Where it happened: Home
Langauge: english
Sex: Male
Rating: 9
Category: Straight
My Sister and I
I want to start off by saying I will be starting off at the very beginning when we started messing around with each other. It did start when she was 11 and I was 13 so if you do not wish to read about some activities please move on. To keep dignity and privacy I have chosen to change our names. My sister Rebecca and myself Andrew had quite the wild ride.
This all started the year after we moved out of the country and into the suburbs. Not too long ago only 6 years or so. We were used to knowing our neighbors well and in the suburbs there was not as much communication between neighbors so we didn’t really get to know the neighbor kids. Soon enough we found our own fun though. Our rooms were upstairs away from our parents. I had my own room and Rebecca shared a room with another of my sisters. My room is large and spacious for one person to be living in my sisters got the homes “Master Bedroom”. It has 3 closets one of which was a walk-in that had a light inside. One day while it was raining and we were both bored she asked if I wanted to play truth or dare. I accepted and she added that it would be in private by playing in the walk-in closet. I was all for being alone and in the dark with my sister as we could probably find some fun dares to do. No one else was home when we started this first time but it was a pretty harmless game. It started with her daring me to do things such as lick the wall or her foot and me daring her to lick my foot or suck on my toe. Suddenly she surprised me it was my turn and she asked “Truth or dare”
“Dare” I said.
Rebecca said “I dare you to show me him” as she pointed at my crotch.
“What do you mean show you him?”
“I want you to show me him you know your thingy I’ve never seen one.”
“Alright fine.”
I was laying down at the time so I had to raise my hips to lower my pants. It was almost futile trying to keep from becoming erect after she asked if she could see him. I lowered my pants and my cock sprang to life. Rebecca looked on in awe at the first penis she had ever seen before. She even asked
“Andrew can I touch him?”
“Sure Rebecca if I can see them” I said pointing at her chest.
“Of course Andrew but I get to go first” she said as she put her hand on him
She began playing with him moving him all around and stroking him up and down a few times. She even grabbed ahold of the jewels a few times. One time she even squeezed them a bit to hard and I had to ask her to be more gentle. After about 5 minutes she was tired of playing with him and I asked if it was my turn to see them. Rebecca reluctantly pulled her shirt up. Into view popped two beautiful formations that were just budding into and solid and firm A cup. I asked
“Rebecca can I feel them I’ve never seen any before.”
“Sure Andrew but only if we can play this again another time.” She said
“Alright Rebecca sounds good to me.”
Soon I was rubbing and squeezing and enjoying myself to no end. But for a start there must be a finish. I got about 5 minutes of play in before we heard someone enter the house. Rebecca pulled her shirt down and we both rushed out of the closet to our respective rooms. Later that same night I got a note under my door saying that if I wanted to play again next time mom and dad where gone to slip a note under her door. So I did and she agreed to meet me in the closet as soon as mom and dad were both gone from the house.
A week went by and our parents took our other sisters to doctors appointments. We were left home alone again. I went into the closet and found her already sitting there. As soon as we started the dares weren’t normal.
“Andrew I dare you to let me play with him.” Rebecca said
“Rebecca I dare you to touch him with them” I said.
She pulled her shirt off and started rubbing her wonderful tits all over my cock wrapped what she could around the shaft and even stroked up and down a little bit. Soon she stopped and had asked me if we both agreed should we just play dare or dare since there were no more truths being asked. I said sure and soon enough we no longer had any truths. We just dared each other. I was up and said
“Rebecca I dare you to let me play with her” pointing at her crotch.
“But Andrew she isn’t any fun I havnt found anything to play with using her.”
“Just let me see please I’ve never seen one before.”
“Alright Andrew fine.”
She go up and pulled her pants down and sat back down with her legs spread around me. I inspected her hole and saw how wet it was and asked Rebecca if that was normal. She said oh yes it normally gets wet when I’m excited. I inspected and rubbed a bit down there for about 2 minutes before we heard someone come in the house again and we got dressed and rushed to our separate rooms.
That night about 10PM a note was slid under my door by my sister asking if I wanted to play later that night once mom and dad had gone to bed. I wrote back yes but what if our sister woke up and checked the closet since they share a room. I asked if it would be better to play in my room since it had a lock on the door. She replied back and said that would be fine and that she would come join me as soon as our parents were asleep.
About 2AM my sister came into my room. Because of faint light it looked like she had a dress on when she came to my bed she told me it was one of our fathers old shirts that was just entirely too long on her. She then informed me that to make our games easier she wore that shirt specifically so she didn’t have to wear panties or her training bra when she came over. I was overjoyed at the fact that our games would be even easier. That night the games took a slight change. It became what do you want to play with. We called the game mommy and daddy since our parents slept in the same bed we thought they played with each others bodies all the time. So we would choose who would go first and I would ask to play with them she pulled the shirt all the way up and would let me play with her tits. She would ask to play with him I pulled down my pants and she would do anything from stroking to rubbing or tits on him. I then asked
“Rebecca can I play with her.”
“Sure Andrew” She said as she pulled the shirt up. “But how will you play with her?”
“Well I was thinking could I maybe touch her with him? And maybe just rub them together a little bit?”
“Well I guess so just make sure he doesn’t go like inside her or anything I don’t think that would be a good idea.”
“No problem Rebecca I’ll be sure to be careful.” I said as I pulled my pants and boxers down.
I got close to my sister and spread her legs I brought him very close to her and just made them touch Rebecca jumped a little bit to the first touch. She settled down and then I started to rub him up and down her. It was the best feeling I had gotten from Rebecca up to that point. After a couple minutes of this I realized I was a little to close and some of his head was popping into her I stopped and moved on with the game from there as to not cause any alarm to Rebecca. She then said she was tired and that we would play another night some more.
As time went by and things progressed we got a little more daring. Fast forward a year Rebecca had just turned 12 and had nicely formed A cups and I had just turned 14 with a nice 6 inch cock. We still got together on weekend nights to play our games but it wasn’t enough for me anymore. The next time we played I had to try something else. Rebecca came into my room at 2 AM after my parents had for sure gone to bed. We played most of our normal games. Rebecca touched him with her. I rubbed her with him and even rubbed him on them a few times. I finally got my turn again and asked Rebecca if I could play with her again. She pulled the shirt off and finally I got between her legs and asked
“Rebecca can I try something new?”
“What is it you wanna try Andrew?” she said
“Could I stick him in her tonight? I want to try it.” I asked
“Just a little bit I guess. Go slowly so you don’t put to much in” she said.
I was awe struck that she said yes. But being overjoyed didn’t stop me from continuing. I touched her with him where I thought the hole was. I was wrong and Rebecca stopped me because I was actually to low and about to put it in her butt. She pulled him up to her and told me to push. I put some pressure down and without any effort the head of my penis was inside of her. I continued to push going a little bit deeper until I hit some resistance. Finally Rebecca told me to stop. She then asked
“Well what do we do now?”
I replied, “Well its your turn but could we just sit with him in her for a little bit it just feels so good.”
“Alright Andrew but don’t move around it hurts a little bit with him in her.”
Staying as still as I could I just took in the sensation of the warmth and wetness surrounding my cock. It was overwhelming. Soon though the pressure hurt Rebecca to much and she asked me to pull him out. I slowly pulled out to get every last minute of the sensation. With and audible *pop* the head of my penis came out of my sister. After this Rebecca went to bed even though I still had a raging hard on. I went to the bathroom and relieved myself until finally going to bed.
A week or so down the road summer had started. We could now stay up as late as we wanted on any day of the week. Sometimes we would stay up and play our games 4 days a week. With each time we played I would ask if I could put him in her a little bit further. With every week that past by Rebecca would let me put him in a little bit more. When we would hit resistance going in further she would tell me to do little pushes with my penis which in reality was contracting my penis making it swell a little bit more. Almost like what happens during ejaculation. Finally the night came when Rebecca would let me to stick him in her all the way to the hilt. She came into my room late that night and knowing that the only game I wanted to play was him in her she instantly took the shirt off and laid on the edge of the bed with her legs spread.
“Andrew if I’m going to let you put him all the way inside her you have to promise me you will follow my directions the whole time. And be sure not to let him squirt anything inside her I want to make sure your not oozing any juices before we start.”
“I know Rebecca I know I have the towel ready for the juices and when haven’t I listened to you while we play.”
(to clarify the juices where my precum she had finally noticed it on them when she would rub him after we had been playing for a while into the night.)
She took the head of my cock and pulled me up to her opening and said
“Push a little bit Andrew.”
I dropped my weight slightly onto her to get him inside of her the first bit. The head of my cock slipped right inside of her and slowly I worked in some more. I hit some resistance and Rebecca stops me and said
“Alright Andrew now do some of the little pushes.”
“Alright let me know when” I said
I began to contract my penis inside of her several times slowly to be sure she can feel it inside her. Looking at Rebecca’s facial expression I was certain she was feeling my contractions. Finally she said
“Alright now a big push”
I began to lower more of my body weight onto her. Slowly but surely I felt him slip more and more inside of her. A little bit more than half of him was inside of her and Rebecca stopped me again and said
“Stop and do some more little pushes.”
I began to contract him rapidly after about 20 contractions she stopped me again.
“Andrew can you do the little pushes but make them a little longer?”
“Sure Rebecca” I slow down the contractions to only 10 in a minute “Is that better?”
“Yes continue doing that and do a big push too.”
I put more of my weight into the push and felt more pleasure surround him as he went into her almost ¾ of the way. I was very upset when Rebecca stopped me yet again
“Andrew just do some little pushes now I think we are almost there. “
I reluctantly did some more little pushes contracting him for another 2 minutes until she told me to do another big push. I put all my weight into her and pushed him until I couldn’t push him anymore. She finally said
“I think he is in all the way let me check.”
She then reached down between us and felt to see how much of him was still outside of her. Less than 1 inch was still exposed and she concluded he was all the way inside of her.
“So now what Andrew?” she asked
“Well Rebecca could we just sit here for a little bit with him in her?” I responded
“I guess just make sure nothing squirts out of him while he is in her. I don’t want any mess to clean up.”
“Alright Rebecca well can we sit here and could I have him do some little pushes while he is inside her?”
“Sure Andrew.” She said
I began to contract my penis several times rapidly at first and slowly later to feel all that I could. I even tried pulling him out just a hair and putting him back in. Rebecca didn’t realize I had full control of him when he was inside of her as to why she said to make sure he didn’t squirt anything while he was inside. She had seen him cum before so knew what would squirt out and didn’t want it inside of her. After I was done doing little pushes I just sat there feeling all the pleasure being inside of my sister. All of a sudden I felt him contracting inside of her to this day I still don’t know if that was the first time I came inside of my sister or not but she still doesn’t realize I may have as she thought I was in control of the little pushes as we called them.
This is just the first part of the stories I had with my sister Rebecca I will continue to post more at a later date please leave comments about the story layout or my writing style so I can make improvements this is the first story about our experiences that I’ve written. All comments welcome thank you.
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