Amanda

"Hey Jared," my sister Amanda said.

"Oh, hey Amanda. What's up?" I said.

Even though Amanda was my sister, we never had a lot of small talk.

"Not much. Just enjoying the last few days of summer break," I said.

It was early August and the private school we went to started earlier than usual. Amanda and I were both 18. We already had our uniforms and supplies. Our parents were out of town at their 20th high school reunion.

"So, want to help me?" Amanda asked, "I have do the laundry and you need to help. I've done over half the list."

"Sure, I'll be down in a second," I said, logging out of Facebook.

I knew better then to not help. I had once not mowed the lawn one week and got grounded for a week. I walked down the laundry room to see Amanda bent over pulling some clothes from the dryer with her butt in the air. Now would be a good time to describe us. Amanda was taller with dirty blonde hair. She was no Victoria Secret model, but she was pretty good looking. She usually had a boy around her, but not now. I was a bit smaller then Amanda, not overly muscular with longer hair.

"Alrighty, what do you want me to do?" I asked.

"Fold these while I put in the next load," Amanda said walking over with a load of colorful laundry.

She plopped them down on the little table and walked back to the washer. I picked up the piece of clothing on top of the pile.

"What is this?" I asked, holding out the skinny piece of clothing.

"That is one of my thongs. I already washed and folded all of your clothes and now you're going to help me with mine," she said, not even stopping from her work.

"Ok," I said going back to her panties.

There were many different types of her panties to fold. Some were just three strings and some had colorful lace. Some were just one color while others had colorful designs.

"So, do you like them?" Amanda asked.

"Um, yeah? They are really colorful," I said jokingly.

"You should put them on them," Amanda said, with a tone of seriousness.

"Oh, um I was...," I trailed off because of the look she was giving me, so meekly; I asked "which one?"

"Go run upstairs and put this one on," she said smiling, tossing me a red thong with a black bow on the front.

I quickly walked up the stairs into the bathroom and locked the door. I stepped out of my baggy shorts and pulled off my boxers. I stepped into the panties and started to untwist them. I slowly pulled them up my legs till I reached my penis. I tucked it down, bending it to face backward. I then snuggly pulled up my new panties till they were in place. I took a minute to feel my penis through the silky material. I quickly slid my shorts back up my legs and walked back down.

"How do they feel?" Amanda asked, looking up from her task.

"Different," I said.

I stood there and she just looked at me for a few seconds. Then she looked down at the pile and back at me.

"Do you like wearing them?" she asked.

"They're different I guess," I mumbled.

"Oh, alright. Help me take these up to my room," Amanda said, taking her neatly folded panties in the hamper.

I followed up the stair behind her to her room, the entire time getting used to the new sensation of the panties. When we got to her room, she went over to her stand up dresser and I sat down on her flowery bed. She turned around and looked at me again.

"Here," she said, tossing me a small pink thing, "get out of those shorts and put on this. If you're going to wear panties, you might as well wear more."

"Oh come on Amanda," I started pleading, "why do I have too?"

"Oh you can decide not to. But I was thinking of having some friends over later. SINGLE friends," she whispered seductively, "If you want to be invited to meet them, you may want to listen."

"Alright," I said and I walked out of her room and walked to the bathroom.

Although it my have been embarrassing, I had been single for a bit too long, I wasn't letting this opportunity pass by. I dropped my shorts and put the pink bundle on the counter top. I stepped out of my sports shorts and picked up the piece of clothing. It was short shorts. They were from the Victoria Secret PINK with the word slut across the butt. I stepped into them and pulled them up till I felt it enter my crack. The red trim on the bottom of them came down to my mid-thigh and left me feeling exposed.

"You look good in those," my sister said as I reentered the room.

"Thanks," I said sheeply.

"Two more things I want you to wear," Amanda said.

She tossed me two more articles or clothing and I left with them. Arguing was now pointless with a reward of hot single friends at the end. When I got back into the bathroom I took off my shirt and picked up the black piece of clothing. It was a bra. I slid my arms through the arm holes and fumbled to get it hooked in the back. It must have been padded because it was heavy and when I looked in the mirror, I had small boobs. After I got it hooked, I picked up the white tank top and forced it on. It was a tight fit. With the material stretched, you could clearly see the bra through it and the spaghetti straps couldn't hide the bra straps. I smoothed out my new clothes and walked back to my sister's room.

"Well you just look adorable. Do you like your new outfit?" Amanda asked with a twinkle in her eye.

"Um, kind of?" I said, feeling very self-conscious.

"You look good. So, it'll be a few hours till my friends are here. You may want to mow the lawn," Amanda said.

"Yeah I probably should," I said, reaching for the pile of my guy clothes.

"Not so fast. You should mow the lawn as is, if you want to meet my friends," Amanda said sternly, giving me the strict look.

"But come on! Doing it for you is one thing. Out there it's another!" I reasoned.

"Oh don't be a little girl! All you have to do is the back yard, which is fenced in completely! Nobody will see you," she shot back, killing my chance of winning.

"Alright," I said, turning to walk out of her room.

"Not so fast cowboy. What she size are you?" Amanda asked.

"5," I said sheeply.

I wasn't the biggest guy in my school. Puberty had yet to hit me, leaving me a runt. I had still not shaven.

"Oh good. My shoes will fit you. Here. These are fish net stockings. Go take off your shorts, put these on, put back on your shorts, and then put on these, my pink converse," she instructed me.

I quickly did as I was told and changed. When I was done, I cautiously went to the backdoor. Opening it slowly, I peeked my head outside. Empty. Good. I quickly jogged over to the shed and pulled out the push mower. I spent the next hour in total humiliation mowing the lawn. When I was done, I quickly put away the mower and ran back into the house.

"I'm done," I yelled into the house.

"Ok, good, now come up here," Amanda yelled from her room.

I kicked off my shoes and walked up the stairs to Amanda's room. I got up to her room and knocked on the door.

"Come in," she said.

I entered her room, which was just cleaned, and looked around. Her room was mostly pink and had small red flowers. Her bed was white with different colored flowers on it.

"Ok. You have a couple choices here. You can have your nails done or your make up done. Now for your clothes. You can wear this black skirt with panties, bra, tights, and wig or you can wear my new bikini with high heels," she said.

"Oh. I thought I could just change... I'll choose nails and bikini I guess," I said, hoping to avoid wearing a skirt.

"Alrighty. Here ya go," Amanda said, tossing me her new bikini, "and when you get back, I'll do your nails."

Once again, I returned to the bathroom. Although I would never admit it, I was enjoying the attention I was getting from Amanda. I stripped out of my slutty out fit and picked up the bikini bottom. That's when I knew I made the wrong choice. The bikini Amanda had given me was small. And black. I stepped into the bikini and pulled it up quickly. I tucked my penis downward and realized another problem. My erection wasn't completely held down by bikini. And it had the word "slut" written across the butt in pink. I picked up the bikini top and slid into it. I grabbed my discarded clothes and walked back into the room to see Amanda had changed clothes. She had on a white mini skirt with a white tank top stretched over her green bra. I had never really seen Amanda's true beauty till now.

"Um can I change my choice?" I asked, self-conscious of how much of my skin was showing.

"Nope. Your choice! And here are your heels. They should fit you," Amanda said in her ever so cheerful way.

I took the heels and sat down on the side of the bed. They were only about 1 inch and were very lacy black. After I had got them on tightly, I stood up on my wobbly legs.

"I'll make you a deal," said Amanda, "you don't have to wear the heels if you let me do your make up."

"Sure! I can hardly stand in these," I said, feeling more and more desperate in my situation.

"Ok. Take off your shoes and we will do your nails. Then while they are drying we will do your make up," Amanda said reaching into her dresser and pulling out a nail kit.

I tore off my heels and sat down on the bed waiting. Amanda slowly started to paint my nails a light pink. Once she got done with my finger nails, she moved onto my toenails. She quickly applied the rest of it and then let them dry while she put away the nail kit. They dried a subtle, but noticeable hot pink.

"Now it's time for your make up!" Amanda said excitedly, "Now do you want it obvious or not noticeable?"

"Not noticeable," I said.

"Alright, noticeable it is," Amanda said, giving me a big smile.

She spent the next few minutes painting my face with different colors. I ended up with red lips, light pink eye shadow, noticeably plucked eye brows, and heavy mascara.

"You look fabulous!" Amanda said.

Then the doorbell rang...