Copyright 2022 Charlie Flemming
Author’s Note: All Characters are over the age of 18
This story begins in 2022
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.)
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…
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 bahis şirketleri 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.
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. >:/
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.
Jack: It’s not like that. We’re just talking again and don’t want mom to know.
Rita: Yeah right. You don’t have to lie to me, Jack…
Rita: I mean, I sent you pictures of both my tits and pussy. You know you can show that to your mom and get me in trouble if I tattle.
Jack: Nothing’s going on, I swear.
Three dots of Rita typing something remained at the bottom of the screen for a very long time. So long, Jack thought about switching to the next conversation but then it came in.
Rita: Okay, I’ll be honest with you. I know I’m your aunt, but Jo is your sister and that’s worse! And I know you’re attracted to me, even if you trying not to be. And when I thought you were talking about me yesterday, and thinking you wanted to share me and your mom with you… Oh God Jack, it really made me hot and horny! I can’t believe I’m telling you all this, but I was totally willing to give up all my boy toys right then and there and just jump your bones! And I keep hearing things from your Mom and Naomi that just makes me so hot I have to masturbate myself into a frenzy! And I’ll just tell you what I thought you were telling me yesterday. That you wanted me, that you bahis firmaları wanted me all to yourself, and that you wanted multiple women all to yourself. At the time I thought you meant your Mom and maybe Naomi, but now I see you mean Jo, your own sister! And I’ve thought about it, Jack, I’ve been thinking about it since we talked last night. And, if you want me to, I’ll do it anyway, Jack. I know it’s crazy, I know I’m your aunt, but I want it, for both of us.
Jack felt a bit dumbstruck as he read that wall of text. He had a feeling that Aunt Rita felt taboo feelings for him, she did jerk him off and send him naughty pictures of herself, but he didn’t know how far it went. He wasn’t sure entirely what she was saying though, not specifically anyway…
Jack: What do you mean, exactly?
Rita: Ugh, don’t be dense, nephew…
Rita: I mean, I want to do what I thought you said. Even though it’s not what you meant. 1, I want to be one of your women. 2, I want you to be my one and only man 3. I want to help you grow your harem
Jack blinked at that. He really didn’t know what that meant.
Jack: What’s a harem?
Rita: Mmm, you know what? I’m going to leave work now. I’ll tell you when I get home. 😉
Jack gulped. Though Jo was way more sexually experienced than he was, she didn’t intimidate him nearly as much as his aunt did. His dick was rock hard now though. All he knew at that moment is that was one more thing he couldn’t tell Jo about…
The last three messages were from his Mom, Rose, and Dr. Naomi. Jack picked the one that seemed least intimidating.
Mom: Hey, sorry again for going out of control…
Jack: No, it was my fault. I just really wanted to kiss you and made something up to do so.
Mom: That’s…actually kind of sweet. Thank you.
Jack: You’re welcome, Mom.
Mom: Did you enjoy today’s, um, session or whatever we should call it.
Jack: Yeah, I really like when you danced to the music. It was very sexy.
Mom: Oh? I was actually concerned that I, um, behaved a bit…slutty.
Jack thought for a moment to write, “It was slutty Mom but it was also super hot!” But realized that wasn’t the right way to talk to his Mom right then.
Jack: No, you weren’t Mom. I just thought it really helped.
Mom: Oh good 🙂
Mom: I’ll have to learn to dance better for you…
Jack: You were great today Mom.
Mom: When do you think you’ll need that again?
Jack’s cock was rock hard from talking to his aunt, now it felt like it was even harder somehow. He considered telling Sara that he needed it again right away but decided if he pushed her too much it probably would only drive a large wedge between him and his mother.
Jack: Um, I think every other day is probably fine.
Mom: Oh, okay. I’m glad we’re doing that part right.
They then chatted about some inconsequential stuff and Sara asked what Jack wanted for dinner but he wasn’t sure. Once that was done, Jack didn’t really want to talk to Rose still so he moved onto the only other one.
Naomi: Hey Jack! You jerk off on your mom yet?
Naomi: There you go with your one-word responses again. Are you lying to me?
Naomi: HAHA! I KNEW IT! How was it? Did she cum again?
Jack: I think so.
Naomi: Give me every detail!
Naomi: Hey, stop with the one-word responses. It drives me nuts. Like what are you trying to say, really.
Naomi: Ugh, fine, be that way. See if I care.
Jack wasn’t sure why he was being mean to Naomi but figured it might have something to do with how much she intimidated him. He clicked on the last message.
Rose: Thanks again for letting me sit with you. I still don’t think you and your sister should be making incest babies in your basement though…
Jack: How do you know about that?
Rose: Clara told me. And then I got Jo to tell me. Also, you just told me 😛
Jack: Is that all you wanted, to tell us not to do it anymore?
Rose: No…I guess I was thinking kaçak bahis siteleri about what you and your sister talked about.
Jack: What about it?
Rose: Well, I figure you and Jo both need a person to date, and you’d probably prefer one who is cool with your relationship with your sister, right?
Jack: I mean, when is that going to happen?
Rose: It would if it’s me! I mean, I already know all about you two.
Jack: Well, I still don’t want to date you. AND you just said you DON’T approve…
Rose: Well…maybe I would approve IF you would date me.
Jack considered this. He thought about what his aunt said about giving up others so she could be with him. Something Jo already did without a second thought…
Jack: I don’t know Rose. I said before I don’t want to be your boy toy. And I won’t do anything without Jo’s approval.
Though as soon as Jack sent that message, he realized that really wasn’t the case. He thought about his teacher, Beth, most of all. Hmm, I’m just going to have to slowly ease Jo into the idea of me dating other women. I don’t know if she’ll be that approving, especially with what I’ve done with Mom, but I can’t lie to her forever…can I?
Rose: I won’t break up with my boy toys until you tell me we can be together! If you’re just playing a trick, it would be hell to pay to force me to break it off with everyone for no reason!
Jack: I’m pretty sure you can get them back. As you said so yourself, you’re one of the hottest girls in school.
Rose: Oh, now you’re saying that! Fuck you and you’re mixed messages!
Rose: Yeah, yeah, okay. Well, what do you think about my proposal?
Jack: I think that, maybe, if you were the last woman on this planet…
Rose: Oh my god, you’re awful!
Jack: I think I get it from you…
Jack realized that maybe Rose could help him trying to balance multiple women, but he knew he couldn’t be too direct about it.
Jack: So, how do you keep so many boyfriends anyway?
Rose: What’s it to you?
Jack: Just curious.
Rose: Um, it’s just casual dating. You’d probably know more about it if you, you know, dated anyone. I go on a date, sometimes we screw, and then tomorrow I go out with the next one. They’re all doing the same with the girls they date so who cares?
Jack: Oh, okay.
Rose: And why did you want to know that?
Jack: Um, no reason.
Rose: No one ever does anything for no reason…
Jack: Um, I’ll talk to you at school tomorrow.
Jack turned his phone off and plugged it in. He felt Rose actually had a pretty good idea, except that he still didn’t trust her for shit.
Jack was doing homework about half an hour later when his aunt came into the room. She was still wearing her scrubs from her work as a nurse. Rita had very large breasts, they pushed into the hospital top and created an obscene amount of cleavage. While the bottom hugged her hips and showed off her glorious ass, though the rest hung loosely around her legs. Jack gulped, nervously, feeling his cock getting hard in his pants like it felt it had been basically all day.
“Um…hi…” He mumbled nervously as his aunt shut the door behind her.
Rita thought to lock it but decided it would be suspicious, and she knew she couldn’t just fuck her nephew while everyone else was home, “Well, what do you think?” Rita said as she turned to Jack. She leaned over him at the desk so her boobs hung down and her obscene amount of cleavage was pointing directly at his face.
Jack stared at her breasts, his brain fogged completely over, “W-what?’ He stumbled over his words, Rita’s question never reaching his conscious mind.
Rita smirked. It was obvious that her nephew was attracted to her. She swayed her hips some, “Do you want your sexy aunt in your harem?” She asked in a husky voice.
Jack shook himself and backed his chair away from her slightly. It was hard for him to think with her like that, “Um, I’m not sure what a harem is…” He said, realizing then he probably could have looked it up on his phone since they texted.
Rita stood up straight and walked behind Jack so she could sit on his bed. She crossed her legs as she leaned back on her arms. She licked her lips. Jack felt his cock throb, Rita looking back at him like she was ready for sex, “It’s a group of women,” Rita explained, “who’s lives all revolve around one man. They fuck and suck him whenever he wants and serves him on his every need.”
Jack was speechless at that for a moment before saying, “You mean, like, they’re all his girlfriend or something?” He just wanted to be sure he got what Aunt Rita was saying to him.