Kinky Sister Kinky Brother Ch. 02

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Maddie's brother gets a lesson from her professor.
8.8k words
4.73
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Part 2 of the 2 part series

Updated 06/08/2023
Created 04/21/2018
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All characters in this story are over the age of 18. The following tale includes gay, bisexual, and incestuous themes. Traveling vanilla sex salesmen need not apply.

*****

Maddox followed his sister's sexy booty as she pulled him towards her apartment bathroom. The two siblings were naked and thoroughly ravaged from their surprising night of kinky discovery.

Maddie hadn't expected to spend her evening enjoying some of her nastiest fantasies with her very own brother, but some physical compasses have a habit of pointing people to their true north.

She started the hot stream of the shower as she placed the lingerie down on the counter next to her sink. Then she turned to enjoy another hit of the weed as the smoke coiled up through the colorful bong.

Maddox watched as she pulled him close by the waist and opened his mouth. He breathed in deeply as she pushed the smoke from her mouth into his own. The bathroom quickly fogged over with all sorts of subtext. Everything was hot, so to speak.

Maddie put her hair up so she wouldn't get it wet. Besides, she had other parts of her body she preferred to keep that way.

The two siblings slipped into the warm stream and enjoyed the hot water as it washed away the combination of the day's suntan lotion, sweat, and sexual juices.

Maddie pulled Maddox in and kissed him sweetly in the stream of the water and they giggled together against each other

"I still can't fucking believe we're doing this," Maddox said.

"I know," Maddie grinned cutely, "I can't believe my brother turned out to be just as much of a kinky slut as I am!" They smiled against each other and lazily dragged their lips over each other's mouths.

Maddox watched his sister grab a razor from the shelf and her shaving cream. She turned her brother around and squirted the white cream all over his butt as she had him bend over slightly. Maddox closed his eyes and enjoyed the warm running down his head and back as he felt his sister's hands spreading the lather all over his ass cheeks.

She slowly began to shave the hair off his ass so he was super soft and smooth. She took her time making his hole as soft and accessible as hers was. It was unexpectedly sexy.

"Don't worry slutty brother, I'm just making your booty nice and sexy for Mr. Hendricks' cock. He likes his sluts to be smooth and shaven." Maddox felt his whole body buzz as she said the name of her teacher while she shaved him—he would be his teacher soon enough, he knew.

Maddox was turned on and nervous and terrified all at once. Maddie's actual college professor was on his way over at that very moment. Maddox was going to get fucked in the ass by a real cock for the first time—a real cock connected to a real man's body. He thought of what Maddie had said about him—about how he looked like the actor Timothy Olyphant. He shuddered a little as he thought of the idea of that actor sliding his cock into his ass. What was it going to be like? He was scared, but he also very much wanted to know the answer to all of these questions. He was going to get fucked in the ass while his sister watched. It was so kinky and sudden and fantastic and he wanted to be dedicated in his presence for the main event.

Maddie meanwhile was straddling the outside of one of her brother's legs as she shaved him. Her pussy lightly grinded against him as her mind drifted to Mr. Hendricks' big cock. She gently and carefully made her brother's ass as soft as the skin on a Chivette of the Week (She would know, she'd had numerous anonymous booty shots posted to the frat-boy website after she'd submitted herself for various contests and collections). Her devious mind devoured images of her own brother being filled up by the cock that she'd spent her last semester mastering.

When she had fully removed the hair on his buns she grabbed a bottle of her expensive body wash and squired it all over the top of his ass as she covered her hands in the soap. Maddox closed his eyes and purred as her hands scrubbed his butt and his crack and down to his balls. She still had him bending slightly into the spray as he braced himself on the wall during her attentions.

Maddie lovingly massaged her brother's growing cock and ran her soapy digits up and down his hole making sure to completely clean him to her satisfaction. Maddox loved every time he felt her fingers ice skating past his sensitive taint. She massaged his perineal raphe and Maddox didn't even know that's what it was called but he moaned with a muffled sound that could've been those very words if you heard them in passing.

"Wash me." She said suddenly, and he was warped out of his sexually meditative trance that she had placed him in. He grabbed Maddie's body wash as she stepped in front of him into the shower's spray. She also handed him her shower bath sponge. He drenched the thing in a giant glob of soap and replaced the bottle on the shelf as he stepped in close behind her.

Now it was Maddox's turn to wash his sister's sexy body. He took his time. They were fairly stoned and the heat filling up the bathroom made him feel like he had stepped into a kinky steam room where he still wasn't sure what in the hell was real life anymore. All he knew was that his hard cock was firmly pressed between's his sister's beautifully round rump as he covered her body in the foamy white, soap. Maddie loved the feeling of her brother's hard cock resting between her ass cheeks as he washed her.

She couldn't resist. She bent over further and allowed the cock to rub up and down against her hungry pussy lips as she shook her booty for him. Maddox easily slipped inside of her while he washed her but they weren't really fucking. She just wanted him inside of her, and he wanted to be inside of his sister. It was a closeness that they were enthralled by. They were so willingly slutty for each other. She leaned back and kissed him as his hands came around and massaged the soap over her firm breasts and hard nipples. She felt him pulse his cock inside her a little and her whole body sprouted goose bumps for him. It was all too much to handle. Her brother was inside of her pussy. Her own flesh and blood was rock hard in her garden and she wanted nothing more than to be filled up by his familial seed.

But for now it was a just a teasing foreplay as they got ready. After she was fully washed he pulled out of her with a playful plop. They turned the shower off and got out to towel off.

Maddie dried her brother carefully and then covered his body with her Clinique Body Butter. She wanted him to look and feel as deliciously soft and sexy as she was going to look and feel.

Maddox meanwhile was completely in her hands at this point. He didn't know where she was taking them exactly but he had no plans of objecting to whatever came next. Everything was so damn sexy and kinky that he couldn't have pulled the emergency stop cord even if he'd wanted to.

There was no safe word.

After she'd repeated the application of her moisturizing butter on her own creamy sex-dream of a body, Maddox watched her grab for the stack of lingerie she'd grabbed on their way in.

She started with her own chosen set—a yellow and lilac sheer lingerie set that included sexy suspenders which clipped to a pair of Champagne stockings. The bra and thong were sheer other than little lilac firework accents that exploded over the sheer yellow fabric. There were three lilac bows that ran up the front of her body—the one at the top of her thong just below her belly button, another just above her button where her hemmed suspender belt hugged her slim waist and then lastly the tiny bow in between her breasts on the pretty yellow bra trimmed bra. Her nipples puffed out dark through the see-through material where they were flanked by drifting petals and other accents of lavender color. The tights hugged her curvy legs and Maddox had never seen his sister look so damn sexy in his entire life. She looked like a girl out of a high def porn video wearing a set of lingerie that would make him cum far before the fucking even started. She smiled at him as she struck a pose and showed off her booty. She had Kelly Kapowski booty and she knew it.

"So sexy," he said, and she kissed him. Then Maddie grabbed for the other lingerie.

She grabbed a darker blue thong and had Maddox step into them. The front pouch was silky soft and barely held his hard-on in, but the back was a different story. Maddox realized right away that this was a bikini thong. The G-string of the thong went tightly through his crack and turned him on as it pressed against his eager hole—the underwear was small on him and so it held his balls and ass tightly. He shuddered again. Then she grabbed a pair of black hold-ups with a very fine fishnet pattern with a single black seem running up the back of each leg as they ran up to a solid black belt around his upper thighs.

Maddox allowed Maddie to work the hold-ups up each of his legs and now he was wearing a pair of his sister's sexy underwear and a pair of her hold-ups and his pre-cum oozed into the panties at the implications of what all of this meant. He had never crossdressed before—never been sissified like this. This was all shatteringly new.

He sat on edge the of the tub as Maddie fixed her make-up and then she pulled him over to the sink and gave his own face some barely recognizable rouge. The she very subtly applied a little eye-shadow and liner to each of his eyes to define his features. You could hardly tell he had make-up on. She was just giving his face a little come-fuck-me color. Her own makeup was a much more seductive shadow that matched the lilac of her lingerie. She curled her hair in waves beside her face. She used a sexy, pink skin-toned lipstick and then kissed Maddox as she dabbed the color onto his own lips.

And then she sprayed some of her perfume on her wrists, applying it to her neck and chest. And then she did the same thing to Maddox's body, making sure to drift some of the perfume down to her box, and then Maddox felt her spray the scent against his g-stringed ass as she rubbed the spray into each of his cheeks and under the string of the panties.

She turned him to the mirror where she stood behind him.

"Well don't you just look like the sexiest little cockslut, brother," She said to him in a voice that would've made Aunt Jemima jealous it was so syrupy sexy.

And that's when they heard the knock on the door.

"You ready to be a total slut with your sister?" She asked him. And of course, the outline of his boner practically wrapping around his leg told all the secrets he couldn't hope to hide.

Maddie padded out of the bathroom holding Maddox's hand as he followed behind her. She opened the door to her apartment and there stood her professor, dressed in a pair of slimming slacks and a simple, tailored white button up shirt. Maddox immediately understood the comparison. He did look sort of look like Timophy Olyphant. He was tall, muscular—a streak of gray went across the front of his hair which he wore slightly messy but still coifed.

He smiled at Maddie as he drank them both in.

"Hello Mr. Hendricks," Maddie said, and Maddox instantly realized the character voice she was already affecting. But it wasn't fake. It was unavoidable. He was a very sexy man. He was a dominant looking man—like he had just stepped out of a championship-winning Rugby match to go and collect his fuck-prizes. And Maddie and Maddox were both expected to be at the bottom of his cum scrum.

He was certainly scrumptious. Maddie may have adding 'diddily' to that 'umptious', but that's only because he had already stepped forward and pushed his fingers into her sexy lingerie bottoms where he was rubbing her pussy even as he stared at Maddox like a wolf observing a weakened sheep from a nearby tree-line.

"So, is this my virgin cockslut for the night?" He said, as his fat fingers entered Maddie. She gasped as she leaned her head against his muscular chest as she enjoyed being fingered like she was in trouble.

"Yessss," she moaned against him, and he hooked her g-spot like an experienced fisherman.

"Yes what, Ms. Ackerman?"

"Yessss Teacher, this is your cockslut." Maddie moaned as she gazed at her brother. Her legs felt a little week as she said the word 'Teacher' out loud. It was her favorite thing about this particular lover.

Maddox's mouth felt very dry as Mr. Hendricks' eyes panned over his body. It was so strange to be dressed in his sister's slutty lingerie for another man. He had never done anything like this before but he was so fucking turned on.

"So, what has your sexy boy-toy here done with cock before?" Mr. Hendricks asked as he kept his slow fingering pace going inside of Maddie's pussy. She leaned against him and stared back at her own nervous brother.

"He hasn't done anything with a real cock Teacher, but he's very desperate to learn," she said, and Maddox knew she was reading his mind. They were the same kinky person, and she was guiding him into this experience like a sexual Sherpa on Anal Mountain.

Mr. Hendricks pulled his fingers out of Maddie and closed the gap between him and Maddox. He put his large hand around Maddox's neck in a firm grip. He wasn't choking him, but Maddox instantly understood who was in charge. He slipped his fingers covered in Maddie's juices into his mouth. Maddox immediately began to suck on the man's digits as she gulped at the hand around his windpipe.

"Is that true? Do you want to be taught how to be a slut for a real cock?" Mr. Hendricks smelled like the cigar he'd been smoking at the wedding he was attending across town when he received the text earlier that night from Maddie. He had no problem ghosting on the friends-of-friends event to have his dick worshipped by the promise of two willingly submissive sluts.

"Yes," Maddox said as the fingers were pulled out of his mouth. He was so fucking nervous he felt like he could faint against him.

"Yes, Teacher," Mr. Hendricks corrected him.

"Yes...Teacher." Maddox said it and felt his cock throb as the word left his mouth for the first time. His first cock belonged to a very dominant top. His first cock belonged to a Teacher with long-established sexual tenure.

"Ms. Ackerman why don't you go pour us some whiskey shots from that bottle I brought over last time," he said as she followed his instructions immediately. Maddie went to the kitchen and opened up cupboard. She grabbed three tumblers and poured the three of them a shot of the high-end bourbon he'd gifted her on his last visit. She watched as Mr. Hendricks walked over to the dining room table where he pulled out a chair to sit facing them.

She brought over the shots and they all quickly downed them together. Her pussy was squirming wet as she saw her teacher's dick inflated along the fitted slacks he was wearing.

"So, what is our slut's name?" Mr. Hendricks asked as they all enjoyed the smooth burn of the whiskey.

"This is Maddox," Maddie said as she walked back over to her brother and kissed him where they stood now in front of Mr. Hendricks. Maddox melted into his sister as she made out with him now and took his shot glass away to set it on the table. Maddox realized what was happening. They were putting on a show for Mr. Hendricks now—a slutty, enticing little moment. At some point she had started the music on her phone and some sexy R&B had started filling the room from her Spotify. She was actually grinding against her brother's body and now they were both dancing. It was strange to be dancing for another man, but as the weed and alcohol all intertwined together in his brain, he slowly started to melt into this character Maddie clearly was grooming him to be. They were both sluts. They were both a couple of hungry cock sluts and they were putting on a sexy show for the man seated in the chair in front of them. Maddox closed his eyes and grinded against his sister in the soft lingerie they both had on.

She was so sexy. Everything was so goddamned sexy.

"Mmmm, Ms. Ackerman, why don't you teach Maddox how to suck on a cock?" Maddie turned to look at Mr. Hendricks and bit her bottom lip. She was so excited by this instruction. She pulled Maddox down to his knees and they crawled up together in between Mr. Hendricks' legs.

Maddie massaged her hands up and down his muscular redwood thighs—ugh, he was just such a specimen of a man. He seemed to have an added tree-ring marking every time he had made her pussy wetter than it had ever been. Now she was on her knees between her teacher's legs with her very own slutty brother, and now they were undoing his belt together and pulling his zipper down. They worked in tandem to pull his pants off and then did the same to his boxer-briefs.

What flopped out in front of them was the type of phallus that would've made Andy Warhol proud—a Clockwork Orange-sized manhood worthy of any sculptor's overtime hours. Mr. Hendricks had one of those veiny humungo-cocks that hypnotized you in the pulsing magnetism of its phantasmagoric tallboy can aesthetics.

A drop of vanilla yogurt pre-cum sat perched on his storm-trooper helmet head's slit and Maddie grabbed the base of his cock and the back of her brother's head and pushed him forward towards his first taste of slut-cream.

"You never forget your first taste of a Dom's cum, Maddox. Lick it off with your tongue for me." She said it in a confident way that left no other shortcuts or reroutes. Maddox leaned forward as he felt his sister's fingers massaging the back of his head through his hair and he licked his tongue out along the rock-hard helmet as the cream lathered across the middle of his tongue and slowly dissolved into his taste-buds. And from that point forward he knew there would be no going back. He was a cock-sucking slut now.

Maddie moaned as she watched her brother's mouth touch another cock for the first time. Mr. Hendricks didn't know this was her brother—for all he knew this was just some slut Maddie was molding for her own enjoyment. He knew how kinky his favorite student was. He knew she was loving this.

He enjoyed the wet tongue on his large member and then he was even more surprised as he watched the nervous boy lick his cock all the way up his cock from the very base to the very tip.

"Good job slut, now let's lick his shaft slowly at first to show our teacher how much we appreciate his length," Maddie said, as she joined her brother with their tongues smothering the eight inches of piping that rose before them like the Tower of Babel—that's how it made them both feel at least—unable to communicate through anything but their own moans which escaped from their mouths as their minds appreciated the sheer impressiveness of what Mr. Hendricks had jutting out from his body.

At some point Maddie brought her lips up to kiss her brother and she grabbed the cock and brought it over to point directly into Maddox's mouth.

"Open your mouth and breath through your nose only," she whispered to him, and Maddox felt her push his head down onto the cock for the first time. Even though she had given him specific directions he still felt himself gag when the cock was about three inches in. It was a very large cock. She pulled it out with a small amount of saliva that escaped Maddox's mouth.

"It's okay baby, that's expected, just keep trying to control your breathing as the cock goes further down your throat." She pushed him back down. Maddox did as Maddie told him and he began to get better at getting the fat width further into his mouth. It was so fucking sexy to have a big cock in his mouth. His own cock was probing against his tight triangle of his panties as Maddie pushed gently on the back of his head and he breathed out of his nose like a Yoga exercise.