Katie’s Russian Roulette Challenge… [Mff inc preg drugs]

This is the fourth part in a series about Michael and his sister Katie. Check my submission history for the prior three. Each story can be read independently without the knowledge of the prior stories.

Even I had to take some time to think about the wild shit that Katie proposed to Tara and I on the day that Katie shared our secret. After all, I was the adult in the situation being five years their senior and went through the crushing experience of adulthood that, although they were 19, they really did not understand. I knew all too well the repercussions of chasing greater and greater highs as it was the story of my college experience. But even I couldn't take my mind off of Katie's proposal.

Logically, it was a simple answer – no. No we shouldn't do it because, well, we had every reason not to. But there was one good reason to do it – the risk. The idea of playing with fire and not getting burned causes a euphoric high that only draws you to do it again.

My sister’s best friend…. [Mff, oral, drugs, inc]

This is Part 3 of a series regarding Michael and his sister Katie

Katie and I became close in the weeks following the day she caught me masturbating to her in the shower. She sucked me off and since then we both seemed to get off sneaking into each others rooms while our parents were asleep – something we never did as kids – but now my 19 year old sister and I couldn't stop giving each other oral sex. She would sneak into my room late and night and just wrap her legs around my head and then she would go down on me ferociously while they were at work. We also decided to dip into her little box of party tricks, usually just smoking a joint but there were times we did a little more.

Like the time I came home from work and found Katie and her friend Tara getting high in her room. I joined in mostly interested in Tara who I remember from before I moved away. Even 5 years later they were still doing everything together and Tara had gotten very hot. She was shorter than Katie and blond. While Katie was thinner and more toned than Tara, Tara looked good with her added weight. It gave her body a feminine softness that Katie didn't quite possess and was looking particularly appealing to me that afternoon.

While watching my sister shower… [Mf, inc, voy, reluc, oral]

This is part 2 in my dark minds, dark places series. This can be read independently or in conjunction with part 1 – When I Came Home From College (see posting history)

For several weeks I had been watching my sister Katie shower in the bathroom without her realizing it. I got off on it in a way that nothing else had ever turned me on. I was 25 and with her being six years my junior it made it all the more hot. It usually started once I heard the door lock. I immediately would rush downstairs into the basement, climb up the footstool, push out the floorboard in the bathroom closet, and climb silently through. Once inside I watched her through the slats of the closet door as she showered with my dick solid in my hand stroking silently to her hygiene ritual.

When I came home from college… [Mf, voy, inc]

This is the first in a line of stories that will be connected but each will be able to be read independently. They will focus on what most would consider seriously inappropriate taboos with this story being the most vanilla of them all. If these sort of things are your fetish, please sit back and enjoy…

It all started when I came home after graduating from college at 25. Graduating with an MBA, as I soon learned, does not automatically translate into finding a good paying job. When I went off to college after high school I had big plans – I picked the college farthest away from my parents because I was ready to be independent. The first couple years parties, sex, drugs, and drinking took up a majority of my time and, as you can imagine, piece by piece my four year college education plan was extended. Failing classes, signing up for fewer classes than I could have handled, not taking anything truly seriously significantly put me behind. At first it didn't matter because I had a money flow from my parents that would keep coming in but as they started learning about my grades that money slowed to a trickle. Year by year the realities of adulthood hit me – I had to start working a job on the side, taking on deeper and deeper debt, and actually taking my classes more seriously. But when I did finally graduate I realized I had no serious job opportunities. Saddled with debt I had to go home, back to the small town my parents lived in, and admit defeat.

Fucking the girl of my dreams.

It was late on a Friday night when i texted her. Sitting alone in my room with the light off and an empty bottle of wine next to me.

"Hey do you want to come over for some cuddles and maybe a movie?"

My heart raced as it took her time to respond. This was the second time that i had made a pass at her, but the first time that i had ever done it sober*. The last time that we crossed paths was at a friends pool party. I showed up and swam and smoked a bit with some friends. Everyone at the party had a pretty good buzz going on.

Those of us who were closest to the party thrower stayed latest. Too drunk to drive, he insisted that we stay over. As i lay falling asleep on his couch, i looked across the room and saw her lying there, twiddling her thumbs.

"H-hey… you still u-up?," i hiccuped and slurred. She looked over at me, almost surprised, "Yeah," she quietly muttered.

Massaging my partners nonidentical twin-sister into oblivion. [m>f]

A little back story. Partner comes from a home where the women are extremely open. Yes they talk about sex and dildos and all kinds of weird things with each other and their own mother. They also go family skinny dipping. Back story on the twin. They are not identical, but are extremely close and competitive. They are quite "revealing". Will sunbake topless at beach. My partner only at secluded ones with less people to bump into. Her sister does it anywhere. Even at home by the pool. She also likes to show off her ass with a thong. That's a thing. I had seen her naked before this point. She walks out of the shower with a towel, sometimes she forgets it. I am positive she does it on purpose… who knows. Plenty of stories. She is really comfortable in her own body and she is hot too, which helps. (I wrote this bit after)

Breaking in a pornstar – Part 5 [Mdom][Fsub][inc][str8]

Gisele woke up in a warm, cozy bed. It felt like she had been asleep for days. At first her arousal made it hard to relax, but her Masters comforting presence made her forget all about it. She turned to her right to embrace him. But he wasn't there. She sat up and looked around, but found evidence of his existance. Gisele got out of bed, put on a pair of pink panties and opened the bedroom door. She walked down the stairs into the hall, still no sign of her Master.

The preparations for the day were complete, all he had to do was to wait for Gisele to wake up. John took a sip of coffee before looking at his wristwatch. Ten to nine, still early. He took another sip of coffee. Suddenly he could hear the sound of light steps against floorboards coming from the stairs. A final sip of coffee left the mug empty. Perfect timing.

[Str8, MF, voy, nc, reluc, inc, mast, timestop, oral] Jake’s Magic Remote, Part V – Cruel Temptations

Let's keep it rolling! Part V is a light interlude, but it sets some things up. As always, feedback is welcome! I've been working on part XI today, it's pretty fun.

Sarah showed up while Petra was cleaning up, so Jake decided to let things rest for a bit; he’d had his fun, and he was more than a little worried in hindsight about how readily he’d molested his daughter just because she was wearing tiny shorts and he was uncomfortably horny.
Then again, he thought to himself, she was sort of asking for it. It was obvious that Petra had a mild exhibitionism or voyeurism fetish developing, and all he’d really done was fulfil her own fantasy for her, so why should he feel bad?
Petra changed into pajama pants and the three watched the rest of the movie together. Once again, Jake got to enjoy having his favorite two females on either side of him. As evenings go, it was pretty nice, and he’d soon put his daughter’s rampant sexuality out of his mind.

[Str8, MF, voy, nc, reluc, inc, mast, timestop] Jake’s Magic Remote, Part IV – Home Movies

Jake’s mind was racing as he went through the motions of working. He’d stopped time without the remote! Was it him that did it? Was it a safety feature? And why did he keep getting in near-misses with cars?
Speaking of cars, around lunchtime he realized he’d never called Carol to let her know he was okay. Granted he thought he saw her in the food court when he was messing with those girls, but she was gone so fast he couldn’t be sure. He reached into his bag to find the card she’d left in there and dialed the number on it, putting on his phone headset.
While the phone rang, Jake took the opportunity to discreetly move the panty collection from his bag to a locked drawer in his desk. Carol’s voice came across the line after a few rings. “How are you, Jake?”
“I’m great,” Jake replied, closing and locking the drawer. “My head’s much better. Sorry I didn’t call sooner.”
“That’s alright,” she replied. “You’ve been very busy. We’ll catch up later this week.”
Jake was about to respond when the line went dead. “Huh,” he said to himself. He was starting to wonder if the appearance of the remote in his bag was really an accident.
He might have followed that train of thought further, but something drilled into his brain at that exact moment. Specifically, Marta’s shrill, too-loud laugh, coming from the Deskside guys’ office across the hall. He scowled in irritation. She was at it again, showing off her fake tits so she would never have to remember her password.
Jake slapped his pause button. He still hadn’t figured out how he’d stopped the car, but the remote still worked just fine. He got up from his desk and stalked angrily over to the Deskside office.
It was quite a tableau in there. The guys all had big desk surfaces to work on, more like tables really. Tim, the new guy, was taking a phone call and clearly annoyed at the noise level. A couple of the other guys were standing, clearly chatting with Marta, who herself was in the middle of saying something. One other tech was bent over an open computer, but his eyeline was pretty obviously pointing at the infamous tits.
Being Friday, everyone was in casual wear in the office. Marta was wearing another v-neck today, this one a tight-fitting white tee. Underneath he could just make out the outline of her bra. Under that she had a black skirt that ended well above the knee. She was apparently pushing “business casual” to new limits.
Jake went to work immediately. First he pulled off Marta’s top and put it aside. “Won’t be needing this,” he said to nobody. He snatched a sharpie off the Tim’s desk and went about leaving his calling card. Across her back was the usual “I AM A BITCH”, and then below he wrote “I use my fake tits and pushy attitude to manipulate the socially inept.” Part of him wished he could see the look on her face when whoever she was fucking found that on her.
Next he flipped up her skirt and confiscated the lacy black thong she wore, shoving it in his pocket. He did have to admit, she had a really nice ass. Probably did a lot of squats to keep it that way. He squeezed it in both hands, smirking at the dual imprints he left behind.
Moving around in front of her, Jake was amused but not surprised to see that Marta’s pussy was shaved bare. His dick jumped in his pants, excited by standing here with so much power over this stupid cunt.
Grinning, Jake pushed Marta down onto her knees on the carpet. He carefully pulled her tongue out of her open mouth, then unzipped and pulled out his cock. It was partly hard already, and he ran it along her tongue, making her lick all over it and getting it a little moist from her saliva. Next he unhooked her front-clasp bra and once again exposed her globelike fake tits.
“Might as well get your money’s worth of these,” Jake quipped as he nestled his cock between them. He put his hands on either side and pressed inward, creating a warm fleshy tunnel around his shaft, and started slowly pumping it back and forth.
Marta’s flesh, warm and saliva-moist, felt simply wonderful around Jake’s dick. He moaned aloud, looking down at her, then laughed as he realized she still had her tongue sticking out of her open mouth. “Well that’s distracting,” he said, shoving it back in there and closing her lips and jaw. Once again he carefully nudged her lips into a smile. “Much better,” he said, resuming the slow stroking in her cleavage. “You should be happy that you’re being used for your intended purpose.”
Jake moved his thumbs to play with Marta’s nipples and started fucking her tits harder and faster, grinning down at her frozen smile. “What a pretty look for you. I know… just the thing to complete it!” As he spoke, he started shooting cum between her tits and up her neck to her chin. He pulled back and stroked himself, finishing the load with a last shot across her face. From this close, the cum had enough time to splatter on Marta’s skin and hair before freezing with her.
Jake squeezed the last few drops out onto Marta’s lips and took a step back to appreciate his work.
It was quite a scene. Marta knelt in the office, surrounded by smiling I.T. guys, with cum plastered across her face and chest. Her skirt was pulled up and her bra hung open as if she’d been stripped with urgency… which, really, she had been. There was only one thing missing. Jake knelt down and moved Marta’s hands so it looked like she was holding her tits up to receive the load.
“Perfect. Hold it,” Jake said, pulling out his phone to take some photos for posterity – or who knows, he thought, maybe blackmail. “That’s perfect baby, the camera loves you.”
With that done, Jake went about cleaning Marta up… sort of. He used a tissue to scrape all the cum off her skin, then smeared it in a thin coat on her breasts where the bra would be covering them. The bit that had got in her hair he left there, smearing it in until it wasn’t visible. The blob on her lips he pressed onto her tongue and smeared down also, coating its surface.
Next he closed Marta’s bra over his cum and pressed on her tits until they fit into the cups, or at least sort of fit. It was a tight bra, which helped. Finally he stood her up, fixed her skirt, and put her shift back on, carefully moving her hair back into its regular style.
Whistling to himself, Jake returned his office and pressed the Play button.
Marta yelped loudly as she felt the grip on her ass. There was nobody behind her, however, so nobody could be blamed for that. Jake could only imagine how she must be feeling: tits sore and abused, nipples teased, taste of semen in her mouth and a feeling on her skin like someone came on her but no cum to be found.
Jake heard Marta quietly excuse herself and saw her walk out toward her own desk, rubbing her tender chest. He waited a few seconds, then picked up a folder and followed behind her.
“Ow,” Jake heard Marta say quietly as she walked into her own cube. Jake stopped walking and turned to her.
“You alright?” he asked her.
“Yeah, fine,” she replied, sitting down. Her eyes widened dramatically the moment her ass hit the chair, signalling that she’d discovered the theft of her panties. If only she knew they were wadded up in Jake’s pocket right that instant!
“Okeydokey,” Jake replied, turning and walking to the copy room, grinning.
Today was really looking up.