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The Dating Coach

So...

Did my little brother get laid last night?

Uh, no

It didn't go that great

Why not?

Like, it just...

Yeah, it didn't really go very good

OK, but like, why? Elaborate

Like, what?

Yeah, I just feel kind of stupid, I know

Like so...

You know, like we were hanging out and then...

and then she like I asked if she wanted to go back to...

you know, to her house and she said like, yeah

Cause I said like we could like watch Netflix

And...

hang out

and we were on her couch

And like...

it seemed like it was going really good

- And? - And then...

well, like I started like making out with her

- and like, cause... - Yeah?

she was like looking at me, like you know, so where she was looking...

like at me for a while and stuff

And then she seemed like kind of like that

And then, um

Yeah?

And then...

Like... um...

I...

That was good, and then like... I... um...

I like grabbed her boobs, and...

but like really hard, kind of...

- ...and squeezed them - Oh

- Cause I thought that, you know, I thought... - What?

I thought, cause you said like a lot of girls like that kind of rough stuff, you know?

I mean, yeah, but... like...

That depends on how rough you're going there, buddy, like...

Yeah, I squeezed them kind of hard, and then I called her...

Like, I grabbed her hand and put it on like...

on my crotch, and I...

to... like... um...

Oh, Man

I said like, suck my dick, slut

- I know that's too much, right? - Oh, my God

- Yeah, a lot - She screamed at me and she made me...

She made me leave and...

Um... I think she blocked my number

I mean, yeah, I don't blame her

You gotta learn how to set a mood, dude

I know I just messed up, I just thought, you know, cause you said like to...

- It's good to be like dominant, you know? - It is good to be...

dominant and assertive but like...

not in a degrading way

Especially if it's your first time with another girl you have to kind of...

coax her into it, you have to make her feel good first, and...

Grabbing her boobs and then telling her to suck your dick, slut...

Isn't gonna cut it

Yeah, I kind of realized I was...

afterwards I was dumb

Yeah, I mean, at least...

you know, how hard did you even grab her boobs? like...

It's kind of hard to mess that up

Like pretty hard

OK, well

You gotta... like, it's good to be like firm

But Like...

Don't just like squeeze, ever being hard, but you gotta...

You gotta be gentle, man

Oh, OK

I mean, you can get a little rougher as it goes on, but you have to...

read those cues from her, like...

she is getting excited from it or nipples getting hard

OK, yeah, I didn't do that, I just went like right into it

Yeah, no, you have to read body language first

Hmm... you get it?

I mean, I think so

Yeah?

OK, come on, show me

How would you grab someone's boobs?

Do you like...

- ...on your boobs? - Yeah

Are you sure?

Who, do you see another pair of boobs around here?

Yeah, but isn't that, are you sure it's okay?

Yeah, I'm fine, come on

This is for your...

benefit

I mean...

- Is that too hard so? - It's not too hard, that's fine, but it's just

- Can I give... - Cause I squeezed her boobs like really...

like that, and then I, like, grabbed her nipples

I mean, they like that, but you have to be...

- Is that better? Like, that's not that hard, right? - No, that's better

So that's...

I mean

Yeah, you can go a little harder than that, though

OK

Cause now you just kinda seem timid

- I want you to be, like, firm - OK

But...

- And both of them are good, right? - Yeah

You gotta alternate, can't just give all your love to one

You're already getting better, I don't know how you fucked that up

But...

I mean, I just kinda went like, you know, like...

really, like a gorilla fist

Oh, my God

No, you gotta make her feel good

Cause I know you wanna have fun...

but you gotta let her have some fun, too

OK

Oh

- So, like... - Uh-huh?

I should've just like...

maybe, like, rubbed them more...

- ...like, with her shirt on - Yeah

Right? and then, like, some, and then...

if I could, like, feel, like her nipples start getting hard and she like...

Yeah, it's a good indication that she's liking it

freak out, then, like, I'd probably, like

You know, I take underneath her shirt, kind of...

- Yeah - Right?

And then, like...

I just like, I must say, I shouldn't just be like, suck my dick

No, no

Definitely not, like...

I don't even...

That's really fast, like, were you even hard...

- ...during that? - No, not yet

So, you wanted her to...

put your soft dick...

in her mouth?

- I mean... - What was the thought process there?

I don't... yeah, I don't know

There was none, that's the problem

You have to, like...

figure out how to transition it

Like, get her nice and hot and steamy

So like we could make out and...

- Yeah - ...touch her boobs and then, like...

like, I touch like her...

- Uh-huh - ...down there some

Yeah

I mean, that's kind of the point, you gotta get her excited and make her want...

- ...to do stuff with you - OK

- That makes sense - Yeah

Yeah, you can't just, like, demand it from her, this isn't a porno

Yeah, I guess that's true

Alright, so...

If you did have to...

like, transition it, how would you go about doing it?

- If you want - So probably like...

You know, in the boobs, and she's like into that...

- Yeah - ...and then I'd probably like...

Maybe...

start touching like down there...

or some?

Yeah, but I'd say...

play around with it like, maybe, rub up on her thigh

Like, tease her

- You can't just, like, go straight to... - OK

pussy and boobs, like...

OK

Girls have more than just those two things

And then, like...

- ...I can back - Yeah

See, you're already doing better, you gotta just tease her

What about like the face and stuff? Should I like...

- ...touch like - Sure

- Yeah? - Yeah

Cause I thought about, like...

choking her, but that's just doing sex, right?

I mean, you have to feel it out with her, I would say start by just, like...

kind of playing along with it, apply some pressure, see how she reacts to it

OK

So, like, just kinda, like...

- ...soft, kinda? - Uh-hum

- Is that, is that OK? - Yeah, that's better

Thanks for helping me with this stuff

Like, you didn't have to do this

You're, like, a really good sister

Yeah, I know

But...

I don't know, I don't want you to be a virgin forever

Oh, you're kinda starting to play with yourself now, too

- Sorry - See, like that, no, it's okay

It's that point, see, you're excited...

she's excited, now you can actually...

kind of move it along a little bit more

Oh, yeah, that makes a lot more sense

Yeah

Cause you're both kind of just...

feeling it, you're vibing

Yeah

You're both getting excited

And then, like...

I would kinda...

just, like, just try to maybe take her shorts off

If she's into it

Yeah, but, you know one great thing that girls really like?

Is direct questions, like...

Hey, do you want me to take something off?

So, I'd be like...

- Do you want me to take your shorts off? - Yeah

And then...

And if she says yes...

you do

I guess you probably shouldn't actually take your shorts off, though, right?

I mean...

I'm trying to help you out here, bud

- OK, yeah - Yeah?

- And like, just kind of help her some? - Uh-huh

Wow

- It's really good - Yeah, I mean...

you could have gotten there

You just have to feel it out, right?

like, touching it some, right?

That's nice, I like that you're not going straight for it

Yeah, I thought about it, but I knew you'd probably say that was too much, too fast

Uh-huh, you have to kind of feel it out first

- That's good, right? - Yeah, that's good

- You're missing a vital thing, though, kid - What?

The clit

Oh, yeah

That's like... nature's fun button

And then, like, I can, like, go...

- like, lick it and stuff, right? - Uh-huh, yeah

You're getting really hard, though

Yeah

See, now she's excited, a little bit wet

Yeah

- And you're getting excited - Yeah

Now would be a good time for a blowjob

But you have to ask her

You don't just tell me like, give me a blowjob slut

Ask her

I just, like...

- Do you want to blow me? - Yeah

- And then, like... - Uh-huh

just like take off

Exactly

See, you're already doing better

OK

Are you sure this is OK?

You don't have to do that?

No, this is for your education

OK

Oh, thanks

Oh, feels good

I know what it is

Cause unlike you, I actually have some experience with it

Yeah, you can touch my hair, that's fine

Oh, feels so good

Thanks for helping me out

I unknew you'd be so thick

Thanks you

No problem

- Can I take these off? - Yeah, they're just getting in the way

- Oh, That feels really good - Yeah

- That's good, right? - Yeah, that's good

I like that, that's a good move, use it

OK

Oh, my God

Oh, wow

Yeah, she might not do this but I will

That feels kinda good

Oh, fuck

That's much better

But you're being a little bit passive

OK

So...

should I...

tell her, like, let's fuck?

I mean, do you feel like you're ready?

Yeah

Then, I think it'd be a good time to transition

So, is it like, I wanna put it inside you?

Yeah, you can ask her that

Or, do you want me to put it inside you?

I want you to put it inside

I wanna fuck you

It's OK?

Yeah, it's OK

Fuck

Oh, That feels really good

Oh, my God

Oh, my God

- That feels really good - Yeah

It feels good for me, too

Oh, my God

- Can I grab your boobs? it's OK? - Yeah, you can do that

- Oh, my God - Oh, yeah

I shouldn't cumming, right?

- No, no, it's too early - OK

- I'll put it back inside, right? - Yeah

- Please - OK

There you go, you gotta...

learn how to use your cock

Yeah

Oh, fuck

That feels good

Yeah

- I'm gonna get on top of you - Yeah

There you go

- Oh, yeah, go harder - That's good?

Yes, that's good

Oh, there you go

Oh, yeah

Oh, fuck

Yes

Yes

Keep going hard

Oh, fuck

Oh, yeah

Yeah

- I wanna take these off - Yeah

- Oh, fuck - Yeah, your feet are sexy

Feet can be sexy

I think...

Sorry, I thought I was gonna cum

It's okay

If you were fucking that girl, where would you wanna cum?

I'll like in her mouth

You can cum in her mouth

I mean, some girls don't like it, but...

you have to ask

So like, I'd say like..

like...

I wanna cum in your mouth?

Yeah

And if she would say like yeah?

She'll say yes or no...

depending

Oh, God

- Make sure you make her feel good first - OK

Fuck her harder, yes

Yes

Yes, keep going

Don't stop, don't stop

Fuck, yes

Oh, my God

Oh, that was good

I mean, you made her feel good

- I wanna cum in your mouth now - You can cum in my mouth

How was it?

That was...

like amazing

See what happens when you do it the right way?

I feel like I like

I know like exactly what to do now

Good, just...

pay attention to her body language

Ask for...

things that you want, don't demand them

And make her feel good

And she'll make you feel good in return

You're so smart