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
Tuesday, September 27
1
Jack woke up early, even though he needed extra sleep because of his late-night basement visits two nights in a row. His dreams kept waking him up though. Every time he drifted off he just kept remembering how Clara or Jo's lips tasted and it only felt like his cock was getting harder and harder with every dream.
Finally, he decided to just try jerking off again. He didn't even care that he was thinking about his sister the entire time he was doing it. He imagined how her lips tasted. How good her boobs felt pressed against his. How much he wanted to keep doing more sexual stuff with her, even though he knew it was wrong, during that fantasy he didn't care.
He pictured sticking it in her mouth, even though he wasn't sure what they would feel like. Jack didn't watch porn regularly but he had seen some on occasion and he pictured what he saw there. That he was laying on his bed, as he was now, that Jo came into his room in nothing but the red pair of panties she was wearing when he came to her room the other night. Her large tits hanging out freely.
"Need help with that?" Jack pictured what his sister would say to him as she crossed the room and got on the bed. She took his whole cock in her mouth and down her throat. She started gagging on it obscenely as Jack had seen that woman do in that blowjob porn he watched once. Jack imagined as he jerked off that he grabbed Jo by the side of the head and was now throat fucking his sister as she jilled off through her panties from loving every second of her forced blowjob. It was making Jack feel really good. It was starting to feel like...like maybe he would...maybe eventually he might...
He was just about to give up again once he realized he wasn't going to cum. But that's when his door opened. His mother, Sara, was standing in the doorway.
Sara gasped as she walked in on her son masturbating, "I'm sorry!" She said, "I didn't mean to, um..." Sara was embarrassed, she considered running away back to her room, or putting her hands over her eyes, or even
closing
her eyes. But she did none of these things and even unconsciously licked her lips as she openly stared at her son's humongous dick in his hands.
Jack let go of his hands and said, 'I'm sorry too." In defeat. He grabbed his blanket and threw it over the lower half of his body, it made an obscene tent where his overly large cock was still standing like it was made of steel. "I just thought maybe this time I could cum." He didn't care that he was speaking dirty to his mom, he was so frustrated, "But I can't, I just fucking can't no matter what I do."
Sara could sense her son's frustration but was still too scared of her own feelings to offer any sort of help. Instead, she said, "We have another appointment with Dr. Naomi after school. Why don't we bring it up with her and maybe she can help us find a solution."
"Yeah," Jack moaned miserably at his mom, "I suppose I'll just wait till then." He added sarcastically.
Sara nodded, feeling too horny to really be a comforting mother to her son. "Um, I'll go take a shower." She said and practically darted out of the room. She couldn't think straight being that close to Jack's hard dick, even if it was under a blanket, there was just no way to hide it when it was erect...
2
At school, Jack was so frustrated he didn't even feel that tired despite being so low on sleep at that moment. His erection, at least, had eventually gone away on the trip over. Mostly because his mother made him sit in the front seat, so he could at least stare out the window and try not to think about how he could pick out the smell of his sister's shampoo amidst the other scents in the car.
Miss Ryder came up to him in the first period to remind him they have a "special tutor time" for lack of a better thing to call it for now, during the third period. Jack said he wouldn't have forgotten.
During the third period, he came back right on time, "Remember to lock the door behind you." Beth reminded him as he came in.
"Oh yeah," Jack had forgotten but turned and locked both locks on the door as he had done before.
"So," Beth said, "I've been considering how to take this 'class.' or whatever you want to call it. I think that since you have
absolutely no
experience at all..."
Jack winced at that because he really didn't, outside of things he'd done with his own family. Which he knew he could never admit to Beth Ryder, no matter what.
"...so I was thinking," Beth continued, "Maybe the best thing would be you to first gain some experience and then we can begin the class. What do you think?"
Jack was confused,