The Usual Disclaimer: This is a work of fantasy. All characters featured in sexual situations are over 18. The characters in these stories are fictional. Any resemblance to actual persons living, dead or undead is purely coincidental. Do not try this at home.
I sat down and jotted the first scene I had in mind for this story, and immediately became concerned. It just felt too much like I was "ripping off" desurtdawg's marvelous story,
My Sister Eva Started it All
. I sent him an e-mail voicing my concerns, but did not hear back from him. I let the rest of the story take shape in my mind over the following day, and realized that the story I had in mind didn't really have anything else in common with his Literotica classic, other than that one scene.
Still, I would be remiss if I did not recognize how his story inspired mine. I hope you are well, sir.
* * * * *
My name is Robert, but I was always "Bobby" growing up. Our dad was "Big Bob" so I suppose it could have been a lot worse; I could have been "Bob junior" or "Little Bob" or something like that. Dad was an offensive lineman in high school and college, so the name fit. I've seen pictures of him from back then; he was an imposing figure. He's still tall and very strong, but he has slimmed down a lot since his playing days. Our mother is more than a foot shorter than me and Dad, but both of them keep in really great shape.
My older sister is named Karen, and we have always been fairly close. She is two years older than me, but she is rather petite like our mother is. I was taller than her once I reached junior high, and I was always protective of her. She never seemed to mind. Despite my taller stature, I have always looked up to my sister. She was always there to offer me advice if I asked, and she occasionally let me know when I was doing something particularly stupid without being mean about it.
It's not like we were a particularly "touchy-feely" family, but our parents gave us hugs pretty regularly, I was comfortable hugging my sister, and she enjoyed it when we sat on the couch and I reached over to scratch her back for her. I wasn't as keen to have her scratch my back—I was too ticklish to enjoy it.
We grew up in a fairly small Midwestern town. Both of our parents worked, but they were home almost every evening. Our folks raised us to be respectful members of the community. We went to church every Sunday, I was a Boy Scout, I played football and baseball for our school, and I dated in high school. There was nothing about my life that really stood out—at least to me. I considered my life completely normal...except for one little thing.
I was obsessed with anal sex.
I can trace the origin of my fixation easily enough. My senior year of high school our old computer died and I needed a new one for my school work. Karen was already away at college and both of our parents were busy at the time. During their weekly phone call, they mentioned the computer to my sister and she recommended the laptop she had purchased for her college classes. Karen sent them a link, and my mom made the purchase online. They had me pick up the laptop from the store the following evening.
No big deal, right? Except, for once, I had my computer before my parents could lay hands on it. Our old computer had draconic parental controls installed. They had installed those when I was twelve. There had never been porn in our house, and that had been the case for so long that it completely escaped my parents' attention that they had not bothered to put those same parental controls into place on my new laptop.
I had porn!!
However, I was so busy with school at the time that I didn't think about it for two weeks. I was dating a girl named Betty at the time, and we were in the middle of our football season. Betty and I got together and made out a few times, but never had enough time or privacy to actually have sex like we wanted to. She was gorgeous, with curly black hair and an incredibly stacked, petite body. I was lying in my bed late one night, idly stroking my hard dick and thinking about Betty's fantastic tits, when it suddenly hit me.
I had porn!!
I sat bolt upright in my bed and my body shook with excitement when I stealthily locked my bedroom door and opened my laptop computer on my desk. Sure enough, I had unfettered access to all the porn the internet had to offer. I jacked off seven times that night, watching a smorgasbord of varied sex acts.
That was the first time I saw anal sex. I'd never even thought about it before that night, honestly. After I watched that first clip, I stared at the screen with my mouth hanging open. I don't know why it turned me on so much, but it made me harder than I had ever been before. Naturally enough, that video had dozens more linked to it that featured sexy women taking hard cocks in their asses.
I watched two straight hours of anal sex clips and jacked off three more times before I realized how long I had been at it. Then I shut down my laptop and retreated back to bed on shaking legs. I lay awake for another hour feeling like my head was spinning as a montage of butt-fucking clips played in my mind.
In the morning, I awoke with my usual morning erection, but I found myself thinking about sticking that hard dick into some woman's wet, welcoming asshole. At the time, it bothered me. I had enjoyed the pleasure of having sex with girls I dated in high school, and had never once even considered putting my dick in a girl's ass. The way I had been raised, it felt like there was something
wrong
about doing something like that; like it was just perverted and dirty.
After that first night, I watched a lot more internet porn. I might go two or three days without looking at anal sex clips, but invariably found myself drawn back to watching more of them. Those always got me harder than anything else I watched, and got me off quicker as well. By the time Betty and I finally got to spend an afternoon together while my parents were still at work, I found myself staring at her sexy ass as she stripped in my bedroom.
The thing was, Betty had really nice, big tits—especially for an 18-year-old high school girl. Up until I started watching all those anal sex clips, I had practically drooled at the thought of seeing, fondling, and sucking Betty's incredible tits. When I finally got to see them in all their naked glory, I really wanted to flip her back over onto her knees so I could feast my eyes on her asshole while I fucked her.
That didn't happen, and I really did enjoy sucking her hard nipples and squeezing her breasts while we fucked on my bed. Her wet, tight pussy felt sensational, and I came hard inside her after she told me it was okay. It was incredible, really. But...damn, I wanted to play with her ass.
