Here we were, three straight guys, getting to be princesses and ballerinas and play with barbies and have tea parites! Reliving life, with my dad as my mom and a little sister was going to be great. He seemed so much nicer and more attentive when he was in female mode.

So while I was standing there in just my bra, ivory tights, and panties, I grabbed my Pocohontas leotard and pulled it up my body and wiggled it onto my busty frame. I modeled for a second in the mirror and was joined by my dad and brother. We all struck sexy poses in the mirror and blew faux kisses. We stuck out our legs like show-girls and did some provocative hip swaying and what we thought were stripper moves. We looked like three black teenage girls trying to dress like little 8 year old ballerinas, and we loved it. I thought that we just looked so sexy and adorable. I was sure that this scene would find its way all over Youtube.

"Sorry to interrupt ladies," said Fiona as she came in with a digital camera. She snapped about 100 photos of all of us and we struck poses for her that were borderline obscene. I got to hold my dad and little brother and we snapped group photos. We gave up everything for the moment.
"I thought you girls would just love this," said Fiona.

"Girls," my dad said, "I'm so glad that we get to have this experience. We shared a big group hug. This could have never happened back in the real world." Even though dad might have wanted to resist what was happening to him and keep his manhood, he had to be brave and set an example for his sons. Doing this now would make him a stronger man later on in life. It was time for us to take our girly spray and we happily took our hormones. We couldn't become big girls fast enough

Fiona brought us back into the living room where she had a little tea-party set up. Us girls sat down and had the best time, taking turns and being polite. Dad was such a classy lady pouring tea for us. His bust looked absoultely great in his little-mermaid Leotard. I felt absolutely great in my Pochontas leotard and I noticed for the first time what an awesome female figure I really had. Living as Brandy was so natural, and I didn't want to ever have to give it up; I was just so damn sexy, like the girls I admired. Now I was a hot girl. I loved how my tights brought attention to my meaty and shapely legs. All of us guys looked good with our big fake boobs, and we couldn't wait to grow our own.

"So do yo boys like being girls," My father asked us?

"I'm just doing it to win," I said, but I was starting to feel like I was lying to myself.

"I love being a princess," said Kendra. "It is so much more fun than being a stupid boy and having to fight all the time."

I asked my dad, "do you think that you'll be able to go back to being Joe?"

"I'm just playing a game sweetie, but I just love how close we are as a family now that we are all girls!"

Dad poured some more tea. I noticed that he had painted his nails red and apparently Fiona had given him a manicure today.

Fiona came back in and began to give us another feminine lesson. She showed us all of her hair and makeup tips and from now on expected us to do our own basic beauty regimen. She would still assist us if we needed help(which we knew we would), but we felt good knowing that we were moving along. She had my brother and I practice putting braids in eachother's hair and we practiced using things like eyeliner for a couple hours. It was fun getting to put mascara and lipstick on dad, he was having the time of his life doing my pretty face, much like when we used to play football together in the backyard. Fiona told us beauty tips specific for women of color such as ourselves. Finally, she introduced us to L'Eggs Brown Sugar pantyhose, and said that it was hose designed just for black women and that we would wear them when we started getting out and mingling. One thing was clear, we were no longer white men but black women, and we were only thinking of ourselves as Monique, Brandy, and Kendra Washington.

So we had had feminine life skills pounded into our heads all evening, driving out our male thoughts, and then Fiona had us line up in the living room. We were still in our Disney Princess leotards, and she began to explain to us what we were doing in Ballet Class yesterday and making sense of the dance moves and ballet positions. It was great to receive individual tutoring, since I wanted to impress Zafira and the older girls with how good of a dancer I was. Then, Fiona went over some basic Cheer moves and showed us some ballroom dancing steps(for women of course.) Dad was really catching on and I couldn't believe how feminine him and my brother were becoming. It was great watching Fiona help my dad with ballet positions that I had already mastered. It felt good to finally beat him at something.

Fiona was so loving and tender when she helped me and my brother learn our dance steps. She was so good at comforting us when helping us dress up. Fiona worked so well with my delicate little brother, who needed a strong female role model. It was so cute when she would help him pull on his pantyhose and dresses when we had to change to go somewhere. My only concern was how Kendra Washington would adjust back to being Kevin Thompson.

I wished I could call my mom or my sister but we had no phone and we would be kicked off the show if we called the outside world to tell them what was happening to us. My mom thought that we were all rafting down the Amazon river. In reality, we were developing into full-fledged women.

It was about 9 PM when we finally finished and I still had to do my homework. I was still in my Pocohontas leotard and I collapsed on my bed, dead tired.

###################

The next day at school I had noticed that my voice was starting to sound higher when I would speak. When I was changing for gym, I felt as if my arms were somewhat thinner.

I caught this little white boy ogling me in science class, so I smiled back at him. He couldn't take his eyes of of my ebony legs in my sexy white tights. It was weird to think that I could give a guy a boner. But Fiona had told me that I would be an absolute boy magnet.

When I got home, I knew that we all had ballet that evening, so I pulled on my white tights and I put the Pocohontas leotard back on. Before that, much to my excitement, I had discovered a pair of Winnie the Pooh pantes in my underwear drawer and put them on, and I was wearing them under my tights and bodysuit. I had a huge urge to wear the panties under my tights, but i did not want the pantyline to show, so I looked for something to cover up with. I put on a pair of tight red shorts that spelled out DANCE across the butt. I spent several minutes modeling in the mirror and I coudn't fathom how I had been a red-blooded American white boy not one week ago! Now I was a little girl to die for. I grabbed my purse and dance bag. I wouldn't feel so uncomfortable from no on because I was wearing a bra and I wouldn't bounce uncontrollably like I had last week.

When we all got to the ballet school, Zafira was excited to see me. I told her that I had gotten to practice the dance a little bit and had memorized alot of the moves. Zafira was wearing a pink leotard with blue trim and white tights, in addition to her headcover. "You look cute today," she said. I had been worried about what the older girls might think seeing a teen girl nearly of driving age wearing a Pocohontas leotard, but I decided to throw caution to the wind and go for it. I would never hear the end of it if they found out about my Winnie the Pooh panties. I was only going to get to be Brandy for six months, so I would enjoy it. My little brother had put on a black leotard with an attached skirt over a pair of black tights. Looking at him, I would have never suspected that he could be a boy.

When my brother danced, he looked really cute because his little skirt would fly up and reveal the bottom of his leotard to the world when he twirled. But he just looked so angelic, a 13 year old boy living a ballerina fantasy.

So confidently, I was able to do the barre work and warm-up exercises extremely gracefully. When we got to the actual dancing, I loved getting to use Jazz Hands. I could tell Zafira was impressed with how good I performed the little song and dance routine and I was starting to wonder if I might have a future as a ballet dancer. We looked so cute singing and dancing the little song together. I felt much more comfortable around the younger dancers than the older dancers, since I was too inexperienced as a girl thus far. My dad was watching us through the window with tears of joy. I remember when he used to watch my football practice. Now, I would be a cheerleader in the snazzy halftime jazz routine. I noticed that I was starting to walk with a sassy sway of my hips and I was starting to adopt a more feminine posture and body language.

I did little pirouettes and twirls and arabesques. I loved just leaping and frolicing around the floor in my tights. The feeling was unbelieveable.

When the older girls came out, however, they kind of gave me looks of disapproval for wearing such a babyish leotard. So perhaps I had shot any romantic chance I had with them. No girl wants a sissy guy who dresses like a little princess. They don't even like run of the mill crossdressers. But if I won the show, I would be famous and have girls lining up at my door.

I had taken off my red dance shorts to show my behind. I knew that my panties were showing under my leotard and through my tights but I needed more freedom of movement. Just as I was feeling extremely awkward, Krystal bailed me out when she walked in the ballroom and began to talk to me. She was in a pink leotard and pink tights, but she said to me, "A Pocohontas leotard, I guess you want to look cute today."

She could tell I was embarassed, but I said, "Well, all my other clothes are in the wash, so I had to pull one out of my stock from when I was a little girl."

"Relax," she said, "I like to play dress-up too. You can come over later sometime and we can try on my clothes."

"Cool," I replied.

"Well, I can't wait to see you at tryouts. I'm meeting my boyfriend later," she said. So I guess I had no chance of being her lover or whatever.

Without thinking, I said, "Can you help me find a cute guy around here?"

"Sure, she said, I'll introduce you around at school."

So I was petrified at the thought of being thrown into the dating fire with some horny teenage boys. What would they do when they discovered my true gender. But in a way, I was kind of excited about exploring my feminine side. I would love to date a girl my age, but what chance would I have if they thought that I was a black girl?

In the mirror, all I saw was a beautiful black girl at a ballet class. I thought that I had a better chance with Zafira, since she probably looked up to me since I was a few years older. She asked me if I would be her BFF and I accepted.

Today I was performing the steps with the older girls but I was doing a better job keeping up than last time. What would the guys on my wrestling team say if they saw me now, prancing in nylon? I bet they would want my digits.

Halfway through class, however, emergency struck and I had to use the bathroom. I had to do a #2. I told Fiona, "I have to go Poo-Poo." I didn't intend to sound so babyish. She was in her basic ballet gear of a simple black leotard and black tights, to separate herself from the girly-girls.

Fiona grabbed my hand in the middle of an exercise and led me off towards the girls room. I was still clumsy when it came to pulling off my leotard and pulling down my tights, so I needed Fiona to help me. But I really just wanted another opportunity to bond with Fiona.

We entered the girls room and walked to one of the stalls. Fiona went in there with me and assisted me in taking down my leotard. She peeled my leotard down to my waist. Then, she took my tights and pulled my hose and my leotard down to my knees. I felt so helpless, yet, good. She took down my shaper panties to free my bottom and I sat down to go poop, with all of my girly clothes still gathered at my knees. Fiona watched as I struggled to go.

"All done," I said, as I stood up. It was my natural instinct to wipe my butt but Fiona gently took my hand away from the tissue paper. She told me that I was being treated like a 5 year old, and she wiped my butt for me. It was strangely erotic and I developed an erection which Fiona noticed.

"Its all right sweetie," she said, "You can take care of that when we get home."

It took a few minutes for me to settle down and once I was calm Fiona pulled my shaper panties back up to tuck me in. Then, she got my tights back up and she got me back into my leotard. Satisfied, I went out to finish class.

After class, I was excited, since Fiona informed me that tomorrow all of the males would have our first feminine challenge of the show! All that went on that night, however, was my brother and me watched excitedly as dad modeled the Hooters girl outfit that he would wear to work! My dad was nervous thinking that he would have to flirt with guys as a waitress but deep down we knew he would do just fine and we gave him plenty of hugs to reassure him.

To Be Continued.

The Challenge Part 003

Author: 

  • TylerD

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

The guys continue to develop as females.
 

The Challenge: Part 3

By Tyler


 
The next couple days flew by and I knew that it wouldn't be long before I could get back into my jeans and go back to being Mike. I had learned my lesson from wearing the Pocohontas leotard at ballet class and I knew that if I was going to be accepted by the girls at my school, I had to dress in more mature outfits. My little brother, on the other hand, could still get away with wearing whatever he wanted, since he was still at the middle school level.

At school, I spent all my time with my gang of black girls. I was glad that I was doing this experiment, since as a white boy I would not have had a chance to meet such great people. I was excited to hang out with Krystal on the weekend. When we sat around at lunch, I was taking mental notes, on what they wore, and how they talked. Soon I was thinking in black-english vernacular and I was adopting some slang. I was trying to model my girlie personality on thiers, and I was trying to fit in and be like them. But I felt like I wasn't just a guy trying to win an acting competition, but a budding girl stepping into her womanhood.

Fiona had me read, "Are you there, its me, Margaret." She filled my bookshelf with Cosmo, Ebony, Black Woman, and all the magazines she thought I might need. I was reading all the time and I was just devouring information on makeup, boys, and clothes. It was alot more interesting to me than the score of some meaningless football game. I couldn't wait to "grow up" in the eyes of Fiona. I would spend time trying to improve my makeup skills, and I would braid my brother's hair.

My brother and I used to fight all the time, but we had done a complete 180 turn the last week and now we did nothing but try on eachother's clothes and talk about hair and boys. Kendra would discuss boys in her class all the time and how cute they were like she was discussing the weather. I still considered myself straight, but I think the hormones were starting to get me a little boy-crazy too. But for now, me and my brother were having the time of our lives wearing dresses and leotards and talking about the boys we'd like to date. After this was all over, we could go back to being Mike and Kevin but we just wanted to live in the moment. My dad may not have been happy about his son's embracing the feminine life, but he was just happy that we were getting along. In any case, my dad was far too concerned about his upcoming debut as a Hooters Waitress and all of the female training Fiona was giving him to worry too much about the future. We were all excited about the possibility of winning the prize.

So at cheerleading tryouts, I was a shoo-in. My knowledge of the cheers was marginal at best, but I impressed all of the girls there by my handsprings and backflips and there was no doubt that I could learn the easier stuff. In addition to cheering, the squad performed a jazz dance routine at the halftime of every football game.

I had a ballet class right after my cheer tryouts and I slipped on a black leotard with white polka dots and an attached skirt. The attached skirt had a little white rose on it and ruffles underneath. This was the kind of leotard that would reveal your bottom when you twirled. It was kind of overly feminine, but I had been admiring it and I was determined to wear it. I had white tights on underneath, and they made my legs look long, smooth, and sexy. I loved the feeling and sound my legs made when my tights rubbed together and I could feel the swish of my skirt and a cool breeze on my nyloned legs. I spent some time on my makeup and I was the picture of girlishness.

I went into the living room and my dad said to me, "My god Brandy, I have never seen you looking this feminine."

I did a little twirl and said, "My god mom, I've only been a girl for one week."

What I noticed now was that my natural voice, if I did not try to change it, was still deep but decidedly female. In the mirror, I saw that my hips were about an inch wider than they had been last week. I noticed that my dad's arm muscles seemed to be getting smaller and his butt was a little bigger too.

"Its so cool how we're starting to turn into real women," I said to my dad, "I bet mom wouldn't even recognize us.

Dad said to me, "I can definitely feel the changes. I'm kind of excited. It will be nice to just be able to talk and have an actual female voice come out." Dad then went upstairs to get into his ballet gear. Five minutes later, dad came down in a pink leotard with an attached skirt and white tights. What shocked me was that on the leotard was an image of Snow White. My brother was at his side wearing a black leotard with a small pink rose between the breasts and red tights.

I was so jealous of my dad. Here I was wearing such a cute outfit, and my dad came down looking so sweet. "Where did you get that leotard," I asked him?

"I found it at the back of my ballet drawer," he said with a feminine lisp.

"I am so jealous," I pouted.

"You can borrow it anytime," he said as if he was talking about baseball cleats. As he got closer, I could see that he was wearing a pair of pink lace panties over his white tights but under his leotard. I thought it was hilarious that you could see the lace fringe of his underwear sticking out from the bottom of his leotard. I wondered what Fiona would have to say about that. Between the Snow White leotard and his visible panties, he looked like a 4 year old girl who had dressed herself for dance class. And this guy was wearing a flannel shirt 8 days ago?

"Uh, Mom," I said, "If you're going to wear panties to ballet, you at least have to wear them under your tights. I can see your Victoria's Secrets."

"I know baby," he said, "I'm just going to try it this way for once."

I felt embarrassed in the way a mother might embarass her teenage daughter with poor fashion sense. But there was no time to argue as Fiona came out of the bathroom and herded her girls into the minivan.

At dance class, Amanda had some big news and told us that our school, in conjunction with two other dance studios, would be performing theh ballet "Sleeping Beauty" in three months. I didn't know much about it but the other girls got excited. We were told that everyone had a chance to audition for any part.

I sat in the studio and watched the adult class and I watched Dad go through all of the ballet moves he had been taught. I sat in the chair and put my brother's hair in some beads while he looked through a dancewear catalog and imagined how he would look in all of the sexy costumes. I got to hang out with Zafira, Krystal, and some of the other girls, but I was still too nervous about talking too much and giving away the fact that I was a boy. I did make arrangements to hang out at Krystal's house Tuesday night after dance.

#########################

As a family, we had been looking forwards to Sunday afternoon, our one week anniversary, because we would take part in our first feminine challenge. We received letters from Matt at our homes to get dressed up in the cutest outfits that we could put together, and our coaches would drive us to our challenge.

Fiona got me into a peach colored bra and panty set. She put a pair of black pantyhose on me and then put a tight blue top with long sleeves on over my bust. I put on a black leather miniskirt and a pair of black pumps. She then sat me down at my vanity and spent a half hour putting up my hair into a really cool style with braids and beads. She did my makeup tastefully and painted my nails blue. When I was all done, I couldn't believe the finished product. I was finally an actual teen girl instead of a little grade-school girl. I posed for about 20 minutes.

I thought that my brother was still too young to do anything with being sexy but Fiona dolled him up in a pink top and a pair of black jazz pants. My dad put on a lilac-colored dress with a flower print that ended mid-thigh and he wore sheer pantyhose underneath. He took the brown sugar pantyhose out of the package and noticed the black girl on the cover. "Oh well, I guess that is me now," he said. I noticed how the hose colored perfectly with his ebony legs and he looked very natural. We spent some minutes judging eachother's outfits but there was no doubt that there were 3 sexy, man-starved, gorgeous black women in the family who wore outfits screaming, "TAKE ME." I was hoping that the challenge had something to do with boys.

We were as excited as little kids on Christmas morning as we got into the minivan. My father and I were wearing short skirts so we had to cross our legs and try hard to maintain our modesty. Fiona really hadn't had a chance to get us used to short skirts and I had only worn them once before. Still, all of us guys were absolute goddesses. It was the first time i had seen my dad in something cute besides a ballet outfit outside of the house. He seemed to be more comfortable as a woman and it was nice to see him loosen up and get completely into Monique mode, instead of the timid way he usually was. He was laughing and joking with Fiona the whole way there, talking about how cute guys like Taye Diggs and Will Smith were. I was shocked to see my dad talking about how sexy guys were, but our brains were rewiring and we were redeveloping as women. Dad was being flooded with female hormones and he couldn't help himself. He told Fiona how much he loved his brown sugar pantyhose. Then, he looked back and said, "You girls will be in heaven when you put these tights on."

So we arrived at a convention center and our heels clicked as we walked into the room. Matt was in there shaking the hands of 15 other black women already in the door. I recognized 3 of the younger girls and 2 of the older black girls, and 3 of the moms/dads, as new students at Amanda's dance studio. So now we knew exactly who we were competing against. I assumed that some of the other guys were going to a different dance studio? It was a good chance for us to size up our competition, but all of the other girls looked and acted so feminine, at least at first glance. All of the girls were in tight little outfits; tight tops, skirts, stockings, heels, the works. So we realized that mabye we weren't doing as well as we had thought.

We wanted to get started, so Matt had all of us take our seats. He told us that our challenge was that we would all go into a crowded bar/nightclub, and our goal would be go get as many guys' phone numbers as possible. The family trio that picked up the most numbers would be the winner and would get 100,000 bonus votes in the final vote. Our appetite was whetted.

Leticia, who had been at dance, was just stunning in a LBD and some sheer pantyhose. Being a nerdy and dorky guy in real life had helped him transition easily, since he already had a frail build and it was nothing for him to physically transform into a soft black girl. It was clear that he was doing awesome and he had a huge ability to be flirtatious and charm guys. I realized that he was my biggest threat. I was a black girl with big boobs but of course I was worried that I would do poorly in the competitions.

All of us girls entered the bar. It was full of guys ranging from age 12 to 30. The younger girls were supposed to target the teen guys and the dads/moms were supposed to play up the twenty year olds. I felt great, when not two minutes into the competition, I looked over and saw dad already with his hand on a guy wearing a suit. My brother started talking to a group of four guys, but I stood at the bar, kind of nervous. But suddenly, I heard a squeaky little voice say from behind me, "Hey sexy."

I spun around me and it was the dorky little guy from science class who couldn't keep his eyes off my boobs and tights. Even now, he was staring at my black pantyhose. But he was at least a phone number. Still, this was the kind of loser who'se head I would have stuck ina toilet at my old school. However, all of my male instinct was dormant and only Brandy was here. I flipped my hair back flirtatiously and said to him, "Hi yourself."

"I've always had a thing for black girls," he said to me somewhat forwardly.

"I've always had a thing for white guys," I replied. This was the first time I had ever flirted with a guy. I had had a couple girlfriends back at my old school but I had never dreamed that I would be standing here dressed as a girl and actually somewhat seriously flirting with a boy.

I got into a comfort zone and within an hour, I had picked up six numbers. But I thought that it probably wouldn't be enough. Dad had hung off the arm of the same guy for the whole hour and I wanted to go over and shake him and tell him to play the field and shake it for all the guys. But after the hour was over, Kendra saved the day and had gotten ELEVEN guys' numbers.

Matt tallied the votes and we won the competition. As a team, we had 18 numbers to Leticia's 16 numbers. So we were doing OK.

###########################

After another ballet practice that night, Fiona got us together for another feminine development lesson. We happly took our girlie spray and were really eager to soak up everything Fiona had to tell us about living as women. She was very pleased with how we did in the challenge and decided to give us a "special" lesson. As we typically did, we remained in our ballet outfits. I had put on my dad's Snow White leotard as i had wanted to do. Dad was back in his Little Mermaid leotard, and Kendra was in the polka dot leotard that I had worn earlier. Fiona was wearing only a sports bra and a pair of really tight black shorts.

"Tonight, I was going to begin with an introduction to cooking and sewing," said Kendra, "but, you girls have shown so much enthusiasm and skill in becoming women that I am going to begin to talk about sex. You girls will learn how to please a man and what you need to do to be good wives."

We were grateful that Fiona thought so much of us as girls to begin to talk about sex with us. I couldn't wait to learn the "birds and bees." I knew all about male puberty, but girls were a mystery to me. Us three black ladies sat there with wide eyes as Fiona began to tell us how to masturbate a boy.

"When you three were guys," said Fiona, "I know you all masturbated alot." We got big grins on our faces. "This is a serious subject girls," she said, "These are the things that a girl has to do to keep her man around, and you girls WILL become good at lovemaking."

"Wait," I said, "We are still genetic males. We are not supposed to become gay and like guys in THAT way." Then I realised just what a sissy little black girl I was in my leotard and white tights. Suddenly the thought of cuddling with a guy and giving him a hand-job didn't seem so bad.

"For the next six months, you all are female, and you will be attracted to men. Tonight, I will show you how to keep a man aroused with oral and digital sex and keep your men pleased. The hormones you are taking will change you into total boy-crazy babes." She described to us the female orgasm and how we as women had to use our hips and vaginal muscles in sex. We had to let the guy dominate us. She told us how we had to be coquettish with boys and "not give the game away" when we flirted, and we had to make let them make the first move or else we would come off as slutty. She went into detail about how to let the guy take charge during heavy petting but that we would probably have to help him unhook our bra straps.

Fiona reached into a black duffle bag and pulled out a few items for us to experiment with. She had a couple long black hot-dog shaped objects and a couple more that were attatched to wooden platforms. She explained to us that these were didlos and we woud use these to practice our technique. She let us check out some female conodoms and diaphragms and explained to us how we had to use these during sex to keep safe.

First the three of us guys practiced putting condoms on the dildos, which wasn't too difficult. It felt weird practicing stuff like this. I thought my little brother was a little young to be doing this kind of advanced stuff but I didn't want to question Fiona.

"All of the nerves and nerve endings are on the underside of the male penis," Fiona explained to us. "When you are pleasuring your man, you need to concentrate on stroking or licking the underside."

She had each of us grab a dildo and she first had us rib them agianst our white tights. Fiona showed us the right way to stroke and had us mimic. She explained to us how to nibble on the edges of the dildo to give our guys extra stimulation. We eagerly took mental notes, eating everything up. I couldn't really imagine having to do this stuff with an actual guy, and him treating me like a lady and opening doors for me.

It was so crazy watching my dad have to put the black dildo into his mouth. I wanted to stop him and slap him out of it. I realized that we had been brainwashed. I thought back to when my dad was working on his car or cutting the grass, and now he was doing all of this girly stuff.

With Fiona supervising, we got to play with the dildos for about an hour until Fiona told us that we had had quite enough fun. Fiona sat down with us and told us how, after the challenge was over, we would be taken to a secure location for our tans to wear off and we could readjust as males. We would get counseling that would help us return to our old lives.

######################

On Tuesday, dad came home from his job at Hooters. He looked really hot in his little orange shorts and pantyhose. He described to us how the guys were burning holes in the back of his shorts and one guy had even slapped his butt. We listened excitedly as he told us how he had plenty of practice with flirting and acting female, and by now, his voice was in a regular female registrar, so he had no trouble passing off perfectly as Monique Washington. He came home with 400$ dollars in tips plus his regular wage, which was twice what he had made working as a car salesman.

Earlier, I had snuck into dad's room and tried on one of his Hooter's outfits. I pretended like I was one of the sexy girls there serving chicken wings and beer to horny guys. I wished that I was 18 so I could do that and make lots of money.

I was busily perusing my copies of "Cosmo", "Dance", "Ebony", and "Black Woman". Dad was glad to see that I had been quick and eager to learn about being female. I know it hurt him to see the pride of his loins looking and acting like a luscious African princess but it was just our lot in life.

Before ballet class, Fiona called a family meeting and told us that on Friday evening we would be attending a debutante ball and the three of us would wear fancy gowns and introduce ourselves to society. It was up to us if we would bring male dates or not.

I had gone back up to my room and had stripped down to my bra and panties and was ready to put on my tights and my little brother came in and asked me if he could look through my leotards for one he might like to wear. After 10 days, his voice was that of a real black girl and I found that I wasn't having to try anymore to sound feminine. I told my little bro to go and pick one out he liked and I would help him dress and do his hair. I had decided to wear a baby pink leotard with an attached short skirt. I had just pulled on my tights when I heard a knock at the door. It was dad.

I was holding my leotard in my hands when dad came in dressed in his dance outfit, a yellow tank leotard and white tights. He said to me, "Do you girls need any help dressing."

"No mommy," I'm fine, I said to him.

"Is everything all right," he asked me. "Its just that Fiona has kept me so busy with cooking and cleaning and laundry that I haven't really had a chance to see how you girls are handling these changes." As he was talking to me I pulled on my leotard.

"Well daddy," I said, "I'm coping just fine, but this is just so odd."

"Its the 21st century," said dad, "We guys have to learn to accept a female role."

"Its not that," I said and I started to cry, "Its about me. I don't know if i want to be a girl."

My brother had pulled on a pink and white leotard he had found and was coming over. Instinctively, like a girl, he saw that I was upset and gave me a hug. I hugged him back and dad put his arms around the both of us.

"Its just that I don't think I can go back to being a white boy, not after all this."

"The counselors will help us adjust," said dad. "Once we get out of here and take off our tights and get back into boxer shorts, We'll forget all of this ever happened. But for now, we are black girls full-time. Its just like playing a part in a movie." Dad kissed me on my forehead.

I felt a little better. As long as I kept my eyes on the prize I would be fine. For now, I just had to cope. My dad took my hand and led me into my closet to see which gown I might want to wear. I had my eyes on a purple prom gown with sequins. My dad said I would probably have to wear some sheer tights under it.

Soon, Fiona knocked on our door and told us that we were going to be late for class so we grabbed our dance bags with our spare tights and hustled off to the minivan.

All of the other black girls finally seemed to feel more secure at ballet class and really began to open up. The girls/guys looked so adorable in their dance clothes. Leticia, Keisha, and Chondra were the three older black girls and Trisha and Tiffany were the two younger black girls who had been boys so recently. Trisha and Tiffany, with Kendra, made such a cute trio in the little girls class. Kendra had paired up with Trisha to master the song and dance routine and so recently these girls had been playing Pee-Wee baseball. It was cute watching Amanda move their bodies.

So myself and Krystal had really started to mix with the older boys/girls and we found we had alot in common. Thier coaches were really tough on them to learn how to be girls and they had all been put in baby girl dresses and had to play with dolls, like I had. Soon, at least, we would progress to being "big girls," and we could at least have some respect. We all had to work on crossing our legs and smoothing our skirts and keeping or modesty. In the back of our heads was the thought that soon we would be on stage in tutus dancing sleeping beauty and soon we would be modeling bikinis in a pagent. But all of us were far too busy with dancing and learning how to be girls to even think about being boys. I had still made some inroads introducing myself to some of the white girls in ballet class, but I soon found out that they all had boyfriends already.

I had made arrangements earlier to go and hang out at Krystal's house after ballet. Krystal's parents came to pick her up and I got in their car and we drove to their house. I let Krystal play with my hair and she spent some time putting some barettes into my massive "do." We put on some soul music and we chatted about cheerleading, dance, and some of the hot guys at school.

We spent the rest of the afternoon playing dress-up. I took of my pink leotard and white tights and I slipped into a little black dress with sheer pantyhose that Krystal had. We spent a couple hours posing in the mirror in various outfits of hers. I tried on a velvet green dress of hers with black tights, and then I think I tried on every leotard, panty, bra, and bikini she had. As a boy, it felt erotic getting to put on tights worn by an actual girl that I knew had caressed Krystal's legs just today at dance. We put on our cheer outfits and rehearsed our moves. This was much more fun than throwing a ball back and forth. Sadly, such a fun night had to come to an end and I had to go home and do homework. Fiona gave me a petticure and gave our family a brief talk about the virtues of domestic womanhood. She gave us each a book to read, "The Domestic Goddess." and she told us that we had to live to that ideal.

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The day after, Fiona took us to the mall to pick out some more clothes and outfits we might like to wear.

Dad found a dress that was like the one Michelle Obama wore on election night and he said that he couldn't wait to wear it at the debutante mall. He had been obsessed with Michelle Obama recently and he he had been telling us how she was his hero. This from a guy who had been a loyal Republican his whole life!

Dad and I had to go use the girls room and we went into use the bathroom. I went in the stall and pulled down my tights and panties and sat down, even though I only had to go pee. After me and my dad were done, we both went to the mirror to "freshen up" We touched up our makeupa and lipstick and we made sure our hair was still perfect. We were really enjoying this mother/daughter bonding, both of us in skirts and hose, out shopping for makeup and dresses. My dad made a point to reassure me how pretty I looked, and I couldn't have been happier.

That night we spent a couple hours playing "House", with Fiona playing the role of dad with Monique as the doting housewife and mother.

TO BE Continued

The Challenge Part 004

Author: 

  • TylerD

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

The girls/guys go to an African hair braiding parlor and compete in their first Challenge.
 

The Challenge: Part 4

By Tyler


 

Dad picked me up from school wearing a velvet plush sweat suit that was really tight and showed off all of his developing curves. His butt looked so sexy and he was just my gorgeous black momma. He was wearing sheer pantyhose under his sweat pants. Dad told me that Fiona had some plans for us this afternoon so we were going home to meet up with her. I sat in the car, smoothing my plaid skirt over my white tights, eagerly anticipating what she could have in store for us. We had had so many neat surprises on our journey towards becoming black women.

My little brother ran out of the door carrying his bookbag and purse. He was adorable in his jumper and his skirt was swishing as he was skipping down the sidewalk with two white girls. If we had to be girls, at least we got to be popular girls.

When we got home I took off my schoolgirl uniform and left on nothing but my pink lingerie and my white tights. I grabbed black top that had the words HOTTIE spelled out across the bust in rhinestones and pulled it on. I opted for a very short denim mini-skirt that showed off every inch of my sexy legs in their ivory hose. I put on a pair of dress sandels with spiked heels. The heels made me walk with danity steps and they pushed up my butt and made my figure look even more feminine. Fiona came in to check on my outfit and my makeup and she decreed me fit to go to our surprise. She looked cute in a tight green dress and orange pantyhose. She was like a second mom to me and I was coming to love her. I really liked her sense of style and I was sad that soon I would have to go back to being a white boy and surrender my long, nappy hair, tights, bras, tits, and my pretty outfits. She made sure to smooth out my tights because I had a couple wrinkles in my hose.

Despite the fact that I was for all intents and purposes a fully functioning black girl, I still had my old "urges" of when I was a guy. I would pretty much have to wait to masturbate until Fiona was done training us for the night. But I found myself fantasizing about dancing the Nutcracker on stage in my pretty pink tights and tutu, being held in the arms of my strong male partner during the pas de deux. All of this training was having an effect on me. I would think of how good and comforting my little tights and leotards were as I pretended to be as girly as possible at dance class, and then, I would climax.

My brother had changed into a similar velvet tracksuit like my dad was still wearing, except his was red and he was wearing some regular pantyhose underneath. We all grabbed our purses and headed out to drive to our unknown destination.

We drove for about 20 minutes to a part of the town we hadn't been to previously. This area looked a little more run down and "ghetto" than or manicured suburban area where we had been staying at. We drove a few blocks down the main road and pulled into a dirty strip mall. We parked up next to a small store, and this store had a sign out front that said, "AABC hair braiding." So we knew we were in for an afternoon of beauty. Pictures of black women with complicated do's festooned the windows.

As guys, we were a little nervous but excited at the same time of continued experiments on our looks. We saw a row of salon chairs and there were a few black women in there ready to style some hair. My dad's hair was long enough now to try a new style and I was wondering what they were going to do to me. There were pictures of black women everywhere inside the beauty shop, just to remind us and give us ideas for what kind of hairdo we might like. There were racks of beauty products everywhere. Rap music blared from the radio. It was a strange new world.

One of the black women walked up to me and introduced herself to me as Kimmy. "You look really cute," she said to me. I didn't know if she knew that I was really a white boy. She told me to go into the bathroom and remove my tights so she could paint my toenails. The other two women were going to be individual stylists for my dad and brother. We were kind of shy and said little but deep down we knew we wanted to take this next step on the road to womanhood.

So we all went through the process of shedding our hose, letting us get our nails painted, getting our legs waxed, and putting our tights back on. When we came back out, the salon girls gave us all botox injections in our foreheads, and now our ebony skin was shiny and free of wrinkles. Then, they shot a mysterious substance into our upper and lower lips, so now we had nice, full, pouty, big lips like black girls are supposed to have. The structure of our faces was now that of black women instead of white guys. We wondered if we could ever go back. Kimmy explained to me that after we were done on the show that they could drain the collagen if we so wanted(so she knew that we were guys.)

Us guys were then told to sit down in chairs and we had our ears pierced. We all had big hoop earrings put into our ears. The ladies explained to us how we had to keep a stud in all the time or else the holes would seal up. But we were all happy to have piercings and our earrings helped to develop our black-girl personality and give us some flair. Dad couldn't get over how his lips and ears looked. We all found ourselves humming along to the beat of the rap music as we were being worked on.

The three of us sat in salon chairs and the stylists vigorously went to work on us. They trimmed my eyebrows and put some makeup on me. They decided to straighten out my hair and give me some highlights, and Kimmy put some strange creams on my scalp and used hot irons to straighten out my mahogany locks. I just sat there and watched myself get prettier and prettier, and I realized that I looked like a cross between Beyonce and Tyra Banks, but with much darker skin. I was a little chocolate hotcha. I imagined myself as a stripper in lingerie and hold-ups giving lap dances to college guys. My dad was having his now longer hair brushed out into a short, boyish, but very sexy pageboy style, and I couldn't get over how he resembled Michelle Obama. I knew it wouldn't be long before he was the arm candy of a basketball player. Fiona observed with approval as us white guys, who once wouldn't have given her a second thought, were being transformed into totally demure and kittenish black ladies in our pretty tights. She doted on Kendra, who was having some work done on his complexion and bangs, and his hair seemed much fuller and less stringy than it had been. These hair products they were using gave "body" to our new hairdos.

"I think it is so great, getting to doll up a guy," said Kimmy, "You boys just make totally convincing women. I hope you guys decide to stay as black women instead of changing back to white guys. I can tell that you three were just made to be feminine. It would be a shame to lose three such pretty women."

Kimmy was just finishing up with my hairstyle, and I thought that it was wonderful. The blonde highlights were a kick ass finishing touch. As new women with pierced ears, big lips, and other new developments, our little family got into the minivan and drove to get some dinner.

We decided to go to Chili's and we went in and took our seats. A group of 30-something businessmen could do nothing but ogle dad, and a group of teenage white boys couldn't keep their eyes off my tights. They were totally more tolerant about the whole interracial thing in New England than they had been in Tennessee. Even though we were hungry and wanted burgers and fries, we had to order salads and sparkling water so we could keep our figures. This was one of the few times so far we had really been out in public around real women and we spent alot of time checking out their outfits and comparing ourselves to them. But we weren't thinking about all the girls in there or our waitress in a sexual way.

Fiona had us practicing our table manners and promised us severe trouble if we didn't put our napkins in our laps, keep our legs crossed, or chew with our mouths closed and take small bites. It was totally turned upside down from when we used to order mountains of fried foods and shove it in our mouths with no decorum. What we were doing was enjoying ourselves as Monique, Brandy, and Kendra, the Washington family.

We had an ettiquite lesson after dinner and we drove to the home of an old lady, Mrs. Miller. Mrs. Miller had been informed of our "situation" in advance. Mrs. Miller commented to us on how beautiful we looked and what a good job we had done becoming women, as judged by our before and after photos.

We practiced walking in high heels with a book on our head and basic balance exercises. We learned the right way to wave, elbow/elbow/wrist/wrist/. She explained to us how to be dainty and feminine in all of our body movements, and we had to practice being graceful when we stood up and sat down. Then, Mrs. Miller told us that at parties, we had to be good hostesses and confine our conversation to cooking, fashion, and other domestic issues. Things like politics, sports, and business were men's issues and we had no business bringing them up, if we were ever going to be proper ladies. It was a lot to take in, but it was incredible how much we had managed to learn in just two weeks. Mrs. Miller showed us the proper way to manage sitting in a short skirt, like I was wearing.

Fiona gave us the night off from any lessons, so myself and Kendra went into dad's room and he let us try on some of his clothes. My brother and I put on a few of his big girl dresses, and dad was having fun getting to help develop his teenage daughters. We still couldn't get over our new styles. I was amazed at the eclectic selection of outfits that dad was allocated by the show. He had all sorts of colorful patterened dresses and I fell in love with a white dress with green flowers and posed in the mirror for the longest time, still wearing my tights underneath. Then, I got to put on dad's blue ballerina tutu with the massive starched pinifore and dad helped me lace up the back. We stayed up well until 11PM just making light girl talk. I described to him how my first cheer practice had gone and how we all had to wear tights under our little cheer briefs. He sat there listening to me like I was telling him the location of the fountain of youth when I described all the preppy girls, of which I was one, doing our little routine in our costumes. He said he couldn't wait to see our first performance.

Kendra and I showed our dad all of our black Barbie and Bratz dolls and we told them what we had named them and gave them their story narratives "Desperate Housewives" style. We let dad brush their hair with us. Previously, we listened to country music, but now we had some deep soul on the radio.

We all put on pink nighties and fell asleep in dad's bed, cradled in his arms. We turned the TV on the Lifetime channel as we drifted off to sleep and watched a presentation of "How Stella Got her Groove Back." We fell asleep with dreams of going out clubbing dressed as black women, grinding sexily on all the guys at the club and being taken home by some young stud to be pleasured.

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On Thursday morning before school, I decided to dress up like I was allowed to and I chose a black/white/gray checkerboard pattern dress with short sleeves and a skirt that ended just below my crotch. As I was dressing, I found myself humming bars of rap music. I put on white tights underneath and I was wearing a blue bra and panty set underneath. I put on a pair of black heels I had. I chose a gold necklace, some bracelets, and a few rings that were in my jewelry box and put them on. I wanted to look as sexy as possible and this was my first chance to really show off my new style. Dad and Fiona came in to check on me before I went off to school. Dad was already in his Hooters uniform for another day. I could tell by the look on his face that he disapproved of his daughter showing so much leg but Fiona told him that it was OK. "All the girls wear tight short skirts nowadays," she reassured him. In any case, I don't see how he could really say anything being in orange hot pants and pantyhose going off to serve cocktails.

I wanted to put my long hair into a ponytail but Fiona told me that I was hotter with my hair down. My brother came out of his room in a blue sailor dress with white tights and he was so enthused to go and see what all of his girlfriends were wearing on "free dress day." I thought to myself that it was going to be nice to "scrub" to school tomorrow and just get to relax in a T-Shirt and sweats for a change.

Krystal thought I was really cute at school and she was wearing a purple top with a long pink skirt and ankle socks. She reminded me that we had a Future Homemakers of America right after school, and then her parents would give me a ride to ballet. Fiona had been thoughtful enough to put a leotard, spare pair of tights, and my ballet slippers for me in my pink book bag.

At 2:30 PM we went up to Ms. Widmore's room where our FHA meeting was to take place. Ms. Widmore was the home ed. teacher. From the classroom window I could look out and see the guys getting ready for football practice and I thought to myself how I should have been out there smashing muscles instead of in here talking about what giving birth was going to be like. Here I was in my little dress with barettes in my long hair and wearing white nylons. Nine other girls sat around in a circle and we talked about cooking, sewing, makeup tips, and everything we would need to know when we were dutifully married, faithful housewives. My little brother was in his part of the school, no doubt in a little Junior Miss class getting his feet wet as a black woman.

Ms. Widmore asked me how I felt about a woman's right to choose and I said that it was my duty as a woman to give my husband as many kids as he wanted. The other girls in the group agreed with me; so much for feminism. I told the group how I couldn't wait to be a mother to a bunch of little ducklings. I imagined myself working in the kitchen wearing a pencil skirt and an apron as my man came home from the office, and I would have his dinner ready for him and I would iron his clothes as he went out to the bar with his buddies. Then, he would come home and I would satisfy his sexual needs but I would go unfulfilled.

I was confusing myself and I knew that this dualism couldn't really be me. Part of me was the guy who dreamed of becoming a high-powered attorney, but now I began to contemplate a different future for myself as a glorified domestic housewife. I decided that I would just let the next couple years play out and I would see which direction I wanted to take. If I decided I wasn't happy as a guy when I got back out into the real world, I would again become a woman(a white woman this time.) Women have it easier anyway. Guys have the responsibility to ask girls out and women get all the benefits of Affirmative Action. For now, I was just going to leave everything up in the air and see how I felt after the pagent.

I had been contemplating my future in a way that I had never before done in my life. This choice was going to be tougher than I had anticipated when I was first made over into Brandy. Krystal's parents picked up my brother and I and gave us a ride to the ballet studio. They dropped us off and the three of us black girls went into the bathroom to change. I shed my dress and pulled on the orange leotard with an attached skirt that Fiona had packed for me. I took off my high heels and tied on my pointe shoes. Kendra put on a red, longsleeved leotard with ribbing, and Krystal pulled on a pair of white tights an a pink leotard. It was utterly fascinating for a new girl like me to watch a real girl like Krystal put on her tights with such professionalism. She was so attractive and I was getting to watch her change. But she had no clue that I was really a guy and that I kind of wanted to date her. The three of us sat in a small circle and we all put our hair up into buns to keep our locks off of our shoulders and faces. We were just pretty girls helping eachother get ready. The three of us were soon in our slippers and we headed out to join the rest of the girls.

Zafira had come in wearing a baby blue leotard with ivory tights, and she excitedly waved me over. I noticed when I ran or walked fast, I sort of skipped and moved bouncingly. But she just looked so adorable, and I was ready to make a move and asked her out, but I realized that I couldn't because I was in Brandy mode. All I said was, "Hiya Girlfriend," in my best Brandy voice.

Amanda had called all the girls together into a group circle. She had a bunch of big cardboard boxes and she told us excitedly that our uniforms for our performance of "Sleeping Beauty" had arrived. I would be considered one of the younger girls and be a lilac-fairy. I was a little disappointed that I would not get to try out for a more prominent part, but I really had no chance because between both studios in town there were girls that had been dancing for 15 years. I would still get a small solo and get to partner with a guy dancer, so all was not so bad. I was looking forward to impressing my dad with how feminine I could be in a tutu during a ballet performance. Also, I could dance next to Zafira.

Amanda said, "In case an older can't participate, one of the younger girls could get a chance to audition for a lead role." So I had hope. I wanted my father to see me make my total transformation to a gorgeous black ballerina. My dad would get to dance a minor part in the ballet as well, but it would be a bit part and he would just get to watch most of the show. His time to shine as Monique would be at the pagent.

So Amanda opened the boxes and had all the girls form a line. I was first in line and she handed me a white leotard with long sleeves, and then she pulled a giant fluffy ring out and I knew that it was the tutu I was at least going to wear. She also gave me a package of three pairs of white tights. Each one of us was given a plasic tiara to wear. I was really excited about the costume and I couldn't wait to try it on. I was so going to model it for dad and if he was lucky he would get to wear it around the house; if he asked nicely of course!

When all of us girls were issued our costumes, Amanda instructed us to go back into the ladies' room and put them on so we could come back out and rehearse the steps for Sleeping Beauty. Excitedly, us girls rushed 'en masse' and began to change. I quickly dropped my orange leotard and pulled on the white one. I noticed that my tutu had a lacy panty bottom so I figured I just had to step into it like a pair of shorts. I put in both feet and pulled it up over my crotch and made sure the elastic waistband was tight around my waist. The tutu was about 1 inch thick of lace and stuck out straight for two feet in any direction and was about six feet in circumference. I glanced in the mirror and noticed just how sexy it made my legs look in white tights.

Zafira, the good little dancer she was, was having no trouble changing, but I got to catch a brief glimpse of her small budding breasts as she was pulling on her new white leotard. I got to see her bra and the tops of her tights and the cute little white panties she was wearing. It was nice to feel like a guy for a little bit again and check out girls. I got to look around the bathroom and observe the girls and boys/girls in various stages of dressing.

Kendra was making it look easy pulling on his tutu and Krystal was already helping a younger black girl who was struggling getting her leotard back on. Krystal helped her pull on her tutu. Leticia and Chondra were already in lilac fairy mode. We all put our tiara's on our heads and flashed big smiles. I was primping myself and putting some touches on my makeup. I was making sure that my tights were straight when I looked over and saw Tiffany in the corner still struggling putting her leotard on over her tights. Tiffany was only 12 and she was the littlest boy/girl in the competition. I didn't really want to help out a competitor, but I felt so bad for her and I went over and gently helped guide the leotard up over her purple bra and I helped her get her arms in the sleeves.

Tiffany started crying to me. "I'm just struggling so much with all this. These outfits are so hard to dress myself in. I hate wearing tights and dancing and being girly. Last night I had to wear an empathy suit and pretend I was pregnant. I miss being a guy and running around the neighborhood. I wasn't meant for this and I can't do this."

"There there Tiff," I consoled her as I guided her feet into the legs of her tutu, "All of us are having a hard time. None of us really want to be here wearing panties and being princesses. We're all still boys deep down. They can change our outside appearence but deep down we are all still men. It is what is on the inside that counts. For now, lets just enjoy dancing."

Tiffany seemed somewhat happier as I helped get her tutu on straight. She told me how much fun at least her dad was having doing all of this stuff. He had been given a job as a cocktail waitress at an upscale bar and he was just loving doing all of this crossrdressing. Tiffany said that her dad had been a secret crossdresser before all of this and was just thrilled to death to be here and that this was the absolute greatest thing that had ever happened to him. Tiffany was sure that her dad would never go back to being Jim and would be Jennilee for the rest of his life.

Tiffany's brother Chondra, formerly Charlie, had actually been a tap dancer as a guy, so I knew it wasn't just my eyes fooling me when I saw how good he was at some dance steps. I put the Tiara in Tiffany's frizzy hair and we skipped out of the bathroom and back out to rehearsal.

So here we were, 20 girls in tutus and tights. Amanda had us go through some warmups, but I was surprised at just how simple the backup roles for Sleeping Beauty really were. Most of it was just standing around and posing and looking pretty, like background decor. However, I would definitely take my chance if I had an opportunity to audition for a more prominent part. I would get to dance with a hot guy, but more importantly, I would get more camera exposure and the home audiences would see me dancing the lead female role in a ballet. The name and face recognition would surely garner points for Brandy Washington!

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Kendra and I wore our Tutus in the car all of the way home. I forcasted myself, once my tan wore off and I was back home, getting made over into a blonde white woman named Melissa. I would keep taking hormones but I would let my skin and hair revert back to their natural fair color. By that time, I would have grown full breasts of my own and I would still have the legs of Brandy Washington. I would be a southern belle and I would go to balls and such things that my sister did when she was a debutante.

I would go to ballet class as Melissa Thompson and wear all of my pretty outfits. I would audition for a school like Juliard and eventually, hopefully, become a prima ballerina. Melissa Thompson would headline as Giselle with her Lesbian parents Melanie and Joanna and her sisters Julie and Kelly watching her dance ever so gracefully. But I would have to work my way through school and I would get a job at Hooters wearing the sexy shorts! Either this or I would go back to being Mike and pursue athletic scholarships. My future looked so bright no matter which way I went.

Melissa would have radiant long blond hair and would be the image of feminity. I would miss being a black girl named Brandy, and I kind of wondered to myself if I could just remain as Brandy for the rest of my life. My choices were so tough.

I almost wasn't listening as dad described the black tutu/dress he had been issued for the ballet. His tutu was the exact same style as ours, except it was pitch black and he had been given a black leotard and a tiara to wear. I just saw two black bunheads in the front seat. Kendra was going on and on about how good of a dancer that they both were going to be but I was just lost in thought in the back seat, kicking my tighted legs in the air and fluffing my bunched tutu about my waist. I could tell that Kendra was just loving this whole experience and I was wondering if my little brother Kevin was gone forever. I noticed my black, made-up face in the rear view mirror and wondered if that would be me for the rest of my life. It was totally surreal.

The three of us walked in the floor looking like little flowers. Fiona was delighted to see us, and she had our empathy suits ready for us. We grabbed a quick snack and then joined Fiona in Dad's bedroom. Three leotards with bellies awaited us on the bed. We were all still in our tutus, just looking as girly as could be.

Fiona first described to us how females masturbate by stimulating their labias by hand or with a didlo. Since we did not have vaginas, we couldn't practice but she just wanted us to be aware of how we were supposed to please ourselves as women. We had to fantasize about our outfits and the men in our lives. It was unfortunate that we still retained our hidden penises under all of our feminine finery and the show did not have the authority to give us an actual sex change so we could go "all the way." She gave each of us our own personal big black didlo and told us to practice sucking on them or stroking ourselves with them in our own free time. If we were bold enough, we could stick them up our heinies and experience anal sex. As women, especially ones without vaginal cavities, we would probalby have to allow our male partners to make whoopie in our butts. Since we couldn't be penetrated from the front, we had to be entered from behind. It was our duties to be the penetratee, and not the penetrator, even though we still retained our manhood. We were learning so much more than we ever had learned in sex ed. or health class. I would have killed for this kind of information as a boy. I would be so good with girls my age when I would again be a male. I would know exactly how to please them and bring them to orgasm, because I would have had the practice on myself.

"Strip off your tights and leotards and grab an empathy suit," ordered Fiona. The suits were that of women's abdomens about 8 months pregnant. They were pretty much dark brown nylon leotards except for a big heavy bulge in the middle. I realized that even if I became a full time woman, that I could never have kids of my own, so I would have to adopt. Still, I would see just what my mother went through to create me and I would appreciate her much more when I went back.

We took off our tights, bras, and panties and each of us grabbed a suit. The biggest one was obviously for dad. I put both legs into the holes and pulled the heavy garment up over my tits. I put my arms through the spaghetti shoulder straps. The empathy suit was the same shade as my skin and I looked in the mirror and saw a naked, pregnant, black female wearing a tiara.

Dad got up his empathy suit and then helped his son Kendra get his on all the way. This was even weirder than our dildo training but it was absolutely fascinating in a way. We were men in uncharted territory; pregnant black women.

"Put all of your dance clothes back on," Fiona ordered firmly. I stepped back into my bra and panties and then I pulled my tights back up to my fat waist. My suit was weighing me down and must have weighed 20 pounds. This was going to be tough. Fortunately for us, our leotards were stretchy enough to fit over our pregnant belles and soon we were back in full sleeping beauty costume. We were now three pregnant ebony ballerinas. It was so weird seeing my dad and brother looking like this. We stared at eachother in absolute amazement.

"For the next two weeks," said Fiona, "You three will have to wear your empathy suit whenever you are inside the house, You will get to take it off when you go outside for any activity, but you girls will feel what women have to go through to give birth."

It was going to be hard to sleep now, and I had lost my sexy figure for the next few days so I wouldn't really be able to model any of my clothes on my own time. We had all been so busy the last couple of weeks that we barely had any time to think or reflect. My dad was now my mom and my brother was my sister. But we just had to drive forwards and do whatever was asked of us so we could win the money. We filed off to our rooms to get ready for bed and another day of feminine fun. Fiona reminded us that we had our next "challenge" coming up this weekend, as well as our debutante ball on Saturday night!!!!!!

TO BE CONTINUED........................

The Challenge Part 005

Author: 

  • TylerD

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

I had dropped the girls off at school and now I had to come back home and take care of my domestic chores. Fiona had ordered me back into my empathy suit and a maid's uniform for doing chores around the house, I pulled on a pair of black tights for convenience and threw on my maid's dress. I wished I didn't have to wear high heels for cooking and cleaning but it was her rules. It was a little irritating how she would lounge on the couch and watch golf while I would go at the furniture with a feather duster.
 

The Challenge: Part 5

By Tyler


 
I had dropped the girls off at school and now I had to come back home and take care of my domestic chores. Fiona had ordered me back into my empathy suit and a maid's uniform for doing chores around the house, I pulled on a pair of black tights for convenience and threw on my maid's dress. I wished I didn't have to wear high heels for cooking and cleaning but it was her rules. It was a little irritating how she would lounge on the couch and watch golf while I would go at the furniture with a feather duster.

I had to get all my duties completed by noon so I could change into my Hooters uniform and head off to work. I had been up since 5AM preparing breakfast and helping to get the girls off for school. I had to remember to always smile and never let anything get to my head. This whole time, I hadn't had much of a chance to talk to my girls and really see how they were dealing with this change. Sometimes it seemed like they couldn't be more enthusiastic about being women and other times my former sons were quiet and sullen and it was hard to gauge their emotions. I was worried that the boys would lose their respect for me seeing me feminized and cuckolded by Fiona. Fiona had even given me a new driver's license that read: Monique Washington, Female, 37 years, ethnicity: African-American.

I had finally finished doing the dishes. Fiona was satisfied that I had completed my domesitc chores and I was ordered up to change into my little costume. My butt swayed back and forth as I went up the steps and I could tell the hormones were really doing their business on me. I pulled down my tights and threw them into the hamper. It felt good to finally be able to ditch my maid's uniform and my empathy suit.

We had to wear pantyhose at Hooters for sanitary reasons, and so our bare legs wouldn't be scalded by hot grease. I opened up a fresh pack of sheer pantyhose and stretched them out like Fiona had showed me how to do before I pulled them on my legs. I wiggled my tights all the way up and then I put on my white bra. We weren't supposed to wear panties or even a thong underneath because our pantylines would show through the shorts. I slipped into my Hooters tank top and finally put on the orange shorts. The uniform was quite form fitting and the guys had been giving me generous tips for my first few days as a waitress. I sat down on the edge of the bed and put on my socks and sneakers. Fiona allowed me to wear sweatpants over my shorts on my way to work just because Hooters girls weren't supposed to wear the shorts outside of the restaurant.

Mandy, the head Hooters girl, had taken me under her wing and had given me some "tips" on how to keep the male's attention. I always had to bend over from the waist to pick up something off the floor and never squat; that way the male patrons could see the full moon of my butt. I had already had my butt slapped twice in the last three days and the guys who went in there to eat were quite friendly and wanted to flirt. I was getting alot of practice at being coquettish and my daughters would hound me with questions about work. They would want to know about how I was interacting with the customers there and what exactly I was doing. It was restaurant policy that a waitress would be fired if she actually started to date a customer. I couldn't cheat on my wife with another man anyway.

I had to work a 5 hour shift for five days a week. I was only kind of embarassed when we had to go over and sing the birthday song and twirl hula hoops and shake our butts. We had to sing these stupid little songs on occasion and clap our hands. If my guy friends could have seen me shaking my booty like Beyonce! But it felt really good to pick up a ten dollar bill as a tip from every table I waited on, and I was just raking in spending money.

Before I knew it my shift would be over and I was back in the Minivan; driving to the high-school to pick up my daughters. They would tell me about their day and soon we would be home and getting ready for either a ballet or an ettiquite class. .It was bizarre seeing two black girls in little schoolgirl outfits or cheerleading uniforms come out of the school and realizing that they were my progeny. I barely even felt like a man anymore, and being an actual father felt like a distant memory. It did give me a deep perspective on what my wife had been going through for the last 17 years.

Fiona came into my bedroom to help get me changed for dance; she was wearing a basic black leotard with pink tights. I typically liked to dress conservatively for ballet but she had for me a leopard print leotard with long sleeves and an attached short skirt with ruffles, and I was supposed to wear white tights underneath. She pulled my sheer hose that I had worn for work off of me and had me sit on the side of the bed. She had me put my feet in both legholes of the tights and she rolled them up to my knees. I did really enjoy being assisted at dressing myself by a totally hot lady like Fiona. I really took no offense because I was so new at being a woman and I was really like her little daughter who she had to teach with love. I wanted to be a woman like her and have sexual confidence and empowerment. For now, it was girlie see, girlie do.

"Stand up," she ordered. I did so immediately, and she pulled the tights up my ebony legs and made sure that they were on smoothly. She took the leotard and had me step into the garment. Soon, I was looking really cute in my leopard print leotard, a color and pattern that made an interesting contrast with my white tights. I liked how she had been gentle with me and helped me ease into my female role. She was really treating me like I was her little sister. I posed in the mirror with her for a few minutes and I wished I could keep this outfit on for the rest of my life. I felt like a six year old black girl. I was a hot female leopardess, and I felt like Cleopatra. I shook my wild ass in the mirror and I loved how my cute big butt looked. Two weeks into the challenge, I had totally awesome curves like train tracks. She told me to put on my tennis shoes and get my dance bag together while she helped my sons get changed.

It was a crazy role-reversal situation to be sure. It felt great to be totally encased in nylon and be a total boy-magnet. The only genetic female in the house was the one totally in charge. We knew if we crossed her we would be in big trouble. But Fi was usually nothing but sweetness and love.

Kendra came out wearing a tiger-striped leotard and white tights, and Brandy was also wearing a leopard print leotard, but a silver and white variaton from mine, and her leotard also had the attached skirt. Brandy was wearing white tights underneath, and I noticed just how prominent and full her breasts were becoming, much more so than last week. The three of us made the sweetest mother/daughters tableau. We all looked so smooth in our matching feline dance outfits. Fiona told the three of us to grab our purses and dance bags and get in the minivan.

I would have felt ridiculous wearing so feminine an outfit at a dance class back home, but all the other dads were being forced by their coaches to wear equally embarassing leotards, so I didn't really feel alone. Tamika, formerly Jay, for example, was stuck in a pink leotard spangled with white stars and he was wearing white tights. Bufanda, formerly Barry, was wearing an interesting combination of yellow tights and a purple leotard. So we were all in this together. There was strength in numbers.

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Since it was Friday night, Fiona decreed that we could finally have a night just to relax. I kept on my ballet outfit and went up to my room to pop in a DVD of season one of Desperate Housewives. I crawled into my bed when Brandy came in my room, still wearing her dance outfit. We looked like a mommy leopard and her baby girl. Brandy was clutching one of her black barbie dolls and I invited her up on the bed to cuddle with me and watch TV. She happily crawled into my arms and I stroked her pretty straight hair. We unintentionally rubbed our tights together.

"Mom," said Brandy, "I've been thinking alot about our futures."

"Really," I said with surprise, "What is on your mind?"

"Well," she said, "I was thinking mabye I don't want to go back to being Mike."

"You want to keep living as Brandy after this is over," I replied.

"I might want to stay as a girl," she said, "but I would change to a white girl. It would seem more natural. I would be Melissa and I would be a ballerina."

"I was totally unaware you liked being a girl so much," I said with shock, "I just thought you were going through the motions."

"I was at first, but now I am really starting to like this new lifestyle."

"Does your brother feel this way too," I inquired, "He seems like he is adapting way better towards being female than either of us."

"I can't really tell with Kendra. I think she is so young she is just going to do whatever she sees her role models do. If she sees us being black women she'll jump in head first. But it seems like she is all about barbies and Ballet now and Kevin is gone."

"So what about you," I asked, "How are you feeling?"

"Well," said Brandy, "I feel torn all the time. Half of the time I feel like I am a guy and this whole thing is ridiculous. But other times I just love getting to be cute and sexy. I like getting to have my hair and makeup done and wear pretty dresses. Being a girl, you get to wear different things everyday besides pants. And I think I actually like things like ballet more than my old sports. Even if I go back as a guy, I'm still going to take ballet."

"But there is a chance that you will go back as a black girl or a white girl," I asked him?

"Fiona said that our tans would take time to wear off. I might stay as Brandy for some time. But I think if I become a white girl I will become Melissa Thompson. Or, I might just go back and forth between Mike and Melissa."

"Well," I replied, "You have to choose one or the other. Just remember that you have nothing but time to think about it. I will support you wether you become Brandy, Mike, or Melissa."

Brandy said to me, "I've just been having these fantasies of being a pretty ballerina dancing on a stage with a male partner. I want to go back to my old school as a popular, preppy cheerleader and show them how devilishly hot I am. Being Melissa, I can keep my female side."

"So let me ask you," I said, "Have you started to like boys, or do you still like girls?"

"Well," said Brandy, "I found a guy date to take me to the debutante ball tomorrow night. Kendra found a boy too. We've just been too busy to bring it up. Zack is coming buy in his car tomorrow night to pick us up."

"Oh precious that is so wonderful," I said as I gave her a big hug. I smelled the perfume in her hair.

"So Mom," said Brandy, "Is it a sure thing that you are going back to being Joe? I only ask because you looked like you were having so much fun when we were wearing our princess leotards and learning about sex. I would just hate to see you go back to the way things were without any changes."

"So you didn't like the way things used to be sweetie?"

"You were always working as Joe," said Brandy, "If you were a woman you would be home more and we could bond together and have girly talks like we are doing now. Besides, it is obvious that you like parts of being a lady and I would just hate to see your feminine side taken away from you. I saw how happy you were wearing your Ariel leotard, and its hard to believe that you are the same guy who liked to hunt and fish. There is definitely another viable side to your personality than Joe, the tough insensitive father. Cinderella the princess needs to come out of dad."

"Mabye we could just play dress-up on the weekends when no one is around," I said to my daughter.

"I just want to have the same close and loving relationship that we have right now," said Brandy. "If it means we have to keep being girls, than so be it. I just can't see us staying close if we go back to being guys, even if we occasionally put on mom's underwear together. Being female would be much better and we wouldn't have to hide it."

"I don't know how Melanie would take it if I came home wearing a dress," I said defensively. "We would have to move."

"Mom would accept it," said Brandy. This mother-daughter talk was showing me an insightful side of my son/daughter that I had never before seen. "I just love my new female body and I really don't want to lose it. Once my curves are gone they'll be hard to get back."

"I have to admit baby girl, " I stated, "When we were having our hair done in the brading shop, I was having the time of my life. I would love to get to keep going back and getting new styles and weaves."

"We could keep taking ballet as a family," said Brandy, "We could be the ballet guys."

I paused for a few minutes and just held my daughter in my black arms; just cherishing my newfound nurturing instinct as a mother of a teenage daughter a few years away from leaving the nest. It was clear she still had so much more to learn about boys, dating, and life.

"My only real concern with you Brandy, is that you'll be taken advantage of by some guy."

"Oh mom," she said petulantly, "I know all about how to handle a horny teenage boy. I used to be one remember. You don't have to worry at all about my safety."

"Well," I said, "I just wanted to make sure. Its a mother's job to worry."

"Fiona is doing a great job teaching us. There is just one thing I want you to know. Even if we stay as girls, I don't want to have my penis cut off. I want to stay a genetic boy, even if my outside appearance is female."

"That is fine with me," I said, "I would rather keep my manhood if I was going to adopt an external female appearence. We would just have to stay on hormones."

"Oh mommy," said Brandy, "You're the best mommy a girl could ever ask for."

Just then, Kendra came in the door and hopped up on the bed to join us. The three former Thompson males were sharing a girly bonding night. We kept talking about our techniques for making-out and heavy petting and handling a hormonally challenged teenage boy. I noticed that as we were oblivious in heavenly speech, I was subconsciously curling and braiding Brandy's hair. Yes, even if we wen't back to being boys, things would surely change no matter what. My sons would still sneak into their sister's room and try on her clothes all of the time.

"Have either of you girls been playing with your dildos," I asked them? They flashed looks of embarassment on their faces.

"I play with mine all the time," said Brandy, "I want to get really good at being a sexual girl. I like to suck on it as I go to bed."

"How about you Kendra?"

"I like to hold it and rub it," she said sweetly.

"Are you girls still masturbating?"

"Yes."

"Have you girls tried to do the anal thing that Fiona showed us," I asked?

Brandy laid a trap for me and said, "Have you mommy."

I was kind of embarassed but I had to speak the truth. "Yes I did, and it felt great. I thought it might hurt at first, but we women have to be able to take anal sex. All you have to do is just slip it in, and once it goes in the first time, it feels great afterwards." The girls listened with amazement as I described being penetrated like that.

"There is no way I am brave enough to try it," said Brandy.

"Me neither," said Kendra.

"But what will you girls do when your husbands want sex. We don't have vaginas, so we have to let them take us in the rear." The girls looked at me thoughtfully for a second, realizing that I was right. "Fiona taught us this stuff for a reason."

"I'm too scared to do it by myself," said Brandy, "But I'll let you stick your dildo up my butt."

"You can do me too," said Kendra.

I was so proud of my sons; they were such little troopers. I got up and went over to my panties drawer where I produced my massive nine-inch dildo. Brandy and Kendra got up and stood by the edge of the bed. I was ready to deflower my sons into sexually experienced young black girls.

I went to Brandy first and pulled her leopard print leotard off of her shoulders. I took down her garment, revealing her bare back and pink bra. I got down to her butt and took her tights and shaper panties down to her knees, reexposing her butt and penis.

"Okay," I said holding the dildo, "I'm going to enter you now."

Ever so gently and lovingly I slowly inserted the lifelike penis into her butt. She let out a squeal of pain but soon I had it in. "I have it in now."

"Take it out momma, take it out."

I took it out and then I stuck it in again. "Wow," said Brandy, "It doesn't feel so bad now." Kendra watched fascinated and nervous, knowing that she was next.

"You just have to get loosened up." I thrust it in and out about ten more times.

"Fiona was right, it feels fine once you get used to it," said Brandy, "I could totally start doing this."

I was satisfied that Brandy had learned and Kendra already had her leotard and tights down. For a second I couldn't believe that I was ready to do this to my youngest son. Brandy watched me as I used the dildo on Kendra and she seemed to like it.

"I love being a girl," shouted Kendra. After I was done with her I helped her get her clothes back up and we returned to cuddling on the bed. Brandy and Kendra held their dolls close to them. We had shared the ultimate girly fantasy. As guys we would have been branded as freaks but this was acceptable for us as women.

I imagined Mike as Melissa, a busty 16 year old blonde girl who loved ballet and boys. She would just be an absolute beauty and she would have guys lining up for dates. I would sit in the stands and watch Melissa cheer at the football game, or I would go with Julie to watch her dance recitals. Melissa would be valedictorian of her High School and I would have tears in my eyes as she went off to college. She'd find a successful guy to settle down with. As for Kevin/Kendra, well, I had no idea. I assumed that he would be happy either way. But he was at that difficult age where it was difficult to really get him to commit to anything, much less choose his gender for the rest of his life. We had plenty of time to let it play out. For now, we were just going to enjoy being little black girls.

Irritatingly, in this house, whenever I had to use the restroom, I always forgot to sit down and then the toliet wouldn't flush. We were being trained.

###################

We all fell asleep in the same bed that night. Thankfully Fiona let us sleep in and get some rest because we had to spend the afternoon getting ready for the debutante ball. I woke my sons up and we all took off our leotards and tights. I pulled out a new three-pack of sheer pantyhose, because we wanted to wear new tights under our ball gowns. I was kind of sad that I didn't have a date tonight but I couldn't blame myself because I had been stuck in the house or at Hooters and I really had had no opportunities. Deep down, I wasn't really ready to start thinking about doing anything sexual with guys. It did feel good playing with the didlos but I didn't really equate that with having an actual man.

My sons on the other hand had all day at school to socialize with boys and get their phone numbers. I was eager to meet their dates and introduce myself as Monique Washington.

Fiona had us all meet in the living room wearing nothing but our strapless bras and sheer pantyhose. Fi was in a short white halter dress with sequins and she had bare legs. She had the dresses us guys were to wear on racks. Kendra stepped into a sleek yellow gown with spaghetti straps with a skirt that ended at his mid thigh. It really showed his sexy arms, shoulders and legs. He slipped on a pair of heels.

Brandy put on a purple prom gown with sequins and a fluffy three layered skirt. The top of the dress was low cut and showed her impressive cleveage. I put on a sleek little black dress. Brandy and I wore long matching gloves to go with our dresses. Fiona spent about an hour putting jewelry on us, fixing our hair, and doing our makeup. It was a ton of hard work to be girly.

After what seemed like six hours, Fiona had us all finished and we were three goddesses ready to be seduced. She pulled out her digital camera and snapped about 200 photos of us. We smiled and posed.

Around 6PM, there was a knock on the door, and two little boys were standing on our porch. Fiona opened the front door and said, "Hello."

One of the young men was a nerdy little white boy with pale skin and glasses. He looked like Harry Potter and I figured he was Zack, Brandy's date. The other was a little black boy about 14 years old and he was here for Kendra. I could tell the boys were impressed when they saw how stunning my daughters were that they were ready to take out.

"You must be Zack," I said to the little white boy.

"Oh hush momma," said Brandy, "You know Zack." It was true, I had seen them talking for about twenty minutes at our girly challenge.

"And I be Jamal," the little black boy said to me. Kendra rushed over to him. As a white guy I would have lost my mind if one of my sons chose to date a black girl, to say nothing of a black GUY. But since we were all now black women it seemed totally natural. All of this was just innocent fun and its not like any of us could get pregnant. Jamal and Zack put corsages on Kendra and Brandy and they smiled and held eachother as Fiona snapped yet more group pictures. We were going to want to remember this special night.

I would be a chaperone as my daughters walked out to the Limo arm-in-arm with their guys, clutching small purses. I just hoped Brandy and Kendra remembered our talks about sex and Fiona's lessons. We were all in high heels, and our heels clicked as we got into the Limo.

The Limo dropped us off at a massive convention center. There must have been 700 guests inside. I was a little nervous so I went in and checked my makeup.and freshened up. But I couldn't stall forever and I knew I had to go back out and mingle.

Zack and Jamal were already spinning my sons out on the dance floor. I was going to just hang out at the bar all evening, despite the risk of appearing as a prostitute. I ordered an apple-martini and began to slowly sip. But not after 5 minutes of being alone, a guy with a striking resemblance to Matt Damon came up to me and introduced himself as Craig.

I was taken a bit by shock and Craig could see that I was nervous. "Relax Monique," he said to me, "I work for NBC. I know all about "Joe.""
I was a little relieved.

"So how am I doing as a black woman," I asked him?

"You are just outstanding," he said to me, "You are the paragon of feminity. Your sons look really good too." Those words felt satisfying to hear.

"How do you think I am doing against all the other guys," I asked.

"We really can't divulge that information," he replied, "But I didn't come over here to talk about the game. I came to tell you that you are the most gorgeous lady I have ever seen and I was wondering if you wanted to dance."

I was stunned and compelled at the same time. I had nothing to lose, and the hormones were making him look attractive and appealing in my eyes. I lost my inhibitions and threw caution to the wind. "Yes," I said.

He grabbed my hand and led me onto the dance floor. Fortunately, because of dance lessons, I knew how to be led by a man during a Waltz and a Fox Trot. I suddenly realized that Julie would see me on TV dancing with a guy, but it was too late. In any case, it was just all part of the game and she would have to understand that. The hormones were changing me in ways I couldn't control. It was nice being held in strong arms.

"I always wanted to dance with a Hooters girl," he said. I blushed.

The hours flew by and soon it was time for my family to be introduced into Dresden society for the Emcee. All of the 18 contestants in attendane formed up in the center of the dance floor with our dates. I was introduced as Monique Washington, mother of Brandy and Kendra Washington.

We shared a solo dance and afterwards I lost track of my daughters but I was having too much fun with Craig to care. He told me that he was actually the primary developer of this television show. He told me how he had spent his teenage years living as a girl with his transgendered dad but had reverted to being a guy before going off to college. It was his dream in life to produce the defining cultural reality transgender television show that would make crossdressing and transvestism acceptable in mainstream America, much in the same way Homosexuality and Interracial Marriage were gradually introduced into the consensus of American society.

But crossdressing by itself wasn't bold enough, and the executives decided that the guys would have to change their race for the show to really be bold enough to shock the public into watching. He apologized for using my family as unsuspecting guinea pigs, but he explained that we would not have been able to get normal guys to do this if we gave the game away at face value. To my surprise, he told me that before our first season airs on television, NBC will start filming the second season of this show in a town in Vermont. The difference is that the white guys will be changing into Japanese girls instead of Black girls. I silently wished to myself that I could be a part of that season too.

But Craig surprised me and said, "If you and your family want, you can come on as guest coaches for the 2nd season of the CHALLENGE and help the next group of guys transition to Japanese girls."

"I'll have to think about it," I replied. "So Craig, my sons were asking me last night if it would be possible to continue on their lives as Kendra and Brandy instead of going back to being boys?"

"Would you support them. Are you going to remain female?"

"We're undecided. We were just wondering if the option was there for us to keep being girls?"

"If you really wanted," said Craig, "We could give you lifetime supplies of hormones and tanning solution(if you wanted to keep being black.) On the other hand, we could set you up on the typical route of sex-reassignment surgery."

"My sons and I are adamant about retaining our male private parts. We would just want the external appearence of males."

"Oh, don't worry about that," said Craig, "The hormones are cheap and we could sell you a lifetime supply for like 200 dollars."

An hour later I kissed Craig goodbye and told him that I hoped to see him again. He said that he could count on it, but he had to go take care of some emergency business. Just then, Kendra ran up to me and told me that she couldn't find Brandy or Zack.

We looked all over the center for them, and then finally we went outside and caught Brandy and Zack making out on a bench.

"Oh don't get mad at me momma," pleaded Brandy, "I love him."

"Come with me this instant young lady," I commanded. "It is way too late."

Sullenly, my daughter did as she was told and waved goodbye to Zack. She blew him a kiss. I told her that she could be his girlfriend but it was time to go home.

TO BE CONTINUED

The Challenge Part 006

Author: 

  • TylerD

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

WE find out what is going on with Kendra.
 

The Challenge: Part 6

By Tyler


 

ONE WEEK AGO:

As we were doing as a family, we all stayed in our leotards and tights for the night. I had kept on the orange tiger striped leotard that Fi had chosen for me earlier. I had decided just to spend my off night in my room reading my girlie mags, but I got bored and went to see what my dad and brother were up to.

I went into dad's room and saw them cuddled on the bed having a girl talk. The conversation was pretty tame at first but dad got to asking us about if we were playing with our dildos. I was horrified when Fiona had given me one and I had thrown it in the top of my pantyhose drawer and I hadn't touched it

"So Kendra," my dad asked me, "Have you been using your dildo?"

"Yes mommy," I lied.

But then dad explained to us how we had to really experience anal sex and practice with our dildos in order to be ready to do our duty for our future husbands. I was terrified at the thought of actually being with a man. I had thought that we were only in this for half of a year. But it seemed as if my dad and brother had other plans for our future. Mabye the Thompson family wasn't coming back. Deep down, I had been fighting all of these changes but I was so powerless to resist. I had just gone with the flow and gave the answers my dad wanted to hear. I had always been afraid to disagree with Joe and I had decided it would just be the best for me if I went along with the program and hopefully I would come out in one piece.

It was not all bad, of course. I was just aghast the first day, but being a girl had its good parts. I did like wearing some of the cute little outfits and at least I got to be around the hot girls all day. Preppy girls previously wouldn't give me the time of day but now they wanted to chat all of the time. I did like the feeling of things like nylons and leotards but by the time this was over I was going back to Kevin with no questions asked. In the challenge, had decided to impress dad so I tried as hard as I could and picked up 11 phone numbers. I was sort of taken by surprise when Jamal had asked me out to the dance the other day but I accepted because that Craig guy had given me a cue that I had to take up Jamal's proposal and if I didn't we would be punished as a family.

I was enjoying being dressed by Fiona. All of my sports and video games and boy's toys had been taken away so I had nothing really to do buy play with the girl stuff and read those magazines. I would practice my dance moves and such things but deep down I was just counting down the days until this was all over.

I was lost in such thoughts as dad kept on talking. "What are you girls going to do when it comes time to please your men. We don't have vaginas of our own, so we have to allow our husbands to make whoopie in our heinies. Why don't you girls just let me practice on you. Come on, we'll do it together as a family. We have to master the skills Fiona wants us to learn."

Brandy seemed excited and said, "OK mommy." She got up and stood at the side of the bed. I was silently petrified. Dad retrieved his dildo from his tights drawer. The last thing I ever wanted to do was really be dating some guy. Life was so unfair. I wanted to be out playing baseball, not dress-up. Couldn't they see that I was a boy and that I couldn't be changed?

I watched as dad pulled down my brother's dancewear. My dad put some lotion in his butt and then he began to gently slide the tube into Brandy. She seemed to like it. After my dad was satisfied that Brandy had gotten the experience, he said to me, "Okay sweetie, its your turn."

He pulled off my leotard and gathered my dancewear down at my knees, exposing me. He oiled me up and I felt the thing enter me from the rear. It felt alot better than I had thought it would. So this was what women and queers went through. I began to get excited.

"I love being a girl!!!," I shouted out in sudden ecstasy. I felt dirty and weird but I couldn't help myself. I realized that hidden cameras in the room were filming us but I was sure that they couldn't air this on national television. Dad took my tights and pulled them back up over my butt and then he gently helped me get my leotard back on. I realized just how loving he was as a mother, and how much he enjoyed helping his daughters be female and dress us up and do our hair. We were all somewhat exhilirated.

After the moment had passed and we were all calmed down, we all jumped back up on the bed. Dad asked us, "So do either of you think that you'll date guys all the time?"

"Mommy," I replied, "Deep down, I'm still a boy, and I like girls." I saw a look of disappointment in his face when I answered. This whole thing was so confusing. I had no idea what I was doing here. I wasn't even thinking about the prize or the pagent or winning anymore. I just wanted to keep my sanity, my manhood, and get the hell out of here. What the hell were we doing; three guys in white tights and the cutest little leotards. Dad held onto the dildo, just stroking it and rubbing it against his smooth crotch as we continued to talk. Brandy went and got hers and fondled it like she was playing with a Game Boy. Her little butt looked really cute as she sauntered off, black legs and white tights and a curvy figure being held in by a leopard-print leotard; the bottom riding up her butt. Our manhoods had totally vanished under our nylon sheaths. Ahh, whatever happened to our boxer shorts. Why did everything about women's clothes and ballet dancewear have to be about sex? It seemed like the main thing about dressing as a woman was coyly advertising our curvy physiques so guys would notice us. Three guys in white tights playing with sex toys; Great.

############################

Brandy had been going on and on for the last week about how she was going to try out for the role of the Heroine in Sleeping Beauty. I told her that she had no chance against the 17 year old ballerinas but she had been practicing all of the steps anyway and was determined. I was so sick of hearing her go on and on about being Sleeping Beauty and the halftime routine she was going to perform at the halftime dance and how great here FHA meetings were. "You are a guy for god sakes," I thought. What are you doing getting so excited about all of this black girl stuff. We weren't meant to actually like being female. The point of this show was to film us struggling to pull on our tights and put on our bras and to silently resist our coaches. And my dad was a regular black June Cleaver. Back home, we would hear nothing but taunts about us wearing panties and kissing guys. We'd have to move to Romania to get far enough away?

"You're not even a real girl," I told him, "What makes you think you have any chance against Kelly or Cynthia?"

He didn't even answer my question and he mentioned how he wished Shane Johnson, captain of the basketball team, could see him now.

So my big retarded older brother/sister was getting ready at the dance studio to audition. I was sitting in there, as bored as I could be, wearing black tights and a purple leotard with ruffles at my shoulders and pink trim around the bottom. I realized how exposed my legs were and the outfit was showing off my entire figure. I was glad at least I was thin and didn't have to be embarassed about being a heavy girl in leotards and tights. I just sat there in a folding chair kicking my legs while we watched the older girls go on and on and try out for the big roles.

"Have you talked to Jamal since the dance," dad asked me?

"We broke up," I said curtly, not wanting to discuss boys with him.

"Oh, sorry to hear that," he said, "Is everything all right."

"Its fine," I snapped. I hoped he would think his "daughter" was just going through a phase and her mom would mind her own business. Truthfully, I was getting fed up with just how gay or queer or whatever dad was becoming. Here he was, a 37 year old guy, dressed like Michelle Obama at a ballet class, in a white cap-sleeve leotard spangled with red roses and wearing white tights. This whole thing was a girly nightmare that no guy should have to endure. Say what you want about role-reversals in 21st century America. Men are still men and women are still women, even if Hillary Clinton is running for President. I wondered if 20 years down the road gender roles would reverse all across America and all women would work and guys would be expected to clean, cook, and raise children. I was still an old-school guy at heart. They would never change me.

My brother was in the bathroom fixing his makeup and pulling his hair back before it was his turn. It was one year ago to the day that he was going for the 1st chair bantam-weight class in Wrestling. To me, he seemed way more excited about ballet auditions than he had about any of his old sports. Honestly, if he wanted to stay as a black girl, that was fine with me, but he or my dad wouldn't take me with them.

I had to admit that my brother was an absolute angel when he came out and took his place on the dance floor. He was absolutely captivating in a baby pink long-sleeved leotard with an attached pink short skirt with white roses. He had on white tights and pointe shoes. The bright pink and white colors were quite a contrast with his ebony skin and hair. Yes, Mike was gone, replaced by Brandy, a teenage black ballerina who loved to wear cute tights and date guys. I knew at least he would do comparably well at the pagent because he had become so beautiful and feminine. I can't say I would blame him if he wanted to stay a girl. He seemed much happier, more accepted, and well adjusted as Brandy than he had as an agressive boy who kept getting rejected by girls he was trying to ask out. Brandy got to spend all his time with Zafira and Krystal, but I couldn't tell if he was interested in them as far as dating or if he considered himself female like them and just wanted to be regular friends. Heck, perhaps he hadn't even made up his mind yet. But he was every inch the black girl he had dreamed of becoming.

It all made sense to me as I thought back to when Mom kept dressing him in my older sister's ballet clothes. I was only eight years old then and I remembered how much fun Mike was having as mom would spin him around the room in his sister's tights and dresses. "Of course," I realized, "Mike had been secretly loving this the whole time and had been a closet crossdresser for the last five years!" All of the pieces of the puzzle fit together. This was paradise for Mike/Brandy. I knew that my dad was every bit as passionate about this contest as Brandy was and I was outnumbered.

Then, I remembered when he modeled his Junior Varsity cheerleading outfit yesterday. Brandy had little blue and white ribbons in her hair and the skirt of her jumper was sinfully short; The girls had been issued blue briefs to wear underneath. He had on sheer hose under the blue jumper and he just looked so sweet and happy waving his pompoms and singing, "I'm sexy, I'm cute, I'm popular to boot." Dad was clapping his hands for him like the mom in "The Nutty Professor." It wasn't just about getting close to the other cheerleaders for Brandy, but a rite of passage towards being a woman. I was sure he had several offers from guys to be escorted to the upcoming homecoming dance. I had gone to a couple of the junior cheer practices for middle-school girls but it wasn't really for me. Now, my brother was a little fairy in his pink outfit here at the studio.

Now I had all of the stupid cheer ditties stuck in my head.

Ever so gracefully and delicately, Brandy went into her little dance the minute the music started. She swayed back and forth doing all of her arabesques and such things. I was actually surprised at how good she really was and I couldn't take my eyes off of her. She was better than what I had expected. As she danced and froliced about the floor, her little pink skirt would fly up and show off the smooth bottom of her leotard. She danced for three minutes without making one mistake. At her last move, she struck a pose and flashed a huge smile. Then, she curtseyed as all us dancers had been taught. Like a girl, she skipped lightly off of the stage. I knew that she knew that she had just done an outstanding job and it wouldn't surprise anyone if she won the part. Fiona and dad were watching and I could tell that they were really proud of their daughter.

"How did I do mommy," Brandy asked excitedly. I noticed just how flippant and feminine all of Brandy's everyday movements had become; the little dips at the hip and coy smiles and flirtatious movements.

"Girl, yous was the bomb," mom replied.

As class was ending, some of the teen girls pulled out digital cameras, and we all took pictures of eachother in our ballet outfits, posing sexually. It was a whirlwind of femininity. We were hugging other girls, laughing, dancing, singing, and smiling without a care in the world.

#######################

We were off to our challenge the next day when the phone rang. Fiona had us all put on black tights and sport's bras, over which we we were allowed to wear a T-shirt and sweat pants. Brandy went to answer the call and it was Amanda informing her that she had been chosen for the female lead in Sleeping Beauty.

You would have thought that she had won the lottery with the high-pitched screams and cries of "Oh my god, Oh my god, Oh my god!!," that carried throughout the house.

"What is it girl," dad asked?

"I got the part, I got the part!!!"

"Oh baby that is so precious." dad and Brandy hugged eachother, jumping up and down and actually crying tears of joy.

I decided that I had had enough of this charade and I was finally going to tell dad how I really felt about all of this. I was going to tell him that I didn't care about the contest or any of this learning to be girls crap. I was going to change back to Kevin as soon as possible and go back home to my real mom. He and Mike could stay here and be gay if they wanted, but I was having no more of it!!

"Mom," I asked firmly, "Can I talk to you in private for a minute."

"Of course sweetie," he replied in his typical rococo Monique voice."

We went into the bathroom. I began and said, "Look dad, Some parts of this contest have been fun. The fact is that I hate being Kendra. I am telling you that I demand to change back to Kevin. I'm not into dating guys or dancing ballet or being a cheerleader or any of this stupid stuff. I am a boy and I want to go back home the way I was."

Dad didn't even look at me. All he did was examine his angelic face in the mirror and check for non-existant flaws.

"Did you even hear me!!!," I screamed in my high-pitched black-girl voice that sounded like nails on a chalkboard to me every time I opened my mouth.

"Of course I heard you dear," he replied. "The problem is that we've come too far to back out now. I wished you would have told me on the first day that you didn't want to be here, and then we could have worked something out with Matt and sent you back. Honestly, I thought that you were just enjoying yourself like we are. You seemed so happy and unconcerned."

"I was too scared to say or do anything," I told him, "I didn't know it was going to be this extreme. You wanted me to become female and I didn't want to defy you. I want you to know that I have liked getting to bond with you. I feel like I finally know you and that we know alot more about ourselves as people. But I can't keep going."

"Listen sweetie," said dad, "Women just have to put on a happy face and keep going. And all guys have to just suck things up and do things in life that they don't want to do. I didn't like working as a car salesman for the last 17 years. I hated seeing my sons turned into girls at first. When I saw how happy being a black girl made your brother and how close we were getting, I changed my mind. Sure, I would rather be masculine, but I was a terrible father and this is my chance to right the wrongs. I missed out on your childhoods but now we get to become close again."

Dad continued, "As for you, you're only 13 and you're learning that people have to do things that they don't want to do. In your case, it is being a girl for the next five months."

I wasn't convinced and said, "But I think being a girl is going too far. Why couldn't I just get a paper route to learn a work ethic? I don't want to lose my manhood."

"LIke I said," said Dad, "We're in this for the long haul. If you back out, we forefit, and you will not ruin this for me or your sister. If you don't remember, we had a bunch of debt to pay for all of those sporting activities. If we don't win that money, we could become homeless. Being here is not a matter of choice. You might as well just make the best of it and enjoy it. It will all be over soon. Then, you can go back to being Kevin."

I realized that I was taking the wrong approach. "So dad," I asked, "How do YOU like being Monique?" I needed to really get into his head and find out what was going on.

"I like it just fine dear," he replied, "We all have female sides and they just come out."

"Are you going to stay as a woman," I asked him?

"Well," he said, "We both know your brother is having the time of his life. As for me, there are so many things I like about being female and alot of things I like about being a guy as well. Before you came into our room the other week, Brandy was telling me how she might want to stay as a girl, but become a white girl instead."

"I'm not surprised she wants to keep being female," I replied.

"I haven't told anyone yet," said dad, "But I am seriously considering living as Monique for the rest of my life. I would stay with our family and still be married to mom, but I would be in disguise as the housekeeper."

"But what if mom wouldn't accept you as a woman," I asked him?

"I would be willing to let her be with another man for sex," he said. "I just know that once Monique is gone, she will be gone forever. Once you go back to being Kevin, it would cost alot of money to bring Kendra the black girl back."

"Why couldn't you just be a guy for most of the day like you were with Joe and then just wear Mom's clothes when you wanted to be a girl?"

"Like I told your sister, it has to be one or the other. It would be too confusing going back and forth. If I built my muscles back up and quit taking hormones, I would just look like an absurd drag queen instead of a classy and convincing lady. I would want to go out dancing and shopping and I couldn't pull it off."

"So if you decide to be Joe, you will never dress up again? Not even wear my mom's panties?"

"I think you can expect to have Monique around for a long time, more so than anything else," he said.

This was awful news. I had no chance of getting out. Running away wouldn't solve anything, I would still be a girl. I wished I could wash the stupid chocolate off of my skin and cut my curly hair and burn my bras and dresses in a giant bonfire. I was absolutely stuck.

#####################

We drove back to the convention center for our next challenge. They had converted the ballroom into a giant modeling studio. Our challenge was to model bikinis and little dresses as a family and professional modeling judges would score us. We wore simple clothes so we could change easily.

I didn't have quite the same enthusiasm this week as I had earlier. Makeup artists took the three of us and went to work on our faces with stage makeup. I was disgusted as they gobbed the foundation and concealer on my face. It wasn't even real, I was just someone's dress up doll. The sytlist was an attractive Latina lady and she introduced herself as Ana. She looked like that mom from the show Ugly Betty.

I took off my T-shirt and sweats and stood there in my black sports bra and my black tights. Ana pulled down my black tights and pulled a pair of sheer pantyhose out of a drawer. Quickly and efficently, she pulled the new tights up my legs. I stepped into a very tight halter-top black dress with a skirt-line that ended just below my crotch. The dress was really tight and showed off my hourglass figure. The tights covered my lower body and made my legs look so long and sexy. I loved the feeling of being encased in tight nylon, and that was the one thing I would miss. I stepped into a pair of black high heels, which had the effect of forcing me to take tiny, dainty steps, and pushed my butt up even more prominently. I thought the feeling of sticking a nyloned foot into a high heel was sort of erotic and tempting. Ana put a silver bracelet and a gold necklace on me, and I looked like a very young girl going out to a club or waitressing at a swank bar.

Brandy was in a short pink minidress with sequins and she had on white tights and pink heels. Dad was in a red sparkly minidress with spaghetti straps and he had on sheer hose. They both wore spiked heels to match their dresses. We were all given matching purses and we looked like three black girls out to pick up some boys! Matt ushered us over to the photo area and we were instructed to pose and model our outfits. The best set of pictures by any family would win another 100,000 votes. We were going to be second to go as a group. We looked over and saw the rest of mother/daughter combos getting made up and dressed in cute little outfits. Leticia's family was already getting their pictures taken. Her mom was wearing a tight white minidress with white tights and her daughters were in black tank dresses with sheer hose. It was sickining to watch former guys whore themselves out like this.

My dad was sensing my discomforture and he said to me, "You better put on a pretty face and smile."

So we went and took our snapshots. Brandy and Monique were having the time of their lives, primping and preening. They were sticking out their legs and flashing lascivious smiles. They were saying, "Come and get it." I was sure that America would eat it up. They were sexy women, I had to admit. But I did not have quite the same enthusiasm I had had that day Fiona took photos of us in our princess leotards. I hated being a "sex object" Here I was in my little dress and my little tights. I blew a kiss flirtatiously, imagining that I wanted every man in America to think that I was a black goddess who would give him a blow job. I sucked it up and got through it. If there was one thing I was good at in life, it was getting through things. Whenever I was in tights, I liked the feeling of being in nylon, so I would perk up a little bit. Here we were, three new girls being forced by circumstances to shed our male identites and become inferior colored women. How far we had come since the days of Civil Rights marches.

My dad and brother were in oblivion having the time of their lives, and to their sadness, the first part of the photo shoot came to an end.

"That's a wrap girls," the director called. Dad and Brandy hustled off to get changed into swimwear, but I saw Craig out of the corner of my eye and decided I had to take a chance and see if I could convince him to send my home with no questions asked.

"Craig," I called out running up to him. I was being slowed down by being in heels, clicking embarassingly on the tiles. The wind blew against my tights as I ran like a little girl.

"Brandy," he said, "What's up."

"I have to talk to you," I said, "I was wondering if it would be possible for me to get out of this and go back to being a guy? I don't want to penalize my mom and sister, because they've worked so hard at becoming women."

"This is such a shock," said Craig, "Your dad told me that you and your sister were having a blast becoming girls."

"I was misleading him because I wanted him to be proud of me," I replied. It was going to be tough to convince him.

"What did your dad say about all this," he asked?

"He said that we came too far and we were fully committed," I replied.

"Look," said Craig, "Five more months is not that much longer. It seems like a long time because you are so young. But you should know that your family is doing by far the best with our focus groups. I would say that you have very good odds of winning."

"I don't care about the money," I stated, "My pride and manhood is more important to me."

Craig reflected thoughtfully for a second. "You don't have to just appear as a man to have honor. It is really what is on the inside that counts. There is the old saying of never judge a book by its cover. Besides, being a girl is not the worst thing that could happen to anyone."

"Its not," I asked, "How would you know?"

"I spent my teenage years as a girl," replied Craig to my surprise. "My mom had three boys before me, and by the time I was 14, she didn't want any more kids. She decided she wanted to get to raise at least one girl, so one day all my boys clothes were gone and all I did was wear dresses and go to ballet class. I hated it at first but I just accepted it and eventually I began to enjoy being feminine and going on dates and being treated like a lady. I spent all of High School as a girl, but I had to go back to a guy when I was ready to go to College because they couldn't change my birth certificate. I put forth the premise of this show based on my experience."

"How did your dad feel about all of this?"

"That is the point I am trying to make. My mom absolutely dominated my dad. He looked like a man to the outside world, but my mom had him in the kitchen wearing an apron and doing laundry. So being a man is really defined more by actions than appearences."

I was beginning to understand. Unfortunately, I had to go back and get changed into my bikini. Ana took off my dress, shoes, and tights and I was put into a pink bikini. I had to step into a pair of plastic stripper shoes. My family was already waiting for me; dad in a lime green bikini and Brandy in a purple bikini with polka dots.

We snapped some more pictures and soon we were back over to get changed into our wedding outfits. Dad would be the bride, Brandy would be his bridesmaid, and I would be his flower girl. Our assistants put white tights on all of us. As Ana was changing my tights, she said to me, "I think it is really cute how you guys are doing this."

"Oh yeah," I retaliated, "How would you feel if your sons were being forced to be sissies."

Ana laughed and said, "I've been dressing my twin boys as girls for the last six years. I don't think you realize how common this sort of thing is. I bet a number of girls at your old school were really guys and some of the guys used to be girls."

"I seriously doubt that."

Ana pulled a cute little pink dress with lacey shoulders over me. "Crossdressing is the future," she said. "My girls are going to make some CEO lady very happy some day. They are learning what they need to know about how to be good submissive husbands."

"Well, that will never be me," I retorted.

"Have you looked in the mirror," Ana said. She handed me a boquet of flowers. She took all of the braids and beads out of my hair and brushed it into a conventional wavy style

Dad had put on white stockings and was now in a white-velvet wedding dress, and he was wearing a veil. Brandy was in a sleek teal blue bridesmaid dress. We went over and snapped the final set of pictures as a happy bride with her two daughters who was getting ready to be married off to the man of her dreams. With the many new perspectives I had learned today, I began to see "The Big Picture." It was not just about me. I was going to make the best of things. I realized that being a man was a privilege and not a right. I had to earn the right to call myself a white boy. Soon, I would shed my tights and get back into my boxer shorts. To do it, I had to be Kendra Washington, schoolgirl, ballerina, black girl, to the best of my ability.

If my dad and brother wanted to be women, I woudn't stop them. I just wanted them to be happy. I wanted to be happy.

The Challenge Part 007

Author: 

  • TylerD

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

The Tension and competition heats up between Brandy and Leticia. The Washingtons begin to think long and hard about their future.

 

The Challenge: Part 7

By Tyler


 
This is absolutely incredible. Here I am at the National Teen Ballet Finals in Decautr Alabama. I look in the mirror and all I see is Ali Larter. All the boys and my parents can't believe how much I look like Ali Larter; Just a busty, hot blonde with fair skin. It had taken almost a year for my hair and skin to get their Nordic color back. I have my gorgeous hair pulled back into a ballet bun. My face is made up. In five minutes, I go on stage, my future as a ballerina and future dancer at Juiliard on the line. My heart is pounding, and my male organ is throbbing inside of my tutu and tights. My boyfriend/dance partner has no idea that I was once a guy. This muscular black guy who is ready to hold me in his arms is looking fine in his costume.

I am in pink tights and a big pink tutu, and I am the essence of femininity. My tutu gives me little pink ruffles around my crotch, from which pink tights covering long milky legs come out. I have on my pointe shoes and just feel all done up and pretty as I prepare for the Pas De Deux. Melissa Thompson is almost ready. Will my parents be pleased, seeing their former son on stage doing the most girly thing imaginable? I remember that I have to keep a big smile on my face at all times. My only worry is that my big floppy breasts will bounce too much, but my longline bra, god willing, will hold me in. I hope I didn't run my pink tights when I pulled them on my now smooth legs. But I know everything will work out, because I am a winner in life. Hopefully, I will go and be a ballerina, then a model, and finally an actress.

I am already going to be valedictorian and Prom Queen of my new High School in Mississippi. When I transfered there two years ago from Knoxville as Melissa all of the girls there wanted to know what it was like to be from a big city and I made tons of girlfriends. I was the best ballet dancer at the town's dance studio and easily became head cheerleader. My sister told me all the time how pretty I was and how jealous she was of me. But I knew that this great new life would not be possible without the chance our family took four years ago. I constantly reflected on those crazy six months of the Fall and Winter of 2009.

Did my mom ever realize when she was taking me to Football practice when I was 12 that I would become her little princess. She never thought I would be in panties, hose, and hoop skirts. Mom even threw a big coming-out party in our big new house we purchased and the entire town came to see me come out in my dress. It was great being doted and fawned upon and everyone telling me how pretty I was.

#############################

There I was in the girls room of the dance studio, I took deep breaths as I prepared to audition for the lead female role in Sleeping Beauty. I was scared but I was comforted by the familiar feeling of rubbing my tighted legs together and feeling the friction of nylon on nylon. I was sweating in my pink panties, tights, and bra. I felt as nervous as Eminem in the movie 8-Mile, when he was preparing for his rap battle. I was only supposed to put my head down and get through this, not be enjoying life as Brandy. I was a guy for god sakes. Yet, my dad and obnoxious little brother were out there supporting me and hoping that I would do well in my audition.

I got the butterflies in my stomach under control and walked out onto the main dance floor of the studio. All of the dancers were sitting up against the side of the wall, all in their dance gear. I saw my dad and little brother sitting in folding chairs. My dad was in his white rose-spangled leotard with white tights and my little bro was in black tights and his purple leotard. Kendra looked as bored as he could be. He had seemed somewhat distant for the last couple days after having been so enthusiastic; I wondered if there was anything wrong. I had chosen the prettiest pink leotard I owned with a cute pink skirt with roses and I had pulled on white tights with a pink tint. I really wanted to look sweet and girly for this special day. What with the hormones I was taking, I felt feminine all of the time and I couldn't believe how big my hips and booty were getting.

Leticia/Luke was auditioning for the same role I was. She was emerging as my biggest rival so far and sure enough, she decided to audition for the same role I was going for just to frustrate my efforts to dance the female lead and get my face on TV. As soon as I told Amanda that I wanted to try out, Leticia just had to write her name down and audition too. She was up there now, going through her steps. Leticia was wearing a blue, green, and white striped leotard with an attached short skirt and white tights. Her "dad" Marissa and her twin "brother" Shaniqua were watching her, and I wondered what they were thinking about all of this. While my family had all been developing big breasts and butts, Leticia's family had stayed somewhat slender. Different genes, I guessed, had caused this.

To my surprise and relative disappointment, Leticia was actually not bad. I knew he had been kind of a dorky guy, but he was quite graceful in a quirky way at dancing ballet. He had sort of odd motions with his arms and legs but it seemed to work for him, and he came off as sort of a vapid, ditzy girl. As a guy, surely he was quite the science nerd but those demure qualities transfered well towards being a girl This last month, he had actually been transformed into a very attractive black girl who was becoming quite popular at school and was mentioned as a possibility to become captain of the JV cheerleading squad. I always saw her hanging off the arms of hot guys at school. It seemed like she was really growing into herself. She worried me most as someone who could challenge my bid to win this competition. I wondered if Leticia was actually interested in all of her little flirtations or if she was just playing up the cameras.

Leticia finished up her little dance and it was my turn. She did a little shimmy off the stage and she was cute and feminine to the point where I wanted to scratch her with my long nails. However, all I did was clap for her a little bit and smile like a good girl. I bit my lip and skipped out onto the stage and did a little curtsey. Dad applauded for me and my brother sighed and put his head down in his little breasts. Before I started, I looked in the mirror. Little did I realize what was going on on the opposite side.

"As you can see," Craig said to my mother and sister on the opposite side of the two-way mirror at the dance studio, "Your son has developed into quite the young lady."

"I just can't believe that these black ladies are my husband and sons," said Melanie with a look of shock on her face.

"We didn't want to keep you in the dark," said Craig. "We didn't want you worrying because you weren't hearing from them. We wanted to reassure you that they weren't down in some jungle."

"I can't believe how cute you made them look. Mikey looks so happy in his little tights doing his little dance. They all look like they're having fun."

"This is incredible," said Julie.

Luke/Leticia's mom was sitting there and she said, "I can't believe you made my boys into beautiful women. My son looks so pretty."

"I can't believe how big my son's breasts are," said Melanie.

"We kind of got carried away with ourselves," said Craig. "If less is more, think of how much more will be."

"How long will it take for them to change back," Melanie asked?

"The hormones and the tan will wear off in three months after the final day of the season," said Craig, "If of course they want to go back."

"What do you mean if they want to go back," asked Mel?

"Well," said Craig, "I have the obligation to inform you that your husband came to me and expressed interest in remaining as Monique, and he said Mike wanted to keep on living as Brandy. We can make that happen for them if they want. They wouldn't necessarily have to have an outright sex-change, but they could just keep their external female appearence. You will have the chance to talk with them about this."

"I can't say that I would blame them if they wanted to keep being girls," said Melanie, "They are totally convincing. I would never suspect if I didn't know better that they were really males. You can't even see their male organs through their leotards."

"We have the latest in crossdressing technology at our disposal," said Craig.

"I can't believe that they are doing this," said Melanie. "Mikey used to put on his sister's clothes from time to time but I didn't think that he would take it this far. I mean look at him in a pink leotard and white tights trying out for the role of a Prima Ballerina."

"A couple of our consultants from the NYC ballet have actually commented on Brandy's outstanding dance abilities and the quickness at which she picked up the steps. They said that she could have a future in dancing as a female or male if she wanted. It is just too bad that she has started serious dance training so late in life. I know if I would have started ballet as a girl earlier I could have gone down that road."

"So I should encourage her dancing?"

"Definitely," said Craig, "Tell me, did Mike have much going on as a guy?"

"No," said Mel, "He was just a C-student with no extracurriculars and he didn't have many friends."

All the female members of the participating families were back behind the two way mirror, watching the men in their lives audition for ballet roles. Craig turned to the group and said, "In a couple months, we are going to bring you all back, if you want, to participate in a couple of future episodes. We want you all to interact with your husbands and sons and you see them living as black women. We want to get gut reactions from them seeing you for the first time in their new bodies. You will get to live with them for a couple weeks and just see how you like your guys in a female role. Then, for a few days as we draw the show to a close, you all will get to escort your families back to your hometowns and they will be in disguise as black girls. We just want to get good footage of them going back to their old schools and jobs while they have a female appearence."

This was probably a little much for a couple of the ladies but Melanie was fine with it. "I just can't wait to see my husband and sons again, even if they will be dressed as girls."

"They might be a little embarassed but I'm sure that they will be happy to see you again."

"Melanie said, "My husband is so convincing as Monique. I can't believe that that is the same man I married. I wonder what it would be like making love to him while he is a black woman? I can't wait to put him in my hosiery, lingerie, and dresses."

The other ladies giggled.

"What," said Melanie, "I'm enthusaistic about this."

"Yeah," Julie said, "I'll get to play dressup and practice dance with my little sisters. Mikey is already a better ballerina than I ever was."

And I was out there dancing my little heart out for my mom and sister, and I didn't even know it. I felt so sexy in my little ballet outfit. As I wrapped up my dance, I smiled in the mirror, unaware my mom was smiling back at me. She saw her teenage son as a full-fledged black girl who was quickly forgetting about being a guy.

######################

My confidence had soared through the roof after Amanda called me and told me that I had won the lead role in the ballet. On Thursday, I showed up at school wearing a velvet green dress with a short skirt and I was wearing black tights and black heels. I put on about every piece of gold jewelry I owned and I wore a green headband in my long straight hair. I modeled in the mirror for about twenty minutes, just spinning and twirling and clutching my purse. As I was primping, preening, and smiling, I saw my dad behind me.

"Krystal is here to give you a ride," he said. "It looks like she got some wheels for her 16th birthday."

I ran out the door and hopped into her new purple Chevy Malibu. Krystal was in a yellow dress and white tights. "Damn girl," I said, "Your parents hooked you up. My mom won't buy me a car."

"Is nice," she said as she put on some rap music. We drove off to school.

Krystal said to me, "You are going to be so popular since you won the lead role. But I heard Leticia has been spreading some rumors about you."

"What rumors," I replied?

"That you're a slut and you've already been with five guys. She said that you like to give them anal."

"That ain't true and you know it. I see her hanging with a different guy every day."

"Well," said Krystal, "You better work it out with her." So that little crossdressing whore was trying to sabotage me. The only time I had even touched a guy since I had been here was my ridiculous little dance with Zack, who I didn't even care about any more. The only guy who I ever really thought about was Shane Johnson, captain of the Football team. I walked into the school in my cute little outfit, and my heels were clicking against the tiles. I felt my hosed legs rub together and I would miss this sensation if I went back to being a boy.

That morning in the halls I saw Leticia. To my anger, the little whore was drooling all over Shane Johnson and she was smiling and batting her lashes at his every word. She was wearing sheer hose and a red dress and she would let him put her hand on her leg and feel up her thigh. I could tell that Shane was just eating Leticia's disgustingly sexual and provocative attentions up. Then, she let him kiss her, My world was collapsing. I was going to ask Shane to homecoming and Leticia knew it, so she made her move first. She was so jealous of me for winning the ballet role that I wanted so now she was going to steal my guy. We were already bitter rivals for leadership of the cheer squad and the top prize of The CHALLENGE was going to be a no-holds barred fight to the finish. God, sHe was such a little skank.

I felt liked crying as I walked away. I had a genuine crush on Shane and I knew that he had liked me. But now, Leticia was spreading all these dirty rumors about me that I was a cheap slut who liked to take it up the butt. I could feel people staring at me. I wondered how far the rumors had traveled around the school. I hadn't seen this underhandedness and sabotage coming. When I started, I just wanted to put my head down and get through this but I set myself up by enjoying myself and doing well and now that stupid bitch was out to get me. Back home, I would have put a nerdy little worm like Luke into a toilet but now I had to get into a catfight with his female alter-ego.

Also, now I had to scramble to find a date for Homecoming. What was a girl to do? I was sure that all the guys would line up if they thought that they would "get some" but I wasn't going to lower myself any further. I needed time to make a plan.

##############

I dragged myself into the front door and dad said to me from the kitchen, "Hi honey, how was your day?"

"Terrible," I replied.

Kendra was already home and annoyingly, she said, "Brandy is mad because Leticia Jefferson asked out Shane Johnson, and Brandy had a huge crush on Shane!!!"

"You little runt," I said and I moved to slap her. She quickly got away and ran up the stairs. I tried to chase her but I forgot I was in heels. I tripped after taking three steps and I fell at the foot of the stairs. It was awkward trying to move in a little dress. "Ha Ha," laughed Kendra. I felt so ridiculous there in my short dress and tights, a rejected black girl who'se little sister knew all the rumors about her.

"Now now girls," said dad.

Kendra chimed in, "Yeah, everyone says that Brandy is a huge slut and she is taking Omar Wells to Homecoming."

It was true, I had accepted his date out of desperation.

"Kendra," said dad, "You know that those are just rumors. Now Brandy, why don't we have a talk before Fiona gets home."

"You are aware," I yelled at Kendra, who was sitting there with a stupid smirk on his face, "that Leticia Jefferson is really a retarded guy named Luke and you are really a little boy named Kevin. Look at you in a stupid jumper and tights!!!"

"GIRLS," screamed dad, "That is quite enough. Kendra, go to your room and start on homework."

Dad was in a blue dress with a blouse top and sheer pantyhose with high heels. He was preparing a fancy dinner for just him and Fiona. Fiona was going to be the "man" tonight and expect dad to have a dinner prepared for them. Then, they were going to sit down and have a private "date."

Dad told me not to worry about any of those rumors. "All you can do now is strike back and spread some rumors about her."

I went upstairs and began to plot.

To clear my head, I decided to change into the tutu and tights that I was to wear as Sleeping beauty. I took my dress of and I hung it up in my closet. I looked at myself in the mirror in just my lingerie and tights. I took off my undergarments and I pulled on my white tights and stepped into my tutu and ballet slippers. To clear my head, I did my solo one time around the room.

When I was finished, I sat down at my vanity. I reached for my blackberry out of my purse and I dialed up Andrea, a girl I liked from my cheerleading squad.

"Andrea," I said, "You won't believe what I just heard."

#########################

Kendra ran up to dad and said, "Daddy, I've changed my mind. I want to stay as a girl. I never want to go back to being Kevin."

"Oh sweetie that is so wonderful," said dad, and he picked up his son by the armpits and raised him up over his head and twirled him around.

"I'm totally boy-crazy and I found a freshman to take me to homecoming!"

"As long as I meet his parents," said dad. "What happened to make you change your mind?"

"It just hit me," said Kendra. "Mabye its the hormones, but I just love being a black girl."

"I like being your mom too," said Monique. Mom gave Kendra a big kiss on the forehead.

"Am I interrupting something," said Fiona? She looked at the two girls in the kitchen. "I don't want to interrupt a mother/daughter moment."

"Kendra was just telling me how she wants to be a black girl forever," said dad proudly.

"Yeah," said Kendra to Fiona, "I want to grow up to be a pretty lady just like you. I want to marry a nice man."

"I'm so glad that you want to stay female," said Fiona beamingly, "But you have school tomorrow young lady, so why don't you go upstairs and get some sleep." Kendra dashed up the stairs, still in her school uniform.

"My daughter is growing up so fast," said dad. "As you can see, I set out dinner for us."

"You guys have really taken well to becoming female. I expected more resistance."

"Kendra was having some issues recently, but we worked those out apparently," said dad.

"Well," said Fiona, "I'm very happy to hear that." Then, Fiona moved in to give dad a kiss on his big purple lips.

TO BE CONTINUED.

The Challenge Part 008

Author: 

  • TylerD

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

Omar walked me home from school and he was so sweet holding my hand the entire time. I was wearing my schoolgirl uniform with white tights that day and I had started rolling over the top of my skirt to make my hemline really short. The bottom of my skirt started just below my crotch and showed off my legs. I was worried that a teacher or a principal might say something but they had kind of a lax attitude towards that sort of thing and all of the girls were doing it. I had to be careful to cross my legs or else guys could look up and get a panty shot.
 

The Challenge: Part 8

By Tyler


 

Omar walked me home from school and he was so sweet holding my hand the entire time. I was wearing my schoolgirl uniform with white tights that day and I had started rolling over the top of my skirt to make my hemline really short. The bottom of my skirt started just below my crotch and showed off my legs. I was worried that a teacher or a principal might say something but they had kind of a lax attitude towards that sort of thing and all of the girls were doing it. I had to be careful to cross my legs or else guys could look up and get a panty shot.

It was clear that the hormones I had been taking had brought my development as a man to a halt and I was instead maturing as a teenage black girl would. I had the feelings and nurturing instinct of a girl and my dad and brother were experiencing the same changes. My dad had had a "second-puberty" had had been turned into a woman. My little brother was only just beginning to turn into a man when he was flooded with estrogen and transformed into a cute black girl.

"I can't wait to take you to the dance," said Omar.

"I can't wait either," I replied.

"Well," said Omar as we walked up my driveway, "You're home."

"I'll see you tomorrow," I replied coyly.

"You don't mind if I give you a kiss," he asked?

"Of course not," I said. And with that he bent down and stuck his tounge in my mouth. It was my first french kiss. He reached under my skirt and grabbed my butt with his right hand, and he put his left hand on my breasts. After it was over I was glowing. Carefreely, I waltzed into the front door. Kendra and dad were already home. I smelled dinner on the stove. Dad was wearing a short black dress with black tights and an apron.

My breasts still felt sensitive after Omar had touched them. Since I had grown my own, I would get an erection every time my mammaries would get stimulated.

Just then, out of the corner of the living room, I saw my sister and my mom sitting on the couch. "Oh my god, sweetie," she said, "I can't believe it is really you?" She got up and gave me a hug.

"Oh mom," I said, "It is so good to see you. It has been so long."

"I can't believe what a job they did on you," mom said, "I would never guess that you were a boy. Your hips and face are so feminine, and your boobs...."

"DoubleDs," I said proudly.

"Yeah Mikey, or should I say Brandy," said my sister, "You look absolutely amazing."

"Well," said mom, "Your father and brother are totally beautiful. Who would have thought that this was possible."

"It is weird seeing my little brother in a skirt and tights with big boobs," said Julie.

"What do you mean," I said petulantly, "I used to dress up in your clothes all of the time."

"So that is what all of those mysterious white stains were inside of my pantyhose," said Julie.

"Who was that guy you were with just now," inquired mom, before I had a chance to defend myself?

"His name is Omar," I replied, "and he's taking me to homecoming."

"Yeah," chirped in Kendra, "Brandy has a boyfriend."

"He's not my boyfriend," I blushed, "We are just friends."

"Than what were you doing kissing him?"

"Oh, you saw that," I replied.

"Well, we might be more than friends."

"Yeah," said Kendra, "Who knew Mikey was really gay?"

"Now now sweetie," said mom, "It is perfectly natural for a teenage girl to get a boyfriend. You're just still probably too young to feel that way."

"Oh no," I replied, "Kendra had a date for the last dance we went to."

"Yeah, but Brandy made out with her date," said Kendra.

So we spent the rest of the evening laughing like old friends. Fiona decided to just let us relax and give us a break from any lessons. After dinner, mom asked me, "So, I would love to see you model some of your outfits. You look so much better as a black girl than as a white boy."

"Oh mommy," I replied, "There is nothing that I would enjoy more."

"Will you let me do your hair," she asked me?

"Sounds like fun."

"Wait a minute," said Monique, "You girls can't keep Mel all to yourselves."

"Relax dad, you'll get to spend all night with her after we go to bed."

"I was so excited to get to be with your dad as Monique," said Mom. "I missed him so much."

I was literally bouncing up and down with excitement. Kendra seemed happy to see mom again.

"Come on girls," said Mom, "Lets go spend some time together. You too Julie."

The four of us went up to Kendra's room. This was my first chance to see some of the outfits that she had. I thought that her clothes might be a little bit tight on me but I was sure that they would fit. Kendra and I were about the same height but I was about 10 lbs heavier. Julie went over to the closet and started looking at some of the dresses over there.

"Okay girls," said Mom, "get undressed and lets see what we are working with." Julie turned around and watched. I stripped off my blazer and blouse, revealing my enormous breasts. I was wearing a pink bra and my mom could see the top of my tights over my skirt. "My god Brandy," said Julie, "You are huge. And Kendra is not far behind."

"Yeah," I said as I took off my shoes, "I grew quickly and I didn't need breast forms after a couple of weeks." I took down my skirt.

Julie had stripped down to just her bra and panties. She said, "Wow Kendra, you have some cool clothes in this closet. OMG, she screamed, you have playboy bunny outfits in here!"

"Wow," I said, "I want to be a playboy bunny."

"Do you have sheer black pantyhose, Kendra," asked Julie?

"Of course I do," she replied, "It is in the top drawer."

Julie took off her bra and pulled a longline bra out of Kendra's drawer; that way the straps wouldn't show over the strapless leotard. She put on the bra and then grabbed a pair of sheer hose out of the drawer. She tossed two more pairs of pantyhose over to me and Kendra and told us to put them on. "I can't wait to see how we look as bunnies."

I pulled down my white tights and threw them on the bed, and I was only wearing my pink panties. I had on a kotex underneath. The reason I was wearing Kotex was because Fiona had had me plan my periods a while back and it was my time of the month. Even though of course I couldn't actually have a period I still had to go through the motions.

"OMG," said Julie as she slipped her legs into the tights, "why are you wearing a Kotex?"

"Fiona has me simulate periods," I replied.

"That is crazy," replied Julie. She had her tights up to her thighs and soon she had pulled them up over her panties. It was weird watching my sister dress. Kendra had her hose well on her way.

My mother had stripped down to her lingerie and had picked a lime-green prom dress out of Kendra's closet. She took the balled up white tights that I was wearing and began to pull them on. She got the tights on quickly and efficiently and with one motion slid them all the way up her thighs and straightened the waistband. She stepped into the dress.

"Its easier to put them on when they've already been worn," she said. I thought that my mom and sister looked cute in hose. I noticed my sister's long blond hair and well-formed breasts and thought that I would want to look like her as a white girl. I liked the short-pageboy style cut of her hair.

I got the black pantyhose on and had opted for the black bunny suit. The little leotard had a poufy white little bunny tail. I also had a matching set of ears to wear. I was ready to put it on but mom called me over and had me help her zip up her dress.

Julie had a pink bunny suit and she stepped into it. Then, she went to help Kendra get into her red bunny suit. We all put on our ears and then we went to model in the mirror. I put the feet through the holes of the bunny leotard and wiggled it up over my breasts. Fortuantely my tits were big enough to where I didn't have to worry about my top falling down. My hosed legs looked long and sexy coming out of the bottom holes and my crotch was very smooth. All of us stepped into stripper platform heels that had the effect of pushing up or butts.

"OMG," said Julie, "We are so fine." I had to concur. We al struck poses in the mirror.

"Damn straight," I said. I loved how the leotard molded to my skin and showed off every inch of my curvy physique. "I used to always want to be Hugh Hefner, now I get to be one of his bunnies." I felt like the sexiest girl alive.

"Well Brandy," said Mom, "You looked really pretty doing your little ballet dance the other day."

"You were there for that," I said with some surprise?

"We were sitting behind the mirror at the studio," said mom. "I loved how you looked in your little ballerina outfit."

"Oh mom," I blushed. "I feel like such a pretty girl. My maleness is gone."

Just then, there was a knock at the door. Monique came in wearing a short pink dress and white tights. "My god girls," he said, "I have three cute little playboy bunnies." No one would ever have been able to guess that the three black girls in there really had penises.

"Hey dad, or should I say mom," said Julie flirtatiously.

"I don't know if I like my 18 year old daughter dressing like a porn star," protested Monique.

"Oh dad, we're just having fun."

"Mabye it is just my kotex riding up my butt," said Monique. "Fiona has been really tough on me lately."

"Dad," said Julie, "You are such a pretty woman."

"Oh thank you dear," he said as he gave her a hug.

Mom was spinning around in her little green dress. Julie took her iphone and started snapping some individual and group photos of us in our outfits. "I want to remember my sons as little black girls," said mom.

"Wait a minute," I said, "Dad didn't tell you that we were thinking about staying female."

"Well," said mom, "I could hardly blame you."

"Hey mom," I said, "Do you want to see my costume for the ballet recital."

I ran to my room to get my tights and tutu. It was hard to run in heels so I took small, dainty steps, and I felt my ass sway back and forth. I came back with a garment bag. Quickly, I kicked off my heels and took down my corsetlike bodysuit. Then, I dropped my sheer pantyhose. I took a pair of white tights out of the garment bag and sat down on the side of Kendra's bed to pull them on. I pulled the tights up over my panties and kotex. Embarassingly, I had developed a huge erection since everyone was watching me. The feeling of my male member in tights always did this to me.

"Its all right," said mom, "Its just a natural reaction."

"I wish I didn't have a penis," I said, "It is really like my quivering pussy."

"Brandy has a vagina," taunted Julie.

"I just don't want to make a mess inside of my underwear," I replied.

"Yeah," said Julie, "like those messes you used to make inside of my tights."

"I couldn't help myself."

"Your kotex should sop that up," replied mom. "Thank god Fiona thought ahead. And Julie, stop teasing your sister."

"Fine, Mom."

"It feels like wearing a diaper," I replied.

I got the tights on and then pulled on my leotard. I took out the tutu and stepped into it. Quickly, I slipped on my pink ballet slippers. I always loved the feeling of putting my legs and feet covered in soft cool white tights into dainty, feminine, pink ballerina slippers with little bows. Mom said to me, "Sit down at the vanity and let me do your hair and put in your tiara." Mom brushed my hair into pigtails and put a couple of braids into my "do." Then, she put the little princess tiara onto my head. Mom touched up my makeup and it was great watching my face get prettier and prettier. It felt great sitting there in the pink chair in my leotard and tights, with all of the girly attention being lavished on me.

I stood up and looked into the mirror and saw the gorgeous black ballerina that I had become. "Wow" said Julie, "You are the prettiest black girl I have ever seen." I did some little poses and spun around. A cool breeze blew against my tighted crotch. I loved how the tights made my legs looked long and sexy and my boobs looked really prominent. The leotard and tights assisted with my body's freedom of movement and the tight nylon felt orgasmic. I did little arabesques and pirouettes.

I blew kisses at dad. I was the feminine center of the world. Julie thought it was funny how ruffly my butt was and she would slap my exposed under my tutu. She would take her hand and lift my tutu and play with my little ruffles. I would bend over and show my butt, laughing the whole time. She tickled my crotch a little bit.

I don't know if dad/Monique was happy standing there watching his "son" be feminine. What could he really do. "Well Melanie," said dad, "We have raised three wonderful daughters."

Kendra was still hanging around in her bunny outfit and she said, "Hey mom, can you do my hair like Brandy's?"

As we relaxed and chatted away like girls in our pretty outfits, Fiona came into the room wearing three packages. "Relax," she said, "We are all ladies here."

I had no idea what else Fi could possibly have in store for us. The packages were three small mysterious cardboard boxes. She handed one to me, one to my brother, and one to dad.

"Open them up girls," she said. Our hearts were pounding with anticipation. Dad and Kendra opened up their boxes and looked inside.

I ripped open the box and pulled out what appeared to be a brown pair of panties. I was curious as to what they were actually for. I turned the garment around and saw in the front what appeared to be a feminine looking vagina with a patch of hair. "Oh my god" I thought, "Is this what I actually think it is." I saw the look of shock on dad's face as he saw the realistic pussy. We were going to become complete women. Now we could make love to guys and they would never be able to suspect anything.

"These are vaginal panties, ladies," said Fiona. "This is a completely realistic, functioning vagina with an entry depth of nine inches. If you wear them and stick something up there, it will actually stimulate your male member to duplicate the feeling of a female orgasm. It will feel just like you are having sex or masturbating as a woman. Also, these are designed to let you and force you to sit down to pee." We studied them carefully. I could tell that dad couldn't wait to get his on, but Kendra looked a little nervous. It was provoking some anxiety knowing we were taking another step forwards in our development as females.

"Well ladies," said Fiona, "Get on your pussy panties. You have to wear them all of the time now." Mom and Julie snickered.

Kendra said, "No, I am a boy and I won't wear this."

"Nonsense young lady," said dad, "You are a girl and you will be a girl."

"Oh fine," said Kendra. She took down her red bunny leotard and black tights. She kicked off her stripper platforms and took down her shaper panties to reveal her manhood. Mom helped Kendra get the pussy panties on and straight. When she had them on, Kendra looked like a complete black girl from head to toe. All signs of being a boy were gone, and there was no bulge at the crotch. It was crazy. All she had on still were her bunny ears.

"Oh my god," said Kendra, "I have a pussy."

"We all will have pussies," said Dad. Dad took the pink dress he was wearing off of his shoulders and dropped his tights and panties. He was standing there wearing nothing but a red bra. He took off his old shaper panties and pulled on his pussy panties to make him look like a real woman with a functioning vagina. I pulled my white leotard and tutu off my shoulders and threw the nylon garments on the bed. I shedded my tights, panties, and kotex. Dad helped me get on my vaginal panties and pull them up over my penis.

"Wow, dad," I said, "I'll finally be able to be a real girl. It is like I have a real vagina." I thought about all of those times I had dressed up in my sister's clothes and I had never imagined that one day I would get to be an actual girl, and a black girl nonetheless!"

"Of course sweetie."

Mom helped Kendra get her black tights back on. Kendra stepped back into her corset leotard thingy and looked just like a cute little playboy bunny model. Actually, she could have probably passed for 18. Once Dad was satsified that his new vagina was on satisfactorally, he got his heels, tights, and dress back on. I rolled my tights back up my legs and stepped back into my white leotard and tutu. All signs of our male bulges were gone and it would take a very close examination of our private areas to see that we were really male. By now, our feminine secondary sexual characteristics(wide hips, breasts, voice,) were totally developed. Fiona pronounced that we were finally done with the physical aspect of our transformation to women.

"You girls will be able to make love now," she said.

My dad couldn't wait to try it out and raced to the bathroom to pee sitting down. "It works," he announced.

We spent the rest of the night trying on various outfits. Julie and Fiona took some pictures and videos of us and I am sure that the hidden cameras in the house were having a field day. We all put on a mini-beauty pagent and we had the time of our lives wearing dresses and shaking our hips provocatively. It was a great family reunion.

Julie changed into a pair of white tights and a pink leotard and we practiced some ballet moves together.

A couple hours later, I kept on my white tights but pulled on my Pocohontas leotard so I could show it off to mom. I felt much more comfortable and confident with the vaginal underwear as opposed to my shaper panties, in the sense that I didn't have to worry about my male bulge. Dad was in his pink dress and I asked him to help me put my hair into a ponytail.

"Isn't it great having real girl parts," I asked my dad?

"Of course it is honey," said dad, "We are real women."

"Yes," I said giddly, "real girls. I just love being in tights and leotards and having a vagina."

"That is the truth, sweetie," said dad as he brushed my hair.

"Now now," girls, said mom, "Don't get too sweet during this girly bonding moment. Save him for me."

"Mommy," i said petulantly, "My name is Brandy and I am a teenage black girl."

Not to be outdone, my dad said, "My name is Monique and I am a sexy, voluptuous black woman in her pretty pink dress and white tights."

----

As we were wrapping up the night, I changed into my cheerleading outfit to practice some cheers for mom. I pulled on sheer hose and my cheer briefs and my cheer jumper. I grabbed my pompoms and went through some of my routines.

Mom looked at the package of pantyhose and she said, "I see you girls are getting Brown Sugar hose."

"Yes Mommy," I said coyly. I shook my pompoms in the air and sang, "I'm sexy, I'm cute, I'm popular to boot." I loved how the short skirt of the cheer jumper showed off my sexy legs. Afterwards, I got naughty and pulled on some stockings and lingerie that my dad had. I didn't know if he would object or not but he just turned a blind eye.

############################

Despite appearing to the world and my family as a black woman named Monique, I was thrilled to see my wife and daughter after being away for so long. I was worried that they would laugh at me, but they were so understanding. It felt weird when they first saw me slaving over the stove dressed as a woman but they ran up to greet me like nothing had happened. I was still the same guy underneath. We were just acting out parts in a play. Mel and Julie commented on how pretty I was and all I could do was curtsey and blush. I didn't know how they would take it that I was actually enjoying myself as a female, but they were very compassionate and accepting.

Earlier today I had sat down to watch TV and I had put on a football game, but Fiona disapproved and made me watch soap-operas. Mel promised me that she would support me with whatever "major life decision" I made.

So now I had my vaginal panties on under my tights and panties and I couldn't belive how I could sit down to pee. It was hard to say how these things actually worked but it was 21st century technology. I noticed when I stuck my finger inside I would stroke the underside of my penis.

My "sons" were out there prancing around in dresses and hosiery. I wanted to look good for Mel so I touched up my makeup. This was our first night back together and I wanted it to be special. She looked so pretty in that lime-green dress. I was in my pink-dress with cap-sleeves that I loved. I put on another coat of lipstick and touched up our mascara. Soon it would be time for bed. I made sure that my new vaginal panties were keeping me smooth and in check and I made sure that my tights were straight.

"Monique," said Mel, "I just can't get over your new look."

"Well thank you sweetie," I replied.

"I want you," she said, "Tonight. I have never made love to a woman before."

"But I am still Joe, your husband."

"Face it," she said, "You are Monique."

"We should get the girls to bed."

The girls were sad that this fun night had to come to an end. Brandy had gotten into my lingerie and was wearing a corset, garterbelt,and stockings. Kendra and Julie had respectively pulled on a Pocohontas and Little Mermaid princess leotard and were wearing white tights underneath. Julie went to sleep in the spare bedroom, and my black girls went to their rooms for the night. I had no doubt that they would experiment with their new undergarments.

Melanie took me up to my room. Slowly, she pulled off my pink dress and hung it up in the closet. She pulled down my tights and panties and stuck her finger into my vagina. I stroked my breasts.

"Tell me you don't love being a woman," said Melanie. "I always dreamed about being with a black woman."

"I love it so much," I replied. I felt like I was already ready to orgasm.

Melanie stopped what she was doing and she took off her dress. She was wearing nothing but her white tights. She came over and pulled off my vaginal panties revealing a hard cock. She began to perform some oral movements on me. I moaned.

"I love you as a woman," she said, "Much more so than as a man. You must stay as Monique."

She put some lotion on her hand and began to stroke me. I lay down on the bed with my tights gathered at my knees and just enjoyed it.

"Just let me take care of you tonight," she said. "You're still my manly man deep down. Tonight I will treat you both as a man and as a woman."

She played with me until I was ready to cum. But I wanted to try something different. "Wait," I said, as she stopped with a look of surprise.

I stood up and pulled my vaginal panties back on. I walked over to my dresser and pulled out my black dildo. "Use this," I said.

"Did Fiona give you this?"

"Yes," I said, "Now pleasure me like I am a woman." She stuck the dildo into my pussy and it felt great, like I was being screwed. I had pangs of ecstacy.

After I had been satisfied, Melanie let me use the dildo on her and take her from both the front and the back. Then, I had her use the didlo on me in the rear.

"I like you much more as a woman," said Mel, "So I don't mind doing this new stuff with you. It is much more erotic for me this way."

"Me too," I said.

"I don't think that you are a sissy," she said, "You are just a man doing what he has to do to survive. If that means becoming a black woman, than so be it."

"I'm glad you understand," I said. We both pulled our white tights back on and we cuddled.

"How do you think that the boys will do as girls?"

"Just fine," she said confidently. "They are so feminine and convincing already."

##########################

Meanwhile, I was in my bedroom and I "experimented" with my new vaginal underwear. Fiona was right, these things really worked and I felt just like an actual woman. I took my dildo and stuck it all the way inside of me and pleasured myself repeatedly. I heard moans and bumps all night from the room next door and knew what was going on with dad and mom. So I guess we were one big happy family of girls.

#############################

SORRY ABOUT THE WAIT!!!!

The Challenge Part 009

Author: 

  • TylerD

Audience Rating: 

  • EXPLICIT CONTENT

Publication: 

  • 500 < Short Story < 7500 words

Genre: 

  • Transgender
  • Crossdressing

Character Age: 

  • Teenage or High School
  • College / Twenties
  • Mature / Thirty+

Permission: 

  • Posted by author(s)

I was really damn excited because tonight was the night of the big homecoming dance. Our cheer squad would perform during the football game and we had a jazz dance routine ready for halftime. I had a lilac flower-print dress with cap-sleeves ready to go. I also had matching heels.

The Challenge: Part 9

By Tyler


 

I was really damn excited because tonight was the night of the big homecoming dance. Our cheer squad would perform during the football game and we had a jazz dance routine ready for halftime. I had a lilac flower-print dress with cap-sleeves ready to go. I also had matching heels.

Last night I had booted up my computer and I had come across a site called Only-Opaques.com. I loved looking at the hot models in cute tights, skirts, and stockings and I imagined myself in those outfits. I had called dad in to have a look and we agreed that those were the kinds of girls that we wanted to be.

I came downstairs for breakfast and Dad was modeling his Hooters girl outfit for mom and Julie. Julie thought that it was an absolute riot to see dad shake his butt in those orange shorts. I was wearing a red top and a short black mini-skirt with black tights and high heels. I had put on alot of makeup(perhaps too much,) and I had styled my hair into a Paris Hilton ponytail. I had my cheer uniform in my backpack to change into after school and my dad told me that he would drive up with my dress and I could change in the bathroom after the football game.

"I'm meeting Omar after the football game," I told everyone.

"Aww," said Julie, "Brandy has a date and she is all grown up."

It didn't feel weird at all wearing my new underwear that gave me a very realistic vagina. I assumed my dad and brother were both wearing their vaginal panties. Kendra came downstairs and she looked really cute in a sundress. Still, it felt so natural having functioning female genitalia. I knew that every day I was taking more steps towards becoming a woman and being a boy felt like it was in the distant past. All of us guys took our hormonal spray with our breakfast.

I could feel my body being flooded with the hormonal changes and I knew it would be tough to go back to being a guy if that was what I chose. I felt like a true girl and I never thought of myself as anything but Brandy, a hot teenage black girl. My confidence went through the roof with my vaginal panties, since I no longer had to worry about someone seeing any male bulge or having any sort of "accident." And the underwear looked so natural that it really seemed like my new genitalia was part of me.

Fiona was sort of stepping back and letting us grow as women. We were having plenty of chances to get out on our own(supervised of course) and mingle as women and work on our flirting and socializing skills. We gained confidence every time we went out in pantyhose and a dress and pretended to be black girls, to the point where it was becoming normal and we didn't think about it. It was exciting having mom and Julie here, and we could show off for them just how feminine we were becoming. My mom couldn't get over what awesome hip development I had, and she would comment on how my hips would be perfect for childbearing.

I would spend all of my time thinking about makeup, hair, putting together an outfit, ballet, gossip, boys, more boys, and raising kids. I still thought sexually about girls, so I guess I was bi.
 

***

 
After the schoolday was over, I thought nothing of heading to the girls' locker room to get ready with the cheerleading squad. I felt guys staring at me and my butt as I walked down the hallway. Unfortunately I already had a reputation as a slut, thanks to Leiticia. The other day a boy had followed me into the girls room and had propositioned me for oral sex. I was terrified but I refused him. Fortunately he didn't force the issue. I didn't know if I had enough of my previous male strength to drive him off. I doubt I could have put up much of a fight in heels.

I sauntered into the locker room to get ready and there were 25 girls already in there singing and dancing and taking iPhone videos. It felt weird thinking that the other girls thought of me as just one of them. I had probably been turned into enough of a eunuch for the time being for it not to matter. I could still get it "up" like I had as a boy, since my body had actually been producing more testosterone to counter the estrogen. But emotionally, I felt as a girl and would not make a move on them unless one was a lesbian.

I saw the little whore Leticia in the girls room already changing. She was pulling up her sheer tights and then she was putting her cheer jumper on over her boobs. She adjusted her tights over her coffee legs, and she was wearing a pink thong. I noticed how small but well-formed her breasts were as compared to mine. She was lighter-skinned and thinner than I was, and I actually realized that she was a very attractive girl. I would never guess that she was really a boy if I didn't know any better. She had her hair done up in a cute new bob style. I wondered if her female mentor, a Japanese lady named Hiroki, had equipped her with vaginal panties as well.

I could tell that Leticia was mad at me because I was definitely "beating" her.

I went to my locker and took off my school clothes. I slipped into my new sheer pantyhose and quickly got my cheer jumper on. I made sure to change into my pink sportsbra so my breasts wouldn't bounce too much as I was out there dancing. I had my pom-poms in my bag ready to go. I touched up my makeup and made sure my tights were on straight. Fortunately, my pelvis and butt were too big to stop my hose from falling down on me. I put little blue and white ribbons(school colors) in my hair.

Soon, all 25 girls of the cheer squad were out on the track at the sidelines of the football game. Mom waved to me and I waved back. It was really exciting. Leticia, as a really skinny girl, was a "flyer," and she would be tossed up in the air and form the top of "pyramids." I was only a base and had to content myself(wink wink) with looking up other girl's skirts.

Kendra had already been out with his little junior-miss cheer squad and he had already done his dance. It was so much fun getting to shake my pom-poms and be girly for a crowd. I could see the football players on the sidelines staring at us doing our little dances with our skirts flying in the air.

At halftime, our squad performed the Jazz routine. The dance was very flamboyant and sexual and I could feel the eyes of the guys burning holes in my tights as I pranced around, shaking my booty and my boobs. My little skirt was riding up on me and they could get a clear look at my cheer briefs.

Afterwards, dad commented on how good and girlish I was. I introduced Krystal and some other girls to mom and Julie. I went and got changed into my lilac dress with a flower print, and I kept on my pantyhose. Dad helped me restyle my hair into a very nice updo, and my long hair was now off my shoulders. Mom put a pearl necklace around my neck.

"Dad," I said, "I am so happy you can accept me as a girl."

"It is no problem sweetie," he replied. "I am just sad thinking that one day I will have to give you away."

"Oh dad," I replied.

Omar grabbed my hand and took me inside the school to the dance inside the gymnasium. He gave me a corsage to wear.

We shared a few dances, and Omar said to me, "You are the most beautiful girl I have ever seen." It felt great to be held in his black arms. He held me tightly as we shared a slow dance.

"I'm so glad to be here with you," I replied. And you look great in a suit, by the way.

"So are we dating," he asked?

"I'm not sure," I replied. "I mean, I like you and all."

"I have always wanted a beautiful, busty black girl all for myself."

"Mmmn," I said, "Perhaps I can be your girl."

"What would you say if I wanted to take you, here and now?

"Well," I said, "not here."

"We could sneak off to the bathroom," Omar said.

So we went off to a restroom on the far side of the school. I told Omar to relax and that I would take care of everything. I unzipped his fly and found his male member. But he pushed me away and he dropped my dress off my shoulders, revealing my huge boobs. I turned around and he unhooked my bra.

I had been taught well by Fiona, and I began to stroke his member with my hand, focusing on the underside. He was really enjoying this. I let him stick his member between my boobs and I squeezed him inside my clevage. Then, I began to suck on it; it just looked so tasty.

But then, Omar said, "Stop." He pulled himself out of my mouth and said, "Now we're going to do it my way."

Suddenly I was terrified. He commanded me to take off my dress. I was down to just my pantyhose.

"Drop your pantyhose and panties and bend over," he said with authority.

"No," I replied, "I'm not that kind of girl."

"What do you mean," he said, "Everyone in the school says that you are an anal slut."

"Well they lied," I replied.

"You have got to be kidding me," he said.

"I'm sorry," I said, "I didn't mean to lead you on."

"Well," he said, "I won't disrespect you. I'll just go back to the dance."

"Its ok sweetie," I said. "I'm just not ready to go 'all the way."'

So embarassingly, I put my bra back on and then my dress. I touched up my makeup and hoped that no one would say anything to me. Dad was back at the dance chaperoning and I wondered if he noticed that I was missing.

I tried to slip back in the room, but dad saw me and asked, "Where the hell were you young lady?"

"Just touching up my makeup," I said.

"For a half an hour," he replied.

"Yes."

"I'm keeping my eye on you young lady."

I stood around for a few minutes, untiI saw Leticia sitting in the corner all by herself. She was in a black minidress with sheer nylons. I wondered why she wasn't with Shane Johnson. I watched her sit by her lonseome for a few minutes, and then I decided that I would go see what was up.

"Hey Leticia," I said, "Do you mind if I sit down."

"What the hell do you want," she said?

"I just was wondering where Shane was," I said.

"Why," she said, "So you can gloat."

"I just wanted to say I was sorry for what I said," I said.

"Well," said Leticia, as he flashed a small smile, "When you told everyone that I was sucking off Mr. Thompson the Algebra teacher, the truth was that I was screwing him. We both got scared and wondered how anyone found out." She crossed her hosed legs so boys couldn't look up her dress.

I said, "I just made that up because you were talking smack about me. I didn't know it was actually true." I was shocked.

"Look," said Leticia, "Let's just forgive eachother. We're both boys struggling to make our way as women. We don't need to fight."

"How is your development going," I asked?

"Hiroki is riding us day and night," said Leticia. "So much to learn. It is harder for me because I have Asperger syndrome."

"Ass-burger syndrome," I said, "What the hell is that?"

"It's a social disorder called Asperger syndrome," he said, "Basically, people who have Aspergers struggle and can't understand social situations or deal with other people. Hiroki also said that boys with Aspergers tend to crosdress and have fetishes. We can't really deal with dating girls, so we develop simpler sexual hangups. Also, boys with Aspergers tend to be nerdier, less tough, and don't feel like they belong as males, so often times we identify more with a female side, and crossdressing comes."

"That sounds really interesting," I said.

"Yeah," said Leticia, "Boys used to pick on me all the time because I was different. I never fit in as a guy. I feel more comfortable as a girl."

"I wonder if I could have Aspergers," I said, "I mean, I never felt like I fit in either."

"Have you always had trouble making eye contact with other people," asked Leticia? "People with Aspergers have trouble looking people in the eye."

"Yes," I said. "I can never look at anyone and I always felt really uncomfortable in social situations, as a man at least."

"You definitely seem more geared to be a woman."

"I feel like I belong more," I said.

"How do you feel about pantyhose," she asked?

"I love them."

"Leotards?

"Nice and tight."

"Ballet?"

"So much fun," I said, "I love prancing around in a leotard and tights. Sorry I beat you out for the slot by the way."

"Its okay," she said, "You are an awesome ballerina."

"Listen," said Leticia said as a slow song was coming on, "Would you like to dance?"

"Of course I would," I said. We got up and shared a slow dance together. Leticia was such a pretty girl and now I began to understand her better. I looked into her deep eyes and wished that she was a real girl.

"You're really pretty Brandy," she said? I bet you were a great looking guy, but you are a totally beautiful girl. No wonder you can't keep the boys away. You look so pretty in ballet.

"You are so sweet to say that," I said.

"I just think it is great how two boys can become women like we have," she said. She then took the lead and spun me in a little circle.

"Is this going where I think it is going," I said.

"Only if you want it to," said Leticia.

"So what actress do you think I look most like," I asked?

"Tyra Banks," she replied, "And I."

"Oh definitely Halle Berry, but with long hair."

"Well," said Leiticia, "I haven't seen Omar around."

"Omar is, how shall we say, Kaput."

"So you're available," she asked?

"Oh most definitely."

We shared four more dances but were sad when the night had to end. A few people had given us strange looks but it didn't really bother us. We were just two girls having the time of our lives.

We snuck out of the gym as the dance was winding down. Leticia said to me, "Can I see your vaginal panties?"

"Of course," I said. We went to the changing room. I pulled my dress and my pantyhose down. Leticia did the same.

"It looks so real," she said.

"You are so feminine," I replied.

"Oh thank you," she said. "That is so nice to hear."

Leticia put a hand on my boob. I felt my lips being pulled into hers. We shared a long, tender kiss.
 

***

 
Fiona told us that after our Saturday ballet class that she would take us to the Dresden Crossdresser's club. This was a support group for local crossdressers and their families. She told us not to worry about anything and that all of the guys there would be very accepting of us. She told us beforehand that some of the "girls" would clearly look like guys in a dress and others looked like convincing women. Of course, we would be the only white guy/black girl family there, execpt for the Jeffersons who would also attend this week. Some of the girls were part of whole families who had chosen to crossdress. I was just really excited to get to hang out with Leticia at what was sure to be an awesome crossdressing convention.

I was eager to meet other men/women and learn some more secrets as to how I could be more feminine and more convincing.

I pulled on a pair of white tights, and I decided on a white sports bra so my enormous rack would stay subdued. I grabbed a lavender leotard with an attached short skirt, and I put a spare leotard and pair of tights in my dance-bag. Instead of tennis shoes, I came down in my black tap-shoes, and I thought that my feet looked really pretty and classy with white tights going into shiny black little shoes. My dance outfit showed off my awesome curvy figure that was the envy of every girl and desire of every guy in school. One girl told me I could have a future as a stripper if I wanted.

In my leotard, with my new panties, I noticed I actually had formed a bit of a camel toe. It was embarassing beacuse my leotard was a little tight, but with the attached skirt it might go unnoticed.

Dad was wearing a black leotard with long sleeves and an attached skirt, and he was wearing red tights underneath. Kendra had on a black leotard with a white skirt and white tights. Mom had pulled on a brown leotard and white tights, and Julie was in a pink leotard with white tights. Before we got to head off the the studio, Fiona called us all into the master bathroom.

So the five of us ladies were standing around wondering what was to come. Fiona joined us wearing a simple black leotard and white tights, and she said to us, "Now that three of you girls have vaginas, I'm going to give you a very quick lesson about Tampons."

Fiona grabbed a big package of Tampax out of the cupboard. She told us all, Melanie and Julie included, to drop our leotards and tights down to our ankles. I took down my leotard, sportsbra, panties, and tights, and revealed my new underwear. Dad and and Kendra did the same and looked like real black girls from head to toe. Melanie and Julie felt ridiculous but they obliged.

Fiona handed me a tampon and showed me the correct way to insert it. Even though we wouldn't have an actual period, she described to us how they work. The five of us all quickly put them in and Fiona told us that we would wear tampons for the next few days. Dad looked funny putting in his tampon, but it was all in fun. It was weird seeing the little string coming out of all of us. Once Fiona was satisfied that we had them in, she had us pull our dancewear back up. Excitedly, we grabbed our dancebags and headed out for the van.

Before we got into the van, dad pulled me aside and said, "Son, I am a bit concerned with some things I have been seeing recently."

"Like what daddy?"

"Well," he said, "You've been acting really promiscuously lately."

"Oh bosh," I replied.

"Look," he said, "I won't interfere, but just be careful."

"I will daddy," I said, "I know how to handle a teenage boy."

"Its just with all of this feminizing stuff," he said, "I don't want to lose you."

"Look," I said, "Fiona has us prancing around in stockings and using girlie hygiene products. This is only natural."

"Mabye I'm just getting worried," he said, "I know we are supposed to be women and all. Still, I just wanted to point out that you've been showing some camel toe lately. I don't want you to come off as a slut."

"But daddy," I replied, "You're camel toe is sticking out as much as mine."

"Hey, are you ladies coming or not," yelled Fiona. We hustled off the minivan, tap shoes clicking against the pavement.

"I really think that you girls will enjoy the crossdresser's club," said Fiona. "It is full of guys who are exploring their feminine sides."

I thought about my sexual experience(s) last night and I had been in kind of a daze. Mom and Julie were excited to watch me practice my ballet at the studio with my male partner. I couldn't wait to see Leticia again. I sat in the van and crossed my tighted legs, wanting to hurry up and get there.

I gave Leticia a big hug. She had hurt her ankle that day at school and couldn't dance, but she was just going to hang out. I felt bad for her. She was wearing sheer hose, black heels, a white polka-dot skirt, and a stretchy-black nylon top. We both couldn't wait to go to the crossdressing meeting.

So I was on the dance floor in my leotard and tights, and Amanda commented on how pretty I was. I loved looking in the mirror and seeing black legs in white tights. Of course now, I could talk to Amanda freely and have a perfect female voice come out. It was cool getting to discuss the different types of tutus and tights we would like to wear. Leticia and I would go through the Dancewear catalog and imagine ourselves in the different slutty outfits. Being a girl and a ballerina held a huge fascination for me, and I really wanted to keep up with ballet. I also couldn't wait to get more experience with boys and "go the distance," in my total feminine development. I wanted to be a girl forever and ditch being Mike.

So Johnny, my partner, took me in the first position and it felt great as he led me through the Pas De Deux. He would hold me in his arms, bend me backwards, and flip me up. I was easily the biggest girly girl in the world. Leticia was sitting there, jealous as hell, but what could I do? I am sure it was killing her to see the girl she loved in the arms of a man.

As usual, class went by way too fast and soon we were packed off to the Community Center where the local crossdressing community met every two weeks to discuss their unique lifestyles. We had kept on our ballet outfits since sometimes the crossdressers would practice cheer, ballet, or aerobics routines.

Julie said, "I sure hope no one there thinks that I am really a guy."

"Why don't you pretend to be a boy," I said. "It would be funny as hell."

"That does sound like fun," said Julie, as she straightened her pink leotard and white tights, "I'll say my name is really James."

So we got out of the van on the parking lot and walked towards the door. A bunch of guys were staring at us all in our leotards and tights, but it didn't really bother us. We actually kind of put on a show and shook our butts as we walked towards the door. Dad and I actually kind of liked having guys ogle us. Its not every day you see a bunch of hot girls in sexy dance outfits.

The receptionist informed us that the meeting was in the main gymnasium. We saw a few other well-dressed women in skirt-suits walk in.

We were surprised to find about 45 guys all dressed in dresses, hose, heels, leotards, and other items, all in complete female mode with makeup and hairdo's/wigs. About 30 of the crossdressers made convincing, attractive women, and the others looked like drag-queens. Some guys were there with their wives. All but about 6 were under the age of 25. About 5 were college age guys who dressed up. The rest were kids under the age of 18 who were there with their dads. It was crazy seeing 20 other boys my age who were dressed in tight-tops and low-rider jeans, talking about boys, dance, TWILIGHT, and other girly interests.

Leticia came up to me and said, "Wow girlfriend, isn' this great?"

"It sure is," I replied, "Who thought that something like this could exist?"

Kendra didn't seem too happy to be there. He kind of hid in a corner until a few other boys/girls his age drew him out. Julie went over to a table with name tags and drew a "HELLO, MY NAME IS JAMES" sticker and put it on her leotard.

"So you're now James," I said?

Everyone there complimented us on how we looked in our leotards and tights. Dad had fallen in with the older women and they were sitting around discussing menopause and hot-flashes. Leticia brought me over to a group of teenage girls in dresses.

One blond girl in a flowery dress said to me, "I'm Jane, but I go by John as a boy. This is a wig I put on."

"Well," I said, "You make a very convincing girl."

Just then, a woman went up to the microphone at the podium in the front of the gymnasium. She was about 42 and probably the oldest woman here.

"That's Carl, or Carla," said Nicole/Nick, "She's the founder and president."

"Hello Ladies," said Carla, "Our tap teacher got caught in the rain and won't be here to give the lesson. Unfortunately we won't be changing into our tights and leotards."

There was a collective groan of disappointment.

"Still," she said, "We girls are all here to discuss our unique lifestyles. Fortunately we live in a very tolerant area and many males-to-females from around the world come here to live as they please. We know how great it is to dress up and be feminine, even though most of us live and work as men most of the time. So just have fun and socialize."

Nicole was wearing a green-velvet dress with white tights. She had long brunette hair and reminded me of Anne Hathaway. She had on a gold necklace and red lipstick. "I actually do live full-time as a girl," she said. "My mom decided to punish me for my bad grades and forced me to take ballet lessons until my grades came up. Obviously, one thing led to another and now my days as a boy are over."

"Well," I said, "You look totally amazing. Whoever did you did an awesome job."

"My mother started doing my hair and picking out my clothes," she said. "Dad didn't like it at first but he came around eventually."
 

***

 
Dad was hanging out with the older ladies. One of them, June, began to go on and on about how, "It is our duty as men to be subservient and submissive to our wives or husbands. Living in the 21st century, we have to adapt a submissive role and become homemakers. We have to focus on our appearance and display ourselves as sex-objects. We have to embrace bra's, panties, pantyhose, breast development, and dresses."

"Yes," said Emily, formerly Emil, "I make it my duty to please my wife when she comes home from work. I always have dinner on the table and I am ready to provide sex for her."

My dad said, "How do you guys feel about losing your manhood and adopting the female role?"

"What choice do we have," said Erin? "We are men meant to be women. I don't mind wearing a dress and hosiery and jewelry and looking pretty for my wife. That is the role I accept."

"Yes," said Marissa, a gorgeous fiery Latina in a sky blue dress. "My 'son' Rosa and I began to dress as women and my wife just had to accept it. She was against it at first but nothing was going to stop us." "So what do you do Monique?"

"I work at Hooters," dad blushed. There was a gasp.

"OMG," said Marissa, "That sounds like so much fun wearing orange shorts and pantyhose. I so wish I was you. And you have two such beautiful daughters."

"Well," said dad, "Kendra and Brandy were once my sons. Yep, believe it or not, they were both football players. Now all they think about is boys and ballet."

"You are such a lucky mom to have such well-behaived girls," said Marissa.

"Brandy used to be Mike," dad said as the other ladies giggled.

"How did your sons take becoming women," asked Erin?

"Kendra's been fighting it," said Dad, "But Brandy couldn't be happier. Kendra wants to be a 'manly man,' but she has no chance. Her destiny is as a girl."

"How did you guys get into crossdressing?"

"It just sort of happened one day. Something clicked in our heads and we decided to become women. Now all we do is play dress-up. And my wife couldn't be happier for us."

 

***

 

Meanwhile, I was hanging out with my new "girlfriends." Nicole said, "I first want to be a model, ballet dancer, or an actress. Afterwards, I can't wait to be a mother and marry a wonderful woman or man."

Rosa was a gorgeous Latina girl with big boobs. I had seen her at ballet before but hadn't chanced to talk to her yet. She was wearing a purple leotard and white tights. She said, "My daddy began to dress me up when I was 13, and I just absolutely loved it. Now I love to show my boobs and butt off for the boys. My days as a man are out the window. It as all woman for me." She did a little sassy snap with her fingers.

"But don't any of you want to retain any masculinity," I asked?

"Why," said Katie/Ken, "Being a girl is so much better. You get to wear pretty clothes and everyone admires you. It is much better than wearing boring BOYS clothes every day."

"Yeah," said Jane, "I love the feeling of pantyhose, I could never give it up."

"Don't get me wrong," I said, "I love ballet and getting dolled up for the boys, but I like to feel like a man sometimes too. It is hard to deny what I really am."

"Oh please," said Nicole as she stroked her long, thin, tighted legs, "Anyone can see that you are nothing but a goregous black girl.. Face it, you are just a sex object and a bimbo. Your only role is to be a little airhead who is some eye-candy."

"But what about female-empowerment," I asked?

"That is for real women," said Nicole.

"Are any of you thinking about, you know, becoming real women," I asked?

"Mabye," Jane giggled.

"That is a major life decision," said Katie. "This is just fun for me now."

I then described to them how I was going to dance the lead ballerina role for Sleeping Beauty, and they listened with wide eyes as I told them every detail of my tutu, tights, and my strong male partner who was to lead and caress me.

"I so wish I was you," said Nicole.

"James" ran over to us and said, "OMG, this is so much fun."

Meanwhile, Leticia came over to me and said, "So did you ever want to arrange some alone time?"

"You mean like a date?"

"Yeah."

All of us teen girls had had enough of sitting in a circle and talking, so we got up and practiced some impromptu dance moves. We shook our butts for our dads, who watched their pride and joy sons twirling and gyrating in tight girls' clothes. I am sure that they were so proud, seeing their boys display themselves as sex objects. We laughed and giggled until we cried.

"By the way," I said to Rosa, "You are the most beautiful Latina girl I have ever seen."

"Well thank you," she said. "That is so nice of you to compliment my girlishness."

"I wish I had long legs and well-formed breasts like yours."

"Give it a couple years," she said.
 

***

 
So after an hour or so I was just hanging out and chatting away. I saw a gorgeous Latina woman wearing a blue dress come up to me and introduce herself as Marissa. "I saw you talking to my daughter," she said.

"She is something," I replied, "Very beautiful. You must be a very proud mother."

"I am," she replied. "I just wanted to tell you that you are an incredibly beautiful and convincing Trans-Girl. You should definitely keep it up. You will really be something in a few years. You'll have men lined up at your door."

"OMG," I said, "Thank you so much. I'm still not sure what I am going to do, but it feels good getting valdiation."

"Listen," she said, "I've been working with T-Girls for 5 years, and you have the most potential of any I have seen. Your figure, for one, is amazing, and your face is downright beautiful and perfectly formed for a girl. I could get you into modeling."

"I am absolutely flattered you think so highly of me as a woman."

"Look around you," said Marissa, "You are easily more beautiful than anyone here, even James."

So I was more beautiful than my Prom Queen older sister. Incredible. The shoe was definitely on the other foot.
 

***

 
Spending the afternoon with the other crossdressers had got me asking questions. I went to my dad who was staying up late in the kitchen. He looked so damn pretty and content in his red dress, and he was wearing an apron and white pantyhose. I was still in my ballerina gear.

"Dad," I said, "I was wondering if we could talk?"

"About what, sweetie?"

"Well," I said, "I'm not sure if I want to stay as a girl or not."

"But we already talked about this," he said.

"But the problem is that I am a boy and I just don't think I can handle being a submissive woman like they want me to be. I mean, it is all fun and games now, but I don't know if I can do this for my life."

"Its natural that your old male instincts are coming back," he said, "but how can you think of youself as anything but female, especially after these last two months. I don't think we can ever go back."

"But I don't think I can be a wife or a submissive lover. I can be a schoolgirl just fine and do my makeup, but some of this is too much."

"You can do anything you set your mind to," said dad. "I have no doubt that you will make the right decision. And no one says that you have to date guys. But you are a girl, and you should remain one."

"Oh, and by the way," said Dad, "Fiona says that we're going back to the crossdressing club every week from now on."
 

***

 


To Be Continued.......


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