Kinky Sister Kinky Brother

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

She was so sexy and sexually comfortable with herself...it made him feel like he could be too.

"Fuck, yeah, that was, wow, that was really fucking good, Maddie." He said. He ran his hands down his body as he stretched a little on the bed.

She fell back and slipped the strapon panties off her legs as she reached over into her sex toy box again. She looked at him with a raised eyebrow.

"Wow brother, you really take cock like a champ, ya know that?" She said to him as she marveled at how sexy her brother was to her in that moment, having discovered some of his kinkiest secrets. She thought for a moment as she considered where to go next.

"Wanna try this?" Maddie asked him as she held up the 12 inch-long double-dildo she had grabbed from the box. Maddox breathed in deeply. It was purple and bulbous and it looked fatter than the dildo she had just used to take his anal cherry. It was a godly two-way cock for sure.

"Yes." He said to her, "Fucking absolutely." He was nervous but excited and far too turned on to stop now. She had completely pushed past any of his doubts.

"Okay!" She said excitedly. She took out the toy and covered both ends in copious amounts of lube.

"How do you wanna do this?" Maddox asked. She seemed to be driving the whole show now.

"Well brother, there's a lot of ways we could do this. We could scissor each other, or face each other laying down but that's harder to thrust that way...or we could go butt to butt which would allow us both to take it hard...or...there's my favorite way." She said with another naughty smile.

"What's your favorite way?" Maddox asked.

"I'll show you." Maddie had him lay down on his stomach but she propped one of her pillows under his waist which popped his ass up for her. Then she put both of her legs to the outsides of his and faced away from him.

Maddox watched her in the closet mirror again as she sat up and placed the dildo into his ass. He gasped as she pushed the larger toy into his loosened butt. It was bigger and wider, and he moaned loudly from the new size stretching him.

She pushed the toy as far in as she could get it, a full six inches before it was too much for him to take. He stopped her when she had gotten it this far in. He was breathing in and out slowly, trying to calm himself. Maddie pressed the toy now up to her own sexy rosebud. Her asshole opened up for the toy and she wiggled her body down so that it would slowly enter her ass.

She moaned loudly as she allowed her ass to open up with the lubricant of the toy as she pushed her body down further to her brother's butt.

It was fine that Maddox could only take six inches.

She could take eight.

He realized this when he felt his sister's sexy buns pressed against into his own ass as she sat up now and allowed the toy to fully fill them both. Maddie brought her hands down to twist her nipples and play with them as she rocked back and forth in a gentle backwards cowgirl on top of her brother's stretched cheeks. She was fully impaling them both on the two-way monster and the siblings moaned loudly together as she began to bounce up and down on the toy a little harder. The six inches mostly stayed pushed into Maddox but the rest of the length was used to push in an out of Maddie. She bounced her ass back against her brother's butt and they shared the naughtiest ass fucking together. It was so erotic. These two kinky siblings completely melted into each other's naughty fantasyland as their backsides jiggled together with the toy that connected them each time they smacked together.

Maddie began to really bounce her ass hard now back against Maddox's butt and she couldn't believe it but she began to feel Maddox arching his ass up further to take a more dedicated role in this dicking. The toy began to push a little further into him and soon he had seven inches inside his ass. And soon he had eight.

"Mmmmm, Maddox I fucking love you...you're doing so good babyyyyy!" She moaned to her brother as they both relished every second of this incredible experience. She gyrated her hips on top of him and moaned in the naughtiest way on the cock as it filled her.

Maddox once again was rock hard and he was so glad that he'd gone a week without jacking off before this night. What a happy coincidence for all of the built up cum he had to keep him going.

After Maddie had butt bounced her brother for a while she told him to turn over. Maddox turned over with the toy still inside of him and then Maddie reinserted the toy into her and now they faced one another on the bed as they shared the double dildo with their legs fully spread eagle against each other so that their thighs were pressed together. They propped themselves up on their elbows and slowly grinded their crotches together as Maddie worked on getting more of the toy into her brother.

"Mmm fuck, Maddie," Maddox moaned as he felt the toy pushing further in. "It's so fucking good."

"Yeah brother, you take it so good. Take that big cock like you love it." Maddie said to him, and he complied.

The siblings bounced against each other as the toy came in and out of them over and over again. Their moans and giggles and groans and gasps were a symphony of every thing that made dirty sex the best kind of sex.

Before long Maddox was close again, and Maddie was close too.

They were able to time it so they came almost exactly together. Maddox's cum drooled out and down his cock as he jacked his seed onto his sister's pussy and stomach. She was rubbing herself with his sperm now and was soon able to achieve her own satisfying orgasm. And soon they were both laying back and breathing in and out deeply as they recovered, the toy still lodged in both of their asses.

Maddie slowly pulled it out of her ass and Maddox did the same as they threw it off to the side of the bed.

She curled up next to him now and they shared a sweet kiss as she snuggled close.

"Wow...that was pretty fucking sexy." She said as her lips lazily kissed his neck as she nuzzled into him.

"Yeah sis, holy fuck, that was stupidly hot." He said.

"So is this like...is this how we're gonna be around each other now?" Maddie wondered out loud.

"Well, I mean...I had a lot of fun, and I think you did too...and I don't even know if we'd really be able to pretend that didn't just happen." He said, stroking a hand through a sweaty hair that had stuck to her face.

"No, I like it...I don't want to stop, trust me...it's just weird to think about." She mused. She was still horny. Maddox was still horny.

"I want to fuck you again, tonight." He said, as he thought about having his sister bend over for him. He wanted to take her from behind. He wanted to fuck her ass, too.

"Good, cuz I want you fuck me again." She said, and she leaned up and kissed his neck again and lightly nibbled his ear now.

They were both still fairly revved up by each other.

"What else do you want? Now that we both know each other's kinkiest secrets and fantasies...what do you want to do with me?" She said to him, prodding the dirty depths of his brain.

"I want to see you with another girl," Maddox said, thinking of the video he'd seen on her porn page.

"Mmm, I knew you were gonna say that!" She said, but she was excited by the idea. She wanted her brother to see her with a girl too.

"What if me and the girl both dominated you, though?" Maddie asked as her fingers traced down his cock playfully. "What if we both wore strap-ons and fucked you all night? Would you be into that?" She asked. She felt his cock pulse against her fingers a little when she said that. Dirty boy, she thought lasciviously, but she loved that her brother loved this idea.

"Yeah, I'd totally be into that...I'd be a slut for you and another girl in a heartbeat...fuck, that's so fucking hot to think about." Maddox said, as he closed his eyes and enjoyed the way his sister's hand felt as she lightly played with him.

"Yeah, I think it would be really sexy to see you with a cock filling you from both sides." She said, and she felt his cock bounce a little again when she said this, each of her words having their intended affect on her kinky little brother.

"Ugh...fuck, yeah, that sounds really sexy." She kissed his neck and the bottom of his chin and his cheek. She kissed his closed eyelid and his the small of his nose. These were sweet, intimate kisses between two lovers that were finding just how inclined they were towards each other's individual proclivities.

"And maybe if we play with a girl, we could also play with another guy?" She said, and now Maddox was starting to get hard again.

"Mmmm, yeah." He said in a softer voice as he listened to every delicious word.

"Yeah...maybe I could invite my fuck buddy from my psychology class over and you and I could suck on his cock together...would you like that?" Maddie asked, and Maddox noticed that her voice was becoming sexier, more seductive.

"Mmmmhmm," Maddox answered.

"What was that Maddox? Will you suck on a cock for your sister? Will you do that for me baby?" She asked him, and he nodded and moaned a needy yes.

"What else will you do?" Maddie asked him.

"Anything you want me to." He responded.

"Anything I want?" Maddie prodded.

"Anything you want." He said again.

"Would you let him fuck your ass? Would you do that for me? Take your first cock while I watched? Would you let a guy actually stick his penis inside of you?" She oozed sexual expertise in every word.

"Yeahhhh." Maddox moaned.

"Yeah baby?" Maddie asked again.

"Yessss." Maddox moaned more. His hips gyrated a little against her and Maddie could tell he was thinking about having a cock in his ass. He wanted it.

"Mmmm, that would be so fucking hot to just watch you being fucked...I'd fucking love that—I'd literally be on cloud nine if I got to watch that happen."

"I want to do that for you." Maddox said, " I want to be a little slut for you." The words were stripped of all pretention or male toxicity. Maddox was kinky, and Maddie was kinky, and they had found each other and were leading each other on now.

"Sit up on the edge of the bed...let's watch some more porn together." She said. She went and grabbed her bong and the two of them took another large hit of her high-quality hybrid.

She crawled back on the bed after setting the bong down and crawled in behind Maddox as she put her arms over his shoulders and worked her controller as she navigated over to another favorite porn Tumblr. She pulled up one of her favorite videos. Three attractive college-aged boys were in bed together and as she played the video they quickly began to get down to business.

Maddox was sitting with his legs hanging off the bed and Maddie put her legs outside of his as she sat behind him and watched the video. Her hands came around to play with his cock and chest.

"I love this video. The boy in the middle takes cock the way I want you to take cock." She said and Maddox moaned at that thought.

The boy in the middle was indeed being dominated. He was soon spread out over the bed with a cock in his mouth and his ass. Maddie jacked Maddox off as they watched the sexy gay porn together.

"Mmmm, fuckkkk that's hot." Maddox said, and he meant it. He was very turned on that his sister wanted him to be taken in a similar way.

"So would you ever do that? Let two guys fuck you at once?" She asked truly curious.

"I dunno...I think I need to try one cock first and see how I do." Maddox said, turned on, but also slightly frightened by the idea.

"I think that's probably reasonable...you might end up not liking it...then again, you clearly liked it when I pounded you with my strapon...so something tells me you'd take two cocks like a dog in heat." She said to her brother, her hand stroking him slowly up and down while they watched. She could feel his vibrations when she'd describe each new deviant desire.

"So...I wasn't joking before...would you really be willing to get fucked by my friend from class?" She asked him as they played.

Maddox paused for a moment to truly think about it, but he couldn't deny that he wanted it. The more he thought about it the more it turned him on. He wanted to have sex with a guy.

"Yeah sis, I want to...it's turning me on a lot just thinking about it." The porn changed scenes and now the boy was taking both cocks in his ass at once. It was dirty and the boy in the middle was completely submissive to them.

"Do you want me to text him right now?" She asked, and she eyed her phone on the stand beside her bed.

"Yes."

"Okay, She leaned back and reached over for her phone and then pulled herself back up to him with her legs still around his.

She punched some things into her phone as Maddox nervously awaited to see what she was saying.

"His name is Todd by the way," she said, not telling him what she was saying.

"Okay...so, this is a guy you hook up with occasionally?"

"Yeah...I met him in class...but there's something you should probably know about him." She said, a little deviousness creeping into her voice.

"Yeah, what's that?" Maddox asked.

"He's a little older than us." She said.

"Oh? How much older?" Maddox pressed her.

"Like...he's in his forties." She said.

Maddox was confused at that. "Wait, I thought you said you met him in class?"

"I did. He's my favorite teacher." She said, and Maddox gasped as he looked at his sister.

"YOU'RE FUCKING YOUR TEACHER?" He asked her. She smiled back at her brother. All the cards really were out on the table now.

"Well, I mean, yes. Yes I am." She said it almost proudly now. She didn't mind her brother knowing what a slut she was. They were being completely open with each other at this point.

"How did that happen?!?!" Maddox asked as her hand came back around to grab his cock as she stared at the screen of her phone. She looked up at him.

"Wellll...I sat in the front of his class because he's a fairly good looking guy—'Silver Fox' I believe is the appropriate terminology...like...okay you know the actor from that 'Justified' show you liked so much." Maddie tried to remember the name, even as her hand continued to stroke Maddox's cock.

"Timothy Olyphant?" Maddox said, immediately knowing whom she meant. It had been one of his favorites a few years back.

"Yeah, the lead guy. He kinda looks like that." She said, and once again, she thought she felt her brother's penis jump a little.

"Hmmm, he's pretty good looking I guess." Maddox said, and Maddie shook her head yes as he looked back at her. He turned to face her now as the ignored porno finished climactically in the background of their conversation.

"Well anyway, I would sit in the front because he was very nice to look at during particularly boring lectures about psychology and there was one day that I noticed his rather large cock running down his fitted pair of slacks that he wore to class." Maddox was so amazed by every new detail of his sister's sex life.

"Okay..." He spurred her on as she jacked him off slowly. He had his hands on her breasts now as he pulled on her nipples gently.

"So I kind of started to have these constant fantasies about him and that lead me to start wearing shorter and shorter skirts to his class. And there was one day after the break that the class was super empty and I was actually the only one in the front row so I went to the bathroom and took my panties off and then I slowly worked my skirt up during the class. No one behind me could see me cuz it's one of those stadium seating style classrooms where all the seats are close together with the little desks.

I got my skirt all the way up past my thighs and then I purposely opened my legs for him hoping he would see me."

"Whoa...fucking amazing...you're so fucking sexy, sis." Maddox said to his little minx of a sister.

"I know." She said naughtily as she shrugged her shoulders proudly.

"So what happened next? Did he see you?" Maddox had become fully hard again she told this story.

"Yeah, I forced him to see me when I raised my hand to ask a question towards the end of the class. I was completely scooted forward and my legs were wide enough that it looked like it could've been an accident, but I was definitely showing my pussy to him. The second he saw me raising my hand to ask my question his eyes went down and locked onto my spread legs."

"Wow...what did he do?" Maddox asked her now.

"He took a second longer than normal to process what I was saying, and his answer was kind of confusing and all over the place, but no one else seemed to notice."

"So...what then?" Maddox was on pins and needles. This was too hot.

"He asked me to stay behind after class when I started packing up my things. He locked the door after everyone was gone, then he walked over to my desk and stood there in front of me. We just looked at each other for a moment not saying anything. Then I bit my lip on purpose for him to give him my best slutty face, and he started to undo his belt."

Maddox had closed his eyes as she told him this sordid story. He couldn't believe how naughty his own sister was. It was exhilarating.

"Then you sucked on his cock?" Maddox asked.

"Yeah, he undid his belt and then zipped down his pants and took his cock out. He had a nice fat cock, like a juicy seven inches...I was so fucking turned on. I sucked on him while leaning over my desk. Then he pulled me over to the front of the room and bent me over his own desk and lifted my skirt up and he just fucked me right there without a condom and...after like five, really hard minutes of pounding me he pulled out and came all over my ass. It's probably one of the hottest things that has ever happened to me."

As she finished her story her phone buzzed in her lap again.

"What did you text him?" Maddox asked.

"I asked him if he was free to have some fun, and he said that he was. I told him that my super-kinky guy friend was over and that we were both looking for a nice cock to share. I told him you're a virgin but that you were very interested."

Maddox couldn't believe how ballsy she was. But it only turned him on more.

"Does he play with guys?" Maddox asked the obvious question.

"Yeah...he's bisexual actually." She said to him and her brother's cock throbbed again in her fingers even as her own body ached with the possibility of further fantasies fulfilled.

"How did you find that out?" Maddox wanted to know everything.

"I came to his office during a gap in classes one day because I wanted to suck on his cock and while I was going down on him I asked him if he had any other students that he fucked...and he told me yes...a guy in one of his morning classes with a particularly tight ass." Maddox throttled at this revelation.

"So I pressed him for more details and he told me that he likes fucking both girls and guys. He's a very dominant guy. He gets off on being in charge." As she said this she could feel her brother's pre-cum as it started to lather the outside of his cock.

"Fuck...that's...wow." Maddox was feeling a lot of things at once. She took her hand off of his cock and lightly rubbed the skin of his perineum with her fingertips. She was driving him crazy with lust.

"So...do you want me to invite him over? He lives close. And he says he'd be happy to give you your first real cock." Maddie could see the way her brother's cock was throbbing as her fingers dragged across the little hairs of his crack.

"Yeah, I want to. I'm scared kinda, but I'm also really turned on."

"I know you are. So you're gonna let him fuck you, yeah? You're gonna give him your ass for me?" She was completely taking over her brother's mind now.

"Yeah...fuck...yes, I will." He said. And she knew he was serious.