The Pampered Boy 3 A Beauty Pageant for Young Teen Boys


The Pampered Boy 3
A Beauty Pageant for Young Teen Boys



Boy confesses he's jealous of his sisters...
Mom offers to pamper him...
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…



If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
up
5 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos

And please, remember to comment, too! Thanks. 
This story is 2453 words long.