My Little Sister

by Jennifer White

  

I kissed Dan good night, and got out of the car. We had been double dating with some of my other friends from school. Next year we were off to college, so this was our last Easter vacation before we all scattered. With mom and dad out of town for the week, I was determined to have as much fun as possible.

"Good night Lauren" he said.

"Good night Dan" I replied.

I put my purse over my shoulder, and walked up the steps. I turned to look back at Dan, and wink at him. I licked my lips too. Guys seemed to like that. I wanted him to go home and think of me all night. I guessed that if he was anything like my brother, he'd wanked off too. I preferred that it would be to an image of me, instead of some floozy in a skin mag.

I walked in, and caught the smell of smoke. Great, he was sneaking a cigarette. And I'd get in trouble, since I was in charge while mom & dad were gone, being the older sister. I had to track him down, and chew him out.

"Hey Chris!" I said

"Hey what" he sassed back.

"I can smell smoke. Mom & dad will kill us if we're smoking in here. How many times have I told you to open a window, or go out back?"

"Sorry. I didn't want to get up."

"Okay" I said. "Just don't blow it. They're leaving us alone all week. They trust us. You don't want to spoil that, do you?"

"I guess not."

I hated being the one who always had to tell him what to do. But hey, what are big sisters for?

 

I went up to my room, and changed. My shoes were uncomfortable, but they were so cute! Not that Dan would notice, but most guys were like that. It felt good to get out of my nylons and into shorts and one of Dan's oversized T-shirts. Very comfortable.

I put my dirty clothes into the hamper, and went to brush my hair. That's when I noticed. My panty drawer was open again. But I was sure I had closed it. I *always* kept my room straight, and always closed my dresser drawers all the way.

I opened up the drawer, and I was sure that someone had been going through it. Things weren't as neat as I had left them. I admit it, I'm pretty freaky about keeping everything just right. Someone had been going through my stuff again.

Now lets see: there's me, but I was out. There's the dog, but he doesn't know how to open a dresser drawer. So that left my little brother, Chris. I was really worried about him. For quite some time, I had the feeling that he was going through my things.

One day a month ago, I had wanted to wear my black demibra. But I couldn't find it! I was bummed. But then, one day, it turned up in my drawer, right on the top. I did my own laundry, so I sure didn't put it there. And mom's a cup size larger than me, so there was no way that she borrowed it. That left my little pervert brother.

I also found a strange spot on my good skirt a week ago. I had to wash it to get it out. I hadn't worn that one since I last washed it. So *someone* wore it, got a stain on it, and to top things off, stretched out the waistband! I knew it had to be Chris. And this topped it off.

I knew he was doing it, so I had to set a trap to catch him, because he'd never admit it.

* * *

 

The next day, I told him that I was going to the mall with Gloria and Stephie, and that I wouldn't be back until at least 3:00.

"I made a salad, if you want that for lunch" I said.

"Yeah, like I'd eat a salad" he replied.

"Your loss. Make something yourself then."

I got in my car, and drove off.

 

I went to the local party store, and got a can of diet coke and the latest issue of Glamour. I read it in the car for a bit, while I drank my coke. When I figured that enough time had passed, I drove back home.

Instead of parking in the garage, where he'd hear me, I parked in the street, two houses down from ours. The houses in our area were all really big, so it was a little walk down the street to our house.

I went around back, and quietly opened the door. I took off my shoes, so I could walk quietly. Then I headed up the stairs. I knew that they squeaked in the middle, so I made sure I stayed on the far right edge. It felt like walking on the balance beam, back when I took gymnastics.

I had left the door to my room wide open, but it was closed. I had him! I snuck over, and looked in the keyhole. I couldn't see him, but I heard noise, like he was going through my closet. I quietly turned the knob, and walked into my room.

There stood Chris. He had one of my bras on, and had stuffed it full with a couple of T-shirts. His 'boobs' weren't quite even, and were two different shapes. He had on my pink panties, and my nylons. He had my blue miniskirt in his hand, and he was in the process of trying to step into it.

"Hi Chris" I said.

He froze. All the color went from his face.

"This isn't what it looks like" he stammered.

"It looks like you're dressing up as a girl, in *my* clothes!" I said, fuming. "What part of that am I wrong about?"

"I'm sorry. Please don't tell anyone!" he said. He started to cry.

"I thought you had been doing this. You weren't very careful. You messed my things up! You left stains. I should...."

I didn't even know what to say. I was literally seeing red. In my mind, I went through dozens of things I should do to him, to get even. I could take his picture, and use it to blackmail him to do whatever I wanted. Or I could force him to go further, dress up all the way, and make him go out.

But as I looked down at him crying, my heart just melted. He was family, and I did love him, no matter what his faults. I was angry of course, but I cared for him, and that mattered more.

"Chris" I said gently, "Why do you like to dress up in my clothes?"

He just shrugged.

"I want to understand. I'm not mad at you. Its okay for you to tell me."

But he remained silent. However, his crying did slow down. I handed him a tissue.

"Please, just tell me. I know you get off on it, I've seen the stains. Tell me, do you do it because you're interested in boys?"

"No!" he said, very defensively. "I look at girls, and I *want* them. I think of them when I 'get off' as you say."

"Okay then, don't get upset. I'm here to help you. Now tell me Chris, do you wish that you were a girl? If there was a magic wand you could wave, would you use it to really become a girl?"

"I don't know" he said.

"Look, you're not telling me much to go by. You like dressing up as a girl, so you must think of yourself as one when you're wearing my clothes, right?"

"Yes" he said shyly.

"Well, you're in my clothes now. So you're a girl inside. And girls are in touch with their emotions. Now look inside, and *feel*. Tell me why you like to dress up."

"I guess its because it feels *right* when I wear your clothes. Like this is how I really should have been born. It feels *special* when I do it. I don't know why, but I feel like I have to. It just feels right."

"That's much better" I said. "You opened up a lot more. That was very good for your first try."

I took a deep breath, and thought. I wasn't sure what to do. *He* didn't even really know what to do. I wasn't a psychologist or anything, so I had no idea why an otherwise normal boy would feel compelled to wear his sister's clothes. But I had an idea.

"Chris," I said, "I don't know why you like to do this. The only one who will ever really know is you. Mom and dad are gone for the whole week, so we're alone in the house. And we're not supposed to have visitors over. So let me make an offer to you."

He looked up with puppydog eyes at me, with a hopeful expression on his face.

"Why don't we let you explore this week? Let you dress up like a girl, act like a girl, and *be* a girl. You can explore how it feels, and decide what it is you want to do."

"Really? You'd do that for me?" he said, amazed that I wasn't going to do something terrible or nasty to him.

"No. I mean it. You can be my sister this week. We'll dress you up all the way, and I'll help you. I swear that I won't tell anyone about this. Your secret is safe with me."

He looked up at me and smiled.

"Do you have a girl's name that you call yourself when you're dressed up?" I asked.

"Yes" he said. Still a one word answer. We would have to work on that.

"What shall I call you, sis?"

"Sara" he replied.

"All right. For this entire week, you are my sister Sara. I will teach you about being a girl. You will dress like a girl, walk like a girl, talk like a girl, and act like a girl at all times. This is serious. I'm going to totally immerse you in femininity. But if even for one moment you do anything male, it's over, and I won't help you anymore."

"It's a deal" he said.

 

"I need to go shopping and get a few things for you. How much money do you have?"

"I've got $50 in my wallet, and I've got $300 stashed."

"I'll take all of it" I said. "I'll need to buy you some things. Now I know that you like to get off when you're in my things. Do that while I'm gone, because I'm not going to do this if its just to get you aroused. Right?"

"Right" he said, nodding his head.

"Then take a bath. My bottle of Nair is by the tub. Use it all over, to get rid of your body hair. And there is scented bath beads in the jar. Put them in the tub, so you come out smelling nice. I'm going shopping, and I'll be back in an hour. I want to see you waiting on your bed, wearing your bathrobe. Read my magazines while you're waiting, so you can start to understand more about makeup and fashion" I said, as I handed him the new copy of Glamour. He would need it more than I ever would.

"It's a deal" he said, ecstatic about the turn of events. That made me smile too.

"See you soon, *sis*" I said, as I took his money, and headed towards the strip mall on the east side of town.

* * *

 

Armed with my new purchases (with his money!), I returned home. I went up to his bedroom, and sure enough, he was there like he said he would be.

"Hey Sara, I'm back" I said. You should have seen the look in his eyes. He was so excited! And now this would be the best part for him: the transformation. All this would be new and exciting. I just hoped he liked it in a couple of days, as much as seemed to now.

"Lets see those legs of yours" I said.

He showed off his smooth legs.

"Really cute legs Sara. They'll look great in nylons. But first we need to get a couple of things in place."

I pulled out from the first shopping bag something that I had bought at a specialty store in the mall. A pair of falsies. Fake boobs, that they sold to women who had breast cancer and needed good fakes, or to those of us not blessed with big ones.

"Put these into your bra" I said, handing over the box, along with a padded bra I purchased, guessing at his size. He excitedly put it on, and slipped the skin colored silicon blobs into place.

"They're cold!" he said.

"Don't be a big sissy. They'll warm up."

"They feel so...wonderful. I like having them" he said.

"I'm sure you do. Next, I got you some special panties."

They were padded, designed for women who lacked natural curves. There was padding in the butt, and in the sides. He put them on while I left the room.

"It's okay to come in!" he yelled.

"Looking good Sara. Now put this on. You need some more shaping."

I handed him a girdle. He seemed confused, so I had to show him what to do. He stepped into it, and I helped adjust it. It was quite tight on him. Between the padding and the girdle, it gave him the illusion of having curves.

"Next, I bought you an outfit" I said.

I had purchased a short black skirt for him, and a Lycra cami top with spaghetti straps. He put it on, along with the skirt.

"My bra straps are showing" he said.

"That's the look I was going for" I said. "If you look through my magazines, you'll see lots of chicks dressed like that."

"What's next?" he said, all excited.

"Well Sara, we needed to do something with your hair. So I got you this."

I pulled out a wig, with long auburn hair. I sat him down, and showed him how to put it on.

"I love having long hair! It make me feel so....free!" he said.

"And wait until I get makeup on you. You'll really look pretty" I said.

I sat him down at my vanity, and taught him the basics of applying makeup. It took quite a while, but soon we had prettied up his face. He asked lots of good questions, and I told him that since he was going to be Sara all week, there would be plenty of time for him to practice.

Then I got out the ear rings I had bought. They were fake diamond studs, the new kind with magnets so that it looked like you pierced your ears. I also had an old ring I gave him, and a bracelet.

"Now lets do your nails" I said.

I had bought fake 'press on' nails, which I applied to his fingers. I showed him how to shape them, and how to paint them. Then I did his toes.

After they dried, I pulled out the mules I bought him at the shoe store. It was funny to watch him teetering around on them, even though the heel was only three inches. I should have bought the six inch stilettos, but that would be cruel, wouldn't it? No, these were better for starters, although I personally preferred something more strappy when I dressed up.

"Now lets teach you how to walk properly" I said. I felt like a ballet teacher, going over the basics of how to move with grace. It would take a long time before his walk was passable. But he sure seemed to enjoy what we were doing.

"Oh, I almost forgot. I bought you a purse too. A girl never leaves her purse out of sight. Keep it with you all the time" I said.

He opened up the cute little DKNY knockoff, and looked inside. I had placed in it a bunch of things that I normally kept in mine. Makeup, tissues, tampons. That seemed to freak him out.

"Why did you put those in there?" he said.

"Sara, you never know when your period will start. You need to be prepared. What's wrong with you girl?"

I think it was then that he realized that I was really going to treat him like a girl, like he was my sister. There was such a look of delight in his face.

"Come on sis, lets go watch a movie. I rented White Oleander. It's a real chick flick. You'll love it."

And so I sat on the couch with my 'sister', eating popcorn, and watching a movie. I never thought I'd see the day.

* * *

 

That first day of being Sara, I thought Chris was going to cry for being so happy. Everything was new and exciting for him. And it turned out to be a blast for me too. Just like any girl would be, I was upset when my parents told me that I had a baby brother. I had wanted a sister! They told me I cried when I heard the news, but I guess I got over it right away.

So this gave me the chance to do all that things I had always wanted to. I got to dress 'her' up. I got to teach 'her' how to do things. Instead of a 'bossy older sister' telling her brother what to do, I was looked at as the wise teacher, imparting knowledge. So he loved it as much as I did. I didn't realize how much fun this was going to be.

 

The second day, we made a few more adjustments to Sara. Under my direction, he even plucked his eyebrows, which helped make his face look much nicer. Then I had him start wearing perfume. And we worked hard on his walk, so he'd swing his hips, and hold his hands right. Slowly but surely, he was starting to get it.

As we spent all this time together, I was also thankful for how we were bonding. I never had the greatest relationship with him, but now we were doing everything together, and there was a closeness neither of had known as brother and sister.

'Sara' was practicing 'her' makeup techniques, when the phone rang. I picked it up.

"Hi mom!" I said. "No, everything is just fine here. Yes, we ate the meatloaf you left for us in the fridge."

I made a face at him, and he giggled.

"Yes mom, Chris is behaving just fine. No, we haven't had any friends over. I'm 18 mom, I'm responsible! I wouldn't tell you one thing, then do another."

She was sorry, but you know how moms are. I spoke to dad too, and also told him everything was fine. I was sure that they'd compare notes as soon as we were done, so they could see if I had told a different story to either of them. Like I was still 15 or something. Geez!

After being interrogated by mom and dad, I could turn my attention back to 'Sara'. There was much work to do.

* * *

 

It was now the third day, and I wondered if Chris wasn't starting to get tired of what we were doing. The newness and excitement had worn off it seemed, and he wasn't as enthusiastic as he had been.

"I feel cooped up in here too" I said. "I need to get out and do something. What do you think?"

"Yeah. I'll go change, and we can go somewhere" he said.

"Good idea. That skirt is too dressy for just hanging out. Try my denim skirt. It will go nice with that top."

"I meant dress as a boy" he said.

"A boy? Why would you do that Sara?"

"Come on Lauren, you know I can't go outside like this!" said Chris.

"Why not?"

"People will look at me, and think I'm a girl."

"That's the whole idea, isn't it? Look in the mirror. Who is going to see you like that, and mistake you for some boy named Chris? You don't look anything like him. You are Sara now. And I think you're just itching to go outside, and feel the wind under your skirt for the first time. What do you say Sara?"

Chris was still seemed reluctant. I think he was afraid that someone might recognized him. But he felt cooped up. And I had made it clear that if he changed back to being Chris, I wasn't going to help him be Sara anymore. So he made the only possible decision.

"Where do you want to go?" he said.

"To the mall, so you can buy some new outfits. You can't go around wearing my clothes all the time. You need to get some outfits of your own, so whenever you want to dress up, you have your own clothes."

So we were off to the mall, where Chris was going to experience shopping as a girl for the first time. He had been carefully studying my fashion magazines, so he knew what the looks were that all the girls were wearing. He was eager to give it a try.

"Don't forget your purse" I said as we walked out the door. There was a gust of wind as we walked to the car, and his skirt fluttered in the breeze.

"Wow!" he said. "That sent chills up and down my spine."

"Yeah, I love that feeling too. I'd wear a skirt all the time if I could. But sometimes you've got to wear pants. Maybe you should get some girl's jeans today too."

 

I drove us to the mall, and started us out at a place I knew that had reasonable prices, but trendy fashions. I picked out a couple of outfits, and went to the fitting room to try them on. Chris seemed shy at first, but grabbed a red dress, and dashed into the next fitting room.

When we were done, we met to check each other out.

"Cute!" I said. "That's a good color for you. It really brings out your hair."

"Thanks" he said. "I like your outfit too. But don't you feel uncomfortable with that low of a neckline?"

"Yeah" I said, "Mom wouldn't let me wear this. And dad would kill me if he saw this. But it sure would get the boy's attention, wouldn't it? Good thing there aren't any boys around here!"

He ended up buying the dress. We had credit cards. Chris was a name that could be for a boy or a girl, so the saleswoman didn't question him upon checkout.

Now we went off to buy more shoes. I just loved shoes, and could never get enough. I did feel guilty about the pairs I bought for special occasions, then only wore that once. But hey, they might come back into style one day, so I wasn't about to get rid of them.

I found the cutest boots that had a little heel, and came up to my knees. 'Sara' liked them too, and found a larger pair that fit 'her'. Then we went off in search of accessories.

 

We had bags full of clothes, which we dropped off in the car. We went back inside to get a snack at the food court. As we sat down to eat, a pair of cute boys asked if they could join us.

"Hi, I'm Matt. This is Frank"

"Nice to meet you" I said, looking them up and down. Dan would be insanely jealous if he knew I was flirting with someone else. But that was good for him, to keep him on his toes. Not that he'd find out, anyway.

"I'm Lauren" I said, "and this is my sister Sara."

"Sara? Nice to meet you" said Matt.

"She's a little shy" I said.

"You're very pretty Sara" said Frank.

"Oh, thanks" said Chris in an unnatural voice. He was trying to sound girlish, I guess. I could tell he was really uncomfortable.

"How's the shopping?" I said, trying to break the ice.

"Oh we're just hanging out here today" said Matt. "How about you?"

"We've been all over the stores" I said. "Tell them Sara."

I wanted to get 'her' in on the conversation. Girls like to talk (well, most of us anyway). If 'she' was going to pass as a girl, then 'she' had better start talking.

"Well lets see. I got some really cute shoes, and a pair of boots. And I got this dress, jeans, a couple of tops, a hat, and a new necklace."

"Wow, you chicks really get into clothes and stuff" said Matt.

"Yeah, ever girl I've ever dated loved shopping."

"Who are you dating now?" I said.

"Nobody" he replied. "What about you?"

"Oh, I've got a steady" I said. "But Sara here is another story."

"So Sara, what are you doing tonight? Would you like to go with us to the movies?"

"I don't know..." said Chris.

"That's all right. I'll give you my cell phone number, and you can call me if you change your mind. Catch you chicks later"

With that, they were off.

"What are you doing!" said Chris angrily.

"Trying to help you out. He's cute, and he wanted you to go out with him. What an opportunity! One day at the mall, and you're already getting asked out by guys."

"But I don't want to go out with a guy, remember?"

"Yes. I just wanted to see if you really meant that. I'm just trying to help you Sara. That's all."

* * *

 

The next evening, I had another suggestion for Sara.

"Since you didn't like hanging out with boys" I said, "then how about I have a couple of girlfriends come over tonight? We can hang out here, just us girls."

"But mom and dad said we can't have guests while they're gone."

"You're right. Then how about we go over to Angie's house? We'll just go and hang out with girls. No guys. I promise."

He thought about that for a while, but eventually he agreed. I called them to make the plans, when I was sure that he wasn't listening. This would take a little extra preparation.

You see, he looked *like* a girl, but if he hung out with any real girl for more than an hour, she'd be able sense who he really was. He might have fooled a teenage boy for 5 minutes, but there was no way he'd fool a girl. So I needed to prep my friends...

 

We arrived at Angie's house. Her friend Marge was there already. She had a movie ready to roll, a veggie tray, low fat chips and dip, and some drinks. Her folks were gone, so they would never notice a little bit of rum missing.

We started talking right away. As usual, 'Sara' was a bit shy, and needed lots of prompting. But they knew what they were dealing with, and encouraged 'her' to talk. I thought this would be very good for her, to see how girls interacted with each other.

As usual with my friends, we turned on the movie, but within 20 minutes, our attention wandered, and we ended up talking more than watching. I thought everything was going very well, but then Marge got a call on her cell phone. She talked for a while out of the room, but came back to us in tears.

"What's wrong?" said Angie.

"Walter just broke up with me! Over the phone!"

She was terribly upset, and we tried our best to comfort her. But after her sobbing, she flew into a rage.

"I hate him! I hate men!" she said.

"They can be difficult" I replied, trying to console her.

"I don't want to see another man as long as I live. Not even him!!!" she said, pointing at Chris.

"But..." he started.

"I know who you are" she said. "I can tell you're a boy."

"I'm not! I'm a girl!" he said.

"Oh yeah, well hang on then"

She stomped off to the kitchen, and returned a few moments later with something in her hand, and a glass of water.

"If you're really a girl, then take a couple of these."

"What are those?"

"My mom's estrogen pills. If you're a guy, these will make you grow boobs. But if you're a girl, you're already flooded with estrogen, and it won't make any difference."

"Marge, you shouldn't give them to someone without a doctor's approval. You don't know what they'll do..."

"Oh, so protecting him? Either he takes these, or he leaves right now."

Before I could stop him, Chris gulped down the oval shaped white pills.

"And these are birth control pills. Take these too!"

He also swallowed them.

"There, satisfied?" he said.

She just stared at him.

"You're a guy, but you're willing to take female hormones? What, are you queer or something?"

"That's it" I said. "Come on Sara, we're going home."

We walked out the door. Sara remembered to grab 'her' purse.

"Someone opened my purse!" he said.

"Is anything missing?" I asked as I started the car.

"No, but she put the birth control pill dispenser in here. Should I return it?"

"No, lets get out of here. You can just throw that out."

"What if I want to keep taking the pills?" asked Chris.

I almost hit a parked car. I had to pull over to look him in they eye so I could talk to him.

"What are you talking about?" I said.

"Remember at first you asked me why I wanted to be Sara? Well now I know. When your friend called me a boy, I felt totally insulted! I hate being a boy. I hate everything about it. I hate all things male. I never want to go back. If you had that magic wand, I'd wave it right now and turn myself into a woman."

"You don't mean that" I said.

"Yes I do. I want to start taking hormones. I want to become a real girl. I know that I'll need surgery and stuff to fix me up, but I want to do this before I develop too many more male traits. Please, help me. Help me be a girl. I'll do anything you want. I just want to be like you."

We hugged each other, and both of us started to cry. I was so upset with myself. This was supposed to just be a game, and get his urge to wear my clothes out of his system. But I had somehow convinced him that he wanted to be a girl all the time.

"If you do this, you'll have to go to school in a skirt Monday. There's a dress code you know."

"I know. I want to wear a skirt to school. I want to wear shoes like yours, and a cute top like you get to wear."

"And you'll have to tell mom and dad that you're becoming a girl now, and face them. They'll be upset."

"I know. I can handle it. I'm sure they'll take me to a psychologist or something, but I'm not afraid. I know what I am, and what I want to be. I'll only be happy, if I can be a woman."

"But Chris, you've just done the glamorous things. Clothes. Makeup. Shoes. You haven't lived the day to day reality of being a girl. Being ignored by the teachers, as they call on boys. Being scared to go out, because its unsafe for a woman to be on the streets alone after dark downtown. Getting passed over for promotions at work, for a less qualified man because he's buddies with the boss. I've seen all that already, and I'm not even in college."

"I know. And I've read all your novels about girls and women's lives. I know more than you give me credit for. These past few days have been a test drive. And now I know for sure. I want to be a girl. Oh and one more thing. Please don't ever call me 'Chris' again. I'm Sara now."

* * *

 

Epilogue:

College was a great experience for me. I graduated with honors, but I must admit that my senior year was a lot of fun for me, because I rented an off-campus apartment with my friend Angie, and my sister Sara. We had the greatest time together, studying, going out on dates, and of course partying. There was a frat house just down the street, so there was never a shortage of guys for us. Sara said she wasn't going to get married until after she graduated. But I'm not too sure. She seems really stuck on Matt. Her grades even slipped a bit last semester, so I've got to keep on her case.

I don't know if dad ever got over losing his son like he did, but mom sure loves having another daughter to teach everything to. I've never seen Sara so happy before, so in the end, it all worked out for all of us.

Wow, I never would have believed it. A happy ending for me and my little sister!

  

  

  

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