Jenny and I have been best friends for as long as I remember. As kids, we were forced to be as we lived too far from any neighbours out in the country. You see, mom and dad seemed to be two loners who stayed away from people for some reason. We had a house out in the country with plenty of land to surround it. Jenny was a year older than me, but since she had no one to play with, we became playmates from the day that I was born. Mom told me that Jenny couldn’t wait until I could crawl to play with me.
Whenever we went in town shopping with mom people though we were twins as I was generally larger than Jenny for my age and that made me her almost exact size until she hit puberty and had a major growth spurt. It took me a couple of years to catch up to her height and surpass her after my own puberty.
While we were young we were home schooled, which increased our dependence on each other and closeness. At fourteen for me and fifteen for Jenny, we were enrolled part time in the nearby town’s high school to finish continue our education beyond what my mother could deliver.
Like every other human, during puberty Jenny changed quite a bit. Her cuteness turned into a womanly beauty. The baby fat disappeared, and magically moved into different places to give her very soft female curves. A lot of that fat seemed to move to her tits specifically. By fifteen she had way more than handfuls. Guys started asking Jenny out, but unfortunately for her, mom restricted her dating.
So while at school we interacted with as many people as possible, during the rest of the day we were alone together.
At seventeen I tried out for the football team like every young man seeking to attract girls. I proved that I was damn good at football and the coach put me on a weight-training program after the first season. I firmed up and grew hard and trim.
Jenny seemed start noticing me, her own younger brother, for the first time. She started flirting with me with me like the cheerleaders flirted with the rest of the team. Eventually, she started watching me as I worked out in the basement. I caught her looking at me with some unfamiliar looks in her eyes.
It was just after her eighteenth birthday when Jenny started taking a more direct interest in the way I looked. One day, Jenny announced that my hair sucked as all the cheerleaders made fun of my messed up hair.
“Jake, you have to do something about that mop that sits on top of your head.”
“What about my hair?”
“It’s ugly. Stacy was making fun of you the other day. She said you look like a little messed up child with that hair.”
“That’s what she said. Your hair is always messed up and doesn’t look good on you.”
“I don’t care what that slut thinks about my hair.”
“Why? It’s not like I’m going to date her any time soon. We’re stuck in this place you and I and there is no reason for me to care about what some random girl thinks about my hair.”
“Well I do.”
“Yeah, I agree with Stacy. You could look much better if you fixed your hair.”
“I have no idea how to fix my hair.”
“I can help.”
“You can? Are you a men’s barber now?”
“Don’t be silly, I don’t need to be a barber to fix your hair. I fix mine and that gave me plenty of experience fixing hair.”
“Not whatever, I will fix your hair and you’ll thank me later.”
We had a den-like room in the basement where Jenny and I hung out while the folks stayed upstairs. Mom and Dad never came downstairs.
Next Monday I was down in the basement watching the game when Jenny came down the stairs with a set of brushes and combs and some other goop in jars and spray cans.
“It’s time to do something about your hair, Jake.” Jenny announced as she came to stop in front of me just as the Cardinals were getting ready to try a long field goal.
“You’re too good-looking to go around with hair like that!”
Before I could tell her to move and let me see the TV, Jenny walked to the couch and hopped on top of me. Suddenly, this squirming, lovely girl was all over me. I wrestled with her like we did as kids, but my heart wasn’t in winning any longer as Jenny snuggled over my lap. I was shocked. She straddled my lap, one knee on the cushion on either side of my thighs. As she leaned forward to work on my hair, she pushed her tits into my face.
I forgot all about the football game as Jenny started brushing my hair. Her cantaloupe-sized, braless titties swayed back and forth, brushing my chin. The nipples hardened through her thin T-shirt, and poked at my face.
My cock got as hard as a steel pipe in about three seconds as cocks wont to do do when their owners get tits in their face. Jenny didn’t stop brushing my hair even though I knew that she had to feel my cock pushing up against her crotch. She squirmed her legs wider, sort of settling down over my lap with her pussy sliding over my bulging hard-on. Her brushing picked up a steady pace; so did her hips. My sister moved over me, dry-fucking my cock through my pants. I moaned, unable to stop the cum from surging up out of my balls.
I came in my pants right under my sister’s humping pussy!
My hands tightened on her waist as the intense spasms hit. I felt the hot rush of cum spilling into my underwear. When I opened my eyes again, Jenny was watching me, her own face flushed with passion. I started to apologize, but Jenny wouldn’t allow it.
“That should do it for tonight,” she quickly said as she hopped up from my damp lap. “I gotta go do my homework.”
Every night for the next week, Jenny did the same routine. She’d tease me as she combed my hair, finally making me shoot a wad of cum in my pants, then she’d get up and leave.
Her outfits changed over the week, getting more and more revealing. Her pants and old T-shirt became a skirt and sweater or a loosely buttoned blouse.
My hands wandered, caressing her thighs and back, but I never got the nerve to grab her tits, even though I was dying to feel those twin mounds that kept brushing my face and chest. Each time I’d just about get ready to feel her up, my cock would erupt in a creamy flood and end everything for another evening. Needless to say, neither of us told the folks what we were doing down in the den.
About a week after it started, Jenny suggested that my hair might be easier to manage if I washed it before she worked on my new style. I took an early shower and went down to the den with a short robe wrapped around my body. I looked into the living room before going down the stairs. Jenny was there, talking to our folks. She saw me as I passed, still towelling my hair.
I waited anxiously for Jenny. She slowly came down the stairs a few minutes later with her combs and brushes. Jenny had changed her clothing. She had one of her short skirts again, and this time she was wearing a half-shirt that just covered the bottoms of her beautiful breasts.
I was sitting on the couch in my usual place. My robe was untied and only loosely covering my lap. As Jenny started to get on my lap, I flipped open the robe, thinking that I’d shock my teasing sister. But I was the one shocked. She saw what I was doing, yet she went ahead and straddled my lap anyway. Jenny’s skirt rode up as her crotch came down on top of mine.
“Jesus, Jenny!” I gasped.
My already hard cock touched bare fur!
Jenny was naked under her short skirt. I was still a virgin on that memorable night. She moaned as she felt my steely hard-on touching her cunt. She looked straight into my eyes, this time forgetting all about the brushes and hair spray.
“Ooh, yes,” she whispered. “That’s what I’ve been wanting to feel, Jake.”
I didn’t know what to do. I never thought past the part where Jenny would be shocked by my naked prick. Yes, I dreamed about my sexy sister a lot. I guess that I secretly wished for her to jump my bones, but I never really thought it would happen.
Jenny moaned softly and reached between us. Her fingers found my throbbing cock. She curled her soft hand, pointing the head of my boner up into her furry heat. My sister raised up. When she came back down, she impaled herself over my prick.
“Jesus, Jenny!” I hissed in stunned awe, my vocabulary seemingly stuck with those two words.
Jenny’s face was scrunched in an expression of pain.
I held still and waited for her.
“Are you ok?”
“Yeah, I’ll be ok in a bit. It’s a bit painful and I need some time to get used to the pressure.”
“Take your time sis.”
It was agony for me. While I didn’t move, the feeling of being inside a pussy for the first time in my life was unbelievable. Jenny was so tight. Her warmth and tightness around my the first couple of inches of my cock felt unbelievably good and threatened to push me over way too quickly. I bit my own lip to ward off the impending orgasm hoping that Jenny would be ok soon.
It took few minutes for things to change. I felt more friction as Jenny raised up a bit and dropped back down.
“Holy shit sis, you feel so good. I don’t know if I can hold it long. Your pussy feels amazing around my cock. I sure hope I don’t blow too soon.”
“Don’t worry about it. It hurts too much to go on for long, I didn’t expect you last too long either.”
“Is it ok to cum inside you?”
“Yeah, I’m on the pill.”
“Yeah, mom took me to the doctor and she gave it to me to regulate my period.”
At the news I couldn’t hold it any longer. My cock started spewing jet after jet of cum. It was the longest and hardest cum I’ve ever had in my life.
As I came, Jenny settled down and took my whole cock into her clamping pussy and sat down low on my crotch.
I never got soft.
“This is starting to feel good.”
“But I’m not moving inside you.”
“I know, but the pain is going away, there is only some pressure and it feels good. How come you’re still hard?”
“I don’t know. I usually go soft after I cum, but I guess your tight pussy is keeping me hard. I’ve never been in a pussy before.”
“I never had anything bigger than a tampon in their before either. But this feels so good now. At first it was painful, but the pain is now mostly gone.”
I pushed my ass lower and withdrew my cock a couple of inches from Jenny’s pussy.
“Oohh.” She moaned.
I pushed back up returning my cock to the pervious position to the beautiful sound of another moan from Jenny.
That small motion started our first actual fuck. I was way sensitive and the friction of her pussy on my cock was a bit much, but after couple of dozen thrusts things went back to feeling good.
As we fucked, Jenny got wetter and wetter. The friction became less and the feeling inside her wetness felt more unbelievable.
“Play with my clit!”
Jenny leaned back while still moving slowly up and down on my cock and grabbed my right hand and brought it between us.
“Use your thumb on this spot.” She instructed as she aimed my thumb.
“Feel the small bump here?”
“Massage it lightly as I move.”
I started moving my thumb in circles around the little nub and within thirty seconds Jenny leaned over me and bit my shoulder. It hurt like a motherfucker.
“Hey, what the hell, that hurts!” Burst as I pushed her back.
“Sorry. Sorry! I couldn’t help myself. I almost screamed as I came. I didn’t want mom and dad to hear and your the closest thing.”
I had been close to coming and the pain in my shoulder pushed my orgasm away.
“You came?” I asked amazed. This was the first time a girl orgasms riding my cock. It made me feel good; proud even.
“Yeah, I did. Didn’t you feel it?”
“I felt the pain in my shoulder.”
“Ok, sis. Now that you came, I want to change.”
“Position.” I said as I wrapped my arm around her back and stood up supporting Jenny with my arms and my embedded cock.
“Ohh. You’re so deep now.”
“Feels good. Good for you?”
“Well, not much, you’re bumping into my cervix hard and that hurts a bit.”
I turned and put Jenny on her back on the sofa and laid over her.
I pulled up and looked down on her. She was beautiful. I pushed her half shirt up over her tits and feasted my eyes on those perfect orbs.
“You like ‘em?”
“Hell yeah! I haven’t seen any better looking tits in my life.”
“Have you seen tits?”
“Well, in magazines.” I said as I pulled out a bit and shoved my cock back in.
I started a slow in and out motion pulling my cock almost all the way out to maximize the friction and pushing back in.
I’ve always understood that sex is better than masturbation by this was more than I ever expected. It felt like I was surrounded by a wet hot glove that contoured my cock perfectly maximizing the contact and the friction to perfection. I couldn’t ask for more than this.
I looked up into my sister’s gorgeous green eyes. She licked her lips and then caught the lower one between her white teeth. My hands moved. I cupped her firm tits, squeezing as I felt her crinkled nipples pressing into my sweaty palms.
“Kiss my titties,” Jenny groaned in a gurgling whisper.
I bent and caught one of my sister’s erect brown nipples, sucking at it. I pushed both globes together against my face, switching back and forth between boobs, nibbling at her nipples with my lips.
“Bite ‘em,” she panted.
I didn’t want to hurt my sister, but I did as she begged. I pulled out on one rubbery nipple, stretching the crinkled bud until it snapped through my lightly gripping teeth. I caught it again, sucking in deep as I worked my teeth over the stiff flesh. My tongue wobbled back and forth over just the tip of her sensitive nipple.
“I’m gonna come, Jake,” she whimpered. “Yes, baby. Ooooh, that’s it! God, I’m gonna come so good!”
Jenny pushed my face away, grinding her hips against my crotch. I squeezed, rolling the rubbery buds of her nipples between my fingers and thumbs. Jenny went into a spasms that tightened her body, her cunt rippling up inside. She held my throbbing cock in that liquid velvet trap between her churning legs, raising and lowering herself fucking herself on my cock from below. The sensations as she fucked me were overwhelming.
Jenny’s orgasm washed over her. That did it. I fought back a groan as I shoved my cock as far inside my sister as I could get it. My cock shook as cum blasted deep inside her body.
Jenny and I got a lot of use out of that basement all through the next couple of years.
Jenny loved it when I ate her to orgasm the first time and I loved it when she reciprocated soon after and swallowed my cum without hesitation.
We even experimented with anal sex and Jenny loved the occasional cock up her ass, it made her orgasm like crazy as she impaled her ass on my cock with her back towards and I wrapped my arms around her front and buried my middle and ring fingers inside her cunt and fucked both holes.
Jenny just loves sex, and she doesn’t care where I put my cock, as long as I put in her!
Early on, we both discovered that we never wanted to live apart. After high school, we went to the same university and rented an apartment on the pretence of saving money.
It’s been six years since that first fuck and we still fuck like bunnies every day. We can’t get enough of each other.
Life is good with Jenny.