Everyone having sex is at least 18. This is fiction, I made it all up so don't expect a realistic story. You won't get one. Warning: this is a self-edited story. I use Grammarly to help reduce my murder of the English language. Special thanks to goducks1 for his help.
This is a "HALLOWEEN CONTEST 2018" story.
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Chapter 1 -- I Turn Eighteen
My family was always sort of odd, weird, and not like other families. Many would say my parents are eccentric. Isn't that what they say about all brilliant people? They seem to know everything. I am their youngest child. I have two older sisters, Emma who is twenty and Wendy who is twenty-six. With Wendy being eight years older, she never had much use or interest in me. I don't blame her, she is done with college and owns a nursery where she grows flowers and herbs.
I work for Wendy when I need money. She always needs some heavy lifting done for the nursery. Soil, fertilizer, and stones are heavy and back-breaking work. She treats me well, I can't complain. A nice side benefit is that many women go shopping there.
I often see Emma at home. She goes to a local college and is off to State college next year. She is into medicine and working towards an alternative medicine degree. For thousands of years, people have been healing themselves without a doctor. She even has me believing in it ... almost.
My interest is engineering. Math and geometry come easily to me. My parents aren't rich, I will end up going to the local college for two years and then on to State like my sisters. Currently, I am in training for my last year of wrestling in high school. I have been state champion for the last two years and am favored to win again this year. I am active in the chess club and debate club. I love competition.
I am an average to maybe below average looking guy, medium build, short black straight hair. I am very strong for my size. I see guys much worse looking than me getting girls, yet no woman will even look at me. Almost eighteen-years-old, clear skin, muscles, popular, and involved with clubs where I meet women. Yet, I can't get a date. It's like my parents follow me around at school. Women look at me as if I am pathetic. I don't get it.
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It's Friday night and it's my birthday today. Nobody said anything at school. It was kind of depressing. I get home and mom made my favorite, chicken kabobs. Oh joy, yippee. Oh wait, I hate chicken kabobs. I want pasta or lasagna. I nice roast beef would be ok. Nope, chicken and vegetables, healthy food. Swell. I try to smile to make mom happy.
We did have a birthday cake. Sort of. Six cupcakes with a candle in each. My parents got me a video game and my sisters each got me gift cards. It didn't take long before I was ready for bed. At least I can listen to my own music. I bought a good headset a while ago, they are awesome. I love digital music on a good set of headphones with extra bass.
It didn't take long for me to close my eyes and start beating my meat. Below average applies to my cock as well. I open my eyes to see cum shooting up and on to my shirt. Then I get the shock of my life when my sister Wendy is standing in my doorway. She is staring at me. She has a slight smile on her face.
Even though Wendy is much older, she lives at home still. She has no need to get away from our parents. Life is good for her I guess. It would be much harder and expensive to live on her own. Now, she can afford a nice car and other luxuries in life that Emma and I can only dream of.
Wendy says to me in a sexy voice, "Having a good birthday I see." I can't say anything. I am at a complete loss of words. "I would take that shirt off. Then I can give you my real present. You are eighteen-years-old now."
Holy shit, what is she suggesting? Wendy has a mature body compared to the good-looking girls at school. She has long swirling light brown hair. It seems to always be a mess and tangled. She doesn't seem to care enough to keep it nice looking. Her face is round and cute looking. Her legs are long and thin. She has small B cup breasts. They're perky and look good on her. Her frame is thin, huge boobs would look out of place on her.
She starts stripping off her clothes, I am mesmerized.
Wendy giggles, "Take off your clothes silly." I am quick to disrobe. I take it all off. She stops at bra and panties.
She looks at me, taking all of me into consideration, then says, "Boxers could have stayed, but this works as well. Get in bed."
I jump into bed. She closes the door and turns off the lights. She gets in bed, slides back into my chest, and pulls my arm around her and through her breasts. That is an awesome feeling, boobies touching my arm. They're soft and bouncy. I don't move for fear of pressing my luck.
Wendy says to me, "Good night my love."
I lean forward and kiss her on the neck and shoulder, "Good night boss." She giggles.
We both fall asleep. I take much longer to sleep as my mind is very busy thinking about my sister. What the hell is going on here?
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The next morning, she is gone before I wake up. I did get a great night sleep though. I am last to breakfast. Mom and Wendy are fighting over who cooks. While they decide who makes the next set of eggs, mine, Emma cracks the eggs and starts them in the frying pan. Mom and Wendy stare daggers at her but Emma could care less. She has a cute smile on her face.
Emma is a lot like her older sister but more flamboyant, thinner, only A cup tits, but a charming personality that has made her a school favorite wherever she is. Men are driven to her, yet she rebuffs them like fleas. She has always been very nice to me. Almost overly nice like she is trying to please me all the time. She amuses me, and we get along great. She is off to do laundry and then shopping today.
After breakfast, I have a pool to clean and grass to cut. It's October now, this is probably the last cutting of the grass and next week I will be raking leaves. The pool is heated, it's been a warm fall, I still get to clean the pool. Tomorrow I have gutters to do. That will suck badly, they are gross. Oh, lucky me. On a positive side, Emma is out suntanning and topless.
What? Topless? I have never seen that before. I am staring, she knows I am staring, she lays her head back. I think my sisters have gone mad. I cut the grass and take nice long looks while I clean the pool.
As I walk close to my sister, she leans over, and in a seductive voice says, "Fucking pervert."
I was leaning in to hear her. I stand up and turn away. Now I feel the guilt. I was staring at my topless sister, one of my best friends. I feel small and insignificant. I want to curl up into a ball and hide. My confidence is shot, I feel terrible. How can I look at her again?
I quickly finish the pool and then run up to my room. I strip down and take a shower. I want the grass clipping and sweat off me. More importantly, I want to wash the slime off me. That thin layer of being a useless slug and perving on my topless sister. My sisters and I share a common washroom. Small house syndrome. When I finish, I dry off and open the door, so I can return to my room.
My sister is standing there, waiting for me. I only see her legs, I am looking down. I quickly close and lock the door. She shouts at me to open the door. I turn my back to the door and slide down to the floor. My hands are over my head and my head is between my knees. I feel sick. I will never look at my sister again the same way. I may never look at her again. I have tears in my eyes.