Risky Business

Vanessa cast her brother an annoyed look even as she smiled at the men in front of her. The four men were her brother's business associates, visiting from the parent company, and he'd been charged with showing them a good time. Which meant finding female company for them. Of course, Ian was too straight-laced to know how to go about hiring prostitutes. Instead he was forced to beg his sister to come down to the club and bring some of her friends.

At first Felica refused, but then Ian gave her the puppy dog eyes and promised to pay each of them for their time. He also said that he would owe her one, which would come in handy next Christmas when they went home to visit. Ian was in their parents good graces, Vanessa was not.

She knew she'd have to call in some reinforcements. Luckily, she had some favors of her own that were owed to her. She called her Celene, her best friend from work and a self-diagnosed nymphomaniac, and her college roommate Alexis, who was putting herself through school by doing lap dances and (Vanessa assumed) a little extra on the side.

Celene, a petite Latina with bright green eyes and a mop of curly black hair, was already curled up on one man's lap as he regaled her with some story, her hands unbuttoning his shirt as she kissed his neck. Alexis, a statuesque blonde who look liked she stepped out of 'Sports Illustrated', was busy explained her lap dance technique to another man, demonstrating the more impressive maneuvers.

Vanessa herself was sitting next to her brother and across from two men that were obviously related. And, if she had to guess by the age differences, were likely father and son. Ian was nodding his head and apologizing nervously to the older man, probably the big boss, while the younger man stared with undisguised lust at the word pussy written on her tank top.

"I didn't realize your son would be coming too, Mr. Yancey, or I would have brought another girl," Ian was saying, his voice not wavering even as his hands shook.

Vanessa eyed the boy next to the boss and guessed why her brother hadn't thought he would come. He looked like a freshman or sophomore in college, someone who probably shouldn't be allowed into a bar at all, let alone a private room at a high end cocktail lounge like the one they were in now. Which, again, showed how straight-edged (read: out of touch) her brother was.

"Let me see them titties," the young man sitting next to the Boss said suddenly, unable to restrain himself any longer.

Ian shot him a shocked look, but covered it up before either of the other men noticed. Vanessa just smiled and pulled up her tank-top in one fluid movement, not having bothered to put on a bra. "I hope they're to your liking," she said, leaning forward so they bounced.

"Oh, yeah," he said as he licked his lips. He tore his eyes away long enough to give Ian a thankful glance and lean in to whisper something to his father.

The Boss laughed as he turned to regard Ian. "Jasper's right. You've been such a great host, man. I've never seen such fine girls." He grinned wolfishly. "My son and I want you to join us in fucking the pretty brunette, here."

Ian went pale and Vanessa almost couldn't hold in the laughter. "I--," her brother began and Vanessa stomped on his foot. Surely he wouldn't be stupid enough to just admit that he was offering up his sister as a party favor, but why take the risk? Of course, he had no way to get out of it without seeming like he was being ungrateful.

Vanessa considered letting him hang in the wind, but decided to take pity on her brother instead. She leaned forward, looking at the Boss and his son as she brushed her fingers over her neck. "Three might be a little too crowded." she said, shrugging her shoulders and pushing her breasts together with her arms. "And I'd prefer to be between the two of you."

"It would be bad taste to leave out the host," Mr. Yancey said, before casting a glance over at his son, who was once again mesmerized by Vanessa's breasts. "As much as I hate offering up sloppy seconds, how about he take the place of whomever cums first."

"Sounds like a fun little game," Vanessa agreed as her brother let out a sigh. She knew he was hoping they would forget their offer once they got started. She cast a glance at her friends as she stood up and moved toward the Boss and Jasper. Celene was on her knees with her face buried in one of the men's laps, giving him a champagne room-worthy blowjob. Alexis was making a loud show of riding the other guy. Both of them seemed suitably preoccupied.

Jasper got up to meet her, almost immediately grabbing hold of her tits when he could reach them. Vanessa smiled coyly and made a cooing noise as the Boss moved to stand behind her, pressing himself against her back and forcing her up against his son. Jasper's erection rubbed against her thigh as he squeezed her breasts, his head dipping down to lick and bit at the nipples. She moaned as he caught a nipple between his teeth and pulled on it, her head lolling back to rest on the Boss's shoulder as he sucked on her neck, his own erection pressed hard between her ass cheeks as his hands worked her mini-skirt up over her hips. The older man was eager to get inside, but was waiting for his son.

At first Vanessa was worried they were both going to try and fuck her cunt. Celene could do double-penetration, but Vanessa wasn't quite that experienced. Fortunately, as she let the two man rub and bite and grind against her body, it was obvious that the son had a breast fetish and the Boss like anal, if the way he was dry humping her ass was any clue. She was glad she had taken care to make sure that entry was slick as possible before she left the house.

Her brother was watching and he seemed to be both enthralled and disgusted at the sight of his sister between two men. Vanessa smirked to herself and bucked her lips, grinding against the Boss and then his son. Ian had always hated her wild side, even if it was helping him now. He had wanted to be the big brother that protected his sister. She had to admit, she sometimes felt a little guilty not letting him.

Vanessa let out a little cry as Jasper twisted her nipple and she looked at him. He grinned at her, the look of a spoiled rich boy. "I wanted you to see the main attraction," he said proudly as he unzipped himself.

"You're so long," Vanessa complimented in fake awe. His cock was long, but it was also skinny. Jasper looked proud of himself as his father grabbed hold of her hips, steadying her to let his son slip fully inside. "You feel so good," Vanessa said as Jasper grabbed her hips and his father forced himself in the back way.

Vanessa was really glad Celene had suggested the lube as he did, the Boss was much thicker than his son. He probably liked anal because of how tight it was. "Oh," she moaned as the Boss whispered into her ear that she should call him 'sir'. "Oh, sir."

Vanessa groaned and writhed as she was pounded back and forth between the two men. She loved the feeling of being filled with cock, there was nothing better than hard flesh pumping in and out of her holes. The sense of completion was hard to replicate.

At first father and son had worked in a rhythm, bouncing her back and forth like they were playing tennis and she was the ball. But Jasper began moving faster, with erratic movements, trying to plunge himself in as deeply as possible. While his father continued with slow, tormenting thrusts that were more arousing than his son's rapid jerks.

Jasper came with a yell, exploding deep inside Vanessa with a final thrust. The Boss laughed as his son collapsed back onto the couch, his flaccid penis framed by his unzipped black pants. "Staying power, my boy," he said, thrusting deep into Vanessa and stopping, holding her around the waist to prevent her from trying to move.

"Oh, I'm sure he'll grow up to be a big man like you, sir," Vanessa said, trying desperately to shift herself. It was torturous to have that thick, hard flesh inside her and not be able to move.

"Hold on, dear," the Boss said, wrapping his other arm around to hold her still as he thrust himself in a little deeper. "Ian, it's your turn."

Vanessa looked over at her brother and blushed a little. She had been so absorbed in being fucked she forgot he was there. He looked horrified to her eyes, though the two men probably didn't notice.

"Her cunt's nice and tight," Jasper said, lighting up a cigarette. "You'll like it, Ian."

"I—," Ian began, nonchalantly rubbing a hand over his stomach.

"No one's been in my mouth, sir!" Vanessa ad-libbed to the Boss, "...if he'd prefer a bit of unclaimed territory." She knew her brother well enough to guess the gesture meant he was worried about her getting pregnant, and all of a sudden mentioning she was on birth control would seem rather odd.

"Ian?" the Boss asked. Vanessa hoped he would get up and unzip. After all she had done, she was going to be seriously pissed off if her brother screwed up his business dealings now. Besides that, she had a six-inch cock firmly crammed her ass, and it wasn't moving until he did.

"I do like a hot mouth," her brother said, and Vanessa smiled to keep from laughing out loud. She doubted her brother had ever had sex in anything other than the missionary position with the lights on and his socks off. He stood up from the couch, unzipping his pants and pulling out his erection.

"I knew you were a good man," the Boss said, clearly impressed.

Vanessa wasn't sure what was more surprising. That her brother had a huge fucking cock or that watching two guys banging her had turned him on. The Boss let climb on the low table, so that she was on hands and knees, perfectly lined up with him and facing her brother. She licked the precum from the tip of his erection as the Boss began pumping her from behind again, much harder this time. Vanessa was too busy admiring her brother to do more than thrust back against him every once in a while and moan when he slapped her ass, as though he were riding a horse. It felt wonderful, but she was entranced by Ian.

Were there time she would have liked to worship her brother's cock, to fondle and stroke it. But there was an audience, Jasper was watching intently, and the Boss was moving quickly toward his climax. Vanessa glanced up at her brother's apologetic and embarrassed face before she took him into her mouth, completely. He let out a gasp and Jasper actually applauded as she did so.

Her head began to bob, attempting to keep pace with the pace the Boss was setting from behind. "Oh, God," her brother moaned as she moved a little faster.

It was heavenly. Vanessa had never had such an awesome threeway before. She felt filled to the brim. Jasper's cum dripping down her thighs, the Boss pounding against her from behind, and a huge cock down her throat. Even if the last did belong to her brother.

Ian seemed to slowly forget it was his sister's mouth that he was fucking as his hands fisted in her hair and he began thrusting insistently into her mouth, pulling her to meet him. If her brother's enormous cock weren't parting her lips in a wide O-shape, Vanessa would have smiled proudly.

The Boss finally came inside her, grabbing her hips with bruising force before collapsing against her. Vanessa let out a moan in her throat as he did, which was all her brother needed to bring about his climax. He jerked away as he felt it coming, pulling out of her mouth and cumming all over her face.

"Excellent," Jasper cheered, looking at his spent father. "Look, Ian likes to cum in a bitch's face, too."

Ian zipped himself up, looking over at his sister before looking away, unable to meet her eyes. Vanessa sighed. They would have to talk about this later. Though, she wasn't sure how she was going to broach the subject of how perfect his cock was. Maybe she should keep that thought to herself.

"You were all so good," Vanessa said, pulling her skirt down again and retrieving her shirt to wipe the cum off her face as she looked over at the Boss, now sitting beside his son. "Especially you, sir. I don't think I've ever been fucked so thoroughly. Ian was right when he said I'd have a good time."

The older man grinned proudly before looking over at the other members of his party. "I know Jasper and I had a good ride. What about you fellows?"

"Best business trip I've had in a while," the man Celene had been sucking off said. Alexis's partner nodded in agreement as they watched the two girls in action. Alexis was putting on a show of licking the cum off Celene's face, though she spent most the time trying to slip her tongue down the Latina girl's throat. Celene, for her part was trying to get Alexis's bra back on, but her hands kept 'accidentally' slipping and groping at the other woman's breasts.

The Boss turned back to Ian and gave a satisfied smile. "Admittedly, I was a little leery when I came here, but after the way you have treated us, Ian, I think we can continue doing business with your company."

"Thank you, sir," Ian said, relief clear in his voice. Vanessa made a mental note to ask him what had been going down. It had to be pretty bad for him to have asked her for this much of a favor. "Would you like me to get you back to the hotel now? The limo is waiting."

"Yes, early flight and all," the Boss said. He stood up and so did the others, causing Celene and Alexis to stop their play. "Ladies, it has been our pleasure," he said before walking out of the room, followed by his son and the other men. Vanessa waved at Jasper, having not put on her shirt just so that he could stare at her breasts for a little while longer. He winked at her before he left the room.

"I'll call you." Ian mouthed before he turned and hurried after them.

Vanessa pulled on her tank top, amused that it was covered in her brother's cum that she had wiped off her face, as she heard her friends come closer.

"So," Alexis said, wrapping her arms around Vanessa's shoulders and pressing her breasts against Vanessa's back. "How come you never told us your brother has such a gigantic cock. Celene and I would have "one this for a fuck instead of cash if we knew that."

Celene put her head down on Vanessa's thigh. "I still might offer to give him a refund if he'd rather pay that way," she said as Vanessa began playing with her hair.

"He's so boring about sex, I honestly had no idea." Vanessa admitted. "I thought that since he couldn't keep a girlfriend, it was teeny-tiny."

Celene nodded understandingly.

"How'd it feel to have him fuck your mouth? I bet you wish he'd done your pussy." Alexis said, wrapping her legs around so that she was pressed up even harder against Vanessa's back. Vanessa felt her friend's cum soaked cunt pressed against her lower back.

"Her ass," Celene put in. "You know how Nessie likes anal sex."

"He's my big brother!" Vanessa said and her friends giggled at the word 'big'."

"Who gives a shit? He's hot!" Alexis said finally.

"And if he's really boring and doesn't know anything, you can teach him right," Celene chimed in. "So many guys learn to do it wrong. I think it's your sisterly duty to show him the right way to fuck."

"As your friends, we'd help," said Alexis.

"Of course!" Celene nodded, nearly purring as Vanessa scratched her head.

"First, lets see if he can ever talk to me again." Vanessa said. She was a little worried that he would try and hide from her. Or that he would start apologizing without listening to what she had to say. Or that he would be completely disgusted that she wanted to repeat the experience. Though, if he dared call her sick because of it, she could point out that he'd been turned on by watching her having sex with two men she'd never met before.

Vanessa grinned.

Ian had said that he would owe her one for this. Now she just had to think of the best way to collect.