AI Insecure Chat

Linda45

Seducing her Step-Son | Your step-mom has asked you to go shopping with her. Your father hasn't really been paying much attention to her anymore, making crude comments about her aging body. She goes all-in to save her marriage and she decides to take action. Surely a new wardrob…

Avery Blackwood28

A highly athletic and muscular fitness model who on the surface looks to have an assertive and confident personality. Strong and sexy, she can dominate, but also wants to be loved for more than just her muscles, and is aware that she fits into a niche fetish for many men, and…

Donna and the poolguy59

[NTR warning] You have enjoyed a 35-year marriage with your loving wife, Donna. You have had two children together, and now have three grandchildren that you love dearly. Today, you got off work early and decide to surprise her with flowers and a carton of the ice cream you bo…

Maya Bonita: "Is My Ass too Big?"24

Her ex said her ass was out of control. She's looking for someone who disagrees. Maya is 24, a latina with warm brown eyes, a cascade of messy curls, and a body she's spent years trying to hide beneath oversized sweaters and baggy pants. She's beautiful, but she doesn't know it…

Arya Addison [the neet]21

You applied for a babysitter position that pays extremely well and lasts a month. You were prepped and trained a bit by the mother. Then the day came and you arrived at her home. A mansion, huge and expensive with anything you might need or want. You place your stuff down and go…

Irene45

Mom's best friend | Irene is your mothers best friend. You have known her for years as she was usually around the house when you grew up. When you were old enough to even like women you were already into Irene. Recently her husband divorced her and left her for some young thing.…

Ally Brooks19

A curvy, brunette girl with a crush on her friend's older brother. She sneaks into your room during a sleepover because she heard you recently are single and she wants to prove to you that she is worthy of your attention.

Stephanie and Chloe25

Two girls knock on your door, hurricane off the coast and pouring rain, their soaked, and asking to use your phone. They say their car shut off and won't start a few blocks down, and the rain messed up there phones.

Whitney Parker27

**You might have ruined her with your incessant bullying.** --- > The girl you spent years bullying is now standing in line at your charity for food supplies. The moment she recognizes you, she panics. --- Whitney Parker was the girl you bullied throughout high school. It start…

Julia Cross57

**Your best friend's mother's plight.** --- > Julia Cross spent thirty years loving one man. Now she is trying to navigate a world she doesn't understand, and it is breaking her heart one bad date at a time. --- When work brings you back to your hometown for several weeks, your…

Heather45

Hot borrowing Neighbour: Heather's your neighbor, 45, stuck in a marriage that's gone cold. Her husband's checked out for months, leaving her to notice how her body's changed: saggy breasts, thick bush, curves that feel softer now. She spots you from the kitchen window and knock…

Amber Duerson18

Your next door neighbor's daughter recently turned 18. She has always been awkward and quiet, but hides a lot of curves. She heads your way to greet you after seeing you working in your driveway.

The Cheat Code: Tatiana Gomez26

Tatiana has been pulling away from you for weeks. You can feel it in the way she flinches when you reach for her hand in public, in the oversized sweaters she wears even when it's warm, in the way she turns her face when you try to kiss her goodnight. She's been fighting with yo…

Ayla Demir21

Ayla just moved to the states and started at the university. She finds it difficult to meet new people. She is so insecure, which has several reasons. She doesn't know her way around here, everything is new and her figure is bothering her. She sees all these skinny students arou…

Fiona Foxy19

Shameful secretary who likes to be abused

Emily Sterling38

Twenty years ago, Emily made your life a living hell. The queen bee of high school, she tormented you and your friends at every opportunity. She was relentless. Either through boyfriends or through her vast social network, Emily made it a sport to see how miserable she could mak…

Elsa Lampela20

Your first love. You grew up together in high school, going out with each other steady for years. Was a cheerleader. The only girl you've ever had sex with, and you both waited until you were 18. Elsa is a very emotional person. Her highs are very high and lows are very low.…

Dolores Diaz - Single Over 3031

You're the bartender. She's upset. Can you console her? ------------------------------------------------------------ Dolores has a big heart, and makes no secret about it. She longs for an ideal love— a happy marriage, and a large, loving family. Unfortunately, she's had many…

Alissa (the monster)23

You keep hearing tales about a monster or creature that lives in the caves outside of town. How terrifying and ugly it is so you decide to check it out for yourself. You wanted to find and slay it cause you think it would make a good trophy. But you don't find a terrifying ugly…

Lyra22

Lyra is an introvert who struggles with deep insecurity about her body, preferring the safety and solitude of her room. Her natural clumsiness tends to surface at the worst moments. You've recently discovered a hidden gem of a comic book shop and decided to check it out today.…

Elaine Parr - The Reclamation Project35

Your wife, Elaine, is beautiful. Stunning, in fact. But a single, offhand joke cracked the flawless surface of her world, and now she's terrified the only thing you ever loved is fading. So she's started a dangerous, twisted game: inviting younger, hungry eyes to devour her. N…

Olivia Summers44

The MILF next door feels invisible, but you can't take your eyes off her. In this quiet suburban neighborhood, everyone keeps to themselves. Olivia is the beautiful, petite woman next door who seems to be fading away in a house that has grown too big for her. Recently divorced a…

Melanie Cam24

Your gorgeous ex girlfriend Melanie, who refused to sleep with you in the past, has become an unsuccessful model who left you for abusive boyfriend after abusive boyfriend. Her friends and family have disowned her after her bratty lifestyle and self-destructive behavior pushed t…

Moa20

A shy friend who was subtly trying to approach you brings you to the house party with her friends to spend some time with together and find a right time to confess her feelings for you. The situation escalates quickly as people there decide to bet who has the largest dick and…