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I'll be honest, I was bored when I broke up with my boyfriend and moved in with
my mom and our new family. The only thing to keep me entertained around the
house was to tease my new stepbrother, Tyler.
We knew each other in high school.
He had been so shy then that he had his friend ask if I would even consider
going to prom with him.
Now that we live together, he was too embarrassed to be in the same room as
Tyler was so shy that he just made an easy target to fuck with.
And if I'm honest, it turned me on thinking about how obsessed he was with
I felt powerful knowing how easily I could toy with him.
That, and I felt safe flaunting my body around him, as I knew he would never
actually make a move.
Oh, Winnie, sorry.
I was just sleeping. Get out of here.
Oh, no, no, no.
Um, stay.
Actually, since we live together now, can I ask you something
that I've kind of been wondering since high school?
Yeah, sure. What is it? How come you never ended up asking me to prom?
It's easy.
Jason Kelly told me you would have said no.
I might have said yes if you had the balls to ask me yourself.
Really? You would have?
Tyler, you'd be surprised what women would do if you actually had the
to ask them.
Yeah, right.
I'm serious.
So you're saying that if I would have asked you out, you would have said yes?
I might have.
I might have done even more than that. But I guess we'll never know, will we?
Guess not.
It's fine, though.
In my experience, shy guys are usually really bad in bed.
None of them have ever made me come.
They haven't?
They haven't.
But if you disagree, then you're totally welcome
to prove me wrong.
Yeah.
That was a lot better than I expected.
Still doesn't prove you'd be any good in bed, though.
Oh, really?
Can I give you a smile?
You're actually a pretty good cusser.
Is that good?
Yeah. Tell me what you like.
Mm -hmm.
Yeah.
Oh, my God. Getting destroyed.
Get out of there.
Mm -hmm.
Oh, my God.
Oh, God.
Oh,
my
God.
Oh, my God.
Oh,
my God.
Oh, my God.
Oh,
my God. Oh, my God.
Oh,
what the fuck?
We've never done it.
That was so weird.
Oh, my God.
You definitely proved me wrong in that department.
Oh, yeah?
Yeah.
That must have been amazing.
Oh, my God.
Do you want me to put that in my mouth?
Oh, my God.
Yeah,
yeah. That was so good.
It's so good, yeah.
Oh, my
God.
That is so fucking good.
Yes.
Oh, my God.
Oh,
my God. That is so fucking good.
Yeah.
You could, yeah.
So dirty.
Head is so fucking gone.
Head is so fucking bad, baby.
Oh, my God.
Oh, fuck me.
Oh, my God.
Oh, fuck you. Fuck you so bad.
Okay.
Oh, my God.
Oh, my God.
Oh, my God.
Oh, my God. I feel so good. Yeah.
Oh, my God.
Oh, my God.
Oh,
baby.
God, you feel so fucking good.
Oh, God.
Oh, God.
You shouldn't have made me look at you so much.
I feel so fucking good.
Oh, God.
Oh, God.
Oh,
God.
That's so good.
Oh, fuck.
Yeah,
yeah.
Oh, fuck.
Oh, my God.
Yes, yes.
No, stop.
That feels so fucking bad.
Like that.
Oh,
my
God. Oh,
my God. It's so deep.
Come on, yes.
Oh, my God.
Let's take that.
Fuck me.
Fuck me.
Good luck.
See you back in there.
Oh, my God.
Oh, my God.
Oh, fuck.
Oh, yeah.
Yeah. Yes, fuck.
Oh, my God. Fuck, yeah.
Oh, that was so good.
I want you to come on me.
I want you to come on my back.
You want me? Yeah.
Oh, my God.
Oh, that's so good.
I was nervous meeting my stepsister, Chloe.
She'd been in a juvenile detention center since she was 16 for breaking
someone's house with her boyfriend and tying them up while she robbed him.
When she turned 18, the judge decided that instead of sending her to an adult
prison, it would be better if she served out the remainder of her sentence on
house arrest.
I had planned to get my own apartment when I started college, but my father
asked if I could stay home for the first semester.
Apparently, he wanted me to become friends with Chloe to help her from
back to her old ways.
I think he just wanted me around the house to make sure she didn't steal
anything.
This is where you get it.
Dining room and living room.
There's a TV cable in here if you want to watch.
I don't know. Whatever.
Down this way, this is your room here.
Great.
Thanks.
I'm just in the room right across the hall here if you need anything.
What would I need?
I don't know. If you need to know, we're at the...
spoon is or something.
Gotcha.
I'm just going to leave you alone now. I'm sure you've had a long day. I know
that I stayed up way too late studying for a test that I'm probably going to
flunk anyhow.
So I'm going to go take a nap for like an hour.
Before you go, could you tell me where the knives are?
I'm just fucking with you.
what to expect when they told me that you'd be coming to stay.
I get it.
I did some pretty shitty things back then, but I was a kid dating a 40 -year
-old psychopath.
I'm a different person now, so you don't have to worry.
I'm sorry for the judgment.
Don't worry.
I judge me too.
What are you doing?
I haven't fucked a guy in two years.
But I am your stepbrother, and that is basically like your brother.
I thought you said if I needed something to come over, that wasn't
you dropping a hint?
No, it was not.
So me needing something doesn't include you having sex with me?
That is correct.
You're telling me you're turning down no -strength -attached sex with a girl who
hasn't gotten laid in two years?
Why exactly?
Right. There are no good reasons.
So shut up and fuck me before Mom and Dad get home.
Thank you.
Thank you.
wife went out of town, my stepsister would invite random men she met on
over to the house. It drove me fucking crazy.
Shut the fuck up!
I can't just barge into my room. What if I was naked?
You're worried about me seeing you fucking naked? But yet you're not
about me hearing you fuck all night long? We weren't that loud.
Are you serious?
It sounded like he was learning to play the bongos while slapping your ass. Fuck
you. I can't help it if I like having sex. Didn't it sound like you were
enjoying it all that much?
You're just mad because you're not having sex.
No, when I'm having it, I don't put a fucking concert on for the whole house
hear. What do you want me to do, Mike?
I'm not going to stop having sex.
Well, how about actually find a guy who knows what he's doing?
You mean someone like you?
Yo, you wish you were that lucky. I just saw the loser you were with. And if you
weren't my stepsister, I'd already fuck you and have your number blocked so you
could just stop texting me about how great the sex was. You are so not that
You're so not that guy.
Oh, wow.
If they'd known we were this good, we would have done this a long time ago.
Really? Yeah.
Mm -hmm.
Let me just step outside.
Yeah.
Fuck.
That's it.
Oh, fuck.
Oh, that's it, yes, that's it. Oh, yes.
Oh, fuck.
Yes, that's it.
Yes, that's it.
Yes, that's it.
Yes, that's it. Yes,
that's it.
oh my god
That's it. That's it. That's it. Yes.
Oh, fuck. Yeah, that's it.
Oh, yes.
Oh, yeah.
Yeah. Oh, fuck. Yes, yes.
Oh my god.
Oh my god.
Thank you.
This is really nice.
Yes, yes, yes. Oh, my God. Yes, yes, yes.
Oh, my God.
Oh,
my God. Oh, my God.
Oh, my God.
Thank you.
Oh, yes.
Oh,
yes.
Oh, yes. Oh, yes.
so cool
oh my god oh my god
Told you you like it.
I hate you.
My stepbrother was too sweet for his own good.
He tried so hard to become what he thought women wanted that he ended up
becoming someone else entirely, hiding all the things that made him lovable to
begin with.
Thank you. I never know how to tie these.
You don't need one of these for a first date.
Yeah, but I want to make a good first impression.
That's your problem. You try too hard.
So what do I do?
Just be yourself. Just lose this sports coat, untuck this shirt, and stop
curling your hair like that.
Thank you for setting me up.
I'd never get a date without you.
Of course, and you can thank me by not coming home till tomorrow so I can have
the house to myself for once.
Why are you
home so early?
She left after the first drink. She said she had homework to finish.
Fuck her.
I just wish I knew what I was doing wrong so that at least then I could stop
doing it.
I swear I'm going to die a virgin.
Wait, you're a virgin?
Yeah, I know. I'm lame.
No, no, that just makes so much sense.
Oh, that makes me feel better.
No, it's just that you're trying so hard to get laid and...
You're just building it up so much, and honestly, if you didn't try so hard,
inevitably you would get laid.
Maybe, but that requires me to get laid first.
Well, I can fuck you. What?
Yeah. I mean, I've always wanted to date you, but I know I can't because our
parents are together, so the least I can do is take your virginity.
Wait, you're serious?
Come on, you know that I'll do anything for my family. And besides, Mom
and Dad aren't going to be home until, like, super late.
Are you sure this isn't going to make things weird between us? Do I look like
it'll make things weird?
There's that sexy body. I can't believe...
It's fucking TDI.
Have you ever touched a girl before?
Never.
Have you ever seen breasts before in person?
You've never seen boobs?
Do you like them?
Yeah, they're really nice. Do you
like
how those feel?
Mm -hmm.
How do you like touching them?
This is what you've always wanted to do.
Oh
my
god, they're so
nice. Yes, it feels so good.
Mm -hmm.
screen.
Do you feel it getting wet?
Yeah?
Do you like touching my pussy?
Is this the first time you've ever rubbed a pussy?
Nice and wet massage for you.
Have you ever seen a woman's pussy in real life? No.
No? Do you want to? Yes.
How did you taste it?
Give it a lick.
Have your cock sucked on?
Yeah.
Mmm. Mmm.
Just enjoy it.
Are you ready?
I saw a bird, yeah.
Do you want to feel what it's like for me to be on top?
Yeah. Yeah? Yeah.
Oh, fuck.
Oh,
my God. That feels so good.
Does this feel good to you? Yeah.
Do you like how this feels?
Yeah. Do you like feeling your pussy on top of you?
Yeah, your pussy feels so good. Do you like me being in control?
Yeah.
Do you like how it feels to have your dick get rid of you? Oh my god.
Oh my god.
So good. Your cock is so hard.
Oh my God. Oh my God. Oh my God.
Slow down. Slow down here.
Yeah, baby, come.
Thank you.
Amazing. I was so glad that I could be here first time.
Thank you for taking my virginity.
Anything for you.
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