My Sister Kelsey Pt. 01

This is a story series about my ongoing relationship with my sister Kelsey.

My sister and I have always been close. She is just under a year and a half older than me. So being close in age we have shared a lot of experiences, friends and are friends ourselves. We are very chill with each other, never have fought much like many siblings do. Both of us are more on the "bland" side, and both very laid back personalities, which I think is why we get along so well" She succeeds in many things and I respect and look up to her a lot.

We live in the Miami Florida area, and have our whole lives. We live in a pretty nice area and I would say our family has always been pretty well off.

My sister started attending the nearby university, but decided to stay home as she is a very practical person to save on expenses. She is majoring in Art as it is her passion, but again a super practical person so also is majoring in accounting.

She was never big on party's or going out all the time so it didn't surprise me she stayed nearby and home for school. My parents were glad to have her staying, and we got along well so her company was nice to have. Being only a grade ahead of me, it is nice having her around because she did really good and school and will help me out with school when I need it.

Kelsey is a very cute girl, although I could see how she would easily just blend in. She is White, dirty blonde hair, 5'4, small build, but not athletic. Growing up I never was one to think 'Oh I have a hot sister' but I did notice she was cute for sure. I never had sexual thoughts about her either, but at the same time as a teenage boy growing up I did "notice" her if we were at the pool or she was in a towel around the house. But again, at the time it was my sister so nothing more than that.

So our very first experience at all that was sexual took place midway into her 1st semester into college, and I had just recently turned 18 and she had been 19 for a few months.

There was a day I was off of school for a "school service day" so I was home alone for the day. I up until this point was a virgin. I had dated a couple of girls in school, some were casual, one I knew she would have done it with me, but honestly I just didn't have the desire to lose my virginity to her as I knew we wouldn't date much longer. (I know it sounds old fashioned but I was just waiting for someone I thought that was worth it.)

On this off day, I was watching porn as I didn't have many days that I was home by myself and I was an 18 year old guy. I remember specifically at the time I really was into African American women. I had a crush on a black girl in school but never worked up the nerves to ask her out. But I at the time was watching black girls doing it with white guys as I was really attracted to black girls.

So I am on my bed jerking off enjoying myself, and suddenly Kelsey has walked in the door. (I did have it cracked open so I could hear if someone were to come home, but never heard her at all.) As she walked in she was like "omg sorry" and walked out.

I quickly got up to go talk to her. I told her I didn't think anyone would be home. She told me she had a teacher not show up to school and that's why she was home mid day and that she thought I was watching TV so that is why she walked in.

She told me that she felt extremely terrible for walking in on me. I could tell that she felt really bad, because she said it like 20 times right away, and I usually know that is how she was sincere about anything. I told her to please not worry and just keep it between us. She told me that of course she would.

So just a few minutes later she comes back into my room and proceeds to tell me some stuff. She told me that she didn't want me to be embarrassed at all and that it was killing her that she did that to me. But she told me that she also watches porn and masturbates regularly, and she was telling me this because she didn't want me to feel bad at all. I could tell she was feeling really guilty since she told me that.

I told her that it was fine and not to worry. I told her I was embarrassed but would be fine if we just kept it to ourselves. She thanked me for not being mad.

So then she asked me the question that at the time made me stop everything I was doing or thinking about. She asked "What would you think about us getting naked in front of each other?"

I was so thrown off but just asked with a confused "Why?"

She said "Since I saw you naked it would only be fair, and honestly it would be kind of nice to see a real penis in person."

I was still thrown off but also confused because I knew she had a serious boyfriend and was certain they had done it. So I questioned what she said, "haven't you already seen one before? Your not a virgin."

She explained that even though she had done it, she only did it twice at her boyfriend's house and they had the lights off and never even touched it. She said he was in such a rush that it was not a great experience.

I still asked her why she would want to see me? She told me that she was more or less just curious, as embarrassing as it is at her age. She also said "we are both really mature boring people that won't let it affect either of us."

As someone who was extremely interested and curious in seeing a girl naked in person, I was really interested. And she was right that we both are very "technical" people and don't let much affect us.

Not to seem too eager I just said. "Well if you think it is a good idea" with a shrug. She laughed and said she thought we would both benefit. We discussed it a little and agreed to it.

She told me she would get in her room naked and wait for me to just walk in when I was ready.

After she left, I just couldn't believe I was about to see Kelsey naked. I just kind of smiled as I thought about it. I was getting myself "ready", I didn't want a full erection but definitely wanted to look "good" as I walked in.

As I walked down the hallway, I was trembling thinking about walking in there. I took a deep breathe and opened the door. And there Kelsey was standing in her room completely naked. I just looked at her and smiled.

I couldn't resist thinking how cute she looked. She gave the cutest smile back at me.

I remember thinking that she looked so real compared to the fake girls on porn. She had small but full breasts, and although she is skinny has a little belly and just that she was cute. And how then I realized that I am way more attracted to cute than "hot / sexy"

We both walked towards each other and just both said how weird it was. It seemed so fake that we were just standing there naked in her room.

After what seemed like forever. Kelsey asked if she could feel my penis. I was nervous as anything in my life but said "of course."

As she grabbed my penis it felt just so good. She had a soft touch as she was just simply trying to "feel around it" she asked me. Kelsey started to squeeze it and it felt so much better than anything in my life.

She asked me if I wanted to feel inside her. I was eager to feel. She moved my hands and I grazed her lips, and then she showed me where to stick my fingers in. She was wet and they went right in. She told me where to press and she instantly began contracting.

Kind of took a moment just thinking how crazy it was I was fingering my own sister!

She kept getting more wet and she eventually just lay all the way down on the bed and was taking it in.

After a couple of minutes, she asked if I had a good feel. I told her yes it was very helpful.

She then asked if she could keep jerking me to watch me cum or if that would be too far.

I told her it was fine. She then started giving me a hand job. I always figured they would be good, but it was even better then I imagined. We looked at each other and just smiled while she rubbed up and down.

I told her that I was about to cum in case she wanted to back away. Kelsey said "it's okay if you get it on me, I want to feel it anyways."

Almost right after she said that, I started to cum. I was actually embarrassed and proud at the same time. It went further than I ever had cum before. Got on her and her bed. I told her "OMG, I am so so sorry, I didn't mean to do that." She said "don't worry, this is what I wanted to see."

As we both laid there for a moment. Kelsey said "This isn't going to make things weird right?"

I said "No, I understand this was just for us to get experience, and can compartmentalize that."

She said "Okay good, I just want to make sure. That was nice but I didn't want to make things weird."

I got up and went to my room to clean up. Still just in disbelief. As I got in the shower I jerked off again thinking about the whole experience.

I will say that evening being around each other was really funny. I was nervous, but couldn't stop looking at Kelsey and I'm sure she knew. But we both acted normal obviously not to let anything on at all.

The next couple of days, I couldn't stop thinking about my naked sister. When I was jerking off, I didn't even need porn, I just closed my eyes and thought about what we did.

I could feel myself thinking about her more and more. I was constantly trying to snap myself out of it. I tried to remind myself that it was my sister. But nothing worked.

That weekend our family went together out to Miami Beach. And just that day being around her in her bikini was killing me.

I knew I was letting it get to me even though I told her I would be fine.

Fast forward about 2 weeks from when we did this and my sister has beaten my parents home one evening. And I was in the living room and Kelsey came and sat next to me, smiled and asked "Do you want to do that again?" ...

(This ends part 1. Part 2 to be released soon)