Big Help from Lil Sis Pt. 01

Big Help from Little Sis- Part 1

First part of a three-part story. All characters are 18 years of age or older.

The alarm on my phone woke me up and I immediately reached for it to hit snooze. I heard my roommate mumble something, that I couldn't understand from his bed on the other side of our dorm room. I didn't want the alarm to go off again so I forced both eyes open. I considered for a minute just turning the alarm off and going back to sleep.

I remembered why I had set the alarm and tried to use that as motivation to get up. I opened my phone and went to Facebook. I found the page I was looking for and after a finding the pics I wanted to look at I was up and out of bed and dressed. A quick trip to the bathroom we shared with the room on the other side and I had peed, washed my face, and brushed me teeth.

I could hear my roommate snoring lightly as I grabbed my phone, keys, and the duffel bag that I had packed last night and slipped out of the room. I decided to walk down the three floors to the exit instead of waiting for the notoriously slow elevator to exit. Plus, it would shorten the walk to my car by a few hundred feet by going out a back door.

Starting the car and pulling out of the parking lot I realized I would need some gas to make the drive to my house. This would work out because I could get a cup of coffee and a couple of donuts at the same time for my breakfast. The drive would take about three hours and I was planning to make a stop, maybe, on the way. That should get me home around eleven-thirty I hoped.

I had been on the road for about an hour when I called my mom. She worked the ten am to ten pm shift at the hospital as a nurse three days a week and would be getting ready to leave for work soon. I also knew that my sister would have left for school and wouldn't be home now.

"Good morning, Honey." Mom answered when I called.

"Hey mom. How are you?"

"Okay. Getting ready to head to work and finishing a little packing. How are you?" She responded.

"Good. I am on my way home. Just wanted to let you know." I tried to sound a little put out about having to come home.

"Oh... okay. I didn't think you would get here until late this afternoon or early evening."

"Yea... I didn't have any classes and woke up early so I just decided to head home." I lied a little. I didn't have any classes, but I hadn't just woken up early, that had been intentional.

"Thank you for doing this sweetie. I really appreciate it. It will allow me to enjoy the weekend a lot more knowing you are here and your sister isn't home alone. We are leaving at nine-thirty tomorrow morning, should be home around three or four on Sunday. You can leave then or stay for dinner, if you want."

"I will probably stay for dinner. I can either go back to school after dinner or early the next morning. I don't have an exam until one o'clock on Monday." I told her.

"Great. Thanks again. See you tonight or tomorrow morning. Love you!"

"Love you too." I replied and hung up.

My mom was going to Atlantic City for a quick weekend girls' getaway. Our neighbor Jackie had won a one-night stay at the Borgata Resort at some charity event and invited her to go with her. Since our dad had left us a few years ago I couldn't remember the last time she had done something for fun for herself. I was glad to see she was doing this.

Mom had asked me to make a surprise visit home this weekend. She didn't want my sister to be home alone by herself. She was a senior in high school and had turned eighteen last October. In the last year she had also grown up a lot. The skinny, shy girl had become curvy, tall, and outgoing. She had gone from cute to beautiful, even hot. With those changes her shyness had gone away and she was now outgoing and one of the popular girls at the school.

The result of that was lots of boys were interested in her. From what I could tell she didn't have a steady boyfriend but didn't lack for dates either. She had widened her circle of friends the last year also. Not all of these friends were a positive influence on her and she had made some decisions that mom wasn't happy about involving drinking and partying.

It seemed like over the last couple of months she was making better choices again but my mom didn't want provide a temptation for her to make a bad decision like having a party while she was gone. She also worried that if she wasn't home my sister would have opportunities to be alone with boys.

All of these were reason's I was heading home to be in the house over the weekend while our mom was out of town. When she had asked me to do it, I made her think I didn't want to and she was putting me out a little. What my mom didn't know I was excited to be going home. I was also sure she didn't know why I wanted to get there earlier than she expected. It was sort of related to all the changes my sister had gone through.

I felt my nervousness grown as I got closer to the place I was considering stopping at. I had partly timed my drive so I would be there right when they opened, thinking that would mean it would be less crowded. I had been in the store twice before and each time I was as nervous as I was now. I took the exit I needed and pulled into the parking lot.

There were a half dozen cars that I could see and I figured most of them belonged to the employees. I looked at the clock on the car radio and saw it was three minutes to ten. I considered driving away but convinced myself that the potential reward was worth the nervousness and any potential embarrassment I might experience. When the clock showed ten, I took a deep breath and got out of my car and walked to the entrance.

I held the door open for an older lady to enter who had got out of her car when I did. I stepped inside, hesitated and stopped and acted like I was looking at a piece of furniture that right inside the front entrance. Looking out of the side of my eyes I confirmed that what I really wanted to look for was in the same place and I slowly moved over to that area.

I did a fast scan and saw that there were a lot of possibilities. The hard part would be finding something that matched what I wanted and would work for me. The first several that I looked at were too small. Then I saw exactly what I wanted on the bottom shelf and at first glance they looked like they would work.

I took another quick furtive look around and kneeled down and pulled one of them off the shelf and looked at the sticker on the bottom. It had a ten on it and my heart beat picked up a little. I looked closer and the toe box looked fairly wide. There was no way I was going to try them on so I would have to risk that they would fit.

I grabbed the match and stood up. The hardest part was still ahead of me. In the short time I had been in here several other people had entered and as I moved toward the checkout counter, I felt like they were all looking at me. The woman I had held the door open for before was finishing up purchasing something, so I had a short wait.

My turn came and I set shoes on the counter. The woman at the register took a quick look at the bottom to see the price and then punched it into register. She told me what I owed with a sly smile on her face, I immediately handed her a twenty dollar bill. She got my change and put the shoes in an almost see through shopping bag and handed them to me with a wink.

I took the bag and forced myself to just walk out to the exit and not run. When I got to my car, I put the bag in the duffle bag that I brought out of my dorm room this morning and then jumped in the driver's seat and quickly pulled out of the Salvation Army store parking lot. My pulse was still racing.

The final hour of my drive home I focused on staying close to the speed limit. My nervousness about buying the shoes earlier was replaced with the anticipation of what I was going to be able to do when I got home. I didn't get many opportunities like this now that I was at college.

I pulled into the driveway and saw both my mom's and my sister's cars were gone. I am sure this caused me to smile as I reached into the back of my car and grabbed the duffle bag and headed to the front door. I wasn't surprised to find that my mom hadn't locked the door when she left for work, she seldom did preferring to trust society I guess.

I quickly stopped in the kitchen and grabbed a water bottle out of the fridge then bounded up the steps to my room. I tossed the water bottle and my bag onto the bed and went into the hallway bathroom to pee. I noticed that my sisters stuff was scattered everywhere in the bathroom, a definite sign that she had no idea I was coming home this weekend.

I went back to my room and looked at the clock on my bedside table, it was eleven twenty-five. I figured I had two-hour hours to do what I wanted and I would still have an hour safety buffer to get everything back to normal before my sister would be home. I went over to my closet, it was a small walk in one, and removed my suitcase and some cardboard boxes from the top of dark blue storage bin that was tucked in the back.

I took the top off the storage bin and pulled out the sweatshirts that were on the top of it. Below the sweatshirts were two bags that I removed and carried over to the bed. I opened the first one and pulled out a pair black closed toe pumps with a three-inch heel. Up until today they may have been my most prized possession. I sat them on the bed.

Next, I opened the other bag and removed the panties that were in it. There were two thongs, two bikini style pairs, and a pair of hip hungers in it. I had bought them at Victoria Secrets when they were having one of the five for twenty-five sales this past summer. I still couldn't believe I had built up the courage to do it. The sales girl, who couldn't have been a lot older than me, let me pretend I was buying them for a girlfriend but it was obvious we both knew they were for me.

I also pulled out one of the pairs of nude pantyhose that were in the bag. There were two pairs of nude, two black, and one pair of patterned tights. I had bought these at Target using the self-checkout while being sure everyone in the store was looking at me as I did it.

I set the pantyhose, and a black thong on the bed and then added my new shoes to that pile. I really wanted to try the shoes on but decided to get everything together before doing that. If they didn't fit, I would just put on my black pumps.

I moved over to my mom's room to get the next item. I felt guilty about doing it, but I hadn't come up with the courage to buy my own yet, I wasn't sure I ever would. I moved over to her dresser and opened one of the top drawers. The drawer was filled with bras. I knew I wanted one of her black ones and they were in the back so I reached into it pulled one out and took it back to my room and set it with the other items.

My excitement was building, and I quickly moved into my sisters room. Opening the door I was hit with some instant jealousy. Everything about her room said it was a girls room, compared to my room which said loudly... boring boy. I went straight to the far wall that had a double closet along it.

I opened the side that I knew would have what I was looking for and immediately saw it. I reached for the hanger and pulled it out. I was holding one of the most beautiful dresses I had every seen and carried it back to my room.

This was the dress my sister had worn to prom last weekend. It was a fit and flare, purple glitter, sleeveless dress with a square neck and a double hem, the bottom hem hit about mid-thigh. Or at least that is where it landed on my sister who, at just over five foot six, was a couple inches shorter than me.

My mom had posted pictures of her wearing it last Saturday on her Facebook page. As soon as I saw it I knew that I had to wear it. I must have looked at those pics two or three times every day dreaming about wearing it. It was what I looked at on my phone this morning to convince me to get out of bed.

When I got back to my room, I laid it on my bed with my other things and quickly removed my clothes. I was both a little nervous and super excited as I pulled my panties up my legs. I had an average sized penis and tucked it back as I settled my panties in place. I loved how the back of the thong set in between the cheeks of my butt.

I put my mom's bra on next. I chose hers over one of my sisters for two reasons. One, I felt funny about borrowing any my sisters undergarments, until this last year none of hers would have fit anyways so I was used to borrowing my mom's. Plus, my sister wore a 36C and my mom was a 38C. I was fairly skinny for a boy, but the slightly larger bra felt better.

I grabbed some of my socks and stuffed them into the bra to give it some shape and then rolled the pantyhose up my legs. I didn't have a lot of body hair but there was enough on my legs that I wanted to hide it.

I removed the dress from the hanger and undid the zipper and stepped into it. I pulled it up my body and slide my arms through the shoulder straps. Fortunately, I was flexible enough and the dress was just loose enough that I could reach the zipper and pull it up. Getting it unzipped was going to be a little tricky but I would worry about that later. I looked down at my thighs and realized it was short on me but not too short.

Next were my new shoes and I removed them from the bed and set them down on the floor. I tried to put them on while standing up but realized I would need to sit down to do it. I sat on my bed smoothing the dress behind me as I did and slid my foot into one shoe first and then the other one. I am sure a smile spread across my face when I realized that they fit.

I stood up and took some tentative steps. My black pumps had a three-inch heel and before that, when I could still fit in my mom's shoes, the tallest heel I had worn was three inches. This was a pair of platform pumps with a four inch heel.

After I was sure that I could move fairly easily in them I went into my mom's room and opened her closet door. On the back side of the door was full length mirror. I think I might have gasped when I saw myself, the dress looked amazing, and the nude heels were perfect with it. My sister and worn a pair of silver strap heeled sandals but I thought my shoes looked better.

When I looked at my hair and face, I was disappointed. I had slowly been letting my hair grow a little longer, but it barely covered my ears and just covered the back of my neck. My mom commented on what she was calling my hippie look every time she saw me. My dad had always made me cut my hair high and tight when he took me to the barber shop.

My face didn't have any pronounced male facial features but without make up I definitely wouldn't be mistaken for a girl. I was lucky that my lips were fairly pronounced and my facial hair was blonde and light. Not that I wanted to, but I couldn't grow a mustache or beard if I wanted. It would have just been a scraggly mess of hair if I didn't shave.

Besides the changes in her body over the last year or year and half, the other change in my sister was her use of makeup. She went from never using it to pretty much never leaving the house without it. She had also gotten very good at it. Her prom pictures were a testament to it and her eyes and lips just popped out in them.

I went back to my room and grabbed my phone. A quick trip to google and I was watching a video on makeup removal. I was watching it as I went into my sister's room and to her makeup table. I found the supplies I would need to remove it if I decided to try it. Next, I looked to see what makeup was there.

When I was in my early teens, I got into my mom's makeup one time. I had put on some of her lipstick and mascara. I remembered how amazing it felt to be doing it as I tried to copy what I had watched her do. When I was done I could see that I hadn't come close to copying her look and immediately washed my face.

Later that evening I had walked into the kitchen. Mom was home now and was prepping for dinner. She asked how school had been and what I had done that afternoon afterwards. I told her homework and played video games. The homework part was true but instead of video games I had tried on one of her dresses and used her makeup.

She had turned to me and smiled and then suddenly her facial expression changed. She looked right at my face and then grabbed my hand and told me to come with her. Still holding my hand she took me to her room and into her bathroom.

"We need to clean your face before you dad sees it." She told me before grabbing stuff from her bathroom counter. "Why were you using my makeup. It was mine, wasn't it?"

My heart felt like it was going to explode out of my chest. How do you answer that I remembered thinking.

"I uh... well... I was... bored. And I don't know." I had sputtered out.

"Well, if your dad saw it on you... I don't know what he would do." She told me as she focused on removing all the mascara from my eyelashes.

I didn't respond and just nodded.

"If you want to use it in the future just ask me. I can help you and make sure you also get it all off. Okay." Mom said when she finished and gave me a hug.

"Uh... okay. I doubt I will want to do it." I lied to her then and quickly left her room.

I remember I was surprised at my mom's reaction and her offer. I would have loved for her to help me with makeup but I had never asked her. After my dad left us a couple years later, I thought about it several times but could never find the courage.

I easily found my sister's mascara and lipstick. There was also foundation, eyeliner, eye shadow, a whole table of it was in front of me. I wanted to try all of it but thought I should stick with just mascara and lipstick. As I put them on a feeling washed over me. I actually felt like I was girl at the moment.

When I was done, I was happy with what I saw in the mirror. My lips really stood out and the mascara had changed my semi androgynous appearance to a girly one. If I could so something with my hair I might actually pass as girl, I thought.

I got up and went back to mom's room and her mirror. I was really happy with how I looked and spent a few minutes turning and twirling in front of it. I remembered I had left my phone in Chrissie's room and went back for it. I nervously brought up the phone app and then took several selfies.

When I went to look at the pics I was positive that some how one my fingers would hit something and post a pic to social media or send one via text. I began to delete the pictures but then decided I wanted to keep at least a couple of them.

I looked over at my mom's bedroom clock. It was twelve thirty so I had at least an hour where it would be completely safe to stay dressed. I wanted to be undressed, make up removed, and everything back in its hiding place or my sister's closet by one thirty. My sister got home around two thirty.

I looked down at my shoes and thought I wanted to see how well I could move on the stairs wearing them. Plus, if I went down stairs I could hear the sound of the heels on the hardwood floors in the living room and dining room plus on the tile floor in the kitchen.

With my phone in one hand, I moved to the stairs. I was able to fairly easily descend them. I just focused on making sure each foot landed in the middle of the stair with each step. When I got to the bottom, I moved through the foyer into the living room. Each step sounded wonderful to me, and I made a couple laps loving seeing myself in the mirrors that I passed.

I decided I was a little thirsty, plus I kind of wanted to see my lipstick on a glass, so I moved to the kitchen. The change in sound from heels on the hardwood to the tile wasn't substantial but I still liked hearing it. I got a glass out of the cabinet and went to the refrigerator used the water dispenser in the door.