Where it happened: Sister's Room
When I was young my parents got divorced. It wasn’t all that bad because with my mother back in the dating scene, we were pretty much left up to our own devices at night. My sister and I were close and we took good care of ourselves, with the occasional brother-sister squabble here and there. Nothing serious.
The nights alone progressed along with my growing curiosity about the opposite sex. Without knowing it, my sister would occasionally sit on the couch with her legs open just wide enough for me to catch a glimpse of her cotton panties underneath. She always wore pajamas that were basically a one-piece, long dress-like thing. She had several pajamas like these, some shorter than the rest. I couldn’t help but get excited when I could see something that I wasn’t supposed to. I know it was probably wrong, but there was no harm in looking. After all, I’d taken to masturbation like it was a requirement for life that year and having a little something extra to think about certainly made the job easier.
When it was time for bed one night, my sister and I were just hanging out watching TV in her room. She was on the bed and I was seated on the floor. Something came up in conversation that prompted her to smack me on the head with her pillow jokingly, to which I responded by leaping up to tickle her into a frenzy. All was fun and games. I reached for the pillow and covered her face with it as she laughingly begged for mercy. It was at this point that I realized she had her legs completely opened up as she and I played our stupid game. Being the little horn-ball that I was, I intentionally kept playing our flirty little pillow game so I could openly stare at her cotton-covered crotch. I was in awe.
I was pushing out a pretty sizeable erection after a few minutes and decided to retire to my room for some “exercise”. I remember jacking off to the thought of fucking my sister for the first time ever that night, and I came almost instantly. I fantasized about her coming into my room and catching me in the act, then raising up her nightgown to show me her most private of parts. What a fantasy!
The next time I had the opportunity to watch TV with my sister before bed, I joined her on the mattress. No big deal. I started poking fun at her again and sure enough, the flirting began again. I use the term flirting because she always had a bashful little grin on her face that said, “I have dirty thoughts and I know you do too”. It felt like a game of who would make the first move. Or was I just making that up? Was it my hormones taking over? Questions I couldn’t answer at the time.
Anyway, once again I had her on her back with the playful pillow over her face and her little legs open wide (almost unnecessarily wide this time). I decided to be bold without being too honest, and got on top of her in a pretend move to keep our little game going. My raging hard on was right on top of her pelvic bone and I hesitated about having my dick so close to the opening under her panties like that. She didn’t seem to mind, and actually lined herself up with the head of my dick!
My head was racing. What was I to do? I had gotten this far, right? Might as well keep trying! I set my hard headed penis right on top of her crotch and pressed on her with it as I pretended to reach above her head for the pillow (note that by this time it was resting over her eyes with no help from me). She pushed back! Holy shit!
At this point I didn’t know what to do. I was so turned on and wanted to see how far I could go with her, but I knew what was at stake. What if I was wrong and she was just playing around?
My head go the best on me and I playfully leaped off the bed onto the floor, taking the covers with me. She removed the pillow from over her eyes and we laid there in silence watching TV for a few minutes. Eventually she said that she was getting chilly and turned onto her stomach, pressing her arms down straight against her side. Her little nightie was hiked up JUST enough for me to see the outline of her ass cheeks as she laid there, face down in that pillow. I could stare at her body without guilt once again and I certainly took the opportunity.
After a minute of hesitation, I hopped on the bed between her and the wall while remaining wrapped selfishly in the blanket. She was next to me more towards the middle of the bed, still without cover. Upon another playful complaint of the chills, I opened the blanket and covered her with both it and me. I flopped on top of her back, carefull to rest my dick in the crack of her ass. Agian we laid in silence.
If you’re a man reading this, you know that there is a certain way to make the blood rush to your dick and make it swell. As my hard penis was against my sister’s ass crack, I flexed this muscle and sort of poked her a little to see if she’s react.
She squirmed back! She also moved just enough to encourage me to try harder. This time I full-on pushed my cock against her ass and she moved back against me again! I was so hard! Here I was, basically dry humping my hot little sister’s body and she was practically begging me to keep going! Our private parts squirmed against each other for a few minutes until something completely uexpected happened. . .
All of a sudden and out of nowhere, she slightly raised her ass off the bed and slid her panties down to the bottom of her ass cheeks with her thumbs. No words were exchanged. She just did it, then laid there with her thumbs still in the sides of her panties and my dick caught in the cotton between her legs. My pajamas were loose-fitting shorts so I was pitching quite a tent. Part of me wonders that if my dick hadn’t gotten in the way, would she have slid them all the way off? Regardless, her naked, warm ass was against the flesh of my lower stomach since my shirt has slid up, and I was now able to confirm that this was not a one-sided game anymore. We both were now into something extremely forbidden but uncontrollably erotic and hot. There was no turning back. I mirrored her behavior and rose up to slide my shorts down to my knees
Again, we froze and laid there in silence. After what felt like forever, my little, naked sister moved her thumbs out from under the straps of her panties and put her hands up around her face. I took the small window of opportunity to move with her and pull my dick back out of the tangle of her panites and replaced it at the opening of her hot, tight, fleshy opening.
There it was. My dick was knocking at her door and I was ready to come in. Her legs were still together so there was nothing I could really do other than test the waters one more time. I flexed my dick against her. She returned the request with her own attempt to let me inside of her, and wiggled back against my penis. Her legs remained closed. We resumed our weak attempt at sex by continuing to rub against each other like this for a minute or two.
Finally, the moment that I has jerked off to for so many nights arrived. My naked sister parted her knees a little and I instantly moved so that my adolescent prick touched the hot wetness of her virgin fold. This was unbelievable. It must have been out of instinct that she arched her back a little as I slowly lifted a small protion of my wieght off of her. I took my left hand from off the bed and steered my penis into her so that the head of it just barely sat inside of her on its own. I stopped.
“Yes or no”, I said.
“Yes”, She whispered, face down into the pillow.
Permission granted. I pushed forward into her and back out in quick, short little thrusts, a little longer each time until her wetness spread up my entire shaft. I will always remember the feeling when I finally got the length of myself all the way into her. Being inside of her felt so hot on my dick. She was dripping wet. The scent of her oily vagina was strong and I liked the unique smell (still do!).
I slid in and out of her for about two minutes. The act was nearly silent, exzcept for the way she was breathing. She would take in big, deep breaths, hold them for a few seconds, then let it out all at once. Deep breath in. Hold it. Then big exhale. Over and over again. Each time that she started to hold her breath, she sort of grunted a little which made her vaginal muscles clench my penis a bit. If felt sooooo good.
Eventually, an all too familiar feeling crept up on me. I was sliding in and out of my naked little sister and I knew I was about to cum at any moment. When the moment came, I pushed all the way into her a sprayed her insides with my adolescent load of semen. My dick convulsed as several waves of cum shot into her. She sort of moaned at the awkward feeling of being filled up with cum as I let myself unload inside her. Perhaps her moan was a reaction to taking the length of me into her, but either way it was a moan of pleasure, not pain. I just let it all go up inside of her.
I laid there with my dick inside her for a few minutes after I came. It softened and made its retreat on its own. Again, complete silence. This time it was slightly uncomfortable. After reality came rushing back to me, I got up and pulled my shorts up from their current location around my knees. As I left the room for my own, I caught a quick glimpse of my hot little sisters cum-filled pussy staring back at me. It was quite a site.
I spent a few minutes freaking out in my room. What had I just done! What if we got caught! Did she want me to do that of was I being inappropriate? What if she told on me? I’d be in sooo much trouble! I had to go upstairs to get a drink of water or I was going to pass out. I headed out the door.
Upstairs I could hear the TV on in the living room. I knew she was in there. I poured my water. There I was with water in hand, and I could either go back downstairs of into the living room to see what kind of trouble I was in. I plopped down into the easy chair across the room from the couch where she sat, avoiding eye contact. A few minutes passed and a commercial break snapped into a movie trailer.
“I want to see this”, she said, as if nothing had happened.
“Me too”, I replied.
I looked over at her with an embarrassed smile and she returned it. I had a feeling that our first time would not be our last.