I was lying on my bed after basketball practice imagining six blond cheerleaders holding me down and stroking my body. I’ll admit that probably sounds weird but it was my most frequent fantasy. I would be either tied or held down and molested by any number of girls, all blond. My painfully swollen cock would lie ignored on my belly until I began stroking it off imagining one of the girls had finally taken hold of me there. In those days I had a thing for blonds and it seemed I always had a hard on thinking of them. I admit that I still have a thing for blonds, but this story isn’t about them, it’s about my sister Jenny who’s hair is the color of polished mahogany.

Jenny was the cheerleading captain and very popular. Our house was like cheerleader central. Jenny was the only brunette on the squad. It was cool the way she stood out at games, like the warrior princess Xena, among all the blond cheerleaders. She looked like she should be the captain. I was proud she was my older sister. Most of the girls were seniors, and all of them, even the two juniors, treated me like I was just Jenny’s little brother. I guess it was because I was a sophomore even though I was only a few months younger than some of them. The only one who was always friendly to me was Alyssa. She was the prettiest of them all and the likely replacement for Jenny as captain the next year. Alyssa was the reason I worked hard at basketball practice.

Whenever I indulged my fantasy about being restrained by the blonds my boner felt like it was going to burst. That’s exactly the way I was when Jenny suddenly opened my door and barged in and saw me almost ready to shoot.

“Oh My God!” She said and then after a pause added in a hard whisper, “Randy, you’re even bigger than daddy!”

She turned her head to peek back into the hallway, closed the door and locked it, then walked over and sat on the edge of my bed.

“Go on Randy, I want to see,” she said.

I had whipped my pillow down to cover myself and held it there with both hands, pressing it against my stomach.

“No” I said. “Go away!”

“Come on little brother, I masturbate too, it’s only natural,” she said leaning in to put her hand on the bed between my legs so her wrist pushed against my thigh and the pillow high enough to graze my balls. “Please let me watch you cum.”

“No, no way! Let me alone Jen.” I guess I could have rolled away onto my side, but I didn’t.

“My poor little brother, and with such a big hard-on.” She said, “Come on, dinner will be ready soon, Maybe you need help?”

With that she moved her hand up to slide her fingers under the pillow and took a firm grip around my shaft.

“If you don’t let me watch I’ll scream for mom and dad.”

She began squeezing the base of my cock almost in rhythm to my pounding heart and her squeezing was making me really hard again. I could feel her hand flexing around my cock and my hands could feel it flexing beneath the pillow. The memory of that double sensation remains one of the most vividly erotic memories of my life. Finally I resigned myself. I closed my eyes and let my head fall back onto my bed.

When my hands relaxed the grip on the pillow Jenny pulled it away, tossed the pillow at my face and said, “That’s better, little brother.”

“Quit calling me that.” I said putting the pillow behind my head.

“Just relax and let me see you cum.” She said teasingly.

Her hands on my cock felt so good. She milked my cock and fondled my balls for over five minutes. She squeezed and released as she moved her hand over and over from base to head but I was no closer to cumming. I kept my eyes closed. It felt good, but it was so weird, I mean this was Jenny, my sister, the most popular senior at school. I couldn’t stop thinking of mom and dad right downstairs believing we were doing homework.

Then I felt her mouth and tongue on me working the tip, squeezing it, licking it and even gently gnawing it with her teeth. Oh god, it felt so good. My neck strained as I lifted my head to watch. I wanted to hold her hair away so I could see more, but I was afraid she’d stop. I was still a virgin. I mean who could blame me for not wanting her to stop. Here I was 16 years old and nobody but me ever touched my hard cock before.

She took hold of my hand. When she released my cock from her mouth she guided my own hand to my shaft. “Go ahead, finish it off, I want to see you cum.”

She knelt over me and cupped my balls, her fingers pressing up on me right behind them. She placed her other hand on my forehead. I lowered my head back onto the pillow and closed my eyes again, stroking myself. I tried to envision her friend, Alyssa, beautiful blond Alyssa, leaning over me holding my head down, her other hand on my balls, urging me to cum. I imagined it was Alyssa telling me to cum and she was going to lick it off my stomach. I opened my eyes and saw Jenny instead, her rich dark hair swaying back and forth as she rocked in excitement while telling me she wanted to taste my cum.

I closed my eyes again and I came, oh Christ how I came. I felt the first shot hit my neck right below my chin, and then five or six more shots squirted up onto my chest and my stomach. I opened my eyes to look down just in time to see Jenny put her mouth on my cock again. Then she looked up at me, released my cock and pressed it to my belly with her hand.

“That was so cool, Randy,” she said with a smile and began to lick the streaks of cum from my belly and didn’t stop until she got the last bit from below my chin.

A little while later we both giggled contagiously all through dinner causing both our parents to wonder and laugh curiously along with us.

Two afternoons later both our practices were canceled giving us two hours home alone. We grabbed a couple of Cokes from the fridge and ran to Jenny's bedroom. We stripped as fast as we could, laughing and giggling as we did. Jenny kept on her bra and panties but pulled my underpants down and put her mouth on my cock right away. My hands were gripping her hair and when I started pulling her head onto my cock with more force she made me let go of her hair.

Then she made me lie down on the bed and knelt on the floor between my knees saying, “Your cock is too big to be forcing down a girl’s throat Randy. You were making my eyes water with that thing,” she said, half serious and half laughing. She took off her bra and pushed her tits up against my groin so my cock slid right in between them.

Her tit’s, big and soft, looked and felt so good around my cock. “Ooh, wait, don’t move,” She said.

She got up and walked over to her dresser. I watched her tight ass jiggle ever so slightly and I felt proud again that she was my sister. She grabbed something on the dresser and walked toward me with a restrained smile as her tit’s swayed ponderously. I felt excited. This was the first naked girl I had seen in person. She looked perfect. I marveled at her tits and couldn’t take my eyes off them. I realized I had gotten used to seeing implants on porn stars and that Jenny’s were so much sexier than the ones that looked like softballs slipped beneath the skin. My cock was raging again.

Jenny knelt down between my legs again and with a big smile held up the bottle of baby oil saying, “This will be fun.”

Holding my cock straight up with two fingers she let a stream of oil drip down to run along the bottom side of it all the way to my balls.

Then with both hands she began stroking my cock and massaging my balls and rubbing the oil on my thighs.

"You have the most beautiful cock," she murmured, half to herself.

When either hand got to the head of my cock she twisted it like it was a slippery doorknob before letting it go. I let my head fall back onto the bed in ecstasy wondering why I never thought of doing that to myself with the oil.

“Wait, watch,” Jenny said and released my cock.

When I lifted my head Jenny had the bottle of oil upturned in front of her. She squeezed a stream down onto her boobs. Then she began massaging them with her hands. Oh God, they looked so sexy and inviting. I wanted to touch them with my hands and mash my face into them. She did something even better. She leaned forward and smothered my cock with them. She began bouncing her whole body up and down to slide her tits up and down over my cock, and soon, even though she wasn’t taking my oil covered cock into her mouth, she was playfully sliding all parts of her body along the sides of my cock.

She rubbed her chest and neck and even her cheeks and forehead against my slippery cock before bringing her tits back to smother it. Her body glistened with the oily sheen. Suddenly while she was jacking me straight up and down with both hands my balls tightened and I blew like a geyser onto her face and over her neck and tits. I was glad our parents weren’t home or they surely would have heard my wonderful agony.

After that Jenny blew me or gave me a hand job as often as possible. Every time our after school practices were canceled and we could be home for a while before our parents came home from work. We would go to one of our bedrooms together and she would suck my cock and either watch me cum or swallow it all. After each time she made me swear that I would never tell anyone.

“Nobody can ever know, nobody at school, especially not mom, and even more especially not dad,” she warned. I already knew this had to be our secret.

Jenny never kissed me, then or ever. Sexually I mean. Yeah she’s given me those polite public kisses that people expect a sister to give her brother at times and an occasional closed mouth kiss after sex, but she never kissed me passionately. I guess I understood why, even though I really wanted her to kiss me deeply and passionately more and more as my love for her grew.

Jenny made all kinds of rules I had to obey. I was not allowed to stick anything in her pussy, not my fingers and especially not my cock. She would let me watch her masturbate sometimes, and she even got a vibrator that she would use, but I was not allowed to use it on her. I could only watch. It drove me so crazy not being allowed to fuck her.

I began to constantly fantasize about fucking my sister. I often beat off while watching her masturbate with her vibrator.

Her friends still hung out at our house, but not as often. And when Jenny knew our parents weren’t going to be home she didn’t invite them over. She wanted to keep the time for us and I was glad even though I liked when they were around. I especially missed my blond angel, Alyssa.

Even after a month of oral sex with Jenny I was still a virgin. Not only had I never fucked anyone, I never even felt the inside of a girl with my fingers! When I begged Jenny to let me at least use my fingers she always said no. She said that would just make her want my cock in her which could never happen since we were brother and sister. My love and desire for Jenny grew and grew. In my fantasy of blond girls holding me down, I began imagining, not Alyssa or one of the blonds, but my warrior sister Jenny straddling me as I pumped my engorged shaft up and down into her.

By the time basketball season was over and baseball season began Jenny had already insisted that I learn to return the favor.

“It’s important that you know how to pleasure a girl with your mouth.” She said.

At first I refused, repulsed by the idea. Then we started watching internet porn together. The idea of licking her pussy still didn’t appeal to me, but a couple of times while she was blowing me she took her fingers from her wet pussy and put them in my mouth. I got used to the taste and got to like it and eventually got past my squeamishness about it. Soon I was licking her pussy every time we were together. She would coach me along, and I wanted to please her even though I didn’t seem to very much.

After the first time we sixty-nined I decided it was the greatest thing ever and it’s all I ever wanted to do. It was nice that instead of her coaching all I heard were the gurgling sounds of her throat working on my cock and the lapping smacking sounds of my tongue. One afternoon we spent almost an hour doing that, switching who was on top a couple of times and even doing it side by side. The first time I licked across the tight little pucker of Jenny’s ass, something I had seen guys do online in porn, it got me excited just as much as her. I blew my load in her mouth almost immediately.

She said she really liked how I licked her there and never even thought about anything so naughty. The next time we were together I knelt on the floor next to the bed and licked her pussy for a pretty long time. I teased her lower until she begged me to lick her ass. When I eventually let my tongue play across her tightly closed little anus she pulled her legs back to her shoulders and hooked her elbows inside them behind her knees. It made it easier to tongue her ass.

Finally I couldn’t take it any longer and I violated her rule and pushed an index finger of each hand into her pussy. MY GOD, it felt so slippery and creamy inside there! She didn’t complain or stop me, but began to get really excited and started moaning. So I added my two middle fingers as well figuring that all together that would be like the thickness of my cock and she yelped a little at first and then begged me to keep pushing harder.

I was amazed at how slick and gooey her cunt felt all the way up inside. I remember what she said about how it might make her want my cock and I hoped so because mine felt so hard it was about to burst. With two fingers from each hand inside her the best place for me to lick was her ass, so I went licking her there like I never did before. I pushed so hard with my tongue it went inside past the tight little pucker. I could feel the hole close down on my tongue and force it out, but I just pushed it harder until it went in again That’s when the first orgasm I ever gave my sister began, and it was unlike any I had seen her give herself. Her pussy began gripping on my fingers really hard, but I kept pushing hard into her. I admit that she was helping me by furiously rubbing her clit with her fingers.

When she began groaning and swearing and urging me deeper I looked up and was actually frightened by the strain on her face and her neck as she lifted her head and began just repeating “OH GOD, OH GOD…” over and over, and then she sprayed right into my face yelling “OH MY GOD and OH SHIT” the whole time.

Even in all the porn we watched we had only seen one episode when a girl squirted before and we had determined it was fake. Jenny’s squirt really took me by surprise. It was just one long blast. I stuck out my tongue and licked my lip. It was different than her pussy juice but didn’t taste bad. I waited for another, but even with her again rubbing furiously and my four fingers still in her it didn’t happen. At least not right away.

I went down and put my tongue on her ass again. Then while still working my fingers into her pussy I pushed my one ring finger, now dripping with her juices, into her ass and watched her orgasm build all over again. She blasted again but this time she kept rubbing so hard her fingers cut the spray into many directions and made everything wet without getting me in the face with too much. I lapped as much of it up as I could.

When her orgasm passed we started laughing together, a giddy, happy, silly laugh. I had slowly, almost reverently taken back my fingers and she let her legs unfold and bend at the knee over the edge of the bed. I climbed...