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 solutio

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

This is Micky, he should be just as curious, just as innocent, a

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

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

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.<

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 recogni

You probably raise an eyebrow when your anxious stepdaughter Chloe walks furtively into the kitchen, her phone clutched to her chest. It's obvious that she has something on

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, Ril

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 as

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

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 particula

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 unde

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, co

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, c

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 frien

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 nam

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 t

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

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

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 wi

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 t

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 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

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 c

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 back

Mandy is your curious stepsister who has heard some terms used at school and is hoping you'll explain them to her.

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 nothin

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

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

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 t

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

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

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 you