Minisode: Big Boyfriend Problems with Yamaneika Saunders

Summary

Dear Chelsea Minisode: Big Boyfriend Problems with Yamanika Saunders

Release Date: July 11, 2025

In this insightful minisode of "Dear Chelsea," hosts Chelsea Handler and Katherine, joined by special guest Yamanika Saunders, tackle a delicate and intimate listener concern. The episode delves into the complexities of sexual compatibility, personal boundaries, and effective communication within a romantic relationship.

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Introduction & Context

The episode begins with Katherine welcoming Yamanika Saunders, setting a warm and open tone for the discussion (02:15). Prior to diving into the main topic, Chelsea shares a follow-up story from a listener named Wit, who courageously came out as trans to his girlfriend's family. This segment highlights the show's commitment to addressing personal and sensitive topics with empathy and support (02:37 – 04:00).

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Michelle’s Dilemma: Navigating Physical Compatibility

The heart of the episode centers around Michelle's dilemma, presented by Chelsea Handler (08:26). Michelle expresses her deep affection for her boyfriend but struggles with the physical aspect of their relationship due to his unusually large penis, which causes her significant discomfort and pain during intercourse.

Key Points Discussed:

1. Physical Challenges:

   • Michelle describes the difficulty in sexual intimacy, noting that despite their efforts, attempts often result in pain (09:21).
   • She humorously mentions referring to her boyfriend's anatomy as a "double dick" due to its girth (09:21).

2. Emotional Impact:

   • The discomfort is causing Michelle considerable emotional strain, making her question the sustainability of the relationship (09:39 – 14:22).

3. Efforts to Adapt:

   • Michelle has experimented with different positions and ample lubrication to alleviate the pain, with limited success (10:54 – 14:03).
   • She also explores natural supplements like Damiana to increase comfort and reduce nerve sensitivity (11:05 – 14:22).

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Advice & Insights from Hosts and Guest

Katherine's Perspective:

• Acknowledgment of the Issue: Katherine empathizes with Michelle's situation, acknowledging the genuine challenge posed by physical incompatibility (12:03).
• Encouragement of Adaptation: She suggests that with patience and mutual effort, Michelle can acclimate to her boyfriend's size, emphasizing the importance of both partners' willingness to adapt (04:29, 10:31).

Yamanika’s Contribution:

• Personal Experience: Yamanika shares her own experiences with tightness, offering practical advice on how to approach the situation (10:31 – 15:09).
• Emphasis on Communication: She underscores the necessity of open dialogue between partners to navigate such intimate challenges effectively (12:58 – 15:09).

Chelsea’s Suggestions:

• Practical Solutions: Chelsea recommends experimenting with various sexual positions and ensuring ample lubrication to make intimacy more comfortable (14:03).
• Humorous Relief: She lightens the mood with humor, encouraging Michelle to find a balance between physical needs and emotional connection (16:31 – 16:37).

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Notable Quotes with Timestamps

• Michelle: “I have 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.” (09:21)
• Katherine: “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.” (12:03)
• Chelsea: “Have you tried a lot of different positions and, like, lots and lots and lots of lube?” (14:03)
• Yamanika: “You gotta keep, you know what I'm saying, seeing him around with this nonsense, it's gonna be like, get outta here.” (15:09)

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Insights & Recommendations

1. Open Communication: Maintaining honest and ongoing dialogue about comfort levels and boundaries is crucial.
2. Exploring Alternatives: Trying different sexual positions can help accommodate physical differences and enhance mutual satisfaction.
3. Use of Aids: Incorporating sufficient lubrication can significantly reduce discomfort and facilitate smoother intimacy.
4. Patience and Adaptation: Allowing time for adjustment and being patient with the process can lead to a more harmonious relationship dynamic.
5. Professional Guidance: Consulting a healthcare professional or sex therapist might provide additional strategies and support.

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Conclusion

The episode concludes on a supportive note, reinforcing the importance of empathy, understanding, and mutual effort in overcoming personal and intimate challenges within a relationship. The hosts encourage Michelle to continue exploring solutions and maintain open communication with her partner, emphasizing that with the right approach, physical compatibility issues can be navigated successfully.

Closing Remarks: Chelsea Handler invites listeners to submit their questions for future episodes and promotes the availability of full video episodes on YouTube. The hosts also share updates on their upcoming performances and provide promotional codes for sponsors, maintaining the show's blend of humor, support, and practical advice.

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This detailed summary encapsulates the key discussions, insights, and advice offered in the minisode, providing a comprehensive overview for those who haven't listened to the episode.

Transcript

[Chelsea Handler]

This is an I Heart podcast.

[Katherine]

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[Katherine]

Hi, welcome to a mini episode where these are minisodes. We have a special guest on our minisode. Her name is Yamanika Saunders. Yeah, Hi Katherine. How are you today?

[Chelsea Handler]

Hi Chelsea. Hi Yamanika.

[Katherine]

Hi Yamaneka. Hi Yamanika. Hi.

[Yamanika Saunders]

I adore you guys. This is crazy.

[Katherine]

How Are you.

[Yamanika Saunders]

I'm good.

[Caller (Michelle)]

I'm so good.

[Katherine]

Okay, bye.

[Caller (Michelle)]

Bye.

[Katherine]

Okay, Katherine, what do we got with Yaamaneka today?

[Chelsea Handler]

All right, well, our first thing that we have up is a follow up from a wonderful caller we had, Wit, 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.

[Katherine]

Okay.

[Chelsea Handler]

So I checked in with him and Wit 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. We're 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 gonna 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. 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.

[Katherine]

Wow, that's nice. That's a nice result. Why wouldn't you? Trans. Because her family didn't know that he was trans and she didn't.

[Chelsea Handler]

The partner's family.

[Katherine]

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. Like, they don't need to know that he's trans, but, like, if they wanna tell him that it's not really his. I don't remember what the fuck I said, quite frankly.

[Chelsea Handler]

No, that's exactly what you said. You were like, if you feel you 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 gonna be in, you know, swimsuits, and I will too. And, like, there are scars, you know, different things that he was like, I don't know if I need to explain this ahead of time sort of thing.

[Yamanika Saunders]

Yeah, people be having scars and shit. I got keloids all over the place.

[Katherine]

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[Katherine]

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[Chelsea Handler]

Well, we do have a caller and Yamanika I'm very interested to hear. Well actually both of your advice on this.

[Katherine]

Okay, here we go.

[Chelsea Handler]

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.

[Katherine]

Ouch.

[Chelsea Handler]

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 an 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?

[Katherine]

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?

[Caller (Michelle)]

Yeah, I mean, we've tried it a few times. I mean, I can't even get my hand around it.

[Yamanika Saunders]

Oh, God.

[Katherine]

That's how big it is.

[Caller (Michelle)]

That's too big.

[Chelsea Handler]

It's too much.

[Katherine]

I mean, what's. Hello. What do you have to say, Yamanika? Have you ever experienced a penis that was too big for your Pikachu?

[Yamanika Saunders]

The ways in which my vagina has. Other stories that could be told.

[Katherine]

The way in which your vagina can adapt to a large penis. Is that what you're trying to say?

[Yamanika Saunders]

I have a very tight vagina. Okay. And so a lot of times it's hard for things to get in there, but I also have a competitive go getter spirit. And does he know that? He is too. Like, you've told him this, right?

[Caller (Michelle)]

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 have had one successful session.

[Katherine]

How did that.

[Yamanika Saunders]

Yeah. What was going on there? Do that so.

[Caller (Michelle)]

Well, I. I think it's like a combination. I quit drinking for about a year, just. It just wasn't serving me, but I decided I needed to try drinking again.

[Yamanika Saunders]

Yeah.

[Katherine]

Yeah.

[Yamanika Saunders]

Well, yeah, he got that Hennessy dick.

[Caller (Michelle)]

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 that 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. And I feel like if we keep trying, I'll just adapt more. But it's huge.

[Katherine]

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?

[Caller (Michelle)]

Well, I'm worried, like, if I move on to another person. Not that.

[Katherine]

That's. No, it retracts. It retracts?

[Chelsea Handler]

Yeah, don't worry.

[Katherine]

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's stretched out, you know? Can you close your mouth? Are you getting ready faces? Put that dick in your mouth. Cause it looks like you want a dick in your mouth right now. Is that what you want?

[Yamanika Saunders]

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 gotta keep, you know what I'm saying, Seeing him around with this nonsense, it's gonna be like, get outta here. You know?

[Katherine]

Scram.

[Yamanika Saunders]

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.

[Katherine]

I feel bad for him.

[Caller (Michelle)]

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, the base is wider.

[Katherine]

Oh, God.

[Caller (Michelle)]

Oh, I've never seen anything like it.

[Katherine]

And you're really. Are you really into him?

[Caller (Michelle)]

I really like. Everything else about him is great, and it's so rare for me to find.

[Yamanika Saunders]

Yeah, tell him to eat it first and then see what happens.

[Katherine]

Yeah.

[Yamanika Saunders]

He gotta put. Okay. Yeah. He going to put the work in.

[Katherine]

Yeah. Oh, my God. This is a real dilemma. I wish we knew how to open up your Pikachu more.

[Chelsea Handler]

Well, have you tried a lot of different positions and, like, lots and lots and lots of lube?

[Caller (Michelle)]

Yes, yes, both. And so I think we've ruled out that we cannot do mission.

[Katherine]

It's just.

[Caller (Michelle)]

It goes too deep and, like, from behind is perfect because it can't go in all the way.

[Chelsea Handler]

Yeah. And you can kind of move. So it's not like going as deep sort of thing.

[Yamanika Saunders]

Yeah, yeah, yeah.

[Katherine]

Okay.

[Yamanika Saunders]

You know.

[Katherine]

Well, that's progress. Yeah.

[Yamanika Saunders]

I like that. At a certain age, you like doggy style. You ain't got to look at them. You can do other things.

[Katherine]

You can do your accounting.

[Chelsea Handler]

Go through Instagram.

[Katherine]

Yep.

[Yamanika Saunders]

Yeah, yeah, yeah. Be one hinge looking for another Mockt man with a smaller dick. You know, you could do all this.

[Katherine]

Kind of stuff, but I've got that.

[Caller (Michelle)]

Same go get them attitude. Like I want to.

[Katherine]

Yeah. I mean, I hope. I hope it works out. I wish we had better advice for you.

[Caller (Michelle)]

Well, this. I mean, if anyone has the same problem, called Damiana. Damiana. I feel like. I feel like this is really helping me.

[Katherine]

Okay, so that's to lose. That's to get your juices flowing a little bit more. Like, loosen things up.

[Caller (Michelle)]

Yeah. Because I am at, like a perimenopause age too.

[Katherine]

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?

[Caller (Michelle)]

No, I can't take any hormones.

[Katherine]

Oh, you can't? Mm.

[Chelsea Handler]

Mm.

[Katherine]

So you're supposed to just go through perimenopause with no help?

[Yamanika Saunders]

I don't ever wanna get to the point where dick feel like razor blaze.

[Katherine]

I know, but sometimes that can happen when you go through perimenopause. So she needs all the help she can get.

[Yamanika Saunders]

I'm at perimenopause.

[Katherine]

I know, I know. I'm the one who told, so.

[Yamanika Saunders]

I knew. I was at perimenopause the day before you told me. Okay, well, somebody. You told me second, not first.

[Katherine]

Okay, this is not about you. This is about our caller. And we have been.

[Yamanika Saunders]

She's got an amazing problem. She has the biggest penis.

[Katherine]

You do have a good problem. Okay.

[Yamanika Saunders]

Oh, man, I wish I had it.

[Katherine]

How do you feel for this guy? Because if it's been a problem, before. Like, I know girls who can't deal with big dicks either. Like, 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.

[Caller (Michelle)]

Thanks.

[Chelsea Handler]

Yeah.

[Katherine]

Okay.

[Yamanika Saunders]

Yes. Blessings to y'.

[Katherine]

All. Blessings. Yeah. You need a blessing. Okay. Thank you. Take care.

[Caller (Michelle)]

You too. Bye.

[Katherine]

And that concludes our minisode for today, I think. Right, Katherine? I think we're done with Yamaneika 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?

[Chelsea Handler]

It was open, waiting for the first time.

[Katherine]

She was ready to receive it immediately. You open your mouth. I mean, that's what kind of sick fuck you are.

[Yamanika Saunders]

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. You need to talk to somebody.

[Katherine]

I had a reaction. I didn't open my mouth. That wasn't my reaction. Yeah.

[Yamanika Saunders]

Think about it. It was so much to think about. I couldn't even hold my mouth up. I want to thank you for having me. I appreciate.

[Katherine]

Thank you for coming. Bye. So I added a couple of new dates.

[Vital Proteins]

I'm not on tour yet, but I added a couple of dates just because.

[Katherine]

I felt like we need a little bit more laughter and a little bit.

[Vital Proteins]

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.

[Chelsea Handler]

Do you want advice from Chelsea? Write in to dearchelseapodcastmail.com find full video episodes of Dear Chelsea on YouTube by searching eercelseipod. Dear Chelsea is edited and engineered by Brad Dickert executive producer Kathryn Law. And be sure to check out our [e-mail].

[Katherine]

Listen up. You know what's better than being a jittery mess after your third coffee? Actually functioning like a normal human being. Beyond Brew by Live Conscious is a six in one mushroom blend that won't make you trip balls, but it will give you mental clarity, focus, and less bloating. Forbes called Beyond Brew a deliciously potent coffee alternative and 400,000 people can't be wrong. It comes in cacao, caramel macchiato and vanilla latte because we are not savages. Your mind and body will thank you later. Go to liveconscious.com and use code Chelsea for 15% off.

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Every business has an ambition. PayPal Open is the platform designed to help you grow into yours with business loans so you can expand and access to hundreds of millions of PayPal customers worldwide. And your customers can pay all the ways they want with PayPal, Venmo, pay later and all major cards so you can focus on scaling up when it's time to get growing. There's one platform for all business PayPal open grow today at paypalopen.com loans subject to approval in available locations.

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[Chelsea Handler]

This is an iHeart podcast.