The Monster Pt. 09

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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

Monday, September 26


Jack and Jo were so tired on the trip to school, they both slept on Clara’s shoulders in the backseat. Rita was in the front passenger seat because she had a day off from work for a change, making up for being overworked the week before, so she and Sara had plans to go out for the day after they dropped the kids off.

Jack came to his first-period class earlier than he normally did. Beth was glad of this because she wanted a word with him.

“Jack,” she said once he came into her back office with her, “what is with you lately? You’ve missed the last two classes, and you look like you’re half asleep now. Is anything going on?” Beth also glanced at his crotch but his cock wasn’t hard for once.

“I’ve just been really, umm, sick I guess because of my condition,” he said, figuring it kinda worked once to get him out of trouble with the jocks…

“You’re condition?” Beth glanced at Jack’s crotch again, doubtfully, “You mean with your penis?”

“Um, yeah…” Jack mumbled. He was too tired to understand why that didn’t make any sense.

“But why would that make you miss school?” Beth asked feeling she was probably going to have to fail one of her favorite students for the semester.

Jack realized that really wasn’t an excuse but he was trapped now, “Oh, uh, because, uh,” he cleared his throat and thought of something to say, “since I can’t orgasm on my own, then sometimes my erections will go on for so long that they start to hurt and I can’t do anything until they go away.” This actually wasn’t untrue but Jack’s erections almost never lasted that long before they went away on their own, “And I’ll, uh, sometimes wake up with a boner that really hurts so I can’t go in right away. I’m sorry I didn’t tell you, Beth.” Because they were close enough she gave Jack permission that he could call her Beth, but only when they were alone.

Beth considered this and it made sense but it also made her more concerned than she let on, “You really need a girlfriend to help you with that, don’t you Jack?”

Jack just shrugged, “I guess so.”

Beth bit her lip as she thought. She made a decision, “Since you missed so much school and we both have a free 3rd period, why don’t you start coming to my class instead of going to your study hall? I have an extra credit project that I think I can help you with.”


Jack agreed and was back in Beth’s classroom at the start of the third period. Beth was wiping down the chalkboard when he came in.

“Lock the door behind you, I just want to make sure we aren’t interrupted,” she told him and Jack locked both locks on the door.

“What’s this about?” Jack asked much more aware now that he’d had two class periods to wake up.

“I thought maybe I could help you,” Beth said, “with your condition I mean.”

Jack was taken aback by that, “Wait you mean…” He wasn’t sure how to finish that sentence.

“No!” Beth said a bit too quickly. Truthfully, since the first day of class when she whipped Jack’s cock out of his pants by mistake, she’d been thinking about fucking him an awful lot, and she really wasn’t the type of teacher to fantasize about her students. Once she knew he couldn’t cum that only made the fantasies worse as she pictured many ways to “help” Jack with his need to orgasm. But instead, she decided to take the high ground, “I have an idea though, kind of built off of what you, your sister, and your cousin were doing with your “play”-date.”

Jack still wasn’t sure what Miss Ryder was getting at so he stayed silent.

“I was thinking I’d help teach you about women and dating, and you’d get extra for it. Call it even for taking the blame for, um, what happened, and letting me keep my job.”

Jack was still confused, “So… you want to go on pretend dates with me?”

Beth laughed, “Um, no. I want to teach you like it’s a normal class, basically. What do you say?” Before he could answer she added, “I strongly recommend you do it since I don’t think you’ll pass my class this semester without it.”

Jack shrugged, “Sure, like I said before I really Girne Escort don’t know anything when it comes to girls… I suppose any help would be good.”

“Okay, then how about we start this ‘class’ by you telling me just how much sexual experience you’ve had?” Beth asked.

Jack cringed. He realized he probably shouldn’t mention anything he’d done with his family members, and then realized he had yet to do anything with anyone outside of his family, “Nothing really,” he said.

“What? You haven’t even kissed a girl?” Beth said suspiciously, she was still fairly certain she saw Jack making out with his cousin when she caught them at Make-Out Point.

Jack shook his head, “No. I wouldn’t know the first thing about any of that.” Though he was lying about kissing someone before, he felt he was still telling the truth about not really knowing anything about kissing.

Beth scoffed, she hadn’t been expecting Jack to not even have kissed someone before. “Hmm, well that certainly gives me something to think about for tomorrow.”

And Beth dismissed him, wondering what she was going to do exactly, “He’s never even kissed someone…” she said. She remembered what she saw and knew he was probably lying about that one, but still, she had to start their class somewhere.


Though Jack and Jo still ate together, so did Rose and Clara. Rose sat between them and made sure to dominate the conversation so that Jack and Jo couldn’t talk to each other for the entire period.

Afterward, on their way to the next class, Jo asked her, “Why did you do that? I already told you we’re both grounded and can’t talk at home…” Jo was more disappointed than angry with her friend.

“And I told you I would do anything in my power to keep you and your brother from doing,” Rose was going to ‘the nasty’ but they passed a group of students right then so instead she said, “Anything you might regret.”

Jo scoffed at Rose and started walking away from her to get to the class before her friend did but Rose caught up anyway by literally running, “Jo! Don’t be angry.” Rose said as she caught up to her, “I’m only trying to look out for you since you seem to have lost your mind!” Rose said this like it was a joke.

Jo didn’t find it very funny though, “You know what I think?” She said as she stopped walking in the hall and people filtered around them, “I think I realized that there’s something better than this stupid popularity game we’re always playing and made some changes. I broke up with my boyfriends. I stopped spending every second of every day with you. And I think you’re just scared by these changes. You’re acting petty and the only thing I can think is that you’re jealous or you’re scared of losing me as your best friend, or I don’t know what.” Jo started walking again, away from her friend feeling like she’d made a point but really she was just angry that everyone seemed to be working against her lately.

Rose was hurt from being accused of being a jealous friend but also realized that Jo was, at least, partially right. She caught up again and this time pushed Jo, not forcefully, against a locker to get her to stop moving. “Is that really what you think, Jo? That I’m doing this all because I’m worried I’ll lose you? I’ll admit, I miss hanging out with you, but I also know that what you’re doing is just crazy!” Rose glanced around but the hallway was mostly empty now since class was about to start, “I mean, Jack can’t be that good right?” She asked in a low voice.

Jo looked into her BFF’s eyes for only a second. She had an unemotional expression on her face, trying her best not to betray anything. She pushed past Rose and walked into her next classroom before the bell rang, like some kind of robot.

Rose cocked an eyebrow and Jo in class a moment later. Even though she could tell Jo was not trying to betray her emotions, Rose could also tell, I hit something there… could Jack actually be a good lover? But then thought a second later, nah. There’s just no way, he’s like the biggest dork in the universe with zero sexual experience. Jo just has cock-lust or something and she’ll get over it once she remembers her brother is total a loser.

But as Rose thought about Jo’s odd reaction in the hallway, her brain wasn’t giving any other reason for it. She was obviously hiding something… Rose thought as she started thinking up ways to get to the bottom of it.


While the kids were at school, Sara and Rita were out shopping at the mall.

“So,” Rita said as they were sitting down for lunch, “Did you dance for your son yet?” Rita felt a thrill go down her spine as she asked it. It was one of the naughtiest things she’d ever heard anyone doing, and her own sexually ignorant sister was the one doing it!

Sara cringed, “No, though I have been thinking about it,” they were sitting away from the food court and the mall was particularly devoid of people at that time of Magosa Escort day on a Monday so Sara didn’t feel she had to be too quiet since there wasn’t anyone there to hear her, “I just really don’t want anything like what I saw with Jo and Jack to ever happen again. I think that keeping Jack’s sex drive in check will help. But I really don’t think I should be the one to do it…” Sara still didn’t want her sister to know that she’d been having very intense sexual thoughts of her son.

“Too bad he doesn’t have a girlfriend, huh?” Rita commented.

“Yeah but at this rate, I don’t think it’ll ever happen.”

“Yeah he’s pretty stupid in those regards,” Rita said without thinking, “no offense,” she added a moment later.

“It’s fine,” Sara said, brushing it off, “I mean, you’re absolutely right. Jack really hasn’t been the best with women and I wonder if it’s because he hasn’t had a strong male influence in his life since his father died and that… was a long time ago.”

They sat in silence for a moment as they ate.

“Well, if you don’t want to do it, the dancing I mean,” Rita said as casually as she could, “I mean, I could always do it for him…” she then continued eating her salad, pretending the thought didn’t really excite her that much.

Sara sneered, “Rita! Last time…” she glanced around the food court. There was no one nearby but she whispered anyway, “…you gave him a handjob.” Then in her normal voice, “Something like that can never happen again.”

Rita rolled her eyes at her sister, “I think you’re forgetting that was a medical examination. I didn’t do that because I wanted to.” This wasn’t entirely the truth but Rita felt it wasn’t completely false either, “I won’t let that happen again. I promise.”

Sara thought it over, “Well, Jack has another doctor’s appointment tomorrow. Let me talk to Dr. Naomi first and I’ll get back to you.”

Rita inwardly smirked. Naomi was probably the last person Sara wanted advice for something so sexual. Naomi was a completely professional member of the member community… but only until she got horny….


Late that night, Jack was the first one in the basement that time. He remembered his sister stepping out of the shadows before and checked both rooms before he waited on the steps. After about fifteen minutes, he started to reconsider.

What am I doing? I keep saying it’s over. I keep wanting it to be over. I keep making a final decision that it’s over…and yet here I am.

He thought about it for a while. For one thing, his dick was harder than it had ever been just thinking about making out with his sister again. And she’s so hot! Jack thought in frustration, Why the hell does it have to be my sister who’s obsessed with me instead of, I don’t know, anyone obtainable!? I mean, if she wasn’t my sister… well, I’d be living the dream! The most popular and one of the hottest girls in school can’t keep her hands off me…except she’s my fucking sister! Fuck my life!

And round and round Jack’s thoughts went until he finally decided to give up and leave before Jo came downstairs.

Except just as Jack stood to leave, the basement door opened. But it wasn’t Jo, it was Clara.

“Oh hey Jack,” she said as she came downstairs in her normal nightwear of a pair of panties and a long t-shirt. She was also carrying a basket of dirty clothes, “I’m just doing some laundry.”

Jack put his hands in front of the crotch of his shorts but then thought, what’s the point? I have an erection all the time now anyway. He let his hands fall to his sides. He just said, “Oh, I’ll, uh, stay out of your way.”

Clara put the laundry to the side and stepped up to her cousin, “What if I want you in my way?” She asked, seductively.

“Umm, I, uh,” Jack stuttered nervously as the cock throbbed in his pants.

Clara knew Jo would be down the stairs in not too long. She decided she needed to act quickly before either of her cousins, especially Jo, could talk her out of it. With Jack tripping over his own words, Clara saw this as an opportunity to close the distance between them and kiss him on the lips.

Jack was surprised but soon was kissing Clara back without a second thought. He grabbed her ass with both hands and she automatically wrapped her legs around him as she ground her pantied pussy into his pelvis. He pushed her back until Jack ran into the washing machine, which Clara sat on. Jack started moving his hands up her back and then back down to her ass. He reached into her panties to touch her bare butt cheeks. Clara undid the button of his shorts…

“What’s going on in here!?” Jo shouted from the bottom of the steps. Well, not loudly, she knew she had to be quiet, but she was obviously angry.

Jo hadn’t come down until then because she was considering wearing something sexy, like lingerie, just to see what her brother would do. She realized that it would probably just make Jack run away scared again, Kıbrıs Escort and decided instead to just wear her normal pajamas. She even messed her hair up just a bit so she could claim she’d fallen asleep and that’s why she was so much later than the night before. Jo did not expect that her cousin might get down there before she did… especially since Clara wasn’t supposed to be down there!

Jack took a step back from his cousin, but since his shorts were undone already, they fell on the floor and his hard cock popped out, “Fuck, I, uh,” he stated as he grabbed his shorts and pulled them up again.

Jo was angry enough she wanted to storm back to her room but knew then she wouldn’t get any time with Jack until tomorrow night, if he would even see her again then. Also, she didn’t want to leave Clara alone with Jack, “I can’t believe you!” She shot at Clara, not looking at her brother as he tried to get his huge cock back in his shorts.

“Why?” Clara said as she got down from the washing machine, “We already decided we’d have a threesome with him. What’s wrong with me getting a little make-out session before you do?”

The mention of a threesome surprised Jack so much he dropped his shorts to the ground again. His hard cock stuck out obscenely again. He reached down to grab his shorts from around his ankles but was too flustered and missed.

“I never actually agreed to that!” Jo spat at her cousin, then to her brother she said, “And just leave your pants off! Who cares!? Everyone’s seen your big dick already!” She was beyond angry and was getting a little loud now.

At his sister’s insulting tone, Jack grabbed his shorts and stuffed his cock down one of the legs and put them back on all in one motion. Then, Jack was the one angry now, and he said, “What the fuck, Jo!?” Then he turned to Clara, “Actually, both of you! I’m your brother and your cousin and you’re both throwing yourselves at me every chance you get lately! Why?! I’m not one of your fucking boyfriends to fight over! I’m your fucking family! We’re together for life! Unless we fuck it up by fucking or something! FUCK!” He was so frustrated, sexually and otherwise, he wasn’t thinking about how loud he was being. Jack was tired though of how his life was going lately and he really had no idea why, or how for that matter, things got so fucking out of control.

Jo was taken aback. Jack had never, ever, not once, gotten that angry at anyone! Jo had actually believed that no one could push him so far that he’d blow his top like he just did.

“Wow, Jack,” Clara said, not upset in any way at her cousins getting angry with her, “You really don’t understand just how-“

She didn’t finish her sentence as then the basement door opened. Jack and Jo immediately jumped into the other room and around the same corner to hide. Clara, however, casually went to her laundry basket and started putting some in the washer.

“Is anyone down there?” Aunt Rita’s voice came from the top of the steps.

“Yeah, it’s me, Mom.” Clara said as she put some more clothes in, “Just doing some laundry so I have something to wear tomorrow. Wouldn’t want to go to school naked.”

“Oh,” Aunt Rita said, she sounded strange. Talking slowly, and slurring her words together slightly, “I thought I heard yelling.”

“Just me, sorry Mom.” Clara said, “I was yelling at the laundry for fun!” She giggled then yelled, “Get in the wash you stupid bra!” Then she laughed again playfully.

“You know, you are always so happy,” Rita said from the top of the stairs, “My little girl…” And then went on to tell her daughter all the things she appreciated about her in a very long and convoluted way.


Behind the corner where they hid, Jo put her arms around her brother and he held her as they waited in the somewhat cold basement. They both enjoyed being this close to one another and the feeling of each other’s bodies as they held each other close.

Jo had stopped listening to her aunt, she leaned into her brother so she could whisper in his ear, “I think she’s drunk.” She said with a slight snicker.

“Yeah…” Jack agreed and softly guffawed with her, they were both very quiet, “Do you think it’ll be much longer until she leaves?”

Jo listened as Rita told Clara something nostalgic, “Probably be a minute.” She said, “Hopefully we won’t be here all night…”

“I wouldn’t mind holding you all night,” Jack whispered back without thinking about it. Then added, “Actually, forget I said that,” when he did think about it.

Jo sighed and squeezed his waist, “I’d like that too, whatever it was.” She said, “You know? Because I was supposed to forget it…”

Jack smirked, “That was dorky.”

“I guess you’re rubbing off on me,” Jo said with a smile. She looked up into her brother’s eyes. She really wanted him to kiss her.

As if reading her mind, Jack leaned in and their lips met and soon their tongues were reintroduced as well. Jo reached down and squeezed her brother’s butt, he did the same to her. Jo remembered how Jack was kissing her cousin and she jumped up to wrap her legs around his waist as she had seen Clara do. Jack held her for a moment. But then he lost his balance and they both fell into the stack of boxes behind them.

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