
⚠️ Sensitive Content Warning This episode contains explicit sexual discussion. Listener discretion advised.This week features two anonymous “Phone a Friend” submissions — and Donald and Autumn don’t hold back.The first listener writes in about trying...
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You know what they say. Early bird gets the ultimate vacation home. Book early and save over $120 with VRBO, because early gets you closer to the action, whether it's waves lapping at the shore or snoozing in a hammock that overlooks. Well, whatever you want it to. So you can all enjoy the payoff come summer with Vrbo's early booking deals. Rise and shine. Average savings, $141. Select homes only. I have one girlfriend. This is funny. We've been friends for like 15 years, since Dom was like 2. She used to train with me. And so I remember one day we came in, I don't know, I told her squats or something, and she was like. She gave me this look. I was like, what? And she goes on this whole story about how she was with her boyfriend the night before and da, da. And they're doing things. And then all of a sudden he was like. Then he said, don't move. She was like, what? And then he, like, tried, and I was like, wait a minute.
B
Oh, my God.
A
Like, no preparation, no wording. And she was like, yeah. And I'm like, that is your first time to move.
B
Run.
A
Get the hell out of there.
B
Don't move.
A
Why?
B
Hey, boo. Hi. You ready for some titillating conversation today?
A
Titillating? It is. I am. I mean, we said, give us your juicy phone of friends and they said,
B
this one makes me blush a little bit. But we're. We don't. We don't make it. We just read them.
A
I'm just here for it. We're gonna help people out today, though.
B
Yeah. So we decided that it would be fun to start with the phone a friend and just see where this conversation takes us.
A
Also not suitable for work, not suitable for children.
B
Definitely if you're in the presence of. Of anyone that if you blush over
A
anything that has to do with sex, you need to.
B
One of our other episodes, put some
A
headphones in and come back to this one.
B
Speaking of. Never mind.
A
You know, say it. Make the joke.
B
I was gonna say, speaking of. Come. I'm sorry. Low hanging fruit. Oh, my God. Oh, okay.
A
I'm not gonna eat these chickpeas while we're talking.
B
Long email, but it's worth the read.
A
It's so worth the read. Do it.
B
I wonder if you guys opened a can of worms with this advice segment. Here's my question, and I doubt I'll get picked, but I really want to know because maybe this is a Donald question. Well, she doesn't know you Very well. Yet
A
not wrong.
B
You mentioned a woman who was trying to get pregnant doing anal. The stupid. The stupidity scares me. My question is a little more relevant but just as embarrassing. My husband and I talked about trying anal, but we're both hesitant. Probably more that I was hesitant than him. So we finally tried it one time. Scene was set. We're in the mood for something new. Well, let's just say it was painful, messy and oh my God, off. I do know how ex. I don't. I didn't know how extensively I needed to be, quote, empty. So I literally the bed when we finally gave up and he pulled it out. Tmi. Christ, that was embarrassing. Maybe not suitable for a podcast. Well, it is for our podcast.
A
We love you guys by the way. We are here for this. This is full on conversation we would have and are about to have.
B
It was just so painful. What's the big deal about this? Why is it even a thing? Who enjoys this now? I'll admit we didn't have lube. Just spit. And I wasn't empty. And we probably just didn't know what we were doing. Except for what we've seen in porns. They make it look so easy.
A
Okay, well, we can't trust porn.
B
Exactly, right? False. We're still curious and convinced that the spontaneous look of porn anal misrepresents the reality of it. But maybe since we did it all wrong, we should just try again. How do you do it? Make it fun. Or maybe it's actually supposed to hurt a little. Or maybe just not for me. And I should tell my husband. We need to stick with what we do. Well, any tips would be appreciated. And sorry if I grossed you out, girl. You didn't gross me out. I'm here for this conversation.
A
Let's talk about sex, baby. Anal sex.
B
You know, I have a friend who is heterosexual.
A
Is it me?
B
You're not my only heterosexual friend, Autumn, but. And I think it's okay that I share this because I'm not going to give a lot of detail, but I do know that her and her partner, who because she's had a heterosexual, was a man, were like having issues around specifically anal sex and went to a sex therapist about it.
A
You're all about the sex therapist.
B
The sex therapist said that like the anal topic is huge amongst. And it's not like just the gay community. It's a lot of straight people. So I think it's something that a lot of people don't talk about. And probably a lot of straight people are like, well, I don't know, I've never been straight, but it. So I don't know, maybe. Maybe someone listening can get some insight and feel like it's a little bit less taboo. If you've wanted to explore.
A
I just want to say in general, like, sex, especially when you're talking about sex with your partner, be it your husband's significant other, whatever, shouldn't be taboo. Like we talked about this in our. The episode we did a few weeks ago about, like we just said, like, let's talk about sex. And because we had a different phone, a friend issue. And believe it or not, we're getting tons of phone a friends that revolve around sex, intimacy, relations, relationships, bond, all that kind of stuff. So I think, you know, again, like you said, more people have questions or want to be able to talk about it, but are embarrassed to or their friends don't talk about it. So guess what? We're just your friends that'll talk about anything.
B
That's right.
A
And I'll probably also try anything. So I don't know why I don't have a boyfriend.
B
Me either.
A
But. But here, first thing I want to say, okay, no, porn is not real. We already know this. Right. Like these are paid actors and they're professionals. So just like you wouldn't go try to do some crazy trick that you saw Simone Biles do on the mat.
B
Exactly.
A
Without learning some things.
B
Right.
A
I would call anal advanced sex. There's missionary. That's like beginners.
B
I've.
A
Anal is advanced.
B
Anal is very advanced.
A
It requires.
B
You got to go to grad school.
A
You got to work up to that. You need to understand that there are steps to that process. Yeah, I am not a sex therapist, but I can tell you there are steps to that process. So while you see in porn is, hello, I'm delivering the pizza, all of a sudden they're having anal. That's not how it goes.
B
Yeah, or like it. Or like he accidentally slips it in ye the wrong. Like, oh, okay. That would not happen if that accident's happened. That's not going to be her response. That's for sure.
A
Yeah, she's not like, oh, oops, like, it tickles. It doesn't tickle.
B
Okay, so here's what I'll say. You, like, need to be very comfortable with your sexual partner if you're going to try anal. Like you said, it's something you get to. That's advanced and you have to prepare.
A
But wait, okay, let's back up because we'll get into all the. What. What can you do if you are gonna try it. But it. Like you said, the sex therapist even said it's a big deal. I'm gonna hurt Kent if he doesn't come get his little bulldog who keeps kicking the door right now. Meets, like, let me in.
B
Like, does he. Has he ever been in this room? No.
A
I don't understand why he's trying to get in here.
B
Like, I went in.
A
It's a big deal. Like, so the qu. Like, she was like, I don't understand. Why is it a big deal? Like, let's talk about that first.
B
Yeah.
A
We can speak about it in the gay world, but we can also speak about it in the heterosexual world because that's, you know, she's asking about her and her husband. I don't know why it's a big deal. Like, guys just get turned on by it. Maybe because it's not the norm.
B
It's like that.
A
It's just the, like, oh, she let me.
B
I think. Yeah. I feel like. And there's a lot about me, like, just. I fully am a guy. Okay. But there's a lot about me that doesn't relate because. But there are a lot of guys out there who just, I think, love the idea of taking it someplace new, you know?
A
Like, I think it's just, like, it's not the norm.
B
Yeah.
A
It's something new and fun and. Because it kind of has this taboo thing around it. Like, it's like, oh, she let me. I don't know. To me, I say, that's a couple times a year situation when he's being a good boy.
B
Yeah.
A
And there is a lot of preparing that needs to happen, especially if it's not something you're doing all the time. Because let's just be honest, that particular place. Huh. It's not meant for things to go up. It's meant for things to come out.
B
That's right. Here goes. People messing with creation. Good. No, that's an exit.
A
I would. It's the reason you don't get pregnant that way.
B
Yeah. Yeah. I think that, like, if I was just having a conversation with a girlfriend, I would say if you want it to be like, maybe in the moment you've had sexual interaction and your guy's like, can we? Or let's try or whatever. And you're like, no, I don't blame you. Say no. If you're not ready. Yeah.
A
You don't have to.
B
But if it's something you're interested in doing, at some point, you realize you get to be the one you can surprise him with it. And that would probably be very exciting.
A
It might make their head explode.
B
But you're gonna need. But you're gonna need to. You're gonna need to be planned. Yeah, but you can surprise him, and then that would be really fun. And then once you it, depending on how it goes, if you wanna do it again, then you can be like, all right, this is a conversation. Like, let me let you know everything I had to put into that cute little surprise. Yeah. Because it wasn't easy.
A
Yeah, I do agree with that. But also, you can have the conversation if you want to try it. If he wants to try it and you're open to it, fine. But. But then. Okay, again, we're saying that this is advanced. Like, how graphic are we about to be? I mean, you kind of have to.
B
Yeah. I don't know.
A
I mean, first of all, I wouldn't try. Oh, my God. I can't believe about to say this line. But you don't want to. The first thing to be his penis going up there. Can you start with a finger?
B
Oh, yeah.
A
Like, you gotta start.
B
Totally. You gotta warm it up. Absolutely.
A
Like, you're not just jumping to.
B
Well, when she said just spit, I was like, were you guys in prison? No offense. I love that you sent this in, but you gotta do more than, like,
A
you need a draw.
B
Just bit is something that, like, some people can do when there's no other option. But you have another option. My lady and I would encourage you, when you try it again, if you try it again, to definitely, like. Like you said, don't just start with. With the actives. Yeah, with like, maybe some other thing. A finger. You know, there's all kinds of things you can stick up there.
A
Okay, so we're just gonna play who is.
B
What I was gonna say, but I will say, but.
A
No, go ahead, you say it.
B
But one practical tip that a lot of people might not know of is if. If it's something that you want to try and you are planning to try, I would recommend taking a, like, really good fiber supplement. If you don't take one, because it really does. That's like. I'm just gonna be honest. I'm gon you all in on the secrets of the gay world. That is something that really helps. They even sell products that are marketed for gay men called like, I don't know, like, ready or something like that. And there it's all it is, is like, a daily fiber supplement. But I remember a laxative. You're not going to be laxative. It's not a laxative. But the thing is the fiber. Like I remember when I had my butthole reconstruction surgery. I can tell you guys about that another time. Yeah. From using spit. The. The surgeon gave me this, this supplement that had a lot of the. Is it called psyllium husk or something like that?
A
Yeah.
B
And it was because like after you have a surgery down there, you are going to be so hesitant to go to the bathroom. So I took it. And when I went to the bathroom, when I tell you I wouldn't have even had to wipe. Like, it just. It just like. And that really does help make a difference. Like you think that you're. Because in her emails, I think I was. It was empty. But it's because, you know, you just need a little more fiber. I'd say that's my one, like practical, really non. Even vulgar tip. Yeah, I would encourage you.
A
Like, I wouldn't try it. Like if you just went out to a nice dinner, then that's probably not the.
B
Do you got a short window of time? Where is the dinner? That's what you got to ask yourself.
A
Is it downstairs?
B
Yeah. Is it just traveling in your. Yeah. Because placement matters, honey. It's very important. It's like you guys set a timer. I'm ask Chatgpt. How much time after dinner am I still in the clear?
A
It depends on your digestion.
B
That's true.
A
It depends on the person's digestion. Digestion. How quick that's gonna happen. But okay, let's get real.
B
Real.
A
Let's pretend like there's not cameras there because.
B
Okay.
A
Wow. This is a hard topic, but all right, we're in it now. We gotta get practical tips about. Listen, ladies. Okay, fine. Yes. Been there, done it. It's a process. You need to be prepared for a process. You have coconut oil. Not the same one that you keep in your kitchen.
B
Or just get a separate container. We don't use your 21 day fixed containers in a while. Grab the purple one. You can use the green one for fruit and veggies. Put some coconut oil in there. Take it to the bedroom.
A
Take it to the bedroom. You're gonna need it. It's probably gonna take. If it's your first time ever trying that, it's probably gonna take you a few hours of warming that process up. This is not like a hey, honey, let's try it. And you get in bed and. Okay, just go slow. This is where. Remember when we were talking about toys? This is where you need toys.
B
Yeah.
A
Small, medium and large. Or Large enough that exactly adds up to your significant other, right?
B
It depends. Yeah, it kind of depends on, like, you want to prepare yourself for whatever
A
the size is of your significant other is big. You might want to skip this might not be for you.
B
Yeah. Bring it back to good old titty fucking. I'm just kidding.
A
Mouth and two hands.
B
Yeah. That ain't enough. Come on.
A
Oh, my God.
B
Come on. Right here. I'm so sorry.
A
Oh, geez. Okay, we're gonna be canceled after this. Nobody's doing my workout program, so
B
it is important. It is important in all seriousness to prepare and take your time. Even people like. Like gay men who. Their only sexual intercourse option is anal. Who. So you have to, like, take time. It's not the same. I mean, I don't really know that much about regular sex, regular straight sex, but it's not. I know it's not the same.
A
Like, that is something that you could just jump to pretty quickly.
B
Yeah.
A
This is not.
B
And maybe you. If you have a toy or something, you can also, like, ha. Start having some fun. Like, I don't know, maybe having traditional sex. Because you don't really want to go from back to front, right? No, you don't go from front to back.
A
You know, from front to back. You just don't want to go from back to front.
B
Yes.
A
You can wash off in between.
B
Yeah, right.
A
Because otherwise you're gonna end up with infections.
B
Yeah. Not. Not good. The doctor's visit in the future.
A
Just, like, we don't wipe from back to front, ladies. We don't sex from back to front.
B
See, I wipe from back to front. I do it all wrong.
A
Well, you don't have a lady part.
B
I know. I told my friend.
A
You have.
B
Everyone did that. And my friend was like, well, I guess nobody cares. We have shitty balls. Like, I don't have shitty balls.
A
I don't have shitty balls.
B
Please. But, yeah. So just taking your time and making sure that that sexual encounter, it's not like a random Tuesday where you're just jumping in. You need to take your time. I mean, you can do it on Tuesday.
A
But yeah, she. Okay. So she asked is, does it always hurt?
B
So my answer, I actually that I'm interested in what you're going to say about this. I think there's always a moment of, like, being uncomfortable because you're warming up and that's happening. But it doesn't have to hurt as bad as what you experienced the first time.
A
But can we just be real? Like, can we be real real? It just feels like you're shitty. Listen, guys, let me keep it real. I can only speak as a single woman, but, like, as my own person. But, like, chances are she's doing it for you, and she's maybe turned on by the idea of pleasing you. But this is not like a. Oh, my gosh. That was the. Now, listen, I. From what I understand, I have talked to girls that do really love it, so I wonder why. I don't know. Because.
B
Because, like, for a. For a man, if it actually does.
A
You have a prost.
B
Exactly. So it feels good.
A
So it feels good.
B
Even if it. Even if there is discomfort involved, there's also, like, reward. And I always do wonder, like, some women say they love it.
A
Maybe their guy's not very big.
B
Yeah.
A
But. Yeah, I would say was. It wouldn't be a.
B
It's not.
A
It's not on the menu. Yeah.
B
Yeah, totally.
A
But if you're gonna do it, it doesn't mean it has to be unenjoyable either.
B
Do you remember the first time you did it?
A
Yes.
B
Was it a long time ago?
A
Yeah, it was with my husband, when I was married.
B
Oh. And how did you guys approach this?
A
Always about me.
B
I've not been married, and I'm. I'm gay, so it's less interesting. It's sort of like, we don't have to have a conversation.
A
Put on this.
B
Like. Like. Well, I will just say, even, like.
A
Like, there's only been two people I've done it with.
B
I will. Okay. I will say as a gay man, there are times that I'm like, we're not doing that. We can do other stuff.
A
Okay.
B
And. And. And, like, why?
A
Because size.
B
Because regardless of the size, size could be a factor. But what I'm thinking is because I'm not quote ready.
A
Oh, God.
B
Like, I don't feel. And. And when you have a lot of anal, it is risky business. And, like, sometimes, you know, when you play with fire, you get on.
A
But.
B
But.
A
But for the most part, life's metaphor.
B
Yeah. But, you know, so there's just times where it's like, you know, it's not the best time to do it. And that's fine because your stomach is turning. You're like, why would I walk down that road? But I just. The reason I'm asking you is because, like, I think for, like, especially if a couple maybe is. I don't know, they don't know how to bring it up to the other.
A
Yeah.
B
Like, did it just sort of go there your first time, or did you guys have a conversation before you don't have to give deep. I'm trying to remember.
A
There was probably a conversation about wanting it. And then I think I said, okay, I was willing to try it. Like I said, the dogs are going crazy because I said to Kent, don't let the dogs out. And so he let all three out at once.
B
I thought they were like getting attacked by coyotes or something.
A
He clearly doesn't hear them at all, which is fantastic. Speaking of. So, yes. And there was, like I said, there's only been two people. One was husband, one was a long term relationship, very long term relationship conversations around it. And it sort of required me deciding, hey, we can da, da, da. Or I like the long term committed relationship. It was. It was like a. After we had had the conversation and tried it once, then I think there was maybe one or two other times where it was like a little like, surprise. But. And by surprise, I just mean, like, oh, when that happened, I was. I said I was willing and ready. And by ready, I mean there you
B
did the prep there, the preparation. You cleared your calendar.
A
Yeah, no, literally, like, that's like a process at home of like, yeah, step by step by step. And people are gonna be like, oh, my God, you're a mother and I can't believe you're talking about this live. But also, like, like, I don't know,
B
I'm definitely gonna tell my mom, hey, you might want to skip this episode.
A
I mean, Tom doesn't listen to the podcast anyway, so I'm not worried about it. But also, like, who cares? The last thing I would want was anybody. I don't want anybody, any of our listeners to have shame around it or feel embarrassment about it. Like, I. I agree. I'm not trying to, like, give all of my sexual encounters, but also, if I was sitting with a girlfriend. And that's what our podcast is, everything's perfect. You're sitting down with two friends and you're having the uncomfortable conversations. Things like, okay, I have one girlfriend. This is so funny. We've been friends for like 15 years, since Dom was like two. And she used to train with me and she's five years younger than I am. And so I remember one day we came in, I don't know, I told her squats or something, and she was like. She gave me this look, and I was like, what? And she goes on this whole story about how she was with her boyfriend the night before and d. And they're doing things, and then all of a sudden he was like, don't move. She was like, what? And then he, like, tried. And I was like, wait a minute.
B
Oh, my God.
A
Like, no preparation, no warning. And she was like, yeah. And I'm like, girl, that is unacceptable. Yeah, you. And, you know, she was younger at the time. Like, I want to say late. Late. Maybe late 20s. Probably like 28 at the time. And I was like, oh, no. You need to let him know.
B
Yeah, this is not. It's a whole different ballpark.
A
Yeah. You don't just attempt with no warning.
B
Absolutely not.
A
But it was like, the funniest story because we're, like, in the gym and she's telling me the story, and I'm listening. I'm like, on the edge of my seat, and I'm counting reps at the same time. And she's like, not. She's like, I'm not squatting right now. Like, things don't. And then I was like, why? And you know, she's like. And then he said, hold on.
B
Or no.
A
Then he said, don't move. And I was like, that is your first sign to move.
B
Run.
A
Get the hell out of there.
B
Don't move. Why?
A
Yeah, exactly. Surprise. That's not a surprise situation. So do you use. Do you use toys putting you on the spot? Do you use toys to prep yourself? Are you at the point now where,
B
like, so I'm about to ask you
A
all the questions I.
B
Or I'm at. Or am I just some loosey goosey? Maybe you're a top butthole is blowing in the wind. I. Well, I will say that Nell and I are what you call verse. So we would. There's not like a specific. Like, we don't play any harsh. Like one of us only do one or the other.
A
Got it.
B
And I don't have to do tons of preparation, but I do. But I did have a toy. I actually, my. My. I've only had a handful of boyfriends, which is crazy for what a hoe. I've been but one of my early on boyfriend.
A
When you say ho, do you just mean you've been adventurous with your boyfriends because you act like you've had so many boyfriends? Or do you mean you've dated a lot of people, but you haven't been intimate with a lot of people? Why do you call yourself hoe?
B
Because I've had a lot of sexual encounters for someone who's only had it.
A
Well, you just said you haven't had a lot of partners. Or no, you've had a lot of sexual encounters, not a lot of boyfriends. Got it. Ho okay.
B
Ye.
A
Come on, Autumn. Understand the definition of a house.
B
You're making it worse.
A
Okay.
B
Like, really spelled out for you. Um, but also, whatever. That was a. I was looking for love. Um, I would say so I did get a toy that the. It was called. Actually, my. My ex got it. It was called a trainer. And it had. It was like the thing that was. I don't know how many inches this is.5 or 6. 6 inches. And it had, like, different grooves on it. And so it's like when you. It's probably sort of like anal beads, but the in between isn't totally, like, small.
A
Right.
B
And so it's supposed to be, like, the thing. It's supposed to train you to be able to have anal.
A
Does it get thicker the further down it goes?
B
Yes.
A
Okay.
B
A little bit. And the. The last one is the biggest. 2. I think it might be a little bit longer.
A
Okay.
B
So anyways, that. But we don't. We don't use toys that much right now. Like, maybe that'll change at some point. But that's the toy that I had that was specifically for that. And it helped, but it also stressed me out.
A
Why?
B
Oh, God, I'm embarrassed
A
you made me talk about it.
B
The. The. Because, like, you. And you don't prepare the same. It's a toy because you're like, what's the worst thing that's gonna happen? But because of the end of. It was so round that it was. Sometimes it. I would be worried about, you know, there being a little doo doo on it or something. And it was always like, oh, God, what if that happens early on? This is years ago.
A
Yeah, yeah.
B
And I was really. And I didn't have. It took me a long time before I bottomed because.
A
Okay.
B
Because I was worried about that. And also I felt like for some reason, it didn't feel as vulnerable. It's like, very. If you let someone put part of themselves in your. You better.
A
You better know that person and know them well.
B
Yeah. They better mean something to you. That's all I'm saying. I mean, I'm kidding and I'm not slut shaming of. Maybe. Maybe you like random people putting themselves in your butthole.
A
That's fine.
B
But for me, I wanted it to mean. I wanted, like, it to mean something, but so I used that in the beginning because I remember I was talking to one of my gay friends in my home, you know, before I left Ohio. So I was in my 20s, and I had tried it once or something, but never, like, fully tried it enough. To be like, oh, so it feels like fireballs coming through your booty hole. And he was like, it feels good eventually. And I was thinking, this is. If you're lying to me, I'm gonna go through a lot of torture to figure this out, but I can't.
A
I'm coming back to haunt you.
B
Exactly. But. But he was right. You just have to prepare. And also, like I have used coconut oil before. But also I'm trying to think if I had a. I think you don't want a water based lube. If you get lube.
A
Okay.
B
You want oil base. Because nothing is as dry as trying to do anal and water
A
sex and water in general. It's sex in your bathtub. No, it's like you would think that that's gonna make things. No, it doesn't. You're just like, wow.
B
Yeah.
A
Why is this.
B
Why does it feel like there's no moisture and I'm in. Exactly. It's like when people call wine dry. I don't get it. It.
A
But no, it is.
B
But water sex is not wet. Talk about dry.
A
Yeah. That's just not fun. Well, I don't know if we've answered her question. I hope we have. I think look. Yes. Sometimes there's going to be oopsies. It's going to be a little uncomfortable.
B
Oopsies. You have a poopsies.
A
I can't believe this topic. But you know what? No, it's. It's fine. It's just that.
B
Well, I think the big.
A
The bigger thing is except that everybody else gets to remain anonymous and we're exactly one with our freaking faces out here.
B
I think a couple things I want to point out of this phone of friends.
A
Please.
B
I love that this couple because we get a lot. We've had a handful and more that we haven't read yet of couples who are feeling like disjointed sexually. And I love that this couple felt like great and confident enough to try something new and spice it up. And yeah, I, I think that that's awesome and I think that really what it is and. But I feel like I'm still working on too even like Nell and I have been together for two years feeling comfortable expressing your interest or needs or curiosities around sex because so many people just don't talk about that. And then they fall into a rut and they like both partners could be thinking about, well, what if we try this? What if we try this? What if we tried this but almost feel embarrassed to bring it up to their partner and I am like, talk about. Talk about a cause to stand behind. I think that people should feel so confident and comfortable exploring and talking about, like, the sex.
A
I do think you have to normalize that quite a bit. Like, if with nobody else, like, you have to talk about it with your partner. Like, she even said in her email, where do I learn? And honestly, I don't have an answer for that. I think it's it for me. It's just been trial. Like, okay, what do I think would make this process? What do I think would. You know, part of it is having a partner who you can talk to and say, what do we do? How should we. Like, asking the questions, having the conversation, trying things together, being okay. Being a little awkward, knowing when to pivot if you're trying something and it's just not working. So that the whole. Go well, so the whole night doesn't go off track. And you don't, like, walk out of the bedroom feeling like that was super awkward, you know, like, really having the conversation and being present and being in it and being patient with each other. He might be just as intimidated. He doesn't want to hurt you. Trying that process. And so, like, having some foreplay first of all, leading up to it, really, like, building the moment. Okay, maybe you want to start with normal sex. Get that part. Get your pictures and let him try his. But I do think, like, even though it's a hard conversation to have here on a podcast publicly, because that's.
B
Because I'm talking about our butthole.
A
Normally I could talk about fitness and lifting weights and eating your macros, and now it's like, hey, by the way, just talk about tossing salads.
B
Yeah.
A
But also, like, it is hard because so many people won't talk with their friends about it. And it is like, I don't know, what do you Google? Like, I wonder what would come up if you were like, how do I really do anal? Like, I mean, I'm sure there's probably books and things that you could read, but, like, that feels.
B
So I do have another piece of advice. If, like, you're a female, like, for her or anyone else in that position. I don't. It depends on how you and your partner have sex. Like, if. If he is a really aggressive, like, whatever. That shouldn't be expected the first time you do this. And maybe, like, it should definitely start with you on top so you can control how. Like, how you can control it.
A
Right?
B
You can control.
A
I was just gonna. Yeah, yeah, I was gonna say, you gotta take into consideration there's more than one way. More than one position to be in.
B
Yes.
A
To do it.
B
Yeah.
A
And who's in control and how fast does it go and Right. What position is comfortable for her to be in?
B
I. I feel like. Like if I do that, it's more comfortable for me to. To physically be on top then otherwise, like it feels even more like it's in your guts. Your. If your legs are up here and you're laying down and they're going, oh,
A
no, not that way.
B
Have you never done it that way?
A
No stomach.
B
Yeah.
A
No. Lay on your stomach or on top. But no, I would definitely never. Legs over my head.
B
Oh, well, over my head. I mean, can you imagine me with my hamstrings? I'm just trying to make it sound cute.
A
Actually.
B
It's more like. But the point of this advice is
A
we might need a whole different episode. This episode cannot go off.
B
Is. Is you should start on top and it should be okay. If you have the conversation with your male partner like that you're experimenting and playing with it like it's something that might come in phases.
A
This might be the first time. Might be just the dip.
B
Exactly. And that's okay.
A
That's okay.
B
Yeah.
A
And then a little while later, maybe it's a. Maybe it is, maybe it isn't. But like.
B
And you can always say you tried.
A
There you go.
B
Yeah.
A
Yeah.
B
So I don't know. But I definitely think there's way it does get less painful. It never is good. It's gonna be a different sensation. But it does get okay.
A
So I think we've covered all things anal for now.
B
If we missed something, you guys feel free to let us know.
A
But I hope our listener that wrote in hears this. And I hope. Hope that she gets back to us. If they are to try anything again and let us know. It's like Sleepless in Seattle. Let us know. Yeah, let us know how it turns out.
B
We did get another phone friend.
A
Yeah, we're gonna do two in this one because this is a pivot.
B
But still about a. Still intimacy. Exactly. So I'll just start at the relevant part. I grew up similar to donald in a very 90s Christian home. I love that about myself and love my par for it. My faith is so important, but I grew up with a screwed up view of sex. I honestly. I'm sorry. I was honestly afraid of it and afraid of any feeling that I had regarding it. Same. I just want to say I know it seems wild because we just talked about anal for 30 minutes, but I relate to that so much. And that's why I like talking about it, because I want to break the stigma. So anyway, I'll continue. Okay. I'm so shy when it comes to boys. But later in college, the hormones kicked in with boyfriends or during fun nights out with friends. I found myself in situations where I really wanted to have sex and it should have been okay. It was safe and fun, but I couldn't have fun with it. There was so much shame and guilt. I had to sneak around and be careful not to enjoy it too much. I would always tell myself it was a mistake. Fast Forward to age 28 getting married and my now marriage of over a decade. My husband wanted me when we were dating and we did, quote, slip up and have sex a couple times. It was vanilla. And I always felt guilty during and after. I couldn't wait to be married and the shame and guilt to go away. I was ready to enjoy sex. No more vanilla. Well, all these years, married, successful careers, four kids, I'm still looking and feeling amazing. Thanks to you and body. Autumn I. I'll be 40 in March. The guild is gone, but the enjoying sex hasn't happened. The fire was never lit under my husband. Sex happens maybe twice a month if I'm lucky. It's quick and almost feels like we are just meeting a need for him. I've shared that I'm not happy with our sex life, but he doesn't seem to care and I have no clue how to fix it. I've tried flirting and kisses to no success. The question after this many years in a committed relationship, I want to have good sex. How do I approach this without hurting his feelings? Where do I learn things? Remember, I'm shy and probably awkward on this subject. I'm almost 40. I'm ready to enjoy sex and finally have an orgasm.
A
Okay. Oh God. There's a lot to unpack there. So yeah, big pivot away from anal and the couple being happy to try. Yeah. Okay. Well one, I wonder if she's given herself an orgasm.
B
You know, it is wild. Like I. I hope so too. Like, I wonder if that means have an orgasm from her partner. Yeah, yeah.
A
Her husband.
B
But there it's wild to learn that there's like women who have never orgasmed.
A
It's not easy. It's not easy for women. It's not like guys where like you get the friction going and you're going to come.
B
Yeah.
A
And you have to feel. I. Look, I'm sure for some women it's different, but for a lot of Us, you have to feel really safe. You have to feel really comfortable because you have to, like, let go to have it happen. And it takes time. And so if he's a wham, bam, thank you, ma' am getting his, which it sounds like selfish, I wonder, too, if his upbringing is the same as hers. Maybe it sounds like it because she said they slipped up.
B
Exactly. They must have been on the same page about that.
A
So maybe he still has guilt around it, or maybe he has this sort of, like, Madonna complex about her being the mom of his four kids and that not being right. That's a hard one because she said she's had the conversations with him and he just doesn't seem to care.
B
I mean, I don't know, because the question is, how do I bring it up without hurting his feelings? But didn't she say she's made it known without hurting? Yes.
A
So she's made it known already.
B
I think that, again, is like what we were saying earlier about talking about it. But I think that this is just one of those things where you have a choice, and your choice is to live the rest of your life in a relationship that seemingly, in a lot of ways is great, but you're unsatisfied sexually. And you. And I, like, for some reason, I'm such an ally for women who are in that position, because I feel like women have been made sexual objects, but not given a lot of space to be sexual beings, especially in this kind of world.
A
You're like a slut if you want to enjoy it and you want to be explorative and.
B
Exactly. But I tell you what, like, what is a relationship if you can't have the hard conversations? If you can't say, like, you know, I. Especially if you came from the same place, maybe I would approach it that way. I feel like because of how we were raised, we might have some even unaware internal issues around sex that we need to address. Because I'm. I'm not feeling fulfilled. But what I would say, too, I would. And I would end that sentence with and I. I don't want anyone but you.
A
Right.
B
But I want our relationship, sex, sexual relationship to become stronger.
A
I do think at this point, like, they're. She said over a decade in four kids, she hasn't had an orgasm from him. So the question is, is, are you faking it? Know you haven't had an orgasm from him? Because we talked about this in the other episode. You. You can't fake it and then expect him to do something different because he thinks he's satisfying you. So if he thinks he's satisfying you. Look, at this point, it might be that his feelings get a little bit hurt. And I'm not saying be mean about it. I'm just saying you kind of have to make it known that you're not getting all of your needs met.
B
Yeah.
A
You could let them know I'm attracted to you. I like I. But I want it more often. Maybe his libido isn't there.
B
Maybe there's something his testosterone checked. Maybe.
A
Right, but that's still a conversation.
B
But.
A
And if he doesn't. The thing is, is if he doesn't care and he doesn't and he's fine to only have sex twice a month, it is a harder conversation or harder to get the person to do things to. Whether it's see a sex therapist or even have the conversation or try something new. But a hard conversation has to be had. You have to be okay with the fact that. That he might get his feelings hurt a little bit. Not because you're being mean, but because you're being honest. You could be careful or you could be delicate about being honest, and you could be very kind about it, but you still have to be very clear that your feelings or your needs aren't being met. I mean, there's one real easy way you could let him know. At the end of sex, if you're not satisfied, roll over and pull out a vibrator and finish yourself off. And if that doesn't tell him that something was missing, I don't know what will. And honestly, if he doesn't, that's a bigger concern, I would say, like, if he could care less that you have to then get yourself off a different way. Yeah, that's. That's a deeper conversation. Like you said, you have to decide, are you willing to. Okay, most of the marriage is good. And so I'm not worried about this part or I want to be able to fully enjoy and express myself in this manner with the person I'm with. And you're not willing to do that with me. Yeah, this is where it gets hard. Look, it gets hard. I don't think it's just religion that necessarily, like, I. Obviously there's certain religious upbringings and people do have a lot of shame and guilt, but I think there's just a lot of households that put shame and guilt around sex so much that as adults, there just isn't conversations. And people act like it's not supposed to be a big deal or not supposed to be a big part of a relationship. And it is. If we were not supposed to be attracted to each other, if we were not supposed to be sexual beings, things, we just wouldn't be. Like, we wouldn't have the desire all the time. And I do think we live up in this, like, kind of fucked up space of making somebody feel bad, guy or girl, for wanting sex and wanting to enjoy sex. I'm not talking about in some like, inappropriate, dirty, illegal way.
B
Yeah.
A
I'm talking about with your committed partner.
B
Right.
A
Or in a relationship, whatever that is.
B
Two consenting.
A
Two consenting adults. That's what I'm saying is people act like it's so shameful. If you're being safe, you're taking proper precautions, you're being responsible. We probably have a lot more happy people.
B
Yeah. I think another thing is people just need to switch it up. Like maybe if, if you try to awaken your sex life. We've touched on this before, and you are always trying to have sex at the same time in the same room, in the same. You might just like, you might need to like, be in a different space, try a different time of day. All of those things matter. Like, and I think that that could, could help. But also at 40, you know, if they're around the same age, then he might, he really might also the conversation needs to be had and he might be happy if he can get his. If he. Maybe his hormones or something need to be.
A
Yeah.
B
Looked at.
A
Yes. It's interesting. We don't have all of the information. Obviously, if you were sitting with your friend, you'd be able to ask them more questions. But she said the fire was never lit under him. They slipped. He wanted her when they were dating, but then they got married and the fire was never really lit. Like, he never seems like now you have four kids, so. But if it's twice. So in most. Yeah. Most guys would kill for a woman to be wanting it. But I get it there sometimes. So the question is, is, has the hormones always been off again? Is it more of the Madonna complex? Is it Some people just aren't into it. That's also a thing, though. Some people are just very sexual beings and other people are just not as much. No shame on either side of that. But when you put two of them together and they're not in alignment. Alignment, you do run into a problem.
B
You have some choices.
A
You have some choices to make decisions. Yes. And. And that's hard because when you're in love with somebody or when you have a whole family together, you're now you're going to start to feel selfish because I'm picking my needs and over the family, and only you can make those decisions. I always go back to two things. You have one life to enjoy. I'm not saying that you need to leave your husband and go be a hoe. That's not what I mean at all. But you need to have the hard conversations.
B
Yes.
A
And I always say, like. Like, if my kid was to come to me later on and be like, mom, we need to talk. I'm really struggling in my relationship because we're at odds here, and I don't know what to do. I would give every bit of advice to try everything to make it work. But I would also want to say, if you've tried and it's not, and you don't believe that you're going to be happy or that. That she, you know, like, then find a way out of love to release the person so that you both can be happy.
B
Yeah.
A
And I know that that is not the normal opinion. I know that that is a hard thing to say. And I'm. Again, I'm not making it all about sex. I'm not saying, like, oh, you know, you're just not having sex all day, every day, so leave. That's not what I'm saying at all. What I'm saying is everybody deserves to live their best life without guilt around it.
B
Yeah.
A
And so that requires hard conversations. It requires some effort, and it also requires understanding what you are and are not willing to accept for yourself.
B
Yeah, totally. I mean, at the very least, the hard conversations part, it's like you're afraid. I've had conversations with people. It's like, what is the worst case scenario if you have this conversation? Because right now you're kind of in the worst case scenario. Do you just want to stay in it?
A
It's not. The worst case scenario is that you end up divorced. That's what. That's why that conversation is hard. Because let's be honest. Like, let's have a real honest conversation. The worst case scenario to a lot of people is that you have to get divorced. You have to put your kids through it. You have to put your families through it. You have to put yourself through it. There's a financial burden that comes with that of, like, now I have four kids and they have four kids, but we're, you know, on my days, I'm gonna have to take care of four kids. On his days, he's gonna have to take care of the four kids. You go from Maybe a two household income to, you know, there's all these things that come into play that it's going. You're. You're going, is it the worst that the sex is vanilla or is it the worst that I'm out there in the world alone? And alone is scary. And I. Because I'm in it. And it sucks. It sucks to be alone on the holidays. It sucks to be alone on your birthday. It sucks to have to open yourself, to try to trust somebody, only for somebody to hurt you again. So you, you weigh the odds, you weigh, you weigh the lesser of the two evils. And that's why we're saying it is a choice you have to make of, do I stay here, that's safe. That I know. I know what this is, and I know how to operate within this, and I know where my happiness lies. And okay, fine, maybe I just need to take care of myself a little bit more often. Whatever. And again, I'm speaking like, if you have all the hard conversations and try things and it's not gonna change and some people will decide, I still would rather be here. I mean, they say next to lose, like the death of a loved one, a divorce is the hardest thing to experience. It ain't easy.
B
Yeah.
A
So I'm not by any means advocating for divorce. That's not what I'm saying.
B
But that is people.
A
But that is.
B
Is fear of like, going into those difficult.
A
Yes. Because when you open that can of worms, you can't really put the lid back on.
B
Yeah.
A
And so it's like, if I open this, what. When you say, what's the worst case? That's where they go. And it's like, oh, am I willing to open myself up to that possibility?
B
Yeah, I do. Just also, for anyone who's listening, who's feeling connected to this, just second phone a friend. I know a lot of stories of couples who have made it through those difficult times.
A
Yeah.
B
So even though, like the worst case scenario in your mind is that you can't survive it, also you could come out so much stronger in your relationship by choosing to have those hard conversations. I definitely think it's not something that you should say in the heat of a moment like pe. Like, you know, if you. A man's ego is important to be considerate of, especially when you're talking about their sexual performance and stuff like that. But that doesn't mean that you don't get to bring up the conversation. I would just say be very intentional and respectful and, you know.
A
Yes.
B
Work through how you're going to talk about it. It might not be comfortable for him, but that also doesn't mean it's going to be offensive to him either. And you. But there can be a very healthy, robust fun. Like, you never thought there would be sex life with your partner on the other side of that. It just takes work. Unfortunately, everything takes work.
A
Listen, it's not nine times, like, 99% of the time, it's not going to be easy. I would love to say it is. I think, you know, if you are lucky enough to find that person, that unicorn. And it works, that. That. God bless. And even then, it doesn't always work out.
B
Yeah.
A
So takes work. Nothing's. Nothing's perfect. Just texting me. But yes, you do have to be respectful of how you do it. Like, this is not in the heat of the moment when you're not satisfied being like, God, yeah. Like, this is not a conversation to have when the kids are home screaming for your attention. Like, this is a. That's a loving, very loving conversation that needs to be had.
B
Yeah. Yeah.
A
Wow. We've just gone all the way around
B
that circle and we're literally circle again.
A
Not the rim.
B
Moving back to the butthole. By the way, I heard drag me one time. Be like, she was doing her performance. My favorite part of drag shows is the jokes they tell in between their acts. And she was like, how are you talking? The crowd and the guy, they were like, he's straight. And she was like, he's straight, honey. He's as straight as my. And that's a circle. It's like, okay, I love that. I love it.
A
Amazing.
B
So anyways, full circle.
A
Here's what I will say. We have gotten quite a few phone friends and quite a few of them revolve around again, sex, intimacy, a little bit of trouble in those areas. So it is a topic. It is a thing. Maybe some more guys need to tune into our podcast so that they can understand that. Like, maybe you need to be a little more aware of what your lady is experiencing or not experiencing. But I hope, I hope, really, even though we're having fun with it, like, you know, like, what else can you do but laugh through a conversation about analysis?
B
Yeah.
A
Be honest and real. Or you don't bring it up. But, like, I, you know, I think neither one of us wanted to ignore it because it's a real question.
B
I think, like, what we get to like, honestly, this is. Sounds so dramatic, but the good work that we do in this podcast, because we don't have any magical remedies for what people are facing or anything like that. But we get to normalize conversation.
A
That's the biggest thing.
B
And I love that because I think that. That more people than you know are in a similar situation that you are in.
A
Yeah.
B
And it's good for it to be normalized. I feel like, okay, I'm not the only one feeling like this.
A
I'm not alone. Yeah. I'm not the only one feeling this. Or I'm not the only one enjoying it on this side. Like, oh, I'm so glad I'm not like this crazy oneoff freak.
B
Yeah, yeah. Yes, it is.
A
It's just so. Yeah, I like that we're getting to have the conversations. I mean, if the. If the phone of friends keep coming in, I guess we're gonna keep responding to them like it is what it is. We'll keep having the discussions as they come in and as you send in other topics, we'll explore those too. But so far, we've had a lot of sex topics.
B
Yeah. A lot of those.
A
Can't ignore them. When they keep coming in, it's like, ah, wow, okay.
B
But we do love it. We love diving into it. And we would love, as always, we say if you have. If you want to hear our take on something that you're facing or maybe someone, you know what they're going through, we'd love to hear your stories and talk about it.
A
Everything's perfect. Podcast gmail.com and you can also check
B
us out on Instagram. It's Everything's Perfect official. And we love to connect with you guys. So we'll be looking for your messages.
A
We'll see you next week.
B
See you.
Episode: Everything’s Perfect…Except No One Talks About This
Date: March 3, 2026
Hosts: Autumn Calabrese ("A") & Donald Stamper ("B")
In this candid and laughter-filled episode, Autumn and Donald dive into sex—the awkward, the taboo, and the questions nobody asks out loud. Responding to two listener emails ("phone-a-friend"s), they break down the realities of exploring anal sex in heterosexual relationships and unpack the complex challenges around shame, desire, and dissatisfaction in long-term marriages. The episode’s tone is real, warm, and humorous, acting as a safe space for honest conversations about intimacy, personal growth, and destigmatizing what everyone is thinking, but few want to say.
Preparation is Everything:
Honesty about Experience:
Autumn and Donald model the kind of friendship where literally nothing is off-limits—they keep it light, real, and deeply supportive. The episode is explicit, honest, and full of practical, unvarnished advice—making it a refreshingly judgment-free resource for anyone wrestling with sexual shame, new territory, or the daunting work of keeping the intimate parts of life vibrant and open to growth.
If you have a question, you’re not alone. Their biggest message? Let’s talk about it, because everything’s perfect… kind of.