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
Thursday, September 29 (cont.)
5
After his mom left, Jack lay down on his bed in his post-orgasmic bliss. And after that, he was starting to feel a lot less conflicted about cumming on his mother, that…was fucking awesome! He thought, and how was she dancing? Is that how strippers dance? He wondered. Since he always had his orgasm problem, he’d never really seen too many sexual things like porn or the like, so he didn’t actually know what strippers danced like.
He heard his phone beep then but saw that he had seven new conversations again. He rolled his eyes, “I was never this popular in my whole life…” He groaned but with a smile. Jack was beginning to like the attention.
The first message he read was from his teacher, Beth.
___
Beth: I’ve thought about it, but I don’t think we should go on an actual date. I could lose my job, Jack.
***
Jack really didn’t like reading that. Even though things seemed to be working out with his sister now, he still felt Beth was the best candidate he had for a girlfriend. He decided he wasn’t going to let her go without a fight. But he also knew he couldn’t just up and tell her that. He decided to try something else…
___
Jack: It’s because I’m not very attractive, isn’t it?
Beth: What? No! That’s not it at all!
Jack: You don’t have to lie to me, Miss Ryder, I’ve never had any experience with girls and I probably never will.
Beth: Jack, you’re very handsome. I actually think you’re very attractive…
Jack: Then why can’t we go out on a date?
Beth: Because I’m your teacher, Jack!
Jack: That didn’t stop you from kissing me today. I already told you I won’t tell anyone about anything that goes on between us. Please, can’t we just go on one date? Just so I know what I’m doing if I ever go on a date with anyone else?
***
After reading that message Beth put her phone down so she could think. She was actually naked at the moment but only because she had been in the tub when Jack’s first message came in. She placed her phone on the bath table she had next to her tub.
Beth thought about what Jack just told her, Fuck my life… I mean, today he gave me one of two of my best kisses ever, the other one being the one Jack gave me on Tuesday that somehow lasted a whole class period. Jesus…he’s such a good kisser time just flies by… How can he still be so virginal at the same time though? I should just take him to a hotel for an afternoon and…Ugh! I can’t fuck him! I definitely can’t date him! I’ve been playing with fire already, and I should just cancel our “special class” and forget about this fucking crush I have for my student…
Though that seemed like a final decision for her, those thoughts had also started to make Beth feel very horny as she thought about Jack’s tongue in her mouth or his hands on her tits. Fuck. I’ve got it bad, don’t I… I really need to help Jack find a girlfriend. Then he’d be too distracted with her to think about me! Yeah! And a “play date” will help with that.
Now that she’d rationalized her decision, Beth replied.
___
Beth: Tomorrow after school, I’ll take you out. It’s not a date. Just a play date like you had with your cousin and sister, okay? Tell anyone you need to tell it’s a special after-school project for extra credit.
Jack: Thanks Beth! You’re the best teacher ever!
Beth: Thanks, I can’t wait.
***
Beth regretted saying that right after she sent it. Mostly because she realized it was true…
6
Jack felt really excited now, a date with Miss Ryder! Sweet! He was so excited he almost forgot there were more messages to check. He hit one at random. It was from Clara.
___
Clara: I think Jo wants to meet you in the basement tonight. I think I should be there 😉
Jack: I’m not sure if we are or aren’t. Did she tell you that?
Clara: No. Just a feeling I get when I mention your name she’s all like ‘oh, i wanna suck his dick tonight’ lol
Clara: She didn’t say that, but that’s just how I feel talking to her…
Clara: But I think you should convince Jo to let me be there too 😉
Jack: I still don’t know, Clara, I just got back on her good side. I don’t want to fuck it up again.
Clara: Well, like you said today if you want to keep it going it’s got to be a secret, right?
Jack: Yeah, so.
Clara: And you should both date other people, right?
Jack: Clara, you aren’t ‘other people’ you are my cousin.
Clara: I know, but I think if you let me come tonight it would help Jo get over her jealousy…
***
That one made Jack think, that would be a good thing for Jo to get rid of, especially if I’m going to start dating Miss Ryder.
___
Jack: Okay, I’ll try but no promises.
Clara: YAY! 😀
***
Jack clicked on Jo next since they were talking about her.
___
Jo: Hey bro.
Jack: Hey
Jo: What you said today made sense. I guess I’d rather have you in secret than not at all…
Jo: But I also don’t want to share you with anyone else 🙁
***
Jack cringed when he read that, Dammit, of course, she’s not just going to let me date other people. I probably shouldn’t tell her about the fact that I just jerked off on Mom’s face and tits, or that I’m going out with Miss Ryder tomorrow… Should I even mention that Clara wants to come down tonight? Does Jo even want to do that anymore?
___
Jack: Do you want to meet in the basement tonight? We could talk more then.
Jo: I do, but I’m still kinda mad at you. >:/
Jack: So…no?
Jo: Ugh, no, I will be there. Clara keeps trying to convince me to let her come too…
Jack: Well, I think that if Clara came, it might help you be less jealous.
Jo: Can’t you dating other people wait until, like, we’re both 30 or something? Also, Clara’s your cousin, that wouldn’t work to fool people.
Jack: But if she’s there, you might learn to share with others better. I won’t do anything with her I wouldn’t do to you first 😉
Jo: I still don’t like it, but fine. I’ll tell Clara.
Jo: And I swear if I come down there again and you’re making out with her I’m going to be super pissed!
Jack: I promise we’ll wait for you 😉
Jo: You better! 😉
***
Jack clicked on the next text message group. It was from his Aunt Rita.
___
Rita: So, I figured it out…
Jack: What’s that?
Rita: What you meant last night. You weren’t talking about me, you were talking about Jo.
Jack: Uh oh…
Rita: So, you and Jo sneaking around huh?
***
Jack couldn’t believe he was so stupid to think he could ask Rita for advice without giving something away. He decided to lie and hope he didn’t give up any more information.