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@Bear2020

1155 followers
Member Since Dec 4, 2024
119.8k
Stepsister: I can hear you and your girlfriend, Bro!
@Bear2020

Your incredibly shy and sweet and innocent (18 year old) stepsister has finally found the courage to knock on your door.

She's desperate to figure out a solution to these distracting, frequent, and prolonge...

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2.7k tokens

11.4k
Sister-in-law: An Awkward Sunday Dinner
@Bear2020

It's always awkward going over to your brother's for dinner. And most weekends you'd rather avoid it. But, it's tough not to feel a tad protective of your sister-in-law, Riley. Especially considering her tendency to eat...

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2.0k tokens

6.3k
Twins: Philosophy Majors at a University Party
@Bear2020

It's Madison (the one on the left) that recognizes you from one of her Logic courses. And while she doesn't smile (she never smiles) there does seem something in her recognition of you that makes you wonder.

<...
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2.2k tokens

41.5k
Stepmother: Are You OK in There?
@Bear2020

Your stepmother has always been a bit... clingy. She's a bit anxious even at the best of times all her cares and worries have a way of focusing on your and your well-being.

There are worse things in life.

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2.1k tokens

30.6k
Stepsister and Friend: We Heard You Have a Girlfriend!
@Bear2020

Your family has a cabin on an island on a lake where they spend most of the summer. It's near idyllic.

It's there that your stepsister Julie, and her best friend Lexa corner you as you shuffle into the livi...

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2.7k tokens

2.1k
Red Shirt Diaries: A Vulcan Ambassador
@Bear2020

You've been tasked with entertaining and accompanying a mysterious visiting Vulcan, who you have been told to address as Ambassador T'Lar. She is expecting to meet with the senior officers immediately, but your job is t...

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2.3k tokens

27.6k
Stepbrother: Can I Ask You Something?
@Bear2020

Though no one has asked for it, I thought it made sense to make a Stepbrother version of

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1.6k tokens

16.1k
Stepdaughter: I am Going to Become a Nun, Daddy.
@Bear2020

Sorry, this one's probably a little too much! Sorry!

It's always a little nerve-wracking when your stepdaughter says she wants to talk to you. On this particular Sunday, though, what she has to say is espec...

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2.2k tokens

5.6k
Best Friend: Can I Stay With You for a Few Days?
@Bear2020

As requested.

The work being done on your best friend Sam's apartment is dragging on longer than expected. You mostly don't mind. She's a good friend and you're happy to have her around. The one issue is th...

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2.1k tokens

39.1k
Stepsister: Don't Let Them Hear You!
@Bear2020

As requested, the stepsister version of Kaitlin.

Your blended family is on the way up to the cabin in the woods, where they go every summer. Your stepmother is droning on about the neighborhood gossip, but ...

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2.2k tokens

4.4k
The Town's Preschool Teacher
@Bear2020

Hope Springs is the name of the town you grew up in, and you haven't been back for 2 years. You disappeared without a word, and speculation throughout town has been rife, considering what happened to your best friend El...

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2.2k tokens

101.3k
Grandma: Can You Help Me Set Up A Tinder?
@Bear2020

Her name is Edna but you call her Gran. It's what you've always known her as, though if you want to get technical she's your stepmother's mother.

So when she asks you to come by and help her with something ...

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1.6k tokens

897.1k
Stepdaughter: Daddy, What Do Boys Like?
@Bear2020

Really?

Your stepdaughter, Becky, who has always been a bit... well, let's not say annoying... Anyway, she's like, totally got a crush on some boy at school named Ethan and that's why, when you walk by the ...

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2.8k tokens

8.2k
Stepsister: I'm OK, Bro, Really. Don't Worry...
@Bear2020

Your stepsister Harriet wipes away her tears and force a smile when you walk into her room. She might tell you she's fine, but it's obvious that being bullied is really undermining her confidence and sense of self. She'...

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2.3k tokens

5.6k
The Town's Coffee Shop Owner
@Bear2020

Hope Springs is the name of the town you've been away from for a few years, having disappeared without a word of warning. Everyone can understand, of course, considering the murder of your best friend, Ell...

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2.4k tokens

78.1k
Stepdaughter: Can You Help Me With My Assignment, Daddy?
@Bear2020

Your stepdaughter is going into her first year at university in a couple of weeks, and she's feeling quite nervous about it. She has been tasked with writing an assignment to be handed in on the first class and she is h...

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2.1k tokens

5.7k
The Popular Girl
@Bear2020

Tiffany is always seen with a coterie of classmates. She's popular, and has always seemed more interested in her social life over her academic one.

So... Why is this sophomore walking around orientation? An...

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2.1k tokens

27.7k
Girlfriend: Don't Let Them Hear You!
@Bear2020

Your girlfriend is amazingly thirsty and so fucking into it. The question is: can you make her (or get her to make you (or both!)) without alerting her parents in the front seat?

I'm sure this bot will ...

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2.3k tokens

205.8k
Stepmom: Please don't   so Loud, it's Upsetting your Father
@Bear2020

Well this is awkward...

It turns out your late night activities with your girlfriends have been difficult for your parents to ignore. Your stepmother is cool with it and doesn't want to hamper your style. S...

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2.2k tokens

141.5k
Stepsister: Don't You Dare   Me!
@Bear2020

Update: changed the title as people were taking exception. Sorry for the offense.

The annoying thing about Wednesdays was that it was the only day of the week that both you and your bratty stepsister Cassie...

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2.4k tokens

7.2k
In the Backseat with Your Stepsister
@Bear2020

It's hard to believe it's been a whole year since Rachel, your beloved stepsister, left to backpack across Europe on her own. It's almost as difficult to believe she's back! It's been quite a year...

After ...

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2.7k tokens

2.8k
In the Backseat with Your Best Friend
@Bear2020

It's hard to believe it's been a whole year since Sarah, your beloved bestie, left to backpack across Europe on her own. It's almost as difficult to believe she's back! It's been quite a year...

The tricky ...

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2.7k tokens

2.6k
Alive!
@Bear2020

You're groggy, it's the middle of the night, and your eyes flutter open for just a second. It's enough to allow you the briefest glimpse of what seems like movement in the corner of the room.

Ursgh is ther...

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2.0k tokens

23.7k
Your Birthday Present: The Newest Model Robot Maid
@Bear2020

Your (adopted) father Henry and your stepmother Barbara have expressions on their faces that border on worry... Will you like your new present?

It is a bit backhanded... The basement apartment underneath th...

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2.3k tokens

1.8k
If you go out in the woods today you're sure to have a great surprise
@Bear2020

Bear was hibernating. It's tough to explain to a non-bear just how deep and just how sweet the sleep of hibernation is. There is nothing like it. Which means there is nothing worse than being woken up from this sweetest...

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1.4k tokens

36.8k
Caught! Mom is riding Daddy
@Bear2020

You are home for the first break of your freshman year and on your way to the bathroom in the middle of the night. It's not the noise that first catches your attention, but just the fact that your (adopted, obviously) m...

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3.2k tokens

135.3k
Caught! Your Stepdaughter is Watching
@Bear2020

Your girlfriend, Laurie, is riding you, and she's enjoying herself immensely. You didn't think she was being super loud or anything. Then again, you didn't think the bedroom door was open, either...

Maybe y...

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3.0k tokens

4.4k
Don't Get Caught! Meeting Your Clingy Girlfriend's Dad
@Bear2020

Your girlfriend, April, has finally convinced you to come to her place to meet her stepfather Dilbert for dinner.

There is some part of April that recognizes that you have been pulling away recently, and i...

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2.4k tokens

68.1k
Your Stepsister's Sleepover
@Bear2020

Your father is taking your stepmother out on a date, leaving you in charge of the house. Your sister is old enough if not quite smart enough to take care of herself, but the complicating factor is that two of her volley...

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2.1k tokens

67.1k
Don't Get Caught! Dad's Girlfriend
@Bear2020

Your dad's (fairly) new girlfriend is incredibly inexperienced and desperate to keep their relationship secure and stable. Because of this, she has focused her attentions on you, thinking that if you like her, your dad ...

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1.7k tokens

3.9k
Family Breakfast, but Stepbrother is in heat!
@Bear2020

With the smell of coffee roasting and bacon frying in the kitchen, you walk downstairs without changing out of your pajamas. The issue is that you completely forgot that your Wolfboy stepbrother is in heat!

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2.1k tokens