My Sister Ch. 1

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His first time with his sister.
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Part 1 of the 2 part series

Updated 10/30/2022
Created 09/22/2001
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This is a fictional story a work of fantasy.

I have a relatively small family, there's my mother, father, and two sisters, Karen is two years younger than me at 18 and Molly is twenty-three. My father works hard to support the family so he is out of town a few days a month, he works in marketing at some company downtown. My mother is a franchise distributor for a major food corporation. My older sister was always the rebellious one she has her and eyebrow pierced, her hair dyed different colors all the time and has boyfriends that scare the family. Not surprisingly she left home early to move to Los Angeles and I haven't seen her since, that was 5 years ago.

My younger sister is I guess the nerdy type. She would be cute but she doesn't really take care of herself. She is around 5'1 will shoulder length brown hair. She is relatively skinny, but she always wears clothes that really don't show off her body, I guess you could call her frumpy. I'm relatively short at 5'5 but I lift weights religiously so I weigh a hefty 195, but it is mostly bulk, I'm not a big guy due to my shortness, but the muscle is there. I am not very successful with girls even though they tell me I'm cute, but I become too good of friends with them first, or I'm too shy to approach them, I've had maybe two serious relationships and sexual experience with 4 or 5 girls.

Karen was in her senior year of high school the day my story starts. She had been acting really funny around the house, kind of mopey and depressed completely uncharacteristic for her. My mother and father were constantly trying to figure out what was going on with her, they just assumed, because she is the academic type, that she had anxiety about finishing school and was nervous about SATs and all the other stuff graduating seniors had to worry about. I really didn't notice since I was away at college, but I did notice that she wasn't being herself when I came home for Easter break.

I tried talking to her to find out what was wrong, but she had a wall up. I asked her if I could take her out for the evening to a movie or something so she could feel better, and at some reluctance she agreed to go along. We went out to a movie and ate some dinner then headed home, she seemed to feel a little bit better, but she wasn't opening up what was going on with her life, why she was so depressed. We went back home and since it was late our parents were in bed. I asked her if she wanted to hang out for a little while and she agreed since it was holiday. I went into the kitchen and grabbed two beers and we started drinking them (our parents are ok with us drinking at home, they rather at home then drinking and driving).

I tried quizzing her again, doing the thing where if I guessed it she had to tell me what was up. So I guessed unsuccessfully at first but when I guessed boys she grew very quiet, I knew I hit the nail on the head. I asked her what the boy troubles were and after another beer she decided to tell me. Her prom was a couple weeks prior and the boy she went with was a really big asshole. After the dance he took her out driving and they parked and started making out, nothing abnormal for after prom, and my sister never had a problem with kissing. But things started heating up and he kept groping her breast and sliding his hand down between her legs trying to play with her a little bit.

She told him to stop but he just kept persisting, so she slapped him and got out of the car and walked home. Since then all the boys at school were making fun of her, and called her prude and were being really ugly to her for not putting out on their prom night. I told my sister that she did the right thing, it is never ok to have sex with someone if you aren't ready. At this point we had drunk another beer and she started crying and crying, I really felt for my sister, I felt bad that guys were such assholes, no one deserved to be treated like that. So I moved over next to her on the couch and put my arm around her and she started crying into my shoulder, she cried for a little over 10 minutes and I told her everything was ok.

She then said that I was the best big brother she had ever had, and I said that I was her only big brother and she smiled and kissed me on the cheek and we hugged, and things were happy with her once again, she felt better once she got the crying out. She then started asking about boys, why they were assholes, and the usual girl feelings of what's wrong with her, I said nothing, but the she just said I said that because I'm her brother. I told her not at all that I thought she was very good looking and too bad that she was my sister.

She smiled and this time she kissed me on the cheek, but it kind of lingered she pulled back and I looked into her eyes and we kissed on the lips. It was a soft kiss, nothing too wet. I kissed her again and again, she opened her mouth and allowed me to slide my tongue across her teeth and into her mouth and we started kissing more and more deeply. My hands went to her back and rubbed up and down, and she just rested her hands on my thighs, the kiss got deeper and deeper and we were making out deeply now. Then my hands slid down her back closer to her rear and she slid her hands all over my chest.

We pulled away simultaneously and agreed that it was wrong to be doing that. I got up and took a shower and polished one out very quickly to try and relieve the images of my sister. I went to bed and around 330 in the morning I felt someone crawling into bed with me, it was Karen.

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