The Million Dollars Show - Part 1

ALL STORY LIST | PARTS - PARTS 2 | PART 3 | PART 4 | PART 5 | PART 6 | PART 7 

AUTHOR - MAYA

SUMMARY - It's my dream to be on TV and win a million dollars for Mom, but first I have to "fake out" everyone by pretending to be a girl in order to win. This is something I think I might like in the end.

"Mom, are you kidding me?  Do you want me to go on TV and compete for one million dollars on THAT girly show?  The show we watch where people dress up as girls and try to fake out the others with the audience sending in their votes as to who is the "trick" person?  Really Mom?  "Son, this is a perfect game for you. We can win a million bucks so easily.

You would be a natural at it with my help.  Just think what a million dollars could do for us?"  "Mom tell me how I can win, what do I have to do?"  "Paul, you would go on the TV show, you know with the other three people, like a police line up and the audience would pick who is the "special one" out of the four contestants."  "Ok, Mom, what do I have to do?"  "Paul, you would be on TV and doing all those things we see on that TV show with the other three girls.

You would act out with them, try to blend in with them, to look and be like them so that you could win the money."  So how do I win a million bucks?  The judges and TV audience would be told there is a boy among the four-looking girls; voters would try to pick out the boy in the group.  If the boy (you) doesn't get picked, you win the million dollars. You know how the TV show works.  "What do you mean, three girls and a boy on stage, of course, they can see quickly who the boy is, come on Mom be real!"  "Son, you would be dressed as one of the girls.

You would look and act just like them. You could do this and win us the money."  "What... dress as one of the girls, how, me, how do I do that, I am a boy?"  "Paul, you know how you have told me you wanted to crossdress and you wear a girl's nightgown to bed every night now and you look so darling. You are short, small, and petite. You would make a very cute girl for one million dollars."  "Wow, where did you come up with this crazy idea?  I can't go on TV dressed up as a girl.

I will look like a boy dressed as a girl. Of course, I will stand out with the other three girls and lose the contest. Get real Mom."  "Son, think about all that money. We could have so much fun doing this just you and I together like daughter and Mommy. I think you would love it if you just would give it a try."  "Mom I am meeting Mary at the mall now, I am late. I will think about your crazy crazy idea. Really Mom that idea is way way out there... me being a girl on TV, everyone seeing me. How could that happen?  All my friends would laugh at me."  I met my girlfriend Mary at the mall.

I could not get my Moms idea out of my head. To make things worse, Mary dragged me into Victoria's Secret while she bought some bras and panties. Even though I love going into this girly store, today was different. I saw all those pretty feminine things, thinking I might be wearing them on TV, Wow!  At lunch, Mary commented how nervous I was in VS and was wondering if I was ok. Mind you she knows I wear nightgowns to bed and panties 24/7.

She loves my softer side as she calls it. We really connect in tons of ways.  "Paul, I know of your Mother's idea. She told me and I think you could have so much fun and you could win all that money. You are so sweet; you would make a perfect girl. That is why I love you so much."  Wow, what did she say, I would make a perfect girl?  What is going on here, I thought to myself.  "Mary, do you really think I could dress up and act like a girl enough to fake out a TV audience and look like those three other girls?"

"Yes, you have all the features of a girl and with a little padding here and there and training, you could be the winner, the cutest girl on TV, my winner."  I could not believe my ears; even my girlfriend thought I could be a girl. Now this is getting crazy. I have often thought of cross-dressing, but to have my Mom and girlfriend help me and win a million dollars, and go on TV, Wow. This is too much!  Mary came back to my house and we all had dinner. Obviously talking all the time about this TV show.  Mary wanted to take me upstairs to try some makeup and a wig.

I got so excited I thought I was going to wet my panties. They saw my excitement and grabbed my hand pulling me upstairs.  Mary is a professional makeup artist so she did a really good job on me. When they let me look in the mirror I did look totally different. I could not believe my girly look, that of a sweet soft little girl at least from the neck up.  Both girls giggled saying I looked perfect. The rest of my look is easy, all padding and lacey soft dresses.

Mom was snapping photos and Mary was saying how perfect I looked. I was the million-dollar girl and the winner they kept saying.  Could I do this, could I win the money?  "Mom, do you really think I can pull this off?  "Son with our help you can be the girl I know you always wanted to be. We can do this, we can be rich"!  I looked in the mirror, and I saw a girl, amazing what a wig and makeup can do to a boy I thought.  "Ok, girls let's win the million dollars, but I need your help."  "Oh, son, you got our help 24/7, you will be the daughter I always wanted."  "Ok, Mom let's eat dinner and talk.

How do I get this makeup off now, feels funny?"  "Son, you better get used to wearing makeup, you will be wearing makeup every day, one of the many adventures we women have. Leave it on now and let's go downstairs and celebrate the million dollars.  I felt strange walking around in a wig and makeup.  Mary and Mom went on like it was normal for me.  Mary seemed so excited I was willing to do this, dress as a girl. She was talking about how we need to get started soon so that I become natural in my new feminine world.

Mary can you come over tomorrow around 3pm and we will all start planning Paul's transition and training.  It was late, Mary left and Mom took me upstairs to show me how to remove my makeup.  "Paul before I take off your pretty makeup, slip on your nightgown, and let's see how you look.  Wow, looking in the mirror, in my pink lacy nightgown finished the picture. Maybe I had hopes of becoming the princess my mother says I can become.  "Paul all you need now are some curves, like a pretty bustline and shapely hips.

This will be so easy, so much fun. You will become the most beautiful girl and you will win a million dollars, just look at you now with no practice. You are a natural girl sweetie."  It took forever to take my makeup off. I was thinking this is a lot of work, the time to put on and take off girls' makeup.  "Paul, would you like to leave on your wig, you look so natural in it. Frames your pretty face so nicely."  "No, Mom, my head is spinning and I need to sleep tonight.

Not sure I could handle tonight all this new hair."  "Paul, ok, but soon you will have to get used to sleeping with all your new girly hair, with your wig on. We girls have hair and you will have to get used to it, washing and setting your long hair. Even going to the beauty salon."  This was too much. I crashed on my bed and was out like a light.

I got up early, maybe I was excited, but I went into my mother's bedroom and sat at her makeup table staring at myself. Starring at me thinking how different I looked last night with all the makeup on. Thinking could I really pull this off? Would my friends know me on TV? Could I handle being a girl for the TV show?  "Sweetie, are you thinking about last night, are you wishing you could have your makeup on?" You know you looked so pretty last night, you know we will have so much fun. I can't wait to win all that money!

Shall I put your makeup back on now dear?"  "Mom, not sure, can we just leave the makeup off for now? We have a lot to work out and I want to focus on the plan. I am nervous about all this."  "Ok son, get your shower and come on down for breakfast. We will work it out, and all will be fine. Don't worry your pretty head about all this, that is my job."  Mom was on the phone talking with the producers of the TV show accepting their offer for us to be on their reality show. We had to sign a contract which would be sent overnight mail and we had a short time period to make this work it sounded.  I didn't leave the house today watching the re-runs of this reality show.

All looked fun and easy. Not sure where they came up with doing this girly show or contest, but I was nervous about doing it. But I wanted to win a million dollars, who wouldn't dress up like a girl to win that?  It's like Halloween, just a costume contest, I kept telling myself.  Mary came over at 3pm and we all sat around the kitchen table as Mom laid out her plan.  "Paul you understand you will be on stage with three other girls and you will be the fourth one. You have to look and behave like the other girls. If the judges figure out you are not a girl, you lose.

So, not only do you have to look like a teenage girl, you have to act and play like a girl."  "Mom, what do you mean, 'play like a girl'?"  "Son, you have seen the show, the contestants do different things to add to the show.  "Mom you are freaking me out calling me a girl."  "Paul, you will have to become a girl in all senses of the word. I hope when you walk on stage, on camera you will think you ARE a girl. Your brain MUST think and act like a teenage girl. That is the only way you will pull this off.

You have to walk and talk the girl's life."  "My plan is to fly to California 6-7 weeks before the show. You will need a lot of training and you need to experience being a girl so that you become a girl in all her moves and activities."  "Mom, does that mean I have to dress and act like a girl for all those weeks before the TV show? How can I do that?"  "Paul, you need to get used to being a girl. You have to act and become the princess that every girl wants to be.

Paul, I know you can do this, I see your loving soft side and that is what I love about you so much," Mary said.  "Paul, I would like Mary to come with us to California and help prepare you. She can help with makeup and hair and really be a big help. She will be your big sister."  I looked at Mary, she smiled and was shaking her head yes.  "Plus Paul, I have looked into a school out there that can help train you for a couple of days. Strange as it sounds, there is a school that helps boys become girls. How great is that!"  "Mom, this is all way too much stuff. I have a sister now, I am going to a school that turns boys into girls, and I will have to wear a wig, and a dress for 6-7 weeks?

Wow, my brain is having a hard time with all this."  "Son, I have help for your brain. There are pills that will relax you and give you a softer look at life, like the way us girls see life."  "Wow, then I need those pills. I am having a hard time with all this stuff."  Mary came over to me hugging me whispering in my ear saying, "Sister, we are going to have so much fun, you will win the money with the help of your sister and Mom."  Did she call me her sister?

Wow, I think I need the pills right now.  Mom got real serious looking at me saying, "Paul if we are going to win this money, you have to commit to every bit of training Mary and I will give you. You cannot question us, you must greet all your new girly experiences with excitement. I know you can do this and I think the three of us will have so much fun doing it."  "I know Mom, I will try.

I am 100% committed to making this work. I still find it hard to think I can become a girl in a couple of months, but I will try."  We all group hugged and kissed each other. Seemed so strange hugging both my Mom and my girlfriend together. But then, my girlfriend is now my sister. Wow, this is going to be strange.  "Paul, I think the first thing is to go to Betty's Boutique and get some clothes for our new girl. Even before we leave for California you need to get used to the new clothes we girls wear. Plus we need to pick a girl's name for you."  "Mom do I really need a girls name.

I am not sure I can handle that."  "Paul now is the time, I thought you were ready. How can you be a girl without a girl's name?"  "Ok, how about Sam, you know for Samantha."  "Are you kidding me? You need a feminine name so that the judges will not think twice about that. How about Penelope! I always wanted a daughter named Penelope."  "A little too feminine, but if you think so Mom, Penelope it is"!  "Mary what do you think, do you like that name for your new sister?"  "I love it, Mom.

I think my new sister will love it too!"  "Ok, then Penelope it is, let's go do some shopping. You know us girls love to shop."  "Mom you want to go right now. What about my wig, I can't wear this outside."  "Why not, we will just pull it back and you will look like a boy with long hair."  Let us go girls, I could not believe my girlfriend Mary and my Mother were pulling me out the front door to go to my Mothers' girly store.  Off we went and felt very strange.

Here I was walking into my mother's lingerie store to buy girly lingerie for me. What will these two buy me?  There was Betty with a huge smile. Did she know what was going on? Maybe she liked my head of hair? Oh well, Betty gave me a big hug and said how much fun we were all going to have.  She dragged me into the back room and told me to strip down to my underwear and stand on this machine. I got nervous stripping down and looking at my Mother.

Penelope, take your clothes off, we are all girls here don't be embarrassed sweetie."  Betty got so excited hearing my new name saying, "What a sweet name for you Paul. I just love it, it fits your face beautifully, dear."  I smiled thinking now it's starting with this new name thing. Will I ever get used to that girl's name for me?  Betty got me on the machine, strange machine, I thought.  "Penelope, this machine will measure your body and give us every measurement we need for your new clothes.

Stand up tall, shoulders back, smile dear this is fun."  "Ok, Penelope, we need to get you out of that cotton t-shirt and into your first training bra. I do like your panties. Glad to see you are already wearing your panties.  Let me see if I can get a matching bra for those panties."  Betty was gone as I looked at my mother. "Mom, do I really have to wear a bra, really?"  "Penelope, do girls wear bras? Does your sister here wear a bra?

Do I wear a bra? Then of course you have to wear a bra. Girls wear bras. You will learn to love wearing pretty bras, so much that you will never want to take your bra off. Trust me dear, we know what is best for our new girl."  "Maybe my new girl is dreaming of having big boobies like your sister and wanting to wear a real shapely padded bra. That would be so sweet, but all in due time sweet Penelope, your figure will develop and you WILL be wearing big girl bras, maybe even soon if you are a good girl."  Betty fitted me with the training bra.

Looking down was not much there, no cups. Just some padding and tons of lace.  "Penelope, this pretty bra fits you perfectly. This bra will get you used to wearing your new lingerie. Let me check the straps, so sweet."  Mom this bra feels funny. I think it's too tight I said.  "Sweetie, Betty measured you for your bra. She knows what she is doing. I think your bra is the right size. You are not used to wearing a bra. Bras will be tight since they are there to support your breasts. Soon you will know what this is like to have boobies like your sister and me.

Let's put on your panty girdle now too, that will be really tight but important to hide and control your little guy down there."  "Penelope, I think you know how tight bras should be. I think you have snuck into my bedroom and tried on my bras. Tell me the truth Penelope, have you worn Mommy's bras before?"  I got so red in the face, Mom knew, I looked up with a little smile saying, "Yes, Mom I have tried on your bras before.

Don't yell at me, I just was so fascinated with bras, I just had to try one on. Your bras are so so pretty. Don't yell at me!"  "I am not going to yell at you. I wish you had told me sooner. I think that is very sweet, wanting to wear Mommy's bras. If I would have known I would have bought you your own bras sooner."  Wow, that was a big relief plus she said she would have bought me my own bras?  Wow, I would have loved that.

By the time we were done shopping here, I had 6 training bras, four panty girdles, garters belts, nylons, more nightgowns, full slips, and half slips, I could not keep track of all the lingerie my Mother was buying me.  "Penelope, you already wear panties every day but I think you need new prettier silky panties now. Panties with more lacy, pink, and girly colors and not just those white cotton ones you have been wearing.  I squeezed myself, here my Mother was buying all this pretty underwear for me. Thank you Fantasy TV show!

Next came some blouses and carpi pants, very much for girls, with flowers and lace all over them. The blouse was so thin and tight I could see my bra and told my Mother I did not like that.  "Why do I have to wear such tight clothes? I can hardly move in these clothes. Plus I think my bra and girdle is too tight, something is wrong."  "Sweetie, you will learn us girls love to show off our figures, you know our curves. Tight pretty soft clothes do that for us.

You will get used to your new clothes.  Plus your new bra and girdle should be tight, they are helping to curve your figure. They make you pretty! Remember, this is all new for my girl, take your time and enjoy."  "You look divine Penelope. That blouse fits you perfectly. Showing a little lingerie makes the girl outfit, boys love it, plus you look so so pretty."  Did she say boys love seeing my bra under my blouse? Why would boys be looking at me, I am a boy?

Mom un-did my hair and now looking in the mirror seeing my face and long hair, my training bra under this feminine blouse sent the real signal that I was a girl. She handed me some girly shoes and said these will complete the outfit with the purse she gave me.  This was way too fast. I could hardly stand as Mary grabbed my arm and took me out into the big lingerie store. Strangely, no one gave me a second look. Like I was one of the girls here shopping and no question I was a boy. Wow, maybe I do pass as a girl.

Mom whispered in my ear, "Penelope would you like to have your ears pierced now? I think you need pretty ears like Mommy and Sis. What do you think sweetie?"  "Mom putting holes in my ears is a little too permanent don't you think?"