This is my first work that started by playing with KoboldAI for story generation. After a while I used it less and less and, in the end, decided to rewrite the whole thing from scratch and it just kept expanding. Still will get at least a second part.
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You are Alex, a sheltered, virginal 19-year-old young man. You've just moved to live in your own apartment, and currently hold a decent job at the local carpentry shop. Both your mother Suzy and your Aunt Meredith visit you quite often to see how you are doing, so they decide to drop by.
Your mom is actually your stepmom, but she has been with you from the birth as she adopted you after your biological mother died in childbirth.
She lost a best friend but gained a child. You've never considered her to be anything else than your mom and naturally her younger sister was your aunt. Your fun, easygoing auntie. Sisters have always been very close and when you were growing up, Aunt Meredith was there more often than not. They raised you in a loving but very freely minded family. You've never known your father and the sisters were always quite enough for you.
Your mother works in a local library as a librarian, and you've never even thought that she could be anything else. You've just celebrated her 40
th
birthday which she took with good grace after all the worry you and auntie had about it. Your aunt is few years her junior and does freelance web design and thus has been able to spend time with you when your mother has been working.
The three of you are sitting at your dining table, chatting, when your mom asks the dreaded question "So, do you have a girlfriend yet?"
You sigh and shake your head. "No, not quite," you say dejectedly.
Your aunt pipes in. "What do you mean, 'quite'? You've at least had a fling with a girl you picked up at a bar or something, right?"
"Huh? No, never, I don't go to bars so much." you respond.
This is somewhat of a sore point with you. Maybe due to your upbringing you always compare every girl to the women in your life and find them lacking. Shyness and lack of social skills hasn't made approaching girls any easier. But even you think that the situation is starting to become too much. You just don't know how to break out of it.
"A virgin, huh?" asks your aunt smirking.
Your mom shoots her a dirty look. "Meredith, that's inappropriate."
Your aunt, shrugging, replies "I'm just gauging the situation." Turning to you again, she says "So, no flings, no girlfriend... Have you ever even kissed a girl?"
"No, not really" you say wishing they would stop interrogating you. "Not that it is any of your business." you mutter. The only people who have ever kissed you are right in this room.
"Ever asked a girl out? Flirted? Tried a pick-up line? Anything?"
You just look down and do not say anything.
Your aunt rubs her temples. "Jeez, a boy your age should know this stuff by now. I thought we raised you better."
"His father should've taught him all that, but... it's hard to do that when you're not around," your mom muses.
"It's not your fault, Suzy," says your aunt. "I guess we've gotta teach him." she adds in an almost resigned voice.
Thinking for a moment, your mom says "You might be right. I mean... we've taught him everything else."
"Starting a conversation, flirting, kissing, touching, sex, the whole shebang!" joked Aunt Meredith seemingly having fun at the idea of getting to see me embarrassed.
"If you say so" you mumble almost inaudibly, not at all that excited about the idea. Ok, thinking about flirting with auntie - while quite cringey - would not be that difficult. You always have had fun with her. Sex... nope, even if you had looked at her appreciatively sometimes. Thinking thoughts like that of mom was mega-cringey to say the least.
Although you had to admit that at this point almost any warm human being would probably do. Being a 19-year-old virgin was no fun. No fun at all.
"I heard that role-playing is a good teaching tool," your aunt says. "So, Alex, you're going to pretend you're at a bar, chatting up your mom, who just pretends she's someone else. She's hot enough for that."
Your mom laughs. "I'm gonna need a drink for this. Or maybe two." She gets up, heading for your liquor cabinet. She starts to pour herself a drink.
"Good idea," your aunt says. "That'll make it more authentic. Pour one for us, too!"
Your mom returns with a drink for each of you.
Your aunt begins "Okay, chatting! You see this girl sitting alone. Maybe she's lonely? Go up and talk to her. Look at me if you need help."
You turn to your mom and stutter out "Oh... Hi. I'm Alex. How are you this evening". Your aunt rolls her eyes but lets you continue.
"So, what do you think?" asks your aunt looking at you critically. "Do you like her?"
You nod. "Yeah, I think so," you say. As if you could say anything else.
"Good. Now, flirt with her. Tell her you like her hair, her eyes, her smile, her laugh, her ass... whatever it is you like about her."
"What about her tits?" you ask.
"Go ahead and tell her," Your aunt encourages. "You don't have to be shy about it. We are practicing."
"Okay," you say obediently. "I like her tits."
"Tell HER that, you dimwit. " Your aunt says, rolling her eyes again. You are starting to feel a bit bad about this whole thing.
"Sorry"
Turning to your mom again, you blurt out "You have nice tits." and blush immediately.
"Oh, thank you" your mom says with a twinkle in her eye. "That's very sweet of you."
"How'd you like that?" your aunt asks her. "Did you like it when he said your tits were nice?"
"Yeah. I did," mom says hiding her smirk. "Quite authentic."
"Well, you're obviously not a complete moron. So, let's keep going. Next, you're going to make a move. Tell her you want to kiss her. Do it now!"
You nervously look at your mom and she gives you nod. "Go ahead," she says.
"You are so beautiful that I'd really like to kiss you right now." you say to your mom hesitatingly.
"Okay, I just have to say that you're really adorable when you're embarrassed. That would work with quite a few women." she points out and takes a sip.
"What do you mean?" you ask.
"You just said that you'd like to kiss me," your mom says. "That's cute. Some women really like cute."
"I didn't know what to say," you say a bit embarrassed.
"Just say it," says your aunt. "Say it to her."