It's All About Trust

Transcript

Hey, darling, what's up? You sounded a little freaked out in your texts. You okay? Oh, okay.

You had me worried. I thought there was like an emergency or something. What's going on? Oh, oh, I'm sorry.

You were with her how long? Oh. Okay.

Well, I know it's not a long time, but breakups still suck. Can I help? Um.

Okay. All right. Let's talk about that.

What did she say when you broke up? Adventurous. What does that mean? Adventurous.

Like bungee jumping or something? Because I'm not going to lie, that sounds terrifying. So I'm on your side if that's what she meant.

Well, that's fair. I'm always on your side, but. Oh.

Well, that's a little different, isn't it? Uh, okay. First of all, do people actually say that to other people now? That they're not sexually adventurous enough? Maybe I'm just sleeping with the wrong people.

I don't know. Okay. Well, what does that even mean? Yeah.

I mean, you're allowed to have boundaries. You're allowed to have limits. That's okay.

And if it's not, the person you're with needs to, you know, examine themselves. Not make you feel bad. So was that what was going on? Because if so, she needs her butt kicked.

Babe, it's okay. I know this stuff is hard to talk about. And you don't have to if you don't want to.

Fair. You did bring it up. All right.

I'm listening. That kind of adventurous. Okay.

Well, that's a little bit different, isn't it? And did she bring this subject up prior to said activity? Or did she just mention it in the moment? In the moment, of course.

Yeah, that's kind of the worst time to bring up something new, especially something like that. I'm sorry. I'm so sorry that that happened.

That's not cool at all. I mean, I hate to say, but I kind of feel like you dodged a bullet a little bit. Yeah.

Because if somebody is going to bring that up in the moment and then get mad at you for not just going with it, that's a red flag, isn't it? Yeah. So, okay.

I mean, it still sucks, but at least you're not having to deal with that. So what can I do to help? Do you want me to go kick her ass? Not really my style, but I can make it work.

At least I got you to chuckle. Okay. All right.

All right. I'm listening. Well, that's fair.

I mean, wanting to be more adventurous is not a bad thing. So if she had talked to you about it beforehand, would you have been open to it? Maybe.

Okay. All right. Was it just because it was sprung on you in the moment or was it the person? Like, what was the issue then that makes you think it won't be an issue now? Okay.

I'll give you that. Trust is a big part of that. Yeah.

Well, thank you for that. The friends with benefits thing has been lovely, but the friendship itself has been going on a lot longer than that. I'm glad.

I'm glad that you trust me. Is that what you want help with? Do you want to go there with me? You do? Hmm.

Yeah. Yeah. I've done it before.

Giving and receiving. But, babe, anal sex isn't something you just jump into, especially. ..

How do I say this? Especially on the heels of an experience like that. I mean, I have no problem helping you with that, but I want to know if you're going to do something like that, that you are wanting to do it for you, not just to prove some stupid ex-girlfriend wrong, you know?

Because it's a big deal. You had? Really? You'd been thinking about it for how long? Oh.

Well, that's a little different. Okay. So it really was the person and the approach then that made that not a good situation.

Then you're really better off without. Okay. If that's what you want, I have no problem doing that with you.

Now? Sure. I don't have anywhere to be.

Are you sure you want to do this? If you have to do it right now before you lose your nerve, are you sure this is something you want to do? What is that? Oh, you're prepared.

Yeah. Okay. That's a set of toys.

And a very large bottle of lube. You've been thinking about this. Okay.

Yeah, I mean, sure. I'm a little worried this is going to feel really clinical right now, though, because of the lead up to this. Yeah.

So tell me what you actually want. Mm-hmm. You want me to penetrate your ass with that? Okay.

All right. That'll be the goal. What do I mean? Okay.

Anal sex isn't something you just do, because it can be really uncomfortable. Yeah, it takes a little bit of working up to. I mean, sometimes it's fine, but I wouldn't go in with the ultimate goal today being that.

It's a good size. It's not huge. It's a nice starter size.

Assuming you went to a store. Yeah. Did the salesperson help you with that? Good.

Good. I'm glad you did that instead of just going online and picking something, because talking to somebody who knows what they're talking about is always preferable. Yeah.

Okay. Yeah. Okay.

Yeah. But it's not just going to be lay down, spread your legs, and let's see what we can get in there. That's wrong.

Sorry. This is why it's better to do this with friends, because you can laugh. Let's just, I don't know, fool around the way we normally do and work it in when it feels right, okay?

I just don't want you going in with these big expectations and being nervous about it, because that's going to make it worse. Okay? Okay.

So breathe. Breathe. Relax.

We're all tied up in knots, so just chill. Chill. I got you.

I got this. We got this. Yeah.

Yeah. We're good. I've been horny anyway.

Yeah. It's been a bit since. ..

What's her name? What was the last one I was with? I don't know.

She gave lousy heads, so I didn't bother remembering. Did you just laugh at me? What? What? It's true, though.

Well, when you're hooking up with somebody just to hook up with them and the sex is bad, they don't really hang around, you know? Okay. Come here.

You look like you're just ready to burst here and not in a fun way, so get over here. Come here. Relax.

We're just going to play. I think that pussy of yours needs some real attention first. Don't you? Yeah.

Take your clothes off. Come on, off. I'll take mine, too.

Very nice. What? I always smile when you get naked.

I like it. Yeah. Well, okay, so I don't know if you get how this whole friends with benefits thing works, but we're friends because we laugh and we have a great time and we get each other and all that good stuff, but the benefits part is because I think you're really fucking sexy, and I love playing with your body and touching you and all that good stuff, so when your clothes come off, it's a really good thing.

Okay? Well, I'm glad you feel the same about me. Okay, good.

Let me get my hands on these tits. I also love how you look embarrassed when I say the word tits. It's fun.

Oh, your hand's on mine, too. We're going to stand here and feel each other out. Okay, yeah, I'm good with that.

Just keep doing what you're doing, and I'll keep doing the same to you. Fingers on nipples are underrated. Yeah, they are.

You like that? Just gently pull. I like it, too.

Mm, mm, mm. Oh, yes. Mm.

Why don't you sit on the couch? Yeah. Mm-hmm.

You might want to put that blanket down first, though. It's going to get messy. Okay.

I'll get down here. And all I want you to do is just spread your legs, lay back, and relax. Mm-hmm.

Mm. Oh, this pussy. Mm.

You're wet already. Just talking about this has been a turn-on, hasn't it? Yeah.

I'm going to grab the lube here. Perfect. And I'm going to just rub some on your ass, just a little bit, with my fingertip.

Just to relax you, okay? While my other hand pays attention to this perfect pussy. Mm.

My thumb on your clit, you like that? Yeah? Fingertip strokes your asshole.

Mm-hmm. Spread your legs wider, baby, come on. Give me full access here.

You know what? Spread them, bend your knees, and put your feet up on the couch. There we go.

Ooh, perfect. Ah, everything spread wide open for me. Mm.

Little kisses on the insides of your thighs while I rub. Mm. Mm.

Over the top of your pussy. Feel my breath. Nice and warm.

Mm. Just lightly stroking your ass. Mm.

Your clit looks like it's happy to see me. Yeah? How happy? Think I can make you come like this? Yeah? Why don't you play with those pretty nipples for me while I do this? Let's get you going as much as we can.

Mm. Little more lube. Mm.

Okay. I'm just gonna push my fingertip into your ass now, okay? I'm gonna go a little faster on your clit.

There you go. Good. Just the tip.

Relax. Feel my finger just push in. Good.

Oh, do you like that? Yeah? Keep pinching those nipples for me.

Mm. Just a light stroke on your clit. Nice and fast.

Yeah. Ooh, yes. That's my girl.

Good. Good, good. Oh.

Just the fingertip, only to the first knuckle in your ass. How's it feel? Good? It doesn't hurt? Good.

That's what we want. Mm. Let's see if I can make this clit explode.

Mm, that's right. Um. Mm.

Oh, good. Yeah, move your hips if you want. Do whatever feels best for you.

That's right. Good. I'm gonna push my finger in just a tiny bit more.

Oh, there. Mm. Mm.

Okay. Oh, keep going. Oh, yes.

Yeah. Rubbing that clit. Come on.

Come on. Oh, good. Oh.

You keep squeezing my finger. Mm. I'm gonna pull out a little bit and push back in, just light little thrusts.

That a girl. Good. Out and in.

Out and in. Very slowly. Good girl.

Mm. Mm. Oh, yeah.

That's right. Just a little bit. There's lots of lube, so we're good.

Yeah. Oh, good. That's right.

Move those hips. Come on. Mm, you can do better than that with those nipples, I think.

Yeah. Oh, this wide open pussy. Oh, won't they lean forward and just.

Ah. Delicious. You like my tongue in your pussy? Mm.

Mm. Mm. Ah.

You're about to cum, aren't you? Mm. We're gonna stop now.

Mm-hmm. Because we have other things to do. And if you come to.