Strictly Anonymous Confessions - 1172 - "Olivia" is a Crossdresser who's Wife is Down with him Crossdressing
Episode Date: July 18, 2025Olivia is a crossdresser who has a wife who’s down with his crossdressing. Tune in to hear alll the details including the friend who got him to dress up the first time and how he felt when dressed u...p, how and when he started dressing up at home and where he got his clothes from, how and why he was confused about being into wearing female clothing, down, how he got caught dressing up and how his parents reacted, how he defines himself sexually and his one hook up with a guy off Grindr he has in college and exactly what went down, how and why he told his first gf about how fetish and how she reacted at first and then how her feelings changed over time, how he told his next gf and how she reacted at first, the questions she had for him and how she felt the first time she saw him dressed, how often he dresses up at home now that’s he’s married and she’s down with it, how often he gets to be intimate with his wife while dressed, how he’s still into guys but why he won’t hook up with one and how he keeps the urges down, where he buys his clothing now, how he sometimes wonder if he’d be happier if he was a girl but why he’s still content in his life plus a whole lot more. **To see anonymous a pics of my guests + get TONS of exclusive HOSER and/or CROSSDRESSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at strictlyanonymouspodcast@gmail.com or go to http://www.strictlyanonymouspodcast.com and click on "Be on the Show" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed. Sponsors: https://liferx.md Start your transformation now and get $50 OFF your first month, use code: ANONYMOUS https://beducate.me/pd2520-anonymous Use code: ANONYMOUS to get 50% off your yearly pass plus get a 14-day money-back guarantee https://vb.health To get 10% off Drive AND LOAD Boost by VB Health use code: STRICTLY Follow me! Instagram https://www.instagram.com/strictanonymous/ Twitter https://twitter.com/strictanonymous?lang=en Website: http://www.strictlyanonymouspodcast.com/ Everything else https://linktr.ee/Strictlyanonymouspodcas Learn more about your ad choices. Visit megaphone.fm/adchoices
Transcript
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So if you have a naughty, interesting secret life that you want to talk about while remaining anonymous,
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Okay, today I'm on. Okay, today I have on Olivia. I love Olivia's story. Olivia is young.
Olivia is only 27.
Olivia is a guy who's a cross-dresser.
He's currently married.
His wife is accepting of his cross-dressing.
And he tells me the whole story of how he wound up there, right?
Of course, we go all the way back to the first time he dressed, which is a very interesting story of the first time it was sort of presented to him.
And then he talks about, you know, what he did when he was younger and then how he dressed up more as when he got older.
He did have one hookup with a guy while he was just.
dressed. He talks about that. That's a very interesting story that happened when he was in college. He
talks about the specifics and how that came to be. He also talks about how he felt about his sexuality
after that experience. He talks a lot about, you know, how he feels about his cross-dressing and what
it means for him. He still has some questions. We go over those questions that he still has for himself now,
even at 27 with a wife who accepts it. He still has some questions about himself and how he feels.
We talk about that. But we also talk a lot about how he brought it up to his.
wife. It wasn't the first woman he brought it up to. He brought it up to somebody before her. He talks
about those conversations and what happened with the first girl. And then you know how his wife handled it
when he told her in the beginning. And then how his cross-dressing plays out like within their
marriage. It's a super interesting episode. I love his take on things. I think he's a super
honest upfront, clear-headed guy for 27. That's like pretty great. I think you're going to love a
story. I think it gives people hope that there are women out there who will accept this kind of fetish
because, you know, he got married and his girl was okay with it. And I think that that's good
for other cross-dressers to know, okay, for the ones who are living a secret life. He's not, and he
doesn't have to because he was honest and his girl was accepting. So it's a super interesting story.
Like I said, I think it could give some people hope. So I'm going to get right to it and be right back on
with Olivia. Hi, Olivia. Welcome to the strictly anonymous podcast. How
are you today?
Good.
How are you?
I'm good.
So you're Olivia, quote, unquote.
We can tell by your voice.
I will make your voice higher.
That's what I do for my cross-jester.
Olivia, you're a cross-jasser.
You're a cross-jester and you're calling in to tell your story.
I mean, listen, I could talk to a million cross-dressers.
And I have.
I've talked to hundreds of cross-jesterers, you know, and every story is always a little
bit different.
And so, you know, I typically like to start off nowadays, like getting a snapshot of where
you're at now and then we'll go all the way back. Like, are you a married guy? Are you single?
Like, what's your deal? Yes, I'm married. I've been married for about three years.
And my wife knows about my cross-dressing. Oh, I like that. Okay. Yeah. So it was something that I told her
very early on in our relationship, but I didn't want to keep it from her. Yeah, we'll get to that point
where you meet your wife and you explain everything to her. But I love that you're literally, you say,
kind of youngish. Like, how old are you, Olivia?
I'm 27. Okay, yeah, you sound super young. How long you've been married to your wife for?
We've been married about three years. Oh, okay, great. So, and how long you've been together?
Like, how old were you when you met her?
Together, about five years. Wow, okay, so super young. I find the younger generation,
you know, are so much more open about things, you know? So, and that works in your favor, you know,
because these poor guys, I'm sure that you've heard them on my show, you know, living a double life their whole fucking life and never being able to admit it.
You know, it must be so great to be living with someone who knows and accepts it, you know.
But let's go all the way back, Olivia, and talk about, like, your first memories and when you started to realize that you might be into cross-dressing.
Yeah.
So time that I really remember, you know, being, you know, being interested in the idea of cross-dressing was way back when I was about eight, nine years old.
And I was having a sleepover with a friend of mine.
And on the middle of the night, he, like, woke me up.
And he told me that he wanted to kind of play dress up and pretend that we were, like,
boyfriend and girlfriend and just do some stuff because he was curious about it.
And me being nine years old, and I didn't really think much of it, know what was happening, really.
but he wanted to dress me up.
Wow.
I mean, because I have a nine-year-old, so I think to myself, like, because that going on in
my son's room and they're hanging out in there, you know what I mean?
Oh, my God.
Right.
I don't think anyone would have ever pictured that.
Yeah.
I mean, he was like two years older than me, but.
Oh, okay.
But, yeah, still.
Yeah, but when you're younger, those years, there's a much, there's like a big difference
between a nine-year-old and 11-year-old.
you know. And listen, these kinds of things do go on, I think, sometimes secretly. Kids are curious. Sometimes
they don't even really understand what they're doing. So he wakes you up and like, let's dress up and what went.
Now, before that, though, had you had any kind of inklings or like any kind of anything in your mind that told you that you were into this before he brought it up?
I mean, a little bit. I was definitely fascinated by women's clothing. I didn't really, again, I didn't think too much of it.
I was young, so I just thought that it was nice, but I was told that I was a boy's clothes
were for boys and girls' clothes for girls, and so for me that was pretty easy to, you know,
and like, okay, that's the way it's supposed to be.
Yeah, of course.
So, you know, when this happened the first time, I opened my eyes up to like, okay,
this is something that I want to do as well.
Oh, okay.
So, and what did you guys do that night?
So he has a sister, so he went into the basement.
and he got like one of her like princess costume something and brought it up and had me put that on
and really we just like we kissed a little bit the kiss kind of like the way nine year olds would
kiss which was probably just like pecks and whatnot and then just like a little bit of touching
and that was kind of it but it was it was while I was dressed up that way right okay so and how
did you feel like being dressed up I just remember love
It was like, it just, it's like so hard to explain the exact feeling, but it just felt like something that I had been missing in my nine years of life, even though I wasn't a lot, but it just, it felt like so.
Comfortable?
So it felt like it, like, it fit me.
It felt like it was comfortable.
It felt like it was right for me, and I was just very excited by it all.
That's interesting, right?
Were you surprised by that for yourself, or were you not even old enough to like think that for?
Yeah.
I mean, I definitely remember being surprised.
by how much I enjoyed it, but I also in the back of my head was like, okay, this does make
sense a little bit.
Right.
Interesting.
Okay.
So now that friend, did you guys ever do that again?
So we did it like two, three more times.
I only ended up seeing him a couple times over the next couple of years.
So the time period spread out a couple of times, but it happened about three, four times.
Wow.
Now, did you ever go any further than the kiss?
there was some touching again we were just young curious yeah so there was like touching obviously in some
more private areas but nothing really more than that because again not a lot of knowledge as to what
they would even be to do other than what we were doing yeah exactly I mean he might have had the
knowledge I mean he was 11 that's a little bit like that's like a middle school compared to like
preschool kind of thing you know what I mean I don't know I can't explain it because I do have a son but still
Okay, so, all right, so now after those experience, it kind of maybe triggered something in you,
and then where did you take that, what happened next?
Not a lot of knowing.
Yeah, exactly.
I mean, he might have had the knowledge.
I mean, he was 11.
That's a little bit, like, that's like a middle school compared to like preschool kind of thing.
You know what I mean?
I don't know.
I can't explain it because I do have a son, but still.
Okay, so, all right, so now after those experience, it kind of maybe triggered something in you.
And then where did you take that, what happened next?
So from that point on, I just, I mean, I have an older sister and, you know, my mom was in my house.
So I just started as often as I could.
It really started with, you know, not feeling like I'd be able to go into their rooms and steal their stuff.
That was all too big and scary for me.
But my sister was also a couple years older than me.
So she also had all of these Disney princess costumes, all these other types of costumes.
So I would spend a lot of time in my basement trying those on and just playing around and
those and really enjoying that.
Now, did you ever get caught dressing up like that at all, ever?
I did get caught, but later on.
Oh, okay.
So let's stick now.
You're still young and you're like using your sisters like costumes and stuff.
But that must have been fun because that's like really girly stuff, right?
like princess something.
Right. Yeah. It was really just like an innocent, plain dress up, feeling girly type thing and nothing really more than that.
It was just something that I enjoyed. Right. But you knew even at that young age that this was something you can't tell anyone that this should be a secret, right?
Correct. Yeah. And is that confusing for you at that time?
For sure. I mean, you know, when you're told from, you know, as young as you can remember that, you're supposed to dress a certain way and then you dress a certain way and then you dress it.
different way from one time kind of by accident because someone told you to and all of a sudden
it feels amazing. You get very confused about why that is and you know you were told differently
and what that means and are they wrong? Are you wrong? And it's definitely very confusing.
Yeah. And what went through your head? Like how did you like come to terms with it? Like did you wonder
if you were gay? Did you wonder if you were trans? Did you wonder, you know, like did you, did you
wondered other things that I'm not thinking of.
Right.
I mean, it definitely, the thoughts changed over time.
I think when I was very young, it was kind of like, oh, I wish I were a girl because
then I can dress this way all the time.
Right.
And I didn't think that I was gay because, you know, I had a bunch of friends and I
wasn't really attracted to them and I was too young to kind of be attracted to anyone, but
I knew that the girls were the people you were supposed to kind of be attracted to.
So I didn't really think about that too much, but it was more like the
oh, if I were a girl, then I'd be able to dress this way all the time.
Yeah. And like I wonder, do you feel like now that you're older and you're allowed to do it and stuff?
Do you feel like you're comfortable and happy with it being something that you do every now and then,
as opposed to needing and wanting to dress all the time?
So it depends. I mean, obviously it's something that I would prefer to do at all times if I could.
Oh, really?
Yeah, I think going through this as long as I have, I've kind of,
come to terms of the fact that that's not going to be in my reality. So I've been able to get
as much out of it as I feel like I can. And luckily, I have a wife who supports it. So I'm able to
kind of do it around the house with her. But, but yeah, I mean, I definitely wish that I could
do it more often and freely and not have to hide it. Now, do you feel like, because there's a
difference between a cross-dresser and being transgender. Do you ever feel like you're born in the
wrong body or maybe you wish you were a girl is one thing about wanting to just wear the girl's
clothing but do you ever have thoughts of like you wish you were a girl or you feel like maybe you were
supposed to be a girl did you ever have those kinds of thoughts yeah definitely had those thoughts over
the years and come come and gone and and it gets intertwined with you know like you said just in the clothes
because obviously if you're a girl then you can wear those clothes all the time so that part of it is
definitely part of it, but then there definitely been times where I thought to myself really,
maybe it really is just the close and I'm happy being a guy, but it definitely goes back and forth.
Yeah, it's interesting. And I ask those questions because I think there's like this big
conversation going on now about trans kids transitioning really young, right? And, you know,
so I think it's always interesting to see, like, how do you feel when you were younger and then
when you felt so much, when you were older? Because I think it takes a long time to figure
yourself out regardless of what the fuck you are, right? So,
I think it's like I got a tattoo when I was 17 and I would have never fucking done that if I was like 32. You know what I mean? Like I should hide and I wish I didn't get it because I hate it. So I just think like a lot of times we're just trying to figure ourselves out and it takes a while to really figure it out. So I always think that's an interesting kind of discussion. So okay, so you're dressing up and stuff and now in your middle school, but you know at this point that you like girls. Do you ever, are you like how do you define yourself sexually now? Are you a heterosexual?
Are you fluid?
Like, what's your deal?
So now I would say that I'm fluid.
I mean, I'm married, so, you know, it's only my wife, and I don't get on her or anything
like that.
So my general sexuality, I would say that I'm fluid, but in terms of how I act on that,
it's a heterosexual relationship with my wife, and that's it.
Right.
Okay.
But did you have experiences with guys before her?
So other than the experience when I was younger, I had one other experience when I was in college with a guy.
Now, were you dressed during that experience or were you like a guy with a guy or were you Olivia with a guy?
No, I was dressed.
Oh, okay.
And how did that happen?
I mean, I'm kind of jumping, but I'll go back to when you're nine and take it from there.
But like, how do you wind up in college dressed as a chick hooking up with a guy?
So basically when I was in college, I had this one friend who I got really close with and I hadn't told anyone about my cross-dressing and her and I really got close and I decided that she was someone that I felt like I can trust and talk to about it.
And so I told her and she was great about it and she was someone I was able to rely on.
And she asked me if I was gay, if I was straight and I told her that I wasn't sure and I had this experience that I didn't know.
and she told me that I should just try,
try and hook up with a guy and see what that would feel like.
And so I ended up getting on Grindr and was able to connect with some other random guy that was in my college.
And I told him that I was a cross-dresser.
And he said that he was into that.
And we were, I wanted to make sure he wasn't like a creep.
So it took a while until I kind of.
trusted that, you know, it would be okay if we got together.
And we ended up getting together.
And when I got there, he let me go into the bathroom and change into some girly clothing.
And we hooked up.
And it was great.
Now, listen, an experience like that definitely, I think a lot of times, helps you figure
out whether you are into guys if you were wondering, right?
Because, like, you didn't know, right?
Like you even said to that girl, I had this experience.
I don't really know.
So you tried it out.
How did you feel afterwards?
So afterwards, I mean, I felt great because it was a great experience.
It definitely left me feeling a certain part less confused,
and it was a certain part more confused because like, okay, you know, I enjoyed that.
But do I want to date a guy?
Not an out cross-dresser who's just going to be doing that all the time.
And I don't really want to be a guy who's with a guy.
So, you know, what does that mean for me in terms of relationships or hooking up or whatnot?
And so I said to myself, like, if I end up in another position,
a situation where I can hook up the guy dressed like a girl, then great. And if not, then not.
And I ended up not really standing with anyone else. And I ended up meeting my wife. And so,
and so I just didn't have another opportunity. Yeah, it's interesting. Because a lot of times,
most cross-stresses who hook up with guys, they really only do it when they're dressed. So it is
kind of like, it gives you so much more to think about. You know, it's not really like, oh, you're
wondering if you're into the same sex and then you're with them. You know, there's a lot of other layers, right?
like you said, it kind of like added more questions because you did have a good time, right?
Like you enjoyed yourself.
Yeah.
Yeah.
Yeah.
It was a great time.
It just like, yeah, it just kind of goes both ways.
Yeah, yeah, totally.
And so that happened.
That girl, like, did she like ask you about your experience?
Was she like, you know, because she kind of like helped you up and helped you out, you know, your friend.
I know if I was your friend, I'd be like, what the fuck happened?
Tell me everything, you know.
No, I, like right away called her.
and I got together and I spoke to her about it.
And she was getting very supportive.
And yeah, it was great to have her to kind of help me, you know, through the process.
Yeah.
Now, before her, though, because, like, we're still, like, in grade school and you're trying
things on and everything.
I'm assuming, you know, before that, is this just like a secret thing that you're doing?
Did you share it with anyone else before her?
Right.
So, you know, going back to when I was much younger, you know, it kind of, you know, the older I
got sort of started to advance from like just costumes to going into my sister's room and taking
her underwear and her bras and her clothing and stuff like that and then really starting to experiment
with that stuff right and for a while it really was a secret and I took it very seriously and made sure
that no one saw me and after but after a certain amount of time you know you start to get comfortable
and you start to feel like you do a good job hiding it and so and but also like that urge to be able
to dress more often grows yeah and so one day I decided to like take a risk and and and put
some clothes under my school clothes and see like I can get away with that.
That's naughty.
You know, no one will notice.
It'll feel good.
Yeah, it'll be naughty.
You'll be a good feeling.
And as I'm changing in my room in the morning, early in the morning when no one ever comes
into my room, my mom walked in and she saw me.
Oh, my God.
What were you wearing?
Because, I mean, as a mom, I'm thinking, like, what, you know, I'm putting myself
in your mom's position.
Like, I'm painting the picture.
Like, what the fuck is her son wearing when she opens the door?
Right.
So at the time, I was like time for her to walk in because there was only one second.
I was really exposed this way, but I was wearing much as there's underwear.
I was wearing one of her, like, for all lets that don't have any panning, said it was like flat.
And she walked in and she saw me in that moment.
And she like immediately like said like, like, whoop and like close the door and walked out.
Right.
Yeah.
Okay.
So did she ever talk to you about it?
Did she just sweep it under the rug?
Never made a comment about it again.
And like what happened after that?
Right.
So she actually, you know, she walked out.
I took the clothes off, went to school.
And then that day when I got home, she came in terms to try to talk to me about it.
But I was around 14 years old.
That was like horrified by the whole situation.
I didn't really want to speak to her about it.
Yeah.
So what was she?
Like what did she want to talk to?
Like what was she trying to say?
Like was she just like asking you like, when did this start?
Like what were her like what was the conversation?
She was trying to start up.
Right.
It was more of it like, you know, trying to understand why I was doing this, what, you know,
where all this was coming from.
It wasn't an angry conversation.
It was more like just trying to understand.
But again, I wasn't saying anything because I was so petrified by what happened.
I just wasn't ready to speak to her about it.
So I'm not to stay silent.
But those were the general question she was asking.
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description, click on the link, and use my code anonymous. Right. It was more of it like, you know,
trying to understand why I was doing this, what, you know, where all this was coming from. It wasn't
an angry conversation. It was more like just trying to understand. But again, I wasn't saying
anything because I was so petrified by what happened. And I just wasn't ready to speak to her about it.
so I kind of stayed silent, but those were the general question she was asking.
But I love the fact that she wasn't shaming you.
She didn't make you feel bad about anything.
She was trying to understand it.
And it makes sense that at your age, you know, that's the last thing you want to
fucking talk about, you know, but I love that she weighed.
I love that she didn't flip out at that moment.
I love that she didn't make you feel bad about it.
I love that she gave you a beat to think, you know what I mean, to go to school,
come home.
She tried to have the conversation with you.
It didn't work, but like I said, I like the fact that she didn't make you feel bad, you know, because those kind of moments could really change the game.
You know, if she made you feel really horrified and terrible about what you did because she flipped out about it.
You know, that could really set you up in a totally different way.
Right.
I mean, it's funny because she did react that way at the beginning, which is very nice.
But then, you know, she ended up speaking to my father about it.
And my father's a lot more,
and parents a lot more traditional.
So as a couple, as a group,
which I'm sure was led by my father,
it was really,
okay, we need to kind of fix you.
This isn't good.
You're doing something bad.
We got to fix you.
So they tried to send me to a therapist
and try and get that worked out and whatnot,
which sending 14-year-olds to therapy against their will
usually doesn't, you know.
Yeah, and also, I'm sorry, but like,
would the, like, I don't think the therapist would be like,
you need fixing. I'm sorry.
Like most therapists would understand that like there's no fixing this.
Do you know what I mean?
Like did you ever watch Sopranos that time where they sent their daughter to like some hippie therapist?
And she just like sort of went with it.
Like I mean no therapist is going to be like, oh, we're going to this is going to fucking go away.
You know what I mean?
Like it's funny that they sent you to a therapist.
The therapist would disagree with everything that they thought they were sending you there for.
You know what I mean?
At least any normal therapist.
Yeah.
It was really just a weird experience.
kind of took from that that I had to like really convince them that it worked and they fixed me
and it's all behind me and so I spent a long time getting really, really good at hiding it and really
making sure that they would have no idea that that was still going on. Right. Because in their
mind, they just thought that this could be fixed. You can't do this anymore. Like this has to stop
and a story. Yeah. Yeah. Okay. Okay. So I mean, your dad must have been fucking horrified. I think
it is a very big difference between the guy and the, you know, like that she told your
dad she had you know of course he was going to be the one i think that would flip out more yeah definitely
did your dad change the way he treated you after that or did it seem to just like blow over and they
never caught you again and it was business as usual i mean at first he seemed to like have more of an
eye on me you know not really want to let me have some time alone because he thought that i was doing that
and he didn't want that in his house and then slowly over time when he felt like it really had passed
and it was just a phase and whatnot.
He kind of left it alone and everything went back to the way it was before.
He must have been so happy the day you got married to a girl.
Yeah.
You know what I'm saying?
Yeah, and to the day it's exactly what he dreamed for.
Yeah, so everyone's happy.
Okay, so that's the time you found out.
And now, so you obviously were better at hiding it moving forward, never got caught again?
Correct.
Right.
Yeah.
Okay, so what happened when you started dating girls?
So throughout like high school, I mean, I dated girls and I didn't tell any of them about it.
Really in my head it was like something that I can never say to anyone because no one would ever accept it and they think I'm weird.
And if I want to function in the world, I need to be able to just hide it.
So throughout high school, I just kind of like kept it to myself and I dated girls and they were short-lived and we broke up for a bunch of different reasons.
But that never came up.
And then before I met my wife, I dated this girl for a while.
and when it felt like it was fairly serious and like we really were like super, super intense,
I felt like, okay, if she could potentially be my person,
so someone that I really think that I need to tell her about this,
because that could be something I would be able to hide from her forever.
And so I told her about it.
And at first, she was like comforting because I told her a vulnerable thing.
But over the next couple of weeks and months,
she kind of made it very clear that it was something that made her really uncomfortable
and she didn't want around her and she didn't want me to talk about.
and she didn't want to know about.
And that just made it very hard for us to like continue in our relationship and we ended
breaking up.
Wow.
Okay.
So that, what I'm thinking that's like your girl now.
Okay.
So that was the first girl that you told.
And listen, you know what?
What's great about that story is everyone was truthful, right?
She was truthful.
Like, I can't deal with this.
You were truthful.
And you guys separated it as you should, right?
That's, that was, you guys were not right for each other.
So that's the way they say, you know, like weed out the trash.
Right.
Just be honest.
someone's not into it.
That's like that was, I think, a great thing that you did.
And it obviously didn't deter you from doing it in the future because you told this wife.
I mean, did it deter you for a while of telling girls or did you continue to be honest?
It definitely made it scary.
My wife was the next person I ended up dating.
But in my head, there was no way I'd be able to marry someone and live with someone without them knowing about this because it was a big part of my life.
So it made it scarier, but I knew I was going to tell them regardless.
Yeah, it's interesting because so many people feel like they could keep it on the DL,
even though it is a part of their life.
You know, it's interesting that you saw it that way because that is the right way.
Like, you know what I mean?
It's hard to keep that whole thing because the fetishes are very powerful, right?
And they're such a part of who somebody is.
So to keep that kind of hidden is very difficult, I think.
But so many people don't think like you do.
They don't think like, oh, I can't keep this.
hidden, I have to tell.
I could, you know, they think, oh, I'm fucking keeping this hidden because I would never tell
anyone, you know?
But for some reason, like, you just, you didn't think that.
I think that that's great.
Well, I think also for those people, it's something that they feel like they have to
keep hidden no matter what.
And because of that, it makes, well, it makes the dressing a lot less enjoyable
because it's very stress-filled because you're wondering when is this person going to come
back or how intensely do I need to hide it or is my stuff hidden enough.
And I make it just a lot of hard.
harder. And so for me, it was something that like when I was hiding it, if I ever got time alone
to be able to dress, then I would. And then I'd have to hide it to make sure I hit it perfectly.
And there was no chance that anyone could find me. And it was a lot of like steps. And it felt like
it was too much for me. And I wanted to be able to really do it more often. And so that made it
clear in my head that if I was going to be with someone that I'd have to tell them about it,
because I needed to have a bit more of that freedom. Yeah, I love that. And let me just tell you,
there is that other person and I've heard from them and it's kind of the opposite of what you just said
in that a part of their sort of kick of doing it and the turn on is that nobody knows and that it's a
secret. I had someone call in recently who was a cross-dresser and said, you know, when they did
cop to it and they were out and proud, it did take away a little bit of the funness or hotness
about it because it wasn't like this secret thing anymore. But I think those people get wired into that
by keeping it a secret for so long.
You know what I mean?
You were kind of like, I think it pretty open about it, you know, early on, like you told
that friend in college and stuff that, you know, I don't think you wired yourself into,
like having this be this naughty hot thing, which I think sometimes people do frame it that way.
And then, like I said, there's people who will be very honest and cop to the fact that, like,
you know, a part of the turn on is that it's a secret.
Right. I agree. I mean, I understand the idea of things being a secret, you know, a turn-on and that being enjoyable. I get that. And that's definitely a part of it for me. It's just that there's a line between the excitingness of it being a secret and then it being such a secret that you really don't get to enjoy it as often as you would have liked to.
Yeah, listen, I think it's exhausting living a double life. It's exhausting living one true life. You know what I mean? Like add us another one to it. It's too much, you know? I think you're smart. I mean, like I said, I think it's great that you are just wired the way that you are. So, all right, so you meet the next girl and you're like obviously afraid to tell her because you just got dumped by a girl because of it, but you decide to tell her anyway. Like how early on into that relationship did you cop to it?
So, I mean, I dated the previous girlfriend for about a year and a half before I told her.
And so when I found out that she really just was against it and ruined our whole relationship,
it felt like I had wasted a good year and a half of my life.
And I really didn't want to do that again.
So in my head, it was like if things feel like they have a potential,
but I haven't, it hasn't been too much time, then, you know, I just need to do it and tell her.
And if it's not for her, then we'll go our separate ways.
and if it is then great.
But if it's not, at least I won't feel like I wasted so much time.
So after about two months, I told her, and we kind of took it from there.
So tell me that exact conversation in what she sat.
So I sat her down and just said, got to talk, and she was obviously worried about
something terrible.
It's just something I need to tell you about myself.
And I said for about as long as I can remember, I've been dressing in women's clothing
and I've been doing any secret, and it doesn't really change any.
about my personality or anything you know about me other than other than that.
It doesn't mean that tomorrow when you see me I'm going to act any differently or be any
differently.
It just means that this is something that I like.
And I basically said to her, like, I'm telling you this now because I don't want you
feel like you have to stay with me because of this.
And I also don't want it to be too deep in our relationship where you feel like I betrayed
you by hiding this from you.
And kind of like my previous girlfriend, she was very supportive right away because I was
being vulnerable or volunteering or something, but then she followed up with that by continuing
to be supportive and curious and accepting.
Right, as opposed to the other one that over time started to realize like she can't deal
of it.
This one just kept continued being supportive.
Now, did she have a lot?
Like, what were her questions?
I would assume like she had questions when you told her.
And what were those?
Right.
So her questions were, first she asked the classics, does this mean you want to be a girl?
Does this mean that you're gay?
Does this mean that you are going to start dressing in public?
Those type of questions.
Does anyone else know?
And, you know, I told her that I wasn't gay.
I told her that, you know, I've had some experiences just because I was curious.
And she didn't really think too much of that because I told her that I was attracted to women.
And, you know, I'm faithful to her.
So she didn't really care, you know, what else is going on.
and yeah and I told her that I thought that definitely when I was younger I had thoughts of
what gender I thought I should have been and that it's still something that can randomly
pop into my head but it's not something that you know that she should worry about and and yeah and
that was she was kind of okay with that and I'm sure that it was something that took her a while
to really get her head wrapped around but we're in a good place right now yeah that's amazing so
you told her very early on to me that's early on and now did you
start to dress in front of her?
Like, how did you move forward after, you know, she knew and she was accepting, like, how
was it set up between you guys?
Right.
So it took a, it took a good amount of time at the beginning.
It was something that we didn't really talk about that often, but you knew about.
I don't know if I didn't know.
If I was ready to really be speaking about normally.
Yeah.
And then after a couple of months, I showed her the clothes that I had.
And then that progressed to, like, me telling her.
when I was dressed when she wasn't around, that she knew,
so that she didn't feel like it was like something I was hiding from her.
And then after a certain amount of time,
she led me dressed in front of her.
And we kind of took that slowly to a point where now it's something that I can,
you know, do normally.
And so when you were dressed in front of her, like,
let's go through like that first time.
Was it going to be an intimate moment?
Was it just going to be something where you dressed up and showed her,
like how you look?
Like, how did that go down?
Yeah.
Yeah.
So it was really just going to be something where I showed her and we'd kind of like hang out.
Just like as I was now on a random man watching movie as if it was just a normal night but me dressed that way kind of for us to get comfortable.
But without it being too intense and too serious, we didn't want to like jump into anything too crazy right away.
So it was really just that just kind of like, here, this has me dressed this way.
You can react however you want because it's awkward and it's new and it's different.
And we'll just like take it day by day.
Okay.
So how do you like to dress when you dress up?
And like how hardcore are you?
Are you like full outfit, had to toe, shoes, everything?
Do you do makeup?
Like, what do you typically like to dress up in too?
So because I like really wanted to get good with like keeping it a secret, I, I never really did makeup.
I always felt that that was something that you can get caught with.
It's too time consuming.
And for someone who like needed to be in and out, I never really.
really got into that.
I tried a couple of times, but that's really when I had just a lot of time, you know, at hand.
And I just never really became something that I really jumped on to.
But everything else I would pretty much wear.
I mean, normally I would dress inside the house, so I also didn't really wear heels.
I'm also, I have a big, I'm a size 13 males.
Oh, my God.
Yeah, they don't make it.
So, you know, wearing heels?
Do you have like a stash of clothes?
Were you borrowing hers?
Like at this point, by the time you're like dressing up in front of her, because I didn't
really ask you over all this time, were you buying on Amazon or going out and getting
your own stuff?
Like after you stole from your sister, like when you were older, like, where did you get your
clothes from?
Right.
So at the beginning, I went into a couple of those random Walmart, you know, even like
CVS's Walgreens.
places like that and would just grab whatever dresses, bras, underwear that I can find,
regardless of whether I knew they fit me or not, and would just buy them with a bunch of other
stuff so that it seemed like it was a whole random purchase.
And then over time, I started ordering online and kind of developed my own stash.
So now I have like a nicely sized stash of clothing.
What's your vibe when you dress up?
Like, what kind of girl are you?
very like very like proper feminine you know I'm always wearing a dress it's always very flowy and
vibrant colors so that's kind of what I connect to that's like they try to address that way
yeah everyone has a certain certain style for sure some like slutty some like conservative some like
the business look you like very feminine right yeah I've always for me it was like if I have the
opportunity to dress I always want to make it as
feminine as I can. Right. Okay. So how did your girl react the first time she saw you? What did she say?
Like, you know, it was she obviously like, you know, she didn't know how to like what facial reaction to make because, you know, it was weird and funny and different. And also like I, I also have like breast forms and wear it with a bra. So she's like seeing her husband with boobs.
Yeah. Is she into women at all?
I'm sorry?
Is she into women at all?
She's not.
Okay, so it's not like, because listen, some women may be like, you know, if they're a little by themselves, maybe they, you know, don't mind that.
So no, she's not.
Yeah.
Right.
So it was definitely a weird, weird experience for her to see that.
But again, she wasn't angry about it.
It was more just a new experience and it took time for her to really get comfortable with it.
Right.
And I mean, at this point now, you've been with her for a while and she knows, is it like just no big deal? Do you just like walk around dress? Like, how is your life now? I still have so many more questions, but like nowadays, because you've been out and proud with her and everything and you guys live together. You're married, you know, how, what's your typical week like with dressing up? And do you do it intimately? Like, do you dress up when you're having sex and stuff like that?
So now, I mean, I work from home. So I really am dressed most days when I'm home.
and I don't tell her it's just the way that I'm dressed and she knows about it and it's cool and it's fine and it's all good and outside I dress like a guy regularly sometimes I'll have panties on under my clothing when I'm outside but normally I'm just dressed inside and then dressed regularly outside and then as far as you know our sex life it's something that we've tried a couple of times it's something that she's a little bit less comfortable with having in the bedroom which I I I
understand because it's not something you can kind of force on someone. Yeah. So we, we, we rotate. It kind of
depends on the mood. Sometimes it'll be spontaneous and I'll be dressed anyway and we'll just kind of
roll with it and and sometimes we'll plan to have a night and, and I'll go back to being dressed
like a guy and that's just the way we do it. Right. So there's, it sounds like a really great
compromise. Like she'll do it for you and you'll not do it all the time for her and you're both
okay with that. Yeah. Yeah. It's something that we need to compromise on and neither of us are mad at the
other one and we both understand why the other person feels the way that they do and we kind of can't,
can't force the other person to feel the way that we do. So we compromise. Yeah, well, listen,
you both sound very reasonable because that's the way it should be and that's like,
realistically, that's what probably typically is going to be the setup if everyone's going to be happy,
right? Like it's not like a lot of women are going to want you to be dressed as much as you want to be
dressed, right? And vice versa. So it's like somewhere in the middle, everybody gets a little bit of
what they want, right? What do they say? Like the best negotiation is when like everybody walks
away without everything that they want, right? Like that's the good negotiation. It's not like
because if someone gets everything they want, then the other person's getting nothing that they want, right? So it's
like you're both getting a little bit of something. It's a middle ground for sure. Yeah.
Yeah, definitely.
Yeah, totally.
So she's cool with it.
Now, do anyone else know, like, does she ever tell any of her friends, or is this, like,
your big secret?
So it is my big secret.
I haven't told anyone else.
I did tell her that, knowing, you know, I understand how hard it can be to have a secret
like this and have it dropped on you.
And the only person that you're able to speak about it is the person that told you.
And so I told her that, you know, she felt like she really needed to speak to someone about
it that wasn't me just to like it.
too to release some of that, you know, angst and sad of her that she could. She still hasn't,
but if she wanted to, and it was someone that we both trusted and felt like we can trust
with them keeping that secret that she could. But for now, it's just the two of us then, though.
Right. So now, do you ever dress up when you go out underneath your clothes?
Like with underdarmments and stuff? Yeah. So I, I, it's been on the situation, obviously,
because I'm always trying to be careful, but I'll wear panties under my clothes a lot,
and I'll wear, like, brolets under my shirt.
It's cold out, and I can wear a jacket.
It'll be a situation where no one would have any reason to notice it.
So I do that from time to time.
Right.
And now, like, because you had that one experience with the guy dressed up,
and you are a faithful guy and you're with your girl now, like, do you, like, do you ever have
urges to be with a guy again?
and do you just like jerk off and think about it and it's done with?
Or do you feel like eventually at some point you might want to do that again?
Or do you feel like you'd be totally satisfied and never living that out in real life?
Because you are with your wife?
So, I mean, I haven't been married for that long,
but I feel like everyone kind of gets to that point where they love their spouse so much
and they would never want to lose them or be with anyone else.
But at the same time, they're humans and they can get excited by the idea of
if they find someone attracted that they'd want to be with them also.
So the idea of having another experience where I'd be dressed and kind of playing the female role with the guy has definitely been in my head.
And I've gotten excited about it, but it's never even crossed the realm of possibility for me to do because I would never cheat on my way.
So it's like you said, you know, go on porn sets and watch a bunch of those random cross-dresser porn videos and jerk off to that.
And then, you know.
And then you're done, right?
And then I'm done.
And you still have your relationship intact, you know?
Correct.
Yeah.
Yeah.
I mean, listen, I think that that's the smart way to be, you know.
And so do you continue?
Do you go into stores?
Did you say that you do go into stores and buy your clothes yourself?
And how do you, like, you know, do you feel embarrassed or I guess you don't care when you're going into a store and buying women's clothes?
And you just pretend you're buying for your girlfriend?
So I've done that a couple of times.
It's been a little hard.
I'm a big, tall guy.
I'm 6'2 on the larger side.
So to go in and try and tell someone that I'm buying stuff for my wife,
who's the same size as me, they, you know, that's not really too, that's not too believable.
They're like there's no girl as big as you.
Yeah, but I have, I've been on some business trips,
and when I'm in random areas, I'll find, like, you know, like one of those sex shops,
and I'll go in there and they have lingerie there.
And normally people, you know, the workers at sex shops are fairly open minds and they're not there to judge.
So if I'm in those situations, then, you know, I can be honest with them and tell them that I'm shopping for myself and they'll help me out and I'll even try stuff on when I'm there.
So those situations I've shard out a couple times.
And the great thing about your life is, is if like you buy that and when you're on a business trip, you could come home and you throw that in your closet, right?
Like, I mean, is your feminine, like, female stuff right in there with hers or like, is it in a drawer?
Like, how do you guys rock your wardrobe?
Yeah, it's in a box that's in our closet that it's not out in the open because we do have people that come over and we don't want to risk that just kind of being out there.
But, yeah, I can buy stuff and then bring it home and show my wife and it doesn't have to be something that I am really hiding and lying about.
Right.
And does she ever ask you questions?
Like, did you dress today?
Or do you feel like she's just totally fine with it?
And it's like nothing.
She has no questions about it.
and she's come to terms with it and everything at this point?
I think that she has pretty much come to terms with it.
I think still those questions of,
does he really want to be a girl?
Is he gay?
Those type of questions.
I think they pop into her head every now and then.
I don't blame her for that because when you see her husband dressed that way,
it definitely can make you feel a certain way.
And on top of that, you know, I, you know, whenever I dress again,
I'm wearing breast forms.
I'm wearing abroad.
If it was just about the clothing,
then it would be like, okay, you wear the clothing
and nothing about your appearance would change.
But when I'm showing her that on top of her,
I like to see that I have breasts, that that, you know, makes up the look for me.
I'm sure that that makes it a little bit harder for her to say, oh, it's just about clothes and
he's fine, perfectly fine with being, you know, exactly who he is.
So that's kind of a little bit of both.
Right.
So sometimes she does.
Now, how do you think you got her to accept it?
Was she just a very open-minded person?
Did you educate her a lot on the fetish?
Did she go do her own research?
I think I just
I think she was kind of
clueless to this type of world
and never experienced anything like this before
which is so valid
but I think I kind of showed her that like when I said
that nothing about our relationship with change
other than this one the way I would be dressing
I meant it and I proved it to her and I think that when she started to trust
that you know I wasn't a different person
I was just the same person who enjoyed to do this one thing
that she was able to really wrap her head around and say, okay, this isn't, this doesn't mean
anything. This is still the guy that, you know, I'm dating and that I love and that I can be with
and he's not, I mean, you didn't tell me something. And then the next day, I don't know, just start
acting all different and have a completely different personality. Yeah, it's you and this is just
that you're still you like you said. Listen, I think somebody said it once on a podcast and I always
re-say it. But someone said, you know, like you have to really understand. And I don't know what
your girl did to like wrap our head around it. Maybe she went Googling without even telling you. But like a lot of
times what this, well, what this one cross-ters has said was that listen, you know, you have to like
understand that, you know, most of the time when you're telling your partner about your fat as you're
telling them for the first time. Think about like how long it took you to come to terms with it. You have
to give them time to come to terms of it. Right. Like you didn't you were you the minute you dressed up,
you were like, oh great. That's that means this and that's what it is and I'm clear about it and let's
called it a day, right? Like, no, it took you years to figure it out, right? Sure, I'm still
not 100% clear and confident about it. There's still some things that I question and worried
about and wonder, so I do not expect her to have it all figured out in any way. Yeah, well,
let's let's that be the last question. Like, what are those things that you still question and
wonder about? Question of, of if I feel like I'm in the right body, if I'm the right gender,
that definitely pops up a lot and it's something that I'm never really 100% clear on because,
you know, I always felt like, you know, I was comfortable on my skin.
Thankfully, you know, I was athletic and I was able to kind of fit in with the crowd.
So I never like had a feeling that I didn't belong.
But at the same time, I really felt like I connected more to the feminine things and definitely
with the clothing.
And so there are definitely times where I say to myself, like, I really feel like I would have lived a better life.
if I would have lived it as a girl.
Wow, that's interesting.
Yeah, so that's definitely something that pops in my head every now and then,
but I'm happy with the life that I'm living,
and there's just too many question marks with what would happen
and what my life would look like if I decided to,
if I decided to change my gender,
and so I just never got to that point.
Right, so what is missing?
Because you can dress at any time, right?
And so what is missing when you start to think, like,
maybe I need more, is it that you can't do it all the time and you can't do it outside?
Like, what would changing your whole gender and everything do that would be different than what
you have now?
Yeah, I think the main things, obviously, is just being able to dress at all times, you know,
outside and just not have to separate the two.
Yeah.
And, yeah, I mean, it's, it's, it's, it's, it's, the other part is more just, you know, you know,
social stereotypes the way that men normally behave versus the way women usually behave,
or at least, you know, the people that I surround myself with or have surround myself with,
that the women have a certain vibe with each other and the men have a certain vibe with each other.
And I feel like I always connected more to the way the women vibes with each other.
And so as a married man, it's a harder thing to try and be around the women because it's
kind of inappropriate at times, you know, you want to go and just hang out with some friend of yours
and she's married also it's you know it's normally seen as like sketchy so yeah but they don't
understand you're not coming from that place right exactly so right so it's just you know some
missed opportunities but those are kind of the main the main things what what makes you uncomfortable
when you're like being a guy is it that you just feel like you're more like what you just
explained like more in line or more interested in you know what the girls are doing than being a guy
Like what's uncount, like what is it about being a guy that's less comfortable?
I think guys just have to try harder when it comes to proving that they are manly.
Yeah.
I feel like, you know, women, and I've seen it.
I see it with my wife and her friends versus my friends that,
women, it's just a lot more freeing in terms of the way you communicate with each other,
and the way you act and the things you can say.
It's all a lot.
It seems a lot more freeing.
Obviously, I'm not a woman, so I can't come from that perspective.
but that's just what I'm seeing.
For guys, it's a lot of, like, having to put on this show of, like, we're guys,
and then we're tough and we're this and we're that.
And I just never connected to that.
Well, for women, it's the opposite.
I have, like, the problem because I'm, like, a woman, but I'm, like, very manly-like, right?
I'm super aggressive.
I'm very direct.
I'm even bossy.
Like, I have opinion, you know, so I could always feel a little bit like an outcast with the girls
because there is a stereotype of the way women should be, too.
It's a little bit there.
but I understand why you would feel, though, because listen, if you're hanging with the girls,
you're not like the girl like me, right? You're like the more feminine girls, right? Like, that's what
you have in you and that's what you like. So you would sort of fit in more in that world, right? That's
like kind of what you're saying. Exactly. Yeah, that makes sense. Yeah. Yeah, that's super
interesting. It's interesting to see like where you'd be. Because listen, I think your 20s are all about
figuring out who you are. You're still only 27. You have a couple more years left. So I like, you know, I wonder where you'll
be five or 10 years from now. I love where you're at right now, right? And I love how you see things.
And I love how clear you are about everything. I mean, you just never know where your life's going to go.
But I love that you're sort of, like I said, very clear about everything right now. I mean,
you have those questions and everything, but you do know that you're monogamous, that you're with
your wife, that you, you know, you might be into seeing a guy one day, but you're not going to do it
because you're with her and all that kind of stuff. Like you are very clear, even though you do
have these questions. And I think that that's a great place to me. Yeah, definitely. Yeah, I love your
whole story. I love that you're out and proud. I think that that's like a super interesting story because
I have so many people who are like in the closet, but I think people could learn from episodes like
this where somebody did have the balls to sort of put it out there. And what you're saying to people
is like, look, there are women out there that will accept this. Because I think sometimes the reason
why guys don't tell their wives or their partners is because they think there's not one woman
out there that would. And there are, you know, and you're here to prove it. Yeah, there was one that
wasn't, but that didn't deter you. You still did it. And the next one was okay with it. And she's
your wife. And so that's like amazing. I think that it gives people hope. Yeah, absolutely.
Yeah. Your wife's amazing. So I love it. So thanks so much for calling in. You want to send me in
some like anonymous picks for my crotchess things here for Patreon. I'll give you free access.
to Patreon for a month so you can see the comments.
And then I'll also give you free access to my Discord.
There's a whole cross-dressing channel over there.
So if you want to send me picks of you dressed, of course, Anonymous,
you could send them to my email, okay?
Okay, great.
Or sometimes what cross-stores do they send me?
Like, if they don't want to send pictures dressed,
you could also send pictures of your stash or anything like that.
You know what I mean?
That's the kind of stuff that people like to see.
But send me some picks sooner than later.
I would definitely want this up on my Fetish Friday episode.
So it should be up soon on a Friday, okay?
Okay. Okay. Amazing. Thank you so much. No, thank you. I loved your story. Thanks, Olivia. Thanks for calling in.
Sorry. Have we go on. You too. Bye. Okay. I just want to tell you before you go that my book, it's called Strictly anonymous confession. Secret Sex Lives of Total Strangers is now available not only in paperback and e-book, but you can pre-order the audio book. It's still not going to be out until August 25th, but you can pre-order.
it. The book is basically 17 different stories taken from my show. I kind of picked one story from
each category that I talk about on my show. Like there's a hot wife story. There's a cuck queen story.
There's a cuck story. There's a gang being girl story. Like I said, 17 stories. And they're all
told in the third person. And they're all true. I took the interview and rewrote it in the third
person. And I wouldn't really call it like a total erotica book. Think like Penthouse.
letters. It's more direct. It's not so over the top like erotica. I don't really like that kind of
vibe, right? But these are true stories. 17 of them. They're really short chapters, easy read.
You could read, you know, one or two and then skip around. You could read the whole book.
It's available in eback format, paperback format, and finally, the audiobook is available coming out
August 25th. But you could pre-order it now. And if you buy my book in any format or pre-order it.
order it, I will throw in a complimentary link to my Discord. My Discord does not disappoint. Okay,
there's no way you get into my Discord any other way than getting the link from me. Okay, I give it to
people who buy my book. There's tons of people in there. Everybody shares content with each other,
and that's what you get to do there. You can post your own pictures and videos. There's tons of
channels. We have lots of contests where you can win a lot of money. It's a super fun place to be.
It's a total strictly anonymous community and you will love it.
I will be giving anyone who buys my book access to my Discord.
It's private, like I said.
All you got to do is email me a screenshot of your purchase, whether you did the audiobook,
the ebook or the paperback.
Send it to me at strictly anonymous podcast at gmail.com.
That's strictly anonymous podcast at gmail.com.
And I will send you the link to discord.
So anyway, thanks so much for tuning in.
