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.