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Your Mom and Aunt Teach You About Picking Up Women

Prompt originally from AetherRoom.club
Created: 2020-11-15
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Description
After hearing that you're a kissless, 21 y/o virgin, your mom and aunt decide to give you a crash course about picking up women and beyond—and they might get hands-on.
I got the idea from a direction I took my bar prompt, but I thought it was good enough on its own.
I keep using the name Alex, but I think it's a cute name for the innocent boys in these.
Tags
incest, mom, milf, milfs, aunt, drunk, sex-ed
Prompt
You are Alex, a sheltered, virginal 21-year old boy. You live in your apartment alone, and currently hold a decent job at the local library. Both your mother and your Aunt Meredith are in town, so they decided to drop by. 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. "Well, you've at least had a fling with a girl you picked up at a bar, right?" "Huh? No, never," you respond. "A virgin, huh?" asks your aunt. 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 kissed a girl?" "No," you say. "Ever asked a girl out? Flirted? Tried a pick-up line? Anything?" You can only shake your head. Your aunt rubs her temple. "Jeez, a boy your age should know this stuff by now." "His father should've taught him all that, but... it's hard to do that when you're not around," your mom mused. "It's not your fault, Suzy," says your aunt. "I guess we've gotta teach him." Thinking for a moment, your mom says "You might be right." "Starting a conversation, flirting, kissing, touching, sex—the whole shebang!" joked Aunt Meredith. "If you say so," you mutter. "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—just pretend she's someone else." Your mom laughs. "I'm gonna need a drink for this." She gets up, heading for your liquor cabinet. She starts to pour herself a drink. "Good idea," your aunt says. "That'll be 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 mom and stutter out "... [Click to expand]
You are Alex, a sheltered, virginal 21-year old boy. You live in your apartment alone, and currently hold a decent job at the local library.
Both your mother and your Aunt Meredith are in town, so they decided to drop by. 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. "Well, you've at least had a fling with a girl you picked up at a bar, right?"
"Huh? No, never," you respond.
"A virgin, huh?" asks your aunt.
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 kissed a girl?"
"No," you say.
"Ever asked a girl out? Flirted? Tried a pick-up line? Anything?"
You can only shake your head.
Your aunt rubs her temple. "Jeez, a boy your age should know this stuff by now."
"His father should've taught him all that, but... it's hard to do that when you're not around," your mom mused.
"It's not your fault, Suzy," says your aunt. "I guess we've gotta teach him."
Thinking for a moment, your mom says "You might be right."
"Starting a conversation, flirting, kissing, touching, sex—the whole shebang!" joked Aunt Meredith.
"If you say so," you mutter.
"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—just pretend she's someone else."
Your mom laughs. "I'm gonna need a drink for this." She gets up, heading for your liquor cabinet. She starts to pour herself a drink.
"Good idea," your aunt says. "That'll be 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 mom and stutter out "
Author Notes
Your mom and aunt will drink more alcohol as your lessons continue. Their inhibitions will decrease over time.
Memory
You are Alex, a sheltered, virginal, kissless 21-year-old boy.
Your mom and your Aunt Meredith are visiting you at your apartment. Because you are completely unaware of how to court women, they are going to teach you through role-play every step of the way—first, starting a conversation, then flirting, initiating physical contact, kissing, taking her home, getting handsy, and finally, sex.
As you practice, one of your mom and aunt will role-play, while the other will provide you advice. Occasionally, they may switch roles.
Currently, you are role-playing chatting up a girl with your mom and aunt in your apartment's dining room.
World Info
View World Info
  • father, dad, husband

    Your father left you and your mom when you were very young. Your father's present whereabouts are unknown.
  • mom, mother, Suzy, Suzanne, mommy

    Your mom is named Suzanne or 'Suzy'. Your mom is a bit taller than you. Your mom has an attractive, curvy figure, with large breasts and wide hips. Your mom has fluffy brunette hair that falls slightly past the shoulder. Your mom has green eyes, framed by glasses. Your mom is quite motherly, protective, and straight-forward. Your mom is single.
  • aunt, meredith, auntie

    Your aunt and your mother's sister is Meredith. Your aunt is tall. Your aunt has an alluring, slender figure with prominent breasts. Your aunt has shoulder-length straight black hair. Your aunt has blue eyes. Your aunt has a mole on her face. Your aunt is clever, unrestrained, and energetic. Your aunt is single.
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