Role Playing Sessions

As Cassandra pulled up to her parents farm home, it was a reunion that she'd been looking forward to for nearly a month. Before that, it was something she'd dreaded.

Knowing how obsessed her little brother was with incestuous porn had been daunting at first, but now she was looking forward to testing his resolve...did he really want to fuck her?

As she stopped her car in their driveway, she was wearing a pair of jeans and an orange lace blouse when her brother burst out of the front door.

"CASS!" he screamed as he ran and nearly tackled her over as he wrapped her in a hug.

He felt her firm, lean body and large breasts pressed against his head.

Of all the porn he watched, and all the girls who'd eaten cum and done the most unimaginable things, his sister was the one he came to nearly every single night, and she was finally home!

Ever since Cassandra had borrowed his laptop, Isaac had been worried that he hadn't deleted his browser history before giving it to her. He had heard horror stories at school from his friends about their moms finding out what kind of sites they like to visit. But secretly, Isaac hoped that Cass would see it and be as turned on by it as he was.

It had been a revelation when he realized that he was not alone in lusting after a sibling. And finding tumblr site after site dedicated to people who wanted to fuck their own brothers and sisters had finally made him feel somewhat normal in his weirdness.

Regardless of whether she even noticed or not, Isaac had masturbated non-stop since Cass had borrowed his laptop, imagining her looking through the sites that made his three-inch dick hard and hoping that her pussy would get wet, too.

And here she was. The moment he saw her out the window, all of his fantasies faded into the back of his mind because the very sight of her was all that he cared about. He sprung out the door and threw his body around hers.

Her soft breasts pushed into his head as he wrapped his arms around the one person that mattered more to him than anyone else on earth. As he did, his cock started to harden against her leg. He could never bring himself to tell her how he felt about her, but he always enjoyed every moment of contact he had with her body. He would definitely be remembering this moment later as he stroked himself to a sticky conclusion later.

"I'm so glad you're home," he told her, looking up into her sweet eyes. He couldn't help himself, his hips involuntarily thrust into her leg just a bit as he looked at her. God, her body felt so good!

Cassie was reminded of a small dog in some ways as she felt her brother thrust against her. It was so adorable, and so wrong.

"I missed you too, Isaac!" she said as she squeezed him back, then knelt down. She was quite a bit taller, and it felt natural almost to treat him like a kid; he was 9 years younger than her after all.

"So, how's your summer been?" She asked, almost as if talking to a small boy.

While it was borderline patronizing, Isaac knew his sister well enough to know that wasn't her intent, and he was more than happy with the reward of being able to look at her cleavage.

"It's....it's been really fun," he said almost breathlessly. "It's great to have you home though!"

It was clear that he'd enjoyed the view, and his stuttering had been adorable.

"Well, we're going to have to hang out the whole summer, right? Do you still like hiking the trails behind the farm? I've been missing them like crazy!"

"You bet!" he said excitedly. "We should hike them tomorrow!"

"Definitely," Cass replied with a grin before leaning down and giving him a kiss on the cheek.

After dinner that night, and catching up with her parents, Cass and Isaac went to their rooms.

As he stroked himself, he softly moaned his sister's name until he came, spraying his own bed with cum but loving that he'd paid tribute to her once again.

The next morning they both slept in even after their father left for work. When they finally did wake up, both had the same idea. As they ate breakfast Cass grinned.

"So, ready to hit the trails?"

"Totally," Isaac replied. "Last one out the back door is a rotten egg!"

As childish as it was, the challenge sent both of them sprinting for their room; a 20 year old college student and an 11 year old boy.

Naturally Isaac was waiting on the back porch, laughing when his sister came out; but his laughter stopped almost immediately. She was only wearing a pair of her old, black cheer shorts which hugged her butt tightly, and a red sports bra with a pair of running shoes.

Cassie pretended like nothing was out of the ordinary as she saw her brother staring, almost speechless, and couldn't help laughing to herself.

"I guess i'm the rotten egg, huh?"

Isaac's eyes traveled up and down his sister's body, and his little dick immediately sprang to life. He wiggled in place, trying to get his cock into a more comfortable position without touching it and drawing attention.

"Huh, yeah, you're so...rotten" he replied to Cass, but his eyes said that she was anything but.

As they took off into the woods, Isaac was grateful for the parts of the trail that were too narrow to walk abreast so that he had to lag behind. The view of her ass in those shorts was so amazing. And as long as he was behind her, he could touch himself -- not enough to get true relief, of course, but enough to make himself dizzy with lust.

"I think you've kind of outgrown your cheer shorts," he said, when they stopped by the creek to dip their feet in and cool off.

"What do you mean?" Cass asked, turning her hips to and fro as she looked down at herself. She was secretly glad he'd noticed the fact that her shorts were too small for her anymore.

"They don't even come up to your hip bone," he said, reaching over and tracing the line of her pelvic bone with a finger, wet from the creek.

She laughed as he traced the line along her body, enjoying the touch.

"Oh, that? That's nothing. You should see the girls at our college gym. I don't think any of their shorts hide the top of their butt cracks."

"I know how gross you think that'd probably be," she said, teasing him as she flicked some water his way.

The thought of college girls, especially her, wearing such small shorts was a dream come true and he shook his head.

"It doesn't sound that bad."

As they continued their hike, Cass found herself loving the narrow portions of the trail as well, and especially the parts that required them to climb small rocky ledges.

As she'd lift herself up, she knew the view from behind had to be amazing, and she'd often times have to turn around and pull Isaac up, giving him a nice view of her pressed cleavage.

The more he stared at her body, the more worked up he felt. He'd never gone this long getting this worked up without doing something to relieve himself of the tension. He wanted to badly to just reach into his shorts and rub it out, but he was so terrified of her seeing.

But the building testosterone in his system was making him feel bolder. He was touching her body more, swatting her on the ass if she took too long getting over a log across the trail, reaching into her cleavage to lift up her necklace and look at it as they stopped to take a breath.

He felt like his body was burning with fever the more worked up he got. If not for the tension, though, he probably would have never had the courage to ask her. But with her body heat radiating out next to him as they sat in the shade on a rock side by side, he simply asked.

"So, did my laptop come in handy for your paper? I hope you didn't delete any of my bookmarks. There were some Minecraft tutorials I need, and...some other stuff."

Feeling her little brother growing bolder and bolder told Cassie that his young urges were running the risk of losing control.

As he'd slap her ass, or touch her breasts reaching into play with her necklace, the touch felt so forbidden yet so enjoyable.

As they reached the top of one peak, the summer heat had begun to increase and both were sweating, even with such little clothing on.

Taking shelter in the rock shade, and providing a relatively flat surface, it was the perfect spot for a rest.

The question, however, caught her off guard. It was bold, but she grinned as she could sense both a hint of apprehension, and a bit of hope.

"Hmmm, your computer?" She asked as if thinking.

"Ohhhh, yeah! Thanks for letting me borrow it by the way, it saved me from getting a 0 on one of my finals. But, I didn't delete any of your bookmarks...although I wouldn't recommend letting mom borrow your computer. I'm not sure she'd be too thrilled with that one brother and sister video...."

Isaac's heart nearly stopped with anticipation. "T-the brother sister one?"

"Yeah," Cassie said as she walked over to the edge of the rock face nonchalantly. "You know, the one with the bet on their final test? She lost and had to let him fuck her in the butt."

Isaac's pulse practically raced, "O-oh...that one, yeah....what did you think of it?"

Cass grinned and shrugged. "I don't know. I think it would be cool if we were that close. I mean, how fun would it be if we made bets like that?"

Isaac couldn't believe his ears. His little prick was aching with need, and his balls were so blue they felt like they were about to burst.

"Yeah, th-that would be cool," he stammered, looking over her body as he thought about how close he wanted to be to her.

"I mean, we're already so close," she said, leaning over to give him a look down her cleavage. "You've been touching my body and staring at me all day, and strangely, instead of making me feel grossed out at my perv little brother, it actually makes me feel closer to you."

Isaac laughed nervously as she got closer. It almost felt like she *wanted* him to look at her chest. He couldn't help himself. He felt compelled to look whether she wanted it or not.

"Me too," he breathed, feeling her body heat even more. "Wh-what kind of bets would we make if w-we were like that brother and sister?"

"Hmmm," she said as she leaned back and thought about it.

She laughed as she glanced around. "I bet that you won't scream as loud as you can that you love to suck dick."

"What?" he laughed, completely embarrassed by her proposal. "Come on, really?"

When she didn't relent and just kept twisting back and forth to show off her breasts, he asked, "Okay, so if I do, what do I get?"

She laughed, "If you do, I'll go butt naked for the rest of the hike. Buuuuut, if I have to, then I should get a bet as well."

"Okay," he said, anxious to see her body. "So, I bet...that...you won't..." he started blushing even as he thought about it. "Oh my god, you're going to hate me," he said, burying his face in his hands. He'd seen it in a porno, and he wanted so badly to try it right now with her. "I bet you won't let me pee on your tits."

The deviancy of it shocked even Cass but she laughed.

"OOOOOH! Gross, sicko!" she said, but clearly didn't mean it.

"Fine, if I let you do that...what do I get?"

He couldn't believe she was actually considering it. He'd drunk so much water on the hike that he really had to go anyway. If she was willing to do that for him, with him, then he'd be willing to let her do...anything actually.

He looked up at her and met her eyes for the first time since they'd been out. He felt strangely close to her all of the sudden, like having these secret desires between them made everything so much more special.

"You name it, Cass," he gasped.

Cass's heart raced as she considered it. This was so much different than she'd expected, but so much better in a way. His perviness was shining through, and the mundane sexual acts people typically did first seemed to be afterthoughts. She wanted to continue that...to make his first time something unique and extreme.

As she thought about it, the answer came to her mind. The heat of the day, trapped in her tight shorts was what she wanted.

She bit her lip as she grinned a little.

"Okay, I'll let you pee on my tits, but you have to eat my ass afterwards."

"Oh, fuck you're so nasty, Cass!" he joked, but the thought of doing something so dirty with her made him incredibly hard.

With that, he stood up, cupped his hands around his mouth and screamed, "MY NAME IS ISAAC JACOBS, AND I LOVE TO SUCK DICKS!!!"

As the woods echoed his proclamation of homosexuality, he grinned at her lustily, anxious to see her body on display for him like he'd always wanted.

"Take 'em off, Sis," he said, his hand unconsciously reaching into his shorts.

"Oh my gosh, you actually did it!" she said laughing, sounding both shocked and proud.

"Fiiiiine," she said shaking her head, pretending to do it reluctantly. But her wink and grin as she watched him reach into his shorts betrayed her true feelings.

Gripping her top, she lifted it up quickly, bringing her large breasts with it before they slipped out, falling back to her chest and jiggling slightly; her large, dark nipples hardening in the warm summer air out of excitement.

"Just to make it interesting," she said with a laugh as she threw the top off the side of the peak, watching it fall down the leaves-strewn mountainside.

Pushing her bottoms down next, she stepped out of them, and tossed them as well before turning to her little brother. Her heart raced as she watched his eyes; feeling their hungry stares and she knew that she was exposing herself to an eleven year old boy who was her brother.

She let him get a good view before she stepped closer and dropped to her knees, putting her hands on her hips.

"Ok, perv....I'm ready."

"Oh my god, Cass," he gasped, looking down at her as she looked up at him. "They're even prettier than I ever imagined. A-and I imagined them a lot!"

He couldn't believe she'd just tossed her clothes over the bluff. She was naked now, truly and completely naked before him with no chance of going back.

As he pulled his shorts down to free his throbbing cock, he couldn't help it. He just started stroking it as he looked at her body, at her face, at her beautiful eyes looking up at her. He was already so pent up from staring at her through the hike, he knew he was close to the point of no return already.

"Oh god, oh fuck, oh Cassie!" he moaned as she jacked off to her beautifully toned body. "I know we agreed to pee, but first I...I just...You're so pretty that...I have to...I need to...OH FUCK!!"

His little cock sprayed out a volley of semen at her face. Rope after rope of runny, hot cum shooting out at his sister like his cock was a water pistol.

"You're so fucking pretty," he moaned as he continued to jack himself, shooting his load at her. He stepped closer, aiming his little prick right at her lips, degrading her with his semen and his complete disregard for her as anything but a cumrag. As he squeezed out his last few drops, he rubbed his softening cock on her cheeks, her lips, her chin. "So pretty."

When he realized what he'd done, he felt horrified at himself.

"Oh, god, I'm sorry, Cass," he said, stepping back.

But then the rest of his body's nature took over, and his bladder now had reign. He shot a spray of golden piss at her. Some of it hit her face before he came to and directed it at her tits.

"Ohhhhhh, fuck," he moaned in pleasure, releasing his stream at her body, spraying it back and forth between her two mounds. "Ohhh, yesssss."

The experience was something more incredible than Cass had ever hoped for. The look of absolute lust and need in her little brother's eyes and moans as he'd started to cum on her had been exactly what she'd wanted all month.

She'd wanted to be there for him, to help him in a way that only she could, and she finally had....she'd been his cum-rag, the face that he shot his load on, the girl who let him give his first facial.

"Ohhh fuck," she moaned. "Don't be sorry, Isaac; it's perfectly natural. Cum all over my face."

As he started to pull away though, the second phase began.

Cass reached up, pulling her hair out of the way as her little brother began to urinate on her.

It was something she'd never imagined, yet felt so right. To be peed on by an eleven-year-old; to have him spray his urine all over her tits, was the ultimate in degradation and love.

She was glad, too, that he clearly had to go as it gave her time to enjoy it.

"Mmmmm, yesss! Pee on my tits, Isaac! Pee all over your big sister's tits!"

Suddenly though, a thought came to her mind. If he was going to eat her ass, she should at least let him pee in her mouth.

"Do you want me to drink it?"

Without a moment's hesitation, Isaac aimed his cock as his sister's mouth.

"Yes, drink it!" he moaned.

Even at age eleven, he'd seen so many horrible, degrading videos of men treating women like nothing more than objects. He'd been told by the guidance counselor at school that real sex was nothing like pornography, but that guy was clearly wrong because here was his big sister, opening up her cum stained lips to let him piss in her mouth.

"Drink every drop that's left, Cass," he moaned. "I'm going to eat your ass so hard."

He looked into her eyes as he pissed in her mouth. It seemed like she was smiling at him with just her eyes as she opened wide and let him fill her. He looked down to see the golden liquid pooling on her tongue, sloshing around her teeth. And then her lips came together, and she smiled as she swallowed, and she opened up for more.

The girls in the piss whore videos were always so ugly -- older women from eastern European countries. He never in his life that a pretty girl would willingly let a guy piss in her mouth.

"You're like my urinal right now," he said, giggling.

His stream slowed down. He squeezed his pelvic floor muscle, shooting another squirt out then another. And then he was done.

She'd finally done it, she realized....she'd drank pee! The liquid was disgusting, and foul, and bitter and it left a horrible taste in her mouth, but it didn't matter....she'd drank her little brother's pee!

She finally rested back on her heels as she sighed.

"Oh my GOSH! That was like one of the hottest things I've ever done, Isaac! I was like your toilet!"

"So, on a scale of 1-10, how good was I as your urinal?" she laughed.

But as she smiled up at him, she felt her pulse race as she was ready for her turn. She'd humiliated herself before him, now she wanted to do the same to her 11 year old little brother.

She leaned forward, getting on all fours as she turned towards him, presenting her ass in the air.

"This is so hot, Isaac," she said with a moan. "Now eat my asshole, little brother!"

"You're a 10, Cassie," he gasped, getting on his knees behind her.

He was mesmerized by the sight of her beautiful ass. He'd been trying to imagine it all day, undressing her with his eyes, but now that she was actually nude before him, it was more incredible than he could have ever imagined.

"Oh my god, ohmygodohmygod," he gasped as he leaned in toward her beautiful backside. "It's so pretty. Everything about you is just so..."

Cassandra couldn't take it anymore. He'd cum on her face, and she'd drunk his piss. She was ready to degrade him herself. She reached around behind and pushed his face right into her crack.

"Lick, little brother," she said, giggling. "Remember the deal?"

His a face was shoved up in her crack. He stuck out his tongue obediently, but he couldn't quite find the hole. He wanted to find the hole. He wanted to taste his sister's behind and feel more filthy and nasty than anything he'd seen on the internet yet. He reached up and spread her cheeks apart, and his face fell right onto her puckered anus.

"Oh god," he whimpered as he slipped his tongue out and licked her sphincter. "Oh shit," he moaned as he smelled and tasted her sweaty, dark aroma. "Oh fuck," he cried as she shoved him harder against herself, and he licked her clean.

"Push your tongue into me. Push it into the hole," she demanded.

He knew he would do anything for her. He *wanted* to do anything for her. It seemed like there was no way possible to feel closer to his sister than right now with his tongue against her backside.

"Ohhhhh," he moaned as he stiffened his tongue and shoved it in. It tasted even more pungent now, and he loved it. He wanted it. He started thrusting his tongue into her, saliva dripping from his tongue as he fucked her asshole with it.

The proof of how much he loved it was that his little cock was getting hard again, and he let go of one of her ass cheeks to stroke himself as he tongue fucked her anus.

The feeling was unlike anything she'd ever had. Feeling his tongue licking her had been one thing, but to feel him sliding his tongue inside her, knowing he was tasting the inside of her ass, was an entirely new level of depravity, and he was only 11!

As she looked between her legs, she saw him stroking his small cock, and she knew what she wanted. She'd degraded him enough, now she wanted them to fuck.

As she suddenly pushed his head back, pulling his tongue out of her ass, she turned towards him.

"OH MY GOSH, ISAAC! I love you so much! I can't believe you did that...it's so....gross! Thank you so much!"

She wrapped him in a hug, feeling his little sweaty t-shirt absorbing the piss and cum. As she broke the hug, she lifted his shirt up, revealing his thin frame, looking so young and small with his tiny cock extending erect in front of him.

"Isaac....let's fuck. I want to be your first. We can do it any way you want, any position. I just want to be your first fuck....I want to have sex with you."

"Lay down," he told her.

He knew what he wanted. The first time he'd seen it on a porn video, it was so dirty and wrong and perfect. He knew he wanted it so bad, but girls supposedly never did it.

As Cass lay back on the rock, she spread her legs to him. He looked down at her wet pussy. It was shaved, so clean and pretty. "Like a flower," he said, looking up and smiling at her.

"I love you too, Cass," he said. leaning in. "I've wanted you for so long. Your body is so pretty and perfect and hot and sexy."

One hand reached up to grope a breast as the other hand guided his cock to its mark. She felt him then, pushing -- not into her sloppy wet pussy, but into her tight ass, lubricated only by his saliva.

"In the videos I watch, the girls who let guys fuck them in the ass -- they always look so pretty. And their pussies look even prettier as the cock goes in and out of her asshole."

He looked up from the hole he was violating to smile at her. His face contorted with pleasure as he felt her tight walls envelop him.

"It's so warm," he gasped. "And tight. And look, your pussy is so pretty not being used. You're the perfect girl, Cass."

He whimpered as he started thrusting in and out of her ass.

"God, you feel amazing!" he moaned. "You're my first. My first sex. And you're so dirty you're letting me fuck your ass. My own sister's ass!"

It was only right that after the depraved sex they'd had, that he would lose his virginity in her ass.

She'd had sex in her ass before, but those men had been large and it had hurt, but with her little brother, who'd already lubricated her ass with his tongue, it felt like little more than a mild discomfort, as if she was being fingered.

She loved it; she loved the sensation of being butt fucked by her own little brother's tiny cock; she loved that she could squeeze her hole tighter to make it better for him; she loved that she was being butt fucked by an eleven year old.

"Mmmmmmm, oh fuck, Isaac! Yesssssss. Fuck my butt, little brother! Your cock feels so nice and big in my tight ass!"

She ran her hands over his chest, feeling how flat and thin he was. She looked into his eyes, smiling back at him as he sodomized her.

"Fuckkkkk," she moaned. "I love being butt fucked by you, Isaac! I'm such a pedophile"

Isaac was in heaven. It felt better than anything ever had that he had done to himself. Not only was her hole tight and warm, but her whole body was on display to him including her dripping pussy, her full breasts, her tight abs, and her gorgeous face covered in his cum.

"I love you, Cass," he moaned. "I love you so much! Everything about you is just...perfect... oh OH. OH FUCK! YES!!"

He grabbed her hips and thrust harder, wildly slamming his pelvis against the meat of her ass cheeks as he rammed into his sister over and over, building toward his climax.

"CASSIE! OH FUCK YES, CAAAASSIEEEEEEE!!!"

He collapsed on top of her, spent as his hips continued to buckle, and his cock sprayed its contents into her bowels.

"I fucking love you," he panted, his head resting on her soft breast.

Cassandra put her hand on Isaac's head. She loved the feel of his body pressing against her.

"You lost your cherry in my ass," she giggled. "I'm afraid I might have ruined you for normal girls who don't put out so easy and pretty much never give up their ass."

Isaac looked up into his sister's eyes from where he lay against her breast.

"Then I guess you'll just have to keep taking care of me, Sis. Won't you?"