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The Million Dollars Show - Part 2
🕑 Added 2023-06-23 13:48:22 +0000 UTC"Penelope, every teenage girl I know begs their Moms for pierced ears. You are a girl now and this is what girls do. Don't worry about having holes in your ears, you need pretty earrings now." Mary said she agreed with Mom, I needed earrings. "See how cute mine are, I think you would love to wear these dangling cute earrings sister." "Ok, I guess you know what is best for me and this TV contest. I sure hope this does not hurt." Mary and my Mom looked at each other, giggling saying, "No that wouldn't hurt, only happens once." Not sure why they were laughing. Betty's store does the piercing so we were done in a second.
It was quick. The piercing did hurt but Mom told me to get over it, it's what we girls go through to be pretty. Mom picked out some very feminine earrings but said I would have to wait a day or two before wearing them so that my ears would heal. Now I kept looking at all the other ladies in the store and what they were wearing as earrings.
I asked Mary why I was now so interested in what earrings other ladies were wearing. "It's a girl thing. We all check out what other girls are wearing to see if we are just as fashionable as they are. It's all part of being a girl Penelope." Never had these feelings as a boy, guess it all part of my new life as a girl. Back home both my Mother and Mary could not stop talking about how good I looked. How much fun they had picking out my first bra. I did not understand why they were so excited.
Mary grabbed my hand and said let's go finish your new look with some makeup and we have to polish your nails. No girl should be without makeup and nail polish. We went upstairs and Mary did my makeup and taught me how to polish my nails. I kept looking in the mirror as she did my nails thinking how good I looked with makeup. Plus this top was very feminine with my bra straps showing, I was feeling much different now, not sure how to explain my new feelings, I told Mary.
I got a little nervous when Mary put bright pink glossily lipstick on me. She also put what she called a glossy covering to highlight my lips. I giggled saying, "Are my nails the same color as my lipstick? Is that ok? "Penelope, of course, it's ok. You look fashionable, so sweet. You will get used to all these girly "things," we have so much to teach my new sister." Looking in the mirror, I thought this was too much. Mary knew I was nervous saying, "Don't worry you will get used to lipstick. It took me time too, but this makes your whole look.
You look so so pretty with lipstick." I knew it is what girls do wear flashy-colored lipstick. Just never thought I would be wearing lipstick. Mary changed the subject to talk about tomorrow's shopping trip to the mall to the teen store. "Penelope, this outfit your Mother bought you today is nice, but we have to get you something more your age. The Teen Boutique in the mall is just the place. You and I will have to check it out. You will just love the clothes there.
We were finished as Mary brought out a pair of high heels. "Penelope, your Mom wants you to start wearing these heels at home. You need to get used to wearing these heels and now is a good time to start," Mary said. I love high heels and was so excited to try them on. I remember I use to sneak into my Moms bedroom and try on her heels. I loved it.
After slipping on these heels, I felt so different. Looking in the mirror (which I seem to do a lot now, maybe it's a girl thing) I noticed how tall I was and how it made me stand tall with my shoulders back. "Mary, a couple of days ago you and I were boyfriend and girlfriend, boy and girl. Now look at me. What must you think of me? How can I be your boyfriend now looking like this?
I feel strange doing this. Are you ok with me doing all this girly stuff?"
"Paul, or should I say, Penelope, you are still my boyfriend. Just that you and I are having some fun dressing you up to win some big money. I am enjoying this, I still love you. Plus I find you more attractive standing there in your heels and training bra. For now, you are my sister, remember Mom said I was now your sister. So let's have fun Sis, and show the world what fun sisters can have and win the million dollars too." "Mary you are so sweet. I love you too.
I just hope that I can pull this off and win that money. Just between you and I, I have always dreamed what it would be like to dress up like this. I am excited with your help." "Penelope, I know you do have a very strong feminine side to you and that is what we will bring out in you. You will make a great girl when we are done, but you will have to take our direction and not question your Mom and me.
We know best, after all, we are women!" "Let us go downstairs and show Mom your pretty nails and high heels." Strange, Mary keeps referring to my Mother as her Mother. I think I like having her as my sister or should I say being her sister. Mom was pleased with my makeup and new nails. She even congratulated me on my walk in the heels, pointing out how I should swing my hips more and arms. "Would you girls like to have a sleepover tonight? I think it would be fun if your two sisters have a slumber party.
What do you think girls?" I blurted out, YES and so did Mary. We had dinner and Mom said she would do the dishes and we could go upstairs and get into our nightgowns. Like little kids, Mary and I both ran upstairs and got into our matching pink lace nightgowns. These nightgowns I loved since they had small cups on my chest, making me look more like a girl. Even though I had no breasts. Mary and I stayed in our bedroom all night doing our hair and doing each other makeup in funky colors and such. We were having so much fun.
Mom brought us food and we giggled the night away. We jumped into my queen size bed and I noticed something strange down with my little guy. He was very excited and I think ready to explode. I was embarrassed as I held him. "Penelope, what is wrong, you look worried." "Mary I think my little guy wants you, he is very excited, he might explode. I am so embarrassed.
"Oh Penelope, don't be embarrassed, it's ok, it's natural.
Let's go into the bathroom and get rid of your excitement. That is not good for you, a developing girl, to have that little guy so active." I could not believe we went into the bathroom, she took my panties off me and wrapped them around me as she looked into my eyes saying, "Let your juices out sweetie, you will love the feeling and it will calm you down." With her saying that I exploded. Wow, I thought I was going to heaven, Mary holding my little guy and him releasing me. Mary wiped me up with my soft panties.
Felt so good, I was embarrassed. "Penelope, I think we should listen to what your Mom said, you should be wearing your girdle all the time now even to bed, until those pills get your little guy calmed down. Your girdle will hold him down and not let him explode." It was about a week before we were to leave for California when Mom suggested Mary stays at our house so that we can practice more and for me to bond with my sister. Mary moved in and into my bedroom. I liked that but for some reason, I did not have those girlfriend feelings for her anymore. She seemed to be my sister and we bonded like that.
I asked my Mother why I don't have those male emotions for my girlfriend like before. She told me those pills I am taking are slowing down my male feelings for her. I did feel different now with those pills. But I liked it. Felt calmer and more relaxed. I really knew we were all family now when my Mother, "sister" and I walk around upstairs in our bras and panties getting ready. Has become second nature for us but for me a little strange seeing my Mother in her lingerie. Several times she told me not to be embarrassed; we are all girls now and in the same family.
During the weeks leading up to our trip, I have gone to the beauty salon many times. Real comfortable going there now. All the girls there love me and I have so much fun being pampered there. Mom was right, I could get used to all the attention I am getting as a girl. I have done several "public" outings in several outfits these past couple of weeks. I think Mom was getting me comfortable dressing as a girl out in public. I must say I was good at it and did not cause any attention to myself. Was strange when some boys keep staring me down.
But Mom talked me through that saying that is what happens to pretty girls. When those boys smiled at me, for some reason I smiled back and seem to enjoy the attention. Must be those pills, they work well I thought. Mom and I signed up online for the school in California, the one that changes boys into girls. I was not comfortable at first on their website. How could a school change a person? I did not want to be changed, just needed to cross-dress for a bit to win that money.
We signed up for classes at the school like ballet, sewing classes, how to talk like a girl, how to walk like a girl, and lots of "how-to classes." I guess I need those classes to learn how girls act, Mom said. They even had swimming classes. What does that mean? How can I fit into a girl's bathing suit? I asked Mom how that works. She told me the school has a special belt for me to wear and will make my little guy down there disappear and that I can wear a bikini and no one will know the difference. I will have the perfect shape of a teenage girl.
That was strange. How will they make him disappear? On the school's website, there were many testimonials from what I guess were students. The photos of these girls were unreal. The girls were gorgeous, beautiful. They had the most perfect figures and clearly wanted to show their feminine shapes, beautiful smiles, just perfect looking. Could they do this to me? We started packing for the big trip. Mom would not let me take any of my boy clothes. She even said I would wear a dress and my favorite heels on the plane.
She has cleared my travel as a girl and there should be no problems. That made me nervous. I could not believe all the "stuff" I packed to travel. Between the makeup, hair spray, nail polish, bras, girdles, slips, purses, and shoes, I had two big suitcases. I asked Mom why I needed so many pairs of shoes. "Penelope, we girls love our shoes and we need a special pair for each outfit.
You have to be fashionable now that you are a girl. Takes a lot of work to be pretty, but look how pretty you have become in a short time! the Plane trip Joe our limousine driver picked us up. What a nice service the man said, "Ladies let me take your bags as he opened the door for us to get in the limo. Wow, this was pampering. I had a hard time getting in the back seat with this tight pencil dress on. I watch Mary get in sitting first and then swing her legs tight together.
I got the message and did the same. I was surprised at how relaxed I was walking through security and the airport. I was swinging my purse hearing the click of my high heels having a good old time. Mary even commented on how much fun I was having. "I think my sister is having fun, such a cutie, we will have so much fun on our girl's getaway trip," Mary said. The deal sealer was when the security man said, "Ok ladies you all are next, step right up"! Sounded strange to hear him call me a lady, but I liked it. All went fine, got right through security.
I got nervous when the alarms went off when Mary walked through the scanners. Mary smiled and said to the women agent, "It's my underwire bra dear. I forgot to not wear an underwire bra to the airport, how silly of me." The agent scanned her chest and smiled saying no problem. I was nervous then, do I have an underwire bra on? Mom whispered to me, "Penelope, don't worry sweetie, your bra has no wires, you will not have a problem. Smile you are fine with your training bra." We got on the plane, and all sat together in tight seats.
Mary whispered to me, "Penelope, keep your knees together, legs together, and be ladylike." I got so embarrassed; I quickly close my legs and put my hands on my skirted lap. Looking down I admired my long colorful nails and jewelry Mary gave me to wear. Looked so feminine. I said to Mary why do I have to worry about my legs in these tight seats, no one can look up my dress in front of me now in these tight seats. "Sis, you have to get in the habit of always keeping your legs together now.
You are wearing skirts and we girls don't want boys looking up at our dresses at our lingerie, do we?" "I hear you, Mary, too much to remember." "Don't worry, you are in training now, you will remember this and many other feminine things as time goes on. I have been a girl for 19 years, you have only been a girl for 3 weeks. You are doing fabulous, so sweet! After your training, your demeanor will be second nature, and you will keep your legs together without even thinking, it's just what us girls do!" The flight was fun.
Mary and I sat there painting and polishing our fingernails, something to do to pass the time. Got to thinking how much fun this was, doing our nails, endless girly chatting like two teenage sisters, something I would have never thought would be fun before all this but it was a different kind of fun. This was the first time I used a lady's room in a public area, on the plane. Was strange walking into a bathroom saying, Women.
No one gave me a second look. I looked in the little mirror and a strange thought came over me. I place my hands on the cups of my training bra and thought what would it be like to have real breasts like Mary, my girlfriend. I shook my head changing my thinking and without a second thought, got my comb out of my purse to comb my long hair. I thought that was real girly and I did it without thinking. I even remembered to bring my purse to the lady's room, wow! Maybe I am learning how to be a girl.
We landed and another limo picked us up. Love these guys handling our luggage, they are such pampering, love it. I could get used to being pampered. Our hotel was a two-bedroom with a living room and kitchen since we were going to be here for many weeks. The TV studio is right down the block and Mom said my school is right around the corner. We unpacked and Mom said let's go out for dinner. This was scary now I had no boy's clothes here, nothing. I would be in dresses, bras, girls' clothes now, every day until after the TV show in 4 weeks.
As we were walking out of our hotel room, Mom said, "Penelope, are you missing something dear? You forgot your purse."
"Oh, Mom it's hard to remember all this stuff. How do you do it? I am afraid I will leave my purse behind someplace."
"Don't worry dear, we will help you and you will learn to carry your purse and it will be like second nature to carry your purse. Trust me, your sister and I have done it for years."
The big day came to check into Betty's School for boys who want to be girls. I was scared since I really didn't want to be a girl, just act like one so I could win that money. But Mom knows best so I agreed to check-in for their four-day course.
