Big Help from Lil Sis Pt. 02

Big Help from Lil Sis- Part 2

Part 2 of a three-part story. All characters are over 18 years old.

I heard a light knocking on my bedroom door that woke me from my sleep. I opened an eye and saw it was just after eight o'clock. I am not sure how long it had taken me to fall asleep but I remembered scanning my mom's Facebook around midnight. I was looking for pics of Kelly and the different outfits she was wearing in anticipation of possibly getting to wear some of them myself today.

I mumbled a yes and the door slowly opened and my mom's head peaked around the side of it. She had a big smile on her face. I sat up in bed which she took as sign to come into my room and strolled over and sat on the end of the bed.

"Good morning Adam, sleep good?" She asked.

"Morning, uh... yea. Struggled a little to get to sleep. But yea..."

"What did you do yesterday? You got home way earlier than I thought you would. I saw Chinese in the trash can did you eat dinner with Kelly?" There was a sound of surprise in her voice about the possibility that Kelly and I ate together.

I couldn't tell her the truth. That I had dressed up in Kelly's prom dress, she caught me, took me shopping for bras and panties, we ate dinner together, watched a movie on TV, she painted my toe nails, oh and we had talked about sex.

"I uh took advantage of the quiet and did some studying for finals next week. Kelly was going to go out with her friend Lisa, but something came up, so we just ordered Chinese and watched a movie." I lied except about the Chinese and movie parts.

"Well thanks for coming home. It is going to make it a lot easier for me to enjoy the weekend. Come on down and let me make you some pancakes before I head out." Mom got up and walked out of the room.

I swung legs out from under the covers and got out bed. I headed over to the bathroom to pee, brush my teeth, and wash my face. When I came out I ran into Kelly in the hallway. We shared some awkward smiles passing each other. I could smell bacon cooking down stairs and headed to the kitchen, making sure my Crocs covered my toe nails.

When Kelly came down mom and I were finishing up a conversation about how college was going for me. I was doing pretty well, and my grades were good. I moved over and sat at the table and mom put out plates with pancakes and bacon on them. Kelly grabbed a seat also.

"Were you surprised to see Adam when you got home yesterday? He didn't even tell me he was going to come home this weekend so he could study in peace." Mom said to Kelly.

"Oh... yes... it was definitely a surprise when I saw him, that is for sure." Kelly fought a snicker as she answered.

"Sounds like you all had a nice evening. I am glad to see you all getting along a little better it seems. Maybe you just both needed to mature some and realize you had some things in common."

I felt my cheeks get red and looked down at my plate. I think Kelly had to fight snarfing the orange juice she had just drank at mom's comment about us having some things in common.

"So, you know the rules, Kelly. Still the same, no parties while I am gone and no boys allowed in your room. And I know you are both over eighteen but if you go out I still expect you home no later than one o'clock in the morning. Got it?" Mom tried to sound firm as she spoke.

We both acknowledged what she said. She gave us a run down of her plans for the weekend and said she would be home late in the afternoon or early evening on Sunday. I was asked to stay at least until after dinner that night and I agreed I would. Kelly told her that we would clean up the kitchen and that she could finish getting ready to go.

Right at nine-thirty our neighbor knocked on the door. Kelly yelled up to mom that she was here and I went up and got mom's suitcase for her and carried it down stairs. When mom came down both Kelly and I did a double take. She was wearing tight fitting sundress and had put her makeup on heavier than normal.

"Wow... you look... great mom. That dress is amazing. Is it new?" I said when she got to the door.

"You look hot!" Kelly gushed.

"Stop you two... hot... as if. Behave yourself okay. I will see you tomorrow." Mom gave each of us a hug, picked up her suitcase and headed out the door.

"That dress is amazing. Is it new? You might as well have just said I am really a girl mommy." Kelly said to me after mom walked out and the door closed.

I didn't respond and went and finished up cleaning the kitchen. I was hoping Kelly would bring up me changing into girls things and working on my makeup. Yesterday she had also mentioned doing something with my hair to make it look a little girly.

When I was done I went out into the family room but Kelly wasn't there. I then headed upstairs and saw that her door was closed. I lightly knocked on it and heard her moving across the room to open it.

"Yes?" She asked.

"I uh... I was just... um..."

"You are wondering when you can start playing dress up?" Kelly smiled at me.

I just nodded.

"Go take a shower. While you are in there use my shampoo and conditioner. I also want you to shave your legs, under your arms and any other place you have hair that a girl doesn't. Make sure you do a good job on your face and get that as smooth as possible. Oh... and if you don't already... might want to shave your... uh... personal area. Most girls do that now days."

"If... I shave me legs... um... won't people see that? Like my roommate." I asked nervously.

"Maybe... but do you really think people look that closely? And you are the one that wants to dress and look like a girl, right. Girls shave those places. Honestly, I think you are going to like how it feels to do it." Kelly smiled.

Again, I just nodded and moved off to the bathroom to follow her instructions. I was surprised at how much I liked using her shampoo and conditioner. The scent was wonderful compared to what I normally used.

I grabbed her shaving cream and razor and started on one of my legs. I was pretty nervous about what I was doing, partly worrying that I would cut myself, partly worrying what people would think and say about my hairless legs. My sister was right though, I loved how my legs felt when I was done.

I next did my underarms. This felt trickier but it added to the feeling of femininity that was I experiencing that had started with using Kelly's shampoo. With my legs and underarms done I removed a small patch of hair in the middle of my chest and another below my belly button. I finally made sure that I was smooth any place that would be covered by panties.

I finished my shower and stepped out and dried off. Again, loving the feeling of my smooth legs. Kelly had told me to make sure my face was as smooth as possible, so I shaved that next. I was a little disappointed watching myself do that in the mirror as I thought that girls don't have to shave their face.

I left the bathroom and went over to Kelly's room. The door was open, and I started to step in.

"Stop!" Kelly yelled out.

I startled and froze. She walked over to me and reached for my towel. I was shocked as she undid and then brought it up from around my waist to up under my arms and tucked it in tightly.

"There you go. That is how a girl wears a towel. Remember mom said that no boys were allowed in my room this weekend." She smiled and winked at me.

I laughed, but at the same time I felt a change run through me with just the repositioning of the towel. I did feel more girly.

"How did the shaving go? All smooth?"

"Yes... I shaved everything you told me to." I responded.

"Good. Sit down in that chair and take a second to put this lotion on your legs. It will feel good and help to prevent itching." Kelly handed me a bottle.

"Do I put this everywhere I shaved?" I asked tentatively.

"Well... if you are asking what I think you are, I have never shaved those, because I don't have them, but I when I shave... I put lotion everywhere I shave." She had accented the word those and winked at me.

I followed her instructions, again enjoying the scent of her lotion. The feel of my hands running over my now smooth legs was awesome. I was already thinking that hairless legs were going to be a part of my life forever, regardless of what I was wearing.

"Let's go to mom's room. I want to work on your hair, and she has some gel in there. Or I hope she does and didn't take it with her."

When we entered mom's room she went into her closet and stepped back out and handed me a floral printed silk robe. I turned my back to her and removed the towel and slipped into the robe. I loved how it felt. It landed pretty high on my thigh, and I knew I would have to be careful to not accidentally flash Kelly.

We went into the master bathroom and Kelly was able to find everything she wanted. She put different things in my hair and then started with the blow dryer and some brushes. My hair was fuller, and she was able to sweep it back into a style and look that was definitely feminine.

"Wow... I should have paid more attention to what you were doing." I said looking the mirror.

"I actually impressed myself. That looks really cute on you. So, I have a thought about today, actually I have several, but I am going to start slowly and build up." Kelly laughed.

"Okay... what is your thought?" I asked a little nervously.

"I am going to help you do your makeup and then you are going to play dress up for a while. This is your chance to raid my closet and wear anything you want. After we do that, we will eat lunch, then I will tell you what is next." She smiled at me.

"I like the first part of this. A little nervous about the what is next part." I said honestly.

"Good... that will make it fun. And don't forget tonight I am having a small party. You can decide later how you want to dress for that." She winked at me.

"All good as long as it is small, and I am planning on hiding in my room during that, so it won't really mater what I am wearing." I smiled at her.

Kelly led me back to her room and sat me down at her makeup table. She explained that she was going to go heavier on the makeup this morning. She started with a foundation, commenting that our skin tone was similar so hers worked perfect on my face. She did one side, and I did the other with her instruction. I was surprised at how much my check bones stood out and how that feminized my face.

"Um... can I thin out these eyebrows a little? Nothing to drastic but they are a little too... I guess too much for a girl."

"I guess... do you think it will really matter and will I be able to look like a boy still?" I asked nervously.

"Yes, and yes." She said picking up her tweezers.

It was little painful as she plucked the hairs but when she was done I had to agree it had made a difference. It wasn't drastic but made a difference. Kelly saw my smile and smiled back and squeezed my shoulder. She then picked up an eyeliner pencil and did one eye and I tried to copy it on the other eye. The same pattern was repeated for eye shadow and mascara.

We finished by doing my lips and when we were done I saw a young woman looking at me in the mirror. Actually, I saw a very pretty young woman looking back at me. My emotions took over and my eyes began to fill with tears.

"Hey... are you okay? You are going to fuck up all our work." Kelly said.

I fought back completely breaking down and stood up and hugged her. When we broke apart she continued to hold my hands in hers, squeezing them gently.

"I have dreamed about this... pretty much everyday for the last five or six years. Then I had to watch you get to live my dream and I really hated you for it. I am so sorry for how I treated you." I told her as the tears began to form again.

"Yea... you were a real cunt to me. At least now I know why, and I understand it. I accept your apology but if you don't stop the crying and you ruin our work on your makeup, I am taken that back, bitch." Kelly said looking right at me with a small smile.

I pulled her into another hug as I both laughed and felt a warm emotion spread through me. We separated again.

"So, when you were dreaming about this what name did you dream about? I don't know to many Adam's who are this are pretty?"

"Uh... Addison... or Addie for short." I chuckled.

"Oh... I love that. Well Addie time for your first outfit. Go grab the breast forms and a bra, plus slip on some panties and then come back here."

I followed her instructions. Picking out the pink bra and panties. I understood why I had gotten the white bra, but I knew I would probably only wear it if I had a white top on. I slipped into the lingerie and set the forms in my bra and then put the robe back on. I definitely wasn't ready to parade around in my undies in front of Kelly.

When I walked back into her room there were several outfits laying on her bed. My eyes immediately went to her cheerleading outfit and when I looked up, I could see a grin on Kelly's face.

"Yea... I thought you would want to wear that one again. Outside of a wedding dress, which I don't have one of by the way, but mom does, nothing says girl more than a cheerleading uniform."

Kelly and I giggled about mom's wedding dress. I had actually thought about trying it on several times but never got past going to the back of her walk in closet and opening the bag. I was sure that if pulled it out I would damage it somehow. Although, since our dad had walked out on us I doubted it had a lot of sentimental value to her now.

Kelly handed me the skirt and the spanky pants for her uniform and told me to put them on. I started to walk out of the room.

"Hey Addie... this will be easier if we lose the modesty. I promise I won't perv on you when I see you in your underthings." She laughed.

I nervously laughed and undid the robe and sat it on the bed. Kelly commented that I picked pink for my bra and panties. I stepped into the spanky pants and then the skirt. The time I had worn he cheer uniform before I hadn't zipped it up all the way, I was afraid of breaking the zipper.

"Suck in." Kelly instructed and she grabbed the zipper and pulled it up.

It was definitely tight on my stomach but I was able to fit in it. Next, I pulled the mock turtle neck over my head. I was worried I was messing up my hair but a quick glance in the mirror showed it was fine. The shell went on next and suddenly a high school cheerleader was seen in the mirror on my sisters closet door.

I turned around and Kelly had her phone out and was taking pictures. I immediately got paranoid and started to say something when she told me to relax, she was taking them for me and would delete them immediately after sending them to me. I was able to control my nerves and was smiling broadly as she coached me through different poses.

For the next two hours we followed the same routine. I would dress in something she or I picked out and then she would take pictures of me modeling what I was wearing. I focused mostly on her dresses, including her prom dress from the previous year, and her skirt outfits. I really liked her skater skirts and tartan skirts. My black pumps seemed to be a perfect match for them.

Just before lunch she had me pull on a pair of leggings and a simple scoop necked t shirt. We went down to the kitchen to eat. It felt weird to be walking through the house while not being scared of being caught in girls' clothes at any minute.

"Thank you, Kelly. This morning was amazing." I told her before biting into my tuna fish sandwich.

"You are welcome. You know you are a natural diva, right?"

"What... what do you mean?"

"Your face just lights up when you put on something pretty, or glamorous, or even sexy. The way you move, it is almost like you are a model, and did you spend every second you were home alone prancing around in heels? You walk like you were born with them on your feet?" Kelly responded.

I took most of that as a compliment and smiled although the prancing part made me a little nervous. It was the second time she had used that word since she caught me. Was that a shot at me? I had felt safe all morning but that put me a little on guard.

"Tell me a little about this party tonight. Who is going to be here? Is the guy you went to prom with coming?" I asked.

"No... Prom didn't end the way he wanted so he has pretty much ghosted me since then."

"Oh... I am sorry. Uh... how did he want it to end?" I asked although I was pretty sure I knew.

"With me naked, on my back, him between my legs, and his dick in me for two or three minutes. And no need to be sorry, I wasn't really that into him although he is pretty hot. He is going out west for college so we didn't really have a future anyways." Kelly's tone was flat.

"So, he got mad because you wouldn't have sex with him? Sounds like he is an asshole." I was shocked that Kelly was being so blunt.

"Thing is... I would have been happy to suck his dick, even told him that, but he felt like taking me to prom was a guarantee I would fuck him. Boys can be real assholes." She laughed.

"Are you... um... are you virgin?" I asked.

"No... that ended not long after I turned eighteen. You aren't a virgin, are you? I mean I know you told me you haven't hooked up with a guy yet but how about girls."

"No... I am not a virgin." I said looking at the ground.

"Do you like having sex with girls?"

"Sure... it feels good." I told her.

"But... it feels like there is a but in that statement." She smiled as she said it.

"Maybe... I don't... umm... lots of times I wonder what it would feel like if I was the girl... or maybe I wish... I wish I was the girl when doing it." I didn't look at her as I spoke.

"Well, most of the time it doesn't last long enough to really feel much at all. Part of the reason I prefer giving blow jobs. More control and if you suck them off first, they will last longer... or at least in some cases... when they fuck you."

I was really shocked listening to Kelly tell me these things. Prior to yesterday we had never talked about sex and now she wasn't holding anything back.

"Um... do you... well... uh... do you... or have you... do you have a lot of... experience?"

"Are you asking me if I am a slut?" She laughed hardily.

"No... sorry. It is none of my business." I replied sheepishly.

"I don't think I am a slut... or at least when it comes to being fucked. I have slept with two guys. Uh... when it comes to cock sucking... maybe I am... kind of. I just really like doing that." She winked at me.

We had finished our sandwiches, so I stood up and grabbed our plates to rinse off and put in the dishwasher. When I had done that I turned back towards the table and I saw Kelly look at my crotch and smile.

"Uh... guess our talk got you a little worked up, huh. We need to figure out a way to hide that if you are going to wear leggings, or even tight shorts." She giggled.

I looked down and could see a slight bulge in the front of my leggings. I am sure my face turned red and I quickly sat back down and slide my legs under the table to hide it.

"I hope that didn't happen because you were thinking about me having sex. That would be a little... well perverted. Hopefully it was because you were thinking about sucking a dick." She laughed.

"Of course not. The first part I mean. The second part... maybe." I grinned.

"Okay... time for part two of the day. I know you are going to say no when I first tell you my plan but then I want you to take a few minutes and think on it and if you still say no I will accept that but I think it is a mistake if you do." She had looked right at me the whole time she said that.

"Okay. I am listening."

"I think we should go out, while you are dressed as a girl."

"No way!" I immediately said.

Kelly laughed. "You didn't even let me finish saying what we were going to do."