The Pampered Boy 2 Extended Experience


The Pampered Boy 2
Extended Experience


By Jessica C

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…



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