The Family Business Ch. 01

Anal

“C’mon, sis, what harm would it do?” Jack asked again in exasperation. “It’s not like your pussy or mouth, or even your ass for that matter, have never been used before.”

Sophie rolled on to her back from her side facing away from him and glared without saying a word. She wasn’t particularly happy about his request but she never could stay mad at him for long, especially when he twirled one of her nipples between his fingers as he was doing just then.

“C’mon, sis, it will only be six other guys besides me for your first time. You don’t know anyone other than Ben and you already fucked him before. The money will be really good too and you are always complaining about not having enough after tuition and such.”

She let out a low moan, the pinch of her nipple rippling down to her already sticky pussy. Her brother’s sperm was still seeping out of her with some crusting on her pussy lips while most dribbled down over her asshole to puddle under her ass cheeks.

“OK, before I say I’ll do it for sure, tell me exactly how this is going to work and you will keep me safe,” Sophie murmured, turning to her brother so she could wrap her fingers around his half hard dick still slippery with the remnants of his own cum and her pussy juices.

Jack grinned and leaned forward to flick his tongue across one of the erect nipples capping her tiny conical tits. Sophie groaned again and threw her knee up over his thigh, some of the gooey mixture leaking out of her cunt smearing over his hip.

“Like I said before,” Jack continued, shivering slightly when she ran her fingertip over the sensitive head of his dick, “Ben’s getting married and I have to put on the bachelor party. All the other guys coming are our classmates and you never met any of them. I won’t even tell them your my younger sister. We’re all chipping in to cover the room, booze and entertainment…you. You get everything after those other costs, so you start getting some cash right up front. All you need to do for that is strip real sexy like and parade around naked for a while. If anyone wants more, that’s entirely up to you if you want to do it or how much you charge. I’ll be there the whole time, so you’ll be safe.”

When she started cuddling up under his arm, Jack was pretty sure she was going to agree. He stretched his arm over her shoulder, dragging his hand down over her back until brushing across her ass and splitting her cheeks with one finger. She trembled again and pressed her ass back against his hand until his fingertip swirled around her sensitive asshole.

“Yeah, she’s gonna do it,” Jack thought to himself before pushing her onto her back and kissing her deeply.

His sister returned the kiss with growing passion, feeling her pussy quiver even before the increasing hardness of his dick pressed against her belly. He pushed her legs up, spreading her thighs and pussy lips. She grabbed her own legs behind her knees and pulled them even higher.

“My ass…fuck me…in my ass…this time,” she gasped, rubbing her clit furiously as his mushroom head split her asshole and her brother buried his cumming cock deep in her bowels.

Sophie knew she was going to do it from the moment her brother first mentioned the idea. She just wanted to string him along some and make him squirm before agreeing.

The idea appealed to her for several reasons besides the money, which she really needed to finish her second year at the university. She wanted to fuck Ben again anyway after that time last summer with him and her brother and his bachelor party might well be her last chance for a while. Besides, she was finally ready and this was her first chance to fuck and suck a bunch of guys she didn’t know for money as opposed to the regular family gatherings.

After Jack finished cumming in her ass, he collapsed on the bed and nodded off to sleep. Sophie got up, wiped the jism leaking from her pussy and ass and went to get something cold to drink.

**********

When she entered the family room, she saw her mother hunched over the computer. Sophie walked up behind her and wrapped her arms around her neck, letting her hands roam down to twirl her mother’s dark erect nipples.

“What are you watching, Mama?” Sophie asked, knowing before saying a word how sincan escort her mother would respond.

“Oh you know, sweetie, my favorite videos, the ones with young girls playing with older women,” Lena responded, “the way I like you to play with me.”

On the screen, a woman at least her mother’s age, with a big ass and floppy tits, was eagerly licking a much younger woman’s smooth bare pussy while pounding two fingers into her pussy and one into her asshole. Sophie could feel her mother’s arm moving back and forth as she played with her own pussy.

“Want me to help you out, Mama?” Sophie asked as her mother began to tremble, her usual precursor to a sloppy orgasm.

“It’s…OK…sweetie…I’m…I’m already…CUMMING!” Lena screeched, a gusher of her pussy juices spurting out under the desk to puddle on the floor, before she collapsed back into the chair.

“Damn, Mama, I think you are squirting more and more every day,” Sophie murmured in her mother’s ear and, with another loving pinch of Lena’s nipples, walked into the kitchen.

Her father stood at the counter wearing only an apron as he chopped and sliced in preparation for dinner. Sophie stepped up behind him, stood on her tiptoes and flicked her tongue into his ear. At the same time, she slipped a hand under the apron to fondle his flaccid dick and low hanging balls. He stopped chopping and pressed his ass back against her.

“Keep that up and I’ll either cut off a finger or will have to fuck you right here,” he grinned as his dick stiffened in his younger daughter’s hand.

“Decisions…decisions…decisions,” she laughed before pulling her hand away from his cock and giving him a gentle slap on the ass. “Tell you what…you finish making dinner and you can have my pussy for dessert. Besides, I need to talk to Anna.”

“It’s a deal, sweetie,” Aldo responded and went back to his dinner preparations.

Sophie wandered down the hall to her older sister’s bedroom, walked in without bothering to knock and climbed on the bed. Anna was standing in front of a full length mirror holding up a new outfit in front of her. Several others were piled on a nearby chair.

Anna was naked save for the hiphugger panties that clearly accented her taut low slung ass, protruding mound and the deep crevice disappearing between her legs. Sophie rolled on her stomach with her feet in the air. Since her own tits proved to be little more than the bumps of her nipples, Sophie was always jealous of her older sister’s firm round boobs, with the light tan eraser sized nipples, that were still winning the never ending battle with gravity.

“Does this look good?” Anna asked, turning while holding up a pale blue dress that looked to Sophie like it would either cover her tits or her pussy but not both.

“Sexy,” Sophie responded and watched her sister drop the blue one and pick up another.

“How about this?”

“I like the blue one better.”

They went back and forth for a few minutes until Anna went through every one of the garments, ultimately settling on the original blue one. She hung the others back up and crawled in to bed next to Sophie.

“Did Jack ask you yet?” Anna said while carefully examining her own thin strip of cunt hair leading to her pussy slit.

“Yeah, a little while ago.”

“You gonna do it?”

“I was wondering why you weren’t doing it, after all you have all the experience.”

“Well a couple of reasons,” Anna explained, turning her full attention to Sophie. “First, he already has me booked for that night with a very wealthy lady and her boy toys. That’s what this dress is all about. Second, those guys are barely out of college and really can’t afford my rates. Third, and most importantly, it’s time for you to find out if you like it, since fucking a bunch of strangers for pay is a long way from doing your father and brother and other family members, even when all at the same time. So what did you tell him?”

“I’m gonna do it. I just can’t resist him,” Sophie admitted.

“He did that little trick with your nipples while he asked, didn’t he?” Anna giggled and tweaked one of Sophie’s tiny tits, causing her sister’s pussy to clench.

“Yeah, it’s like there’s a direct line to my cunt,” sincan escort bayan Sophie moaned softly, feeling the first hint of moisture seeping to her inner thigh. “God…that feels so…fucking…good.”

Anna grinned before bending forward and taking her sister’s other nipple between her teeth, sucking and pulling at the same time. Sophie let out a loud moan. She pulled Anna down to her then pushed the top of her head down across her belly until her tongue flicked over the thin thatch of hair still topping Sophie’s pussy slit.

Two of Anna’s fingers breached Sophie’s pussy hole just before one plunged into her ass and Anna furiously sucked her clit. Sophie’s orgasm exploded on her sister’s face.

She clamped Anna’s head between her thighs until the last remnants of her climax faded away.

“You really need to shave off your cunt hair completely,” Anna said to Sophie as they regained their breathes on the bed. “With your tiny tits and a smooth bare pussy, you’ll look more like a little girl. Many men will pay a lot to fuck you like that. I’m surprised Papa or Jack haven’t suggested that to you yet.”

**********

“There is one other thing,” Jack said to her as they pulled into the hotel parking lot. “Make sure you concentrate your attention on Ben first when you strip…and either fuck him or give him a blow job before you do anything with anyone else.”

“I thought I had a choice about doing any of that,” Sophie said, staring at him coldly from the passenger seat.

“You’re the entertainment…so you have to…entertain,” her brother answered as he pulled the car to a stop in a far corner of the parking lot. “Now let me get a last look at you before we go in.”

Sophie was wearing the outfit Jack bought for her a couple of days earlier. The very snug cutoff tank top ended just below the underside of her small bare tits. The short skirt barely covered her thong and was so tight she had to pull it up around her waist to sit in the car for the ride to the hotel. The five inch heels made both her feet and calves hurt.

They entered the hotel through a side door that was only a few feet from the suite. Before he opened the door, Jack turned to her, gave her a tender kiss then tweaked both her nipples until they popped out against the thin fabric of her top. Then he drew one finger up between her legs feeling the small moist stain seeping from her freshly shaved pussy into her lacy panties.

“Nice, sis, I’m so glad you are getting into this,” Jack grinned, bringing that sticky fingertip to his lips.

With that he drew a credit card like key from his pocket, swiped it on the lock and pushed open the door.

The low buzz of conversation in the suite died out as they entered. The six guys drinking beer in the room looked up expectantly. The lecherous grins creeping across their faces caused a familiar warm tingle to grow in Sophie’s pussy.

Despite all the reservations she voiced with her brother, she had every intention of sucking and fucking every one of them for as many times each could manage to cum in and on her. Her masturbation fantasy since she agreed to do this first group was feeling her tits and face covered with their sticky jism while even more leaked out of her pussy and ass down the inside of her legs.

“Hi, boys,” she said with the most sultry voice she could manage.

“Showtime!”

**********

“So, how did it go?” her mother asked as she poured herself a cup of coffee and sat down next to Sophie at the kitchen table as the next morning merged into afternoon.

Sophie looked up and smiled wanly. Her pussy, ass and jawed all ached, as did the bite marks and hickeys on her neck and tits. She immediately noticed several distinctive teeth marks on both of her mother’s plump sagging breasts.

“It was fine but what happened to you?” She asked her mother as she sipped her coffee.

“Oh, your father booked me with Jeremy again last night,” she answered with a slight grin, “he’s been a regular for a long time but a bit on the dim side, tends to get a little carried away at times. But enough about me, I want to hear all the details about my little girl’s first gang bang with paying customers.”

“So do I, so wait until escort sincan I get my coffee,” her father announced from behind her before bending forward and kissing Sophie on the cheek, his hands gently grasping for her tiny tits and his half hard cock brushing against her back.

He went to the counter and brought back the pot, replenishing his wife and daughter’s cups before filling his own. Sophie’s pussy clenched a little watching her father’s long, thick dick and his dangling balls sway freely between his legs.

“Let’s move into the other room,” her mother suggested, getting up and walking into the family room. She had a few bite marks on both ass cheeks too.

While her mother and father settled in on the couch, Sophie took one of the recliners. They all had unobstructed views of each other. Sophie’s pussy twitched a little seeing the crusty remains of someone’s cum caked in her mother’s dark cunt hair. No doubt before long she would find out whose it was, although she suspected is was nothing more than her father fucked her mother earlier in the morning.

“So, sweetie, how did your first gang bang for pay go?” her father asked, the bulbous head of his limp uncut dick just barely peeking out from beneath his fleshy foreskin.

Sophie knew he would get incredibly hard as she told them every little detail, the way he did when he listened to her describe the ways she masturbated since the days when she first started to finger her own bare pussy.

“There were six guys besides Jack,” she began, one hand squeezing a tit and the other brushing over her swollen mound. “I walked around and touched them all the chest or face until I stood in front of Ben. I danced around a little while pulling off my top and let them all get a good look at my tits before bending over to unzip Ben’s pants.”

“After he took his cock in his hand I stepped back and slowly stripped off the skirt, with my ass almost in his face. I turned back to him and let him pull my thong down over my knees. By then, the other guys all had their cocks out and in their hands as they moved closer.”

“I dropped to my knees and started to lick and suck Ben’s throbbing dick. Even before I tasted the first drop of his precum, some of the other guys were squeezing my tits and fingering my pussy.”

“Wait a minute,” her father interrupted, the purplish head of his cock already completely out of its foreskin in his hand, “what did your brother do about the money?”

“At first, he was going to charge them for each thing, like touching my tit or getting a blow job, but that didn’t work well in practice, “Sophie responded. “So, he just had them all empty their wallets and turned them loose. By that time, I already had Ben’s cock buried in my pussy the first time.”

“Hmm, I’ll have to talk to him about that,” her father said as he slowly stroked himself harder, “there are better ways to handle that situation.”

“So how many of them ended up fucking you?” her mother asked as she pinched a nipple with one hand and fingered her own clit with the other.

“All of them, I think,” Sophie answered, feeling her own juices beginning to seep from her cunt and on to her fingers and inner thighs, “at least four in my pussy and two in my ass before I started to lose count. I’m pretty sure I sucked all of them off until they filled my mouth with cum too.”

“Oh sweetie, that’s really hot,” her father groaned. “I’m going to have to be there the next time to see for myself.”

Sophie got up and walked over to the couch, kneeling between her parents so she could take her father’s throbbing cock into her mouth while fingering her mother’s dripping pussy. Her father tensed and shot his load of cum down his daughter’s throat right before her mother soaked them both with her pussy juices.

When her parents were done cumming in and on her, her mother rolled Sophie over on the couch and buried her face between her daughter’s thighs, eagerly licking Sophie from her asshole to clit and back again a few times until Sophie’s own orgasm exploded on her mother’s face. Her father looked on with a big smile until both his daughter and his wife collapsed back on the couch.

“You know, I have a new customer who very much wants, and will pay extremely well, to fuck a real mother and daughter together,” he said huskily. “With your shaved pussy and tiny tits, you look a lot younger than you are…just like a really little girl.”

“Of course, Papa,” Sophie grinned, “whatever you say…anybody…anytime…anything…anything at all.”

**********

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