The Monster Pt. 15

The Monster Part 15

By Charlie Flemming

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, nymphomaniac

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

Thursday, September 29

1

Jack had three new messages when he woke up the next morning. The first was from Clara.

___

Clara: Jo is super mad at you! Did you know we made out?

Jack: I "heard"

Clara: Haha, you are so funny! Anyway, I will try to convince Jo to talk to you today, but I don't know if she will. Here's hoping!

***

The next was from Rose and Jack thought about deleting it, and maybe blocking her number, but threw caution to the wind.

___

Rose: Look, I know I fucked up. Jo won't talk to me now. I really made a mistake and I'm sorry.

***

Jack really didn't want to reply to her. But he also knew if he didn't Rose would just start spamming texts at him.

___

Jack: I won't forgive you if that's what you're asking for.

Rose: Whatever, I don't care.

Jack: Then why are you texting me? You obviously want something.

Rose: I just wanted to apologize. I realize I've been poking my nose where it doesn't belong. Even if you're both making a huge mistake, I guess that's your mistake to make and stuff.

Jack: Thanks. I guess. Sorry Jo isn't talking to you either. I guess.

Rose: Thanks. I guess. ;P

***

One more message, this one was sent by Aunt Rita very early in the morning. Looking at it made Jack drop his phone. It was another picture of her pody, this one showed everything from her neck down her to knees. Rita's pussy was shaved, and she had a hand on it spreading her pussy lips out so Jack could see every last detail of his aunt's perfect cunt. There was a message right below it.

___

Rita: Your "hypothetical" girl is waiting for you to tell her the truth.

***

Jack's cock was rock hard in an instant. He realized he might have made a huge mistake asking Rita for advice last night...

He didn't reply but tried to think of something to say that wouldn't piss his sister off. He decided he should try to talk to Jo before he did anything else he was going to regret...

2

Jo wouldn't even look at Jack again as they were driven into school. Jack was feeling especially depressed for his first two classes. Beth noticed this and thought maybe it was because he did so poorly in their "special class" yesterday.

Beth decided to change it so she could teach Jack in a way that was easier to understand, just so long as I don't let things get out of hand as I did on Tuesday, this will help Jack enough I'm sure he'll get a girlfriend in no time... she thought, feeling good that she could make such a positive difference in her student's life.

When Jack came into Beth's classroom during the third period, Miss Ryder had set up two regular chairs so they were both very close together and facing the chalkboard. Beth sat in one of them and motioned for Jack to sit in the other chair.

"What is this about?" He asked before sitting down next to her.

"I thought maybe we could do something a little more hands-on," Beth told Jack with a smile. "We'll pretend we're at the movies and that this is your first date," she explained, "and you can put into practice the things we talked about yesterday."

"Um, you want me to touch you?" Jack said, a bit confused since he thought Beth said they should never do that again.

"Yes," Beth explained, "But only in ways we discussed yesterday were appropriate for a first date. So, now, let's pretend to watch the movie."

She turned to the chalkboard and so did Jack. Jack kept his hands on his knees and felt kinda stupid staring at a blank chalkboard.

After a few seconds, Beth rubbed her leg against Jack's, "Remember, Jack," she said, "where are some appropriate places to touch a woman on the first date?" Beth leaned over to him slightly to try to indicate he should put an arm on her back, she rubbed her thigh against his again so he could put a hand on her leg and to give him a couple of options to choose from.

Jack, who had been too distracted thinking about his sister to remember anything they talked about yesterday. And was also too frustrated, also because of his sister, to really care what Beth was trying to make him do in that instant. Instead, as she leaned into him, Jack leaned right back into her and their lips met.

"Mmmmm..." Beth moaned as she necked with Jack, all her inhibitions forgotten as their tongues began playing an overly complicated game of chess.

Jack once again unconsciously knew what his teacher wanted. And she didn't want to be slow this time. As they kissed, he undid the front of her blouse and Beth reached behind her and undid her bra and soon her large perky tits were hanging out in the middle of her classroom. Excitedly, Jack grabbed both of them, one in each hand, and he tweaked her nipples as her pussy flooded with desire and need.

Jack seemed to sense something else and stopped kissing her but only to then shove one of her glorious tits into his sucking mouth. He played with her nipple with his tongue, which made Beth see stars.

"Oh, God!" She moaned, "How are you so good at this!" She grabbed Jack's head and pulled it closer, further into her breasts and she began to cum in her panties just from this intense nipple play.

"Oooohhh... Jack!" She moaned out, running her hands through his hair as her body shook, "I'm cumming! You're making your teacher cum!" She let go, moaning out like a maniac as an orgasm over her.

As soon as her orgasm was over, Beth pushed Jack away and put her bra back on, "That... shouldn't have happened." She put plainly, obviously upset.

But Jack, his confidence renewed, realized that Beth was actually the perfect woman for him, she's not related to me, and she's not Rose... obviously a match made in heaven, "Go out with me." He said.

"What?" Beth said looking at him in shock, "Jack, I'm your teacher. We can't date. I'll get fired."

Jack shrugged, "What we did today would get you fired. I just think we have a connection and would make a good match. Besides, it could help me get better at dating?"

He was very eager but also more confident than Beth had ever seen this typically shy student. It made her feel conflicted then. She knew she should turn him down... "I'll think about it." She ended up saying and then sent him back to his study hall for the rest of the period.

3

Jack feeling a lot better when he came to lunch than when he did that morning. Making out with Beth for the second time definitely helped lift his spirits.

He sat at his normal table and saw Jo and Clara sitting at the table they used to sit at before they started joining him. Jo sat facing away from him but he kept noticing her glance over her shoulder at him and he knew she and Clara were talking about him.

He felt miserable again, God dammit, and now I kinda feel like I just cheated on Jo again by making out with Beth... But then he got a little angry and thought, Then again she called it off this time. It's not really cheating if we're broken up. Jack felt a bit better after that thought.

He ate his meal for a moment but then noticed that Rose was sitting at a table by herself. She was sitting close to a table full of football players. One of which seemed to be aggressively hitting on her. Rose was being friendly but Jack could tell she really wasn't interested in his advances but the football player seemed oblivious to her dislike of him.

Jack glanced at his sister across the room. She was still facing away from him. He knew she wouldn't like it but Jack felt partially responsible for Rose being forced at a table to herself. He sent her a text.

___

Jack: If you want you can sit with me.

***

Rose saw it and wrote back quickly.

___

Rose: I'm trying to get back on Jo's good side. I don't think sitting with you will do that.

Jack: Fine. Eat alone.

***

Rose read that and the doofus hitting on her turned to say something else but she was already carrying her tray to Jack's table.

"Thanks," Rose told him as she took the seat next to him.

"Whatever," Jack said, "just didn't like seeing what's-his-fuck being a dick to you."

Rose glanced at the football player. He was already joking with his friends and had forgotten she was ever there. "Jack, what are you, jealous?" She said, playfully.

Jack rolled his eyes, "Yeah, I wish I could be the one who's a dick to you." He said sarcastically.

"You see," Rose laughed, "That's all I really wanted." She then grabbed his leg under the table and gave it a playful squeeze. At least, that's what she thought she did.

"Ah! What are you doing?" Jack said as he pushed back from the table to get away from Rose's touch. His cock was still hard from his encounter with Beth and Rose just grabbed it out of the blue.

Rose started laughing hard, "Oh hahaha, I thought, hahaha, ooh, haha, I though I was, haha, grabbing your leg." She started to calm down then laughed even harder, "Your third leg, hahahaha."

"Hahahahaha, very funny." Jack said sarcastically as he pulled back up to the table. His phone beeped again. It was Clara. He replied right away and ignored Rose as she laughed at him.

___

Clara: Jo wanted me to tell you that you're not making many points with her sitting with Rose.

Jack: Tell Jo she called it off. We broke up. I can do whatever I want.

Clara: Jo said that she doesn't want to talk to you or Rose ever again.

Jack: Tell Jo she's being unreasonable. Rose and I are just eating together. It doesn't mean anything.

***

Rose had calmed down but was still smiling like the Cheshire cat at him. Jack put his phone down and glared at her.

"I'm glad you're amused by my predicament," he told her, annoyed.

"Truthfully, I'm more amused by how uncomfortable you get about all this stuff." Rise told him with a wink. "It makes me wonder what you'd do if I..."

She stopped talking because Jo and Clara had brought their lunches over to Jack's table. They sat, Jo on the other side of Jack and sitting very close to him considering she didn't acknowledge him sitting there otherwise.

"Clara," Jo said to her cousin across the table from the other three, "Tell Jack that if eating lunch is meaningless then I don't see why we shouldn't eat together since "meaningless" is just how Jack made me feel during our relationship."

"Jo said," Clara started to say to Jack.

"Jo," Jack said ignoring his cousin, "I'm sorry. I should have told you what was happening, I-"

Jo turned her head to him just to say, "I'm not speaking to you." And then turned back to her food.

"Well," Rose put in then, somewhat sadly, "I know you're probably not speaking to me either but I figure I'll just say that I'm sorry too." A moment later she added, "I mean, I texted that already but you didn't respond so..."

"Oh," Jack said, bitterly, at Rose, "You didn't spam her phone to death either."

"You two have been texting?!" Jo snapped angrily at both of them, it was loud enough a few of the other students glanced over at them so she said more quietly but just as upset, "Oh my God, I can't believe you. Either of you. How long has this been going on?"

"Not long," Rose said but looked away, ashamed.

"Jo," Jack said then feeling his own anger rising then, 'I want to talk to you about our future."

"We don't have a future." Jo spat back.

Jack clicked his teeth before continuing, "No, we do, one way or another. And the way I see it right now." He held up a finger, "A, we say 'fuck whatever anyone else thinks,' ignore the fact that we're twin siblings, and just start dating. Mom probably kicks us both out of the house, we both drop out of high school to get jobs, and we move far away to a place where no one knows who we are or the fact that we're siblings leaving life as we know it right now completely behind us." He held up a second finger, "B, we forget that we did the things we did. We forget that we have feelings for each other we shouldn't have. We go back to being a normal brother and sister who possibly hate each other like we did before, but we have a typically normal relationship with each other like society dictates we should." He held up a third finger, "Or C, we keep everything secret. We date other people. We pretend we're still normal siblings who may or may not hate each other to everyone else, but when we're alone..." Jack let it hang in the air and put his hand down.

Clara, Rose, and Jo all listened to Jack without interrupting.

"Well, I'm kinda horny, now," Clara said with a giggle.

"It sounds like you've been thinking about this a lot," Rose observed.

"Yeah, well..." Jack said and smiled comfortingly at Jo, "I just have a hard time rushing into things until I've considered all the options."

Jo smiled back at Jack but it wasn't a happy smile, "I guess I've been thinking childishly that I could have my cake and eat it too." She sighed, "I still don't like the idea of you with anyone else though."

Jack took her hand under the table so other students around them wouldn't notice. Jo didn't push it away. He squeezed it lovingly, she held him strong, "Then maybe option B is best and we go back to being brother and sister." he suggested, not the most enthused he'd ever been about something.

Jack started taking his hand away but Jo held him tightly, "I hate that idea." She told him, "And I guess option A is out of the question. So I guess we'll just have to keep it secret..." She glanced at Clara and Rose, "except because I've been avoiding you we couldn't talk about this in private..." She laughed at herself.

Rose rolled her eyes, "You're both crazy and I will always disapprove of this." She huffed, "But your secret safe with me."

All three of them looked at Clara, who thought the conversation was over, and went back to eating. She looked up a moment later when she noticed them staring, "What's up?" She asked with gusto.

"You know to keep this a secret, right?" Rose asked her ignorant friend.

"I better," Clara said with a laugh, "or I'll never get that threesome."

"Not this again," Jo said with a groan. And all of them laughed.

4

Jack felt pretty good for the rest of the school day. He hoped that managed to smooth things over with his sister at least. And he wondered if they'd be on for another meet-up in the basement again.

He was going to text her about it but almost as soon as he was back in his room there was a knock on his door. This was kinda odd since most of the time people just walked into his room whenever they felt like it.

Jack got up and answered it. It was Sara, his mom. She was wearing one of her typical everyday outfits, the same thing she had on when she picked them up from school. It was a tight t-shirt that hugged at her breasts and since it was white Jack could see the color of Sara's bra was red through the cotton. She was also wearing a pair of jeans that showed off her naturally curvy legs and ass.

"Can I come in?" Sara asked her son.

"Um, yeah, sure," Jack said, feeling nervous all of a sudden.

Sara came in and Jack closed the door behind her. "Maybe you should lock it." She suggested.

Jack could feel his face flush as he bolted the door. He had a feeling he knew what this was about and, even after smoothing things over with his sister, he still wasn't sure if he should go through with it.

"Well, it's been two days since the doctor's appointment," Sara said, feeling very nervous as well, "so it's time for me to pose for you so you can masturbate." Sara had been thinking about it basically the whole day. She had also, more or less, been finger fucking herself to several orgasms throughout the day. Sara wanted to make sure she didn't feel anything sexual in any way when she did this for her son.

Jack gulped, feeling conflicted, "We don't have to Mom..." he said, "I only want to if you feel comfortable with it."

Sara took a breath and smiled at him, "I think..." she licked her lips, "I think so."

"Um, okay..." Jack mumbled. He was feeling especially nervous. It was one thing fooling around with his sister, but this was his mom! That was like ten times worse!

Jack thought of the doctor's appointment 2 days and remembered there was something they did that made him feel a whole lot less nervous then, "Um, I don't suppose," He stated, "That we could kiss again?"

Sara was taken aback by that, "Um, why?"

Jack answered honestly, "It's just that I don't feel entirely comfortable doing this with you," He admitted, "But I thnk that would help ease my tension."

Sara nodded, "Okay." She stepped towards him, she could feel herself getting excited, but it worried her. "Um, whenever you're ready." She said as she came up close to him.

Jack leaned in and kissed her. And just like before, they both lost all control. They wrapped their arms around each other. Sara grabbed his ass. Jack started pawing at her tits. Sara's pussy was immediately soaking wet once again, even after a full day of masturbating, it seemed.

She suddenly pushed him away, feeling like she was going to cum already just from kissing her son. "Um, we, um, should, um, start." She mumbled as she stepped away from him and turned on his radio to distract her, "How about some music?" She asked, "That might help the mood."

"Uh, yeah, whatever you want, Mom," Jack said to her as he stared at her beautiful backside, especially his mom's ass. He was definitely feeling less nervous... "Should I start?" He asked eagerly.

Sara found a station playing a slow song, "Um, yes, sure." She said not looking at him. She heard as her son's pants fell to the ground. She took a breath, then turned to him.

Even though she'd seen Jack's penis many times at that point, Sara still gasped when she turned and saw his hard, monstrous dick out with both his manly hands on it. She unconsciously licked her lips as she imagined, just as she did every time she masturbated that day, what such a mammoth cock would feel like plunging in and out of her throbbing pussy.

Jack started to slowly jerk himself as he ogled his mother as she stood there. He still felt strange doing this with her there, especially in his bedroom as it just seemed different in the medical office, but as he started jerking faster, he began caring less.

"Mmm," Sara moaned, feeling her pussy juices flowing like a river in her panties, "It's so big son!" She started swaying her hips to the slow beat of the music, "Such a giant cock my son has..." Sara said dreamily, her eyes seeming to glaze over with lust. She put her hands on her hips as her whole body moved to the music. Her moved slowly up her body, cupping her tits for a moment before going back down again. Slowly Sara moved her hands back down her belly and then her hips. She spun around as her hands reached her ass, bending over slightly and sticking her butt out, her sexy curves on full display for her son.