Dear Chelsea - Minisode: Big Boyfriend Problems with Yamaneika Saunders

Episode Date: July 11, 2025

A positive update from a favorite trans caller.  Then: A new boyfriend’s nether-regions overwhelm.    * Need some advice from Chelsea? Email us at [e-mail] * Executive Producer Catherine Law Edited & Engineered by Brad Dickert * * * * * The views and opinions expressed are solely those of the Podcast author, or individuals participating in the Podcast, and do not represent the opinions of iHeartMedia or its employees.  This Podcast should not be used as medical advice, mental health advice, mental health counseling or therapy, or as imparting any health care recommendations at all.  Individuals are advised to seek independent medical, counseling advice and/or therapy from a competent health care professional with respect to any medical condition, mental health issues, health inquiry or matter, including matters discussed on this Podcast. Guests and listeners should not rely on matters discussed in the Podcast and shall not act or shall refrain from acting based on information contained in the Podcast without first seeking independent medical advice.  See omnystudio.com/listener for privacy information.

This is an iHeart Podcast. If you're looking for another heavy podcast about trauma, this ain't it. This is for the ones who had to survive and still show up as brilliant, loud, soft, and whole. The Unwanted Sorority is where Black women, Femmes, and gender expansive survivors of sexual violence rewrite the rules on healing, support, and what happens after. And I'm your host and co-president of this organization, Dr. Lea TraTate. Listen to The Unwanted Sorority, new episodes every Thursday on the iHeartRadio app, Apple podcasts, or wherever you get your podcasts. So what happened at Chappaquiddick? Well, it really depends on who you talk to.

There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. Summer's here, and with the kids home and off to camp, it's easy for moms to get lost in the shuffle. On Good Moms, Bad Choices, we're making space to center ourselves with joy, rest, and pleasure. Take the kids to camp. You know what? It was expensive. But I was also thinking, you have my kid.

This is kind of priceless. Take her, feed her, make core memories. I don't have to do anything. Main thing, I don't have to do anything. To hear this and more, listen to Good Moms Bad Choices from Black Effect Podcast Network on the iHeartRadio app, Apple Podcast, or wherever you get your podcast. Ding dong, Las Culturistas calling from YouTube. You heard that right. Las Culturistas now has its own YouTube channel. Check out full episodes, iconic interviews, visual bits and culture moments that will change your life. All in stunning HD.

So don't wait. Be sure to watch Las Culturistas on YouTube at youtube.com slash at las culturistas Ding dong las culturistas calling from YouTube Hi welcome to a mini episode where these are mini so we have a special guest on our mini set her name is Yamanika Saunders Yeah, hi Katherine. How are you today? Hi, Chelsea. Hi Yamanica. Hi Yamanica, hi Yamanica, hi! I adore you guys, this is crazy. How are you? I'm good, I'm so good.

Okay, bye. Bye. Okay Catherine, what do we got with Yamanica today? Alright, well our first thing that we have up is a follow up from a wonderful caller we had, Witt, who called in on our John Lovett episode. He was wrestling with whether or not to reveal to his longtime girlfriend's family that he's trans. So I checked in with him and Witt said, Oh my goodness, hi, it's really nice timing to hear from you and give you an update. We ended up telling them, well, my partner did, in a very casual conversation back in November. Long story short, they received it very well,

were honored that we trusted them with the information enough to tell them, and also said it would have been okay had we chosen not to tell them. At first I thought, oh damn, maybe we didn't need to say anything, but ultimately it was a huge weight off my shoulders. Yeah. Never in the moment, and he was worried about like, are they going to ask awkward questions? Never in the moment nor since then have they asked any inappropriate questions and really just were happy that my partner was happy and could

see the genuine love between us. And this week I proposed and we're now engaged. Prior to asking her, I had a conversation with her parents about my intentions, hoping to have their support. They were nothing but thrilled and happy to welcome me into the family. Thank you for this insight. It helped make the decision based on what I really wanted without thinking about what their reaction would be, but it also helped me have conversations with others about the sensitivity of the topic should they be on either side of the conversation.

Thanks again, come to Canada for the wedding. Cheers, wit. Wow, that's nice. That's a nice result. But what would make sense? Because her family didn't know that he was trans and she The partner's family. Yeah. The partner's family, his girlfriend's family didn't know that he was trans and they didn't know if they should tell them or just like leave it off the table.

And I don't even remember. I think I said to have her do it in a casual way if they feel inclined. Right. Yeah. Yeah. They don't need to know that he's trans. But like if they want to tell them that it's not really his. I don't remember what the fuck I said quite frankly. No, that's exactly what you said. You were like, if you really need to. And I know it was this sort of thing where some things were coming up where it's like, oh, we're going on a beach vacation together soon. So people are going to be in, you know, swimsuits and I will too. And like they're a scar, you know, different things that he was like,

I don't know if I need to explain this ahead of time sort of thing. Yeah, people be having scars and shit. I got key loins all over the place. Yeah, well, that's a little bit different than being trans, but okay. Anyway, anything else, Catherine? Well, we do have a caller and Yamanique, I'm very interested to hear, well, actually both of your advice on this. Okay.

Here we go. So, Michelle says, Dear Chelsea, I've had your email address saved in my drafts for like two years. I've had many things that I've wanted to consult with you about, but things come and go. I'm currently reading your newest book. I'll have what she's having and wanted to tell you how much I love it. I just read the chapters on poopsie, whoopsie, and oopsie and shed a tear. This coming from a girl who never cries.

I do have one dilemma currently in my life, and if you've ever experienced this, maybe you'll have some insight. I just started dating a man who seems great on a lot of accounts, except for one small or not-so-small problem. He has a really huge penis. I don't say that in a lighthearted way

or a joking way about how some women want a big cock. I joke with him and tell him he has a double dick. It's literally double the girth of a quote-unquote normal penis. We've tried to have sex a couple of times, but it just doesn't work. If it goes in, it hurts after a few seconds for me. He's age-appropriate, has education and a good job, and is loving, sweet and communicative. So I would love if this would work, but I also can't wreck my body for it. Any advice or experience, Michelle? Oh, God, I've never had a penis that was so big that it didn't fit, that it didn't hurt. So you can't even get it. And are you like lubricated and ready to rumble? Yeah, I mean, we've tried it a few times. I mean, I can't even get my hand around it. Oh, God, that's too big.

It's too much. I mean, hello. What do you have to say, Yamanika? Have you ever experienced a penis that was too big for your pocket too? The ways in which my vagina has other stories that can be told is crazy. The way in which your vagina can adapt to a large penis,

is that what you're trying to say? I have a very tight vagina. And so a lot of times it is hard for things to get in there. But I also have a competitive go get a spirit. And does he know that he is too big? You've told him this, right? He played it off at first, like, it's not that big.

Come on. And I'm this, right? You know, he's like, he played it off at first, like, it's not that big. Come on. And I'm like, what after a few times, I'm like, has this been a problem in the past? And he's like, yeah, it's been a problem. And he feels bad and he really is trying and I am trying and we haven't had one successful session. Oh, how did that go? Yeah, what was going on there? Do that.

So, well, I think it's like a combination. I quit drinking for about a year. It just wasn't serving me, but I decided I needed to try drinking again. Yeah, take that dick. Yeah, yeah. He got that Hennessy dick. So, I had a few drinks. I also did some research and I found this herb called Damiana.

And basically it's like a supplement that you take every day. And it's supposed to like help your lining and your wetness and everything. And I feel like the combination of that, my nerves were settled a little bit from the alcohol and not being nervous at this thing coming at me. And it still hurt a little bit from the alcohol and not being nervous at this thing coming at me. And it still hurt a little bit. And I feel like if we keep trying, I'll just adapt more. But it's huge. I believe you.

I believe that it's very big. And I understand that that's unpleasant. But if you really like this guy, I mean, you can warm up your vagina to a bigger penis. It works. You know what I mean? Like you can get your vagina acclimated. I just worry after the honeymoon phase is over and you're really like, then what do

you do with that big dick that's coming at you all the time? You know? Well, I'm worried like if I move on to another person, not that that's the plan. No, it retracts. It retracts. Yeah, don't worry. It goes back. It's like when you have a baby, your vagina goes back.

You know what I mean? Like, it can come recover from a big dick. I have definitely had bigger penises and then it's gone down and it's like, oh, I can still feel when I have sex with somebody who doesn't have such a big penis. It's not like my vagina is stretched out, you know? Can you close your mouth? Are you getting ready to open your mouth, put that dick in your mouth? Because it looks like you want a dick in your mouth right now.

Is that what you want? I was just, I didn't, I looked at you the second you said something about your pussy being stretched out. God bless whatever's going on. You have to be comfortable with him. It's, you know, and like I agree with everything Chelsea said, after the honeymoon phase and you got to keep, you know what I'm saying, seeing them around with this nonsense, it's gonna be like, get outta here, you know, scram, you and your penis gotta get outta here. But I've never had a dick that I,

there's been times that I definitely thought maybe I felt him in my throat, but never a dick that like made me tap out. I feel bad for him. I mean, this won't even go down my throat further than this. And the thing is, it's more like triangular shape. So like at the base is wider. Oh, God.

Oh, OK. I never seen anything like it. And you're really, are you really into him? I really like, everything else about him is great. And it's so rare for me to find. Yeah, tell him to eat it first and then see what happens. Yeah, he got to put, OK, Yeah, he got to put the work in. Oh my God, this is a real dilemma.

I wish we knew how to open up your Pikachu more. Well, have you tried a lot of different positions and like lots and lots and lots of lube? Yes, yes, both. And so I think we've ruled out that we cannot do mission. It's just it goes too deep and like from behind is perfect because it can't go in all the way. Yeah, and you can kind of move so it's not like going as deep sort of thing.

Yeah, yeah, yeah. Okay, well that's progress. Yeah, I like that. At a certain age you like doggy style. You ain't gotta look at them, you can do other things. You can do your accounting. Yeah. Go through Instagram.

Yeah, yeah, B1 Hinge looking for another man with a smaller dick. You can do all this kind of stuff. But I've got that same go get them attitude. I hope it works out. I wish we had better advice for you. Well, this, I mean, if anyone has the same problem. It's called Damiana? Damiana.

I feel like this is really helping me. Okay, so that's to get your juices flowing a little bit more. Like, loosen things up. Yeah, because I am at like a perimenopause age too. Yes, of course. And everybody, there's a lot of people that can't have sex when they're going through perimenopause

where it feels like razor blades. Like you really want, also, are you on estrogen and progesterone? No, I can't take any hormones. Oh, you can't? So you're supposed to just go through perimenopause with no help? I don't ever want to get to the point where Dick feel like razor blades. I know, but sometimes that can happen

when you go through perimenopause. So she needs all the help she can get. I'm a perimenopause. I know, I know. I'm the one who told you you were. I knew I was in perimenopaws the day before you told me. You told me second, not first. Okay, this is not about you. This is about our caller. She's got an amazing problem. She has the biggest penis in the world.

You do have a good problem, okay? Oh man, I wish I had one. I really feel for this guy because if it's been a problem before, I know girls who can't deal with big dicks either. I've heard this story before. I don't know if it's the same guy. But anyway, I mean, I wish you well. I wish you luck and I hope that it works out for you guys. I hope it does.

Thanks. Yeah. Okay. Yes. Blessings to y'all. Blessings. Yeah. You need a blessing.

Okay. Take care. Thanks, all. You too, bye. And that concludes our mini-sode for today, I think. Right, Catherine? I think we're done with Yamanika here. She's sitting here. Did you see her mouth open as soon as this woman described the dick and the girth of it? Did you see Yama's mouth just become a jar?

It was open, waiting for the enormous thing. She was ready to receive it. Immediately you open your mouth. I mean, that's what kind of sick fuck you are. If you didn't have any type of reaction to what she was describing, there's something wrong with you. There's a whole lot wrong with you. I had a reaction.

I didn't open my mouth. That wasn't my reaction. Yeah, I had to think about it. It was so much to think about, I couldn't even hold my mouth out. I want to thank you for having me. I appreciate everything. Yeah, thank you for coming. Bye.

So, I added a couple of new dates. I'm not on tour yet, but I added a couple of dates just because I felt like we need a little bit more laughter and a little bit more medicine for the end of the year. And I was wrapping things up, but I thought maybe let me do a couple more. So I'm adding three more dates in addition to my Vegas residency. I'm doing West Hampton Beach August 21st. I'm headlining the Rochester Fringe Comedy Festival September 13th. And I will be in Napa on October 3rd.

So those will be my last dates of the year. Do you want advice from Chelsea? Write into DearChelseaPododcast.com. Find full video episodes of Dear Chelsea on YouTube by searching at Dear Chelsea Pod. Dear Chelsea is edited and engineered by Brad Dickert, executive producer, Catherine Law. And be sure to check out our merch at ChelseaHandler.com. If you're looking for another heavy podcast about trauma, the Saint it. This is for the ones who had to survive and still show up as brilliant, loud, soft, and

whole. The Unwanted Sorority is where Black women, femmes, and gender expansive survivors of sexual violence rewrite the rules on healing, support, and what happens after. And I'm your host and co-president of this organization, Dr. Lea TraTate. Listen to The Unwanted Sorority, new episodes every Thursday on the iHeart Radio app, Apple podcasts or wherever you get your podcasts. So what happened at Chappaquiddick? Well, it really depends on who you talk to.

There are many versions of what happened in 1969 when a young Ted Kennedy drove a car into a pond. And left a woman behind to drown. Chappaquiddick is a story of a tragic death and how the Kennedy machine took control. Every week we go behind the headlines and beyond the drama of America's royal family. Listen to United States of Kennedy on the iHeartRadio app, Apple Podcasts,

or wherever you get your podcasts. Summer's here, and with the kids home and off to camp, it's easy for moms to get lost in the shuffle. On Good Moms, Bad Choices, we're making space to center ourselves with joy, rest, and pleasure. Take the kids to camp. You know what, it was expensive, but I was also thinking, you have my kid.

This is kind of priceless. Take her, feed her, it was expensive. But I was also thinking, you have my kid. This is kind of priceless. Take her, feed her, make core memories. I don't have to do anything. Main thing, I don't have to do anything. To hear this and more, listen to Good Moms Bad Choices from Black Effect Podcast Network on the iHeartRadio app, Apple Podcast, or wherever you get your podcast.

Ding dong. Los Culturistas calling from YouTube. You heard that right. Los Culturistas now has its own YouTube channel. Check out full episodes, iconic interviews, visual bits and culture moments that'll change your life. All in stunning HD. So don't wait.

Be sure to watch Los Culturistas on YouTube at youtube.com slash at Los Culturistas. Ding dong. Las Culturistas on YouTube at youtube.com slash at Las Culturistas. Ding dong, Las Culturistas calling from YouTube. This is an iHeart Podcast.