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
Thursday, September 22
1
Jo had set an alarm for much earlier than she normally woke up but since Aunt Rita was so hard to catch lately what with her working late almost every night, the only good time to catch her was really early in the morning like right then.
Jo practically ran out of her room and down the stairs but when she got to the kitchen she acted like she hadn’t been rushing.
“Good morning,” Jo said to her aunt as she came into the room.
“Morning,” Rita said back to her niece as she sipped her coffee at the table. She was in her nurse’s scrubs already, “You’re up early.”
“Yup,” Jo said, she was too excited not to just cut right to the chase, “so, um, I heard about, uh, Jack’s medical condition…” she put out into the air between them.
“What about it?” Aunt Rita replied.
“I, um, was just wondering what’s wrong with it,” Jo felt she wanted to be more specific so nothing was left to chance, “His, uh, penis, I mean.” She added.
Rita cocked an eyebrow, “I mean, that really isn’t any of your business.”
“I know,” Jo explained, “But I’m just wondering why, um, he’s incapable of having an orgasm. Just seems strange to me.” She hoped that was a good enough excuse.
Rita looked at her niece suspiciously but then her features softened when she decided, it is a strange condition. Of course she’s curious about it, “It’s not that he can’t orgasm, he just can’t do it by himself,” she remembered what Dr. Naomi told her the last time they talked, “Well I guess he can when, umm, an actual woman poses for him, but porn doesn’t work.”
Now Jo looked at her aunt suspiciously, “How did you figure that out?”
Rita took a very long sip from her coffee to give her some time to come up with some excuse. She decided it didn’t matter since she wasn’t the one who did it, “Dr. Naomi Moore, she’s a specialized doctor for this sort of thing. I guess she found that out in some kind of laboratory experiment.” Rita said casually. It was sort of true.
“Oh, interesting.” Jo said, she got what she came for, “well, I should go back to sleep now, g’night!” And she basically ran back to her room.
That was weird… Rita thought but noticed she had to leave for work. She forgot all about the interaction as she left.
2
Sara woke up covered in sweat and her own pussy juices. She had her usual nightly wet dream staring her son. This time she dreamed that she came to him in the shower and sucked his cock until he came all over her face and then she let him fuck her until he came again deep inside her pussy. That’s when she woke up cumming all over herself.
God damnit, she thought, every night now!? What the fuck is wrong with me!?
Sara tried her best to calm down but instead she just started thinking about Jack’s last doctor’s appointment two days ago. How hot it was watching him jerk his thick cock, how good his semen felt dripping down her skin, how good it tasted. Even after having such an explosive wet dream, Sara started feeling very horny once again almost immediately.
Sara still refused to masturbate though. Especially not while thinking about her son, no matter how humongous his cock was
She got up and went to take a shower but Jo was in it already. Sara scoffed at the bathroom door as she heard the water running from the other side.
Sara’s pussy pulsed as she realized her son was sleeping soundly in the room behind her. Overwhelmed with conflicting emotions, and before she even realized what she was doing, Sara pushed her way into her son’s room. She closed and then locked the door behind her, again, Sara wasn’t exactly sure what she was doing but she knew she wanted at least some time alone with Jack.
She turned to his bed. He was sleeping on his side. Sara knew her son slept naked and realized that she was only in her robe and nothing else. She thought to turn and leave but her pussy twitched again, egging her onward.
As Sara got to the side of Jack’s bed, in his sleep, he turned onto his back. Sara gasped when she saw the gigantic tent her son’s morning wood was making in his blanket. Holy shit! It’s even bigger than I remember kurtköy escort it being… She thought bitterly, God dammit! Why is it that I have to be cursed with a son who’s so fucking hung!
Sara bitterly sighed as she suppressed the urge to reach under the covers and grab it. She decided the real reason she came in there was just to wake her son up for school. She put a hand on his shoulder, her cunt spasming again at even that much contact with the object of her sexual fantasies, and then shook him lightly.
“Huh? What?” Jack said as he came out of sleep. He was having a dream about his sister Jo, in it she was kissing him and he kept pushing her away but then he’d give in and she’d kiss him again until her pushed her away again, then gave in, and round and round it went. When his Mom woke him up, he was painfully aware of his erection and once again bitterly upset that he couldn’t do anything about it. “What’s up Mom?” He said to her pretending there wasn’t a huge tent in his blanket.
“Just waking you up for school,” Sara told him with a motherly smile. She glanced at the tent again, and for a brief moment she really wanted to ask Jack if he needed help taking care of it. Obviously he does since he can’t cum without help. But I need to get my mind out of the gutter. She briefly considered coming clean with her son about her feelings, but then thought, no, I can’t do that! I’d traumatize him for life! Ugh… she thought as she realized, He’s probably traumatized already from cumming all over his mommy’s face…twice! How can he ever forgive me after that?
Sara looked back into her son’s eyes. He was staring at her strangely, “I think…” She said slowly, “I think we should talk…” Sara wasn’t sure how to start the conversation so she let that hang in the air for a moment.
“Okay,” Jack said, wondering what the hell was wrong with everyone lately as his mom continued to glance between his face and the obvious erection he had under his blanket, “What do you want to talk about?” He asked finally.
Sara still wasn’t sure this was a good idea, “Well,” She stated, “It’s about what happened in the doctor’s office. You see-“
She was interrupted when someone out in the hall tried the doorknob, “Hey Jack!” Jo’s voice came, “Why is your door locked? You’ve never locked it before.”
Sara looked very scared at her son’s face, not sure what to do.
Jack looked at his mom, then shouted, “I’m, um, changing.” He said feeling stupid. He slept naked so why would he lock the door to change his clothes?
Jo didn’t seem to notice the discrepancy, “Oh, cool.” She said, though really she was worried he was locking her out because of what she did last night. “Um, well, Clara’s not here. I think she stayed over at a boyfriend’s house last night. Um, so I thought I’d drive the two of us in to school. What do you think?”
At that point Jack just wanted her to go away so he said, “Sure, sounds great!” Before he realized that he just agreed to be alone with his sister.
“Okay, cool. Um, I’ll let you change.” Jo said, feeling better then, but still worried her brother was trying to avoid her.
Sara thanked her son for not giving away that she was in there. When she crossed the hall to take her shower, she wondered why she was even worried her daughter caught her. But was also glad she didn’t admit to her son that she had feelings for him.
That’s just something I’ll have to sort out on my own. Sara decided.
3
Jack did manage to avoid his sister throughout breakfast by taking his cereal to his room. Once they were in the car. He tried to concentrate on the window and hoped that Jo didn’t feel like talking.
Jo took a bit trying to figure out what she was trying to say to her brother. For one thing, I kind of just want to park somewhere and see if I can convince to make out in the backseat all day, but I know I freaked him out SO much yesterday…Ugh, this is a stupid place to be in, trying to do more stuff with Jack will only drive a bigger wedge between us, but as I do this stuff with Jack I just keep wanting to do more!
Jo thought about what they did last night in their bedroom,”You’re an amazing kisser.” She said without thinking about it. She blushed profusely after that and would have buried her head if she didn’t have to keep her eyes on the road.
“I am?” Jack asked. But then realized his sister was fucking with him. “Oh, shut up. I get it, I’ve never kissed anyone before, I’ll always be terrible, leave me alone.” He said, though this actually made him feel a little better, Jo’s just back to her bitchy self. Maybe things will go back to how they were where she’s back to hating me instead of…whatever she thinks of me now…
Jo bit her lip, then turned up a side street that didn’t lead to school but Jack didn’t notice. “I’m serious.” She said, “You have a gift, Jack. A natural talent.”
“Now I know you’re lying to me,” Jack said, amused, “I’ve never been good at anything my whole life. Well, except aydıntepe escort for video games, and we both know that doesn’t count.”
Jo pulled into a parking lot. It was Make-Out Point where they came for their “date” the other day with Clara.
“Why are we here?” Jack asked, “So you can get us in trouble again?”
“We didn’t get in trouble.” Jo said, “Miss Ryder is at school by now anyway.” She unbuckled her seatbelt, “Come on, let’s get in the backseat. There’s something I want to show you.”
Jack, limited experience that he had, really wasn’t sure at all what his sister had planned to do anymore. Still, he got out of the car and into the backseat as Jo climbed over the seat to get there.
“Okay,” Jack said, sarcastically, “So, what did you want to show me?”
“This,” Jo said as she leaned in and started kissing him on the mouth. Jack, despite all his protests and doubts, kissed her back. Their tongues wrestled in first one mouth, then the other, then both. As she kissed him she took his arms, which he hadn’t been doing anything with, and put them around her. Jack immediately started rubbing her up and down her sexy back, up to her shoulder blades, and then back down to just above her ass and then back up again.
Holy shit, Jo thought as she felt herself losing all control, pleasure coursing throughout her body, even his hands on my back feels better than anything any of my previous boyfriends have ever tried with me! What is it about him!? What? He’s so good! Why?
She broke the kiss long enough to ask, “What is it about you?” Before kissing him again. Her clothes felt constraining as she licked all the spit from her brother’s tongue this time, “I want you to fuck me.” She moaned as she broke the kiss this time.
Jack felt his already very hard cock throb in his pants. But he also felt his brain try to leap right out of his skull in fear. “AH!” He shouted and pushed his sister away as he got out of the car. He walked across the parking lot and away from Jo.
“No! Wait!” Jo shouted as she got out of the car after him, “I’m sorry! I was only kidding!” She shouted but Jack kept walking. “Wait! Please! Just let me take you to school at least!” She felt like crying. “I”m sorry for fucking everything up!” She yelled.
This made Jack stop walking. He stared out at the city for several seconds, each one feeling like an eternity to Jo, before turning around and coming back.
Jo felt tears start streaming down her face then. But out of relief. She quickly dried her eyes not wanting her brother to see her like that. When he was close enough. She grabbed onto him and hugged him so tightly.
Jack didn’t hug back right away, but after a few moments like that he began to feel a bit silly and lightly patted his sister’s back comfortingly, “It’s okay. I came back, see?” He said, and added in a more jovial way, “Not like I had much choice, this is too far to walk to school or home either way.”
It wasn’t really a joke but this made Jo laugh. She broke the hug, but still felt miserable, “Please don’t hate me for what I did.”
Jack rolled his eyes, “Of course, I don’t hate you, Jo.” He said, “I’m just not sure, um, well, about anything lately.”
Jo thought about this, “If you have any questions, I’ll answer them.” She said, and then decided to add, “I promise I’ll always be honest with you from now on.” And she meant it.
Jack considered this, “Okay, then what’s been going on with you lately?”
Jo bit her lip and looked away from her brother, “I…really don’t want to answer that right now.” She said.
“You promised you wouldn’t lie to me.” Jack pointed out.
“Well, that wasn’t a lie,” Jo laughed, but Jack looked back at her seriously. She sighed, “Okay, but can we get back in the car first?”
“Sure,” Jack said and went to get in the front seat but Jo motioned to get back in the back. Jack felt that was probably a bad idea but followed his sister back there anyway. Jo sat on the opposite side of the car this time, so they weren’t touching. “So?” Jack said after a minute of silence.
Jo took a breath, “I, um,” She felt all those butterflies returning to her stomach again. Jo felt she was about to let her brother in on her greatest secret, even if it was something she only just discovered less than a week ago. “This is hard for me okay? There’s some truth for ya.”
“You know,” Jack pointed out feeling more than a bit annoyed, “You just told me you wanted to have sex with me. How can whatever it is be harder to say than that?”
Jo scoffed at her brother but she knew he was right, “Fine, whatever. I realized last Friday that all my boyfriends are boring. They don’t make me feel good. I just use them for pleasure, and for the most part, they fail to actually give me pleasure.” She stopped talking then and looked to gauge her brother’s reaction.
“Yeah, you’re super popular, you have a lot of boyfriends, so what?” Jack said, annoyed, “I already know this stuff.”
“Had.” Jo corrected.
“What?”
“I tuzla içmeler escort had a lot of boyfriends.” Jo explained, “I told you before that I broke up with them. All of them.”
“Ah, so, they bored you and you broke up with them. Got it.” Jack said, unemotionally. It kind of annoyed Jo because she felt he was being dismissive of all this truth she was telling him.
She huffed, ‘Well, you know the rest.” She said like it was evident.
Jack cocked an eyebrow, “What? I do?” Jack shook his head and looked out the window disappointed and angry, “Of course you aren’t going to tell me? Why should I trust you anyway? You’re trying to-“
Jo quickly moved from one side to the other in the car. She grabbed her brother by the neck of his shirt, and then kissed him on the mouth as his head spun towards hers. Jack kissed her back again before he could even process why this kept happening again and then she broke it, “Because of you, idiot!” She said to him, “I broke up with all of them because of you! God, why is that so hard for you to understand!?”
Jack just stared back at her oddly. Jo moved a little away from him because she felt she’d gone too far again.
“Because I’m me.” Jack admitted a moment later and Jo looked back at him compassionately, “I’m not popular. I don’t have any friends unless you include Miss Ryder. Most of the time I feel like Mom and Aunt Rita probably wouldn’t even notice if I just disappeared or something like it. And, no offense, but up into about a week ago you basically treated me like dirt, Jo.”
Jo sighed. “I know, but that’s not who I am anymore.”
Jack sighed too, “I don’t know if I can just accept that, Jo.”
Jo cringed but knew Jack wasn’t being unfair. I mean, he’s right. All I did was devalue him and treat him like shit. And now I’m expecting him to just jump into bed with me? God dammit! Why was I so mean to him? If only you knew how I see you now, Jack. If you only knew how special you are to me… She thought about telling him again but knew it was probably pointless. I’m just going to have to prove it in some other way… She remembered what Aunt Rita told her about Jack’s condition, “What if I helped you?” Jo asked.
“Help me how?” Jack asked, still not sure if he could trust her.
“With, um, you know,” Jo said, trying to sound casual even though she was feeling even more nervous than before, “Help you with your, um, problem?”
“Which problem are you talking about now, I have so many?” Jack asked with a cheeky smile. Jo was glad he still had his sense of humor, at least.
Jo licked her lips and then pointed at the tent in Jack’s pants.
Jack sighed, “No, I’m not going to have sex with you, Jo.” He said, “If you haven’t been paying attention, I’d probably fuck it up anyway.”
Jo bit her lip as she thought about fucking her brother again, “No, not like that.” She said, “I just heard that, um, if someone posed, uh, or danced and stuff, then you can masturbate, and cum, and stuff…”
Jack blinked, “And you’d do that for me? Pose for me?”
Jo nodded. “I’ll do anything for you.” She admitted.
Jack rolled his eyes at that, “Jo, the more you talk like that the less I trust you.”
Jo scoffed, “Why? I said I’d be honest with you and-“
“Jo!” Jack interrupted, angry now, “Trust isn’t just freely given, it’s earned. You know that.”
Jo considered that, “Fine.” She said as she started the car again, “Then I’ll just have to earn your trust then won’t I?” Jo said, though her brother didn’t become putty in her hands (like she did every time she was in his hands…) She was feeling a lot better having admitted that she had feelings for him. And she was very hopeful that she could eventually convince him to have the same feelings for her.
4
They showed up to school late, it was after the first period. So Jack didn’t see Miss Ryder at all that day not even to pass her in the halls.
However, at lunch, something surprising did happen to Jack. Though he supposed later that he should have suspected it would happen. Jo completely ignored the table she normally sat next to Clara and Rose and walked over to sit with her brother.
“Eating with me now?” Jack asked as he glanced around the room and realized everyone was staring at them, I guess it’s not every day the most and least popular people in school eat with each other, even if they are brother and sister.
“Yes.” Jo said confidently. She was in her element, unlike Jack, she was more confident when she knew people were staring at her, “And we’re going to make this a normal thing.”
“Oh yeah,” Jack said doubtfully as he pointed across the room at Rose and Clara. Rose was staring daggers into Jo while Clara was pretending to while secretly giving Jo a thumbs up where Rose couldn’t see it.
Jo scoffed at her cousin but was actually quite pleased with Clara’s approval, but I can’t let her know that!
Jo turned back to her brother at the table, “I don’t need them. I’d rather be here with you, Jack.” She said with a sweet smile with just a hint of sexuality (she couldn’t start overtly flirting with her brother at school, at least not while everyone was looking at them, now could she?), “You should know that by now.”