Who Would Have Guessed - Cover

Who Would Have Guessed

Copyright© 2018 by Cindy for Sin

Chapter 1

Incest Sex Story: Chapter 1 - My sister and I embark on a sexual adventure.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   Incest   Brother   Sister   Anal Sex   Masturbation   Oral Sex  

I sat in the auditorium listening to the speech the valedictorian of my graduating class was giving. Because we sat in alphabetical order, my seat was in the front row. Our class was two hundred forty-three strong.

The school was private and co-ed. As my parents had, my sister Deanne, Dee to her friends and family, and I attended the exclusive school. In fact, our grandparents and my parent’s siblings all went to school at Hartford Academy. I wanted to go to another school, but my father wouldn’t hear of it. He felt it was important that my sister and I continue the family tradition.

Deanne and I were born eleven months apart. Due to my failing the fifth grade, we were in the same class. My father hired a tutor for me to improve my grades and attitude. It was at that point I realized there wasn’t anything I could do to change my dad’s mind about the schools I would attend. From then on, I worked hard to get good grades. My sister helped me after Dad terminated the tutor. Over the next few years, Deanne and I studied together.

Once the speeches ended, the headmaster stood at the microphone. He started reading the names from his list. One by one, we went to the stage to receive our diplomas. After the last student received his diploma, we all tossed our caps in the air while cheering and clapping.

Deanna and I found our caps after the foray and put them on. She smiled at me and said, “Well, four more years.”

“I hope college is better than high school was,” I said. Placing my hand on my sister’s back, I guided her toward the exit.

Outside, we greeted our parents. They congratulated Deanne and me on our graduation. Our Aunt Juliet and Uncle Bert, along with our cousins, Larry and Sandy were there too. They also offered their congratulations. Like Dee and I, Larry and Sandy went to Hartford. Sandy graduated the year before, Larry two years ago.

We went to one of my parent’s favorite restaurants for an early dinner. Sitting in a private room, we discussed Dee’s and my years at Hartford as well as our future. My father insisted we spend the next four years at a private business school.

My father and Aunt Sandy inherited a successful business from their parents. The company had been in the family for many years. When we finished college, Dee and I would become the fifth generation to work for, and eventually take over the business, along with our cousins.

After finishing our meal, Dee and I sat with Larry and Sandy. Our parents were enjoying an after-dinner drink with their coffee.

“So, how do you guys like Carrington?” Dee said.

Carrington Institute, like Hartford, was a private school. The business school’s alumni included some of the most successful businessmen and women in the country. The program focused on their accelerated business program.

“I like the school. It’s hard work, but by going year-round, we can get our MBA in four years,” Sandy said.

“How about the social life? Is there any?” I said.

“Yes, there are a lot of things to do when you’re not attending classes of studying. There are parties most weekends. Most of the people there are cool. Like Hartford, there are spoiled brats, but not as many,” Larry said.

“Some of my friends are paying their own way or get scholarships,” Sandy said.

Dee and Sandy excused themselves and headed for the restroom. I sat across from Larry and said, “So, how are the girls at Carrington?”

“Like anywhere else, there are hot chicks and dogs,” Larry replied with a chuckle. “Going to a school where there are a couple of thousand students is different from Hartford.”

“I’m looking forward to it. How has it been living with Sandy? Dad said he bought a condo for Dee and me in the same complex. We’ll get to see you guys more often,” I said. “Maybe we should see if Dee and Sandy want to share one of the condos and we can have the other one. I plan to find a few girls to party with.”

Larry nodded. “Living with my sister is the same as it was when we lived at home, except we don’t have our parents there. We have an arrangement, so there are no problems when one of us brings someone home.”

Dee and Sandy came back into the room. They were laughing and bumping into each other as they walked toward the table.

“What’s so funny?” Larry said when our sisters sat down.

“Nothing really. I was just filling Dee in on the boys at Carrington,” Sandy said.

I looked at my sister, returning her smile. For the next hour, Larry and Sandy told Dee and me about life in the small town where Carrington Institute was. They said there were nice parks as well as several great places to visit. Sandy mentioned the beaches were less than an hour from the condo complex.

Carrington Institute was about six hundred fifty miles south of our Texas town. It was close enough that we could get home for a long weekend if we wanted to. I looked forward to the warm weather in Houston. Amarillo wasn’t bad, but it got cold during the winter months.

Our great-grandfather started his business in the Amarillo area, serving the oil industry. It provided the derricks and other things drilling for oil required. In the past years, the company expanded, providing equipment for offshore drilling and exploration. Dad told my sister and me he planned to open a facility closer to the Gulf of Mexico to serve the offshore industry.

We left the restaurant. Before getting into our cars, we chatted about Dee’s and my graduation party in two weeks. Mom wanted to rent a hall, but Dee and I convinced her we would prefer to have the party at our ranch. Our parents agreed provided we had the event catered.

Dee and I sat in the back seat of the Suburban as Dad drove home. People referred to the vehicle to as a Texas Cadilac. Dad’s was loaded with all the options available. In addition to the Suburban, we owned two pickup trucks and a full-sized Lincoln.

Dad turned onto our road. A couple of miles later, he drove through the iron archway leading to our ranch. On the top of the arch was The Barrow Ranch in iron letters.

The thirty-five hundred-acre ranch had been in the family for several generations. While small by Texas standards, it was more than enough for our family. Our house sat near the center of the property with a three-quarter of a mile driveway from the main entrance.

We owned ATVs to ride around on the five and a half square mile property. There was a large pond as well as many trees on the ranch. My sister and I liked to swim and fish in the pond. We have a built-in swimming pool, but we also enjoyed the pond.

As we neared the house, I noticed a vehicle parked near the garage. When we were close, I saw it was a new Suburban.

“Who’s truck is that?” I said.

Dad parked next to the Suburban and opened his door. When Dee and I got out, he handed each of us a set of keys.

“We bought this for you to have at school. You’ll need to have something to get around in,” Dad said. “Your mom and I decided you two could share one vehicle because you have the same schedule.”

“What if we want to go somewhere different?” Dee said.

“I’m sure you two will figure it out,” Mom said.

I went to my bedroom to change. After taking care of my slacks and shirt, I put on a pair of shorts and a tee shirt. Leaving my room, I went downstairs to the family room. While I searched for something to watch on television, Dee came into the room.

My sister flopped down on the other end of the couch. She propped her feet on a footstool and said, “What are we watching?”

“It doesn’t matter to me. There isn’t anything good on,” I said. I tossed Dee the remote. “See if you can find something.”

Dee flipped through the channels, settling on a movie. She dropped the remote on the cushion, leaning back to watch the show.

“It was cool of Mom and Dad to get us the truck for school, wasn’t it, Greg?” Dee said.

“I think so. It will be great for us,” I said. “Do you think we’ll have a problem because we only have one vehicle?”

“I don’t think so. We have classed at the same time so we can ride together. If you have a date, you can use the truck. If I have one, I hope the boy had his own car.”

“Are you hoping to find a boyfriend?” I asked Dee.

Shrugging her shoulders, Dee said, “I kind of hope so. It was a pain dating the boys from Carrington. It was like everyone knew everyone’s business. A girl had to be careful, or she’d get a bad reputation.”

“It’s different for boys. We don’t care,” I said.

“No, boys try to get a reputation as a stud.”

“Well, that was never a problem for me. As you said, the nice girls wouldn’t do too much,” I said.

“There were girls you could have taken out. You know, girls who didn’t care what other people said about them,” Dee said.

“Sorry, that’s not my style. I know guys who went out with Suzie Knapp or Laura Jones. Most of them bragged about how far they got with them. Me, I would never talk about a girl I dated,” I said.

Dee chuckled. “I know. You never shared any of the details of your dates with Kim.”

“Nope, I sure didn’t.”

“Well?” Dee said.

Laughing, I said, “My lips are sealed.”

Dee threw a pillow at me. “You’re a brat. I’d tell you.”

“Dee, I really don’t want to know what you and your dates did when you went out.”

Dee mumbled something I couldn’t hear. I sat back to watch the movie, thinking about the strange conversation my sister and I had.

Even if I would tell Dee what I did when I dated Kim, there wasn’t much to say. We would make out, but it was limited to kissing. The only time I tried to feel her breasts, she told me never to try it again. We continued to date until after the senior prom. Kim said she was leaving right after graduation and felt it was better for us to break up.

About one hundred of our friends and family attended our graduation party. The caterer prepared steaks, chicken, ribs, and all the fixings for our meal. Dad hired a bartender to serve our guests.

Dee and I talked with our guests, thanking them for coming and for the gifts they brought. We walked around the patio, stopping to chat. I led Dee to the bar and asked the bartender for two beers. He glanced at me, and then at my dad. Dad nodded, so he gave my sister and me each a bottle.

“Damn this tastes good,” Dee said after taking a drink.

“I didn’t know you liked beer. I’ve only seen you drink mixed drinks,” I said.

“I do like beer. The other drinks are too sweet anymore,” Dee said.

Our parents allowed us to have a drink on occasion. We had to make sure we didn’t over do it, or drive after having booze. Summer in Texas can be hot and dry. A cold beer tastes great when you’re parched.

Larry and I sat near the pool, each of us enjoying the cold beers we held. I watched my sister and Sandy walking around among our guests. They went to the bar and got beers. Looking toward me, Dee held up her bottle. I nodded, smiling when she asked the bartender for two more.

“Here you go,” Dee said as she handed me a bottle of beer. Sandy gave one to Larry.

“Thanks, Dee. Don’t get loaded,” I said.

Shaking her head, Dee said, “I’m being a good girl. I don’t want Mom and Dad pissed at me.” Dee smiled. “You better be careful too.”

“I am. This is my third beer.” I held up the bottle Dee gave me.

The afternoon went great. At about five, our guests began leaving. Dee and I chatted with Larry and Sandy before they left. They said they were heading to school for the summer session.

“We’ll see you in August when you two get to Houston.” Sandy chuckled as she looked at Dee. “Don’t do anything I wouldn’t do.”

“Greg and I will see you as soon as we get there,” Dee said.

Sandy gave Dee and me a hug. Larry and I shook hands, then he hugged Dee. Standing next to each other, my sister and I watched our aunt pull away from the house.

Dee and I returned to the backyard. By six o’clock, everyone had left. The caters cleaned up, loaded their trailer, and left. We went over to where our parents sat near the pool.

“Thank you for the wonderful party, Mom and Dad. I had a great time,” Dee said.

“So did I. As Dee said, thanks. It was nice seeing everyone,” I said.

“I’ve been in the heat too long. I’m going into the house where it’s cool,” Mom said.

“I’m going with you, Laura. Are you two coming?” Dad said.

“We’ll be in shortly, Dad,” Dee said.

Mom laughed and said, “Don’t get drunk.”

I laughed, then assured our parents we’d behave.

“Do you want another cold one?” Dee said as she got up and walked to the bar.

“Sure,” I replied, smiling as I watched Dee walk around the pool.

When my sister reached the far end of the pool, the setting sun backlit her. I could almost see through the thin cotton sundress she wore. Diverting my gaze, I waited for Dee to bring our beers.

Dee and I sat outside for a few hours. We talked about the party and our upcoming trip to Houston. While we talked, we had another cold beer.

“You’re going to get loaded,” I said.

Dee smiled and shook her head. “I’m doing fine, Greg. I won’t get drunk. You better behave too.” My sister laughed. “Just a little buzzed.”

We finished our beers and went into the house. Mom and Dad had retired to their room. Their bedroom was huge with furniture, and a television, as well as their king size bed.

Dee and I settled on the couch in the family room. I sat on one end of the sofa while she sat on the other. My sister turned on the television, switched to one of the music channels, and put the remote on the coffee table. We sat listening to the soft jazz while relaxing.

Dee began chuckling, then giggled like a schoolgirl. When I asked her what she found funny, Dee moved next to me.

“Do you remember when we learned to kiss?” Dee said.

I laughed as I nodded my head. It was about four years ago. Dee had just turned fifteen. I was going to be sixteen. Because we were born eleven months apart, there was just over a month when we were the same age.

Our parents wouldn’t allow Dee to date until she was fifteen. Even then, she could only go to chaperoned parties or the movies with a group. One evening, Dee asked me if I’d ever kissed a girl. I told her no. My sister said she never kissed a boy and was worried that she wouldn’t do it right if she got the chance.

That evening, my sister and I learned to kiss. Our first attempts were clumsy, but before we finished, we were doing better. Over the next couple of weeks, Dee and I would hone our kissing skills. We never French kissed or touched each other.

“Yes, I remember. It was kind of lame, wasn’t it?” I said.

“I didn’t think it was lame, Greg.” Dee took a deep breath. “I still don’t. For me, it was perfect,”

“Yeah, it was good for me too. I didn’t feel like a clutz when I started dating.”

“Right? I felt comfortable when I kissed a boy for the first time, a boy other than you,” Dee said. “Have you ever done more than kiss a girl?”

I shook my head.

“I never did anything else either.”

Dee sat staring at the television for a moment. She fiddled with her shoulder-length auburn hair, wrapping it around her fingers, then releasing it.

“What brought that on?” I said.

Shrugging her shoulders, Dee said, “Did you ever think about it after we kissed?” Her voice was almost a whisper.

I thought about my answer. The truth was, I thought about my first kiss for a long time after it happened. Many nights I would relive the kisses while pleasuring myself. Even after I started dating Kim, when I masturbated, Dee would fill my thoughts. Smiling at Dee, I nodded.

Dee’s face softened. She looked at me and said, “Me too.” Dee took a deep breath. “I thought about it a lot.”

While we’d had a few beers, I wasn’t drunk. I didn’t feel Dee was drunk either. However, I wasn’t sober either.

“You didn’t answer my question, Dee,” I said.

Shrugging her shoulders, Dee started fiddling with her hair again. It was a nervous habit she’d done for years. Whenever something was bothering Dee, she would play with her hair.

“Do you want another beer? I’m going to have one,” Dee said.

I thought about refusing but decided to join Dee outside. We went out to the patio, grabbed a couple of long-necks, and sat on the glider. Dee took a drink from her bottle and squirmed on the seat.

“I know you said you don’t kiss and tell, but will you tell me what you and Kim did together?” Dee said.

I chuckled and said, “The same thing you and I did with tongue. Other than kissing, we didn’t do anything else. How about you?”

“Same,” Dee said.

After taking another drink from her beer, Dee looked into my eyes. She held our gaze for a few moments. Smiling, Dee said, “Did you want to do more with me after we kissed?”

“To be honest, yes.”

Dee giggling told me she was buzzed. I didn’t know what was going on, but I was curious about where my sister was headed.

“I wanted to do more too, Greg. If you had tried to feel my breasts, I would have let you.”

Now I was intrigued. My sister admitted she would have let me feel her up if I had tried. I chuckled to myself, remembering something my dad always said. He told me hindsight was twenty-twenty.

“You know that we’re going to live in Houston and be away from everyone we know, don’t you?” Dee said. I nodded. “I want to find a boyfriend. I want a boy I can date and do things with.”

“I hope to meet a girl when we’re at school.”

“As good looking as you are, you won’t have a problem finding a girl,” Dee said with a grin.

“Neither will you. I mean finding a boy.”

Dee was a cute girl with a nice body. She kept her auburn hair shoulder-length. Her blue eyes sparkled, and her smile was killer. My sister was about five eight, three inches shorter than me.

“Thanks for saying that.” Dee ran the backs of fingertips on my cheek as she grinned.

“I’m just stating the truth, Dee. You’re a cute girl,” I said. While I wanted to tell my sister she was sexy I didn’t think it was a good idea.

Dee shifted on the seat, pulling one of her legs under her other one. I glanced at her legs, noticing her skirt rose, exposing her thighs.

“Greg, this is going to sound weird, but please listen to me.” I nodded. “Do you remember why we wanted to kiss each other?”

“Yeah, we wanted to know what it was like to kiss. We also wanted to make sure we knew what we were doing when we dated,” I said.

“Did you feel it helped?” Dee asked. I smiled and nodded. “Me too. The first time I kissed another boy I felt confident with what I was doing. I knew what to expect. I wasn’t scared I’d do something wrong. The last thing I wanted was for a boy to tell someone I was a bad kisser.”

“So I guess it worked for us. I didn’t want to have girls think I was a bad kisser either.” I laughed. “Kim said I was good at it.”

Dee smiled, took a drink from her bottle, and then blurted out, “Do you want to have sex with a girl?”

I gasped and started to stutter. Dee chuckled and said, “I want to have sex with a boy.”

“I think most people want to have sex with someone other than themselves,” I said after I regained my composure. I smiled, watching my sister nod her head. “Wait a minute; you’re not suggesting...”

“Why not?” Dee said. Her voice took on a serious tone.

“For one thing, we’re brother and sister.”

“That didn’t seem to bother you when we kissed,” Dee said softly.

I thought about her statement, smiled and said, “No, it didn’t bother me when we learned to kiss. It was great.”

“I know, right? As far as us being brother and sister, well, I don’t care. I love you. I don’t think you’d hurt me. I know that if we do anything, it would be incest. I also know incest is against the law and we could get into trouble if anyone found out.”

Dee leaned closer, put her hand behind my head, and pressed her mouth to mine. A moment later, I felt her tongue against my lips. I relaxed, opened my mouth, and accepted my sister’s tongue.

Wrapping my arms around Dee, I hugged her to me. Our kiss continued, our tongues darting in and out of one another’s mouths. We maintained the kiss for several moments before moving our heads apart. We stared into one another’s eyes, smiles forming on our faces.

“Dee, that was the best kiss I’ve ever had,” I said.

Nodding, Dee said, “No shit!”

Before I could respond, Dee started kissing me again. She squirmed around, sitting on my lap while maintaining her lip-lock on me. I held my sister as close as I could as any thoughts of incest fled my mind.

Dee and I made out like lovers, not siblings. As our kisses heated, I ran my hand up and down her spine. My sister wiggled on my legs, pressing her breasts against my chest. When we first kissed each other, Dee and I avoided any close contact. Now, we couldn’t get close enough.

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