A boy's first sexual experience with an unlikely girl
Everybody who knew my family knew that Jessica only put up with me because I was her little brother, but deep down she hated being around me all the time. I guess I tended to get on her nerves as any typical sibling would. Last summer we took a family vacation up to the mountains for a week and all Jess talked about the whole trip was how unfair it was that she, being a 17 year old girl, had to share a room with me, a 15 year old boy. I really didn’t mind because I planned on being outside the whole trip, either riding my four-wheeler or fishing, two of the three loves in my life. The other being hot, sexy girls. A nice firm pair of tits and a round bubble butt are two qualities that I always admired in girls, well except one girl, Jess because she was my sister so she didn’t count. I remember when I first started noticing girls, I had to fight not to stare at even her when she bounced around the house in a pair of booty shorts and an almost see through white tank top with no bra underneath. It was especially nice when it was cold because her hard nipples would almost poke right through the fabric of the tank top. Enough about that.
We arrived at the cabin and I immediately grabbed my fishing pole and headed down to the river. Mom yelled for me not to be late for supper as I hustled on down the path. After a few hours, and a cooler full of fish, I heard dad coming down through the brush to fish some with me before supper. Just as I reeled in another fish, I felt a push and I almost went face first down in the water. It wasn’t dad coming down the hill, it was Jessica and she was giggling at the fact that she almost pushed me in. “Don’t do that!” I told her, “I’ve got my phone and wallet on me and YOU don’t want to make me fall in and get that stuff wet.” She rolled her eyes like she usually did when I talked and said, “whatever”. “What are you doing down here anyways?” I asked her. “Nothing else to do, plus mom told me to come tell you that supper was going to be early, like right now, so come on to the house.” “Fine” I was my only response. That was not nearly enough fishing time for my first day. I left my rod and reel and my bait because I planned to come back after supper and started back up the hill towards the cabin. Jess was just ahead of me and I hadn’t noticed earlier, but she had on a pair of those black booty shorts and the way she was walking up the steep hill made half of her ass hang out of the bottom of them. I felt a tingle down in my pants as I watched her ass bounce up the hill. Before we got to the cabin my dick was rock hard. “Race you to the door!” she said, so we both took off towards the back door of the cabin. She was way ahead of me so she barely got there before me and I was running so fast I couldn’t slow down in time and the front of me met the back of her. Almost as if it was meant to happen, my erect cock pressed firmly between her ass cheeks and I know she felt it because she turned around and gave me the oddest look. With a slight jiggle of her ass, she walked on in the kitchen and I was left standing there, harder than I had ever been. Supper was boring and we ended up talking around the table until dark. Strangely, I was tired and decided to go on to bed while everyone else opted to watch tv. The little room was set up with two beds on each side and a nightstand in the middle. I stripped down to my boxers and got under the covers in my bed. As I lay there, I couldn’t help but daydream about Jessica’s ass, the way it looked hanging out of those shorts and the slight impression of her pussy that could be seen between her legs. I was full of mixed emotions because she was my sister! But I still couldn’t help my mind from wandering. As I started picturing her totally naked, my cock quickly got hard again. I wanted to pull it out and play with it and I knew I would hear footsteps if she was coming in the room. So I folded the covers down, and slid my dick through the hole in my boxers. It quickly went from being a soft penis to a nine and a half inch hard, throbbing cock. I stroked it wildly, fantasizing about my sister who was just in the other room. I had not realized how tired I was and that I was drifting off to sleep with my cock out and in my hand.
I awoke to the sound of the door closing and the light turning on. Before I could move, there was Jessica, standing at the foot of my bed, while I had my big, hard cock in my hand. I covered it up quickly with the covers and she just smirked. “You think that’s the first dick I’ve seen? Don’t be so embarrassed. Gah.” She then turned the light out and got into her own bed. After a few minutes I kept hearing her bed squeak and a juicy noise here and there so I asked her what was she doing. “What the hell do you think I’m doing . . . I’m so horny, plus I masturbate just about every night before I go to bed. Are you still jacking off?” WHAT! My sister just told me she was playing with her pussy and asked me if I was jacking my cock! The sound of her asking me that almost made my cock explode. “Yea” was my only response. I heard her get up, then I felt her get into my bed. “You know, we are brother and sister, would it be wrong for us to, you know, help each other out?” “I guess not” I said. With that, she slid her shorts and tank top off and the next thing I felt was as close to heaven as I had ever been. Her firm 36-c breasts pressed up against me as she took my hand off of my cock and put it between her legs. Up until this point I had only made out with a girl so this was all new to me. I stuck my finger in her hot, wet pussy and began to wiggle it around and pull it in and out. I found her tits with my mouth and licked her puffy nipples while she wrapped her hand around my cock and stroked it up and down. I could feel my cock throbbing in her hand as she jerked it and she began to moan a little as I was learning how to play with her pussy. Just as I was really starting to enjoy her tits pressed up against my face, she pulled them away and I thought I had done something wrong. To my surprise, she climbed up on top of me and sat her warm, wet, and shaved pussy right on top of my hard erection and slid it back and forth until I thought I would blow a load all over my stomach. She bent down and pressed her bare breasts against my chest and licked my face playfully. She whispered “You know you have a really big dick don’t you… and you know I want it inside me… but I know you don’t have a condom.” I slyly whispered back “oh yes I do.” “Well put it on stupid!” she said. I reached down into my backpack, because I was always prepared, and pulled out a rubber, which I was so glad I had! She wanted to put it on me and I couldn’t argue. She slid down between my legs and opened the condom and said “First I need to have a little fun with you.” The next thing I felt was her grab my shaft and shove the bulging head of my cock in her hot little mouth and roll her tongue all around it. I almost jumped through the roof the pleasure was so intense. Then she began to slide the whole shaft in her mouth inch by inch until she had the whole thing inside of her and I could feel the head of it pressing the back of her throat. She gagged a little and let it slide back out as she giggled. She deep throated my hard dick for a while longer and then put the condom on for me. She got up on top of me, straddled my huge rod, and sat down on it. For the first time, I experienced the feeling of the warmness and tightness of the inside of a girl’s vagina. She grinded back and forth and moaned so faintly and I could tell that she was enjoying my dick, all of it. She grinded faster until I thought the bed would and let out a long lasting sigh and layed on top of me, my throbbing cock still inside of her. “Did you just have an orgasm?” I asked her, and she replied, “Wouldn’t you like to know.” But I knew she had. “Now it’s your turn, let’s see how long you can last.” With that she sat back up and this time, instead of grinding on my cock she started raising her ass up and slamming it down on top of me. I could feel every inch of me sliding in and out of her wet pussy. Her firm ass bounced against my legs and she reached back and played with my balls with she rode up and down. Her perfectly round tits bounced in a circular motion and I reached up and grabbed one while she fucked fell down on my dick over and over again. “Tell me when you’re about to cum” she said while breathing heavily. I was almost at that point but her hot pussy felt so good I wanted to make it last for as long as I could. Plus, I figured if I could make Jessica like fucking me, then she would want to do it again soon. She leaned down and pressed her tits into my chest and the only thing moving was her ass up and down and I couldn’t take it any longer. “I’m about to cum Jess” I said in a low voice. She pulled my cock out, pulled the condom off and began to jack it off. She stroked for about thirty seconds and I could feel the head swelling up and my veins bulging out on my cock. I had never been this hard or felt this kind of pleasure and I knew I wanted more of it. “Here it is” I said just before I shot a hot load of cum. I felt Jess put her mouth over the head of my dick as it shot wad after wad of cum down her throat. After that, she patted me on the stomach and tip toed over to her bed, climbed under the covers and went to sleep. I was too excited to sleep but tried to anyways. This was only day one of our mountain vacation. TBC.