The Jenny File

Both these people are over eighteen.

My brother, Billy, is a couple years older than me. I came to live with him in the city when I started college, and, since then, we've had a fairly standard roommate-type relationship. At least, that's what I thought...

It all happened when I was on his computer. I wanted to put a bunch of songs from his iTunes on my Kindle, and I've often just gone on his computer for things when he's at work or whatever. I was looking for the folder he keeps that stuff in, when I stumbled on one labelled "Jenny"(my name, in case you hadn't guessed). Curious, I opened it, thinking maybe he had pictures of me from various family events.

What I found was about two dozen TXT files, all labelled "Jenny 1" and so on. I clicked on the first one, and it was some kind of short story:

I've just woken up, and I'm walking through the apartment with a cup of coffee, when I find my little sister, Jenny, out on our apartment's balcony, reading a book, wearing this cute little two-piece number, her red hair tied up in a pony tail. I find myself staring at her large, squishy boobies, then moving down to her soft, pudgy belly, then down to her area, and I moan a little. Suddenly, I feel my cock quickly harden, and almost stick out of my boxers. Finally, I just put my cup of coffee down, and go outside.

"Morning, Billy." I don't verbally respond. Instead, I instantly kneel down in front of her. "Uh, Billy?" I then spread her legs, push the crotch of her bathing suit aside, and start licking Jenny's pussy. "Billy..." My little sister starts breathing hard, and moaning, as my tongue probes deeper and deeper into her quickly moistening snatch. Speaking of that, her juices taste really good, so much so, I might just make a thing of eating her out every day. Judging by the sounds she's making, I don't think she'd object. Finally, I start licking and sucking on her throbbing clit and, I can tell by her voice that she's about to cum. When she does, she lets a high-pitched whine, which I'm half afraid might alert people on the street below. I stand up, and Jenny is smiling gratefully at me. I go inside, and get ready for work.

Needless to say, I was a bit confused and upset after reading that. How long had my brother been thinking these things about me? I felt like I wanted to cry or scream. I probably should've just gotten out of there, and drank until I couldn't remember what I'd read, but something compelled me to look at the next one:

Me and my sister, Jenny, are watching TV one night, and quite frankly bored by the lack of anything on. Suddenly, Jenny crawls over to me on the couch. "What are you doing Jenny?" My sister answers by kissing me on the lips. We start making out, and groping at each other. In the midst of this, my sister moves her hand down, and starts rubbing my already hard cock through my pants. Suddenly, she gets down in front of me, and starts undoing my belt. After she gets that open, she unzips my fly with her teeth, and pulls my pants down a little. She then reaches into my boxers, and pulls out my throbbing cock. Smiling up at me, she strokes it, then leans down, and wraps those luscious lips of hers around the shaft. It feels incredible, as she licks and sucks on my swollen head, and strokes the shaft. My sister slowly coaxes me toward orgasm, until I can't hold it in anymore. My cock contracts like it's gonna get a charlie horse, then it lets go. I can hear my little sister rapidly swallowing, getting every drop of my jism as it comes. After teasing my now sensitive cock with her tongue a bit more, she smiles up at me, and I smile back.

As I sat there, reading this, I began to realize I didn't feel sick, but aroused. This was wrong, and my brother was sick, but I couldn't help the way I felt, reading about these fantasies he'd had about me, that he actually felt the need to document.

It was in the next one that he got into actual penetration:

I wake up one morning, and go into the kitchen to make some coffee, and find my Jenny's already there, making breakfast. She's wearing one of her night-shirts, which shows off her shapely form, and she still has a slight case of bed hair, which I actually think looks good on her. Maybe it's because I'm still a little sleepy, but I instantly get hard. "Morning, Billy. Want coffee? I made some." She's naturally surprised as I suddenly bend her over the kitchen counter. "Billy? What are you doing?" She gets her answer, as I lower her panties, then I pull out my throbbing cock, and insert it in her. I can hear her squeal as I fuck her slowly at first, then faster. She's almost screaming by the time I cum about a massive amount inside her. As I pull out, and go to get some coffee, my sister is smiling lasciviously at me, like she wants me to do it again.

How did he know I'm a loud fuck, I wonder? I read a few more, as he described all kinds of acts he wanted to do with me, and I couldn't stop myself from reading one after the other. Until, that is, I got to one that struck me in such a way that, well...just read:

As I approach the bathroom, I can hear Jenny in the shower. I go inside, and my cock gets hard, watching her naked silhouette, soaping herself up. "Hey, Billy. I'll be done soon, than you can use it." I strip down, open the back door, and get in behind her. "Billy? What are you doing?" I come up behind her and start feeling up her large, soapy tits, and kissing behind her ear. My sister almost melts into submission. "Oh, God, Billy...Touch me..." She reaches behind her and starts stroking my hard cock. "Are you gonna fuck me, big brother?"

"Yes." I then bend her over a little, and press the head of my cock against her tight little asshole. My sister groans and squeals as I slowly work my cock in. Jenny's anus grips my cock so tightly, I'm half afraid it might rip it off, but it starts to loosen up slightly. It eventually loosens up enough I'm able to properly fuck her. Her screams echo in our bathroom, as I fuck her asshole hard and fast. Finally, I cum, and her ass is still so tight, that the jizz mostly coats my dick. As I pull out, Jenny turns around, and kisses me. "Thanks," she says, catching her breath.

This is so fucking wrong, and I'm ashamed of myself for this, but I couldn't help it. I reached into my panties, and started masturbating furiously, imagining my brother fucking me in the ass. I eventually came so hard, I actually screamed a little louder than usual, than just tilted my head on his computer screen, catching my breath.

I knew I should just close the folder and leave, and pretend this never happened, but I got an idea. Too good(or bad) of an idea to ignore. Something I knew I would later regret. I opened a new document, and typed out a story where he comes into my room one night, and fucks my brains out. I put in all the things from his stories that had turned me on. Then, I saved it into that folder as "Billy 1", then closed everything out(but not before getting the mp3s I wanted), and left, closing the door behind me.