Ready, Willing and Anal With John Hill

I don't think it's about, like, mouth, breakneck speed, face action. I think hand jobs are far underrated.

Look into his eyes.

They're the eyes of a man obsessed by sex.

Eyes that mock our sacred institutions.

Bedroom eyes, they called them in a bygone day.

You're listening to Sex with Emily. I'm Dr. Emily Morse, and I'm here to help you prioritize your pleasure and liberate the conversation around sex. Today I'm joined by John Hill. Love when John's on the show. He co-hosts Andy Cohen Live Mornings on Radio Andy on SiriusXM, and he's the host of The Fields on SiriusXM. We get into a bunch of stuff, fun topics on the show. We talk about tips for anal and oral play, plus tips for talking dirty with your partner. Via the Slutbot, one of my new favorite pastimes. And what do you do when slippage happens during sex? We also answer your calls and your questions. All right, Intentions with Emily. For each show, I want to set an intention for the show, and I encourage you to do the same. So when you're listening, what do you want to get out of listening to this episode? How could it help you? I find it helps me when I really set intention before I do anything. It could be, I just want to get better at oral sex. I think that's a great intention. Or maybe it's, I really want to try out anal play for the first time, and I want to know what to do. My intention is to give you a different perspective on anal and oral from a guy who really knows what he's doing. All right, enjoy the show. Hi, John.

I'm so happy to see you. I'm so happy. I wish I could be in the studio with you.

I know. So John Hill, just so you know, if you guys don't know, he's on Radio Andy. And he's on The Feels on Thursdays and co-hosts Radio Andy on Mondays and Wednesdays. Very popular show. You're popular.

And you're handsome too. Well, I hope we're popular. I hope people are listening.

I love it. They do.

We had a good show.

Everyone. Today, what'd you guys talk about?

Today on The Feels, it was my birthday show 'cause my birthday's tomorrow. So—

Happy birthday.

Thank you so much.

Didn't know. Okay, well, thank you. This is like your birthday eve. This is so good, okay?

My birthday eve.

That's right. And so, you know, I'm on the cusp. I'm a Scorpio-Libra cusp. I'm on the day it switches, so I'm technically a Scorpio. And so that was kind of the theme of the show. It was like a birthday show.

So let's talk about, I don't want to like redo a theme, but no, I am, when you tomorrow, so you wake up tomorrow, you're a new age?

43.

43, okay. So how are you feeling about the year that's gone by? And now your birthday. Any wishes for the new year?

Wishes for the new year? I feel really good and positive and hopeful for the new year. I feel very glad that we're done. Yeah, I feel for the first time— I'm not like, you know, I mean, for the reasons, of course, that are obvious, like fires and floods and politics and all that stuff and, you know, pandemics. But personally, I feel like I kind of— I look back and was like, wow, I mean, like, you've lived kind of path your life, sorta. So you gotta, you know, now, you know, and start enjoying it. You know, like, you know, I was, I've always been kind of a stressor and somebody who felt anxiety and stuff like that. So I was like, you know, you might as well just start enjoying your life.

Yeah, I felt that, I get it. So how do you think you're gonna do that though? 'Cause I've had those thoughts too, but how do you just like say, okay, I'm gonna stop stressing? I didn't know you were particularly anxious. I am too, usually we can sniff each other out.

Yeah, I avoid my anxiety and freakiness by isolating. So like, I— so working from home has been good. So I liked working from home. I've been, you know, I've been like, well, I can't, I can't, I have to stay at home at work. But oddly enough, do you know that now that I say that, I've realized I've connected with people more now that we've all had to isolate. Anyway, I feel like the next year, what I, you know, back to your question of how I put into practice saying, hey, I'm gonna be less anxious. I just take it step by step. Like, I won't avoid saying hello to the person who wants to like pet my dog. Usually I grab my dog and run. Like, don't bother me, don't talk to me. But it's like, all right, if they wanna pet my dog, they can, you know, I guess. But I don't feel like—

But it's true though, I get what you mean though. I'm the same. Like, part of me liked this quarantine stuff, but then But I'm avoidant too. You're so funny. So now you're like, I will let this person— I will count to 10 and let this person pet my dog.

Yes, exactly. I'll say hello to my neighbors. I won't like totally ignore them. And you know what? They're— I realize they're normal too. So that's like one little step.

Those are good steps. Yeah.

So I think mental health is going to be good. I feel good about 43. I don't really feel the number affects me at all. I'm not like, oh my God, I'm 43, I had hoped to accomplish dot, dot, dot by the time I'm 43. But I feel good about where I am and where I'm going.

I feel like you had a good year. I mean, well, COVID, so, but I feel like you found love. I'm gonna call it love. I mean, you started dating somebody at the beginning of this quarantine, right, Ramon? Yeah. And you met and then you don't live together, but you see each other almost every day, every night, or?

Yeah. Yeah, we basically lived together. Yeah, I mean, we, we immediately started isolating together, so we know what it's like to live together, and we, we did that really well. So that was a good barometer of like, oh, we could be boyfriends, you know.

I'm really happy for you. That's because what I kept hearing, and I wanted to kind of put this out there today too, because there's sort of a second wave cuffing season happening. Because the first, we had a pre— we had early cuffing season this year with COVID So, you know, cuffing season is when you sort of, you start attaching yourself to someone usually in the winter, starting in October, I think, September. Okay, here it is. During the fall and winter months, people who would normally rather be single or promiscuous find themselves along with the rest of the world cuffed or tied down by a serious relationship. But now what I kept hearing is that during COVID people were doing it. I'm not saying you did that, but you did get together early. You kind of did. We did, right? Studies came out that showed that breakups increased double. They were like 60% more than last year. But in this show, like, if so many people are breaking up and didn't get together and there's more people on the dating apps, I feel like a lot of our listeners are mostly calling in about like threesomes and swapping. And we could talk to Andrew, 34, in Tennessee. Listen, let me just— before Andrew talks, John, I gotta fill you in.

Yeah, tell me.

Andrew has had an interesting COVID. While some people here in California, whatever, we've been quarantined and it's been tough, Andrew's got himself in a sixome situation, not like, like 3 couples. And we've been following him on his journey navigating a sixome 'cause they're having a good time in Tennessee. Hi, Andrew. You're on with Emily and John Hill. Andrew, what, tell me everything. Hi, we think about you often. What's going on?

Things are going great.

Good.

I just had some random question. So through all of this, I have noticed that we're having intercourse a lot more than what we normally would, and I was just wondering, is there such thing as too much?

Too much sex? I think, yeah, all together or different times? Is it all 6 at once?

A lot of times, yes.

How often is it happening?

Yeah, we've managed to get to where we were once a week all getting together. Now we have maybe 1 or 2 days apart a week.

Are you all sleeping together at the same house every night, 5 nights a week?

Sometimes we spend the night, sometimes we don't. Sometimes we stay with different partners, like we swap around a little bit.

Okay, so here's my question for you, Andrew. Andrew's had some concern. Andrew's been through the wringer with this thing, but then he's landed and things are good, but now we're worried. Why do you think— what are the consequences? Like, this is Like when people like, oh, I think I masturbate too much, or, oh, I probably, you know, um, is it too much sex with my partner? It's when there's a consequence or there's a problem and you're like, oh, I can't actually get to work in the morning because my penis hurts, or I no longer want to have sex anymore with my wife because there's so many other people around. So you tell me, is there, is there, you know, how's your relationship?

Most importantly, everything's still good. I mean, I'm just wondering Like, is there a brick wall that we're about to fly up on?

Well, it may shift, you know, these things, they always shift. Even if, you know, a brick wall may seem like a brick wall, but it might just be— might just be how you look at it, you know what I mean? That's my take, is that sometimes things seem like impossible, but they might be opportunities in a way.

I mean, the other two couples, they're in their 40s. Okay, 40, 42. And I'm pretty sure we're starting to wear them out a little bit.

Are you guys just showing up? Are you making plans?

We're all making plans and just following through with it for now.

Andrew, why are you worried? Okay, so I have a question, Andrew, because let me tell you what I know about you. I know that you kind of worry about things because the first time that Andrew called— you mind, Andrew, I recap your thing here— that he called in and he was worried about his penis size because the other guy's penises, he thought they were too pleasing and yours was smaller than they would like. But the other two guys in the sixome happened to be listening that night, John. Didn't know that they listened. No idea. And then he got off the phone and they called him. They're like, buddy, you're fine. We love your penis. We love— everything's great. We're all having a good time. And then things have been great, right, Andrew? Like, then you've been going along and you've been— you said you felt more confident and you weren't worried about it. But now we have a new concern. Are you feeling like you don't want to as much, but your wife's like, let's go, I got the condoms, we're, you know, we're going?

You know what I'm saying? No, I'm, I'm ready to go. I think they're starting to slow down a little bit.

Maybe then if you're getting that sense, trust your intuition. And what I would say, Andrew, since you're part of such a, a wonderfully communicative sixome, we know this, why don't you put that out to the group and say, hey, I want to make sure we're not overstaying our welcome here. Should we take a pause? Maybe we reconvene over the holidays, you know, have a little sexy Christmas.

You always say communication is the best, so yeah, communication. What gives you the reason, though? Like, did something happen? You know, like, did— or are you just getting the sense that you're wearing them out?

That's it.

I'm just getting that sense that it's happening because, well, they were like a weekend thing, and now, now it's a lot, and we're still young enough to—

Yeah, well, Andrew, if it's too much, they're gonna tell you. But listen, I just think you gotta have a conversation with them. They'll tell you. Are you having sex with just you and your wife right now?

Yeah.

Okay.

Okay.

All right. As long as you're connecting intimately and things are getting along and you're getting along, I think I feel— I feel okay with this, Andrew. But I would recommend that since you get— you're worried about this stuff, I would have a real conversation with them and ask them. That's always the best way. The things that we think we can't say, when we say it, that's when we get the truth. Otherwise, we're delaying things, we're waiting till it's right. They're never going to happen. Right now, find out right now. Send a group text.

So true.

I'll probably wait till everyone's back on Monday and we'll just—

Okay, you don't have to do it tonight. You can do it Monday. You're good, Andrew. We're sending you lots of love. Take care of yourself, okay?

All right, thanks.

Bye, Andrew. Yeah, what do you think about that?

What I wonder is about COVID is about are people having sex? You know, I went to the doctor to get my physical a couple days ago and he was just like, nothing has changed. Nobody should be like letting their guard down. It's like masks all the time, even masks outside. Like, I don't know, like, I thought I was expecting him to be like, well, you can kind of chill a little bit, see some people for dinner or whatever. He was like, no. And so I'm— you know, one thing that I will say, and this might be controversial, but gay guys specifically, and I'll say this because I am one, I was talking to my friend Ryan the other day and I was like, are gay guys hooking up? Are they hooking up all the time? Are they having sex? Are they doing this on the Grindr and stuff like that? And, you know, my boyfriend and I are monogamous. So I was asking him, I was asking my friend, what do you think about this? And he's like, yeah, he's like, read between the lines and see what's not being said. You know, a lot of the gay guys in WeHo, you know, are saying, oh my God, I'm so mad I can't go get my haircut. I'm so mad I can't go get my tattoo. I'm so mad I can't do blah, blah, blah, blah. But what they're not complaining about is about fucking. And so it's, I mean, it leads you to, you know, maybe, you know, infer that possibly they're like, "What the hell?" And I know some people who are like, "What the hell?" They're like, "I can't, I'm not gonna like, you know, so if you're negative, I'm negative, let's do it." And it's just a risky thing.

It's really risky. You're so right. I love the way you read between the lines. You're absolutely right. And I don't know, I think it's the same thing.

I don't think anybody's saying like, "I'm so mad, I really miss hooking up." You know, no one's saying that.

Oh, right, because the people who really miss it went out and did it, and the other people— you're right, people are doing it. No, you're— and I think it's gay, straight, everywhere. I think if you're somebody who is gonna date anyway, or you're looking for, you know, you can't be alone, or dating online, I get it. And a lot of people— I'm hearing that from some people. I feel like it's split into two camps: the people who are like, I'm still wearing a mask, I'm still going out, and people are like, I'm, I'm gonna be careful, but I'm not giving up sex. Like, I won't get my tattoo, I won't get my hair done, but I'm going to Get fucked.

I know people who are like, I, you know, I'm negative, they're negative, we're okay. And I, to be honest, I've done that. I mean, not sexually, but I've done that with friends. It's like, well, I've seen a friend, it's like we both know we're, you know, both negative or have, you know, but we're in the mask, not officially okay.

It's not okay. It's really real. I mean, if you look at this middle states in America, like there's still COVID is happening, it's raging. So we just have to hang out a little bit longer.

We're talking about the middle, middle surge. But I just wonder about sexually, like, especially like a sixome, like Andrew who called in, like, what they discuss status, if they discuss—

do they?

Because I know, I think a lot of people don't care. I think they're like, well, I'm probably asymptomatic, like the most I'll get is like a little flu and then it's over. I'm willing to risk that to have sex. And I, and I don't not get that rationale. I don't think it's wise. But I think a lot of people say that. I think they're like, like our president just said, oh, it's not that big of a deal. I had it and it wasn't that bad. Forget it, take your mask off. So like—

'Cause of his medical care, what he got, but that is not realistic. People are getting it all the time, every day. That is not a great message to send.

You know, I wonder about like, you know, with a group like that, I wonder if that comes up. So I just wonder about the COVID of it all, but you know.

You guys, it's still happening. It's still going on. I'm here with John Hill. We'll be right back.

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Let's talk to Elizabeth, 21, in Vancouver. Hi, Emily.

How are you?

I'm good. How are you?

Good. Thank you. I'm just— I'll tell you everything. I'm just calling because I've been with my boyfriend for about 10 months. He's 26. I'm 21. And we kind of got this bump in the road where One night, all of a sudden, he just kind of got soft before he was about to put it in. And that was fine. We got over it. But then it's been happening continuously. So I'd say every other time we try to have sex, he will get soft before he puts it in. So of course, this brings out insecurities, and especially with a new relationship, you're like, this shouldn't be happening. So just some advice on how we can get over that.

Yeah, Elizabeth, this is such a good question and such a very common question. First off, you have to hear me and believe me, it is not you. He is attracted to you. He wants to be there with you. He has the erection and then he loses the erection. And the best way to help him deal with this is first off to let him off the hook. Like, I get it. Like, let's just keep going. Go down on me for a minute. What I found that works with men who experience that What exactly you're talking about? Like, he gets turned on at first, right? You're saying he's hard and then he's not. Okay. What you could do is just let him talk about it outside. Have you guys talked about it before outside the bedroom?

Not outside the bedroom. I know I didn't take your advice, but not outside the bedroom.

Okay, Elizabeth, this isn't outside the bedroom because he, believe me, he's so nervous to have sex with you every time because like, I better fucking get hard. This better happen. And you're like, it better happen. And it's like, literally, it's like the not erect elephant in the room. It's the same thing I always say when you're hanging out and say you could have an honest conversation. Be honest and say, I sometimes feel like it's me, but I have a feeling that's on it. And he'll be like, no, I don't know why either. And then you could come up with a plan because what he could do in those moments, what I've found that works for many men is that they just distract. They literally, he gets soft and then he goes down on you or you go back to making out. And once he takes his mind off of his erection, and then you get back into the moment, it comes back. So if he— because he's worried and you're worried, and so if you just kind of take the power out of it, because I'm sure he's worried. I mean, I'm telling you, this is not what happens when men— even especially men in their 20s— if he's not attracted to you, because that's what you're worried about, right? I'm not doing it right. He doesn't think I'm sexy. A 26-year-old man is not gonna be naked with you in the bedroom time and time again for 10 months if he is not attracted to you. It doesn't switch on a dime like that. It's not reality. And so mostly for men, this happens, it's really frustrating and they don't understand why. Now, there's a few reasons also. I want to tell you this, it's been interesting, Elizabeth. I got to tell you, in the last 5 to 8 years, I would say that I'm hearing from more and more men under the age of 40 who are experiencing exactly what you're saying. It used to be men over 40 because they lose testosterone and their penises just don't get as erect. Not all men, but some men. But there's this crazy phenomenon now and it's changed and there's a lot of different theories why. I think some of it could be anxiety. It happened once and there I go, I've built a new habit. It could be porn. It could just be that like he masturbates a lot for a partner and that I found that for some men they had this grip and they're used to, but this is mostly actually for men who can't cum. But that could be another thing that they masturbate so much that being with a human is actually like a bizarre experience because they're not used to it, or the grip on their penis is diff— it feels different than being with somebody. It could be they grew up in a religious household and they're afraid of, you know, somebody finding them, or that you're going to get pregnant because maybe you got a girlfriend pregnant once. I mean, there's a lot of different things. I don't know, a history of being an over— you know, he wants to always get an A and perform, and, you know, just anxiety that's pervasive in all areas of his life. It could be medications that he's on. I mean, these have always existed. But the thing that I'm seeing with younger men is interesting, and I don't have a conclusive reason. But what I'm telling you is I'm hearing it a lot more often. And so, and you like this guy, right? It's been 10 months.

Oh yeah, for sure. And our sex life is great. It's just, he has told me that it does give him anxiety and that he's freaking out and then I'm freaking out and then I get frustrated.

Yeah, of course.

So I think about it, it's just, it's always been in the bedroom.

Yes, let's take it outside the bedroom, have a glass of wine, go to dinner, do something and say, I know we haven't talked about this and this is really, I'm nervous. Be yourself, Elizabeth. Be the brave Elizabeth who just called into my show to talk to me about it and say, I know that we both have anxiety around this and I wanna talk about it when we're not actually in the bedroom and let's just talk about it. Has it happened before? What do you think it is? I've had concerns that you don't think I'm attractive, but I know that our, our sex life is awesome, so that can't be it. And just talk about a plan together. I mean, do you have pleasure? Does he go down on you? Do you have orgasms? No.

See, that's another thing is I just, I'm not a big— I don't like when men go down on me. And I don't know if it's maybe just I've had shitty experiences and just shitty head in my past days, but I'm never— again, I'm always thinking about him, him, him, especially with the situation. I'm never thinking about myself.

Okay, well, that— now we're getting to the good stuff here. Elizabeth, you— it is the hottest thing in the world as a woman who knows her body and what feels good. And let me tell you this, you have had shitty head. You're 21 years old. I'm telling you that all the head you've had till now, if they're with men your age, it hasn't been of a man who's more experienced at all. I mean, maybe someone at 21 could magically be great because he had a girlfriend for 3 years and they spent a lot of time on it, you know, he started having sex when he was younger. But the majority of it, this is a a skill that you develop over time. And so how, how about like your masturbation practice? What's that like?

Yeah, like that's, that's fine. And I've been more into like introducing toys, like trying to, um, but yeah, I mean, I have been with older men. I just, I think it's just one time I had shithead, and I just, every time I just think it's so awkward, and I'm like, oh, you know what, don't even bother. Even though, and I think there's other ways for me to orgasm, and maybe it's not head, I don't know. He wants to try though. He always does want to try, but I'm always like, no, no, no. But then I've also listened, like, yeah, like your flavored lube. I feel like that might help me feel more comfortable and confident.

Absolutely. In fact, I just, I have it all here. I just used it the other night with a partner. I was like, oh, I haven't used the crème brûlée in a while. And it's delicious. Like, I used it on him, he used it on me. It is delicious. And the mint chocolate. So try out flavored lube. But I'm also hearing that there's some insecurities about how you might taste or if your partner really wants to go down on you.

Yeah, exactly. And I think that's from like when I was younger and again, like not having proper head and being with men that were not men, right?

Boys. So yeah, this is such a great learning experience. So this is— and I would also just say that to him. I say, I thought, you know, you could also do some mutual masturbation where you are— he's masturbating and you're masturbating. So you're seeing how he touches himself and you're pleasing yourself and then you get to have an orgasm in front of him. You can bring your toy, you could show him what you like. And since you are so focused on his pleasure, he doesn't want that either. Because now he's worried about his erection and you're worried about his erection. Who's worrying about Elizabeth?

Yeah, let's worry about Elizabeth. No, that's a good point. Yeah, no, that's, that's a good point, actually. And maybe that would take away so much off of him.

Yeah, I think it will. I think absolutely. Why not find out if it's just anxiety, if he's just worried that he's like, oh shit, it's gonna happen again, Elizabeth's gonna leave me. So if you just say, you know what, no pressure, you get hard, you don't get hard, but I'm gonna get off, or I want to play with myself, or let me show you what I like, or in the past I've had bad head and let's go slow with it. Is it okay if I tell you what I like? Is it okay if you go really, really slow and we shower together first? Be honest with him because he doesn't— he's learning too. And I know he's 26 and that seems a lot, which it is a lot older than you, but that still might not mean he's had so many partners and he's incredible with oral. And the other thing is, you know what makes a guy really great at oral? It's about someone who pays attention, like someone who is willing to realize that every time he's with a new woman, it's a new vulva, it's a new— and he's willing to sort of pay attention to your body and what feels good and then, and that you're able to communicate with him. So let's figure out what this guy, what happens. Can you do it?

Yeah, yeah, no, and he has expressed that, so that maybe taking the attention off him, I think that would actually be very, very helpful.

Yeah, I think the reason why, so I mean, yes, absolutely. You'll be calling it out, it'll be something that, 'cause right now it's the thing that no one's saying and that makes it so much bigger and it's so much more painful when it's that elephant in the room that no one's talking about. And so if you address it, then you get to really be present with each other without both of you being in your head. And this way you can be in your bodies. And that's such a healthier way to live and how to have sex, especially. You're still learning too. Well, let me know how it goes, Elizabeth.

For sure.

Yeah, yeah. It might be—

I definitely will.

You might be nervous, but okay, good. Keep me posted. I'll be here. Good to hear from you. Thanks, Emily Morse.

Thanks, Elizabeth. Bye.

Have a good night. You too. Let's talk to Jamie, 29, in California. Hi, Jamie. Hi, Dr. Emily.

Hi, John.

How are you?

Hey, Jamie.

So excited to be on the phone with you all. Oh my God, love you, Dr. Emily. Loved your birth control episode last week. That was really, really great.

I'm so glad.

I have a question about— I love that episode. It was really helpful. I have a question about positions. I have a new partner, and he's really excited to do like doggy style and reverse cowgirl, and it just does not work for me. Not pleasure-wise, but like the actual anatomy and the physical part of it. It never works. It either gets like too weird or too sweaty, and it doesn't stick right. So I wanted to ask your advice.

Yeah.

Oh, really? No, these are, these are, it's a great question. So where do you want to start? Which one? Because they're different. You said doggy style. And what was the other one? Reverse cowgirl. Oh yeah. Okay, so doggy style, you don't have to be up on all fours, like bark, like you could be on your stomach, you know? You could be lying flat. People think it's so literally, you know, that you have to be on all fours, but you could lie flat. You could use pillows to elevate your thighs. You know what I'm saying? If you're on the, I'm assuming you're on the bottom. You could do it all. You know another great workaround? And maybe John can help me with this too, but on the edge of the bed, So you could be lying on the edge of the bed with your hands and then, then your partner could come behind. Would any of that work? Yeah, that's one of my favorite workarounds for doggy style. And also like the flat, you don't have to be totally flat, that part of it, but you could also elevate yourself even just like you could have your butt in the air, but you're, you're flat, you know what I'm saying? Your front, your arms are flat.

Right.

So is that helpful?

Yes.

What do you mean also? Oh, he slips out.

I'm like, why doesn't— Yeah.

He's got to get his legs closer to your torso. Like, he's got to get— Like, you know how, like, you have the knees inside or outside? You got to kind of sometimes split the difference. And other times he's got to, like, maybe get— He might just have to do it in a squat, which is— and kind of harder on the knees, but he might have to like— so that, you know what I mean? Like if he's squatting and his like— you just— can you get the picture? Like his knees aren't on the bed, his feet are on the bed, but— and he's in you and his knees are like up by your butt.

Yeah.

Oh, I see.

Okay.

Okay. So on the outside of me though, but then yes, exactly.

Yeah, so the knees are right. Yeah. And another thing that if he's slipping out is you could also put your legs together and, you know, if you are lying flat, that's, you know, you could—

same goes for you for reverse cowgirl though. Like, like if you, you're sitting on him with your knees on the bed and your legs on the bed, there's not a lot of places to go. So if you get up on your feet So, you're moving up and down on him? Do you know, can you picture that?

Mm.

So, like—

Like squatting, like knees deep down.

Yeah, you're squatting on him. You're squatting on him. You could also be leaning. You could also lay back on him and just pull yourself up and down, you know? Like you're sliding. I know explaining positions can be hard. I had this thing today. Yeah, so you're like, do you know what I'm saying? You're lying back. I'm like trying to do it here. You're lying back on him and then you're flat, right? You are, your back is flat to his chest. You're sliding back and forth. Yeah, and that way you could also be squeezing your legs together too and rubbing your clitoris. Here's the thing, remember, don't forget to stimulate yourself. Use a toy, right? Oh, you know what else you could use? There's something else that would be great. There's something called the doggy style strap, and it is from Sportsheets. I think we have it on our website. We can put it in the show notes at sexwithemily.com/shownotes. And it's cool. It's a positioning strap. So he can put it around your stomach and like kind of hold you and pull you into him more. So like you don't slip out any position.

Yeah.

You know, it's like he's steering her. So it goes around your stomach. Yeah. I think that's where it goes around your stomach or your thighs. You can play with it. Just thought about that little hack.

Very cool. Yeah.

Oh, wow.

Thank you all so much. That's really helpful. I'll have to try it out.

Of course. Let us know how it goes. Okay. You can call back. Yeah.

Thanks, Dr. Emily. Bye, guys.

Of course. Thanks, Jamie.

Good luck.

Yeah, you know what I'm realizing? I was on this show today. Do you know Call Her Daddy? It's a podcast.

No.

Yeah, her name's Alex, and she's a podcast, and it's a really popular podcast. She talks about sex. But today we are— I should circle back. You know, I want to ask you this because I don't know. First off, in the 15 years I've been doing this, when people ask me to describe positions, sometimes it's harder on the radio to be like, well, you can be very specific. Specific. Like, to me, just now thinking, like, lay back, your back is to his chest. It's just visually— I'm not— it's hard for me sometimes to explain it visually. But then I was doing it today. It was like a position episode. But I actually, I have to ask your advice about something about anal, about describing it, John.

Okay.

So we're talking mostly to heterosexual couples, right? She had a lot of questions from her listeners. And it was about the first time she uses her finger in her straight boyfriend's ass, just a finger. Okay, but let's say it's the first time you're with somebody, and I just explaining the positioning when you're giving a blowjob. I was trying to explain the best way to put your finger in someone's anus after you've consented that they're into that. And I was trying to explain it, and I was like, usually I don't stumble, but I couldn't. I was like, well, if you're giving a blowjob and you're lying on your back, and then make, you know, you could On your back giving a blowjob? Oh, he's on his back and I'm giving him a blow— I'm between his legs.

Oh, all right. And he has a dick and he's on his back.

Yes, he has a dick.

Okay, he's on his back and he has a dick.

And we've never— and it's the first time he's had a— she's like, what's the best position if you've never had a finger before? You've never done any anal play, or maybe it's even a butt plug, but let's for this purpose, say it's a finger, and I was trying to explain how he lifts up and then you could just kind of put your finger inside, but we got very technical. I don't know how to explain why it was so very technical. I don't think you have to.

I think the main thing is go with the flow. I think you have to be in the legs, and I think middle finger— don't worry about which finger it is, always go with the middle because you can control more. You can't control anything with like a ring finger or pinky or a thumb.

True.

Maybe a forefinger, but always—

maybe a forefinger, but the middle finger—

yep, middle stabilizes it as well. But also it's mostly about— and it doesn't have to go in very far, that's the most important part. And so suck it. When you're sucking it and you— and it's super wet, then your finger's wet, then when it— then you just kind of like go around, and then it just kind of goes in a little bit. And I think it can just go in a tiny bit, and it's like you motion 'Come here, come hither.' You mentioned the 'come hither,' but you don't go in.

She was like, 'Well, do you go in and out?' Like, no, no, no, no. So you don't go in and out, and you stay inside, and you just kind of rub like a 'come hither, come hither, come hither.' And you can even just leave your finger there too. You don't have to move it that much. Leave it. It's like a butt plug. Your finger becomes a butt plug.

And as long as you keep sucking it, nothing else matters about the ass because it's just going to help it out. But just leave it in there a little bit. Don't stick it in far, that's gonna remind him of the doctor.

Exactly.

As long as the dick is being sucked, it doesn't really matter. Just keep going.

And like, what if the guy was squeamish about anal play? So you don't want to go too aggressively either. What'd you say? Suck harder. If you're sucking their dick hard enough, they won't care what you're doing.

No, I really care. Yeah, just like stick and like then say like, you know, I'm gonna, I'm gonna put my finger in your ass a little bit and then just keep giving like the greatest blowjob ever. And then you're good to go.

Can you tell me real quickly too, John, is there a certain go-to blowjob sex move that you have? What is the best blowjob ever? And is it different for everybody?

It's different for everybody, but I think hand is very important. Hand. I don't think it's about like mouth, breakneck speed face action. I think there's nothing there. I think hand jobs are far underrated, highly underrated. So I think a hand job with like a little, you know, on the tip is nice, but like, jack it off, jack it off, and like suck the tip, lick the tip with your fingers up his ass.

When your finger's up the stick, good. Yeah, you're busy. There's a lot going on. Like, hopefully you can multitask, you know, like walking, chew gum, suck a dick. Like, there's a lot to figure out.

Give your jaw a break and just like, you know, stroke it, lick it, you know, just like—

doesn't have to be breakneck speed. You don't have to choke yourself. You have to do that.

Yeah, unless you— unless that does something for him emotionally and makes him feel like, oh, my dick is so big it's choking you, then like pretend to do that, which like we've all done.

And then, you know, right, we've all done that. But I don't think it's— what we're saying is it's not necessary because the tip and the frenulum are the most sensitive parts. So if you're— your mouth's on the tip and you're licking around, it's good.

I mean, I think shaft is quite important as well.

With your hands though, we could take it off the hands. You don't have to have like—

exactly.

This is a good chat. More dating and relationship advice after this break. Thank you for supporting our sponsors. We love them. I hope you do too. So during the break, there's something called Juicebox It. It's juiceboxit.com.

Oh, that's it.

That's it. So about a year ago, I signed up for it, and there's something called Slutbot. And every Thursday I get a text from the Slutbot asking me if I want to play, do I want something dirty, do I want something spicy. But when you start with Slutbot, back up, you say, I'm a woman, I'm interested in men, I'm a male, I'm interested in men. You can do any gender, anything you're interested in. And then you just answer a question and then it, you know, it's trying to get me to a hotel room right now with a, you know, a butt plug and a necktie. And it's telling me what to do when I get there. And so you could also do this with a partner. It gives you inspiration. Like sometimes I'll just look down and it'll say, hey babe, I'd like to take some time to focus on you. How does that sound? And then you answer it. But these, I actually gotta be honest, I ignored the slut bot the last few weeks 'cause I was just really busy. But today I said yes.

And now—

You did a thing with the slut bot?

Yeah, I did. Just like all the advice I tell everybody here, you can't be a passive dater if you actually want a relationship. And I'm the kind of person, I have to go all in. I have to be like, I can't casually go on an app and then swipe and then I match with 3 people and then I don't go back to it. It's like, and then talk about not dating, especially right now. I'm not meeting people in the SiriusXM elevators or whatever. That's not happening anymore. We're not out. And so if I actually want that, I know what it takes for someone like me. Like, it will be an effort. I'll have to have my assistant be on my schedule saying like, right now you're gonna swipe for an hour and you're gonna mess. If that happens, or just follow up with people that I actually like that I haven't had time for. Or, you know, respond to Slutbot, things like that. I didn't have time for Slutbot. You know that I don't have time for, for dating right now. But January 1st, it's on, which will be a good time. Okay, let's talk to Rick in New Hampshire. Speaking of dating apps, Rick wants to know about the dating apps. We're here to help. Hey Rick, what's going on? How can we help you?

Well, over the weekend I joined the Filipino dating site because I think Asian women are beautiful. And I get a lot of quick responses, and a lot of them are actually already located in the United States, which is fine. But what I'm finding out is these people that I'm meeting, they don't mind going on to Google Hangouts, which they all want to go on there that way because it's easy to chat and everything. But once you start talking to them, they start wanting to know your income level, and then once you start getting further, they start telling you that they love you, they want to move in with you, 'Can I come with you, be with you?' It's like, I'm 57, and it's like, I haven't been on a dating site in a long time. Is this a new norm for dating sites?

No, Rick, I'm so glad you called into Sex with Emily because it's not. It depends, I think, on the dating apps that you go to, and they're all different. Here's the thing, there's a dating app, there's a farmer's dating app, there's a dating app for people who have STDs, there's a dating app for people who like to surf. There's dating apps for everything. So I'm curious what dating app you're on.

Filipino Date.

Okay, because you like Filipino women. So I could see why that would be— it feels like a shortcut. But if that's your experience, that it sounds like it's one of those apps that's arranged for women to find a husband.

And I just say, I just want to plug TLC's show 90 Day Fiancé. And this happens Every single episode. This— and it's all websites where, you know, the women are like, I love you. And they start a relationship immediately online and they kind of— and vice versa, men as well. But it's exactly what you just described. And that's how it kind of starts. And sometimes there's real love involved. And but a lot of times it's about a green card.

Yeah, it's about a green card.

Well, the ones I'm talking to now, one's in New Jersey. And one's in Illinois and one in the States. The thing that throws me worry is when the one in Arizona, she's already basically kind of hit me up for money.

No, no, I say no.

No.

Yeah, it might be a scam. No. Can you— what about finding someone local in New Hampshire or nearby or meet them first?

If you like them, give them all your money. Fine. But like, not before you meet them.

Well, the thing is, like, on Google Hangouts you can do like little videos. So I sent out a field to everyone to send me a little video, try to match it up with the picture that they actually have posted online. And 2 out of 3 have, and they've actually— the exact person. So those are the 2 I'm basically chatting with now.

But, but what about like something like Bumble or Tinder or Hinge. There's a lot of other mainstream apps.

Yeah, you could say your preference is Filipino, or you can say that is, you know, preference.

I think this app is set up for primarily the women that are— you're going to find on this app. I don't think it's that they're going to be catfishing. They're not going to be lying to you who they are. I think it's more about their agenda for joining this Filipino dating app is, is to find— is likely to find a husband. To pay for that, or partner. Yeah, that's gonna be— that's what they're gonna lead with. So if you're really looking for a mutually beneficial relationship or somebody who isn't looking for money, you might want to try Tinder.

Alrighty. Yeah, so give it a shot.

Okay, good, Rick. I would be careful. It doesn't sound like it's jiving with you, you know. Just, uh, go slow.

All right, I appreciate it.

Okay, okay, thanks, Rick. I appreciate it. Thanks for calling. Good luck. Good luck.

Meet the person. Don't give any of your money away. None of it. Everyone's out of a job. People are trying to take other people's money.

Thank you. Thank you for saying that. I just— I haven't had this— I couldn't tell if he— you don't know. Like, 90 Day Fiancé, I saw one season. I'm trying to watch more TV. It's like sometimes it works, but it's, it's not— it's typically not good, right? Can we say that? Not good.

Great television, but no—

great television, but it's not— you're just yelling at the TV the whole time going— and the problem is, and Rick sounds like he might have just stumbled into the wrong place. That's what I was trying to understand, right?

He sounds like a great person, by the way. A lot of the people on 90 Day Fiancé are great people. The point of it is—

what happens? Tell me. You love it. Tell me. You've seen it.

People want to connect. People want to be married. People don't want to be alone, and they're willing to bend all sorts of logic. Like, well, I saw them on Google Hangout and they look pretty cool and nice. Like, that's not enough. And I'm cool if people want to say I'm an asshole, but like, meet the person, give nobody any money. Like, don't trust anybody. And like, I'm so sorry to say that, but like, don't.

No, you are not being— this is very helpful information. You should definitely meet somebody in person. Here's the other thing that's been happening is that during COVID I feel like there's a lot of people I've been overhearing conversations, I've had friends call me like, I'm in love, and they tell me, like, wait, back up, you haven't met yet? They're like, no, but we talk every night. I'm like, you gotta meet in person. But then these sites, it just takes another step further. You're right, meet the person. What's the rush?

Better be alone than have all your money taken.

Exactly. Unless you're into that sort of thing.

Oh my God, that's another show.

Oh, financial— what's it called? Financial domination.

Yes. Oh my God, it's so sad.

That's a whole trend right now too. FinDom. Financial domination. Yep, that's it. Oh my God, this is so fun, John. I love seeing you, John Hill. Everyone check out John Hill and Andy Cohen Live and his Show of the Feels Thursdays. You can also follow him on Instagram @johnarthurhill. All right, that's it for today's episode. I'll see you on Tuesday. And thanks for listening to Sex with Emily. Be sure to like, subscribe, give us a review. You know, reviews help us. And also, if this show helped you in any way, you learned something, right now just send it to a partner, a friend, a lover. We all need to learn, right? We're all in this together. You can also find me on Instagram, Facebook, and Twitter @sexwithemily. Oh, and sign up for my newsletter. People tell me I give really really good newsletter. Sign up at sexwithemily.com. And while you're there, we've got so many great blogs. If you'd like to talk to me about your sex life, dating, relationships, just message me on Instagram or call into my SiriusXM show Monday through Friday, 5 to 7 PM Pacific. You can call me there, 888-947-8277. Get a free 30-day trial at sexwithemily.com. Www.sxem.com. Was it good for you? Email me feedback@sexwithemily.com.

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