Maybe Someday - Cover

Maybe Someday

Copyright© 2007 by Cindy for Sin

Chapter 1

Romantic Sex Story: Chapter 1 - "For as long as I can remember I have worshiped my older brother, and I have fond memories of my early childhood as we grew up together."

Caution: This Romantic Sex Story contains strong sexual content, including mt/ft   Teenagers   Consensual   Heterosexual   Brother   Sister   First   Oral Sex   Petting   Slow  

For as long as I can remember I have worshiped my older brother, and I have fond memories of my early childhood as we grew up together. Kevin is eleven months older than me. Because of when our birthdays fall, we were in the same grade in school. Our parents are accounts and have their own business.

We live in a nice four bedroom colonial located on a cul-de-sac in a quiet neighborhood in south Florida. The house has three bedrooms and two bathrooms on the second floor. The master bedroom is on the first floor with its own private bathroom. Along with the master bedroom, the first floor has the kitchen, dinning room, living room and an office. Our walk-out basement, only available because our house was built into the side of a manmade hill, is finished. In the large treed backyard, there is a deck and an in-round swimming pool.

Even though they were very busy with their practice, our parents always made time for Kevin and me. Dad and Mom taught us to swim when I was five and my brother was six, the year we moved into the house. I can still remember the evenings in the pool with our parents helping us learn to swim.

Kevin and I played together, always getting along. He was willing to play dolls with me and I would play cowboys and Indians with him. Even when Ellen, my friend from next door was over, Kevin would play with house or dolls with us. Kevin's best friend lived two doors down. Larry didn't like playing with Ellen and me, but Kevin had a way of convincing him to join in.

Mom bathed Kevin and me together until I was seven. When she told us we were too old, we didn't question her. At first I missed out tub time, but quickly got over it. By the time I was eight and Kevin was nine, we were showering.

While our parents worked, my brother and I had a nanny. Mrs. Hebert was very nice and fun to be with. She arrived every morning to help Kevin and me get ready for school. We ate breakfast as a family and then Mom and Dad would leave for work. Mrs. Hebert took us to school and picked us at the end of the day. In the summer, my brother and I played.

My story begins on a Saturday afternoon. It was during summer break and Kevin and I were in the basement with my friend Ellen. The basement was a divided into a huge recreation room, the furnace room, a changing room with a bathroom and a playroom. Kevin and I were in the playroom having a tea party. I was eight and Kevin was nine.

"Would you like more tea?" I asked as I poured water from a teapot into my brother's cup.

"Yes, please," Kevin replied. When the cup was full, he said, "Thank you, Amber."

We were taught manners and talked politely even when we played.

"May I have some more too, please?" Ellen asked as she sat across from Kevin grinning.

I filled her cup and then sat down. We sipped from our cups and chatted. That day, Kevin and I were husband and wife. Ellen was pretending to be a neighbor. On the floor, we had dolls set up and pretended they were our children. Ellen got up from the table, went to the dolls, and picked one up.

"My, my, Lorie, your diaper needs changing," Ellen said. She placed the doll on its back and began undressing it.

"Kevin, you should check Gail, she might be wet too," I said.

Kevin knelt on the floor and changed the doll. He made a fuss over her, talking baby talk to her while changing the doll's diaper.

"Don't forget to use a wipe and powder," I told my brother.

"Amber, I know how to change a baby!" my brother said.

Kevin did know how, he had done it many times when we played. I watched as he used a tissue as a wipe and then put powder on the naked doll. He put on the diaper and redressed our make-believe daughter.

"There you go, all nice and dry," Kevin said as he placed the doll on the floor with the others. Ellen finished her doll and returned to the table.

We played house for an hour. Kevin said he wanted to play outside for a while. Ellen and I agreed, knowing we would be squaws and Kevin would be a cowboy. When Kevin and I played cowboys and Indians, we usually wore costumes. Our mom had made us the costumes for Halloween a couple of years earlier.

My costume was a brown dress that looked like it was made from leather and a headband, while Kevin had a complete cowboy outfit, including two six-guns. Before going outside, I had Mrs. Hebert braid Ellen's and my hair. In the backyard, the game was played out as it always was. Kevin would capture Ellen and me. He tied us to a tree and told us he what he was going to do to us. As always, Ellen and I pleaded for our lives.

When we tired of playing cowboys and Indians, we went swimming. Mrs. Hebert sat by the pool watching us playing in the water. If Kevin's friend came over, we would play Marco Polo. Our summer days were almost always the same.

On the weekends, Kevin and I went shopping with Mom while Dad played golf on Saturday mornings. In the afternoon, we would always do something as a family. We went to the movies or to several different places where Kevin and I could play. On Sundays, Mom and Dad worked in the yard.

As we got older, Kevin became less interested in playing house with me. He would put up with it once in a while, but not on a daily basis like before.

The year I was nine and Kevin was ten, I was playing with Ellen while Kevin and Larry played by themselves most of the time. The two boys played outside most days and Ellen and I played in the playroom. About the only time we played together was when we went swimming.

On one hot August afternoon, we were forced into the house because of a thunderstorm. The four of us had been in the pool, but Mrs. Hebert made us come in when she heard thunder. Kevin, Ellen, Larry, and I took turns in the changing room, each of us putting on our clothes.

"What do you guys want to do now?" I asked.

"We could play a game," Kevin said.

"Why don't we play house?" Larry said.

I thought it was strange Larry wanted to play house. He never really liked playing like that. The four of us agreed to play. We went into the playroom to begin.

"Okay, Ellen and I are the mom and dad. You and Kevin are our kids," Larry said.

We had never played that way before. In the past, my dolls always served as the kids.

"Why can't Amber and I be the parents and you two be the kids?" Kevin said.

"You can, when it's your turn," Larry replied.

Larry was the oldest in our group. He had turned eleven in July, three months before my brother would have his eleventh birthday. Taking charge, Larry began setting the scene. He told Kevin and me to sit on the floor while he and Ellen sat at the table.

My brother and I drew and colored on blank paper while Larry told Ellen about his make-believe job. Ellen told Larry what she planned to make for dinner and about her day. After about ten minutes of play, Larry stood up.

"Honey, I think the kids need their diapers changed," Larry said. "You change Kevin and I'll change Amber."

Kevin and I looked at each other. I wasn't sure what Larry had in mind and I was sure my brother didn't either. Larry had a big grin on his face, but Ellen didn't look very excited about doing what Larry was suggesting.

Meekly, Ellen asked, "What are we going to use for diapers?"

As I thought about what lie ahead, I began to get curious. Jumping up, I ran to the changing room, retuning with two hand towels. I dropped the towels on the table and sat on the floor with my brother.

Larry's grin grew. He took one of the towels and knelt next to me. Ellen watched for a moment before she picked up the other towel. When Larry guided me onto my back, I let him. Ellen did the same to Kevin.

"What are you doing?" I said when Larry began unbuttoning my shorts.

"You can't talk, you're too young," Larry said as he worked at my shorts. "Just be still so I can change your wet diaper."

I giggled. When Larry began tugging at my shorts and underpants, I lifted my butt. Next to me, Ellen did the same to my brother.

Ellen giggled when she pulled Kevin's pants down. I glanced at him, giggling when I saw his penis standing up. It had been a while since I had seen him naked and he was never in the state he was in when I did.

"Make sure you clean him real good," Larry said as he wiped between my legs with a tissue. "Don't forget to use the powder either."

I giggled when I felt Larry wiping me—it tickled. He lifted my legs, rubbing my bottom with the tissue while telling me to hold still. Larry shook some powder on me and used his hand to rub it over me.

Ellen applied powder to Kevin, smoothing it with her hand. I watched my brother wiggle as her hand rubbed his penis. Once Kevin and I had the powder on us, Larry and Ellen formed the towels into makeshift diapers. They used our underwear for plastic pants, pulling them over the diapers.

Larry pulled my shorts up. Ellen redressed Kevin and we went back to our play. It felt weird having the towel on, but not as weird as it felt when Larry was touching me.

We played for a little longer. I said it was time for Kevin and me to be the parents. Kevin and I left the play room so we could remove the towels. Taking turns in the bathroom, my brother and I took off the towels and then went back to the playroom.

Larry and Ellen took on the role of the kids. Kevin and I changed them, repeating what they had done to us. While applying powder on Larry, I was surprised at how his penis felt against my bare hand.

Mrs. Hebert called for us, telling us she had prepared snacks. Kevin and Ellen had just returned from removing the towels so we weren't caught.

Later that afternoon Ellen and I had a chance to talk. We were in my room while Larry and Kevin were downstairs.

"That was fun, wasn't it?" Ellen said.

"Yeah, it was really fun. Did you like touching Kevin's wiener?" I replied.

"It felt funny. Did Larry's wiener feel funny too?"

"Sort of. It tickled when he touched me down there," I said, pointing at my crotch.

"Me too, but it felt nice too," Ellen said with a giggle. "I didn't know a boy's wiener was so hard."

"Neither did I. I used to see Kevin's when we took baths together, but it was never hard."

"Um, would you do that again, you know, play like we did?" Ellen asked.

"Would you?"

Ellen and I giggled as we nodded our heads.

The four of us played house a few more times that summer. It was always the same, Larry and Ellen were the parents and my brother and I the kids. When we switched, Kevin and I played the parents.

One night, after school had started, Kevin and I were sitting in the recreation room watching television. He had turned eleven a week earlier. While sitting on the couch near my brother my curiosity got the best of me.

"Kevin, is your wiener always hard like when we play house?" I asked.

"Um, no, not always. It gets that way when we play though," Kevin told me.

"Does it hurt when it's hard?"

Kevin laughed and shook his head.

"I think playing house is fun, do you?" I asked.

"It's okay."

"Do you like it when Ellen touches you there?"

"It feels funny sometimes, like I have to pee," Kevin told me.

"Can I see it?" I asked. "I'll show you too," I quickly added.

Kevin shrugged his shoulders. He stood up and pulled his pajama bottoms down so I could see his penis. I also pulled my pajamas down so he could see me. We stood a few feet apart, each of us staring at the other. While we looked, our mom came downstairs and caught us.

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