Role Playing Sessions

As Izzy sat on the stool of the dive bar, she looked out of place. She'd been planning on going out with her friends from high school and had dressed up in a tight flitting short blue dress for the occasion, but she hadn't been able to bring herself to do it. There was no way she could afford to go out to expensive clubs that night.

Typically, she was not the worrying type. She was the sort of girl who always had a smile on her face and for whom things always seemed to go right. But, her luck had run out the night before. For her first night home with her little brother after her third year of college, she'd disobeyed her father's direct instructions and gone for a joy ride in his prized Mustang. He'd spent years restoring it; using the small amount of money he had left over from each paycheck.

She and her little brother Luke had slammed it into a tree, and while they hadn't been going very fast, the damage was severe. The earliest quote placed repairs/restoration at roughly around $5,000, and her parents would be back from their cruise in two weeks.

She had no idea how she was going to come up with that sort of money. Especially since the shop said it would be extra to have it repaired by the time he came home.

So, for the first time in years, she was actually worried.

"How the fuck am I going to come up with $6,000?" she asked herself under her breath as she took a sip of her drink.

She was in no mood for company when the obviously inebriated redneck sauntered up to the bar.

"Well hi there, li'l lady," he said with a slur. "What's a...fine....girl like you doing in a place like this?"

As she glanced over at him, it only took one look to know that she was far out of his league. She hated to think like that, because she really wasn't a stuck up person, but she just wasn't in the mood to be hit on by some hick at that moment.

"Look, I'm not interested in whatever line you have next. Go find some redneck girl. There's plenty of them in here." she said dismissively.

"Ah come on now, don't be like that," he said as he ran a hand over her back. "You don't know what I've got." He burped disgustingly, but then reached into his pocket to pull out a wad of $100 bills. "Y'see, I just came back from a rig. Made some good money. So tell me li'l lady. What'd it take to get you back to my place?"

"Listen," Izzy started. She had no time to be messing around with some drunk redneck. But just as she was about to tell him to get lost for the second time, it hit her. She sat there, staring at the wad of cash in his hand as the solution to her problems suddenly became clear.

The hick was surprised as her face lit up and she wrapped him in a hug.

"OH MY GOD! You're a genius!" she said as she let go of him and grabbed her purse to run towards the door. She stopped quickly though, and ran back. She reached behind the bar and pulled out a pin. Jotting her number down on a napkin, she shoved it into the hicks hand.

"Here, hold on to this and give me a call tomorrow!" She gave him a kiss on the cheek and then ran towards the door. She had to tell Luke!

"Don't forget to call me!" she yelled as she ran out the door.

"Okay, hear me out because this is going to sound crazy," she said when she got home.

Luke was in the middle of playing a video game, and he was kind of pissed at being interrupted, but when he saw his sister in her tight dress with a bright smile on her face, he forgot all about the game.

"I like crazy," he said. "Crazy is good. Hit me with the crazy."

Izzy plopped down on the couch next to him, brushing a strand of hair behind her ear. Her short skirt rode up even higher on her thighs as she crossed her leg under herself. Luke tried not to focus on that. He also tried not to focus on how her nipples seemed to be poking through the thin fabric.

"What if I...ohmygod, this is so stupid but so perfect...wait, let me back up. So this guy, okay? I'm at the bar, waiting on my friends, and this guy comes up to me. He's such a hick. I was so over him. He's all, 'hey, little lady' and stuff, and I'm like 'nope'. But then he takes out a wad of cash. I swear, it's like a fist full of Benjamins, and he's all 'what will it take to get you up to my hotel room?'"

Luke just nods, listening.

"And I'm like, 'ohmygod, that's it!' so I gave him my number, and tomorrow I'm going to fuck him for money. I'm going to sell my body, Luke. Why did I not think of this sooner? I'm hot enough, right? I mean, people would pay for this, wouldn't they?"

Izzy stood up and gave her brother a little dance, lifting her skirt hem provocatively.

"Uh, I mean..." Luke shook his head, completely mesmerized by his sister's body and unable really to respond, much less to process the idea of her becoming a prostitute.

"Luke, be honest," she said, lifting up her skirt and showing him her bare legs and her thong. "Guys will want to fuck me for money, won't they?"

Luke was always a clever kid, and usually the funniest one in his class, so he was often quick on his feet, even when caught off guard. It was one of the reasons that Izzy liked him so much. So, despite the fact that his mind was reeling, he had the presence to say:

"I don't know. Take the dress off and let me get a good look."

And despite the fact that he was her little brother, and just fifteen, she lifted her dress up over her head and let it drop to the floor, revealing her full, ripe breasts to him.

"Fuck yeah," he moaned in reply, putting a pillow in his lap to cover up the immediate erection in his short. "I mean...uh, yeah, I think so."

"Awesome!" she said, grabbing his hand and pulling him to her bedroom. "Help me pick out some sexy outfits to get fucked in."

Luke had to drop the pillow as she pulled him along, but part of him didn't care anymore. He was staring at his sister's ass in nothing but a thong, and he thought, "You know what? An erection is the right response to that."

As they went upstairs and picked out an outfit, it never struck Izzy as strange that she was walking around topless in front of her little brother. She'd always had an open-mind about sex, and her body was hardly anything to be ashamed of!

As she noticed his erection as he sat in a near-trance watching her pick out different underwear, she actually grinned. "Well, if I can make my brother hard, I should have no trouble with anyone else!" she thought to herself.

"I don't know why I didn't think of it sooner," she said as she compared two thongs. "I mean, I know a girl in my classes who is putting herself through college on her back. That's $16,000 a year! I mean, sure, we only have 2 weeks to raise $6,000, but I'm sure we can do it. I texted her to find out what website she uses so we can set that up next...just as soon as we have the right outfit."

"You'll have to take the pictures of course....but, how about this?" she said as she posed in a sexy take on a Disney outfit she'd once worn at a Halloween party. It was similar to a one piece swimsuit, but with most of the middle missing, and with wisps of cloth reminiscent of a snow-white like sleeves.

"Wow sis, uh, p-perfect," Luke said as he ogled his sister.

She took to the bed, striking various poses that made his erection strain in his shorts as he snapped photo after photo.

When they were all finished, they went to his computer to upload the pictures and make her ad.

"Jeez, sis," Luke said as he brought up the website since he was the tech nerd of the family. "The last time I was on here we were listing dad's unused parts for the mustang."

Rather than feeling demeaned, Izzy smiled. "And now you're listing your sister to get fucked!

He laughed as he uploaded the pics then began her profile. "Okay, description..."

"Hmmm," Izzy said as she thought. "Well, we need to raise cash fast, so write this: 21 y/o girl who's looking to make your dreams come true. Everything is on the table...for a price. Fetish friend. You're fantasies will be my reality."

"How does that sound?"

Luke laughed, happy to have the laptop covering his erection. "It sounds like we'll have that money in no time. So, how much are we going to charge?"

"I don't know," she said as she stood up, thinking. "What would you pay to fuck me?"

He blushed quickly, but recovered fast as well, "I don't know. The average price on here is like $150 for an hour, but you're way hotter. So like, $250 per hour?"

"Sold," she said with a grin. "Hit send and then let's go get a hotel room!"

"You mean...I'm coming with you?" he asked.

"Well sure. I've got to have some sort of security. Besides, I promise I won't moan too loud when they fuck me." she said, semi-teasing him as it was becoming increasingly clear he was turned on by her.

When they got to her hotel room, she gave Luke her camera.

"When you hear me opening the door, you take the camera and get in the closet. I'll jiggle the door handle a few times, acting like I'm having a hard time getting it open. Who knows, maybe I'll be so nervous that I won't have to pretend. But either way, it will give you enough time to get hidden."

"Okay," Luke said, checking out the room. "But what's the camera for?"

"I want you to take pictures of the guy, so that if he does anything bad to me, we'll be able to report him. Or at least, we'll put his picture up on the website to let other prostitutes know to look out for him."

Luke nodded.

"Okay, let me get in the closet and check it out," he said.

He was able to see between the louvers on the closet well enough.

"Let me try taking some pictures, get on the bed like you're having sex."

Izzy laughed. "Okay, like this?" she said, laying back in a sexy pose.

"Perfect," he replied, snapping a picture. "But more sexy and less clothes."

"You just want to see me naked," she teased, secretly pleased that her brother was angling to see her body. "Does that mean that you think I look hot?"

"The shorts are cute," he replied, "but they'd be cuter on the floor."

"Damn, bro," she laughed, unfastening her pants and pushing them down. "When did you get game like that?"

"And the top is nice, but not as nice as your tits."

"Nope, not as good as the first one," she chuckled, but she slipped it up over her head anyway.

"Fuck yes," he whispered, snapping away.

"I heard that," she giggled.

Izzy got up and walked over to the closet, looking to see how visible her brother would be from in there.

"I think this will work," she said, opening the door completely naked. "And I just want to say," she reached out to touch the bulge in his short, "how much it means that you're doing this for me."

Luke's body involuntarily jerked at her touch, making her smile.

"But I don't want you distracted by your libido, stroking your dick while I need you taking pictures," she said, squeezing his small hard-on. "So that's why I'm going to suck you off right now. As a way of saying thanks and as a way to keep your mind on the game."

Izzy dropped down to her knees in front of her brother and pulled the elastic waistband on his short down.

"And no pictures while I'm down here," she said, looking up at him while she reached in and took ahold of his cock. "Because that would be kiddie porn."

He moaned as he felt her fingers wrap around him.

"Just kidding. I totally want a picture of me on my knees with your dick in my mouth. I want to remember how this crazy accident brought us closer together."

Luke was panting as he raised the camera and watched the Izzy on the viewfinder screen take the cock into her mouth.

"Fuuuuuuucccckk," he whispered as he felt her warm, wet mouth envelop him.

Luke moaned as he felt his sister's warm wet mouth on his cock! "Oh fuck Izzy! I can't believe you're actually doing this....oh God! Yeah, suck it sis! Suck my dick!"

Izzy knew it was wrong to be doing it, but it just didn't seem that wrong to her. He was her little brother and they'd always been close. So what if they were siblings? He was the coolest little brother in the world, and he was helping her do something most brothers would freak out over. Instead he'd completely crushed on her, so he deserved to get sucked off.

As she looked up at the camera, she felt a different thrill though. She'd pushed past two boundaries; pedophilia and incest, and that sent a sense of excitement throughout her. Even better, it was being completely documented.

She sucked harder, slurping on his 5" cock as his moans grew louder.

"S-sis," he half warned out of courtesy to her, but as she looked up, she could see his desperate plea in his eyes, begging her to eat his cum.

She nodded up at him as she kept going and heard the relieved sigh as he surrendered to the impending orgasm, knowing he could cum in Izzy's mouth.

His camera hand wobbled as his body began to jerk.

"OH FUCK! OH GOD! LIZZY!" he grunted. "LIZZZZZYYYYYYY!"

She never slowed down as his young, incestuous cum sprayed out from his balls into her mouth. There was a surprisingly large amount, and she hungrily slurped glob after glob down as her brother continued to unload into her willing mouth.

"Yessss," he groaned as his cock twitched and his hips jerked. "Eat it," he begged, "eat it all, Sis!"

She kept going until she seemed to suck the will out of his body to stand. He collapsed back against the wall, resting against it as she slurped the last drop of cum from his softening cock.

When he looked down

at her though, her typical happy, nearly flippant smile was gone, and replaced by a more meaningful, yet still happy expression.

"Thanks for coming with me to do this," she said as she rested back on her heels. "I'm lucky to have such a cool brother, and I want you to know I love you."

Luke was speechless. He collapsed onto his knees in front of her and wrapped her in a hug, feeling her heavy, ample breasts and her soft back. "I love you too sis," he said, holding her tightly as they shared one last intimate moment together.

"Plus," she said as her usual smile returned and she gave him a kiss on the cheek, "I'm lucky to have a brother who's cum tastes so good!"

"Well there's plenty more where that came from," he said with a laugh. "I don't think any girl's ever going to beat you at sucking my dick."

"Good," she said with a laugh as she stood up. "Because the summer's just started and I love giving head."

As she said that, the phone rang. Her pulse spiked and she gave Luke a nervous grin as she answered.

"Hello?"

"Yes, is this Izzy?" a male voice asked.

"It sure is, what can I do for you?"

He was clearly nervous, but skeptical too. "I was just wondering if your'e really the girl in the ad. she was...hot."

Izzy laughed, "It's me. Why don't you come see for yourself?"

They arranged the room number, and 10 minutes later they heard the knock on their door.

When Izzy opened the door, she was greeted with the smiling face of a guy who was a head taller than her.

"Uhm, hi," he said. He started to offer her his hand but then apparently thought that was dumb and just dropped it to his side.

"Come on in," she said, ignoring his faux pas. "I'm Izzy," she said with a smile.

"Steve," he said, nodding way too much. Then he apparently realized his head was bobbing on its own, and he stopped moving all together.

The silence between them was uncomfortable, and then Izzy realized that she was the one who was supposed to do something about it.

Oh well, since it's already awkward, I might as well get the money part out of the way, she thought.

"So, uhm, it's $250," she said. "You can set the money there." She pointed at the dresser near the closet which would hopefully give Luke a clear shot of the guy's face. "Unless, you wanted something extra," she said.

Steve set the money down and looked her over.

"You mean like for more than just my dick inside your pussy?" he asked.

"Well, I'm happy to suck your cock," she said walking over to him and touching him on the arm, "and even lick your balls as well as for you putting your dick inside of me." She ran her hand up his arm. "But if you wanted something like...to fuck me in the ass..." she looked him in the eyes and batted her eyelashes.

"What about kissing?" he asked.

Izzy gasped a little, taken aback. She never even thought about kissing a stranger -- fucking one, sure, but kissing... that was even more intimate somehow. She looked at the guy, in what was probably his nicest set of clothes: a blue dress shirt with a mustard stain on the front and black cargo pants. She could see that the t-shirt under his dress shirt was a Captain America shield. She started to think he might not have ever kissed a girl before, and suddenly she wanted to make this special for him.

"Kiss me, Steve," she panted, her heart aching for how pathetic and scared he looked.

Steve looked down at the money in his hand, not sure whether he was about to be swindled somehow or something. Izzy knocked the money out of his hand and threw her arms around his neck.

"It's free," she whispered. "I just want to feel your lips on mine. I'm getting wet just thinking about you kissing me."

She realized that she really was wet. Not because she was expecting him to be a good kisser -- not at all. But because she felt...vulnerable with him, and that turned her on. Not to mention the fact that he might taste her brother's cum on her lips. Now that thought made her really wet.

She didn't wait for him, she stood on her tiptoes and put her mouth to his.

"Oh, Steve," she panted. He put his hands clumsily around her waist and started halfheartedly kissing her back. "Oh, YES, Steve!" she moaned.

She felt his cock swelling against her hip, and she pressed herself against it.

"Can I be your girlfriend tonight?" she asked, looking up at him with her face inches from his. "This is my first time, and I want it to be special, you know?"

She took his hand and pulled him over to the bed.

"I'm so glad you're my first, Steve. I really want this, and I'm just glad that it's a sweet guy like you."

The guy was completely in her thrall, mesmerized by her every move, her every word. She realized that she could work him like putty, that she could probably convince him to give her even more money, but she really didn't want to. She just loved how enraptured he was. It made her feel incredible to have a guy become literally speechless because of her.

"I"m so wet," she said, sitting back on the edge of the bed and touching her crotch. "And my nipples are getting hard. Can I show you?"

She didn't wait for him to respond, she just pulled her top off. The look in his eyes as he fixed on her breasts made her feel incredible. She let him drink her in a minute before she took his hands and lifted them to her tits. She arched her back, pushing herself into his hands.

"Oh god, your hands feel so good on my tits! It's making my pussy even wetter, Steve."

As he clumsily pawed at her tits, she unfastened her shorts and pushed them down. She spread her legs to show him the wet spot on her thong.

"Oh my god, I'm so wet!" she said, taking one of his hands and putting it right over her pussy. "Oh, fuck, Steve, my cunt is so wet for you!"

When he reached down into her panties on his own, it shocked her. His boldness made her smile.

"Do you want to finger my pussy, Steve? I'm so wet for you, and my little cunt feels so hot."

When he pushed a finger into her slit, she fell back on the bed and let him take over her body. There was nothing skillful about his touch, but she really did feel turned on to have a stranger groping between her labia. Her enthusiasm started out as an act of pity, but now she was really into it. She loved being able to give this guy the kind of experience that he'd probably only ever fantasized about.

"I...I want to fuck you, Izzy," he croaked.

"Yes!" she gasped, eager to feel his cock inside of her. "Show me your dick, Steve. I want to feel it inside of me."

When he pulled out his cock, she smiled, happy to see that he was pretty average. It wouldn't hurt, and it wouldn't get lost inside of her. She reached out and stroked it, feeling the pre-cum on his slit with her thumb and rubbing it over his head, making him gasp.

"Can we do it without a condom?" he asked. "I haven't ever fucked a girl before, and...I just want my first time to feel good."

She knew it was stupid. She knew better than to trust anything a john said to her. The website she'd signed up with warned all of the girls to always be safe. At the very least, she should probably ask for more money, since that was the whole reason for doing this, but...

"I'll pay you a little extra," he said, reaching into his back pocket.

Izzy put her hand on his to stop him.

"It's okay," she said.f

Her heart fluttered at the thrill of knowing that she was going to let a stranger cum inside of her pussy.

"And you don't have to pull out." She smiled as she guided his erection to her wet slit. "It's a first for both of us, so let's make it as special as possible."

As she lay there and felt him press his cock to her slit, she remembered that her little brother was watching and filming, and that this would be recorded forever.

That thought only made the scene better, and as she looked up into her first John's eyes, she watched his face transform into an "Ohhhh" as he buried himself inside of her. She wasn't the tightest girl by any means, but she wasn't loose either, and the sensation clearly was the best thing Steven had ever felt.

To her own surprise, and pleasure, the sensation it stimulated inside her own cunt was incredible. She was easily an 8, or maybe even a 9, and Steven was a 4, but it didn't matter at that moment. And if it did, it only made the scene hotter.

Instincts took over for the tech nerd who lived at home with his parents even though he was 29. His rhythm was terrible, and as he began to slide in and out of Izzy's cunt his moans blew his breath directly into her face, but she found it surprisingly endearing. She was his first, and his unprotected cock was steadily leaking pre-cum into her as he neared his first orgasm inside a woman.

that realization only made Izzy wetter, and her hands ran over his back as her own back arched beneath him, pushing her breasts towards his face.

"Oh my gosh Steven! yes! Yessssss! I can feel your cock inside me, unprotected, our skin touching each other's skin! How does my pussy feel? Is it what you hoped for baby?"

"Y-YES!" he gasped, experiencing sensory overload as the gorgeous woman beneath him moaned, and writhed and gripped his cock with her incredible cunt!

"Izzy! This is the best day of my life! I don't think I can hold on much longer! I'm so close! I'm going to cum in you! I'm going to cum inside of a woman! I...I....I'M AGHHHHHHH!"

The sight was unlike anything she'd ever seen before. It was so

awkward and funny looking, but the passion behind it, the truth, the realization that she'd just done something for him that he never could've imagined before.

She was so close as he bottomed out inside of her and began to ejaculate. She could feel the spurts spraying against her inside walls, and the realization that a total stranger had just cum inside of her was all it took.

She thrust her cunt up against his cock as it began to spasm. Her body writhed beneath his as she screamed out in an ecstasy she hadn't felt before. An orgasm rooted in depravity and risk and love rather than a random hookup with a stuck up guy.

"I'm CUMMING" she screamed, "I'm cumming on your cock Steven! I'm cumming on your big, fat cock that you just fucked my tight little cunt with!!!!"

As he collapsed on top of her, they both rested, their bodies pressed together, while they recuperated from the orgasm. It had been mind-blowing for both. But as he slowly recovered, any confidence that he'd gained apparently evaporated and he climbed off of her, self-conscious and covering himself with his underwear.

"T-thanks for that," he said as he pulled his shorts on. "I mean, for pretending. I....I have a lot of money. I mean my job pays well. I work in tech. W-would...would you still be working this week?"

Izzy leaned up, resting on one arm with the other propped on a knee, shamelessly exposing herself.

"I wasn't faking it, Steven," she said with a smile. "This was my first job. And I really did cum! That was so....real, with you. Plus, I hope I was your first, because you totally just sprayed cum inside me."

Her honestly made him smile, "Yeah...that was....that was the coolest thing I've ever done."

"Well, you have my phone number," she said as she climbed off the bed. "I don't know how long i'll be doing this, but...give me a call one way or another, and I'll be around for you."

Her words made him beam, and he was so speechless that he just stood there for a moment before walking to the door. "I...I will! T-thanks, Izzy! I'll call you soon!"

"Wait, Steven!" she called out as he put his hand on the doorknob. She jumped up out of the bed and ran to him. She threw her arms around his neck and kissed him. He put one hand around her waist and pulled her to him halfheartedly. She stood on her tiptoes, and pushed her tongue into his mouth.

As they made out for a second, she felt his cum start oozing from her pussy. She pressed her legs together. For some reason she wanted to keep it inside of her. It felt so special to have her first John's cum inside of her, but as she gave her all to the kiss, some more leaked out.

When she broke the kiss, she stepped back and spread her legs so that Steven could see what was dribbling down them.

"God, you put so much cum in my pussy," she said, wiping it up with her finger. She brought it to her mouth and sucked it with a moan as she looked him in the eye. "You taste delicious," she said. "Next time, I want to suck you first so that I can eat a whole load of your delicious cum. Then I want you to throw me down and fuck me, Baby."

She gave him a quick peck on the lips again. "Promise you won't fuck any other girls, and I'll let you ride me bareback every time, okay?"

He nodded nervously.

"Call me," she said, stepping back to let him leave.

When the door closed, she threw herself back on the bed. When the closet door opened, she had forgotten for a moment that Luke was still there. When she looked up at him, her legs were spread wide and glistening with both Steven's cum and hers. She bit her lip and smiled at her brother.

"Well, how was I?" she asked.

"Fucking shit, Sis!" was all he could say.

She smiled and giggled.

"That was so fun. I wonder when..." but her phone answered the question she was about to ask.

"Wow, there's a guy in the lobby right now. I better get cleaned up," she said, looking at her phone. She texted to ask the guy to give her 15 minutes and then come up.

Luke was standing right in front of her, taking pictures of her leaking pussy.

"Luke, I have to get cleaned," she said.

"You at that," her brother said, zooming in to snap more pictures. "What does it taste like?"

"You've never tasted yours?" she asked.

He shook his head and looked at her like she was crazy.

"Eat me," she said on a whim, teasing him.

"Fuck you," he shot back.

"Come on, I know you want to taste my pussy. It's not just his cum down there, it's mine too."

Luke shook his head, but she could see the curiosity in his face. She spread her legs wider and reached out and put her hand on his head. He didn't resist much as she pushed her brother's face down to her sloppy cunt.

"Oh my god, Luke, I want you to eat a stranger's cum out of me," she panted, realizing that she was really turned on by this. "It's so fucked up, but I want it so bad."

She pushed his face right down into her twat, feeling her lips part as his tongue slide between them.

"Yes! Oh god, Luke! Yes!"

She thought he would pull away, but the fact that he just kept licking made her even more excited.

"I love that you're just as dirty as I am," she said, pushing her pussy up to meet his mouth. She let go of his head, but he kept licking her. She lay back, her body tingling at the sensations her brother was bringing to her cunt. Then she felt his tongue slide over her clit, and she gasped.

"GOD! YEAH! Right there. Make me cum again, Luke! I want to cum on your face!"

They were both lost in the sensation of her building orgasm when the knock came at the door, making them sober up immediately. She pushed Luke away and scrambled to get her clothes back on. He ran to the closet, and she saw that his dick was out at half mast. Once she was dressed, she picked up the money Steven gave her and threw the wad into the closet after her brother and then shut the door. She took a second to look in the mirror to fluff out her hair before she opened the door.

"Hi, come on in," she said sweetly to the older gentleman when she opened the door. "Just set your money on the dresser there, and tell me what you want to do to me."

The man was an older gentleman, with a bald head, a thick bushy mustache, a large belly, and thick glasses.

As he looked her over, he was more than impressed. he wasn't expecting her to actually be the girl in the pictures.

"Well I gotta say. Missy, you do not disappoint. I can't count the number of hookers I've gone to who turned out to be 5's when they advertised as 10's."

Izzy smiled at the compliment, "Well, I aim to please. I'm Izzy by the way," she said, offering her hand.

"Nice to meet you, Izzy. I'm Hank. So, your ad said anything's on the table, huh?"

"That's right," she replied, enjoying his laid back confidence. "You fuck whores a lot?"

"Oh yeah," he said, enjoying her laid back confidence as well. "My wife passed years ago and I retired with millions. I figure you can't take money to the grave with you, so I might as well spend it fucking girl's a third of my age."

Izzy smiled as she removed her top and then her shorts, standing there confidently with her hands on her hips, totally nude. "Well Hank, I'm happy to take your money and let you do whatever you want with me."

He nodded, whistling lowly as he took in the incredible sight. "I don't think I've ever seen a whore as fine as you, Izzy. But a lot of them say anything's on the table, but don't really mean it."

"I guess I should ask what you want then, huh?"

Hank looked her over another moment, then nodded. "Alright, I've got a granddaughter about your age. Blonde like you too. She's a stupid little cunt though, and her mama won't let me discipline her. So I want you to be my granddaughter. I'm going to spank your sexy little ass," he said, his breathing getting deeper as he confessed his fetish. "Then I want to raw dog you in the ass. No lubrication, no

condoms. Then I want to pull out and make you suck me clean before I finish in your cunt. Now I know what you're thinking. A) that man's a sick creep, and B) there's no way you're letting me raw dog you when I've fucked so many hookers. I understand that, but like I said, I'm a wealthy man."

He reached into his pants and pulled out 8 more $100 bills."That's a total of $1050. Sure, there's a risk, and sure it'll hurt a little, but you wanna make money, don't ya Izzy?"

She'd expected to have some weird requests, but his was definitely more detailed and more odd than she'd expected. Besides, the thought of his cock, which had been buried inside of hundreds of whores going into her screamed at her that it was dangerous.

But...it was over $1,000. She bit her lip, then sighed and put her hands on her hips in a faux perturbed motion.

"God, Granddaddy, fineeeee. Just don't tell mom and dad I stole their money and I'll let you do what you want," she said, slipping into character and drawing a smile from Hank.

"Don't get sassy with me, Jenny," he said as he took her by the waist and turned her around.

So I'm Jenny now, Izzy mused, excited at how rough his hands were as he took her hand manhandled her body. Then he pushed her over at the waist, making her fall face-first onto the bed with her feet on the floor. The position made her ass stick up, and she felt deliciously exposed to the stranger pervert.

"Granddaddy!" she gasped.

"Hush now, Jenny. I'm going to have to spank you for that money you stole.

"But my bottom is bare. It's going to hurt so much," she whined, enjoying playing the role.

"Oh, I'm going to make sure of that, Jenny. It's going to hurt like fire."

Hank rubbed his hand on her bare ass, caressing it for a moment. Izzy got lost in the pleasantness of the sensation. When his hand pulled away, she missed it, yearning to be touched more. But when the hand returned, it was to smack her hard on the ass.

"OW!" she cried out.

In her mind, she had been imagining something playful, but this was worse than her parents had ever done back when they spanked her. It made her eyes well up. She started to try to get up, but she felt Hank's hand in the middle of her back pushing her back down.

"Don't you dare try to get out of this, you little hussy," he said, and he brought his hand down on her again.

Izzy squirmed, but she was held firmly in place by the heavy man. There was not getting out of this. She scrunched up her wet eyes, getting ready for the next strike, knowing that there was no escape. She thought she was ready until she felt the sting.

"OWW owwwowww," she whimpered. "It hurts so much."

She was breaking character. She just wanted to get away from the pain, but then she remembered that there was no escape.

"Granddaddy," she whimpered, hoping to play on his fetish, but it just thrilled him to hear her sad little voice say that word.

He smacked her again and again. Izzy resigned herself, crying out at the pain but knowing that she had to endure it and afraid that the ass fucking was going to be even worse.

"You deserve this, bitch," he said calmly. "And when I'm done here, I'm going to hurt your ass in a whole new way.

As she lay there, held down, crying, she felt him caress her thighs before raising his hand to strike her again. It became a pattern of slight pleasure followed by intense pain. She loved it. She hated it. But mostly, she hated how much she loved it. The feel of his strong hand pushing her down, the power in his strikes, making her ass jiggle, then the loving touches.

Though there were still tears in her eyes, there was a touch of arousal this time as she whimpered the name, "Granddaddy."

"You know this is what you deserve, you dumb cunt. Say it!"

Izzy opened her mouth, but nothing came out. Then he struck her again, and she cried out.

"I deserve it! I deserve it, Granddaddy! I'm just a dumb cunt!"

"Yes," he growled. "And you know what happens to cunts? They get fucked."

She felt his hands move to her hips. He lifted her ass more. The pain in her skin was incredible. It felt like her skin was on fire. Then she felt something new as he started pushing his cock into her asshole.

It felt like it was stretching, ripping her. The pain was shocking and intense. She tried to squirm away, but he was holding onto her hip too tightly.

"NO!" she found herself screaming, rejecting his attempt to penetrate her. "Please!"

"You're going to take this, you dumb shit. We agreed. Didn't we? Say it!"

She thought about the obscene amount of money sitting on the dresser and nodded her head as tears pushed past her squinted shut eyes.

"That's a good cunt," he said. "Now spread your cheeks for me so I can rape your pretty little asshole, bitch."

Resigned, Izzy reached around and pulled her ass cheeks apart for the man.

"Oh, Jenny," he grunted. "You look so fresh and cute. I'm going to love ruining you. But I want to hear you beg me for it."

Izzy shook her head, but then a slap across the back of her skull made her stop. She opened her mouth.

"Please..." she started.

"Please what?"

"Please rape my ass, Granddaddy," she cried.

"Why?"

"Because I'm just a stupid cunt, and it's what I deserve."

"Yes," he moaned, and he pushed into her.

Izzy screamed and grunted as she felt him splitting her open. It hurt like nothing else ever had. She wanted it to stop, but as her words -- her own words -- rang around in her head, she found herself pushing back against him, helping him rape her, hurt her.

"I deserve to hurt for you," she cried. "I'm just so stupid and worthless and..." she sobbed, but somehow it felt good to cry like that, felt refreshing.

She opened her eyes and looked over her shoulder at the man, and this time, she begged him with sincerity.

"Please, Granddaddy. I want to be your dumb bitch. I want to hurt for you. Rape me."

In the closet, Luke watched, both scared for his sister and aroused in a way he'd never imagined. He'd heard of rape porn, but he'd never actually seen it. Yet he knew his sister well enough to know that she was literally being raped, even if she had resigned herself to it and begun to embrace it.

On the bed, Hank obliged Izzy's request and hammered his cock into her dry ass. He watched her eyes go wide with lust and pain and fear she sacrificed her butt for a wad of cash.

With his cock thoroughly buried inside her, he pulled swiftly out then hammered forward again, beginning a brutal rhythm that slammed Izzy into the bed over and over again.

She'd never felt like such a slut...such a useless whore in her life, and she loved it. She knew it was wrong, she knew this was dangerous, but she was loving how it made her feel.

As she saw a brief amount of movement in the closet, she suddenly remembered her little brother was watching, and she couldn't begin to imagine what he must be thinking.

But the thought of it, the thought of him witnessing her rape was so delicious hot, and as Hank hammered into her ass, she let out a loud moan/groan.

"Yessss granddaddy! Rape me! Rape my stupid little asshole like I deserve! I'm just a dumb cunt thief! AGHHH YESSSSS!"

The performance and dedication by the whore was more than Hank had ever expected, and for the first time he was actually getting his money's worth! But he also knew he was getting close, and knew it was time for part three.

As he suddenly stopped pounding and pulled out of her ass with a loud "plop", Izzy realized what time it was. Hank stepped back and had a seat on the bed, incidentally giving Luke a perfect view as he spread his legs and held his erect cock up.

"Alright you dumb little twat, now that your ass is burning nice and good, it's time for

you to suck it clean."

Izzy slowly hobbled over to where he was sitting, barely able to walk as it felt as if she'd been split in to by a baseball bat. But this was a different sort of degradation, she knew, as she got on her knees between his legs; knowing that her little brother would be watching and filming, and hopefully masturbating to her suffering.

In the closet, Luke nearly moaned. He lowered the camera to his cock as he stroked, filming himself for a moment before looking back up at his sister's situation.

As she got down on her knees, she could smell her ass on the man's cock. Despite the pain -- or maybe because of it -- she was actually kind of eager to suffer a new degradation for this man.

When he grabbed her head by a handful of her hair, she felt the bliss of her surrender overtake her. And when he simply said, "Open," she did, opening her mouth to receive the man's filthy dick.

She closed her lips around his shaft and let him push it all the way into her mouth.

I'm his whore, she mused. I'm just a dirty whore on her knees sucking ass of a stranger's cock...Because that's what I deserve.

As he held her head and started fucking her mouth, she realized that her pussy was drenched. She loved the way this man took control of her, doing exactly what he wanted. It was so different than her last experience.

Steven was a boy, but Hank is a man, she thought, realizing the difference. She loved both experiences, but there was a blissful kind of freedom in letting this stranger do whatever he wanted to her body. She realized that she wanted him to have her in any way that made him happy, and as she looked up into his eyes, she saw that he was indeed very happy.

"You're a filthy bitch, aren't you, Jenny?"

She nodded, her eyes still wet from the pain of being spanked and fucked.

"You love getting treated like a dirty whore, don't you?"

She found herself smiling. She did. She truly did. She nodded and sucked even harder.

"Yes, get me there, Jenny. I'm going to cum soon. But not until I put it in your cunt. I'm going to cum in that worthless pussy of yours."

The word "worthless" washed over her, and she found herself wanting to try harder for this man. She realized that his rough hands were not the only means he had of controlling her.

He pulled his dick out of her mouth and slapped her on the cheek with it. She found herself trying to get it back in her mouth. She was hungry for it.

"Are you ready for me to fuck your pussy, girl?"

She looked up at him and smiled.

"Yes, Granddaddy! I want it so bad."

"Even though I'm going to cum in you with no condom?"

The thought of it thrilled her so much that she realized that she was close to cumming just from the idea.

"YES!" she cried. "Please! Fuck my cunt, Granddaddy! I want to feel your hot cum in me!"

He lifted her up onto the bed before she knew what was happening. She was on her back, looking up that the man who had raped her ass, and now she was holding her thighs open for him to fuck her pussy. When he pushed into her, she felt so complete, so whole.

He held her down as he started pounding her cunt. It was so vigorous, so rough. His legs and testicles hit her sore ass, but she savored the pain, grateful that he wasn't done hurting her.

"Fuck my worthless pussy, Granddaddy!" she cried, nearing her climax already.

He didn't answer. He just grabbed her by the hair. She looked up at him, smiling. Then she saw his lips pucker. But instead of the kiss that she expected, he spit in h er face. It shocked her startled her. It was so disgusting and vile, and... she loved it. She opened her mouth, silently begging him to do it again.

He did. And when she felt the blast of spittle and tasted it on her tongue, she closed her mouth and swallowed it, and then her body was wracked by the strongest orgasm of her life.

"YESSS!!!!! GRANDDADDY!!!"

She cried. She smiled at him, and then she felt it, felt his cum spraying into her. It was perfect. It was lovely. It was what she deserved.

"FUUUCK!" she heard. But it wasn't Hank that spoke. She saw the closet door fall open, and Luke tumbled out onto the floor with the camera in one hand and

his dick in the other.

Hank's balls emptied their entire contents inside of her. It had been such a build-up, such an intense fuck, that he was spraying more than he had in months.

As Hank watched the boy fall out of the closet, he saw the camera, and at first thought that they may have been trying to blackmail him, but then he knew the more likely reason....safety.

"Luke!" Izzy half moaned half gasped as she came.

"Well well well, who do we have here," Hank said as he pulled out of Izzy, his softening cock hanging limp and covered in a mix of juices.

"He's....my brother," Izzy admitted.

"You're on brother?" Hank asked with a deviant smile. "Well it's a pleasure to meet you, young man," he said as he walked over and offered his hand.

Luke was stunned, but once again his quick wit lept into action. He started to offer his jerking hand, but hesitated.

"No no, it's okay," Hank said, " Man's gotta jerk, right?"

Luke nodded as he glanced at Izzy, "Yes sir."

"So that's your sister. She's pretty amazing, huh? You like jerking off to her?"

"Yes sir, she's...she's amazing." Luke admitted, giving Izzy a sweet smile.

"Did you like watching me rape her?" he asked.

Luke blushed, but finally nodded, "Yeah. It was amazing! I've never seen a woman scream and beg like that."

Hank laughed, eyeing the boy up and down.

"Well now I can see why you were willing to be my granddaughter," he said to Izzy. "But I've got another proposal. I'll pay you each $100 if you'll eat my cum out of your sister's cunt."

Luke hesitated and looked at Izzy. She knew that danger she'd taken letting him cum in her, and now he wanted her brother to eat it out of her. He had no idea Luke had already done it once, and they needed the money.

"He'll do it," Izzy said. "Eat Granddaddy's cum out of me, Baby Brother."

Hank's cock twitched again just hearing her say that, and he groaned as he watched Luke drop to his knees between his sister's legs.

Steven's load had been big, but Hank's load was massive. As Luke lowered his mouth to her pussy, he could smell the rank stench of the old man's cum.

"Smell that?" Hank said, "That's four cups of coffee and two packs of cigarettes a day. It used to make my wife gag."

Izzy bit her lip as her brother looked up at her, but she felt the strongest feeling of love as he buried his face in her cunt and began to lap at the cum and slurp it up.

The sight was something that Hank had never imagined he'd see. Watching the boy, with his cute butt and hard cock eating his sister's cunt was so hot.

"Yeahhhh, that's it boy, get it all. Eat her cunt good!"

It was so gross, so revolting, but hearing his sister's moan, tasting her cunt, eating another man's cum....it was too much.

As he lapped up the last of it, he suddenly stood up and leapt on top of his sister.

"Izzzzzzzy!" he moaned as he slid into her cunt and began to ejaculate.

"Holy shit!" Hank said as he held the camera up, recording the boy cumming in his sister.

Rather than being mad, Izzy held her brother as he came, looking into the camera and moaning softly while Hank recorded.

As the orgasm subsided, he offered Luke another $100 to eat his own cum out of her, which he happily agreed to.

When they were all finished and the orgasms had run their course, Hank made a final offer.

"Let me buy this video off of you kids and I'll thrown in an extra $300."

"Well, that's our first blowjob and fuck," Izzy said. "But we can email you a copy of it."

"That works for me," Hank said with a laugh as he began to dress.

"But I tell you what. I don't know what you kids are working towards, but I know opportunities like you two don't happen very often. So if you want to make some more money, you should come out to my ranch," he said as he looked over Luke and ran a hand over his butt, giving it a squeeze before stroking his cock. "You've already eaten my cum, you might as well suck my dick too. And you," he said to Izzy, "You're one of a kind -- a whore that knows what she is. I know you'll do anything for money, and if you come out to my ranch, I'll make you do things that'll make you hate yourself until you die."

Izzy thought about the kind of money she could make. If it was anything like tonight, they might get the car paid off in just a week. But then she realized that, even though the Mustang was the reason she started this, it wasn't the reason that she was going to continue. Hank was right. She knew what she was. She was a whore.

"You have my number, Granddaddy," she said. "Text me the address. I...I..." she couldn't believe what she was about to say out loud. "...I just want to be your whore."

Hank gave her a wink and left the room. Luke sat down on the bed next to her. She wasn't sure how much they had earned tonight, but she bet it was enough to get the mechanic started on the car. And maybe she could offer the mechanic something that wasn't financial to get the ball rolling.

She looked over at Luke who was just flipping through the bills in his hand, not even counting them it seemed -- as if he was in a trance.

"I love you," she blurted out.

He smiled and turned toward her. "Love you too, Izzy," he muttered. She could see the fatigue on his face. It had probably been torture on him to have to stand there that whole time.

"No, Luke," she said taking ahold of his face and turning him to her. "I mean it, I love you."

She put her mouth on his and kissed him with the most sincere passion. He'd seen her acting tonight, and he knew that this wasn't that. This was real. This was them. This was love.

"Let's sleep here tonight," she said, pulling him down onto the bed. "We can get room service and then head home in the morning to get dress and take the car in. These two weeks are going to fly by."

As they lay in bed together, she snuggled up next to him. Her little brother put his arm around her, and it felt so good, so right. As her face rose and fell with the rhythm of his chest expanding with each breath, she drifted off to sleep.