Jake's Step-Sister Slave

Jake woke up with his head screaming at him. He sat up, maybe a little too quickly, causing more pain to flow to his head. He returned his tender head to the pillow, only to realize that even resting on the soft pillow was causing him pain. Sighing, he extracted himself from the comfort of his bed. Having just completed his first year at college, Jake was home for summer break. This had been his first reunion with his high school friends and they had celebrated pretty hard. They had been at Matt's house, down the street, but Jake couldn't actually remember getting home. He hoped none of his neighbors witnessed what must have been a very unsteady walk down the block.

He remembered the rest of the night, and it had been great. Never one for the big parties, Jake had spent the night with Matt and Justin, his two closest friends from high school. Matt's older brother had gotten them a handle of rum, since they were all either 19 or 20, not able to buy their own alcohol yet. As far as he could remember, they had all but finished the whole bottle off. It was just the three of them all night, but they had spent it catching up with each other; reminiscing about high school, talking about their respective classes (all three were in college), and telling stories from their first semesters. Of course, many of the stories involved drinking and sexual conquests. Matt had apparently turned into somewhat of a ladies man, and consequently he had the most stories. Jake was able to contribute a few of his own while Justin had to admit that he was still a virgin, though was proud that he had gotten his first blow job.

Jake also remembered leaving for the night. His mom and step-dad were both out for the night at a corporate party of some sort, leaving just Jake and his step-sister Cassandra. She was a year older than Jake and so was home from her second year of college. While Jake was in a state school, Cassandra was attending a fancy private school across the country. Their parents had married when Jake was a sophomore in high school. Like college, Jake had been in the public school while Cassandra attended the local private, all-girls school, St. Mary's. Not wanting to tear either away from their friends, the parents decided to just leave them in the schools they already attended. Jake and Cass had never really come together as siblings during that time, and now they almost never even talked since they were both away at college. She had jeered him for going to Matt's house last night, calling it immature. But Jake knew that she was just jealous since she was stuck at home all night. She didn't have the same solid group of friends to come back home to; her summer was likely going to be long and boring.

Having never gotten close during high school, Jake didn't know many of her friends. The general assumption was that girls from St. Mary's were snobby and somewhat slutty. Jake had certainly found the snobby part to be true in Cassandra, but not the slutty part. In fact, he had never even seen her with a guy, though not because of her looks. She was 5'7" with strawberry blond hair. Her face was very symmetrical with eyes that just showed a touch of her Asian heritage, from somewhere far back on her mother's family line. That heritage was also shown in her smooth, flawless skin. She had a very fit body that didn't seem to require a lot of upkeep; Jake rarely saw her do more than take an occasional jog and she had never been on any sports teams. Her breasts were probably a C cup, and her torso tapered to a slim waist. A nearly perfect butt finished off the hour-glass figure.

Having an attractive step-sister had been much cause of merriment for Jake's friends, who constantly teased him about it. Jake knew that they were all attracted to her, and he was as well on some levels. Living with her, it was difficult not to notice how beautiful she was. She often wore very tight clothing that accentuated her curves. He had seen her in bikinis as she lay out by their pool as well as her sleeping gear, consisting of just boxer shorts and a tee shirt; her perky breasts supporting themselves under the thin material. He had tried fantasizing about her on a couple occasions, but had never really been able to follow through with it. She wasn't his real sister, and he wasn't even that close to her. But it was still just a little weird. Besides, he could never separate that personality from the body in his mind.

Though only living together for two years of high school before she went off to college, they had known each other for a while longer since their parents had dated for about 3 years before getting married. In that time, Cass had always been somewhat mean to him, despite the fact that he had tried to be nice to her when they first met. He had quickly decided to stop trying. She was always treating him with distain, clearly thinking herself, with her private school education, superior to Jake and his public school experience. She also seemed to resent having to share her father, his house and his money with Jake and his mom.

Jake dragged himself painfully across his room to his computer desk and plopped down. Comparing two half empty water bottles, he chose the one that looked a little fresher and took a couple of large swigs, briefly washing the hangover taste out of his mouth. He reached down and powered on his computer. His parents had bought him a new system for college, and this one was much slower, even in powering up. He couldn't explain it, but whenever he was hung over, the only thing Jake wanted to do was look at porn and jerk off. He had never deeply analyzed this odd habit, but figured it just helped him take his mind off his aching body long enough for it to start healing. Kind of like in high school when he had simply slept through his hang overs.

Over the years, he had grown bored with the traditional porn sites. They mostly featured either petite, small chested girls going for the little girl look or busty porn stars that always reminded him of those cheap Asian cars that had way too many modifications made. And they always seemed to have looks either bordering on anger or of extreme surprise on their faces while they got pounded by some sleazy looking guy (or two). He still would look at that kind of porn occasionally, and had a few key stars that he particularly liked, but had gravitated to a new site that he had found a few months back. It was an amateur site, but not the kind that featured women who thought they could be porn stars posting pictures. This was a forum in which people would post pictures and videos that they had "found" (usually by questionable means) online. It was totally free, well moderated to keep real porn, external links, and questionable stuff off the site (anything featuring girls who looked too young, animals, pros, or peeing would be promptly removed). Jake could usually count on around 50 new posts a day, much better than most porn sites. The quality of the posts varied; there would always be some heftier ladies, some past their prime, or otherwise not interesting to Jake. But he also found some of the sexiest women that he had ever seen on that site...and they were all real! Many of the pictures came from online hookup sites, where people post the pictures themselves, but some came from hackers breaking into people's computers to find their personal pictures.

So Jake logged in and prepared for what was likely going to be a long morning of self-pleasuring. He pulled up the list of the most recent posts and started at the top. He skipped the first post, which was simply title "BBW". The second one was more promising and featured a young couple on vacation. The girl was quite pretty and there were even a couple of hardcore pictures. He sifted through them, selecting his favorite to save for later. The next post had a video titled "Macy loves to give head", and the description promised a lovely young girl would couldn't get enough cock. Usually the posts had little to no text in them, until you get to people's comments below. But sometimes the author of the post felt it necessary to provide some color to it; sometimes describing how they felt about it or how they came upon the pictures. As he waited for the video to load, he lamented not being on his school computer, which would have had the video loaded long ago. As he waited, he went back to the picture he had saved earlier. Finally, the video was loaded and he was able to watch a shaky, poor quality shot of a redhead seemingly desperate to please the guy holding the camera. After a few minutes, he came on her face, which often happened in these videos. It seemed that girls who allowed themselves to be videotaped giving a blow job would generally allow facials as well.

Half an hour in and about 8 posts down, Jake came upon one that looked really promising. The title was "Amazing College Chick HUGE Find: HD". Jake could see that it had been posted earlier that morning, yet already received quite a few views and comments. The community rating was epically high as well. Excited, he opened the post that he figured would finish off his session. This one had an unusually long description, consisting of two paragraphs that pushed the posted pictures below the fold, out of site.

I work at a university on the East Coast (which will not be named for obvious reasons). I'm in IT support and generally help spoiled college kids get all the viruses off their computers from going to the wrong sites without the proper security installed. It's usually a pretty boring job, consisting of installing malware software that finds the viruses and clears them out. But a couple weeks ago, this one idiot brought his comp in complaining that it was running slow. I got a little info from him and took his computer, promising to fix it and get it back to him the next day. It turns out the problem was the 2 GB of pics he had, all of this one chick, presumably his GF. This girl is HOT and pretty much does everything! It took me all night to download the pictures off his computer, and I returned it to him in the morning. Most of the pics are naked, with a lot of hardcore stuff sprinkled in there as well. I suggested that he get an external drive to store the pictures.

Anyway, I'm just getting around to posting these since it took me a while to, uh, *assess* them. This is an epic post that is going to require multiple postings to get them all up here. I started this post with all the non-nude, everyday pictures of this chick, so you can "get to know her" a little (she has some hot friends as well), the naked pics will start showing up in the next post. My schedule is pretty demanding, so it is likely I'll only be able to do one a week, but don't worry, it's totally worth it! Check back often to get the latest installment of the sexual adventures of this babe! Enjoy!

Although it took a lot of will power sometimes, Jake always forced himself to read any description. He figured that he owed it to the people who took the time to provide him with porn and found that it sometimes enhanced the experience if he knew a little bit of a back story, though any personal information about the people in the pictures was always promptly removed by the moderators. Disappointed that it didn't sound like there would be any naked pictures just yet, he figured he would skim through the non-nudes to prepare for whenever the naked ones were posted. He scrolled down to find about 50 thumbnails in the post. The first few had multiple people in it, so he couldn't see many details. He opened the first thumbnail to find 5 college looking girls. While it was a large picture, obviously taken in the highest resolution setting on a quality camera, it was a little blurry. Jake could tell that all the girls were scantily dressed outside and had good figures; probably on their way to some party. He moved on to the next thumbnail, which was a similar picture but in focus this time. Jake stopped; his mouth fell open.

There was no denying that the second girl on the left was his step-sister. He didn't know what to do and just stared at the picture for a couple of minutes. In his short time on this site, he had known that there was a possibility that he would see someone he knew. In fact, that idea excited him a little. But he had never imagined it would be Cassandra. Well, at least she's not the main girl in this post, he thought a little hopefully. But the next five pictures were all of her. It was pretty clear that she was the "amazing college chick". He couldn't help himself and opened each thumbnail. Most of the pictures seemed to be from one party, to which she had worn a short top that showed off her thin waist and a short skirt that showed off her toned legs. Halfway through the post, the setting of the pictures changed to the beach, with a couple of her friends. The author was right, her friends were quite hot. Cass was lying on the beach in her bikini, smiling sarcastically at the camera in one picture, flipping the bird in the next, lying back with her eyes closed, and so on. It was at this point that Jake realized that his dick was still hard and he was still stroking it. He was jerking off to his step-sister.

The idea didn't disgust him as much as amaze him. He had tried a couple times and never been able to successfully do it. But having pictures in front of him was a different story. And the promise of naked, even hardcore, pictures of her were going to be posted helped. He continued through the pictures, particularly liking the beach shots where the three girls ventured into the water and returned with noticeably hard nipples. Despite the fact that there was no nudity and he had saved some good pictures from other posts, he completed his masturbatory session using just those pictures, the final one being a shot of Cass doing her make up in just her underwear, her toned ass framed nicely by a red thong.

--

Jake found that he looked at Cass in a very different light then he had before, and he even attempted to be a little friendlier toward her. If she noticed, she only responded by being more distant and haughty to him. Her attitude was easier to cope with now, and Jake often found himself smiling when she would make a snarky remark to him, wondering if she was sporting her red thong. He couldn't stop thinking about the pictures, which he had saved to his computer. Left to his own overactive imagination, he visualized the rest of the collection in his mind, placing Cassandra into various sexual situations. As if a barrier had been crossed, he suddenly found himself able to fantasize about his sexy step-sister.

He returned to the forum daily, constantly checking the post of Cass. The comments continued to grow, but there were no new pictures. Most of the comments were either commending the author for the find or expressing excitement for the pictures to come. Jake would generally find other posts to occupy his time, but would always include the saved pictures of Cass in his porn mix, often ending with the underwear pic.

As Cassandra continued to act aloof toward him, Jake realized that he now held something over her. Of course she didn't know that he had these pictures, and likely didn't know that they were online at all, but he guessed she wouldn't be pleased to know that they were out them or that he had them stored securely away on his computer. While he wasn't exactly thinking blackmail, he knew that he could at least get her demeanor toward him to change. Things could get interesting.

--

The following Friday, Jake went out with his friends again. This time, there was a garage party a few blogs away. Someone had managed to product a keg of very cheap beer. It tasted horrible, but that didn't stop Jake from drinking more than he should have. Of course, he woke up the next morning hung over once again. Although a beer hangover was different than a liquor hangover, his cure was the same. It took a while, but he extracted himself from his bed and delicately conveyed his aching head over to his computer. He briefly considered going to the bathroom to make himself throw up, but the thought was exhausting. As usual, he logged into the porn forum, and opened up the latest posts list. Out of habit, he checked the "Amazing College Chick" post. He had to look twice in case his blurry hangover vision was deceiving him. Yup, there was the little icon next to the post link indicating new pictures had been added to the post. His heart skipped a beat, any thoughts of his hangover long gone. The fact that he immediately got hard didn't escape his attention.

Trying to take his time and savor the moment, he slowly clicked on the link. Up popped the post, starting with the original pictures first. He then scrolled down through all the comments and clicked to go to the next page. There were yet more comments and finally he found the latest post from the author. Keeping the thumbnails below the fold so as to not ruin the surprise, Jake read the author's comments on this next batch of pictures:

Wow, glad to see you pervs liked this so much! Thanks for all the love! As promised, here is the next batch of pictures. This little minx gives us a little taste of her wild side...and gets a little taste herself!  Stay tuned, they only get better.

His hands were shaking, and Jake wasn't sure if it was due to his extreme dehydration and hangover or his excitement. He slowly moved the scroll wheel on his mouse down, bringing the thumbnails into view. He was greeted by another batch of about 50 small pictures. Though they were small, he could see that the first picture had her sitting on a bed in lingerie. He opened it up to see the details and was rewarded with a large, clear picture of Cassandra in a see through teddy sitting on a bed in what appeared to be her dorm room. Lying next to her was a medium sized, standardly shaped dildo. Jake could see her dark nipples outlined through the lace. He savored that picture for a moment before moving on, knowing they would get better. He wasn't disappointed. The pictures that followed tracked her as she picked up the dildo, moistened it in her mouth, and pleasured herself with it.

The first picture that gave Jake a clear shot of his step-sisters pussy stayed enlarged on his screen for a long while as he studied it. A week ago, it would have been unthinkable for him to stare at a picture of Cassandra's most private parts, let alone pleasure himself to it. But after breaking the dam holding back all his fantasies of her and seeing her in his imagination all week, there was nothing he wanted more. She was totally shaved in the picture making every detail of her parted, red lips visible. Her clit was much engorged and her inner lips were just making themselves visible in her aroused state. Jake eagerly clicked through the pictures as she gently slid the dildo in and out. He imagined the sounds she would be making. Part way through, she pulled her lace teddy down exposing her tits to Jake for the first time. She had medium to small dark nipples, somewhere between the sizes of a quarter and a half dollar. It was very perky, seemingly holding itself up. Essentially, they were just as Jake had imagined the breasts that hid behind the thin material of her sleeping shirts.

About 30 pictures detailed Cass's dildo experience; showing her in different positions on the bed, different facial expressions on her face, using the tool in different ways (Jake's favorite was when she licked the slick juices off of it). It was hard for Jeff to mix this wild, naughty coed with the cold, private school girl that he knew was downstairs at the moment. But from the thumbnail previews, he knew it was going to get dirtier. The last portion of the pictures showed Cass blowing the photographer, while still keeping the dildo firmly planted inside her. Jake was amazed when he pulled up a picture that showed the penis almost completely inside her mouth. In his limited experience with girls in the past year, Jake had never seen more than half of his dick inside a mouth, though he was a little bigger than the one in the picture. He made it to the end of the thumbnails with a picture that showed Cassandra sitting up on the bed, looking very content with both tits still exposed. A small trickle of seaman was escaping from the corner of her mouth. That was all Jake needed to push himself over the edge.