(This story is completely written and will be posted a chapter at a time.)
I was eleven when my mother encouraged me to let my hair grow longer. She had always been nice to me and bought me colorful clothes. I tried many of the games that other boys liked. I had fun with some, but I didn’t like getting roughed up, and my mother was angry when I got dirty. I was happy that my mother supported me in growing my hair longer, as it wasn’t true for most boys. One thing I was that was not nice was that I was jealous that my three sisters were always treated better than me.
Once when I was helping my mother to fold my sisters’ clothes, she noticed how gentle I was with them. “You know, Scotty, you impress me with how you take care of clothes, even your sisters’. I think you would have looked pretty if you were a girl like your sisters.”
“Mom, sometimes I wish I could wear the pretty things they do. I get so jealous. I’m sorry, I know I shouldn’t be saying those things.” Mom stopped what she was doing and came over and hugged me.
“Your Mommies boy, I should help you sometime. Maybe I should even get you your outfit. How would you like to be pampered like that?”
“Mommy, you know it’s not right for a boy to say yes to anything like that.”
She smiles, “Well then, instead of asking, I’m going to pamper you this weekend. Now I want you to go take a bubble bath using Sheila’s fragrant bath oils and just soak in the tub until I’m ready for you.”
She directed Scotty to Shelia’s bathroom, where he soaked in her tub and could use one of her soft sponges. Scotty was soaking for about ten minutes when Mom came to help him. She was sponging his back, and Scotty told her how nice it felt. She helped wash his legs and used a stone on the balls of my feet to make them nice and smooth. “Wow, Mommy, I thought something like that would hurt.”
She smiled and said, “I’m trying to show you what it is like to be pampered. I hope you appreciate it.”
She asked Scotty to close his eyes as she wanted to spread a cleansing cream on his face and to leave it there for a few minutes. She was ready to clean it off when he asked, “You said a minimum of three minutes. Would it be okay if you left it on my face longer?” She did, as she wanted to pamper him.
When she finally peeled off what had become a mask, his face tingled like a cool breeze, causing his complexion to come alive. She had him wash his privates; they both knew that was best. Finally, she was letting the water out, but put some shampoo in Scotty’s hair and helped to work it in and begin to lather. She drew the shower curtain around him and started the shower.
She said, “You be a good girl and stay out from under the shower water until I tell you. I wish we had let your hair start growing earlier than we did.”
He said, “Mom, you just called me a good girl.” She apologized, saying it was that she was trying to pamper me. “That’s okay, Mom, I kind of liked it. You know I get jealous of my sisters.”
She had him rinse out his hair after a while and then used some of Sheila’s conditioner in his hair. Again, mom helped him work it into his scalp and left it for another five minutes. This time, when he rinsed it out, his hair felt rich and thick, looking silky like the sisters.
Soon, the shower was over, and he stepped out of the shower to dry himself off. Mom said, “Wait, I don’t want you to be rough in drying your skin or hair. She used a shorter towel to wrap his hair like he had seen his sisters do. She was patting his skin until it felt it still just a little damp.
“Mom, shouldn’t my skin be very dry?”
She giggled, “Not this time, we don’t want to rob your skin from being moist and soft, do we?” Scotty guessed she knew what she was doing.
She patted his hair until she was able to sweep a styling brush gently through it. She asked, “Now doesn’t that feel better for your hair?” She even used one of those roller-type combs with some heat in it. And then she’d brush it out again. After a little bit of that, she went to using a hair blower and a brush to finish what she was doing. He had a towel wrapped around his body as they walked into Sheila’s room.
There was a pair of panties on the bed and one of Sheila’s undershirts with a little bow, Mom called it a camisole, something. She held the pair of panties for him to step into. When he hesitated, she asked, “Don’t you want me to pamper you like one of your sisters?” He grinned, he thought she’d want him to make a little fuss, he stepped into the panty not wanting to discourage her.
She asked, “Can you be a good boy and push down your penis so it can’t be seen?”
It seemed silly, but it sounded like a neat thing to do. When his mother finally pulled the panty completely up, it gave him a pretty smooth look. “Wow, Mom, that looks cute like my sisters.”
The cami thing felt smooth and soft, besides looking better than an old undershirt. Momma reached for two hangers on the back of the door. One was a pretty pink skirt, which his mother took off and placed on the bed next to him. “Do you think the skirt is pretty?”
“Oh yes, Mommy, are you letting me try it on?” By now she had taken the blouse off its hanger and asked him to put it on before he tried the skirt. “Wow, Mommy, this is pretty, and it looks the right size for me. Thank you!”
He was stepping into the skirt when we heard his sisters come into the house. Mom called out, “We’re up here in Sheila’s room.”
I quickly responded, “Mommy, I’m afraid. They’re going to make fun of me.”
Sheila was soon at her door and knocked, saying, I’m coming in. Mom said, “Yes, but mind your manners.” With that, Sheila stepped into the room, and a surprised look quickly came over her face.
“Oh, mother, why are you dressing him up in our clothes?”
She replied, “He thinks I spoil you two, and he’s jealous. I thought it might be time to pamper him a little and see how he likes it.”
“I understand pampering him; you’ve always bought him colorful clothes, and he appreciates them. But you’re dressing him up like a girl. I’m not sure that is wise.”
Mother says, “Does he look like he’s being hurt? Maybe after he finishes getting dressed, maybe you could help him with makeup if he’s willing.” Mom had finished with the skirt and made sure everything was smooth and properly fit around me.
“Mom, if you’re using a skirt to make him look like a pretty girl, he should be wearing a bra. It doesn’t need to be much, enough to give him a feminine appearance.” She found one of her old lacy bras and had him put it on with the camisole over it.
There was a pair of heeled boots nearby that Sheila saw. Sheila asked Sammy, “Do you want to wear the boots as well?” He hesitated and then finally nodded his head yes. Sheila responded, I have a pair of knee-high stockings that might fit you like a regular pair of stockings. Would you be open to trying them on and seeing how nice you look?” Again, he paused before smiling and nodding yes.
Sheila left and went to Staci’s room. He waited, expecting her to return, and she soon did. She brought the knee-high stockings and her makeup kit. She said, “I gave you time to think, are you still wanting me to help you do this?”
Sure, she had a big smile, he said, “Yes, thank you, unless you think it is stupid of me, then maybe we shouldn’t.”
Sheila sat in a chair across from where Sammy was on her bed. She rolled up both stockings to help start them up his feet and legs. She picked up one foot, placing it on her knee, and started the stocking. She quickly began to smile, “Good, it looks like it will cling nicely to your leg.” She asked him to watch closely as she unrolled it and stretched it up her leg. She had him lift the skirt as it fit under like she said it might.
She started the toes on the second stocking and then asked Scotty to take over. Once done, she helped him with the boots. “Stand up and let’s see how nice they look on you.” She had him turn completely around to get a good look. She asked, “Mom, does that look as cute to you as it does to me?” They agreed and finally asked Scotty what he thought. He was, for once, speechless.
Mom asked, “Is it all right if I take a picture before your sister does your makeup?” He gulped, but agreed; she had to promise not to show the photos to others.
Mom left, and I could hear Staci ask Mom, “Where did Sheila go?”
“She’s helping your brother in her room. Be good if you go in there, and don’t hassle him.”
Staci stepped in and soon said, “Oh my, Sheila, what are you doing to our little brother?”
Sheila turns, saying, “He thinks we’re spoiled because we get to dress up and look pretty. He and Mom started this. I’m just helping things along by doing her makeup.”
Staci asks, “Okay, little sister, what’s your name for looking like this?”
“I think it should start with an ‘S’, but we don’t want a common name.”
We worked our way through many possibilities: Suzanne, Stephanie, Samantha, Shiloh, but it was Sienna that we kept coming back to. “Okay,” he said, “I like Sienna.” And his sisters agreed.
Staci called downstairs, “Mother, we’re calling your new daughter Sienna. How do you like her name?”
We hear Momma coming up the stairs and into my room. “What did you say about a name, Staci?
Staci said, “We chose Sienna. Scotty likes it, don’t you, Sienna?”
Scotty became shy, wondering what his mother would say. We hear her again, “That’s a pretty name, and I think it fits her. Who came up with the name?”
Scotty built a little courage and spoke up, “We came back to it several times, and I was the first to say it was a good choice. Then they agreed, but it will be even better if you agree with us. You’re the one who would have named her if she were a girl.”
(This story is completely written and will be posted a chapter at a time.)
To be Continued…
Extended Experience
Mom’s now back and says, “You’re looking very pretty. Do you like what your sister is doing for you?”
Stacy speaks up, “Momma, she’s looking so pretty that I think we all should be going out to eat tonight.”
Mother asks Sheila, “Are you sure? Do you think she could pass as a girl? I wouldn’t want to embarrass Scotty nor the rest of us.”
Sheila says, and Stacy agrees, “There’s no way anyone is going to see Scotty. I think she’ll enjoy it as we continue to spoil her. Getting a shrimp platter would be a treat for our little sister.”
“That’s not fair to tempt me with that. Momma says I’m not big enough to enjoy that.”
Mother says, “If you agree to eat it and be neat, I’ll agree that we can go out. Mind you, you’re to be Sienna, don’t respond if someone asks where Scotty is.”
Mother doesn’t trust me to stay neat; she sends me with Sheila. My mother, Sheila, and Stacy all need to shower and dress up to go out to dinner. Sheila takes me into her room and sits me at her vanity. “You can imagine and dream, but you’re not to do anything without my approval. Above all, I don’t want you sneaking peeks at me changing clothes.
+^_^+
Sheila is in the shower, talking to Sienna with the bathroom door partly open. She asks, “So how did this start today? Was it your doing this or Mom’s?
“I was helping mom fold some of your clothes, and she noticed how careful and good I was doing. Somehow it came out that I was jealous of you and Stacy, because you get to look pretty, but I can’t. Then Mom said she would pamper me someday. I guess I said I’d like that. One thing led to another, and now you’re helping me.”
Stacy came in and asked, “Don’t you mind that someone may think you’re a sissy?”
Sheila said, “He’s being pampered, he’s not a sissy. The difference is he’s stronger by wanting to do this.”
As Sienna, he says, “I like that I’m being helped, I probably won’t do it more than today, well, maybe another time at the most.”
Stacy was the first ready after me, and then Mom, and last Sheila. Mom takes a picture of us three, and I like how pretty they made me look. Sheila takes a picture of me and my mother.
We go to a nice restaurant that serves fish as well as steaks and chicken. Usually, I have to eat a hamburger or fish and chips, but today I got my choice of the shrimp platters. Sheila ordered the same platter and agreed to show me a neat way to eat my shrimp and sauce. One of the first lessons was not to drown the shrimp in sauce. Like Sheila, Sienna dipped it partway into the sauce, took small bites, and everyone talked as we ate.
Mom was pleased with the many compliments she received about her daughters being pretty and well-behaved girls. I know Stacy and even Sheila thought it was wonderful. I liked the fact that I was passing as one of her daughters.
Mom said, “Your father and Jake will probably be home when we get there or soon after. Your father may not be all happy, but he knows it was my idea and that you look pretty, so don’t be afraid.”
Dad greeted us when we got home, and he shook his head at me, “You’ve always favored your Mom, boy. I guess I shouldn’t be surprised. You do make a pretty girl. If one of your sisters has you tonight, why don’t you sleep in her room? Jake and I will be gone overnight tomorrow. You can continue your fun if you want.” Dad smiled at me before he walked away.
It is Stacy who invites me to sleep in her room; instead of trying to share my room with Jake. She says, “I think we’ll need to check the back of Sheila’s closet to see if she has any nightclothes that might fit you. How would you like that?”
I ask, “Do you think Dad was serious about me continuing this. I didn’t plan on doing that.”
Stacy says, “I’m fairly sure Mom is open to you having a special weekend of you being her pampered daughter.”
We find a simple nylon nightgown with panty, Stacy gives me a fresh, fluffy towel, and sends me into their bathroom to shower. “Make sure you use the hair cap so you don’t wreck your hairdo. Use our bodywash and enjoy yourself.”
Her body wash was fragrant and abundantly lathered over Sienna’s skin. His boyhood got excited about being girly. He got goosebumps covering his arms and shoulders. Stacy had an iTunes player playing I Feel Like a Natural Woman. The first time through, Sienna tried singing but mixed up the words. The longer it played, the better her voice and ability got at singing along.
After becoming dry, she’s given the panty-brief and the long nightshirt. “Make sure you’re wearing one of our robes and watch your legs, keeping them together, and not revealing anything.”
Stacy combs out Sienna’s hair, saying she needs to make sure it holds the curls and its style.
Mom brings a snack for me up to Stacy’s room, “I’m sorry, Honey, but your father is beside himself; I’d rather you not go downstairs. I am very pleased with how pretty and well-behaved you have been today.” She sits and we talk as I eat at Sheila’s vanity. I am distracted by the mirror, seeing a girl looking back at me.
“Mommy, I’m not even wearing makeup, and the girl in the mirror looks attractive.”
Mom compliments me, “Yes, you make a pretty young girl.”
When Mom went back downstairs, I heard her and my father talking loudly. By this time, I was near the top of the stairs, listening. “Jeff, you know Scotty thinks the world of you, but seemingly, you barked at him because he’s not like Jake. I for one don’t think he ever will be; he’s his own person and I think that’s beautiful.”
Dad barked back, “But you caught him in his sister’s clothes and helped him dress up. Why did you do that?”
Mom said, “He wasn’t dressed as a girl until I helped him. Yes, he likes it and I don’t blame him, he’s very pretty as Sienna.”
Dad raises his voice again, “The sissy even has a name? He’s always favored pastel colors and likes the simpler games; I guess it fits him. You’ve babied him too much; see what’s come of it.”
Mother asks, “Did he look bad to you? Don’t you care that he was happy? Even you said he looked good.”
Scotty could see from a shadow that Dad hugged Mother. “Sorry,” he laughs, “We’ve known he and Jake aren’t the same, but this caught me off guard. No, I’m not happy that you have him looking like a girl. But you know I love him anyway.”
“I think Jake and I will go away for the weekend so Scotty can have his time with you. Did you say Sienna is what he’s being called? While I’m not happy with this, I’ll let him/her know it’s okay.”
I head back to Stacy’s room; I get nervous as my Dad takes his time before coming up to the room. Dad’s eyes are back to looking upset before softening, “Sienna, is it? I’m sorry I blew up when I saw you like this. You know it is easier for me to relate to Jake and your sisters. I expect your sisters to look attractive, not you.” He extends his hand for a handshake. “You do make a cute daughter. Mom said you even did well in going out to dinner. Seemingly, you were a big girl getting the platter of shrimp.” He lightly laughed.
“Your brother and I will go someplace for the weekend and let you have some girl time here if that is alright with you?”
“Thanks, Daddy.” I didn’t know where the ‘daddy’ came from, but it fit for me. “I’m sorry that I’m a disappointment. I was helping fold laundry, and it just came out that I was jealous of my sisters. And it isn’t like I can say I don’t like this. Being Sienna is kind of fun.”
I knew my father didn’t like all that I said, but he handled it. Finally, he said, “Come here,” and he hugged me. “I guess our house isn’t immune to having someone different. If this is you, I’ll learn to deal with it.”
Dad left and went downstairs, Stacy came out from the bathroom, and Sheila was soon coming upstairs. Stacy was the first, “I can’t believe it, little brother. That was more than I expected from my father.” She and Sheila both hugged me, knowing I was shaken more than I admitted.
What they might not have known was, I was also shaken by how much I liked being Sienna. I was afraid I’d want to do it more. What if Dad became angry, or if Mom thought I should stop?
My mother comes, “I now think if you can be a good girl and put a robe on. It would be cute to have you come downstairs and visit with us.” She asks, “Would you mind changing panties and putting on this one that is frilly?” It would be covered by Sienna’s nightgown as well as the robe given to her.
“It feels so frilly, and I feel more like a sissy. I’m so tickled that I can show myself off. I want to go hopping down the stairs.
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Jake stares at me as I come down the stairs, and he asks, “Bro, do you like looking pretty like that?” I thought he might be angry, but I took it as a positive comment.
Using my voice for Sienna, I ask, “Do you think I look pretty?”
He smiles, “Yes, for being a sister.” He responds by giving me a hug that caught me by surprise. Sheila said, “She was even wearing makeup and a pretty outfit when we went out.”
Mom hands me her tablet that is playing the ‘Little Mermaid’. I sit and watch it as they’re talking and watching an NCIS episode. It was around 10:oo when I was getting sleepy. I kissed Mom and hugged my Dad, and then Stacy walked me upstairs.
Stacy put little dots of moisturizer onto my face and had me work them into my skin. I was in bed when Mom came to tuck me in. “You had a big day for a girl’s first day. I hope you are happy with all we did?”
“Thanks, Mommy. Is it true that we might do more of this tomorrow?”
Mother has the biggest smile I remember seeing, “I think that would be good for you to be pampered. It is even more than I do with your sisters most of the time.”
Mom left, and Stacy stayed in her room and visited with others on her tablet and phone as I fell asleep.
Sienna stayed awake for a while listening to Stacy brag about how girly he was today. “Monica, you would not believe how precious she looked. She was comfortable being girly… No, sorry. I wasn’t talking about my sister, but my brother. This weekend, mom is pampering him as a beautiful girl.”
Sienna fell asleep and dreamed about the way Stacy was talking about her as a girl. She remembered the girl in the mirror and truly felt she was her. Part of me was afraid it was a dream, but it was a lovely dream, and I prayed it was true. I woke at 4:30 in the morning and was very happy to find myself in the nightgown. I enjoyed sitting down to pee and putting myself back together. I walked down the stairs quietly, not to disturb anyone.
Stacy came to find me when I didn’t return to her room. She hugged me, “Sienna, are you okay?” She escorted me upstairs and had me sleeping next to her in her bed.
It was after 7:00 when I woke again, and she was already getting dressed. She smiles at me. “I’ve put a dress out for you and some accessories that are needed. I hope you like them. I will see you downstairs when you’re ready.”
Mom was soon up to our room, and she had me take a quick shower. Once I’m back out, Momma has replaced Stacy’s clothes with a short dress and a frilly blouse. There are petticoats and stockings as well. Mother tells me that we’ll have breakfast before I get dressed, but she wants me to look pretty enough for pictures.
Momma asks, “Sienna, what would you say about raising money for needy children? I saw a poster the other day for a pageant for boys dressed as pretty girls. It will be in Springfield in another month. I know you haven’t been in a pageant or even dressed long as a girl, so this could be good. It is close, and it’s for boys in junior high or middle school.”
Sheila says, “Mother dressing him up once is one thing, but you’d consider having him in a pageant looking like a girl?”
Mom asks, “Look at her, don’t you think she’d be pretty enough. Look at her legs and complexion; with the right makeup, she’d make a beautiful girl. Sienna, do you like being pampered like a pretty girl?”
To be Continued…
A Beauty Pageant for Young Teen Boys
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
Sienna didn’t want the pampering to stop yet; however, a pageant and being in front of others were scary. She asked, “Momma, Sheila’s important to me, I don’t want to embarrass her or Stacy.”
Sheila says, “Scotty, it’s been unusual, Scotty, to see you as a girl. I don’t think you could ever embarrass Stacy or me if it is over in Springfield, Illinois.”
She said, “I would like to try wearing petticoats under a beautiful dress. I’ve seen both of you wearing them. I think I’d like wearing them with a party dress.”
Mom said, “I was thinking the same thing. How would you like to go shopping for petticoats and dresses today? Did you know this pageant is only open to boys with their parents' approval and supervision?”
“But Mommy, others would be seeing me.”
Mother smiles, “You’ll need to get used to others seeing you being a beautiful girl. You can’t help the needy boys and girls if you’re not in the pageant.”
Sheila asks, “Mother, couldn’t we just measure him and go buy the petticoats and a pretty dress?”
“Sienna, do you want to look as pretty as you can?” Sheila asked.
Sienna surprised herself, saying, “I’ll cooperate, Mommy. Will I be able to get some frilly panties? I’d like a dress that I could wear at home, would that be okay?” I’m very glad as I’m making Mommy happy with me. She asked, “Do you think Tiffany will play with me if I dress as another girl?”
Stacy was on the stairs listening when she called me. “Why don’t I help you to pretty up to go shopping with Mother? It will be good to see how Tiffany reacts to playing house with you then.”
Stacy had to go to the bathroom, so Sienna took the opportunity to call Tiffany. She’s eight months and a grade ahead of me and lives two houses away. She often got upset with me, because I wanted her to do what I liked. It was the third ring when Mrs. Hayes answered the phone. I said, “This is Scotty Haynes down the street. Can I talk to Tiffany? I’d like it if we could play later or tomorrow.”
Soon I’m talking to Tiffany, and Tiffany is a little abrupt, “My mother said you wanted to play, what’s up?”
Scotty said, “You usually tire of playing my games. My mother is pampering me by dressing me up like a pretty girl. I thought you might like playing with me then.”
Tiffany giggles at the other end, “You would be willing to dress as a girl to play house with me? That sounds pretty cool. I’m going somewhere with Jessica today, could we do it tomorrow? I could probably play from 1:00 to 5:00, would that be okay?” Sienna agreed, and we soon hung up.
Stacy is back in her room, asking who I called. I was fairly sure she wouldn’t believe me. I told her Tiffany and I are going to play tomorrow. She responds that it would be nice, but she didn’t think it was true.
Stacy found a dress she had when she was my age; it was blue with white stripes. “This should be good for your shopping, as it is easy to change out of. Do you want socks or pantyhose to wear?”
“I haven’t ever worn pantyhose that might be fun,” Scotty said. Stacy brushed out his hair and helped transform him into Sienna with makeup. “It isn’t too much, it just helps you to look more attractive.” Sienna likes that she uses two barrettes to help her hair hold its shape. Sienna saw them as attractive. Stacy lengthens the strap of a purse so Sienna can wear it over her shoulders.
Mommy comes upstairs to help him get ready, and she’s happily surprised that she’s ready. “Oh, you must be excited to go shopping.”
She asks Stacy, “Are you coming along to help your little sister?”
Stacy says, “I wasn’t going to, I’m not sure it is right. If I decide to go, it’s for Scotty’s sake. Let me finish my makeup, and then I’ll be ready.”
An hour later, we were walking across the parking lot and sidewalk to a mall. Once inside, it is the largest mall Sienna has been to.
She was in one large department store where she tried on a pretty outfit, but as they were ready to go to another store, Sienna let her passive voice slip, “I’d like this one, Mommy.”
A saleswoman asks my mother, “Are you forcing him to dress as a girl?”
Sienna spoke up instead, “No, I desired to have my mother pamper me. Don’t you think I make a pretty girl?”
The woman stepped back, “I’m sorry, but are you sure this is your idea?”
She said, “She might even let me be in a pageant for boys who dress as girls. I probably won’t win since I haven’t done it before. But I don’t think it will hurt me.”
A woman said, “I don’t know about not winning, you already look and behave like a pretty girl. I’m sorry that I said anything. I thought of petti-coating my boys, but I never thought they’d like it.” For some reason, she stayed with us and watched my mother and sister helping me. It was I who went and found the frilly panties.
She called her daughter, who was shopping somewhere in the mall.
We were ready to go to another store when the woman asked, “Did you see that beautiful lilac and white dress near the gowns?” She again apologized, “I’m sorry, but it just came to mind and I thought it would look very pretty on you.”
After my mother asked, she guided us over to the gowns, and we soon found the dress she had described. Yes, the lilac and white was like a princess's gown come true. It would go down to my knees. “Mom, could I try it on today?”
We found a medium in youth size. Another saleswoman came over to see if she could help. Mom told her she was just trying it on. She agreed that she should help anyway. Sienna was just about to go into a changing area when a teen girl came over. Her name is Patricia, and her mother, Monica, was the woman with us earlier.
Patti turns to Stacy, “I know you, you are Sheila Haynes' younger sister. I’ve played basketball against you and seen you at chorus competitions. I didn’t know a younger sister was coming up?” Suddenly, she pauses as she recognizes I might be a boy dressed as a girl. “Wow, you look pretty. I hope others aren’t forcing you to do this. Because of the dress, can I ask, are you going to be in one of those pageants?”
Sienna speaks up, “I’m thirteen; do I look like I’m being forced?”
Stacy’s speaking up, “I’m sorry it may look crazy, but she likes being pampered as a girl.”
Patricia smiles, “I suspect the last time I was pampered as a princess, I was eleven. How old are you?”
Her Mom, Monica, asks, “You don’t mind him being pampered as a girl?”
“Mother, he’s crossdressing or transgender, he’s not a sissy.” Patti apologizes to Sienna, and they like each other. “Look, she even has the legs of a pretty girl… I like your smile as well. You seem to enjoy being spoiled.”
Sienna asks, “Stacy, can you help me try this on?”
Patti says, “That’s darling. I can tell Stacy is happy about helping you.” Like Stacy had indicated, the dress I was wearing was easy to take off and hang to the side. There were pieces underneath the top and the petticoats that my sister helped with. She then asked our mother to help with the dress. Spreading it properly over the petticoats took more effort. We needed to open the curtain to get enough space to finish changing into the dress.
While Sienna was in there, Stacy and Mom each found another dress I needed to change into. She was surprised that she needed to change petticoats, as there were differences between them and the dress she had already tried on.
The saleswoman encouraged my mother. “If you want that lilac gown, you might want to purchase it now or at least put a deposit down and set it aside.”
She heard Patti talking to Stacy, “You know that your brother seriously needs a makeover to make her face more dazzling. I bet if she had on a pretty dress, they’d do it here at one of the makeup counters.”
We left with the lilac dress set aside and agreed to be back to have it properly fitted. Mom wanted to leave this store and go looking for normal girl clothes, or at least that is what she said, until we came to Victoria’s. Mom says, “We need you to be properly fitted for a bra.”
Sienna couldn’t believe she was stepping into a Victoria’s Secret shop for her. A sales girl, Rian, showed her to a private fitting room, “Sienna, you are a very attractive young woman. It is my pleasure to help you find you first bra. Your band is 28” and we’re going to say you’re 30” across your cup, we’ll have you wear a padded 28b. Sienna likes the style Rian brought in here. “Would it be okay to find three for you to try on? Would it be okay to find one in pink or another color?”
“Sienna, I can see you’re still nervous; would you please take a good breath and then breathe lightly ten times. Oh, good, you’re precious. It is exciting getting your first bra, isn’t it?” I murmured yes.
She takes a breath, then says, “I appreciate you being so patient with me.” Rian is back with one that she likes the most. It is a 28B is soft pink and has lace along the top and as part of the cups. She has a satin blue camisole to put over her bra so Sienna can go out to show her Mother and Stacy. She can’t believe other girls are looking at her. She’s proud and happy to be showing herself off.
Stacy says, “Sienna, you are absolutely radiant!”
Mother handed her a bag with a short skirt and blouse. “Honey, make sure Rian has the price tags and change into these. You will look so cute.”
Rian was nice, saying, “We’ll sell the camisole at 50% if you’d like. It looks very good on you. You get put together, and your mother and I will take care of the rest.” She didn’t know until she looked into her bag. Mother also bought her the powder blue bra and a set of three panties.
She walked over to her mother at the register, and she said, “Hello, Kara.” Who was behind her in line? Sienna quickly said, “Mother, you said there wouldn’t be anyone here to recognize me.”
That was when Kara saw my mother turn to Sienna and recognize her. Mom said, “Sienna, relax, it happened.”
Kara Hart says, “Mrs. Haynes.” In a softer questioning voice, “Sienna? My mother said I wouldn’t see anyone either.” Kara stares at me in silence, softly saying ‘Sienna?’ She pulls me in for a hug, “I can’t believe it, Scotty, you are so pretty, and the name Sienna fits you. Oh my, Momma, look who this is?”
Dana Hart, her mother, is looking at me. Everyone pays for their merchandise, and we go find a place to talk. Kara says, “I shouldn’t be so surprised. I’ve told others you’d have made a pretty girl. So what happened?” We visit, and Stacy says, “Strangely, two more people are comfortable with my brother the ‘princess’.”
It is 6:30 when they arrive home with more bags of clothes and makeup in the house than she remembers getting. They’re up to her sister’s room, and 90% are laid on the bed to be put away or for the laundry. Downstairs, there are three slim dresses on hangers Mom bought for her. Mother is putting makeup on Sienna's face as she sits for whatever Mom wants to do next. Sheila says, “I’ve watched a few videos today; let me take over.”
Quickly, she uses a concealer to transform her face, like she’s painting on canvas, and then she begins to work magic. The basic makeup is light; around my eyes becomes colorful. She outlines the lips, and there's a tingling; it’s a volumizer.
She’s letting things dry as she thins Sienna’s eyebrows. They were quickly becoming more girlish; Sienna would have screamed, but she liked what she saw. She touches up her eyeliner around her eyes. She brushes out her eyelashes lightly using mascara. She works on the cheeks until they look narrower with higher cheekbones. Sheila fills in her lips, making them slightly darker around the edges, and then they become a luscious red. She makes a light blue above her eyes, with a light shadow across the bottom of her eyes, and a pink glow just above and to the outside. Her eyelashes are dark and longer, as her eyes sparkle. Tissues are pulled from around my neck. She’s encouraged to step into my new outfit, not the new gown and petticoat, but special nonetheless. Mom takes pictures with Sienna and her sisters, and then photos of the mother and Sienna are taken.
Mother was dressed up as we sat on chairs, and she read poems to us.
Sienna is not sure how late it was when she stopped, or much about when her sisters helped her undress or take off the makeup, and take care to moisturize. But Stacy was smiling as she used a triangle sponge to take off the last of the makeup and applied a moisturizer. Sienna stepped into a panty as a pretty nightgown was put over her head and slid down her body.
To be Continued…
Into a Girl’s World
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
Scotty appeared like a young lady, the way he walked down to his mother to say goodnight. “Mommy, this was the best day I’ve ever had. Thanks for pampering me. You've spoiled me so much.” They gave each other a goodnight kiss, and Mother walked him back up to the bed in Stacy’s room. There was a hint of a fragrance and a new pink comforter for him. “I hope you’re not upset with all you chose to buy for me.”
Mom sat down next to him, “You made me happy, young lady. I hope you have pleasant dreams, because we have one more day to pamper you.”
Come Sunday morning, he got up a little earlier than usual at their house, believing he needed to get ready for church. Scotty whispered to Stacy, who was now stirring to wake up. “Stacy, what should I do this morning? It’s Sunday, but mother said there is still a day of pampering?”
“I’m not sure, Scotty,” she says with her half-open eyes. “Put on my robe and go down to the kitchen. Mom needs to be the one to decide.”
Once downstairs, Mom speaks with the cheer of birds at the beginning of a new day. “It is so nice to see you, Sienna. Did you have a restful sleep? We’re going over to the Open Community Church in Highland Park, so dress nicely.”
The service was spirited, the people were warm and kind, and the question was whether I was enjoying myself. Their warm acceptance helped him enjoy being there. I liked that Therese was very nice to me. She’s straight, but her Mom and her friend Sandy were together. Sienna enjoyed worshipping with her sisters and mother. She felt more cheerful than usual.
They stop to eat dinner on the way home, and Sienna gathers it is no accident that Dad and Jake are there. They went to eat together, and Jake and Dad were both on good behavior. Dad’s careful with his comments, so others close by might not hear any concerns. “Sienna, it appears from your mother and sisters that we need to come to terms with you being a pretty girl from time to time. Now, pretty as you can be, word’s likely to get out.”
“Daddy, others aren’t to know it’s just us.”
“You’re already coming out in public here, and your mother says you are open to participating in the beauty pageant over in the Springfield area.”
Stacy says, “She’s invited over to Tiffany’s to play with her as girls. And she met another girl yesterday while we were shopping.”
Jake gave Sienna a hard time, “It even looks like you’re wearing a bra you didn’t have before, little sister.”
Sienna justified it, “I need to get used to it, if I’m going to be in the pageant.”
They were a little late getting back home, but Tiffany must have been looking to see them drive past their house. Sheila had gone to the door to let Tiff in, but there was a surprise. Sheila, “She brought your new friend from yesterday. Kara and Tiffany were already friends?”
Sienna said, “I thought we’d play at your house, Tiffany.”
The good news is Dad and Jake still won’t be home until 6:00 tonight.
She soon tells Tiff and Kara that she needs to change out of her church clothes. She didn’t mean it as an invitation to where she was changing. But they’re volunteering to help her select what to wear next. They’re going through a pile of clothes that were Sheila and Stacy’s. “This is neat, Sienna. I don’t think either of us got to dress up a boy before.”
Tiffany has her top off to show off; she has puffy little breasts, and Kara, a year older, follows to show she has breasts. They’re both wearing bras. When Stacy comes in and the girls quickly cover themselves. “We didn’t expect you here today. Our mother decided on Friday to pamper our brother, and he’s blossoming and is now going to become our little pageant girl next month. He didn’t expect to bump into you, Kara. Somehow, he thought he’d enjoy playing as a girl with Tiffany, but didn’t tell us.”
“Hurry up and turn around, Sienna, and put on a fresh pair of panties,” Stacy tells him. “I think you have a little too much makeup.”
Tiff interrupts, “You already have a pretty wardrobe for her? Can we play dress up and help with her makeup?” Stacy helps take off her makeup and begins again.
Kara says, “You gave her high cheekbones yesterday, and she looked fantastic. Tiff, you have to see it to believe it.”
Tiff barks, “I saw her coming in, she makes an attractive girl.” Tiff and Kara begin redoing their makeup, and well as Sienna’s. “Wow, Sienna, did you get your ears pierced just for this weekend? Oh my, they’re cute. You have such a pretty face; it works well as a girl. Why didn’t we see that in Scotty? I love you as Sienna.” Finally, they were comfortable with the girl they transformed her into. “Mrs. Haynes, do you like how we dressed up Sienna?”
They were downstairs with her mother when the doorbell rang, and Dana Hart, Kara’s Mom, had come to pick up her daughter. “Kara had just come over; I hope it wasn’t too much? They were playing as girls, and things were alright.” She sits and begins talking with my mother.
Mother says, “I went online and I couldn’t believe it when I saw the information about the pageant for junior high boys in Springfield. Half the funds raised are for needy children, though the prize money won’t match the cost of the clothes, makeup, and hair.”
Mom said, “I was just pampering Scotty, and it snowballed. She looked so pretty, I couldn’t get myself to stop. His sisters and now these girls have gotten into playing dress-up with Sienna.
Tiffany’s mother, Cassie, knocks and is soon in and sitting down. Cassie suggested, “If you’re serious about the pageant, maybe we should help with some serious preparation next weekend?” There would be workshops for those planning to be in this year’s pageant.
Tiffany and Kara are excited, “Won’t that be wonderful, Sienna?” There was a pause, or did you want some other girls to help?”
“I, I…” Kara jumps in, “Ivy would be good, let me call her.” Kara’s dialing and Sienna’s trying to stop her, “Ivy, hi. Tiffany and I have been over Scotty Haynes’ making him into a pretty girl, we’re wondering if you could help us next weekend?” …Only Saturday or Sunday? How about both? It has been fun today. We’ll talk to you tomorrow in school, and oh, by the way, don’t tell anyone. …Anna’s with you. I guess if she already knows that works, but no more.”
Kara knows that either Ivy or Anna makes the secret shakier to keep.
Thankfully, everyone left before their father and Jake came home, so Sienna felt safe for the moment.
It wasn’t two minutes, and Jake said, “Mom, Dad was so upset when we first came back…” Dad took over the conversation, “When I saw the Hart lady and her daughter leaving and then Tiffany walking home, I just kept driving. I was so upset that I didn’t trust myself to come in… Well, I guess twinkle-toes, I mean, word about Sienna will be out soon. I can’t promise I won’t burst and cuss, but give me some space. You want him to be a Momma’s girl; I’ll have to accept it.”
Sheila asked, “Where did you two go to amuse yourselves?”
Jake quickly spoke up, “Dad broke down and bought two game tickets at the university in Springfield today, and I got to show some of my gaming stuff off to Dad yesterday. He even sprung for the two games on my device!”
Dad says, “The place we stayed last night even had two posters for your event next month. One receptionist said if you plan to stay there, you need to call now for reservations. She said, Next week will be slim pickings. I was surprised she said it draws a pretty good crowd of people.”
Dad asks, “I can’t say I want to see him dressed as Sienna. Do you have some pictures of her from today?”
Mom asks, “Remember, you’re asking, I don’t want you getting upset. We first went to church, and then girls came and were with Sienna playing dress up.” My sister confessed to doing some of my makeup.
“Damn,” Dad says, “she’s better looking than many of those promotional pictures.” Luckily, Jake had gone to his room.
Her fingernails were still polished, and her hair and makeup were fairly intact. “I hope I don’t have to worry about you being attracted to boys yet?”
Mom says, “Yet? I don’t think we need to worry about that ever.”
Dad says, “But he may need to get used to boys escorting him places. They are sometimes escorted by cheerleaders and other times by young gentlemen their age. One even kissed the winner.”
Sienna was happy that the time was soon over and she was back in Stacy’s room. She was changing and heading to her shower when Sheila asked, “When did you have your accident?”
Sienna told Stacy to mind her own business, but then Stacy asked, “It was when you shuddered, wasn’t it?” Sienna was upset, they knew, but still wouldn’t respond. Stacy thought she handled it well.
Scotty showered and even shampooed his hair; he was happy with how the curls came out. Then he gets his pajamas on and goes downstairs to say goodnight. Jake teased him, “Hey, Scotty, boys don’t need to say goodnight or kiss their mommy. Tiffany and what’s her name better not tell anyone at school. I don’t want people thinking I have a sissy for a brother, do you hear me?”
He heard him, and he hoped the same, but something tells him others will learn.
When he sees mom and dad to say goodnight, he’s asked to sit down. Dad’s the first to speak, “I’m supposed to tell you that I heard you enjoyed your weekend. And I’m happy for that. But when your mom told me about the clothes you bought and the girls being over. Well, I’m thinking we may need to bring you or your brother downstairs to have the guest room.”
Mother says, “I think it should be Sheila or Jake who should come downstairs; they’re the older two.”
Sheila says, “I’d like it to be me, but it needs to be Jake.”
To be Continued…
In Like Quicksand
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
An event, the coming weekend…
=^_^=
Scotty is awake earlier than usual come Monday morning, but even with that, Stacy has beaten him to the bathroom. Instead, he eats breakfast, and then able he uses the bathroom. It is already smelling girly. He doesn’t mind the fragrance any longer as he became accustomed to it over the weekend. What he doesn’t realize is that his school clothes have picked up the fragrance.
His bedroom was cannibalized as his brother raided the room to take most of the good stuff to his new room downstairs. That included a good comforter, their computer, and best games. Jake also took the deodorant, and Scotty had to use an old one of Stacy’s that she didn’t want back. He’s wearing his mint green sweater that he likes with a yellow dress shirt. His hair is in a boy’s ponytail, and because of the weekend, it looks especially nice and well-groomed, not a regular boy.
No, he did not plan to walk to Jefferson Junior High with Tiffany but it happened. “I’m surprised to see you this morning, Scotty. You’re going earlier than usual, I usually don’t see you. I want to thank you again for sharing yesterday with us.” He looks around hoping Kara’s not coming from wherever.
We are two blocks from school when Anna spots us and yells for Tiffany. I try to walk on, but Tiff insists he waits. Instead of being rude, which he wished he had been, he finds himself exchanging pleasantries with Anna. We’re at school with their friends when Anna asks, “Do you have pictures of the dress or outfits from the weekend. I understand two dresses were new?”
Barb and Layla turn and ask, “Tiffany, show us the pictures of the dress and outfits?”
Before she can think, she says, “It wasn’t me.”
Barb looks at Anna, “If this wasn’t Tiffany, Anna who’s dress and outfit were they?”
Anna turns to him, “I’m sorry, Scotty, it just came out! I didn’t mean to tell on you.”
Barb turns to him and he’s blushing crimson red; Barb quickly grabs his hand and takes him away from others. She’s calm, “It was you, she was talking about. Please show me a picture or I’ll tell?”
He began to bring out his phone, Barb says, “I won’t tell, I’m sorry you must be scared?” He shows her the picture of him made up in the petticoated dress.
“Oh, Scotty, you are as pretty as any girl I’ve seen. Thank you.” She hugs him and gives a kiss on his cheek. “Hurry and put that away; we’ll deny seeing it, because no one will believe it. See you at our lunch table.” Barb walks him back to the other girls. And Barb quickly says, “Scotty got the picture, but we can’t show who it is quite yet. Scotty, you shouldn’t be showing the gown; you’ll take the surprise away. But alas, you’re not quite a girl you won’t understand.”
“Tiffany giggles, “Scotty’s not quite a girl that’s funny, but it’s true.”
Barb says to Tiffany, “I’ve asked Scotty to eat with us girls at lunch time. Are you game with us? We need to have the same story. I’m not sure what is going on, but it’s precious and I’m in.” She and Tiffany exchanged information about the Springfield Middle School Pageant.
It is at lunch time that Barb says, ‘The pageant is for Springfield, the county, and the general public.” She turns to me, “You have potential, but also a lot of work ahead of you. How long have you been doing this?”
He’s too embarrassed to say, she wouldn’t believe it, just this weekend. “Tiffany, does her mother know? I mean his mom?” Tiffany and I begin to giggle uncontrollably. “Can you tell me after school, my sister and I should have a go at dressing him up!”
Barb’s in my last class of the day, “I hear it’s Sienna. I’m taking you home and dressing you up. Nothing special, I want to see how good you look as a girl.”
Scotty didn’t know Barb lived some six blocks from him, but we had had gone to different elementary schools. She asks questions as they go to her house, “Is this why you like soft colors. Several of us girls thought something was up when you let your hair grow longer. Was it just this week that your mother allowed your hair to be groomed and styled like this?”
We were at her house sooner than he expected. He said, “I can’t go in there, I need to get home. I’m not supposed to be doing this until the weekend.” Oops, Barb smiles, “No, you don’t? You can call your precious mommy but I have you for an hour. Your mother shouldn’t miss you until 4:30, and then she’d probably call Tiff’s first.”
“Hurry up and get out of your clothes, you can change in my closet.” Her closet is three times bigger than the one Scotty shared with Jake. She throws in a pair of lace panties, a bra and a spaghetti strap chemise. “Find one of my dresses with inch or wider strap or top.”
He’s arguing, debating with her, five minutes have passed and Debbie, her older sister is there. “What’s going on?”
She said, ‘I have a girly boy in there and she’s to be getting on an outfit… That’s it, Scotty, I know you undressed, you better be in a dress. I’m counting five and opening the door. 1, 2, 3, 4.” Ready or not the door opened he had on the panties, bra, and a chemise and held a peach dress in front of him.
Barb and Deb are both said, “Oh my you’re darling.” He lifts the dress in front of him, not knowing it is hiding much. Debbie pulls out a dress with flowers, and unbuttons the back and hands it to him.
He said, “I shouldn’t.” But he put on the dress and walk out of the closet to find a mirror. Barb pushes her vanity chair out for him to sit on.
Barb asks, “Please tell us, what you’re doing?” She reaches for makeup, saying, “I hope this is alright?” She sits across from him, and it is light makeup, but he can see in the mirror as he’s being turned into a pretty girl.
Debbie takes out his ponytail and brushes back in some waves. “Did you dress up this past weekend?” He’s talking to them like it’s a confessional, and they were girlfriends.
Before he changes back, he calls his Mom. She’s worried, “Kara called, she said you are with a girl she only knows as Barb.”
“Mom, I’m at Barb’s and I’m dressed up again.” He really couldn’t remember exactly what happened. “No, Mom, I wasn’t drugged or forced so to speak. She insisted, and I did it. Mom, I like being Sienna.”
Barb says, “If you’re comfortable, put the camera on video and show her.” He didn’t have any inhibition, as he did it.
Mother says, “You’re darling, but you should change and come home.” Deb wants to take me home as he is.
Mom needed ten minutes to get Jake out of the house. Deb Turner drove him home, Barb’s with them, and he’s in a pair of Deb’s strappy sandals. Stacy’s there and she and Deb know each other, more as acquaintances than friends until now.
Stacy tells him he should be wearing stockings. Mom says I look lovely. They’re talking as he leaves to change out of Barb’s clothes into some of his own. The Turners, Stacy, and Mom agree this is not staying a secret. Jake is back, as Barb and Debbie were leaving. Some makeup is still on, and Jake’s saying you’re a girl magnet. How come the sky is not falling?”
Mom pushes him upstairs, “Lose the makeup, your dad will soon be home.” Barb’s chemise is on the floor on the other side of his bed. He quickly folds it and puts it in a drawer. He still has on Barb’s panties. Phone vibrates, Barb texts me to keep her items. She’s sent him a picture.
There’s a tension most of the week, but little more happens than Dad caught him wearing the chemise. Scotty had to put on his regular robe and Dad lectured him. It’s finally, “When this gets out, you’re dealing with this. We won’t have ten lies ready to multiply. I don’t agree with you dressing as a pretty girl, but if that is what you want, I will support you. We won’t be lying to people.”
“Dad, I liked being pampered; I am sorry. And I am interested in doing the pageant, so I can help others. I know it sounds strange to you, but I like the attention I am getting from girls. It is like we are girl friends when I dress up.” His father shakes his head. “I am glad we can talk. It makes it not so scary.”
Dad put his hand on his head and tussled his hair like he does with Jake and now with Sienna. It makes him feel comfortable. But he chuckled when he ran his fingers through his hair to comb it back. “Love, ya Dad.”
Dad says, “Thanks Sienna, I love you as well.” They share hugs and go on with things.
He’s downstairs setting the table for dinner, hoping his sisters will have to do the dishes after dinner. He visits with his Mom as she prepares their meal. She says, “You seem to be in good spirits after talking with your father. I am glad to see that.” We talk, and I feel more like Sienna, though it is Scotty who's showing. She asks about his phone call, and now knows he has Barb’ chemise and a pair of her panties. She snickered, which he took as she was not fully surprised that something had happened.
It was Friday, when more girls than usual were looking at him and turning away if he made eye contact. A girl named Tammi finally asked at recess, “What is happening with you that some are talking like there’s a secret? I know you’re a little girly with your colors, but you’ve changed becoming even more so somehow?”
He was staying away from saying anything when Ivy, asked in her presence, “When did you tell her? I’m the one who wants to know more about your beauty pageant.”
Tammi says, “It’s true, about the pageant at Springfield, then. Is it true that you wear panties part of the time. I didn’t see any panty lines today.”
He was interrupted by his phone ringing, and he could tell by the tone, it was his mother. She’s already talking, “You remember Patricia Holter from last weekend; she called and said there’s a pre-pageant conference that we should be at tomorrow. She said, "If someone wants to be part of your crew team, they should be leaving with us by 7:30 a.m. tomorrow…” Mom’s going on; “Patti’s in as she loves fashion design… Barb can, Kara can’t and Tiff has to check with her mother.”
“Your daddy says he doesn’t like it, but he’s advancing us $2,000 so we don’t look foolish. So plan on going tomorrow and to the general pageant, and I’ve signed us up for the advanced group.” He knows they’re new, but his mom says that fully in is the way to go. He’s been told that the pre-pageant conference is for contestants like you and our help. There are workshops: walking in heels, composure, makeup, hair, feminizing, male-detox, and the list of options continues. I hope, you haven’t got us into more than expected. Tomorrow should be fun but we won’t need to decide things until afterward… I’ve been assured that those not ready to be serious won’t make the first cut.”
He’s ready to leave school when Tiffany and Barb grab hold of me. “Hey, we want you to come with us to the store and then we’ll take you home. We have things to show you.”
To be Continued…
Pageant Workshops
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
An event, the coming weekend…
=^_^=
Scotty was tired, coming to the end of the school day. He didn’t want to walk home, so he agreed to ride with Tiffany and Barb. They drove to a new store out on the highway, Tully’s Shaping. It had huge posters announcing ‘Just for Young Women’. Barb and Tiffany bounce out of the car, and Scotty decides to wait for them. Tiff opens his side door, grabs his hand, and pulls, “We’re here for you, hurry.” Casey, a young saleswoman, smiles at the sight of him being dragged into the store.
Barb calmly asks, “What do you have to bring out the girl in him? He’s, Sienna.”
Casey quietly observes him as she brings a tip of her finger to her lips. “Seriously,” she asks. “Can I ask, Sienna. Can I correctly assume that you did your eyebrows and have worked your eyelashes?” Looking to the others, she says, “You girls go looking around. I'll talk to Sienna alone. Sorry, Sienna, what are you interested in?”
He said, “They were the ones wanting me to come.”
She smiles, “There’s a reason they’re asking me to help you?” She hands me a piece of material no more than 12” long. “Try this skirt and then we can talk.” She points to the changing rooms where he goes without a fuss.
He couldn’t tell if it was two layers thick; it felt so. He took off his pants to try it on. He realized the shoes and socks needed to come off. The material stretches snuggly over my body. When he went back out. Two girls were out there with their mother, who says, “Cute.” Sienna could have died.
He urged her not to touch his hair, but Casey quickly brushed his hair, and Sienna appeared. She takes him over to a mirror. “Now, that brings out the inner you?” Barb and Tiffany see him and giggle. He runs back to the changing room, but Tiff’s encouraging him, “Don’t shy away, it looks cute on you." To Casey, she’ll get it.”
Casey reaches to him, “Here, try this halter top and give me a peek to see it.”
Sienna quickly closed the door, saying no strongly. Sienna wanted to cry, “Why am I so vulnerable to them?” He knows the answer, he likes their attention, and how they helped the girl in him become visible.
Once he changed back, he took the skirt to Casey. “I like it, but I’m not ready for it today.”
Casey smiles and acknowledges what he said. Instead, she asks, “What do you think, would you like the look of this skirt with this blouse?”
“It’s a printed skirt that matches many of the colors of the blouse; it’s attractive.” Casey quickly holds up the red straps of the colorful top and a mint green skirt. There is no way he’d pick the mint green despite its catching his eye.
Casey says, “I’ll tell you what I saw: your eyes went to the pretty mint green shirt. I want you to be one of our customers today. “I’ll give the skirt as a gift if you’ll buy the top.”
Instead of saying no, Casey asks, “How much do you think it costs?”
With Sienna's voice, “I would pay, $19.95. I’m sure it is at least 29 dollars or more.”
Casey says, “Then for $19.95 it’s a deal.” She doesn’t look to him, but walks to the sales register.”
She neatly folds the two and signs Sienna into Tully’s Shaping membership card, ‘Just for Young Women’s' shopping bag. When he hesitates, Barb’s ready to pay for it, but he glares, “I’ll pay for it, despite not intending to buy anything. He used his card, and when Casey asked for his phone number and email, Scotty gave them so they could get going. “Thanks, Sienna; please know if I talked you into it or you don’t like it, and I’ll double your refund.” She gave him a wink. She had Sienna as a customer and charmed Scotty as well.
He waited as Barb and Tiff paid for their purchases, as well as the first skirt Sienna tried on. They made their way out to Barb’s car, but before they could drive away, He asked to see what they bought. They each bought an attractive skirt and blouse, saying they celebrated with me. He giggled as they paid more than he did. Barb had the last laugh as she held up the skirt they bought for him.
They were good to their word and drove him home. Scotty was surprised when Barb turned off her car. They were coming in with him and his mother at the door, asking, “Were you able to get done what you had hoped?” Mother then said, “Why don’t the three of you go and change into your purchases? Sienna, you can use Stacy’s room and show the girls which is Sheila’s, so they can change there.”
He went to his room as he didn’t trust the others not to sneak through the bathroom to see him. He realized he needed to wear his bra to make the top look good. He hears Tiffany ask, “Where are you, Sienna? I wondered if you have and extra pair of no-line panties?”
He called out, “You don’t ask a boy that!”
She said, “That's funny, I was just teasing, but I saw you were wearing a pair in the store.”
He hadn’t realized that the top had spaghetti straps. They looked and felt nice; he felt very girly wearing them. He opened his door to go out, but was pushed back by Tiff and Barb. “You are as pretty as we expected.”
Barb says, “And you’re trying to come out without any makeup on, as we expected.” She looks into his chest of drawers and then a side table to find his makeup kit. She didn’t take long; she changed his complexion with a brush of makeup, lip gloss, and mascara.
He saw in a mirror that his mother was standing behind me. “What would you put on her eyes to go with that blouse?”
“This is light green with the white highlight. The green is always there, just not often used,” says Barb, and she brushes it on.
He looked cute, got excited, and needed to run for the toilet. Fortunately, Sienna got there in time, but it took longer than usual for the boy to clean up and check everything. The lack of material wouldn’t have been very forgiving. Barb begins applauding as she is impressed by how well he looks.
Mom has footie nylons and a pair of Stacy’s shoes with a 2 ½” heel. It was enough as he walked downstairs that Sheila noticed the difference.
Sheila has a suitcase on rollers with her that Scotty had not seen before. She says, “You’re not supposed to know it, but your Daddy bought it for the weekend.”
He turns to his mother, “Mommy, this is getting too much.”
She smiles, “This is what happens when we pamper our girly boy.”
He hoped Barb and Tiffany would leave, but they sat in the living room. Mom says, “You sit and keep them company. I’ll get something refreshing for you girls.”
His legs are as snug as he can get them, and he’s holding the bottom of the skirt as he sits and sweeps the bottom of the skirt with his other hand, scared the skirt could have flown up.
Sheila’s back downstairs, “I put some panties, stockings, and things out on your bed to be packed. I’ll help you when you’re ready.” She stands over him, “You are so cute when you’re shy around your friends. Who picked out the new outfit? Mom told him, "The girls went to get you to buy an outfit.”
He mentions, “Tully’s Shaping, it’s a new store. Casey Hollings sold me the top and gave me the skirt to get me as a customer.”
Sheila teases, “You’re probably her first girly-boy.” She continues, “So are you getting excited about the pre-conference workshops?”
He says, “I barely knew about them.” Everyone’s talking, and he knows he’s supposed to be following their conversations, but he can’t keep up. Seemingly, he said yes to sleeping with the girls, and his mother said ‘no’. He knows he’ll be in the concealor, makeup, hair, feminizing/male-detox, and nail care workshops.
Barb, Tiffany, and Patti are to be here by 7:00 a.m.. Sheila now says she and not Stacy is going with Mom and him.
He’ll take a variety of clothes: dresses, some skirts, and blouses on hangers, while the rest fit nicely into his new suitcase.
He’s awakened at 5:30; Sheila insists he needs to shower, do his nails, and get made up for the day. “I’m going to be in all the workshops, it won’t make any difference?”
Mom says, “That might be right for some, but you need to make a good first impression. Now get your shower in, and let your sisters help you.” Sure enough, by the time he was out of the shower, Stacy and Sheila were both ready to pamper him. It's embarrassing for a younger brother to have his sisters help him dress as a girl.
Sheila insists that he has on a bra, panties, and a camisole before she begins to help with makeup. He tells her, “I’m more comfortable if I’m in girl mode. It is I who put on the first light coat of concealer.”
“There, his sister has begun,” says Sheila. “Let’s not go heavy as we’re not sure what might be coming off, or important in making an impression.”
He does as she suggested, and even how he dresses, not seeking to overcompensate. The others who are coming with them giggle when they see him. “Wow, we like how you’re presenting yourself. This will present a pretty boy to work with.” Patti wants his lips made up a little more with a plumper, and Barb adds a soft pink to his eyeshadow.
They entered the conference center, registered to get their suite of rooms, and then registered for the conference and workshops. Louise, a pageant official, took him, “Please, come with me, sweetie, we want to make sure you’re in the correct group.” His mom waits nearby, “One, we need assurance you are a boy, and two, that you are doing this freely by choice. Do you see yourself as a sissy, or being forced into this by your mother or for the notoriety of it all?”
He says, “I’m not a sissy, nor am I being forced; it’s just that my mother has taken to pampering me and I like it more than I thought. As a girl, I am attracting more girls as friends.” Louise seems pleased with how I see myself. “I’ve not practiced like many of the others. I might not do well, but I would like to see what it is like to be made even prettier and act more girl-like than I have been.”
She casually checked his panties and found his demure boyhood. “Sienna, that will be very pleasing both for your overall appearance as you bring out your feminine side. Each of you girls will become a unique blossom, no one quite like any of the others.” She gives him a loving hug.
He’s brought back to his mother, as Louise talks more to her; he enjoys overhearing, “That he sees himself as a pampered boy is quite cute and refreshing. I find her appearance disarming; she will be seen as very attractive. Even as a novice, I’ll not be surprised if she does well. It will be beneficial to put her through as many workshops, where she will gain experience doing what is being taught. Wearing heels and learning how to impress others will do her well.”
The first unit he’s to take, he thought, would be boring. How can they use an hour talking about using a concealer? While it is painstaking getting an application off, changing looks made each of the times he did it interesting. Scotty had three pictures to show his Mom, and with each application, he couldn’t believe the dramatic change.
While wearing a pretty gown is wonderful, learning to wear a short skirt or dress and maintain ladylike poise and discipline took more poise and discipline. Barb, Patti, and his mother took turns being the encourager and the taskmaster.
To be Continued…
Scotty at School, Sienna at Home
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
An event, the coming weekend…
=^_^=
Tiffany, Barb, and Stacy assured Sienna she was ready to go and that she had eaten. "Your last morsel,” Barb insisted, “You ate clad in a panty and bra.” Sienna would sit for many poses in different outfits. She would get to wear two outfits as she walked down the practice runway. While they said she did well for the first time, it was obvious she needed more practice and experience. She walked, moved as directed, with many flashes, light from phones and cameras pointing at her.
Scotty thought it must have been ten in the evening when things came to a halt. He was surprised it was barely 7:00 in the evening when he was pushed into a shower with a cap protecting her hair.
It was about half an hour later when Sienna walked out of the room as a regular girl. It was their gathering room where Patti and Barb were waiting for her. Mom said, “You did very well, honey, but we want you to stay as Sienna for the full evening.”
There was a buffet for all workshop participants. Sienna was as hungry as a bear, but her hand was gently slapped when she reached for things her mother didn’t approve of. Barb enjoyed showing Sienna her plate, though well chosen, it had many no-nos for her.
They had time between then and nine to have fun and even dance. She saw Billie, one of the boys, taking part in his male attire. He and Jeffrey were two of the more experienced performers there. He insisted that Sienna should take no less than two dance lessons the next day. “You need to move more gracefully, and you’ll need to practice dancing with someone as your partner.”
When she protested about not wanting to be anyone’s sissy, “You’re choosing to be a girl. You not only want to look good, but you also need to come across as if it is something you enjoy doing. Even if it will mean bending over backwards or your partner kissing you.”
Sienna barked back, “Never!”
Billie smiled, “You will come to enjoy it as a special moment.” She didn’t want to hear it, even though she was sure he was right. She muttered under her breath, “Damn, you.” They shared a hug as another boy asked her to dance.
Going back to the suite, she was happy that her day would be over, but found out it was not. Quickly, she had to take off my makeup and get into a pair of teddy bear PJs. Her ‘B cup’ boobs were staying on; her hair was being rolled into large curlers so they would not lose their shape, and she was once again putting on a facial mask for half an hour.
Tiffany and Barb were vying for the most enthusiastic for her first day. “Wow,” said Tiff, “You can’t tell me you haven’t been doing this longer!”
Barb insisted, “It’s obvious she’s new, but she looks natural. If you were this disciplined at school, I bet you’d be an ‘A’ student. The grace and how you progressed just today is amazing.
Mrs. Haynes replied, “I’m happy with how everyone helped her practice. Sienna did well, but you’re the ones behind the scenes who helped her.”
Patti insisted, “You can help, but it will need to be his sisters and me a little older to get this sissy to behave.” Sienna wanted to growl at the word ‘sissy’, but she knew she meant it as a boy behaving as she needed to as Sienna.
Patti hugged her, “I know you don’t necessarily like that expression, but you did well in accepting it. I have all the respect you need in support of doing this.”
The face mask was no sooner peeled off and Patti took her to the bedroom. “Your mother wants me to sleep here and make sure you stay in bed to sleep.” Sienna turned to one side, and Patti changed out of her sight. She enjoyed that Patti was there and that she wasn’t alone. Once, Patti rolled in bed, and one of her hands was on Sienna’s waist, and it stayed there. Come morning light, she moved out from under her touch.
Peeing like a girl and wiping herself was funny, a good funny. Moving around and feeling her small breasts continued the experience.
During the morning, there was a prayer time, and all participants were doubly encouraged to be respectful of others, as well as to cast their anxieties over to someone, so they didn’t stress over things on their own. Her mother walked her through two informal prayers. The term 'Lord', she learns, is used in many faith traditions. For her, it is Jesus, and her mother encourages her to understand that nothing is hidden. She felt silly thinking that God knew about this side of her. Tiffany reminded her that God knows even this side of her. She’s a believer, but it stretches her faith to believe God knows her while she embraces herself as Sienna.
A meditation for a dozen others and her was moving in her mind, was a breeze of wind; she took flight as a butterfly as different winds carried her here and there. There are fragrances like flowers that drift over her, and there are some that she is attracted to. She felt chiffon on her upper body and arms, satin strips from a skirt around her legs. She became sensitized to feeling clothing and its movement. She sighs with a joyful cry as she imagines herself as Sienna. The time ends much too soon, but she finds that it has been three-quarters of an hour. Her mind yells, ‘Not possible!’
Like Billie had mentioned, she would have two times for dancing. One time to be with a partner comes after she puts on heels. If she doesn’t overthink it, dancing comes easier as she feels the front of a shoe land or a heel touch down. Bart, a brother of Billie, is her partner. She’s on guard, as Billie suggested; she was not going to trust him. He kissed her, but she didn’t think badly of it.
A rest time with a protein drink was her mid-afternoon snack. Now, she had on a long skirt to the top of her ankles as she moved in dance-like motions. She’s kicked up her legs, twists and spins as the one leg circles around her. She does several cartwheels that she didn’t know she still had in her repertoire. She bends forward and finds herself doing a forward cartwheel as others are to her right and left. Ms. Jung steps toward her and takes her hand as she lets her arm float. Ms. Jung leads Sienna around the floor, has her spin under her arm without direction, and she falls back to find herself in Bart’s arms once again. He leads her in a circle, around him, and lifts her into the air, and she trusts him. Landing on her right foot, she spins three more times before she stops and leans against him.
People, including Billie, stand and applaud her. She curtsies to the crowd, to Bart, and waves like she has finished a performance. Ms. Jung and Louise will tell her numerous times, ‘You need to practice no less than two hours a day, Sienna. The pageant will be here sooner than you expect. You will wish you had practiced more.’
She is in what they call street clothes as they leave, but it is an outfit borrowed from Barb. Her diet and workout allow her to fit into a smaller size. Mom gave gift cards to Patti, Barb, and Tiff and felt a need to insist they keep them. “Mrs. Haynes, it’s our pleasure, plus you paid for everything else. We volunteered.”
Monday was a teacher-in-service day, so they did not have school. Kara was over, with Barb and Tiffany. It was Sienna’s turn to practice makeup on herself as well as her girlfriends. That she was in a pink bodysuit with a short skirt pleased everyone. It wasn’t until Kara and she were across from each other that Sienna saw her staring at her breasts and realized how she was dressed.
She asked, “Why didn’t someone say something earlier?”
Kara said, “I was going to, but they asked me to watch, because you were just one of the girls today. And that you need to practice doing makeup every day.”
She changed, but they insisted it was to be in an outfit she recently bought. Sienna put on a bra, panties, and another skirt and top. She wanted to change out of wearing her breasts, but Momma said, “You can’t, stay in character, Sienna.”
Her Daddy was upset that dinner came, and she was still dressed as Sienna. Mother said, “It was intentional, as she was around girls all weekend and today. Plus, Scotty needs to become comfortable with you guys seeing him as a girl. There will be plenty of fathers and boys at the pageant, and some of them will be there to spook other girly boys who aren’t ready?”
Her father asked her, “Boy, are you ready to be hassled tomorrow? I know they aren’t supposed to hassle you, but dressing as Scotty won’t hide your changes. They’re going to see through your attempt to look like a normal boy.”
Her expression gets a little sad, “I know, and I don’t like being seen as a sissy, but that won’t stop some from thinking it. I don’t want to say, I’m transgender. I want to be in the pageant. I was even thinking of going to the dance as Sienna in the next town over for the experience this coming weekend.”
Her father looks at the mother, “Why did you put that into his head?”
Mother said, “If I heard it right, it was Kara who told the other girls. It was Barb who asked if we’d mind if Sienna went with them. Sienna didn’t complain, and I said it was her decision.”
Sienna said, “Daddy, that will give me extra hours of dressing up, practicing my makeup, and dancing. They agreed not to tell on me, so I should be fine.”
Sheila speaks up, “Father, if you’re not going to stop him, I’m going to have him practice until he gets sick of it, or Sienna becomes my sister!”
Staci says, “He also needs to be Scotty to compete. However, you making Sienna second nature to him won’t end it. His blood will be tested to make sure he’s a boy and not using hormones.”
Dad says, “It seems, Scotty, that this is a dream that you want to see through. If so, you have my blessing, but I don’t want to lose Scotty. Come here, Sienna, and let me give you a hug and a kiss on your cheek.”
It was second nature; she was already becoming Sienna. “Thanks, Daddy, your love is very important and I don’t take that for granted.”
Dad says, “I am starting to like this side of you. I will be one of your biggest fans by the pageant weekend.”
The next day at school, Scotty had many girls and a few boys encouraging him. Ms. Susan, his language arts teacher, commented on him after class. “I hear you are competing as a young person in a beauty pageant. And I hear you are doing quite well in your preparation. I want you to know I am happy for you, and I’m here if you need another adult friend.”
Suddenly, in Sienna’s voice, she says, “Thanks. That means a lot coming from you.” Scotty hugged her and went to his next class.
Scotty went to Ms. Susan’s classroom at the end of school. She was picking up her things to leave the room when she saw him. “If you’d like to know by name, it is Sienna. It might seem strange, but I’ve come to like being Sienna; it is like another dimension to who I am.”
Ms. Susan Lane asks him to sit down and talk awhile if he wants. Scotty was already comfortable and liked talking to her, but had a shy side in doing so. He asked, “Would you be embarrassed if, as Sienna, I wanted to talk to you as a friend?”
“It would be important for me that your parents are comfortable with me doing so.” Ms. Susan was warm, a great teacher, and her joy for teaching was contagious. Scotty assured her that he would tell his parents.
To be Continued…
Big Sister Takes Interest
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, relinquishes...
Beauty Pageant for Teen Boys as Girls...
An event, the coming weekend…
Scotty was afraid as he left school and saw some boys off the edge of the school’s property. John, one of his friends, came over to him, “I’ll walk with you for a while.” Two girls, Jayne and Bev, joined them, and the other boys called Scotty names, but they soon left them alone.
Scotty said, “Thanks, John.”
John said, “If it’s alright, I’ll walk you all the way.” That didn’t stop Jayne and Bev from having girl talk with Scotty as they walked.
Jayne asked, “Is it true you had to be Sienna all weekend?”
Scotty said, “It wasn’t a punishment; they wanted me to stay in character. It was different in how I behaved wearing a skirt, keeping my makeup and clothes presentable. It was pleasant as time went on.”
John asked, “What if you had to go pee?”
“I have to sit to pee. Whether I sit at a table or in a chair, I have to sit up straight and make it a practice to keep my hands in my lap.”
Once, they were at his house, and he thanked John and the girls; John asked, “Is it true, one of your friends said Sienna might be going to the dance at Mayfield this week? I would go and dance with you if it would help you.”
Scotty, “Sorry, but I’m not saying yes or no to anything like that.”
Jayne asked, “Would that be practicing your dancing and being a girl?”
He thanked them for walking me home. Jayne and Bev, if you come in, you can meet my Mom and learn more about what I’m doing, and you can help us if you’re willing. Other girls have helped me practice; I would be happy to have your help.” Once they were in the house, Sienna told them they needed to stay in the living room while he changed.
Scotty was upset that it always took more time to change over to Sienna. She apologized for them having to wait. Mom was soon home, and at first, she was upset that the girls were over without her permission. “Mom, they walked me home with my friend John, so I didn’t get hurt.”
Jayne spoke, “Mrs. Haynes, there were four boys just off the school property waiting for Scott. We had the time, so we walked with him. John was important and nice. He probably got bored when we started talking like girls. We heard rumors about Scott competing as a girl. We’re impressed that he wants our help if we could.”
Bev says, “It already struck me at school about how well Scotty takes care of his hair, complexion, and nails. We’ve known each other for seven years. I never sensed he was this feminine until recently. It wasn’t really being feminine, but being able to see the possibility.”
Scotty said, “Don’t listen to her, I’m careful to be my regular self at school.
Mom lightly giggles, “Tell me how you hide those pretty legs at school?”
“I wear jeans or dress pants; I don’t wear skirts!”
“Relax,” Bev said, “Your Mom’s teasing you… Mrs. Haynes says he has pretty legs. I was wondering if his beauty contest includes a swimsuit competition?”
“I’m not telling, but Sienna has to ballroom dance with a boy; he gets to wear fancy dresses, and is now able to do his own makeup.” His Mom says. “Would you be willing to listen to her sing for her talent segments?”
“Sienna first sang, You Belong to Me, imitating Taylor Swift, and Bev and Jayne gave her two thumbs up. When she sang Dua Lipa’s Don’t Go Breaking My Heart, Bev giggled, I like that you’re singing one of our songs, but she’s a little sultry for you right now.”
She turns to his Mom, “I think he’s a year away from wanting to touch Dua Lipa’s voice and style. That might be alright with us girls at a sleepover, but not prime time competition.”
He stayed as Scotty except for two hours of practice, after school, through Thursday. Mom says, “I’m proud of you, Sienna, and I don’t know who Dua is, and I wouldn’t be surprised if Sheila sang like her. But I suspect the singer is at least Amy’s age. No, you’re not imitating her.”
Amy had come home from a summer program at college. Amy entered the room, as Sienna sang Dua Lipa’s song, and Amy joked with Sienna, saying, “Until you start getting warm and moist panties, don’t go there.”
Amy asks, “Hey, dearest brother, Sheila told me Sienna might be thinking of going to a high school dance over at Mayfield High School?”
Sienna says, “Yes, but it’s at the community building. They’ll have two bands coming in.”
Amy said, “Mom’s allowing you to go on your own. You’re not even in high school.”
Mom says, “Sheila and Staci are both going to be there with their dates.”
Amy changes the subject and asks, “Does Sienna have the formal gowns she’ll need for the beauty pageant?” Amy turns to her little brother, “When did you learn to sing like some female singers?”
He told her, “Our music teacher told our class last year that boys our age can learn to impersonate female singers. To prove his point, he took three of us under his wings. It was after the fall concert that my ability began to come around. For the Christmas Concert, I sang like Taylor Swift in silhouette, the song was Last Christmas. Singing it in silhouette was the choir director’s compromise to keep the song and me in the concert. Needless to say, the singer’s name was left off the program, and the audience was left guessing.
Mama said, “You shouldn’t sing any of the songs you sang at school.
Mom told him, “Sienna, I want you to go with Amy and allow her to select a dress you can wear in the pageant. You have to like it, but let Amy choose it.”
Mom was sure Scotty would argue with her, but he envied Amy and loved it when she helped me. He dressed as she asked and did everything she told him. She had chosen three satin gowns; each seemed more glamorous than the last one. There was a slit down the left side of two gowns, and Amy knew he was embarrassed. “Sienna, please look at it in terms of fashion and a beauty pageant. The seam will be closed by a series of buttons. And you will determine how sexy you want to look.”
Scotty told her, “I don’t want to look like an attractive girl that way.”
Amy whispered, “You might change your mind.” Even now, as Sienna tried on the dresses. She found that the hunter green gown gave your left leg a pretty look. Sienna swore it was the shimmering stocking. It ended up being the gown Amy chose and Sienna agreed to. She was fitted for the gown and would need to come back to pick it up after the alterations were complete.
Amy and her friend Sidney took Sienna searching for shoes, as well as another panties and a bra set.
Amy took Sienna out to eat before they went home. Her friends Sidney and Collette met them for lunch. She was received as the darling of their affections. Amy had already told them that she would be in the Springfield Beauty Pageant. They were impressed by how her little brother made a beautiful young teen girl.
Sidney encouraged her to order the smaller shrimp platter and to watch her waist. Collette gave her a very nice gift, and when she opened it, she was surprised to see a pretty workout outfit for a girl. It would go well with her pink cross-trainer shoes that Mom had chosen for her. Sienna was informed would be going to their university for a series of ballet workshops. Collette said they should enhance your grace in dancing,
The pampering was now becoming a driven desire to look and be the best girl she could be. During their ride back home, Amy was tickled when she realized it had all become Scotty’s decision, and not something others were forcing upon him.
Amy had been in a county contest in high school. Amy quizzed her about some experiences she would likely have. She encouraged Sienna to make friends of both the other contestants and those watching the pageant. “When you are happy with the others around you, you will look better and be someone the judges are happy to vote for. You will be happier and have made some lasting friends. If you compete next year, you will have that experience behind you.”
Sienna asked, “Do you actually think I will want to compete in another year?”
“I suspect by now you know the contest has a lot to it. Your chances of winning are a long shot. But, you’re still excited. Yes, I think you’ve been bitten by a bug, and love what you’re doing. You’re no dummy, so you must want to learn as much as you can so you will get better and better. Do you want to be a girl?”
Mom was excited when they got home. Mom asked Sienna to model her gown and the black high heels they bought. Shelia and Staci were both upset that they went without them. Amy replied, “It was my turn to help our little sister, don’t be upset.
Sheila peeked to see the gown and insisted on helping Amy. Sheila asked where they bought the gown. She knew it wasn’t from the stores near us. “Was it difficult finding a gown to fit her shape?”
Amy announced, “Sidney, from college, met us. She knew the store had a reputation for having special gowns. It still took some searching, but what do you think about the gown?”
“It looks great, maybe too good for Squirt!” Amy replied. “But, I need to see how it will look on Sienna.”
“Someone's jealous, but you’ll have to wait.” Amy giggled. Amy insisted on looking at Scotty’s inventory of bras and panties. Then she revealed the vanilla satin panty and bra set that they had bought. Sheila noticed not only how attractive they were, but the slender fit of the panties and the lacework of the bra.
The day they were able to pick up the gown, everyone was anxious to see Sienna in the gown. They took enough time that Mom called up; she was anxious and tired of waiting. Once they had her ready, they went downstairs and got Mom and Dad ready to see her come down the stairs.
Sienna said a silent prayer, not to slip going down the stairs. She couldn’t help but see their smiles grow as she made her way down. Mom gasped, “You look so beautiful and have walked down so well.” She takes her hand and leads her into the living room.
Dad said, “I’m glad you modestly have all but three buttons done up. But wouldn’t a contestant have at least one or two more buttons undone?”
That her Daddy wouldn’t demand all those buttons surprised Amy and the sisters.
Mom said, “She looks fifteen or sixteen in that gown.” Amy unbuttoned another one and had her walk toward the dining room and then back. “She now looks like she’s seventeen, maybe eighteen. I think it is too much.”
Her father said, “While I wouldn’t let her go out looking like that, it might just be what’s needed in the pageant. Amy, is that what you’re planning for Sienna?”
Mama asked, “Sienna, would you be comfortable walking down a runway looking like Amy?” Sienna didn’t have to answer.
She was changing to go out to eat with the family, when Mom came in and saw the panties and bra. “Young lady, is that the set of lingerie your sister bought today?”
“Yes, Mom, they’re to die for? Aren’t they sexy?” Mother had her hurry and get a skirt and blouse on. Sienna was going to tell her how it felt wearing them, but decided now was not the time, if ever.
Mom asked, “If this is getting too much for you, maybe we should stop right now.”
“Mom, it’s not too much! It is just that Amy helped me to think more seriously about the pageant. I did not realize all that you women go through. Amy says I need to take a more active role in preparing for the contest. That you are investing too much in funds and time for me not to do more.”
To be Continued…
The Pageant Begins
Mom offers to pamper him...
Two sisters offer to help...
Dad upset, but relinquishes...
Beauty Pageant for Teen Boys as Girls...
Sienna idolizes Amy, likes being a sister…
The Pageant…
=^_^=
Mom said, “It may be true that by doing things for you, you’re not experiencing the joy of it all. You’ll appreciate it if you become more responsible. It may even be better now that you’re in the beauty contest.”
In the coming days, Sienna made an earnest effort to learn what she needed to learn about hairstyling and doing her makeup. Tiffany, as well as Sienna’s sisters, coached her and liked Sienna’s progress.
They were now just a week away from the pageant, and Sienna was getting anxious and thought of not participating. Her Mom said, “You will do no such thing. You are getting the jitters like a bride before her wedding, that’s normal.”
“I know; I would be backing out if I thought this led to my becoming a bride.”
Mother said, “That just gave me an idea. How about a bridal gown for one of your gowns?” Mom thought, “You could use it as a talent and sing 'You Light Up My Life'.”
Amy spoke up, saying, “It might be worth considering if there wasn’t such a rush.”
Tuesday night, they had a gathering of friends and family who were helping with the coming weekend. Sienna had to try on the different outfits to see if everything fitted the same. Her waist had become thinner, making her breasts and hips look pronounced.
Her Father excused himself to check on Jake, her brother, “I’m not needed here, plus I’ll be out in the audience.”
Cassie Hayes, Tiffany’s Mom, and Dana Hart, Cassie’s Mom, were coming as chaperones, and there were adult assistants with her Mom. Ms. Susan Lane, the teacher, had become her voice and diction coach. The girls and the adult women were wound up, speaking a mile a minute.
There were a dozen shots, each with an ounce of wine to toast the adventure.
Half the students at school seemed to know of Scotty’s coming pageant. The teachers who knew were all congratulating her, except Mr. Murphy and Ms. Cratchet.
Thursday afternoon, Sienna enjoyed a salon appointment. She was royally pampered, having her hair styled, eyebrows shaped once more, a manicure, and a pedicure. Ronda her beautician advised her, “You need to see the weekend as fun, or it is going to weigh on you. You will work hard, and it can be tiring; enjoy yourself to keep your spirit joyful. And don’t be surprised if you see yourself as Sienna. This weekend, you are Sienna Haynes. Kiss the boy who’s your chaperone for the last dance.”
Mom, Staci, Amy, and she, Sienna, are one of many families or groups registering to participate in the Springfield Beauty Pageant for Boys. He and twenty-some other boys have to show that we are worthy of our participation. Director Maude Druthers is upfront and communicates, “This Pageant is celebrating seventeen years of recognition, and not everyone will meet the rules and discipline to participate. Among other things, there will be medical checks to verify that you are biologically a boy participating as a girl. You will be judged on charm, deportment, talent, speech, presentation, and congeniality. There will be times when you will be on your own. By this, we mean you will be on your own in doing your makeup and hair. You will select the clothing needed for that portion of the program without the assistance of others unless specified.”
Dr. Kelley Greene had him nervous as she checked to confirm that Sienna was the boy Scotty Haynes. She asked why my breasts filled my B-size bra cups. Having worn a bra so much and eating certain foods, as they were allowed, her flesh had gathered in the cups. The doctor was impressed that Sienna had the workshops and had a regimen of practice more than many of the other boys.
Sienna had time for a salad lunch, found her changing area, and was ready to prove she was worthy to be a participant in the official pageant. Amy encouraged her, reminding her that tomorrow she will have already been on stage, walked the runway in a gown, and spoken on stage, though it had been a smaller crowd. Today, participants only had to gain approval in two of the three areas and show the possibility in a third. I had received an A-plus from the officials. Sienna was now an official entrant in the Springfield Beauty Pageant for Boys.
Out of the twenty boys that started that afternoon, only nine of us gained the needed approval to join the thirty-five who were second or third time participants.
It was nice to have Mother and two sisters in the audience. They were able to take flash pictures and applaud, but were not to be vocal.
Come six p.m. Thursday evening, they needed to rehearse the song and choreography of the opening number, the pageant, and speaking to the MC, introducing herself, answering a simple question, walking the runway, and returning to her place on stage. They were finished and able to return to their rooms by 9:30. The official program would begin at noon on Friday.
Returning to their suite on the fifth floor, the full family and support team were there.
They were backstage getting her outfits and makeup set. The makeup for each presentation. Sammy was walking through in Sienna’s mind what she needed to do. Amy bumped Sienna, “Remember, as you walk through what you’re going to do that you’re a girl here. That with the 3” heels, your feet reach the floor when you are seated.”
Sienna looked to Amy, and Scotty knew that her big sister anticipated and what Sienna needed to do. Scotty, on his own, would have left Sienna mechanically doing the motions. With Amy echoing in her head, it was Sienna who went through the first presentation with the full group of beauty contestants. When it was her turn to meet with the MC, she stepped forward and met with Michelle Turner. Sienna took note of the auditorium. “Ms. Turner, it is awe-inspiring to meet with you before a full house.”
“Sienna, you are a first-time contestant to be a Pageant Princess; what piqued your interest to become a contestant?”
“I’m the youngest and a boy with three sisters. When my mother pampered me to be like them, a new world opened up to me. I loved being pampered, but it opened up a new world that I'm exploring. I like how much I’m learning. I love and respect my Mom, sisters, and girls a whole lot more.”
Michelle, “It looks like you could say more, but it’s time for your first walk down the runway.”
“Thank you, Ms. Turner.” She walked down the runway, waved to the crowd, and made connections with a person here and there. Sienna stopped at the end of the runway and waved. She had a relaxed smile as she waved to the whole crowd. She was enamored there, and it showed.
She was glowing once she was back in her position. Here she was, a boy not hiding, but showing himself off dressed as a girl. Wearing panties, a pretty dress, and makeup, and people cheering, with no judgment or ridicule.
Later, in the first day’s program, she was asked, “Name one of today’s issues and what’s your position on it?”
“I’d try to own my position, but instead of taking a side, I’d try to create a discussion, listening to as many sides as I could. I think society is becoming too divided. Not everyone is happy that I and other young teen boys are dressed as girls. I’ve taken some bumps, been hit, and been called some ugly things. It takes time and effort, and staying the course to gain the respect to be taken seriously. When someone is derogatory in public, I gain the respect and understanding of others.
‘I believe hate groups have gotten too much press, where some have waited too long for simple respect. My sisters shouldn’t need to go an extra mile to prove themselves, but they have, and I’ve learned as a guy, they have so much I can learn from them. My respect is now automatic, where I acknowledge it wasn’t before.”
Sienna sang and played a little piano as her first talent, using Carol King’s version of I Feel Like a Natural Woman. It was an old enough rendition; hopefully got a chance to stand or fall on its own. For the first evening gown, she wore an ivory gown with colored sequins that had three times as many subtle pink and champagne sequins as baby pastel blue sequins. It was her idea to add the sequins, and her teacher, Ms. Susan Lane, not only embraced the idea but also helped her hand-sew them on the skirt of the dress.
Contestants met with judges over the noon meal, and again at dinner at 6:00 p.m. Sienna was talked to at both meals. Her manners and etiquette had been complimented. Judge Stephen Johnson asked, point-blank, “I hear you were to have hand-sewn the sequins for this evening's gown? That will be shared as part of your presentation this evening, but I can’t believe you would have hand-sewn them all.”
Sienna is surprised that the question was asked, and wonders if there was some trick behind the question. Sienna replied, “Yes, it was my Teacher, Susan Lane, and I; it took us a Saturday afternoon and evening, and Sunday afternoon until we were done.”
Johnson laughed, “That’s what the dressmakers do.”
Sienna unapologetically said, “I didn’t have the budget that some others have.”
The Judge said, “Maybe you weren’t ready to compete then?”
Contestant Jan Adams said, “Isn’t that what the pageant is all about?” Johnson remained quiet after that.
There would be a swimsuit competition ending the afternoon program. Sienna’s Mother had stretched the budget and bought a small blue Lurex one-piece backless swimsuit made for the occasion. Sienna’s back was beautifully toned, and wearing 4” heels gave her legs and hips a nice, feminine appearance.
Sienna was shaken by Judge Johnson’s remarks. Amy sympathized with her and warned her. "You did well. You need to reassure yourself and smile before the evening program. Seemingly, the senior official had warned Johnson that he had ventured into a gray area with his remarks and question. What he had done came with no formal warning or remarks.
The group would be trimmed to fifteen contestants, come morning.
To be Continued…Please, leave a comment or write the author a PM (personal message). Your comments are helpful.
Sienna Begins Day Two
Boy confesses he's jealous of his sisters...
Mom offers to pamper him...
Two sisters offer to help...
Dad is upset, but relinquishes...
Beauty Pageant for Teen Boys as Girls...
Sienna idolizes Amy, likes being a sister…
The Pageant Day Two…
=^_^=
Previously: The group would be trimmed to fifteen contestants, come morning.
Sienna hoped she would at least be one of fifteen. That would be a moral victory for a first-time contestant.
There would be a group song and choreographed presentation, with the contestants once again in lovely gowns. Then they were in their positions with the full group. Michelle began to call the names of the fifteen beauty girls, “When I call your name, come and stand on one of the fifteen stars.
“Now for the fifteen contestants advancing into today’s competition:” The first name announced was Silvia Oakland.” There were eight others announced before the Haynes family heard Sienna’s name and properly applauded and cheered.
The audience could celebrate, but no one was to become vocal and call out names. It did happen twice, but the Haynes were part of either group.
There was a song and a parade for the audience to show appreciation. Those contestants were eligible to be selected for Miss Congeniality.
The fifteen were asked to walk the runway and show who they were. Once back in, they would be excused to go change and prepare for their interview during the intermission.
The fifteen were excused backstage to find their changing area. Mom and Amy were already there to help Sienna change into her dress. It was the short blue dress that she and Amy had selected during one of their shopping trips. Amy was also setting up a vanity for a change of makeup and hairstyle. Tiffany and her mother were both backstage helping today. Tiffany swallowed hard when Sienna came out in her dress. The dress was shorter than Tiffany had expected. “Oh my, Sienna! I hadn’t remembered the dress was this short. There will be boys out in the audience waiting for you to parade down the runway.”
It caused Sienna a small scare, until her Mom said, “You remember we talked about that. You make a very beautiful young tee.” Amy held up a mirror for Sienna to see herself and regain her composure. She sat at the vanity and with Amy and Mrs. Hayes doing her makeup and hair. Amy used a blush that caused her cheeks to shimmer, and with that, there was a sparkle to her eyes as Sienna was delighted with the effect. The eyeliner was narrow, but it caused her eyes to stand out. Mrs. Hayes brought more curves to the hairstyle.
Sienna commented, “Are you two going to be around to glamour me up for a country club night out?”
Tiffany’s Mom said, “Does that mean you’re going to continue to be a girl at times?” Amy indicated her Dad might have a say in that.
Sienna was soon back in her position on stage. Sienna did well in presenting how she came to be in the contest, becoming a pampered boy. That the name came with Sammy and sisters Sheila and Staci sharing ideas, and Sienna was the choice that made us all smile.”
Fortunately, or unfortunately, it was Sienna who drew one of the thorny questions. Michelle asked, “What do you think of the job President Trump is doing so far?”
She took a deep breath, took little time to reply. “Well, I think we should give whatever support Ukraine needs to care for its people and protect it from Russian aggression. I also believe that vaccinations are needed for the health of children and others for a healthy country. I hope that is enough.” Michelle said, “Thank you.” And sent Sienna on her way. There was a pause before the audience rose to their feet and applauded.
The interviews had only gone a short way before they adjourned for lunch. This time the contestants were isolated from others. It soon became apparent that they were being watched for how they ate and were able to remain presentable. Contestant Kathy Ford came over to Sienna. “I think you did well in your answer to your question, and the audience agreed. The question will be what the Judges thought.”
The contestants finished with their interviews and answered questions by three thirty.
Come the evening, the stage would be set for their dance with a partner. She didn’t get partnered with either of the two male dancers she knew. However, she and Charles did match up well. She was lifted up into the air with little notice, but she was relaxed in the hands of her partner and landed smoothly.
It was her mother who embraced and complimented her at the end of the dance. Sienna enjoyed twirling around as she passed under Charles' arm and back again. He pushed her out once more and brought her back onto his knee as the dance ended. Once again, the performances could be subject to their evaluation, and Sienna and the two first timers weren’t sure how they’d be evaluated
Once again, there would be an evening gown presentation with the contestants being responsible for their own hair and makeup this time.
There would be a group presentation of choreographed dance and singing.
It appeared that some of the contestants were good at the choreographed dance portion, but some did not sing out for their portion of the song. Unfortunately, for some, it was captured on the screen. Thankfully, Sienna had not skimped on her participation and enjoyed moving; her movements were spot on.
There was an hour and a half for the break, but most contestants snacked on protein bars, yogurt, energy drinks, and the like.
It was time for the final evening gown change, and the contestants would be responsible for themselves, with the lone exception of putting on their gowns.
Amy and Sheila had Sienna’s gown among three she could choose from, her makeup was set up at the vanity table mirror and proper lighting; a table with a limited collection of hair styling tools was close at hand. Amy and Sienna had agreed that Sienna would use a limited number of tools to acquire the hairstyle she had chosen.
Sienna remembered, as she waited, a small snafu when the group danced and sang together. It wasn’t her mistake but it did cause her to miss a step.
She was in front of the gowns and perused her choices; she went with the one that Amy and she had agreed upon. It was set on a hanger near her vanity. She chose a slip, stockings, and shoes, and gathered them nearby.
Wipes were used to take off her makeup, a makeup cloth removed the remaining makeup and oil, and her moisturizer was but three simple spots, spread thinly over her face. She passed on using a concealer and went to the foundation. It was thicker than usual; it was designed for the stage lighting and cameras. She used a dark purple liner that appeared black but showed with a dazzle. She outlined her lips and then used a blush to give the appearance of her cheekbones. She used a mint green eyeshadow with a golden highlight above it.
Choosing a dark cherry red lipstick, she filled in her lips and used a tissue to blot her lips. She chose a cameo necklace, put it on, and centered it.
Sienna brushed her hair forward, obviously a different hairstyle. Using a curling brush, she brought her hair back in sections; the last section being brought back took longer as she did a stronger curl and brought it down the side of the face. She used a comb that gave more of a feathering look to add dimension to her hair. There were the setting to two hairpins and two decorating brads of a light yellow.
Sienna put in her earrings and brushed her hair back in place with the earrings showing, as she wanted.
Sienna asked her sisters, Sheila and Amy, to help her with her gown. Sienna had reached her zipper in the back and raised it all the way, with one pause to change her hands to finish pulling up the zipper, and then connected the eye and hook at the top. Amy was allowed to button the many small buttons up the back.
She again sat at the vanity to wait. She got Amy’s attention and showed to the delight of both that her feet reached the floor because of her wearing heels.
Sienna was third back in her place; she drew a number that indicated the order in which she would process down the runway and to answer her final question of the day. It was now totally Sienna, not Scotty, who was in the Beauty Pageant. She thought to herself, ‘I wonder if this is how Amy felt in her pageant?’
The music changed, which meant they were all ready. Sienna would be the thirteenth to process down the runway and back. She listened to Michelle Turner ask her question.
She noticed that at least three contestants who went before her had noticeable problems with their hairstyles, another who had a wardrobe malfunction, and two who were missing some makeup. It caused her to wonder and consider if she, too, had missed anything?
The contestant before her was heading back on the runway, and Sienna had herself all ready to go. MC Michelle Turner asked her question, and Debbie, with a bright spirit, brought a smile and laugh to Michelle with her response. The music started again, and as the soloist was singing as Sienna stepped forward. Some people were applauding as Sienna came down the runway. With one foot slightly stopping ahead of the other, she waved to the audience, paused, and curtsied to the audience. That had not been planned, and the audience drew quiet, and the applause became louder as she walked back to Michelle.
Michelle asked, “What can you liken this experience to for you?”
“Once when I was a young boy and got into my sisters’ things, I got caught having made a mess. I wrinkled Amy’s new skirt and tore a seam on Sheila’s blouse, by the time my Mom caught me. She said, “You know you are in trouble and in over your head. Before I discipline you, you need to know I love you.” Sienna looked at Michelle and then the audience, “I feel I am in over my head, yet the reception here affirmed for me that grace abounds and I should be here. I love my experience of being a girl here in this pageant.”
Sonya Harding was the last contestant down the runway. Sienna’s thought was that she would probably be the winner come the end of tomorrow. She and her gown were exceptionally beautiful. She didn’t fully hear Sonya’s response, but the audience strongly applauded her.
All the contestants were now parading as they sang in the last production of the evening. Standing in two lines at the end, Sienna was in the back row. She wondered, was that an indication that she would not be one of the ten finalists? When the first six names were called, they were all from the front row. Michelle then called out, “Sienna Haynes, please come forward.” She had seen contestants overwhelmed with tears of joy and thought it trite. Once again, she learned from her emotions; she was a girl at heart. Apart from Sienna, there were seven from the front row. The evening program ended with the selection of the ten finalists. Tomorrow, the final Ten would compete for the title of Miss Princess of the Springfield Beauty Pageant.
The televised program ended with Michelle Turner and the ten finalists hugging and congratulating one another. The Judges applauded from their positions and then left. Mom and Amy were soon there for Sienna, and support for the others came forward, and most of them would congratulate one another.
Sienna was soon backstage, changing out of her gown and into street clothes. They were joined by the rest of the crew to get something to eat, visit, and wrap up their evening.
The moment was surreal for Sienna, a boy who competed as a girl, and was now one of ten finalists. Amy was hugging Sienna as they left the auditorium. “Oh, Sis, I am so proud and happy for you.” She led Sienna to the vans they were using. Once to the restaurant, they were seated at two large tables brought together.
Once, the head of the restaurant realized this was a group with one of the finalists from the Beauty Pageant, he officially welcomed them. Ms. Briggs congratulated Sienna and complimented her. “If you are the winner or even one of the five finalists, please come here for a reception after your program ends tomorrow night. We would be delighted to entertain you.”
Everyone was in awe; no one had considered or planned for such a possibility.
Scotty wanted a big juicy burger and fries, and Sienna ordered a chicken sandwich, a small salad, and raspberry iced tea. They were the same, and while she was hungry, she focused on family and friends and celebrating the moment. She looked at each face around the long table and remembered how each person helped her get here.
She laughed, realizing that her feet would reach the floor in heels was something everyone now celebrated.
To be Continued…
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