The Monster Pt. 21

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

Friday, September 30 (cont.)

9

Jack was woken up by Beth about 20 minutes later. She was dressed in a normal outfit. She looked really different like that.

"Hey, beautiful," He said, dreamily as he woke up.

"Don't call me that." Beth said, mad. As Jack's cum washed off her body in the shower, she had gone from being giddily satisfied to guiltily angry with herself.

Jack was fully awake then, 'Um, I'm sorry." He murmured, wondering if maybe they're hard core fucking had all been a dream.

Beth calmed down, "No, I'm sorry. This was my fault. I let my, um, feelings get the better of me and I should have called this off before any of this happened." She turned away from him, mostly because he was still naked, "I think you should get dressed and go. I'm putting a stop to our special class. None of this can happen again."

"No, Beth, please!" Jack pleaded, not believing it, he thought for sure it was because he didn't do a good job, "I was a virgin before, and I can get better at the sex stuff, I'm just-"

"No, that's not it." Beth said, turning back to him. She realized that she was being cruel especially to someone who'd never had sex before, "You were amazing, Jack." She said this almost sadly, "But I'm your teacher. Not only could I get fired, it's immoral, unethical, and I..." She turned away from him again, "I don't want it to happen again. Okay?"

"Okay..." Jack said, feeling about as depressed as he could feel. He dressed, and then walked out the door. He thought about asking her for a ride but felt too awkward about it.

He also didn't want to text his mom because he felt awkward with her too after finger fucking her that morning. Jack was also pretty sure Aunt Rita would still be at work. Jo was grounded. Rose and Clara didn't have cars. That left only one person.

About half an hour later, Naomi was picking Jack up again from a nearby gas station. She drove onto the road without asking Jack where he lived, "Okay, what happened?" She asked when she saw Jack's incredibly pained expression as he got in her passenger seat.

Jack told her everything. When he was done Naomi whistled, impressed.

"So, you just lost your virginity to your sexy teacher, and she called everything off huh?" Naomi smiled, "And now your harem is broken before it's even begun..."

Jack rolled his eyes, "I still think it's impossible. And I still think I'll probably fuck up my whole family if I haven't already." He stared out the window as Naomi drove down the road. "I think I should just be glad I lost my virginity and give up."

Naomi laughed, "Oh, my god, Jack. One little hiccup and you're ready to throw in the towel? No wonder you've been single for so long."

Jack glared at her, he was losing his temper, "You know! You could-"

"No!" Naomi shouted back, not appreciating being yelled at, "You don't know! And that's the problem!" She then laughed and said, "Women never, ever, ever know what they want. Trust me, I am one!" She laughed again.

"I noticed." Jack said, much less amused.

Naomi playfully slapped his arm, "Hey, lighten up okay? All is not lost, in fact, this is probably a good way for you to learn how to turn a loss into a success."

"How?" Jack asked, "She basically told me she's never going to talk to me again."

"Except that she's your teacher so unless you skip every class you have with her from now on," Naomi explained, "You're going to talk to her again. And, secondly, it sounds like you fucking rocked her world."

Jack didn't believe that for a second, "What? No way. It was my first time, I'm sure I sucked."

"You gave her five orgasms Jack! You also went down on her without her asking you to! Those are both bonus points for you, trust me. She's going to be wanting your services again real soon."

"You really think so?" Jack asked hopefully.

"I know so," Naomi explained, "But only if you behave accordingly. This is a test, she might not even know she's testing you but she is."

"She is?"

"Yes, absolutely. She's testing to make sure you don't flip out and do something crazy like call her incessantly, or turn into a baby trying to get her to be with you. The best way to deal with this, believe me, is to act like you don't care about her at all."

Jack scowled at her, "I already said I don't want to be an asshole."

"I think you don't understand," Naomi explained, "You would be more of an asshole if you started acting like you cared too much. I know it's strange but it's true. She needs to be the one to come to you next. Just don't text her, or call her, or at school sit with your friends and talk to them all class as if whatever she says is just background noise. Do this until she comes to you. Then you know she's yours."

Jack thought about this, "So it's kinda like I'm testing her too." He stated a moment later, "If she comes then I know she wants me and if not I move on."

"Now you're getting it," Naomi smiled, "So, who's next on your chopping block? Your Mom? Your sister? Me?"

Jack's cock twitched in his pants as he thought about it but then said, "I guess I'll just see what happens moment by moment."

"Hey, you're learning." Naomi told him and she finally got his address and dropped him off a little down the road from his house so no one asked questions.

10

When Jack came in the front door, he realized the advice Dr. Naomi gave him could work for his mother and sister as well.

I fooled around with both of them, now we wait and see what they do. He thought.

When he came, no one was around so he went to his room. He lay in his bed and took out his phone, but no one had texted him in a while. Back to being unpopular, I guess.

He took a nap until dinner, Rita woke him and they came downstairs together.

As they ate, Rita suddenly spoke up, "So," She started, and spoke in a very concerned tone, "Jo and Jack were caught naked again in the basement." Jo gasped at that, "And Sara has been posing for Jack in provocative ways so he can masturbate on her body." Sara gasped at that.

Jack glared at his aunt but then tried his best to each his dinner nonchalantly, I have to pretend this doesn't concern me, like Naomi said, act like I don't care until Mom and Jo come to me... He was very doubtful of all of it, but figured he'd try anything.

"Don't tell them that!" Sara shouted at her sister. She looked at Jo and saw she was staring daggers into her.

"I think we need to stop keeping secrets around here," Rita said plainly, "We keep doing these things behind closed doors like this and we'll just rip this family right apart. I want this family to be close, and I think if we keep these things in the open, we'll be closer because of it."

"I agree Mom," Clara chimed in, happily.

"Thank you sweetie." Rita said to her daughter, glad she had an ally in all this.

"Oh, but I'm in trouble for doing stuff with Jack," Jo spat angrily as her mother, "But you can do whatever you want with him?"

Sara blushed and looked away from the table, "I..." she started but all she could think about at that moment was how good her son made her feel that morning using only his hands. She was feeling very guilty, to say the least.

"That's exactly why we need to make a better gameplan," Rita explained, "Concerning Jack, I mean. We can't have him running around with erections all day, but when these things happen in secret, we're liable to do things we'd regret later."

Jack seemed incredibly interested in his dinner at that moment. Sara noticed this and wondered aloud, "What's Jack's take in all this?"

Jack seemed to notice anyone was talking about him, "Mmm?"

Sara opened her mouth but didn't say anything. She looked to her sister for help.

"We were wondering," Rita told her nephew, "If you would be okay with doing your 'posing sessions' let's call them, in a group setting."

Jack was feeling like that was a horrible idea, but he was being nonchalant so he just shrugged and said, "Whatever."

"Oh, good, see." Rita said, "He'll do it."

"I don't know if I'll do it though," Sara said, "Let's just forget about it for now and talk about it later." Sara was actually hoping they'd just forget about it actually.

11

After dinner, Jack was about to go back to his room for the night when his mother stopped him.

"Remember, you're sleeping with me now." Sara told him and motioned him into her room.

Jack came in, pretending he didn't care one way or another where he slept. He started removing his clothes and then lay on top of the covers naked.

Sara ogled her son's body but then looked away, "Um, I know I slept naked last night, and, uh, you normally sleep in the buff, but I usually don't sleep that way. Do you mind if I'm wearing pajamas?"

Jack shrugged and grabbed his phone, "Do whatever you want." He said and pretended that the fact that he was naked didn't concern him at all.

"Um, okay..." Sara said. Her son was acting strangely, and it was making her feel a tad insecure and she wasn't entirely sure why. She was also feeling strange that he was naked on her bed, not covering himself up, and it didn't seem to bother him...

Sara took off all her clothes and lay on the bed opposite her son, "I guess sleeping naked is more comfortable." She rationalized, even though she'd never thought that before.

Jack did his best to not react, but his mind was going nuts, holy shit! It worked! Mom got naked on her own and now we're both in the bed nude! What the fuck?! This is actually working!

He could feel his cock rising but he pretended it wasn't, he also didn't look at his mother's nude form on the bed, instead feeling encapsilated by what he was doing on his phone.

Sara bit her lip, unsure of herself. She watched her son's cock rise, and thought maybe it was because of her being naked so close to her son, but he seemed so distracted she wasn't able to confirm that. She had a sudden desire to get closer to him, Sara just wanted him to at least acknowledge that he was in bed with his naked mother.

She scootched over on the bed towards Jack and then rested her head on his shoulder to see what he was doing, "What'cha reading?" She asked.

Jack actually hadn't been doing anything but when she moved over he opened a random webpage, "Um, something about construction workers," he said, opening a page about new real estate being built nearby. He continued to look through the article like he was actually reading it. Trying not to notice his mother's breasts being pressed into his arm as she nosily poked her head over her shoulder.

Sara felt strange again about her son's response. She felt like he was making fun of her, almost, with his indifference. "Alright, well, I'm going to sleep," she announced, going back to her side of the bed, getting under the covers, and turning out the light.

The room was pitch black other than the light from Jack's phone. But he turned that off a moment later and got under the blankets as well. He felt like he fucked up again, ignoring his mother like he was. Now he was sure he shouldn't have tried the "indifference technique" on her like he thought might work. He lay awake worrying about it and almost fell asleep...

There was a hand on his arm and Jack was fully awake again, "Do you mind..." His mother whispered in the dark, "If we snuggle? It's been along time since I had someone to spoon, you know?"

Jack thought, did she forget this morning? But then realized this was her making a move, she's passing my test! He told Sara, "Whatever," as if the thought of holding her didn't interest him that much.

Jack's unemotional response made Sara really seriously doubt herself right then. She really thought that Jack would be excited to touch her body. She thought he found her sexy... Sara was conflicted because she knew that, for one, she probably should want her son to no longer find her attractive, but she also felt a bit crushed at that moment picturing her son's desire for her to be dead.

The thought that Jack didn't want her anymore made Sara to suddenly lunge forward in the dark and start kissing him. It was dark so first she was just kissing his cheek but Jack turned and they were making out in the dark on her bed. Sara could feel how much her son desired her just by how passionately he kissed her. Her worries were gone, but her pleasure was just beginning.

Jack was trying not to get as distracted as he did with Beth this time. He remembered the "teasing rule" of not giving his mother entirely what she wanted. He moved his hand down her back as if he was about to grab her ass, but then stopped just before and moved back up. He put his other hand on her belly, he moved it up and almost cupped her breast, but then changed direction to almost touch her pussy, but then moved back up. It was a slow process, and he and his mother was making out the whole time, but he knew his mother's arousal was skyrocketing.

Jack wasn't wrong as Sara was dying for her son to grab her ass, grope her tits, and stroke her pussy. But he wasn't doing any of it!

She took the initiative and reached out and grabbed her son's dick under the covers. She slowly jerked it and thought for sure that Jack would move on to making her feel better with his hands then he was already, but he didn't. He just kept teasing her. And it was driving Sara insane with lust.

She stopped kissing Jack to ask, "Will you eat me, Jack?"

Jack was confused by the question, his mother didn't want him to cannibalize her... Did she? "Huh?" He asked.

Sara sensed Jack's confusion and almost laughed, "Will you lick my pussy, please?" She asked timidly.

"Oh! I'm an idiot. Yeah, absolutely Mom!" He said excitedly as Sara lay on her back and he found her pussy in the dark.

Jack started sucking his mother's clit, not believing just how well this teasing thing worked. He had an idea as he licked his mother's labia, can that work still? Even during sex...

He felt his mother's orgasm building and suddenly switched to a different part of her pussy with his mouth and tongue and her pleasure would diminish but her orgasm would start building once again.

Sara was going crazy with need as he son kept keeping her from cumming. Once he did it a third time she lost her mind. She closed her legs around head and rolled over so that Jack had to turn over with her and was now on his back. Sara sat on his face and ground her pussy against his tongue, "Please!" She moaned out in desperation, "Please, Mommy needs to cum! She needs it!"

This was far too hot for Jack to keep teasing her. He had been holding back for too long and now he just gave in to every desire. He lapped away at her cunt like his life depended on it. He reached a hand up in the dark to find one of his mother's enormous tits and roughly pinched her nipple. He took his other hand and grabbed her ass and find her asshole to stick a finger in.

Sara had the mother of all orgasms, she literally started seeing starts as she cried out in pleasure. Her body had been teased for too long and the buildup only made her release so much stronger than it ever had been before. "HOLY FUCK! I'M CUMMING! Aaaaahhhhh-ooooohhhh!" She moaned as Sara came harder than she ever had in her life.

Jack felt like he was drowning in his mother's pussy juice. He swallowed it all down partly in desperation so he could momentarily breath, but mostly he just really liked the taste.

Sara came down from her massive orgasm. But she was still so horny she knew the night was far from over. "We can't do this again," she said as she slid her pussy down her son's face, across his chin, and sat on his chest, "This is the only time," she moaned as she ground her cunt against Jack's body and moved down to his belly.

"Of course, Mom," Jack said figuring she meant he wouldn't eat her pussy again and already wondering how he could convince her again in the future.

Sara didn't seem to hear her son, "We can never do this again," she repeated as she reached behind her and grabbed Jack's cock, "never again," she repeated and raised her body up, and lined her son's cock with her throbbing pussy, "never again." And she came down. Sara's cunt fully encasing Jack's cock inside her hot folds.

I'm now fucking my son! Sara thought as she began to bounce on Jack's cock. She knew she should feel guilty but the thought only made her more excited in that moment. She began fucking her son even harder.

Jack couldn't believe what was happening so he reached over and turned on the light to see it with his own eyes. He watched in fascinated excitement as his horny mom's cunt engulfed his cock over and over again, "Fuck Mom," he moaned as she bounced, her giant boobs jumping around obscenely while he watched, "You're so fucking tight!"

"You're huge cock is making me so good!" Sara moaned as she jumped joyously on her son's dick, "You're fucking you're mother so good!"

She stopped bouncing as she started to cum and ground against Jack's pelvis, his cock fully inside her cunt, her body shaking in pure esxtacy.

Jack wasn't ready to cum yet so her grabbed his mother by the hips and flipped her on her back. He started fucking her like there was no tomorrow, Sara still cumming profusely beneath him.

"Fuck me! Fuck your mother! You motherfucker!" Sara moaned, loving every second of being used like she was her son's personal cumslut! That reminded her, "When you need to cum, do it on my face! I'm not on the pill!" She announced as she felt a second orgasm already building within her.

She started cumming just as her son did, she quickly got off him to lie her face in front of him on the bed. She stuck her tongue out obscenely, her body shaking from her own orgasm.

As he started to cum, Jack's mother surprised him and moved to engulf his cockhead in her mouth. She began swallowing as quickly as she could but Sara couldn't keep up with his massive load and had to take her mouth off a couple of times to swallow and Jack sprayed sperm on her lips and cheeks before her mouth latched on again to swallow some more.

Once Jack's orgasm was finished he collapsed on the bed next to his mother. She surprised him by then processing to eat his cum from her face with her hand until it was all gone. Jack's cock was hard again within moments.

Sara knew she was going to get guilty about it in the morning but just then she just felt happy, almost giddy. Still, she had to remind herself this was just a one time thing...

"We can't do this again, ever. You know that right?" She asked her son as she eyed his hard dick.

"Yeah, never again," Jack agreed though he was willing to agree to anything right then.

"Oh good, nothing that happens tonight can never happen again," Sara said as she straddled her son again, "but the nights not over yet..." she added devilishly as she started fucking her son once more...