My Brother's Friends

“So, are we ready?” Keith asked. Anna was fast asleep in her chair. The guys were whispering to each other.

“Yeah. You guys head up to her room. I’ll be up in a second,” Jon said. After his friends had cleared out he leaned over to shake his sister’s shoulder gently. “Anna? Anna, wake up.”

“Mmm?” Anna looked up at him with sleepy eyes and then around the room. “How long have I been asleep?”

“Since about halfway through the movie.”

“I should probably go to bed then, huh?”

“Yeah. Mom will kill me if you don’t get enough sleep.”

“Like mom’ll ever know…”

“In any case, let’s get you up to bed. I’ll walk with you so you don’t fall asleep on the stairs.”

“Mmkay…” Anna stumbled through the door and up the stairs, with Jon by her side supporting her most of the way. She was barely awake when she walked through her bedroom door.

And was greeted by four other males.

“Jon?” she said, turning around, but he was locking the door to prevent her escape. “Jon, what’s going on?”

“Just something the guys planned. They really like you Anna. Even though you hide all the damn time, they like you.”

“I guess that’s good and all, but can they leave? I need to get some sleep.”

“Don’t worry sweetheart. By the time we’re done with you, you’ll be so worn out, you’ll sleep for a week.” Keith’s hand gripped her shoulder and he pulled her back against him. She gasped at the feeling of his erection, pressed against her ass.

“Mike, would you do the honors?” Jon asked.

“Certainly.” Mike produced a switchblade from his back pocket and stepped around to Anna’s front. Without a word he took her shirt and carefully began to slice down the center of it. He repeated the process with her jeans and stepped away to allow the cloth to slide off (with a little assistance from Keith.) Anna tried her best to cover her nakedness but knew she didn’t have a chance. Keith kept at least one hand on her at all times to keep her from running and Jon had locked the door anyway. Anna gasped when Keith’s hands slipped around to envelope her breasts, still hidden underneath a pink cotton sports bra. Mike pressed himself up against her and she whimpered at the feel of the hard bulge in his pants pushing up against her clothed pussy.

“You need to take her underwear off,” Laurence spoke up. He had been watching from the bed in almost complete silence. Of all the males in the room, Laurence was the only one not interested in raping his friend’s sister, but rather one of the other guys. They knew it, but they didn’t know which would be the lucky one to have his cock in their ass.

Mike used his switchblade again to swiftly slice off the bra and her panties. Anna cried silently as both he and Keith stripped themselves, alternating which one of them held her.

“Jon, why are you letting them do this,” Anna cried while Keith tied her arms back.

“I told you. They like you.”

“It won’t hurt a bit,” Mike said as he gently stroked her nether lips.

“Well, actually, it’ll hurt a lot. But it’ll hurt a lot more if you struggle,” Keith whispered in her ear, reaching around to fondle her breasts. His hard cock pressed against her ass and she groaned in spite of herself.

“Mmm… You do want it, don’t you?” Mike growled, slipping a finger into her virgin hole. Anna cried out in shock.

“Why are you doing this?” she sobbed.

“You’re a bitch. And bitches need to be put in their place,” Siberio said. “And like your brother said, we like you. Except for Laurence.”

“But I’m another story,” Laurence said, his eyes, roving over the two exposed males.

“Come on guys. Hurry up,” Jon interrupted. “I want to have a turn sometime this week.”

“No worries there,” Mike said, removing his finger from Anna. Together, he and Keith lifted her off the ground. “Ready sweetheart?” Mike whispered and thrust into her hard. Anna screamed in pain at the sudden invasion. As Mike started thrusting, Keith pressed his cock against her anus.

“Relax honey. This is going to hurt like nothing you’ve ever experienced. It’ll hurt more if you’re tense.” With those words Keith penetrated her virgin ass and was met by a deafening cry of pain. Blood provided the lubrication he needed to continue thrusting in her ass while Mike fucked her from the front. Anna continued screaming. She’d never known pain like this before and hoped never to know anything like it again. Both the boys fucking her, one in her ass, one in her cunt, was more than she’d ever thought to experience. For her first time, this was just too much.

“Stop, please!” she cried, begging and pleading, wanting the pain to end.

“Enjoy it bitch. This isn’t going to end until we’re done,” Keith grunted, gradually fucking her harder and faster.

“And then you get two more,” growled Mike with a deep thrust that made her scream. Jon and Siberio were hard as rocks listening to her cries. Even Laurence was reaching a good erection listening to her.

“Hurry up, god dammit!” Siberio yelled.

“Just… one… sec!” Mike yelled with three final thrusts. Keith said nothing as his face took a look of intense concentration and with a scream from Anna, he finished. The two allowed Anna to fall to the floor as they backed away to take their chance to recover.

Anna lay on the ground, panting and crying. Jon was the first to move. He stepped over, kneeled down next to her and very gently lifted her chin so she could look at him.

“Are you doing ok, Anna?” She met his eyes and shook her head no.

“Make them leave Jon…”

“I can’t do that sweetheart. But maybe, if you’ll suck me off, I’ll make Siberio go easy on you.”

“No…”

“Are you sure? He could really tear you up if he wanted to. And trust me, I think he wants to.” Tears were streaming down Anna’s face as she looked to her brother pleadingly.

“Ok… I’ll do it,” she whispered.

“What was that?” Jon taunted.

“I’ll do it.”

“Good girl.” He stood up long enough to take his clothes off and then knelt in front of her. “Do it.”

Anna looked up at him fearfully and then at his cock, standing erect right in front of her face. Slowly she began licking it, swirling her tongue around the base, slowly traveling up, over the head and back down the other side. She gently took one testicle in her mouth and sucked on it, then the other. Again she licked up the length of his cock and now wrapped her lips around its head, traveling down the shaft slowly. As she did this, Jon’s moans filled her ears so she knew she had to be doing something right. Before she knew what was happening, Jon thrust into her mouth and held her head in place. Anna struggled against his cock as she gagged but then relaxed, allowing her throat to adjust to accommodate his size. She teased his cock with her tongue will he fucked her mouth, right up until he came, filling her mouth. He held her still, making her swallow his load and then released her. Anna sat back, taking this opportunity to catch her breath before Siberio grabbed her from behind.

“Guess what,” he growled, spinning her around to face him. “I’m gonna fuck that tight little cunt of yours harder then Mike did. I’m gonna make you beg for mercy. I’ll make you faint from the sheer pleasure of it.” Anna swallowed nervously and nodded. Jon stepped behind her and pushed into her ass without any warning. Anna gasped in pain but he was much gentler than Keith had been. However, his gentleness didn’t make any difference when Siberio slammed into her and started fucking her hard, fast, and deep. Anna screamed in pain as his cock penetrated her deeper than her body could really handle. Even as she screamed, Jon screamed too. Laurence had decided to join in finally and he’d chosen her brother to be his pet. With Siberio fucking her to the point where she was bleeding, and Jon being fucked while screwing her in the ass, Anna felt herself on the very edge of consciousness. Her body went through the motions of what she was feeling. Screaming, crying, and moaning alternately. Before any of the three boys participating had finished, she’d passed out from pain her body and mind couldn’t take.