Taboo Academy Ch. 01

"I just don't get why I have to wear such a weird outfit," Kaden whined, "I'm a boy for chrissakes!"

"Exactly all the more reason to wear it. Now be a good boy and cooperate."

Kaden, a lithe boy of a fresh eighteen, stood completely naked before his mother, Phoebe, who knelt before him in a loose bathrobe, holding a pair of pink, lacy panties for Kaden to wear.

"Taboo Academy has a strict dress code for first day students. Your sister wore it last year with no complaints. Now step into these," Phoebe said as she pulled the panties up her son's legs.

Kaden flushed as his cock steadily grew to half mast, bulging out the front of the underwear after his mother pulled them up his waist.

"This is a very prestigious, highly sought after school. To have both of my children go there is an absolute honor for our family. Now turn around."

"I know Mom," Kaden sighed as he turned his back to his mother, craning his neck to look at her as she fit the panties to his tiny, twink butt. She grabbed a handful of buttcheek and muttered 'so cute' to herself.

"It's just strange to be wearing this kind of stuff. Sorry, but it's gonna take a little bit to get used to this."

Phoebe stood up, her bathrobe slipping slightly and exposing her left nipple to her son. The bottom half of her robe also separated and showed off her pussy for a brief second. Kaden's cock grew to a nearly full erection and oozed out a bead of precum. Kaden was beat red.

"Lift your arms up," Phoebe said, as Kaden complied and she pulled a white crop top over his head. Kaden's cock twitched once more in his panties as his mother's breasts rubbed against his chest.

Phoebe stepped back to admonish her son with a loving, motherly grin on her face. Kaden smiled awkwardly and shifted in place as he cupped his hands around his crotch to hide his erection from his mom.

"Oh my goodness, you are so adorable! Girls, isn't he just precious?"

Just then, Kaden's older sister Jordyn, and her best friend/neighbor, Alyssa, walked into the bedroom, both in shocking states of undress. Kaden's cock erupted to a steel hard erection at the sight.

His sister was wearing only a tank top that clung to her waist, leaving her bare pussy and butt fully exposed, and was drinking what looked like a creamy white milkshake with a straw, and Alyssa was completely naked except for a pair of knee high blue and white striped socks.

Kaden half heartedly shielded his eyes, though he was in fact peeking at the nubile nude bodies in front of him, troubled by the fact that he was so enthralled by his sister's shaved pussy and bubble butt. Alyssa's thin form, with her tiny little titties and tight little ass, did nothing to help the matter. He was hard as a rock in the panties his mother put on him.

"Why the fuck are you guys naked?!" Kaden asked in shock, using both hands to cover his crotch.

"Now honey-" Phoebe began.

Jordyn cocked her hip to one side and slurped out of her milkshake,

"What? It's nothing you haven't seen before. We're just getting ready for school, like you," Jordyn then pulled off her tank top, exposing her perky little titties to her brother, mother, and best friend, then did a little naked curtsy. Phoebe's inner thighs grew moist at the sight as she smiled at her beautiful teenage daughter.

"You've seen me naked thousands of times little bro," Jordyn said with one hand on her hip. "Remember when Mom would have us take baths together?"

Kaden blushed at the mention of that in front of Alyssa.

"Yeah but that was like, 4 years ago!"

"Mom, remember when he would get boners in the bath with me?" Jordyn asked Phoebe, laughing. "And then he would lock himself in his room after you dried us off?"

"Hey!" Kaden began to defend himself, feeling embarrassed in front of Alyssa, who was checking out her little butt in Kaden's full length mirror, naked as could be.

"I remember sweetie," Phoebe said, adjusting Kaden's top and ruffling his hair affectionately, "but don't embarrass your little brother in front of Alyssa."

Alyssa, meanwhile, was spreading her ass cheeks and ogling her butthole in the mirror with an oblivious smile on her face.

Jordyn looked over her friend and smiled.

"See? She doesn't even know what's goin on."

"Oh no I'm listening, sorry I'm just in love with my booty," Alyssa said, pulling her hands away from her butt and walking back towards the three of them.

"I don't know how you couldn't be," Phoebe said, smiling warmly at Alyssa, the girl she's known as her daughter's best friend and their neighbor since she was a little girl.

"Aw thanks Ms. Bridgers," Alyssa blushed and beamed at Phoebe.

Kaden was both incredibly hard and incredibly confused.

"No it's OK Kaden, don't be embarrassed, Adam gets boners around me all the time. And I can't blame him, since I'm usually walking around in just my underwear."

The mental image of Alyssa casually walking around her family in her underwear made Kaden's cock frustratingly twitch.

"Weird, Adam's never mentioned that..." Kaden trailed off, still half heartedly hiding his crotch from his female onlookers.

"I'll just say this Kaden," Alyssa affectionately put her hand on Kaden's arm, "you're about to experience a whole new world, and me, Jordyn, Adam, your mom, your aunt, we'll all be here to help you with anything you need."

Kaden looked over at his sister, who playfully stuck her tongue out at him.

"Umm...thanks."

"Now," Alyssa said, turning to Jordyn and putting her hands on her hips. Kaden ogled her tight little butt once more, fighting against everything in him to rub his hard and drooling cock. "Speaking of little brothers getting horny over their big sisters-"

"Hey!" Kaden said

Alyssa cocked her head back at Kaden and playfully narrowed her eyes at him.

"I should get back over to my house and see how Adam's doing. He's probably just as confused as Kaden is."

"OK, I'll see you out front in a little bit," Jordyn cheerfully said.

Kaden then got a mental image of his friend Adam, also of a fresh, lithe eighteen, standing in panties before his equally sexy mom.

'Wait, not equally sexy, that implies I think my mom is sexy! Which she totally isn't, that's the woman who gave birth to me and breastfed me and read me bed time stories. And gave me baths until I was 14 and walks around the house in just a loose robe most mornings...Wait, snap out of it!' Kaden thought to himself as his cock throbbed and as he ogled his mom's gorgeous, full figure.

Alyssa went to walk out of the bedroom, and then remembered she was butt naked.

"Oh shit, I think I walked over naked last night! I don't have any clothes!"

Phoebe's motherly instinct kicked in and immediately rifled through Kaden's dresser and pulled out a pair of his tight boxer briefs.

"Here honey, take these," Phoebe said, "and Jordyn, give her that tank top you had on."

Jordyn rolled her eyes jokingly at her mother's motherly concern for Alyssa,.

"Yes mommy," Jordyn sighed out in a mock petulant tone, bending over and picking up her discarded tank top as Alyssa pulled Kaden's underwear over her legs.

"Don't give me that attitude," Phoebe jokingly pushed back, "I'm just making sure the poor girl doesn't have to walk next door all nakey."

"Thank you Ms. Bridgers," Alyssa said, playfully smiling at Jordyn who stuck her tongue out at her.

"Although," Phoebe said, "you're probably just gonna get naked as soon as you walk into your house, aren't you, you little exhibitionist."

Alyssa tilted her head and looked childishly off to the side, sticking out her tongue and putting her finger up to it.

"Hmmmm, maybe," she said, cocking her hip to one side and looking playfully sly.

"You sure you're OK with wearing my underwear?" Kaden asked, incredibly turned on by the unorthodox sight of Alyssa in his boxers and a tight tank top.

"Oh yeah it's totally fine, if it's fine with you," Alyssa said, "I wear my Dad's underwear all the time."

Just another bomb drop this morning Kaden had to process. It was only 8 AM.

"Oh...OK...cool," Kaden muttered, at this point just waiting for everyone to get out of his room so he could jerk off and blow a massive load of cum.

"Alright, see you guys in a little bit!" Alyssa said cheerfully, skipping down the stairs and out the front door, blissfully excited for her second year at Taboo Academy.

On that, Jordyn also exited to her bedroom, presumably to put some clothes on, leaving mother and son in the bedroom again.

Kaden sighed,

"So...what else is part of this outfit I gotta wear?"

"Well honey," Phoebe began, "and you'll look super cute in it: a skirt. Aaaand knee high socks."

"Jesus Christ, you got me dressing like a goddamn little schoolgirl!"

"Now honey, I said no complaining," Phoebe said, wagging her finger and looking her son in the eye. "You're gonna get used to all this in no time. Plus, the schoolgirl thing is only to identify students on their first day. And every next day of school, you'll get to lose one item of the outfit."

Kaden tilted his head in confusion.

Phoebe brushed the air with her hand,

"Aaah, I'll let the school explain it, now step into these socks baby."

As Kaden pulled on his socks, blue and white striped knee highs, just like Alyssa had on, he began,

"Like what the fuck even is Taboo Academy? I can't find any info on it online, nobody will give me a straight answer about anything!"

Phoebe stepped forward and put her hands reassuringly on her son's shoulders and looked him in the eye.

"Like I said honey, it's best you experience it without any misconceptions about it. I would never steer you in a direction where anything bad would happen to you. You'll come to realize very quickly that this is some of the most fun you'll ever have. Your sister and Alyssa love it, don't they? And Adam and plenty of kids you grew up with will be going with you, just as scared and confused as you are right now."

Kaden felt deeply cared for by his mother, and pulled her in for a hug.

"Thanks Mom, you always know how to set my mind at ease."

Phoebe rubbed her son's back affectionately up and down, resting her chin on his shoulder.

"Of course honey, you're gonna do great today," she said, her hand traveling further down and gripping her son's buttcheek. She then gave him a long, motherly kiss on the cheek.

As they separated, Phoebe's robe came slightly more untied, revealing the entirety of one of her breasts to her son.

Kaden's eyes immediately glanced down towards it, his steel hard erection almost ripping through his panties. He still stood with his hands covering his crotch. As he glanced up from his mom's breast they caught eye contact and both blushed, with Phoebe smiling awkwardly and muttering a cute little 'oops' as she tied her robe back up.

They stood in tense, nearly sexual silence for a few seconds before Kaden began,

"Um...Mom?"

"Yes dear?" Phoebe replied cheerfully, her voice full of eagerness.

"Could I have some privacy for a few minutes? There's something I need to take care of."

Phoebe put her hand on her hip and smiled knowingly at her son.

"Is it your erection? Do you need to masturbate?"

"What? Um, n-no," Kaden stammered.

Phoebe again walked closer to her son and grabbed his arms and slowly pulled them from their crotch hiding position.

"C'mon honey," Phoebe said, "you know you weren't hiding anything right? I mean, with a penis like yours' it's impossible to hide if it's hard!"

"Jesus Mom," Kaden said, "don't-don't talk about my penis."

"That penis came out of me, you know that right? I can talk about it if I want," Phoebe jokingly said in a mock-authoritative tone, lightening the mood.

Kaden laughed,

"True, true, it's just weird hearing you say penis."

Phoebe adopted a sing-songy voice and swayed from side to side, singing,

"Penis penis penis, my son's got a big penis!"

"Oh my God," Kaden rolled his eyes.

"Penis penis penis, I can see my son's penis!"

"Alright alright," Kaden laughed, weirdly turned on even more by his mom's silly antics. "Was I going to jer...masurbate? Yes, I was. I gotta get it out before school, especially if I'm wearing these little panties and a skirt. I can't walk outside with a bon...an erect penis."

"Well," Phoebe said, shifting in place and eyeing her beautiful son up and down, "why don't you let Mommy take care of it?"

Kaden squinted his eyes at his mother, really trying to understand what she just said to him.

"Let you take care of what?"

"Let Mommy," Phoebe began, looking off to one side bashfully and bouncing on her tippy toes, "in your words...masturbate your erect penis?"

Kaden's whole body quaked and shook. His cock throbbed and drooled precum in his panties. His own mother just asked if she could jerk him off. Such a hidden, carnal, taboo desire, all of a sudden unlocked in his brain. It was as if a dam of incestuous lust burst in his blood. He eyed his mother up and down, her tight body in that little robe, barely covering her C-cup breasts, the same breasts he sucked milk out of when he was a baby. Her shapely hips down to her pretty little feet. She was no voluptuous woman but she was no petite girl either. Her beautiful, beaming, almost childlike (still at 38 years old), face, smiling at him, showing off her dimples. Her shoulder length blonde hair. He wanted her. Kaden swallowed the spit that was watering in his mouth and gulped,

"You wanna...jerk me off?"

Phoebe got on her knees and crawled right over to Kaden, and then began clawing at his panties, all the while looking up at him with the most seductive but also motherly eyes.

"Yeah, let Mommy make you feel better."

Kaden flushed and was practically shaking with desire. He wanted his mother to feel his cock.

"Um...OK, Mom," Kaden whimpered.

As she pulled off his panties Kaden's cock sprang out, rock hard and dripping precum from the tip, all messy. Phoebe instinctively stuck her tongue out and ran it along the shaft of her son's penis, stopping at the tip and cleaning up all of his messy precum.

"Oh my God, Mom!" Kaden moaned, rolling his eyes back in ecstasy. "Are you sure about this?"

Phoebe spat in her palm and began stroking her son's cock, looking up at him with those beautiful, smoldering eyes.

"Yes, honey, I'm sure. You gonna let Mommy take care of you?" Phoebe whispered.

"Oooh, yes," Kaden sighed out.

Phoebe kept jerking him off, keeping him lubed up with his flowing, delicious precum, and spit, while fondling his balls with her other hand and affectionately planting kisses on his hips and tummy.

"That feels so good Mom."

Phoebe locked eyes with her son as she jerked his cock off. It was such a depraved moment, but so incredibly beautiful as well.

"Let Mommy know when you're gonna blow, honey. Do you wanna ejaculate all over Mommy's breasts?"

Phoebe began untying her robe with her hand, still expertly jerking off her son. Her tits were out for Kaden to ogle.

"You're so beautiful, Mom," Kaden moaned.

"So are you honey," Phoebe smiled and kissed Kaden's tummy again, running her thumb around his pisshole to collect more precum, smearing it along his shaft and lubing him up even more.

Kaden had never experienced sexual pleasure quite like this before. Sure, he enjoyed hook ups with his little high school girlfriends, and could jerk himself off very well, but having his mother, on her knees, looking up at him while she stroked his raging hard erection? Nothing compared. He felt a monstrous orgasm boiling in his balls.

"I-I think I'm gonna cum soon Mom," Kaden breathed out, in between moans of ecstasy.

"OK, sweetie, Mommy's just gonna keep stroking your penis and aim you at her chest."

"OK," Kaden whispered.

Phoebe did exactly that, as she stuck her chest out and furiously jerked off her son's cock. Aiming it directly at her titties, Kaden moaned out,

"Fuckkkkkkk Mooooooom!"

And out shot ropes and ropes of cum from Kaden's dick. Some splattered on her shoulders, her boobs, her collarbone, and some even on her chin. Kaden absolutely coated his mother in cum, as his cock just kept spurting one blast after another. When his orgasm finally subsided, he looked down at his kneeling mother, all messy with his semen, no less horny but now satisfied. Phoebe took her hand off his cock and instinctively licked up the cum that got on her hands, as Kaden grabbed hold of his penis and milked out stray droplets of cum, wiping them on his Mom's shoulder.

They kept continuing this taboo act: Phoebe licking her son's cum from her fingers and Kaden wiping his cock on his mom's exposed skin, as Phoebe said lovingly,

"That's it baby, get it all on Mommy."

Once Kaden did finally get it all on Mommy, he sat down on his bed, panting and overwhelmed. He looked at his mother, cum dripping messily from her chin, beaming at him with motherly pride, and all creeping thoughts of regret washed away. She did it because she wanted to, and he wanted her to. If the feeling was mutual, why overthink it?

Phoebe let her robe fall entirely from her body, revealing her childbearing, slender body in all its naked glory to her son.

"Wow," Kaden said in disbelief, smiling to himself, "thanks Mom."

Phoebe sat her nakey, cummy self right next to Kaden on the bed, her dripping pussy already soaking into her son's bedsheets. She put her arm around Kaden and pulled him into her, resting his head on her shoulder-the one not dripping with incestuous cum-and said lovingly,

"Oh you don't have to thank me honey, anytime."

Kaden pulled away from her and looked her in the eyes earnestly, his cock frustratingly creeping back to life already.

"Anytime?"

Phoebe didn't answer directly, instead she leaned in and kissed her son on the mouth. Kaden didn't kiss back at first but quickly reacted, their hot, wet mouths meeting in a taboo, mommy son french kiss, sloppily licking each other's tongues. Kaden's cock grew fully erect again as he ran his hands up and down his mother's naked back.

Eventually, they separated, and Phoebe's eyes glanced down to Kaden's painfully hard erection once more, as she said,

"Anytime sweetie, but now it's time for you to get ready for school."

Kaden blushed as he noticed his mother's acknowledgement of his again aroused state.

"OK Mom."

Just then, Jordyn came around the corner and stood in the entrance of the bedroom, this time in slightly more clothes: a pair of little pink panties and a white camisole. She leaned against the side of the wall and took a bite out of an apple.

"I see you two had a moment," she said jokingly.

Kaden panicked and covered up his cock with his hand and looked towards his cum covered, fully naked mother for assistance. She simply sat there with a smile on her face.

"Kaden, honey, don't worry, Jordyn doesn't care if we do things like this. Now take your hands from your penis and show your sister how big you are," Phoebe said, rubbing Kaden's shoulder.

Jordyn smiled at Kaden and glanced down to his crotch, playfully winking at him.

Kaden slowly but surely removed his hands and exposed his hard dick to his older sister, standing straight up and pointing at his tummy. Kaden bashfully looked around as his erection made itself known to his sister.

"Nice cock bro," Jordyn teased, shamelessly eyeing up her little brother's hard penis.

Kaden giggled to himself,

"Thanks Jordyn."

Phoebe stood up from the bed and stretched her nude form, still all dripping and messy with cum and began walking over to Jordyn.

"It's really nice isn't it? Your little brother has a beautiful penis."

Jordyn now had a hand in her little panties and began casually rubbing her pussy in front of her mother and baby brother.

"It really is," she said, subtly moaning under her breath as she masturbated, "and is all that cum from you?"