Trained by Aunt and Mom Pt. 01

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."

"I would really like to kiss you," you say to her with more confidence.

"Okay," she says. "But don't be too pushy."

"I won't," you say. Your mom has another drink. "You want another one?" she asks Aunt Meredith

"Sure," she says "this is a bit difficult sober."

Your mom hands you a drink. "Here you go," she says with an odd smile on her face. "It's my special recipe."

You take a sip. It's not bad with a citrus flavor, rather strong though. Nervously you throw down the whole drink in a single gulp.

"Now, kiss her," your aunt commands.

You look at your mom and she nods at you again. You turn to her and begin to lean in until you hesitate "You mean I REALLY kiss her?" you ask them.

"Yes," they both say almost exasperated.

"Okay then," you say leaning in and giving her a quick peck on the lips.

"That was nice," she says. "Not very ... but... nice."

You look at your aunt for confirmation. "You can do better. Look at her. Isn't she hot?" she asks.

You look at your mom again and she is smiling a bit oddly. Maybe she realized what just happened. "You were great," she says "but would you really kiss girl like that?"

"Of course not, but you are my mom!" you exclaim. They look at you slightly drunkenly. "Are we doing this or not?" Meredith demands leaning against the kitchen counter.

"I guess so, I mean, I've never kissed a girl before. How would I know how to do it? Isn't teaching me the whole point of this?"

"That's okay," your mom says. "You're doing fine."

"Why don't you kiss her again and see if she likes that better? Go on." your aunt prompts.

"Okay," you say "Okay". You look at her sitting there in her neat skirt and blouse, peering at you from behind her glasses. She is just some good-looking older woman sitting at a bar, you tell yourself. You like older women. Everything is fine.

You lean in and kiss your mom like you mean it this time. She kisses you back. After a small adjustment it feels quite nice. Although it is quite hard to forget that you're kissing your mother. Her lips are nice and soft though.

Your mom is a bit flustered after the kiss. "I think I'm getting a little drunk," she says. "Let's stop for now."

Your aunt laughs. "You're getting sloppy" she says. "I do remember times when you really could hold your liquor. But we are not stopping now. We've barely started" She smiles wickedly, and you recognize that she has an expressive face with full lips and those lovely eyes. You wonder if you should stop drinking before she start noticing other things about her.

Your mother looks at Meredith and back to you. You look at them both. The feeling in the kitchen feels slightly electric for some reason.

"Look at Suzy. I told you she is hot. I mean she has that naughty librarian look down perfect. Mature, a bit strict looking but there seems to be quite a lot to be found under that shell." Meredith says swaying a bit.

"I know," you say seriously. "My mom is a goddess."

"Well, aren't you just the cutest thing," your aunt says. "I would not maybe go so far, but she is quite stunning." she says earning a dirty look from you mom.

You look at your mom again. She has a slightly assessing look in her eyes, and she looks at you intensely. She clears her throat and says to Meredith "Maybe we should change roles for a bit?"

"Sure." She sits down beside me and says "Ok. Flirt with me a bit, you can do it."

You look at her and she smiles at you invitingly. "I'll do it," she says. She leans in and gives me a quick kiss on the lips.

"Shouldn't it be me to take initiative? Or didn't we need to flirt first?" you ask Meredith.

"Nah, just could not resist." she replies earning another look from your mom.

"So," you say to your mom and aunt. "How do I flirt with her?"

"Just talk to her," your mom says. "We'll help you."

"Right. Right. You look really beautiful tonight." You say to your aunt and look into her eyes as you understand that is the thing to do when flirting.

She really is a good-looking woman. She is dressed more colorfully than your mom. She is not formal in her tights and sweater but is still surprisingly classy. She has the same beautiful eyes as your mom but has smaller chest, not that there is anything wrong with it.

Are you really thinking this? The doubts ring in your head. Maybe it's good for the practice to try to look at her too like she was someone you just met - Meredith.

"Thank you," she says. "I feel pretty too." Then she giggles a bit.

"You really are beautiful," your mom says to her. "I think you inherited all the looks in the family."

You look at your mom. You notice that she is staring at you, and you look back at her. You both blush for some reason.

"Mom... Suzy... You are good looking too. I mean really." you say to her "You are just beautiful in a different way."

"Thanks," she says. "I'm glad you think so."

"I'm sure you've heard this before," your mom says to Meredith looking at her up and down. "But now that I look at you, you're really hot."

"Thanks. I'm flattered. You've always praised my looks." your aunt says with a somewhat strange voice. "You have never really been jealous of me, have you?"

"I haven't seen you with short hair before," your mom says bypassing the question. "It suits you."

"I had it cut shorter for a wedding," your aunt responds. "I was a bit unsure if it would look good."

"I'm glad you cut it," your mom says. "I've always liked you more with short hair." Something that you do not understand is happening between them. They've always been very close, but this feels different.

"Hey, you two. Wasn't I supposed to flirt with you? Not that you are doing a good job by yourselves." You interrupt. They look at each other, giggle a bit and then look at you.

Your mom clears her throat a bit self-consciously "You're right, we should continue."

"Ok. Where were we? Other than getting new drinks." Meredith says lifting her empty glass.

"I was flirting with her." you remind them.

"Yeah, but you weren't doing a good job," your aunt replies.

"I'll try harder," you say. "You, on the other hand, are doing a great job."

"Thanks," she says. "I am feeling better now. The drinks really help." she says and laughs somewhat drunkenly.

"Yeah, but you didn't seem to be enjoying his attention," your mom says.

"We really did not do anything yet. She kissed me and then we got onto a sidetrack." you point out.

"Right. Let's get back on the track then." your mom says. "At this point start a conversation and figure out if she likes you."

"Ok," you say feeling confused. "What should I do now?"

Your mom looks at you despairingly. You know the look all too well. "Converse with her. It should not be that hard" she says. "Just talk about something."

"Ok," you say to Meredith. "Anything you want me to talk about?"

"Anything. Just don't make a big deal of it."

Thinking a bit and coming up with nothing you almost give up. "How about ... talking about the weather?" you try "Or news?"

They look at each other and sigh. " Let's just skip the conversation. We can always get back to it. Let's imagine that you now know that I am is interested in you" your aunt says.

"How would I know that?" you enquire. "I've never before known if a girl likes me. That is why we are in this situation after all."

Meredith thinks about it a bit and tells you "There are signs, she laughs at what you are saying, mirrors your movements and licks her lips. She also looks into your eyes when you talk. There are others as well. Depends on the girl, really."

You gather some courage - maybe Dutch - and start discussing with her about all sorts of things, your work, her interests. The conversation flows surprisingly well. Your mom points out the signs that Meredith is making, and you catch on a bit. During the conversation you find out lots of things about her that you did not know. It almost as if a new person is revealed from under the role of the funny aunt that you had given her.

"Alex, I have to say that you are doing quite well. You really are a handsome, polite boy. You just need some confidence and girls will fall for you like nothing." Your aunt gets up, stretches a bit and goes to the drink cabinet. You cannot but notice the movements that her body makes when she stretches, and you realize that you are staring.

"I like it when you call him Alex," your mom says approvingly.

"I like calling him Alex too," your aunt says. "I think it sounds cute. Alex. She picked out a good name. Suits him well. Strong and sensitive." she says a bit sadly.

"It almost makes me feel like you're dating my son. Not that you are." she adds hastily and picks up the drink given to her.

"It does..." your aunt muses looking at you under her lashes.

"I'll go to the little girl's room," your mom says. "Then we can start role-playing again."

Your mom walks out of the room leaving you alone with your aunt who looks at you with an estimating look in her eyes.

"So, what would you want to learn now?" your aunt asks after a moments silence.

"I have no idea," you say. "Maybe we just sit here and wait for mom to come back."

"That's not very exciting," she replies and purses her lips.

"No, I guess not but I don't know what else to do. You are the ones that are supposed to teach me."

She sits a bit straighter. You can't help but notice how that pushes her breasts against her shirt. "Let's continue then. Now that you have my interest and have kissed me, what happens next?" she asks you.

"If we were in a bar," you say. "I would take you home. It would be easier to have a discussion there."

"You're quite right. That is the classic move," your aunt says. "Let's pretend you are taking me to your home."

You both get up, walk out of the kitchen and down the hall.

"So, this is where you live?" your aunt asks curiously. "I like it. I've actually never been here before."

"Yeah, it's pretty nice for the price," you say. "I'm glad you like it."

There is not much else than the kitchen, the living room, single bedroom, and the bathroom so the tour is over quite quickly.

"It's cozy," she says. "And it's got a nice view of the lake."

"Oh, yeah," you say. "The lake is right outside. I like to sit on the couch in the evenings and just look at it."

You have ended up into the living room as your mom comes back into the room, carrying new drinks.

"Here you go," she says happily. "Drinks are on me."

You sit down on the couch, Meredith on the other side and your mother on the other side of you. The couch isn't too big, and you sit very close to each other. You feel the heat from their thighs against yours and you realize that is making you aroused. You try to calm down and sip your drink to cover the sudden surge of some urge inside you.

Your aunt begins again "We'll switch the roles again. Suzy is the girl that you have brought home. I'll give you hints and concentrate on this drink." She gets up and looks at the view.

Your mom puts her arm around your shoulder and squeezes. "It's going to be fine. " She assures you. "She'll help you if you need it. But you've been a good boy - student so far."

Your aunt turns around to look at you on the couch. "Now, since you have kissed her and taken her home, what should you do next?"

Giving your mom a sidelong glance, you are amused to find out that you have cold feet. The training seems to be working at least in that sense. "I guess I'll see what she wants to do." you say passing the ball.

"Yeah, but what if she doesn't want to do anything?" your aunt asks. "What then? You need to take initiative. If she looks receptive you should...?"

"I guess I could kiss her again." you hazard. You are still feeling awkward about the whole kissing-your-mother thing. Even if it felt very nice.

Your aunt says, "Good thinking." She walks over to you. "You were doing a good job until you stopped kissing her."

"We did the kissing thing already, right? Didn't we? I think I know how to do it now." you say, not that you would be completely against it.

"Well, you can always try to get a little handsy," your aunt suggests. "It's not that hard."

You look at your mom who you realize is quite drunk. "Are you really ok with this? It feels weird as you are my mom." you say to her.

"I'm fine with it," she says. "It's okay for you to experiment. Experimenting is good, right Meredith? I'm just happy that you're trying to learn how to date. You'll never get a girl otherwise." She rubs your shoulder, and you notice that she still has her arm around you.

"You're right," you say. "I am experimenting. I guess I'll just go ahead and kiss you again."

You turn towards your mom who is already turning her face to you. You tentatively kiss her. You smell alcohol in her breath and her lips feel good against yours. You almost get lost to the feeling.

"Wow," your mom says pulling back. "That was great. I mean you did great. You did it just right."

"What?" you ask a bit surprised at her reaction. "Did it really feel good?"

"Yes," she says. "It did feel good. In fact, you could kiss me more. To get it just right." You realize that your aunt looks at her with an odd look on her face.

"What?" you ask noticing her raised eyebrows.