Well, I never intended it to happen this way but it is what it is. I have lost count of all the times I've had anal sex with Jennie, and that may not be so unusual or socially unacceptable except for the fact that Jennie is my sister and it all began when she was only 8 years old and I was 15.

We lived near a small town in the Midwest. My father was almost never around so my mother divorced him when we were very young. I don't remember very much about him. The 3 of us were on our own and learned to depend on each other. There weren't many people living around us so we spent a lot of time together. I remember it being a very loving and happy time.

Sexually, I found myself attracted to Jennie and I am sure she could sense this, and that the feeling was somewhat mutual. We were pretty close and could almost read each others thoughts. I noticed that she always seemed to be around when I would get out of the shower wearing only a towel, and would want to talk or play. She tried to be casual about frequently glancing at the towel around my waist. She would sometimes wear an old pair of pajamas that she had long since outgrown, which would pull tight on her crouch showing the outline of her slit. There were a couple rips and torn fabric, exposing some of the skin on her buns and breasts. Though I was quite young I realized she was doing this to test my reaction, as she had plenty of other pajamas that fit her properly. She would walk by a lot or lie down on the floor in front of me watching TV, showing that pretty ass of hers. Sometimes she would glance back to see if I was noticing, with a mischievous smile, and I would look away quickly. But she wasn't fooled, she could tell I was interested and this encouraged her. Mom was around so it didn't go much further than a kind of curious tantalizing tease. When I became 14 or 15 years old Jennie started wearing an old 2 piece swimsuit that was way too small, and as my hormones were becoming active I began to fantasize in private, mostly fantasizing about her. Still, I did not pursue it as the risk of getting caught was too great.

Then one day Mom told us she had to take a job working evenings in a near by town to supplement her child support payments, and that she would be gone a lot so I would have to take care of Jennie. My relationship with Jennie was about to change drastically. That smart little cutie had plans for me.

The first few days that my mom was at work were uneventful. Jennie and I busied ourselves with homework, TV and video games. Then one day, about an hour after mom had left, Jennie approached me with pen and notebook in hand.

"Hey, can you help me with my homework? I need to ask you some questions.”

"Sure, fire away,” I replied.

"Well, it's about sex. How young can people have sex?” She tried to appear earnest, but I knew her well enough to see she was tentative and a bit nervous.

"I guess when they have puberty,” was the only response I could think of. I was studying her; she was not quite herself. She wrote write something in her notebook.

"What if they don't have puberty but still want to have sex?”

I contemplated a few seconds before answering. "Well, they aren't supposed to do that and could get in trouble. Hey, what kind of class is this? These questions are weird."

"It's sex education.” She cleared her throat. "What if they did it but didn't tell anyone so they wouldn't get in trouble. Then what?”

"Did what?” Stupid response, I know.

"Had sex, you dummy,” she laughed and playfully hit my arm. "What if they didn't have puberty but had sex?”

"Well, they aren't supposed to but if they like it I guess it's ok. I mean, people masturbate when they are very young.”

Jennie wasn't writing in her notebook any more. "I bet you masturbate. Boys your age masturbate!” She laughed, derisively pointing at me, yet eager to hear my response.

"Its' none of your business!” I shot back, hoping to tease and embarrass her. "Jen, I bet you masturbate all the time.”

"So if I masturbate than that means I can have sex even if I don't have puberty, right”? She felt triumphant in her logic.

"Yea, but having sex with yourself is different than having sex with another person. You wouldn't know anything about that you little monster! ”

"I know a lot about it! I watch it on the computer!” She shut up for a few seconds, staring at me with those big blue eyes, both of us equally surprised at what she just blurted out.

"Yea, right,” I replied almost to myself, trying to diffuse the tension.

"C'mon, I'll show you,” she quickly said as she grabbed my hand and pulled me to the PC. She began to expertly browse porn sites. I was speechless. Here I was watching my little sister watch porn. I knew I should stop her but I was curious myself. She would ask whether I liked certain scenes and such, but the opinions I offered were vague and noncommittal, but still enough to encourage her to continue. I began to notice she seemed to prefer the anal scenes and would find different ways to solicit my thoughts on the subject, like; "doesn't that look like fun?” Finally she just came out with; "Do you think you would like to try anal sex”?

"Maybe if the right girl wanted to I might try it, I suppose.” I was getting turned on by those porn scenes and I think Jennie was too. My cock was beginning to swell.

She took her eyes from the screen and looked into my eyes. "How about if you try it with me?” There was look on her face I had never seen before.

"You're too little to fit it in there,” my voice cracked. My heart was racing, my throat dry in nervous anticipation.

Unexpectedly, Jennie suddenly laughed while declaring, " I once stuck a carrot in my butt and put it back in the fridge and then mom made it for supper and you and her ate it.”

"Very funny. I hope you cleaned it off. Besides, my penis is bigger than a carrot. So you masturbate with a carrot in your butt, huh.”

Jennie was still laughing a bit when she started saying; "It was a big carrot and I washed it off so nobody could tell.” She laughed again, "and so what if I masturbate with a carrot in there! I put other stuff in there and could fit your wiener there too! I know you like looking at my butt. I see you doing it all the time.” With that she turned around and wiggled her ass, looking sexy in those tight fitting white shorts. I playfully gave it a spank. "Wanna see it naked?” She offered, and started to pull her shorts down then stopped, revealing half of her gorgeous little ass. By now cock was trying to burst through my pants. She turned to face me, "take your pants off and I will too. Ok?”

I was speechless. Here was my little sis slowly pulling her shorts down as I undid my belt buckle and unzipped my fly. She stopped pulling her shorts down at mid-thigh, revealing her little hairless pussy, while she waited for me to keep up my end of the bargain and pull my pants and underwear down. My cock sprang out practically in her face.

"Oooo it looks so nice! It's bigger than I though it would be!” Her eyes got wide and she reached her hand around it. When she touched it I felt like I could almost cum right then. I let my trousers drop to the floor.

Jennie stepped back and out of her shorts, her eye glued to my hard cock. She then pulled her t-shirt off over her head, messing her shoulder length blond hair, revealing the slight curves of her beautiful pre-teen body.

"I know I don't look as good as those girls on the porn videos," she half apologized rather bashfully.

"You look so sexy,” I truthfully, offered, "Look, my cock likes you.” It was rock hard, ready to burst, pointing right at her.

She smiled and bent down to kiss the head of my cock before turning around and walking over to reach under the mattress, showing me her perfect ass in the process. She came up with a large tube of KY.

"Where did you get that?” Little sis was full of surprises.

I stole it from the store when I went there with mom. I needed it for my butt. Don't worry, silly, I studied how to do anal sex online. I know how to.” With that she squirted a large dollop onto the palm of her hand and applied it to my penis, thoroughly massaging it in.” This immediately returned it to maximum hardness. She looked up into my eyes and declared, "It looks like your thingie is ready for anal sex!” She hopped onto the bed, still holding the KY, and got on her hands and knees just as she had seen in those porn scenes she liked to watch. She then applied some KY onto her middle finger and rubbed it around her waiting assole, then inserted it in and out a couple time, before putting her head down on the pillow and aching her back up. She was very quick about it, as if anxious. "There, I'm ready for your weiner.”

It was like I was in a dream state, like I was observing this from a distance. There was my little sister with her sexy little asshole glistening with KY, asking to be fucked. I knelt on the bed behind her and placed the head of my cock against her brown hole, testing her reaction.

"Whoa, ok, push it in but not too hard. Push it in slow.” From her expression I could see she was concentrating. I pushed gently at first, then increased the pressure until her sphincter muscles suddenly yielded, allowing my cockhead in about an inch. "Stop, ouchie, not so fast. Wait!” She tensed up.

"Is it hurting you?” I worriedly asked, not wanting to hurt her, but yet craving more of the feeling of her tight little ass around my cock. "Is it ok?”

"Uh yea, it's better now, push it in a little more, just a little.” I could feel her entire body gradually begin to relax. I slowly pushed it in about half way. "Ooo stop. Ok go a little more. Now stop.” Jennie was breathing heavier now. She pushed her ass onto my cock another half inch, and then, after a pause, I pushed it until it was most of the way in and stopped.

"Does it feel ok to you now?” I was concerned but also wanted permission to begin fucking her ass more vigorously.

"Yea, it stopped hurting,” She turned her head looking back at me, " I thought your thingie would be smaller. That's ok, It feels good now. Does it feel good to you?”

"It feels awesome! It's the best thing I ever felt!” I really had no adequate words to describe the heavenly sight and sensation of her tight little ass wrapped around my cock.

Jennie, encouraged by my exaltation, pushed her ass another half inch back onto my penis. Instinctively, I pulled back and thrust forward with increased fervor, until I ejaculated a huge load into her clenching colon, somewhat prematurely. It felt like half a cup. I couldn't help. I had never felt anything so intensely erotic. Jennie giggle, "I can feel you squirting your spermies inside of my. They're swimming around in there now.” Then she smiled back at me. "See, I told you anal sex would be fun.”

I looked down to see my cock buried almost to the hilt in my sisters ass. Her small butt made my cock look disproportionately large, and I was amazed she could handle it. Then I looked at the clock. "Shit, mom will be home in half an hour! We gotta clean the kitchen and stuff." I pulled my cock out of her too quickly and she dribbled cum out of her ass onto the sheets. "Ahh hey,” she yelled, "Don't pull it out so fast!” She jumped up and ran to the bathroom, leaking brownish tinted cum on the carpet. While I frantically cleaned up the mess I could hear loud squirting farting sounds from the bathroom as Jennie expelled the large load of cum from her newly stretched assole.

When mom came home I was doing dishes in the kitchen while Jennie was getting cleaned up in the shower. "How'd it go today,” she asked.

"Good, I replied, "I helped Jennie with her homework."

Mom smiled. "Thank's for watching her. She is so lucky to have a big brother like you. Is that the washing machine I hear?”

I was washing the sheets that Jennie had dribbled cum on. "Yea mom, I thought I'd do a little laundry.”

Mom kissed my cheek. "Thank you dear, and I'm really lucky to have a son like you.”

I wasn't paying much attention, though. I was already daydreaming about the next time I would get to fuck Jennie's ass.