The Monster Pt. 06

Copyright 2022 Charlie Flemming

Author's Note: All Characters are over the age of 18

This story begins in 2022

Main Characters

Jack-18, 16" cock, light brown hair, blue eyes, 6'3" tall

Sara-Mom-36, GG-sized tits, black hair, brown eyes, fit but very tone and curvy.

Rita-Aunt-37, FF-sized tits, blonde hair, blue eyes, similarly amazing body to Sara but not quite as hot

Josephine (Jo)-sister, 18, EE-sized tits, twin to Jack, red hair, green eyes most popular girl in school

Clara-Cousin, 18, EE-sized tits, brown hair, kinda dumb but very kind

Beth Ryder-teacher, 28, FF-sized tits, redhead

Naomi Moore-38, doctor, FF-sized tits, African American

Rose (Ro)-18, DD-sized tits, Jo's best friend and a popular girl in school, brunette hair

Friday, September 23

1

This time, in Sara's dream she rode Jack while he slept. Constantly grinding him, for hours upon hours, cumming multiple times over and over and over again until Jack finally filled her pussy to the brim with his only orgasm of the night. She woke up the whole room smelled of pussy. Sara knew that she had multiple orgasms throughout the night.

This time, Sara went straight to the shower and left washing her blankets and sheet for later. As she showered she thought about what her daughter suggested, Jack needs help. I didn't think about it until now, but he does. Like Jo pointed out last night, he has a near-constant erection most days! And he can't cum without help. It's obvious now. Someone should help him and that someone should be me.

Sara then made the resolve to go across the hall, wake her son up, explain the whole plan to him, pose, strip, and maybe jerk him off or even give him a blowjob (the naughtier parts of Sara's mind added the last couple of things...). But as soon as she was out of the shower Sara lost all her confidence and went back to her room. She had to change her sheets anyway...

2

Jo decided to wake up her brother. She knew she was giving him space but she still wanted to talk to him.

She opened his door, this time it wasn't locked, and walked in. He was asleep in bed, huge morning wood under his blanket like usual. She came up and sat next to him on the bed.

Jo really wanted to get under the covers again with him but knew that would be overstepping her boundaries. Being nicer to you is going to be harder than I thought it was yesterday...

"Wake up." Jo said in a normal tone. She didn't want to shake him or touch him in any way since that would just be teasing herself at that point, "WAKE UP!" She said louder a moment later when Jack didn't stir.

"AH!" Jack said as he shot awake like he just heard the siren for a bombing rade. "Good morning." He then said a moment later and smiled up at Jo, "My favorite sister..." He then closed his eyes and almost fell asleep again.

"Wake up or I'll do what I want to your sleeping body." She threatened, then smirked evilly,"You'll probably enjoy it..."

"AH!" Jack said again as he woke up completely.

Jo smirked but was also a bit disappointed. "Alright, well, Clara isn't here again so it's just you and me to school." She then got up to leave but Jack grabbed her hand suddenly and pulled her down to him. Jo thought for a second he was about to start kissing her, but he just hugged her.

Jo hugged back, even if just for a moment, she loved the feeling of his strong back under her fingers, and his bare shoulder upon her cheek. He still had that manly smell as well.

"Thanks," he said in her ear as they hugged.

"For what?"

"For waking me up." He said and let her go.

Jo smirked, "That was a really nice hug." she said as she walked out of the room. She felt pretty great at that moment.

They ate breakfast together at the dining table for the first time in a very long time. Jack made a joke and they both laughed, Jo would complain about one of the boys or girls at school and Jack would listen, hanging on to every word.

"...and that's when I realized it was on the elevator!" Jack said as he finished up another one of the dumb jokes he knew. Jo started laughing again, completely sincerely, even though the joke was pretty awful, Jack was just so good at telling it.

Really, Jo was just glad he was enjoying any time they spent together right then. She felt she'd been losing a lot of points with him lately.

3

As they were driving in to school, Jack turned to his sister and said, "Do you want to go to that parking lot again?"

Jo cocked an eyebrow at her brother.

"I don't, um..." He said nervously, "I just want to talk."

Still, Jo turned up the side street leading to Make-Out Point feeling more excited than she did before.

Once they got there, Jack and Jo stayed in the front seat this time, "I'm a virgin." Jack said to her.

Jo almost laughed but suppressed it, "I know." She still smiled like it was another dumb joke like the ones he was telling at breakfast, "Did you think I didn't know that?"

"It's just that, well," Jack began, "You've had a lot of boyfriends. I've had zero girlfriends. You know?"

Jo wasn't getting it. She did get a bit upset though, "Are you calling me a slut?"

"What? No!" Jack said quickly, he was getting very flustered. He really wished he could express himself better, especially in these embarrassing situations."Ugh, okay, you were really brave yesterday when you told me about your feelings, so I'll try to do the same, okay?"

Jo nodded but was worried about what her brother was about to say to her.

"Yesterday, you, um, told me you wanted to have sex, and I guess that just makes me feel really small."

"What!? You're not-"

"Just let me finish," Jack said plainly, "Girls don't seem to like me, I have no confidence, I have this stupid boner everywhere I go it seems." He made a frustrated gesture toward the cock in his pants, even though it was soft right then, "I just didn't think I'd make any headway with, well, anyone. Especially not my own sister, the hottest and most popular girl in school."

Jo blushed a little, "You think I'm hot?" She asked.

"Of course, Jo," Jack answered without hesitation, "But you are my sister. And I know you just want to rush right into...whatever this is. But I need to take it slow. I'm sorry if that's not something you can, um, do but-"

Jo bit her lip and then interrupted her brother, "No, I can do that." she said with a nod, "But I think you have this whole thing a little backward."

"What do you mean?" Jack asked.

"I'm not the super experienced one who needs to slow down," Jo said, Jack gave her a look, "Okay, I'm not just that." She laughed, she was feeling very giddy again, "You're the inexperienced one who needs someone to teach them!" She explained, "Someone like me who has tons of experience, am I right?" Jo felt that this was a situation they could both benefit from.

Jo laughed at Jack's expression. He never saw it like that but in a lot of ways his sister was right, "Except you're my twin sister..." He complained, bitterly.

Jo shrugged, "I really can't help that, Jack." And laughed. "Besides, doesn't that make it hotter?" Jo certainly thought so...

Jack glanced at his sister then. Jo brushed her red hair out of her eyes so she could look back at him better. She was exceptionally hot. Her green eyes, short and cute nose, thick, ravishing lips. But was she even hotter because she was my sister...

An image of his mother dripping with his cum flashed through his mind. His cock twitched to life in his pants. I'm a fucking pervert... He thought as he realized that yes. I think Jo's right...I'm just as turned on by the taboo aspect of this as she is...but I'm also super amazingly freaked out by it too! Fuck!

"It doesn't matter if it's hot or not." He said a moment later, making a decision, "We're family, and truthfully this is the first time we've gotten along in, like, ever. I mean, do you want to fuck all that up just so we can screw?"

Jo pouted, but knew her brother was right...again... "I guess not..." She said bitterly, realizing it was over and soon she'd be back with her harem of practically useless, almost-no-dick assholes.

"I mean," Jack added a moment later, "You're also right about me having absolutely no experience and needing someone like you to teach me, so..." He shrugged as he stared out the window.

Jo blinked, "Wait, so you want me to teach you, but you don't want us to screw?" Jo asked.

Jack looked back at her thoughtfully, "Yeah, I guess that's what I'm saying..." He said, feeling especially weird admitting to it.

Jo smirked, "Want to get in the backseat."

4

Less than ten seconds later, they were in the backseat of her car. Jo sat so that her leg was rubbing up against his, she just wanted to be close to him.

"Okay," Jack asked, feeling dumb and embarrassed, "What do you want to teach me?"

"It's like you said before Jack," Jo said feeling exceptionally happy at that moment "Your the virgin and I'm the slut! You should decide what you want to learn."

"I never called you a slut." Jack pointed out, looked a bit peeved about his sister putting words in his mouth.

"I know, I was joking," Jo said as she nuzzled her head into his shoulder. "Just tell me what you want me to do and I'll do it." Jo said, her voice dripping with lust.

Jack felt even more nervous than before but he said, "Do you want to make out again?"

Jo smirked, "Always." She leaned over and kissed him, their tongues became one as their mouths locked together. Jack didn't have to be shown this time as he wrapped his arms around her and held her tightly.

Jack loved the taste of his sister's tongue in his mouth. He loved the smell of the shampoo she used that morning and the smell of her sexy skin. He loved how her back felt beneath his fingers as he moved his hands up and down her soft and sexy back.

Jo felt similar to how she did every time she kissed her brother so far. Her pussy gushed, her skin felt electrified, her nipples hardened, and she felt that any second she was going to lose all control, rip all their clothes off, rape her brother in the back of her car and seriously piss him off! (at the very least).

Instead, Jo broke the kiss, "Um, we need to, um," She mumbled, then clearer as she calmed down from her sexual high slightly, "Uh, I mean, that I need to teach you something." But that was just her excuse since she knew if she let her brother continue she was going to turn into a real horny sex fiend, "Um, when you're, uh, kissing a woman, um, they want to be touched."

"I was touching you," Jack said as he felt up her back a bit more, "See?"

"Mmm, yes," Jo moaned as she enjoyed the feeling, "I mean, NO!" She said a moment later, "Sorry, yes and no."

"Huh?"

Jo rolled her eyes, Jack really wasn't getting it, "Yes, girls like to be touched when we're making out, but not just there. EVERYWHERE!" She said excitedly and then practically rammed her face into her brother's. Their tongues started mixing saliva together, Jack started moving his hands up and down her back, but then Jo grabbed one hand and moved it to her ass. She grabbed the other hand and moved it to one of her tits.

Jack left his hands where they were without moving them in any way. He broke the kiss.

"Um..." He said as he glanced from his hand on his sister's tit, to her waist where his other hand went, to her eyes where Jo looked back at him expectantly, "Now what?" He asked like it wasn't obvious.

Jo licked her lips, "Feel me." She said and then started kissing him once again.

As they kissed this time, Jack felt her ass with his hand, feeling one amazing buttock before moving to the other. He did the same with her tits. He felt one then the other and back.

It wasn't the greatest sensation ever for Jo. Jack obviously was as virginal as he claimed to be (not that Jo ever doubted that). She didn't want to ruin his confidence though and moaned lightly into her brother's mouth with every inexperienced poke and prod.

But then something strange happened. He pinched her ass just so. It sent a shiver up her spine and she gasped in pleasure for real. Unconsciously, Jack seemed to notice this, his hand naturally found the same spot on her other buttock and Jo's lust only grew.

Jo felt her pussy gush and she grabbed the hand on her tits and without thinking about it made him grab her so that he pinched her nipple just so as he squeezed her tit simultaneously. She moaned in his mouth as her pleasure increased.

Jack picked up on this immediately. Slowly his hands seemed to naturally adjust to the most pleasurable points in his sister's tits and ass. In just a few minutes, he had gone from inexperienced groping to masterful petting. He was playing Jo's body like a concert pianist and he didn't even know it.

He squeezed her boob just so through her shirt and pinched her ass just right and kissed her so expertly. Jo couldn't believe it, but she was cumming.

"Oh fuck!" She shouted as she broke the kiss and half-collapsing into her brother's chest as an orgasm even stronger than when she dry humped Jack in her bedroom overtook her whole body, "Shit! That was amazing! You're amazing!" Jo moaned as she came in her pants, "You're so good. You are so FUCKING GOOD! Aaaaahhhhh-ooooohhhh!" She moaned out not able to hold back anymore on this intense pleasure.

As she came down from her orgasm she smiled up at her brother from his chest, "That was intense."

"What, umm... did you...?" Jack mumbled nervously.

Jo giggled as she realized Jack had no idea what her body just did (just like he didn't seem to know anything), "Haha, you have no idea what just happened do you?"

Jack shook his head.

"Oh so innocent," Jo said goofily and pinched Jack's cheek like their grandma used to when she was still alive, "so sweet and innocent." She said in her grandma's voice. Jo got really playful after a strong orgasm.

Jack rolled his eyes at her.

"That was a female orgasm," she explained, "something you just gave me with just your hands and kisses! Mmmm," she then kissed her brother for just a moment, "You have a gift, Jack." She said.

Jack cringed, "No I don't, shut up." He really just couldn't believe it. Partly because he still didn't trust his sister, no matter how much he liked kissing her.

Jo rolled her eyes, "Well, you did make me cum without even touching my pussy. That's the first time anyone's done that. And you're right maybe it was blind luck. Whatever. Who cares!?" During that short speech, Jo had gone from being happy from her orgasm to angry that her brother was so stupid. She climbed over the seat then and started driving without letting Jack get out of the backseat.

5

They were late for school again. Jack didn't see Miss Ryder that day again and hoped he wasn't going to be in extra trouble on Monday for skipping class.

Rose wasn't avoiding Jo but it seemed impossible to get her alone until lunchtime.

Jo went and sat with Jack again. Rose expected this and she and Clara took their trays across the cafeteria and sat at the same small round table that they were.

"What are you doing?" Jo asked suspiciously.

"I'm sitting with my friends." Rose said but then have Jack an angry look, "mostly anyway." She looked back to Jo, "We are still friends, right?" She said sweetly.

"Of course," Jo said disappointed but she half expected this to happen anyway.

"You don't mind, do you Jack?" Clara asked her cousin, worried.

Jack really didn't like Rose but Clara was cool, "Yeah sure."

"Yay!" Clara said with great joy and gave her cousin a hug. Her large, bouncing tits pressed into the side of his arm. In no time at all, Jack had an erection.

When Clara broke the hug, Jack quickly pulled himself closer to the table so it hid the tent in his pants from sight, but everyone at the table knew what had happened.

"Jo, I need to use the restroom." Rose then said and she and Jack's sister walked out of the cafeteria.

When they were gone, Clara moved her chair closer to Jack so she could whisper to him, "That was a great kiss, by the way." She was referring to when he kissed her on their fake date over a week ago.

Jack had all but forgotten about it, but now it was all he could think about as he dropped his fork on his plate. "Um, yeah, right, uh, thanks." He said nervously, wishing these things would stop happening to him...

"Can I ask you something?" Clara said innocently.

"I guess so," Jack said, though it worried him, whatever it was.

Clara glanced around before whispering, "Did kissing me freak you out at all?"

Jack thought about it. Well, for one thing, I did just make out with my sister for the second time earlier today... but that also still worries the hell out of me! AH! WHY IS EVERY WOMAN SO CRAZY ALL OF A SUDDEN!

He answered honestly, "Yeah," when he saw that Clara was hurt by that he added, "but I also kinda liked it." He then, too late, glanced around to make sure none of the other students at other tables were listening in. They didn't seem to be.

"Hmm," Clara hummed as she considered it. "Did you like it more, or did it freak you out more?"

"Why are you asking?" Jack said, not really wanting to even consider the question.

"Because..." Clara said, making sure one last time that no one was listening in before leaning in and talking really low, "Maybe, after everyone goes to bed tonight, you'd want to kiss me again?"

Jack almost choked on his milk.

6

As Jo and Rose walked down the hall, Jo asked, "Should we use the bathroom by the chemistry lab or the one by the library?" It was more a question of which one would have fewer people then and how private whatever it was Rose wanted to talk to her about.

Rose grinned like the devil, "How about the girl's locker room?"

Jo blinked, but thought, Rose doesn't know anything about me and Jack talking there yesterday. She just has something especially secret to tell me. "Sure, why not?" She said and they walked into the girl's locker room.

They both made sure the coast was clear before they met up in the locker area and sat on one of the benches.

"Okay, what is this about?" Jo asked.

Rose had considered what to do with the information that she knew: That Jo was in some kind of incestuous lust with her own brother! But after thinking of multiple ways to blackmail, or subvert, or indoctrinate Jo, Rose realized she only really liked making up schemes with Jo. So she changed her mind and decided to come clean about the whole thing so they can be friends again, "I know your 'secret boyfriend' is your brother." She said plainly.

Jo did a double-take, then glanced around the empty locker room even though they had already checked everywhere, "No...um, no, you're mistaken about that." Jo said, trying to sound like she couldn't even dream where Rose got her information from.

"I'm not." Rose said confidently, "And you know I'm not."

Jo cringed, though Rose was her friend she also knew she could be especially nasty. Even going so far as to blackmail, subvert, or indoctrinate people sometimes... "Then what are you going to do about it?" She asked her, worried.

Rose squinted her eyes as if she was about to do something really nasty to the person she once called her "BFF FOREVER!"

But then she said, "Nothing. I am going to ask, 'what are you thinking, girl?' and then pretend nothing is going on otherwise." Rose seemed somewhat smug about her decision to, essentially, look the other way.

"It doesn't freak you out?" Jo asked, not realizing it was the question of the day.