A Whole Weekend of Revenge

This is the part of a story experiment that I decided I wanted to conduct. I've written a second story with the same beginning, but a decidedly different outcome. Things don't work so well for James in this timeline, but for a timeline where things go better, check out "A Whole Weekend of Passion"! Sequels to come, hopefully!

James stared at his sleeping older sister and her girlfriend in the semidarkness.

Ever since she had come home from college for Christmas two weeks ago, Samantha had been sleeping in the nude. James had seen her at a distance one night when she had forgotten to close her bedroom door and couldn't help but wander inside. He was not disappointed - Sam was apparently a fitful sleeper, and regularly kicked off her blankets to reveal her smooth, slim body and her large, milky tits to the cold midnight air. In that moment, James could not bring himself to care that he was standing over his sister, that the two of them had grown up together and cared about one another as family. All he felt was his hungry, throbbing cock.

He hadn't been able to bring himself to touch Sam, as much as he wanted to grope or fondle or even finger her. But that night and every night since, James pulled out his cock and jacked off over his sister's sleeping body until he brought himself to glorious, spine-curling orgasm. James had shot his load on Samantha's big tits, her firm, athletic stomach, her tight, round ass, her gracefully arching back, her strong, slender legs, and, once, her plump, pink pussy. James figured that she was such a restless sleeper that by morning, the cum had been rubbed into the sheets before it could dry on her skin, and his sister was none the wiser.

And, tonight, Samantha's girlfriend Paige had spent the night. Sam had come out as bi to their mom and dad a year and a half ago, and the family had been understanding and supportive. So, as a show of good faith, James and Samantha's parents had let Paige stay the weekend while they left town to visit an old business friend.

Things could not have been more perfect.

Paige wasn't built the same as Sam. She was shorter, stockier, with bright red hair that contrasted shockingly with Sam's dark brown. However, where Sam was slimmer, Paige was jaw-droppingly voluptuous. Her wide, rounded hips supported a huge, juicy ass, and her breasts were bigger than James's head and turned every shirt that dared attempt to contain them low-cut. James couldn't blame his sister - if he were a girl and Paige had decided to hit on him, he probably would have switched teams entirely.

So, after a languorous hour and a half of listening to his sister and her girlfriend having the loudest, most orgasmic sex he had ever heard, James allowed himself to peek through Sam's door. Page had draped herself over Sam's chest, their magnificent breasts pressed against one another, and the two had fallen asleep in each others' arms sweaty, sticky with each others' cum, and content with the world.

As James crossed the room to the two sleeping women, his erection was so overpowering that he could barely stand - and this was the first night in a whole weekend of sexiness. He stood over his sister and dropped his boxers.

James began to work his cock, pumping his engorged shaft with near desperation. His sister, her girlfriend, their naked skin in the half-light, their delicate curves and the softness of their flesh. It was almost too much for him. Much quicker than usual, James felt tension in his cock, and then finally the bursting release of orgasm.

James's cum shot out onto his sister's stomach, watching the thick gray trail ooze its way down her hipbones to soak the sheets beneath her. But, to his alarm, his cock continued to pump load after load onto his sister - several more wads onto her stomach, three thin streaks across her tits, and, to James's alarm, one ecstatic and venturesome strand across her sleeping face.

James froze, his hand still on his cock. He didn't know if he would be better off running out of the room, or staying as still as he possibly could. Seconds ticked by like hours, and despite the tension, he still couldn't help but admire his sister's cum-covered body, still accompanied by her sleeping, curvy girlfriend.

And then, after an age had passed, Samantha opened her eyes. She ran her tongue across her lips, licking up her brother's cum and smiling slightly. She looked at James and ran a slender, manicured hand from her neck to her supple breasts, gathering James's cum and smearing it across her body in a sticky, glistening sheen. She reached out to James, beckoning with her fingers, and James found himself leaning inward so that she could reach his dick.

Samantha had known all along. Or maybe she had suspected. But there wasn't an ounce of surprise on his sister's face as she played with the cum on her fingertips.

James felt his sister's slim fingers, still warm and slick with his sperm, wrap gently around his cock. The sensation was just as Jim imagined it would be, firm and gentle and close.

***

Then, Samantha's grip tightened, and she pulled hard on James's dick, causing him to stumble forward over the bed. Her expression had changed; she was livid. James gasped in surprise and pain.

"Caught you, you little shit," Sam growled. James heard Paige smacking her lips.

"Ugh," she groaned, "I think he got some in my mouth."

"Are you fucking serious?" Sam shouted. She tightened her grip on James's dick, which refused to go limp.

"Sam, please, that hurts," James whimpered.

"Yeah? You should have thought of that before you decided you wanted to molest me on a nightly basis. And then you had to bring Paige into it!"

"P-please..." The pain and the shame had caused James to tear up.

"Please what? Sorry, James, but you had this one coming."

"What? Sam, please don't tell mom and dad. They'll think I'm a freak."

"You know, I thought about that," Samantha said, swinging her legs over the side of the bed and standing up. She walked around James so that she was behind him, still holding his dick. James was paralyzed, unable to move from out of his sister's grip. "When I started to suspect you were doing something, I thought about letting you off easy, and just asking mom and dad to send you to therapy while I took an acid bath and threw up a couple of times. But you know what? No. You betrayed my trust, you molested me and my girlfriend, and now I'm gonna show you exactly how hurt I feel." Sam leaned closer, and James felt the soft skin of her breasts press against his back. "Paige, get me the Share while I have him here."

Paige smiled and climbed out of the opposite side of the bed, crossing the room to Sam's dresser and turning on a desk lamp. James winced at the harshness of the light.

"Yours or mine?" Paige asked.

"Mine, sweetie. The ribbing on yours is a little too much, I don't want him to bleed all over it."

"Alright, you got it." Paige retrieved a slim black dildo with a curved bulb at its base. By this point, James had nearly lost his mind with terror as the reality had dawned on him that he was going to be raped by his sister. He did not know exactly how, but she was going to violate him to pay him back for all the times he had violated her.

Samantha pushed James face-first onto the bed and bent over him so that they were both still standing and bent over at the waist, Sam's breasts still pressed against his back. "Put it in me, Page."

"You got it. You need any lube?" Page asked.

"Nah, lube'll make it slide out. Just eat me out for a sec and then see if it goes in."

"Alright. Just a second."

Paige walked behind Samantha and dropped to her knees. She grabbed Sam's firm asscheeks and parted them, revealing her girlfriend's plump pink pussylips.

"Yeesh, babe," Paige said, "you're dry as a damn bone."

"Yeah, that's pretty much entirely from pure rage." Sam dug her nails into James's cock and he yelped. "Give me something to be happy about."

Paige pushed her face into Samantha's pussy and began to slurp greedily between her lips. James recoiled as he heard his sister moan into his ear, but felt his cock harden against his will as she pressed her tits so hard into his back he could feel her nipples against his skin as they began to stiffen. Paige pushed her tongue inside Samantha and gave a sigh of her own, causing Sam's insides to buzz. After a minute of the most beautiful groans James had ever heard, Paige withdrew her face from Sam's pussy, a long strand of spit and cum trailing from her lips.

Without a word, Paige grabbed the dildo, took one last look at her girlfriend's long legs and her tight ass, and inserted the bulbed end into Sam's exposed pussy. Sam gave a gasp of pleasure as her body swallowed the fist-sized apparatus with a sucking slurp. When it was in all the way, Sam stood up, spun James around, and pushed him to his knees in front of her. James found himself face-to-face with a black silicone cock protruding from between his sister's legs.

"You like this? It's called the Share. A strapless strap-on. And you're going to get very familiar with it." She grabbed James by his hair and he grunted in protest. "How many times did you shoot your disgusting little wad on me thinking about me sucking your dick, James? How many times did you think about your sister sucking your cock? I want you to think about that long and hard while you're sucking mine, you perverted little shit."

James began to stammer. "Sam, please, I'm sorry, I-"

"Shut up." Samantha forced James's still-open mouth onto her fake cock, pushing its head to the back of his throat. He looked to his right and saw that Paige had retrieved a handheld video camera and had begun to film him.

"You'd better get this nice and wet, James. I don't think you'll be getting any lube this first time around. So put in a bit of extra slobber or you'll be in a world of hurt," Samantha said. She groped her tits with her free hand while she forced James down her shaft, taking a little pleasure in the dildo as it pushed against her clit from James's efforts. Eventually, she let go of James's head and watched as her brother bobbed frantically up and down her shaft in an attempt to wet the dildo with his own saliva. He clutched at her hips, forcing the fake cock inside his mouth as far as it would go and slavering over it so that when his sister raped him it might hurt him less.

"Damn, your little brother's a real cockslut," Paige chuckled, watching and filming. "He treating you well, baby?"

"You bet he is," Sam said, smiling, "but I think now it's time he got the rest of his lesson." Samantha grabbed James by the hair again, pulled him up, spun him around and forced him to bend over her bed again. "You're all mine now," she cooed into his ear, gripping her cock in one hand and James's cock in the other to prevent his escape. Paige moved onto the bed in front of James, aiming the camera and spreading her legs. With her free hand she kneaded one of her massive breasts and waited for the show to start.

James began to blubber, on the verge of tears. "S-Sam... Samantha... Please. Please, I've learned my lesson, I don't want to-"

"Yeah? Did you think about what I wanted when you were jacking off on me? Did you think about what Paige would have wanted?" James heard Sam say behind him. He felt the silicone cock trace the inside of his asscheeks, slick and dripping with his own spit.

"No, I didn't, I'm sorry," James said. This was it. He was going to be raped and humiliated by his sister.

"You're only sorry 'cause you got caught, asshole. So now I'm gonna make your asshole really sorry." Sam pushed the head of her fake cock into James's anus, and his hole quivered and eventually parted for the intruder. James screamed and clutched at Samantha's blankets, and through his tears saw Paige move closer to him.

"That was just the head, you pussy," Sam laughed. "Let's see how you take a real fucking!" Sam grabbed James's hips and began to work into him, and James felt his insides open unto her. The pain was unbearable, but his cock stayed hard. Soon, when James had widened out enough, Sam grabbed James by the hips and began to fuck him. She thrusted into James over and over again, burying the entirety of her dildo in James's ass as he screamed. She slammed her smooth hips against James and watched as her brother's asscheeks bounced from her pounding.

Paige got everything on camera: sister fucking brother, Sam's firm, jiggling tits, James's frantically bouncing cock, the groans from her girlfriend and the screams from James.

"If you want in on this, you can make him eat you out," Sam grunted.

"I was thinking the same thing!" Paige said, scooting in closer on the bed and grabbing James's hair with her free hand. "You got your cum in my mouth, so I might as well return the favor," she giggled into James's pain-contorted face, before pulling him down between her legs. She continued filming as James desperately lapped at her pussy, kissing and licking her vagina to block out the pain of his sister's dick in his ass. Paige purred and released his hair to rake her long fingernails down his back.

"Your brother's so obedient," she breathed, watching as James ate away at her pussy, "I don't even need to hold him down."

"That's because he's a coward, apparently," Sam said as she rammed him, "a pussy that's just waiting to get fucked." She reached around James and grabbed his cock again, pumping it with one hand while she fucked him. As she bent over, Paige reached up and grabbed one of Sam's breasts and began to knead it greedily while James ate her out. With her other hand, Sam reached out and did the same to Paige, hefting one of her deliciously heavy tits and digging her fingers into its soft flesh.

Sam and Paige leaned inward to kiss one another, and for one brief, glorious moment, they were all three joined together - Sam and Paige locked in a passionate kiss and joined at the groin by Samantha's, slobbering, screaming, blubbering brother, forming a human circuit of sex and vengeance.

Paige was the first to break away. "Ooh," she laughed, "I think I felt him moan."

"Think it's about time?" Sam asked.

"Oh yeah. Pull him up for air."

Sam pulled James free of Paige's pussy and he came away gasping and drooling her juices. He was mindless, now, a creature of agony and pleasure, with no will of his own. He no longer cared about his humiliation. All he wanted was to please Paige and his sister until the pain stopped.

As Sam jacked James off with her thin, soft fingers, he felt a familiar twinge in his shaft. A mounting tension, a rising pressure. He looked down at Paige, spread-eagled, fingering her pussy with one hand and masturbating gleefully with the other. If Samantha wasn't careful he was going to cum on-

"Oh, no you don't," Sam whispered into James's ear. She gave one long, powerful thrust inside him, kicking his p-spot into high gear and sending a lightning bolt through his body. James felt the most earth-shattering orgasm of his life building within him, and as Sam jerked him off, he felt the walls crumble and his dick lurched into ecstatic eruption. But Sam's hand moved over the tip, anticipating him, and he exploded into his sister's hand.

James could not help but feel a surge of despair at the loss of such a magnificent load, wasted on just a hand. His dick muscles pushed wad after boiling wad from his shaft with hellish pressure, spattering uselessly against Samantha's palm.

And then, once James was done, Sam pushed her dildo further inside him, and he opened his mouth in one last scream before Sam brought her hand to his mouth, smothering him and nearly drowning him in his own cum. Paige filmed every second as James, penetrated by his own sister, was forced to taste the warm saltiness of his own semen. He was fucked until he swallowed every last drop, and then deposited without ceremony at the foot of the bed.

James woke up, limp-dicked and exhausted, to see Sam and Paige collaborating over him. He was handcuffed to the foot of Sam's bed, his arms suspended above his head to assure his helplessness. Sam shoved a long dildo inside of Paige to see how deep it would go, and Paige responded by playfully shoving a ballgag into Sam's mouth before withdrawing the dildo, wet and drooling, from her pussy.

"So you're not even bothered that he's your brother?" Paige asked, licking her cum off the fake cock and chuckling to herself.

"Not at this point, no," Sam replied, "before, I was too damn mad. Now, I've got a slave. I'm pretty much over that by now. But I'm thinking that between the handcuffs and the blackmail, we can have some fun before mom and dad get back."

The two glanced at James, noticing that he was awake. Sam looked back to Paige. "The way I see it," she said, "this is just the first day in a whole weekend of sexiness."