Let me start by saying this is a story about my s****r and I when we were both a lot younger. I have two s****rs, they are both older than me. One by five years and the other by eight. Neither of them were raised by my mother, she was very young when they were born. The oldest one, I'll call her Charlotte for name sake, (even though that's not her real name), was raised by my grandparents in the next state over from where my mom and I lived. We visited often, driving over for the weekend once a month or so and occasionally my mom left me to visit for a week or two while she went back home.... Continue»
Let me start by saying this is a story about my s****r and I when we were both a lot younger. I have two s****rs, they are both older than me. One by five years and the other by eight. Neither of them were raised by my mother, she was very young when they were born. The oldest one, I'll call her Charlotte for name sake, (even though that's not her real name), was raised by my grandparents in the next state over from where my mom and I lived. We visited often, driving over for the weekend once a month or so and occasionally my mom left me to visit for a week or two while she went back home.
I enjoyed going to visit because I always got special treatment while I was there, and since my s****r and I hardly ever got to see each other, it wasn't the typical sibling rivalry or arguing that k**s tend to do. We enjoyed being around each other and I looked up to her. My s****r would occasionally use me as her guinea pig for dressing up or putting make-up on, (she was planning on going to cosmetology school to be a beautician), and since she was so nice to me all the time I really didn’t mind.
I was very young when I discovered my penis and also discovered that I could pleasure it in many ways. I found that humping a pillow in bed was the easiest and most secretive way to experience an orgasm. More often than not, I would put myself to sl**p by humping my pillow and getting that nice tingly feeling down there. I wish I could remember how I figured that out but either way I did. Sometime when I was growing up I remember taking showers with my mother, for some reason I never thought much about the things I saw in there until a little later. One day I was in the bathroom and I found my mother's boyfriend's dirty mags next to the toilet. When I say dirty mags, I mean Playboy, not really dirty actually. I opened one up and saw things I had never seen and something clicked inside me. I felt compelled to look at the pictures and I found them very appealing, women wearing things they don't normally wear and posing in positions you do not normally see them in, at least not in public.
Also when I was growing up, I liked to draw pictures, pictures of anything I saw, cars, a****ls, buildings, and even people. I was halfway decent at it too. I won first place in a state art contest my mom entered me into a little later on. So, since I had seen those photos of those women in the magazines, I decided to reproduce my own versions of them. Something told me they were naughty pictures so I kept my own renditions of them hidden away. Over the period of about a week, I had gotten the image of the female form pretty obvious, breasts, nipples, hips, pubic triangle between the legs. I drew them here and there, whenever I was in the mood and alone.
So I'm on another visit to my s****r's and my mom drops me off for a week or so. Things at my grandparents/s****r's are as usual except that I'm honing my new found art work one day. I'm usually left undisturbed when I'm drawing, But one day my older s****r decides to pay me a visit and show some interest in my "art". She looks over my shoulder and quickly notices what the picture I am working on is, however she asks what I am drawing and I am a bit shy and embarrassed to say. She takes me by the hand, and starts leading me out of the room, all I can think is that I’m in trouble.
Let me say my grandparents are kinda old and keep to there own most of the time and my s****r always stayed out of trouble, so they had it pretty easy with her. She was very independent, smart, elegant and very beautiful, even when she was younger. So my s****r leads me to her room which seemed very far away, it was a large house, especially to a young boy. We arrive in her room and she shuts the door behind her and stands there for a moment and looks at me. I'm a bit confused and then she unzips her jeans and pulls down the front of her panties enough to expose her bush, it was staring me right in the face about two feet away, it was dark blonde almost brunette, and furry but not thick. It was a perfect little triangle, just like the other ones I had seen. I remember like it was yesterday, and then she lifts her t-shirt and bra to expose her b-cup sized breasts. I only know the size because they stayed the same size several years later when she decided to have them enhanced to a large c-cup. Either way they were a sight. She then asked me if that was what I was drawing, and I said yes. She asked where I had seen that before and I told her about the magazines. Then she asked me if I wanted to touch her, without saying anything, I reached out and gently touched her furry little bush, the hair was so soft and smooth. I petted it for a moment then ran my fingers through it and could feel her skin underneath. I was in amazement, looking up to see her looking down at me with this look of interest as she just stood there with her hands on her hips. I realized that I had forgotten about her breasts and before I could do anything else she said that was enough and zipped her pants back up. After that she led me out of her room and said this is our secret.
The next day I was wandering around the house looking to see what I could do. I went up to Charlotte's room to find her watching t.v. She was laying on her stomach at the foot of the bed (closest to the t.v.), with her hands propping her head up. I walked over and hopped on the bed and asked if I could watch with her, she said yes. I don't know how long it was before I asked her if I could see her naughty places again and without saying a word she slowly rolled on to her side without removing her eyes from the television and slid her shirt up to show her tits and then moved her hand down and unbuttoned the fly on her jeans, this time she was panty-less and when she pulled the flaps of her jeans open, there it was again, that beautiful patch of fur. She stayed on her side with one elbow on the bed, and her hand holding the side of her head up, the other arm lying long ways down her body with her hand resting on her hip. All the while she continued to watch the t.v. I was once again infatuated with these new places on the female body which I never get to see. I lied there for however long stroking, rubbing, and petting her pubic area and breasts, then it was time to stop.
Most k**s my age at the time know absolutely nothing of sex and I was no exception. I think I may have caught a glimpse of a man on top of a woman in an "R" rated movie or two that I snuck around and watched late at night. This is what I figured a man and woman were supposed to do. I already knew how to hump my pillow and I thought that was how it worked but I still didn't know about intercourse and actual penetration.
A couple days had gone by since Charlotte had shared her goods with me. Probably because she was busy doing school work or a part time job or something. I remember the next time something happened, it was something new. One night she decided to ask me if I knew what boys were supposed to do with girls and I told her yes, and as far as I knew, I did. So it was time to go to bed and i shared the bed with my s****r sometimes, she was wearing only panties and a long t-shirt and getting into her bed and motioned for me to get in. Once in her bed, she asked, "are you ready to show me what you know?" and so I complied. I quickly pulled my pajama pants and my underwear off while we were under the covers and she pulled hers panties off as well, this time I couldn't see anything, the room was very dim and the blankets on the bed covered our naked lower halves. I crawled on top of her, as I was only about half her size at this point and my head rested right between her sweet perky tits. I took my erect little cock in all it's glory and position it on her mound of fur and I begin to hump away, she just laid there patiently and I moved my pelvis up and down feeling the friction of her bush on my little circumcised penis and then it happened. I got that nice little tingly pulsing down there and I was done. I had my dry little orgasm on my s****r's pubic area and I was happy. I guess I fell asl**p as I always had after humping my pillow.
The next day Charlotte and I were at the house alone, as it seemed we always were. She came to me and took me by the hand as she did the first time she caught me drawing pictures of naked women. She led me into the bathroom this time and it must have been winter or at least chilly because I remember her wearing a sweatshirt, jeans, and long socks. She started removing her shoes, then she unbuttoned her jeans and slid them off. Then she peeled off her socks one by one and finally pushed her panties down to the floor. For some reason she left her sweatshirt on though, I know she wasn't hiding herself because I had already seen it all. She then leaned over and started unzipping and pulling my pants down then she took my underwear off for me. I asked her what we were doing and she said "showing you what boys and girls do". Then she led me over to the tub and she seated herself on the edge. With only her tippy toes contacting with the floor, her calf muscles slightly flexed, she opened her shapely thighs wide and to my amazement I saw something I had missed before… her pussy. Not like she was so hairy I couldn't find it, quite the contrary, my s****r was well groomed and she loved cutting hair... I just never saw it because she never spread her legs before me.
As I stand there pondering what was before me, she took my penis and begins to message it. I had touched and groped her many times now, but this was the first time she touched me. I think back about how beautiful she was there sitting there on the tub, so inviting. I guess she chose the edge the tub because it happened to be the perfect height while she was sitting and I was standing that our parts met up. Anyway, she played with it till it was totally erect and in it's hard form at the time it was probably about 3 1/2 to 4 inches. I'm guessing this because when she had her hand completely wrapped around the shaft, the end of her palm was touching my pelvis and the tip was still poking out past her fore finger as she made a fist around it. When it was completely hard, she positioned it in front of her vagina and held me by the hips and started rocking me back and fourth. I remember how wet and warm her hole was the first time I went inside and yes it was totally wet. She must have been wanting or preparing for this. I don't know a better analogy besides that it sounded like stirring macaroni when she was working me in and out of her.
I asked her what we were doing and she said, "it's okay sweetie, this is what boys and girls do, does it feel good?". I replied, "yes it does". Sometimes she would do half strokes were she was only pulling me part of the way in and other strokes were all the way until my pelvis touched hers and I could feel her pubic hair brushing and rubbing against my bald pelvis. I looked down and saw a little bit of clear liquid dripping from in between her vagina and my penis and I could feel the tingle coming on. I was about to have my orgasm inside her and before I knew it, I felt my orgasm caused by my s****r pussy. I don't know what happened to her but she tightened up on the inside and then a complete feeling of happiness came over me, and something happened to her as well. She had a look of happiness and I think it was that she made me happy, to this day I am not sure. She slowly pushed me back from her and my now somewhat flaccid penis fell out of her vagina with a bit of fluid, but it wasn't mine, as I wasn't old enough to make semen yet. She took a wet cloth and cleaned me up as well as herself and told me to dress myself as she did. As far as the rest of that day goes, I couldn't tell you what happened if my life depended on it. And as far as the rest of our lives have gone... well I'm 32 now and she is 40, anything can happen, but this is definitely a true story from my youth. I guess my s****r was curious to see what I knew about sex and what would happed and I think it really did amuse her. Why she truly did what she did, i'll never know. Unless one day, she decides to share with me what was in her mind.
I had a dream about my s****r Tuesday night, or should I say Wednesday morning... In my dream, we were at the beach. I don't remember much of the surrounding details but I remember other people being there. My s****r and I went to the car, which must have been a truck or a jeep, something higher off the ground... my s****r wanted to change out of her bathing suit into some clothes and she wanted me to stand guard next to the open passenger door so no body could see. As she stood up on the floorboard of the vehicle to turn around, she brushed her ass cheek across my face then continued to slide her bikini bottoms off, then she turned back around and sat in the seat facing me with her legs open, (just like when she sat on the edge of the tub all those years ago).
Then she pulled me close and opened my jeans, ( why i'm in jeans at the beach beats me, I prefer to wear shorts at the beach). She opens them and then grabs a condom and opens that as well. I remember in my dream that I can't believe this is happening and I’m thinking about my wife a little but I’m looking at my s****r with her with legs wide open showing me that beautiful pussy of hers between those luscious tan thighs. Her knees are against my waist and just then, for some reason, she just tosses the condom on the ground, then takes my cock and positions the head of it right between her labia. She takes me by the hips and pulls me into her. I loved the feeling of her pussy wrapped around my cock and remember pumping into her once and her pussy got real tight and then I had an intense orgasm. I heard what sounded like someone say "Oooh!" then I woke up. Meanwhile in the real world, I sl**p with only my underwear on, mostly because I don't like my junk flopping around while I sl**p, otherwise I’d probably go naked. There lots of times in the middle of the night I subconsciously pull them off. I must have done this at the time. Sometimes my wife curls up next to me when I’m on my back and she lays her head on my chest facing toward my feet, and occasionally she will lay her hand on my cock. Well, while I’m laying there early in the morning having naughty dreams of my s****r, my wife is cozying up next to me and she is awake. She notices I have no underwear on and I have an erection. She decides to grab it and pump it once for fun. What she didn’t know was at the exact same time in my dream I’m inside my s****r and I’m pumping her and when I came in my dream, I came in real life.
Apparently when I felt my s****rs pussy getting tight, that was my wife's hand squeezing my cock and I shot a load across my stomach and chest and some hit my wife in the face, which was why she made the startling sound "Oooh!", and woke me up. I looked at my wife and I was very confused, there was cum on her face and all over my stomach, she asked "what happened" and she said, "I only grabbed it and pumped it once", she didn't expect it to go off. She asked if I was dreaming and I said yes. "What about ?" she asked, and I replied, "fucking you sweetheart". She smiled and got up to get a towel to wipe me off. When she returned as she was cleaning herself and I off, she smiled. Well, that was the story, I know it sounds crazy but it really happened. I don't think that could ever happen again in million years.