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July 11, 2025 11 mins

A positive update from a favorite trans caller.  Then: A new boyfriend’s nether-regions overwhelm.   

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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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. 

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
Hi, Welcome to a mini episode where these are minisodes.
We have a special guest on our minisode. Her name
is Yamnika Saunders. Hi, Catherine, how are you today?

Speaker 2 (00:09):
Hi?

Speaker 1 (00:09):
Jelsey, Hi, Yamnika, Hi Ya Minika, Hi, Yamnika, Hi.

Speaker 3 (00:15):
I endure you guys.

Speaker 1 (00:20):
Okay, bye, bye? Okay, Catherine, what do we got with Yamnika?

Speaker 2 (00:24):
Say? Well? Our first thing that we have up is
a follow up from a wonderful caller. We had Wit
who called it on our John Lovett episode. He was
wrestling with whether or not to reveal to his longtime
girlfriend's family that he's trans okay, 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.

Speaker 4 (00:45):
We ended up.

Speaker 2 (00:45):
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.

Speaker 4 (01:04):
Yeah.

Speaker 2 (01:04):
Never in the moment, never 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

(01:26):
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.

Speaker 4 (01:45):
Wow, that's nice.

Speaker 1 (01:45):
That's a nice results. Because her family didn't know that
he was trans, and she did.

Speaker 2 (01:51):
Partner's family, Yeah, the partner's family.

Speaker 1 (01:54):
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.

Speaker 4 (02:00):
And I don't even remember.

Speaker 5 (02:01):
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 tranced, but like if
they want to tell them that it's not really his I.

Speaker 4 (02:11):
Don't remember what the fuck I said, quite.

Speaker 2 (02:13):
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 things.

Speaker 3 (02:30):
People we have a scars, the shot got ketoys all
over the place.

Speaker 4 (02:33):
Yeah, well that's a little bit different than being tranced.

Speaker 1 (02:35):
But okay, anyway, anything else, Catherine, Well, we do.

Speaker 4 (02:44):
Have a caller and yaminy guy.

Speaker 2 (02:46):
I'm very interested to hear well actually both of your
advice on this. Okay, 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 POOPSI Whoopsie and Oopsie

(03:08):
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 I'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 light hearted way or a

(03:29):
joking way about how some woman 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.

Speaker 5 (03:44):
For me.

Speaker 2 (03:45):
He's age appropriate, has an education and a good job,
and it's 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.

Speaker 5 (03:56):
Oh god, I've never had a penis that was so
big that it didn't fit, that it didn't hurt.

Speaker 1 (04:02):
So you can't even get it? And are you like
lubricated and ready to rumble?

Speaker 6 (04:06):
Yeah, I mean we've tried it a few times. I
mean I can't even get my hand around it.

Speaker 4 (04:11):
Oh God, that's big, too much? I mean, what's young? Hello?

Speaker 1 (04:16):
What do you have to say, Yaminika? Do you have
ever experienced a penis that was too big for your.

Speaker 3 (04:21):
The ways in which my vagina has other stories that
can be told.

Speaker 1 (04:27):
The way in which your vagina kind of adapt to
a large penis, Is that what you're trying to say.

Speaker 3 (04:32):
I have a very tight vagina, okay, and so a
lot of times 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? Like you've
told him this, right, you know.

Speaker 6 (04:48):
He's like he played it off at first, like it's.

Speaker 4 (04:50):
Not that big.

Speaker 6 (04:51):
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.

Speaker 4 (05:07):
How did yeah, what was going on there? Do that
so well?

Speaker 6 (05:11):
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.

Speaker 3 (05:22):
Yeah yeah, well yeah, he got that Hennessy dick.

Speaker 2 (05:26):
So I had a few drinks.

Speaker 6 (05:27):
I also did some research and I found this herb
called Damiana And basically it's just 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 that this thing

(05:49):
coming at me. And it's still hurt a little bit.
And I feel like if we keep trying, I'll just
adapt more.

Speaker 4 (05:56):
But yeah, it's huge. I leave you.

Speaker 1 (06:00):
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?

Speaker 6 (06:19):
You know, Well, I'm worried like if I move on
to another person, not that that's no.

Speaker 4 (06:25):
It retracts, It retracts. Yeah, it goes back.

Speaker 1 (06:28):
It's like when you have a baby, Your vagina goes back,
you know what I mean, Like it can come and
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.

Speaker 4 (06:40):
It's not like my vagina's stretched out.

Speaker 3 (06:42):
You know.

Speaker 4 (06:43):
Can you close your mouth? Are you getting ready? Face
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.

Speaker 3 (06:52):
I looked at you the second you says something about
your pissy beer stretched out. God bless what it was
going on. Yeah, have to be comfortable with him. It's
you know, and like I agree with everything Chelsea said
after the honeymoon face and you gotta keep you know
what I'm saying. Seeing him around with this nonsense, it's

(07:13):
gonna be like, get out of here, you know, scram
you and your penis got to get out of here.
But I've never had a dick that I There's been
times that I definitely thought maybe I felt them in
my throat, but never dick that like made me tap out.

Speaker 4 (07:28):
I feel bad for him.

Speaker 6 (07:29):
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.

Speaker 4 (07:36):
Oh god, oh, anything like it? And you're really are
you really into him?

Speaker 6 (07:42):
I really like everything else about him is great and
it's so rare for me to find.

Speaker 3 (07:47):
Yeah, tell him to eat it first, and then you
have Yeah, he gotta put okay, Yeah, he going to
put the work in.

Speaker 1 (07:53):
Yeah, my god, this is a real dilemma. I wish
we knew how to open up your Pikachu more.

Speaker 2 (07:58):
Well, have you tried a lot of different positions and
like lots and lots and lots of lube?

Speaker 6 (08:03):
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.

Speaker 2 (08:13):
Yeah, and you can kind of move so it's not
like going as deep sort of thing.

Speaker 4 (08:15):
Yeah, yeah, yeah, okay, you know that's progress.

Speaker 2 (08:19):
Yeah.

Speaker 3 (08:19):
I like that at a certain age, you like doggy style.
You ain't gotta look at them.

Speaker 4 (08:23):
You can do other things. You can do your accounting.

Speaker 3 (08:26):
Yeahs, yep, yeah yeah yeah, b one hinge looking for
another another man with a smaller dick.

Speaker 4 (08:32):
You know, you could do all this kind of stuff.

Speaker 6 (08:35):
But I've got that same go get them attitude like
I want to.

Speaker 5 (08:39):
Yeah, I mean, I hope, I hope it works out.
I wish we had better advice for you.

Speaker 6 (08:44):
Well this, I mean, if anyone has the same problem,
this is called Doniana Domiana. I feel like I feel
like this is really helping me.

Speaker 1 (08:53):
Okay, So that's to loose, that's to get your juices
flowing a little bit more like loosen things up.

Speaker 6 (08:58):
Yeah, because I at like a perimenopause age too.

Speaker 4 (09:02):
Yes, of course.

Speaker 1 (09:03):
And everybody there's a lot of people that can 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?

Speaker 6 (09:11):
No, I can't take any horm moms.

Speaker 4 (09:13):
Oh you can't. So you're supposed to just go through perimenopause.

Speaker 3 (09:17):
No, I don't ever want to get to the point
where Dick feel like.

Speaker 1 (09:21):
I know, but sometimes that can happen when you go
through perimenopause.

Speaker 4 (09:24):
So she needs all the help she can get. I know.

Speaker 2 (09:28):
I know.

Speaker 4 (09:28):
I'm the one who told you you were so I.

Speaker 3 (09:30):
Knew I was at perimenopause the day before you told me. Okay,
somebody you told me second that.

Speaker 1 (09:35):
Okay, this is not about you, this is about our caller,
and we have.

Speaker 4 (09:39):
Got an amazing problem the penis. Do you have a
good problem?

Speaker 1 (09:43):
Okay? I feel for this guy because if it's been
a problem before, like I know girls who can't deal
with Big Dick's either, Like I've heard this story before.
I don't know if it's the same guy, but anyway,
I mean, I wish, I wish you well. I wish
you and I hope that it works out for you guys.
I hope it does. Yeah, Okay, yeah, blessings to y'all.

Speaker 4 (10:06):
Blessings. Yeah, you need a blessing.

Speaker 1 (10:09):
Okay, thank you, Carol, you too, Bye, And that concludes
our minisode for today. I think, right, Catherine, I think
we're done with Yaminika here, she's sitting here. Did you
see her mouth open as soon as this woman described
the dick and the.

Speaker 5 (10:24):
Girth of it. Did you see Yama's mouth just become
a jar.

Speaker 4 (10:29):
It was open waiting.

Speaker 1 (10:31):
For she was ready to receive it immediately you open
your mouth.

Speaker 4 (10:35):
I mean, that's what kind of sick fuck you are.

Speaker 3 (10:37):
If you didn't have any type of reaction to what
she was describing, there's something wrong with you.

Speaker 4 (10:42):
There's a whole lot wrong with you. I had a reaction.
I didn't open my mouth.

Speaker 3 (10:46):
That was I think about it. It was so much
a thinking, but I could even hold my mouth up.

Speaker 4 (10:52):
I want to thank you for having me, Thank you
for coming. Bye. So I added a couple of new dates.

Speaker 5 (10:59):
I'm not on Tori 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 Westhampton Beach August twenty first,
I'm headlining the Rochester Fringe Comedy Festival September thirteenth, and

(11:21):
I will be in NAPA on October third, so those
will be my last dates of the year.

Speaker 4 (11:27):
Do you want advice from Chelsea?

Speaker 2 (11:28):
Right into Dear Chelsea Podcast at gmail dot 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 dot com.
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