(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…