Uh, Hailey? Thank you, I'm a second. Yeah, what's up? Um, well, a girl from school invited me over to her house next weekend. She said her parents aren't going to be there. Oh, nice. Yeah, I think she wants to have sex. But I've never done that before....
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Uh, Hailey? Thank you, I'm a second.
Yeah, what's up?
Um, well, a girl from school invited me over to her house next weekend. She said her parents aren't going to be there.
Oh, nice.
Yeah, I think she wants to have sex. But I've never done that before.
Okay.
And I kind of told her I did.
Yeah.
So, I'm a little nervous and I was hoping maybe you could help me. I just figured you have more experience.
Sure.
Maybe you can tell me some tips.
I guess I could try, but...
Well, like, I've never even seen a girl naked before, so I need a lot of help.
Okay, yeah, I can help you, but can we just go back to the fact that you're a virgin?
It's not funny.
It's cool, brother, you're still a virgin.
Aww.
Okay, sit down.
Okay, what's her name?
Andrea.
Andrea?
Yeah.
Okay, that's the same age?
Yeah, she's a couple months older than me.
Older girl, okay. Um, okay, pretend I'm Andrea.
Ooh, Jake!
What are you doing? Isn't this scene a little inappropriate?
You're my sister.
Yeah, I'm just your sister, why is it better?
I guess it'll help.
Yeah. Okay, anyways.
Hey, Jake. Um, my parents are away for the weekend. Would you want to come over?
Yeah, sure.
Okay, we're not gonna do that. You're so awkward.
I'm just nervous.
Okay. Okay, how about this?
Mom and Dad aren't gonna be home for like another hour.
This'll work, don't be weird.
But, just tits. These are her tits. What are you gonna do?
Uh, touch them, I think?
More confidence!
I would touch them.
Yeah.
Like, that.
Okay, I'm still your sister.
I'm sorry, I thought like you weren't gonna say anything.
Okay, I guess that's my fault. Okay, alright, sure, whatever.
Okay, um, sorry.
Just touch them.
I've never touched them like this before.
How does it feel?
It's really nice.
Yeah?
Yeah.
Okay.
So now what though?
Well, this is where you would make a move and maybe take her clothes off first.
Um, and then, do you like, do you know positions and stuff?
No.
Oh, you don't know anything. You've never watched porn?
Yeah, but I thought it was all fake.
Kind of, but you can learn stuff from it.
Do you know that stuff?
Yes, I've had sex before.
What are we working with? Now that you've seen my tits, what you got going on?
You wanna see my dick?
Yeah.
That's not too weird.
You just touched my tits. I don't think you could get it.
Okay.
Well, it's not hard or anything, but I think it's pretty big.
Alright, you need to have more confidence taking your pants off. That's it.
Can I take my underwear off too?
Um, no. Just take the pants all the way off.
You look kind of hard to me.
But I don't know what to do with it.
Okay, I will help you a little more, but you can't tell anybody.
Probably do something like this.
And probably move it a little.
And since it's your first time, you're gonna want to come really fast.
But you need to like...
You don't like it if I do?
Um, no. She might laugh at you and that's embarrassing.
Oh, I don't want to.
Yeah, but if you already told her that you've had sex, it might help if you have sex.
Like with you?
Step-sister.
Yeah, but...
You're not related.
I won't tell anyone. Are you?
No, I won't tell anyone.
Okay, then it sounds like it would be good.
Okay.
Do you want to do this?
Do you want to do this next?
Okay, well, I'm assuming you've never had a blowjob before.
You want me to give you one?
You're supposed to hold my hair.
Oh, to mess it up.
Yeah.
Thank you for teaching me this.
Mm-hmm. That's what big sisters are for.
Yeah, you are kind of big.
You think she'll like it?
Yeah.
I think I might go...
Oh, okay. All right, let's move on to something different then.
Okay, well...
Um, well, maybe you can take my shirt off. Just pull one side.
Or both.
Yeah.
Try it on you.
Mm-hmm.
Use your tongue.
You're pretty good at that.
Yeah, just like that.
Mm-hmm.
Okay. Um, now, which, like, positions do you know?
Doggie and girl.
Like the one where you lay down and then aim on top.
But I don't know what it's called.
Missionary?
Yeah.
Okay, what's, like, your favorite one to watch?
So, cowgirl.
So, which one, like, would you want to try first?
Try one?
Yeah, let's try one.
Well, the cowgirl one sounds good.
Okay, yeah, we can try that.
But the thing with that is you don't really start out with that one.
You have to get the girl, like, aroused.
Well, you could eat her out.
Try it on you.
Yeah, I can try it.
Do you, like, know what to do, though?
Okay, over here.
If you really want her to like it, you're gonna, like, kiss her leg.
And then you're gonna, like, kiss right here.
And then you're just gonna, like, look around and do what feels right.
If you want to.
If you want to.
Yeah, like that.
Yeah.
That's what happens when the girl enjoys it.
She gets wet.
Yeah.
Roger, that feels good.
Okay, now that I'm ready, we can start in missionary.
And then we can switch.
Okay.
I won't make you go too long, but just don't go, yeah.
Just don't go too fast so you don't cum too fast.
Because you're gonna, you're gonna feel like you need to cum.
Um, did you, like, spit on your hand?
Uh, no.
You should do that.
You always want to make sure that your dick is wet and that she's wet, too.
Okay.
And sometimes she'll need lube.
Um, but not always.
Okay.
So do I just?
You just put it in.
Pretty big.
Are they always tight like that?
Usually.
Yeah, that does feel really good.
And if you need to pull out so you don't cum, you should just do that.
So that you'll last longer.
What do I do when I have to cum?
Um, well you should wait for her to cum first.
And then, um, she'll tell you where she wants you to cum.
Yeah?
Yeah.
It's okay.
Take a break if you need.
Do I just put it back in when I'm ready?
Yeah, put it back in.
I feel a little dry, so you should spit on it.
It feels really, really good.
It's so big.
I'm supposed to do it?
Yeah.
Pretty like in sync with me, so that's good.
Because you want to stay in sync with the person.
I feel so good.
Okay, you want to switch?
Yeah.
Well, you can do cowgirl.
Put your leg down.
Feel good?
It's so deep in there.
Should I, like, put your boobs, too?
Yeah.
It feels really good.
That's for me, too.
If you want, you can, like, raise your legs a little and you can, like, fuck me.
Yeah.
You're so deep.
Oh my god.
I think I'm going to come.
Let's switch.
Which one do we do now?
We can do doggy.
I'm going to go here, and you're just going to put it in.
I'm going to come.
Oh my god.
I'm going to switch again.
So we try, it's kind of like doggy, but I'm just laying down.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
I want to be the doggy.
Oh my god.
I'm going to switch again.
So we try, it's kind of like doggy, but I'm just laying down.
Oh my god.
Oh my god.
Oh my god.
Don't stop.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Oh my god.
Don't stop.
Don't stop.
You just came inside me.
Uh, yeah, you told me not to stop.
Oh no.
What do we do now?
We have to push it out in the bathroom.
You're not going to…
How was that?
It was really good.
Thanks for watching!
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