Synopsis:When Robert's lying, habitual stealing, and attitude about women gets to be too much for his mother, she comes up with a Plan to help her delinquent son turn around.

It took a little while for the magnitude of my punishment to sink in. I’m still not sure when I realized that I’d have to actually be convincing as a girl or face untold amounts of ridicule. High School being the place it is, you don’t want to give people a reason to put you down.
Still, for the next few weeks, I watched in a daze as my life changed around me. It started innocently enough, Mom had me and Josh, my little brother, paint my room. I didn’t mind, my room’s wall changed from a boring white to a light shade of purple with blue flowers along the border.

As far as I knew, Josh didn’t know about my punishment and I intended to keep it that way. I justified the new color scheme as “still pretty macho.” After all, blue is a guy color, flowers aren’t the exclusive property of girls, and purple was considered the color of royalty. I’m not sure if he bought that but at least he stopped asking me about it.

After the room was painted, Mom took the liberty of adjusting the furniture. My old bed was a captain’s bed. Mom said it was too masculine for my new role and replaced it. She also bought me something she called a vanity. I didn’t know what that was, but Mom said that all girls have one.

I was sitting in my room “cleaning” it up a bit. I used to tell my mom that I worked better if I wasn’t interrupted, so cleaning my room became an excuse to lock my door and read certain materials that Mom wouldn’t have approved of.

I really didn’t need anything much to get excited, a little SI Swimsuit issue or even just looking at models in shopping catalogs usually was enough to give me much enjoyment. Anyway, I was sitting in my room when Mom called me to her room.

“Robert, I’ve lain some clothes out on the bed. Put them on then get in the car.”
I glanced at her bed. Lying there was a knee-high jean skirt and a white shirt. I know girls don’t call them shirts, but I never bothered to learn about girl clothes. Something tells me I’ll need to learn all about them before school starts. Also lying there was a red bra and panties.

“Mom, you can’t be serious. There’s no way I’m wearing this stuff to go out! The punishment is that I attend school as a girl. Unless you haven’t noticed, school hasn’t started yet. You can’t just force me to do what you want.”

“Alright son, that’s fine. I thought you might want some experience with what will be your new wardrobe. But, if you’d rather not, that’s fine.”

I could see her point, but I wasn’t going to let it go. Seeing the clothes on the bed woke me up and I was going to fight this if I could, “Besides Mom, you aren’t even in charge of this family, Dad is. I won’t have to do anything if he says so.”

“Your Dad’s been busy in England, but even if he doesn’t know about it, it doesn’t matter. He trusts and supports me. And while he’s gone, I AM in charge here and you WILL obey me. Now get in the car!”

I could tell that questioning her authority was making her mad, so I decided to play along. What harm could a little car ride do? We started driving along in silence. I finally decided to speak, “Mom, where are we going?”

“Hmm? Oh, you need clothes for your new life. And I can’t just go buy everything you need without you trying them on, first.”

“But Mom! I’m a boy! You can’t just make me try on dresses in the middle of a mall! What if someone sees me?”

“Well, I offered you the chance to go as a girl. But as I recall, you refused.”

“No, this is stupid, I’m not doing this. I’m getting out and going home.”

Mom stopped the car and turned to face me, “Young man, I’m trying to offer you redemption and you keep throwing it in my face. Still, I had an idea that you might do something like this. I had your brother bag all your clothes. If you continue with this rebellious little act, those clothes get donated to Goodwill. But if you promise to be good little girl and actually keep that promise, you’ll get your old life back, once school is over.”

She turned the car around and headed for home. Damn. She really had this all planned out. “Alright, Mom, I’ll be good,” A few seconds later, I looked at her. “Mom? Why are we still going home?”

“I never asked you to promise to be good. I’ve heard that promise too many times for me to believe. You’ll just go back to being a horrible teenage boy, and the only difference will be how well you try to cover your tracks.”

I sighed. I was reluctant to say those words cause I knew that was a step I couldn’t come back from. Still, that seemed to be my only way out, “Mom? I promise to be a good little girl and make you proud to have me for a daughter.” I was hoping that going overboard would help make my case.

“Oh sweetheart. I’m so glad to hear that!” Mom stopped the car and gave me a hug. It’d been so long since we’d hugged like this that I never realized how good it felt. Mom turned the car around and headed back to the mall.

“Uh Mom, can we go home? I really don’t want to go to the mall like this. Can I go wear what you picked out for me?”

“Sweetheart, you know actions have consequences. Just because you promised me something doesn’t change the consequence of your earlier actions. You made a choice and you still have to live with it.”

“Mom is there something I can do to get you to change your mind?”

“Well, maybe. If you showed me that this time there’s more to your promises than empty words…”

“How am I supposed to do that?”

“Well, Sweetie. Even if you were wearing your skirt and blouse, your hair still looks like it belongs on a boy. Plus, your legs are getting hairy and that would be a dead giveaway, as well. “

She didn’t finish her thought, I knew where she was going with this, “Mom, would you please take me to a beauty salon? I want to get my hair and makeup done there. I really want to be the best girl I can be, both inside and out.” Laying it on too thick? Yes. Still I figured the more I overplayed my role as a girl, the better the odds that Mom would relent.

“Sure, Sweetheart!” Mom turned the car around and we headed for home.

We got home and I looked at Mom with a mixture of fear, nervousness, and expectation. She told me to go run a bath, so I walked upstairs, every step the impending sense of doom increased. I got into the tub and ran the water. It was actually surprisingly relaxing. All that tension came flooding back when Mom walked into the restroom.

“MOM! What are you doing?!?”

“I’m here to show you how to shave your body hair.”

“Can’t you just tell me from OUTSIDE the bathroom?”

“Why? We’re all girls in here and I need to make sure you’re doing it, correctly.”

Mom watched me and showed me exactly how a girl shaves her legs. Luckily for me there, wasn’t too much hair there. More hair than a girl should have, but not enough for a 17-year old boy. There’s a reason I usually wore jeans at school. The few times I wear shorts I get teased about shaving my legs. After cutting myself a few times, I wrapped a towel around myself and walked into my mom’s room.

“Roberta! Show some modesty!“

Oh gosh. Roberta? Really? No matter what happens, that’s a name that’s got to go, “Modesty Mom? What do you mean?”

“Berta, Honey. I know you’re flat-chested, but most girls your age have breasts and they need to cover their chest.“

I readjusted the towel then looked at Mom, “Mom, if I’m going to do this, that’s a name that’s got to go. I hate the name and it’s too close to Robert. Someone’ll figure it out.”

“Well, Sweetheart. If you have a name you’d prefer, feel free to tell me.”

“How bout Bobbi? It is a female name, Mockingbird’s real name is Bobbi Morse and even if she’s a fictional comic book character, the name’s still female.”

“I don’t know. It’s a pretty enough name, but I think that when people hear it they’ll still picture a male. How bout Barbara?”

“It’s better, but isn’t Barbara a more common name in your generation, Mom? If I’m going to do this I at least want to be modern. How bout Rebecca, or Becky for short?”

“It’s perfect, Sweetheart. Now put your clothes on, your little tantrum earlier has cost us some time, so we need to hurry. Just come out to the car when you’re done.”

The moment of truth. I walked forward to the bed and pulled the panties up my legs. To my surprise and, to be honest, horror, they actually felt good. The soft delicate fabric was all it took for me to be sold.

But I’m a boy! I’m not supposed to feel this way about panties, right? Anyway, I then started to put on the bra. I knew women did something where they put it on, then strapped it behind their backs. But I was pretty sure I wouldn’t be able to pull that off, those hooks are tiny!

So, I strapped it in front, then spun it around and put my arms through the straps. Again, I felt another very strange feeling; it was a mix of excitement and pure pleasure. The only feeling I’ve had that was close to this was the feeling I get when I’m in the middle of tricking someone into handing me their valuables.

The blouse and skirt followed suit along with these black flip-flops that Mom had put by the bed. Taking a deep breath, I walked outside and was hit with a gust of wind. I never realized how free and open a skirt is and feeling the wind inside my skirt was definitely a new feeling. I shrugged it off and got into the car.

“Rebecca, you look so pretty!”
Just what every boy wants to hear, how pretty he looks. Still, I played along. “Thanks Mom! You did pick out the combination so I’d expect it to be good.”

We headed towards the mall. Mom had made an appointment at a local beauty salon, so we stopped there, first. Mom had the lady give me a new hairdo and then teach me how to do my makeup. It was a lot to learn, but I am a good student and I picked it up quickly. Of course, the whole time there was a part of me that was screaming that I wasn’t supposed to be doing this, that only girls wear makeup and I’m not a girl!

Still, I would be playing the role of a girl and I told myself that all actors wear makeup. Anyway, after we were done, I looked at myself in the full-length mirror at the salon. I was stunned by what I saw. I saw a cute girl with short black hair that came down to about her jaw. Her makeup was done flawlessly, bringing out her dark brown eyes. She was actually quite good looking. Not the prettiest girl I’d seen, and she definitely was lacking a rack, but I’d definitely go out with her. Oh God, am I actually thinking about going out with myself? The thought disgusted me. I turned to Mom and we headed out to the stores.

I won’t bore you with the details of the shopping trip. Let’s just say that no matter what happens, I will not enjoy shopping. Time seems to slow to a crawl the second anyone enters a mall. I know teenagers, especially teenage girls, hang out in malls, but if anyone ever found me giggling and gushing over clothes like the airheads in the mall, I would thank them if they shot me.

Anyway, replacing a wardrobe is no easy task and Mom wanted me to try on half the mall. We got out of there with enough skirts, blouses, t-shirts, skirts, dresses, pants, shorts, and other stuff to last me a lifetime. I was surprised to find that no one really paid me much attention. In fact, the only place that I was really embarrassed was when Mom dragged me into this store and had me measured for fake boobs. Mom and the saleslady were throwing around a bunch of sizes I didn’t understand, but apparently, I’m now a 34B.

Having some strange lady stick those fake boobs on my chest was probably the most embarrassing thing to happen to me in a while. Don’t ask me how she did it, I didn’t care to know. All I know is that boobs are definitely heavy and all of a sudden I was really thankful for the bra I was wearing.

After a long day shopping, I was exhausted and ready to quit. Mom handed me several bags of clothes and I headed inside. I was stopped dead in my tracks as I walked in. There, sitting on the couch with his mouth wide open, was my little brother Josh. He took one look at me and started laughing. That was more than I could take. I dashed upstairs and threw myself on the bed, the tears streaming down my face.

Thanks to everyone for the warm welcome! As always I appreciate any comments/feedback that you might have!