Strictly Anonymous Confessions - 918 - FETISH FRIDAY: Tiffany is a Crossdresser who Loves Going Out Fully Dressed
Episode Date: September 13, 2024Tiffany is a c crossdresser who loves going out fully dressed and she called in to talk all about it. Tune in to hear all the details including when she realized she was into dressing up, how old she ...was he started dressing up in panties and lingerie, how dressing up made her feel, when she started buying her own lingerie, how she got caught dressed up by her brother and how he reacted, how she identifies sexually when dressed and not dressed, how she told her wife and how she reacted, how and why she repressed her dressing and when she picked it back up, the girlfriend he dated who was down for his dressing from the get go, how she helped her with her make up, hair, nails etc and got her to look passable and then took her out in public, how she felt when out fully dressed and the reactions she got from people, their Vegas trip out and how ad why she enjoyed going out there fully dresses, how and why her and her gf broke ups, how and why they remained close friends and how she still helps her with her make up and hair, how they want to start a make over business helping crossdressers become passable and then take them out in public, how she likes to dress when she goes out plus a whole lot more. **To see anonymous a pics of TIFFANY plus see anonymous pics of my other guests + get TONS of exclusive CROSSDRESSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $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://bluechew.com Get your first month FREE! https://butterwellness.com/ Try the Butter Wellness perineum massager and use code STRICTLY for 20% off your entire order 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/Strictlyanonymouspodcast Learn more about your ad choices. Visit megaphone.fm/adchoices
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Okay, today I have on Tiffany.
Tiffany's got a super interesting story.
Tiffany, of course, realized she was into dressing early on.
It was really lingerie at first.
That's what she started wearing.
Typical beginning figured it out when she was in.
young. She talks about all of that. And then she talks about how she was married briefly and told
her wife how her wife felt. And then eventually we get to the point where she meets this really
amazing girlfriend who she copped to the fact that she dresses right off the bat. And this girl not only
accepts it, but helps her out. She's a hairdresser. She makes her up. She gets him fully effing possible
and they start going out. Now they are no longer together. He talks all about that, but they're still
great friends, but he talks all about how that happened, how she got impassable, what it's like
being able to go out and look so good, and all that kind of good stuff. Like I said, it's a super
interesting story. You're going to get so many of the details. When you listen, I'm not going to
give them all out here. Because people think my intros are too long to begin with. So I'm going to
get right to it and be right back on with Tiffany. Oh, and I have pictures of Tiffany on my Patreon.
And pictures of all my other cross-dressers on my episodes, their pictures are on page.
I forgot to say that you get anonymous pictures of all of my guests, all of the cross-dressers, too.
Okay.
Patreon.com slash strictly anonymous podcast.
Anyway, I'm going to be right back on with Tiffany.
Hi, Tiffany.
Welcome to the strictly anonymous podcast.
How are you today?
Doing great.
How are you?
I'm good.
So Tiffany, you're a cross-dresser and the way I always run my cross-dressing episodes and any of my
fetish episodes.
I always like to go way back.
Typically, it goes way back every now and then.
recently I heard some people where it didn't go way back. Let's go back to whenever it was that
you realized you were into dressing. What were those first memories for you? Oh, that was,
I would say probably eight, nine, ten years old, kind of just times going shopping with my,
with my mom and just always liked looking at the women's clothes a lot more. And then getting
into the preteens when puberty starts sitting. And I remember,
I remember going in my parents' room and seeing some of my mom's dresses and stuff.
I was like, I want to try that on.
Interesting.
Like, just the thought popped into your head.
It just looked pretty.
Yeah.
I was like, you know.
Curious.
Yeah.
Okay.
So that was pretty much the beginning of it.
But wait.
So let's talk about that first experience of you actually putting it on.
First of all, I'm assuming everybody wasn't home.
Did you put it on and just immediately take it off?
Did you put it on and leave it for a couple of hours?
What was that first experience like?
Nobody was home I remember putting on.
I probably had it on for 20 minutes or so.
Okay.
It's kind of standing there, looking in the mirror, spin it around, like watching the dress spin around and flow out.
Yeah.
And how did it make you feel?
Was it about feeling feminine?
Did you feel like a different person?
Was it about thinking like there was another woman with you?
What was it about?
Do you remember anything like that?
Just feeling beautiful.
Feeling beautiful for you.
You feeling beautiful.
Yeah.
Okay.
Yeah, it just felt beautiful.
It felt natural.
It just felt kind of euphoric in a sense.
It's just exciting all together.
And I didn't really understand it at that age.
I'm like looking back and but I just remember like, I like this.
I like the way it looks.
I like the way it feels.
I like how I'm feeling.
Yeah.
And feeling myself.
Yeah, totally.
And it felt natural.
which is key. Yes. Like it didn't feel like you were doing something weird. And that's where I think the people are born with these fetishes maybe, right? Because why does it feel so natural? Typically, I mean, maybe there's people out there that tried something on and they were like, what the fuck? I'm never doing that again when I never talked to those people. But most people that I talk to that do have a fetish. It typically does the first time it sticks. And I think it sticks for a reason.
Yeah, definitely. And it's something I've come to really enjoy. There was a time that.
that it was, I kind of boxed it up and put it away.
There was changes in it.
Obviously, I was growing up and then being a young teen and then moving out and having
all your buddies, his roommates and stuff.
It's not something you're going to go do, you know, with a chance of that.
But there was things I had hidden in my room.
And I pretty much around like mid-teens, I was living, my parents had got divorced,
we're living in an apartment with my dad.
And I remember doing laundry.
and I found somebody had left
some panties
in the laundry. I didn't notice it. I had
folded my laundry. Where the heck
do these come from?
Do you have sisters or was it like your stepmom?
I don't. Your dad's a
girlfriend? Yeah, it was my stepmom.
No, it was my stepmom was his dress.
Clothes now. That was somebody
random in the apartments. I had no idea.
Oh, this is you're living with your friend
or you're living with your father?
Living my father, yeah. Okay, but you don't know who's
panties there, but you have girls in the house living with you?
No, they were in the apartment, so there was whoever was dealing laundry before me had left stuff in the dryer and missed it.
I don't know why I'm so confused. Is this like a downstairs dryer? It's not in your house.
Yeah. Yeah, that's not in the house. Community, you got to wait in line. People take forever leave their stuff there all day.
No, no, I know what you mean. I know. I finally have an apartment with the laundry in it. So I forget about that life, but I get it. Okay. So you find these panties in their left behind.
And, yeah, it was full of my laundry, putting it away.
And I'm in my room.
I'm like, what the heck?
I'm like, well, these are cute.
I'm keeping these.
And it kind of flashed back to years before.
I'm like, I've never had something that was my own.
I was kind of cool.
Yeah.
And eventually I went to the sex shop and I bought some lingerie, made up some BS story to a lady trying to like,
oh, yeah, my buddy's turning 18.
were joking with them and
thinking they're going to judge me
and they're going to be like, they've heard
all. Yeah, now they
don't care at all. Why was
I even thinking that? But I had that stuff
like I had some stuff hidden and
when I wanted, once in a while
if I wanted to
masturbate and have and feel
that way, I could just lock my door in my room
put on some sexy lingerie
and enjoy, you know, a little bit of time by myself.
Right, and that got you turned on. Now, when you
were home because we just like fast forward to your teeth like you're a little bit older now but when you
were younger after that first time you tried your mom's dress did you continue dressing for a long time
or did you suppress it immediately i continued sneaking in as much as i possibly could
sometimes they locked the door but there was a back door to their bedroom and i knew how to get my
hands through the little slats in the window there's like one of those opaque windows with just a slats
and I knew how to basically slide my hand in,
prink it enough to be able to unlock it and sneak in if I wanted to.
Okay, cool.
So now you're living with your dad.
You're trying all this stuff.
During this time, do you ever wind up getting caught?
My brother caught me once.
And what kind of compromising position were you in?
Did he just find the article or find you dressed?
No, and I had some lingerie, and I was just wearing it.
And I was just walking out of the house.
And he came home.
He's like, what?
Oh, my God.
I didn't see it.
He's do whatever you want to do.
I don't give a shit.
Wow.
That's pretty major, though, don't you think?
He never brought it up again?
No, he's whatever, dude.
He's like, do whatever you want.
I don't care.
Maybe he was dressing too.
Maybe.
You don't know.
He just didn't.
And he's still like that today.
He's kind of like one of those.
Do your own thing.
Yeah, that's cool.
All right.
So it's just his vibe.
It's his personality type.
That's great.
Lucky you.
He smokes a lot of weed and doesn't give a shit about anything.
Yeah, yeah.
Lucky you.
because some brothers or sisters would run with it, you know what I'm saying?
Yeah.
Yeah.
And my brother, my brother, he's got, he's got physical issues, handicapped issues.
And there's things he can't do, things people look at him.
So I think he kind of looks at it like, people look at me and try to judge me,
where who am I?
Oh, yeah, he's super.
Yeah, that would make him, of course, super accepting of anything that's different because
he's different and he lives in that world.
Okay.
So that's an important fact to say why he didn't really react.
That changed to you.
probably felt more comfortable with you. You're like him now. You got something like whatever.
Yeah. Do you want? Who cares? All right. Cool. Okay. So you're still dressing and now it's like a turn on for you,
right? Now as far as like how you feet like your sexual identity, right? Because there you are jerking off.
You're like dressed up as a woman. Are you into women? Do you ever think, oh, while you're dressed,
are you imagining you're with a man? I mean, what were you, what's going on with you in that in, in that world?
So it's very weird.
So into women, love women.
Everything about women is absolutely stunning and beautiful.
Some guys are boob guys.
Some guys are butts guys.
I'm both.
Your butt boobs, anything that goes with a girl.
Yeah.
I would say boobs probably above butt.
Okay.
And part of that stems from my stepmom, who I used to wear her clothes,
when I was probably about six or seven.
I remember getting up to get water and I walked by and that was when my parents were just started dating and she was in the bathroom getting ready and she was standing there topless and she had.
Right.
And I remember seeing I'm going like, what?
And that was the first time I ever saw boobs in my life.
And I remember coming back from getting water and I was like, I'm going to go quietly.
Maybe I'll see him again.
She had realized I walked by and shut the bathroom door so that.
Yeah.
That didn't happen, but I blame that on my love of boobs.
She had realized I walked by and shut the bathroom door, so that, that didn't happen.
But I blame that on my love of boobs.
Yeah, well, I don't know.
My son is, like, obsessed with boobs, and I ask my other friends who have a, like,
son.
Yeah, they have that have son male babies, like sons, two that are, like, my kid's age.
Because my son's only eight, but you see it so early.
Like, he is just obsessed with boobs.
boobs. Like it's just his thing. And my friend said her guy is the same way. And my son,
the bad thing is my son is always like squeezing my boobs. He loves touching them. But he's
only eight. But he looks like he's 13 because he's like gigantic. So if we're out in public
and he started squeezing my boob, it looks very inappropriate because he looks really old.
You know what I mean? And he still like, oh, she's one of those moms that still breastfeed?
Yeah. Yeah. It's so weird. It's so weird. But anyway, so you so okay, but did you ever think about
men though like during that time while you were dressed? Because some crossjusters are
do feel like have this thing of with to be with guys when they're dressed tell me we never until
kind of recently and um my ex-girlfriend who's my best friend um we're still best friends and she's
the one that kind of brought out a lot of it um we were having a conversation and i was like
i don't know i'm like yeah sometimes being dressed up like it kind of like crossed my mind would
it be fun to go down on a guy. I'm dressed as a woman. I'm acting as a woman. Yeah. That's a very
womanly thing to do. Makes you feel more feminine, even more feminine, right? Yeah, exactly.
Yeah. And then she's so just one. I'm like, what? You want me? We're like two and just be a
total, total slut. I'm like, I don't know. Like, kind of sounds hot, but it kind of, you know, it's one of
those, you know, sounds fun, but. Maybe not in real life. Yeah. I don't know. Yeah. I don't
know but no I could never I just I love women too much well I can't wait till we get to this
girlfriend of yours a quick question I just want to fast forward to like right now like right now like
right now how old are you in are you in a relationship married living as I am single right now
single right now I was married okay for a while and I will be 46 next week okay cool now when you were
married did your wife know is that or no I brought it up to her only about wearing a lingerie one
month or twice. And then finally she said, if you want to wear it, fine, wear it. And it's, yeah,
that's not really my thing. Doesn't really, she didn't really enjoy it. Maybe once twice a year,
she'd be like, hey, do you want to wear something tonight? She threw it to you. Okay. Listen,
that's that. Caitlin came out during that time. And Caitlin, Katelyn, Jenna came out during
the time I was married. And Halloween was coming up. I'm like, I want to go as Caitlin. Oh, yeah. Oh, my
God. And she was like, that's hilarious. Do it. Yeah. And she's, I think,
you're enjoying this more because you get a dress up um i didn't know about breastplates or anything like that
so basically just had a nice blouse type top we had got and just had a bra and kind of stuffed it with a bunch of
bra padding and then had our friends house we're going to their daughter which was about 17 18
her friends are like no no no we need to your makeup better we need to contour your chest and they
contoured and may look like I had more
sleevedage and stuff. And then funny
enough, one of our friends showed up as a St.
Polly girl, so both me and another
buddy were both dressed up as women
for Halloween that year. But I rock
six inch heels all damn night.
My legs hurt like
a son of a bitch the next day, but
I bless you women
for wearing them, but I rocked them.
And I have no problem walking in heels.
Yeah, well, you know, if you think
about how many men
dress up as women for Halloween,
You have to wonder if a lot of them are cross-dressers, and this is their one time where it's acceptable.
Do you know what I'm saying?
Like, for real.
Yep.
Because where there's one, there's many.
Go on a cruise.
Go on a cruise during Halloween.
Because then you can just dress up the whole dang time because everybody's dressed up the whole dang time anyway.
Oh, my God.
So you could just be Caitlin all to the time.
You should.
Out and proud.
Out and proud of what you're doing behind closed doors.
Exactly.
Yeah.
So wait, let's go back to your chronological.
So you're like living with your father.
Now, now when you start living with your.
friends, right? You said at some, is that when you kind of suppressed it?
That was when I kind of suppressed it. Okay. I don't know. I just kind of like not doing it for
a while, kind of just went away and just didn't really think about it too much. And then it was kind of
being a typical single young male and there was a steady flow of women through my life at that
time. So as my, my ex-girlfriend said, she's, yeah, you were a whore when you're young. I'm like,
Yeah, I had no problem.
So that was, I kind of got suppressed during that time.
It didn't really, I don't know, maybe 15, 16 years kind of just put it away and never, I never really thought it was possible to even dress up completely.
It was more just at that point, just all wearing lingerie during playtime.
And that was just, that was pretty much the extent of it at that point.
Just lingerie, not fully dressing.
Yeah.
Okay, cool.
So you would still do that, but you weren't fully dressing.
Correct. And I didn't even have any clothes, really. There was, I had two long-term relationships. One of them a couple times I tried on her dresses. They didn't really fit too much. And I was like, that was only if she wasn't home and it'd only be for a few minutes. I was too afraid of something happening and her finding out. And then it'd be like, okay, now I got to explain this shit. How's this going to go? Yeah, yeah. So at this point, you hadn't told anybody. You weren't ready to tell her. You weren't going to tell these other girls.
Correct. Okay. So it's a secret life. Now, eventually, when do you meet your wife?
I met my wife in my late, about, I don't know, late 20s, 28, 29, 30.
By then, had you already picked it back up? Because you did say you suppressed it for a while.
I pretty much suppressed it with her in time I ever dressed up with her as Caitlin.
Oh, okay. But you did tell her.
I had mentioned things to her about it, and that was only in bed, and she was like, yeah, not my thing, not my thing.
Once while she did it just for, oh, it's your birthday, fine, if you want to do that tonight, go ahead and enjoy it and do that.
So that was like the extent of it just a few times.
Now, if she wasn't home, I was, you know, I had a little secret sash of stuff.
I could grab and throw on some lingerie or something or throw on a dress and walk around the house and enjoy it for a few minutes.
But that was a few and far between.
Okay.
Because listen, by the time you probably met your wife, like Amazon is now available.
And I feel like that changed a lot of people's lives in the fetish world because you could kind of like order your own stuff on the DL, right?
That was the first time.
Well, you have to do that second Amazon account because when you're married and wife is access.
So it's still harder.
And I had two Amazon accounts, one for work and one for myself.
And I was able to order some stuff up towards the end of our marriage.
She went to see her friends.
She was gone for a week, week and a half.
And I had planned.
I was like, okay, she's been gone.
And that's when I found out about the breastplates.
I'm like, okay, I can get pressed on nails.
And it was just nails, lipstick, ordered like two dresses, ordered a pair of heels.
and was able to like pretty much the whole week hang out and I was during COVID.
So even a couple times I ran to check the mailbox or something.
Oh, everybody's supposed to wear a mask.
Nobody can see anything.
So even if I had fingernails on, nobody can see.
I kind of enjoyed that whole week by myself just dressing up and I really like this.
Okay.
And this marriage is pretty much over at this point.
A few months later it was done.
And I was like, you know what?
Going forward, I'm not going to hide this.
This is like bullshit.
Why am I hiding something that I enjoy doing?
Yeah, interesting.
Okay.
So I kind of just put that out there after getting divorced, dated two girls.
One was like, eh, not my thing.
But when would you bring it up?
Explain that story.
So you decide, okay, I'm going to go into every relationship of the upfront.
Do you put it in your dating profile?
Do you tell them on the first date?
Like, when does that information come about in your story?
relationship with these girls?
I told them probably within the first two months.
Okay.
And just something came up in a conversation.
Usually started with the having sex and, hey, do you want to get some lingerie?
I mean, hey, if you don't want to wear it, I'll wear it and kind of say it jokingly
sense.
And then gauge the reaction.
That was pretty much how I brought up my last ex, my best friend.
I think it was the first.
week we were together and we were talking about something and I said yeah and I'm like yeah if you
didn't want to do it I'd wear it because I enjoy it that's kind of like my thing and she went wait
what she's like so what do you so what do you have and I'm like I have some stuff she's like okay
I want to see it just like do you have clothes and I'm like a little bit and then she comes over and
she's okay let's see it pull it out all right put
it on. No, ugly. Put it on. That's cute. Save it. Oh, my God. I like her. Yeah. And went to the whole thing
and then 90% of my clothes. She tossed. And then even the other day. Yeah, even the other day,
I was, I was helping her out and I, she had a, she grabbed a little sweater to go out. I'm like,
oh, that's cute. And she's like, yeah. Oh, crap. This is yours. Isn't it? I'm like, yeah.
You can have it back. I'm like, no, go ahead and keep it. It's fine. So wait. So you must have been like,
oh my God, I hit the jackpot. This is a girl you just met two weeks in.
She's like open to it.
She's not shutting you down.
Yeah.
She was really open to it.
And she's, have you ever gone out?
I'm like, well, no, there's no way in hell I could go out.
No.
No, I would never, would never, ever, ever, you know, be passable.
Yeah.
And she's like, yeah, you are.
Now, mind you, she's a hairstylist.
Okay.
She does makeup and hair.
She's done it for years, 20-something years.
Uh-huh.
And she even says, she's like, I saw something new.
when you first set it.
And then she said, then I gave birth to you.
We started dating around Halloween.
We met at a Halloween party.
Uh-huh.
As just as my favorite character.
Who's that?
Tom Cruise.
Oh, Tom Cruise.
Okay.
I love him.
Top Gun.
Yeah, I love him.
Don't think, do.
I love him.
Before Christmas, she set up and she went to her hair store, got a wig.
She went and went shopping and bought some stuff.
And then we got a hotel room.
And she's like, okay, I need you to completely shave before getting here.
I'm like, all right, well, I'll just go to the barber down there.
It does the, you know, straight razor shave.
Went down.
She had the entire hotel room decorated.
She had flowers, candles, everything set up.
I always joke, koochee board.
She had a little chitutri board or whatever, however you say that.
Yeah.
Whatever.
Yeah.
It's like worst.
It's like worst sauce.
Somebody screws up.
Yeah, you're right.
Champagne and stuff.
And she proceeded to do full makeup, nails, put this on, did a photo shoot with sexy Santa lingerie on and stuff, put on clothes.
And I told I said, I won't leave the hotel room.
There's no way.
And then she's look in the damn mirror.
And I'm like, holy shit.
Hey, guys, I can tell you exactly.
what girls are into, okay? They're into guys with confidence, and that's especially true in the
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Did a photo shoot with sexy sandalong.
lingerie on and stuff put on clothes and i told i said i won't leave the hotel room there's no way and then
just look in the damn mirror and i'm like holy shit no way why why did you look like and i'm like i don't
even look like me i this is somebody i don't even there's you can't tell wow i'm like well let's go
downstairs and take a picture by that christmas tree well they had a christmas party going on the hotel
We walked downstairs and there's like a group of four guys checking us both out.
And I'm like, okay.
What are you wearing?
What are you wearing?
Can you paint the picture?
I just had jeans.
I had jeans.
Okay.
Well, actually, I had a leopard print dress.
There's a leopard print on the top, black on the bottom, some heels.
I think I have, I think I had wedges on maybe.
Okay.
Might have been wedges.
You have a wig?
I had a wig on.
Okay.
And that was like one of the first ones.
She went and bought me a realist.
I can dye.
I can bleach this.
I can add highlights.
Add tensile to it.
So that was an expense.
That was like almost $300.
Yeah.
For sure.
Real hair is expensive.
Yeah.
But when you're dating a hairstylist, they ain't going out with a fake shit because they can tell.
Yeah.
And she's like, I can tell.
Other women can tell.
I need to make it as amazing as possible.
so it's less, you know, any less, every little thing you can just kind of add enough.
She's like, so you do this, this and this.
And we went through, she kind of was like, okay, nope, you need to sit like this,
you need to stand like this, pop your hip like this.
A lot of it I did very naturally just from observation of women over the years.
And she still was like, I cannot believe that you can walk so damn good in heels.
She's like, freaking amazing.
And you have great looking legs.
Damn it.
So we went out, drove around, went to a drive-thru, got food,
and stuff. That was the first night, and that was the first trial run. A few months later,
we went to Vegas. That's when I had the real wig. We walked the strip, went to casinos,
went to a drag show. After the show, there was like two drag queens, and they even came up,
like, it took me a few minutes to figure it out. And it was the second time I came out by the time
I figured out, holy shit. That's not two women sitting at that table.
They're like, you look amazing.
Great job.
And that was a really, like, big, confident boost here for me.
Like, okay, these are professionals.
They didn't realize it.
Wow.
So even.
Okay.
And now when she, my girlfriend at the time didn't even do my makeup.
She did like nails on this and that and put like, I think she put the eyelashes on me.
And I got dressed and then walked through the mall.
and this is where like bringing out my confidence like eff it walked through the mall and went to mac and had an appointment at mac and had a lovely gay drag queen that worked at mac do my makeup oh wow now did she know that you were a guy yeah okay and was like i used to do this i used to do competition you look amazing you don't even need that much you're like pretty much passable with very very little
my makeup and then we walked around, went shopping, and then went all over Vegas.
Nobody said anything.
Wow.
Nobody looked at me weird.
Nobody go to a bar and order a drink.
Bartender kind of doubled back.
It's like, wait, what?
The voice is the one thing you can't hide.
At least I can't.
It's very hard for me.
My voice is pretty deep.
Yeah.
So trying to hide that is.
And that's when my girlfriend would be like, oh, I can go to the bathroom.
We'll be right back.
Leaving me, knowing that now I'm going to have to talk.
Exactly.
So it's kind of like throwing me to the wolf.
Like, stop being a little bitch.
And so what did?
Did you talk?
I did.
I did.
And I just, I did.
I just owned it.
I just didn't give a shit.
It was, I was worried about it.
Oh, people are know.
People are looking weird.
No, they're not.
Nobody cares.
Nobody cares.
Didn't care.
Yeah.
Didn't care.
Order the drinks.
Hang out.
Sit out of slot machine.
Playing machines.
Wachers comes up.
And generally, the guys were only the one, the male bartenders and stuff would be the only one that would kind of double take.
And then they're not going to say anything because it's 2023 at this time.
You can't say, yeah, you can't say shit.
Now you get looked at it.
So you ain't going to say anything.
So, but then the women.
cocktail waitresses walk around
would just smile
and they
seem like they enjoyed it way more
like awesome so there was
a total
difference in it but it was a hell of a lot
of fun and I
never thought that ever would be possible
until her and she's the one that kind of
like she says I birthed you, I'm the one that
told you it could happen and it's like
when I saw you dressed up
she said I knew
she's like you're not you
so you are way
Way hotter as a chick than you are as a guy.
Okay, let's ask, let's find out.
So as a woman, what would you rate yourself on a scale of one to ten?
And same as a guy.
I would rate myself probably a solid seven and a half.
As a girl?
As a woman.
Okay, that's high.
As a guy.
Five or six.
Wow.
Now, let me ask you this.
So you meet this girl.
I mean, like it's amazing that you meet her.
How long, by the way, did you guys?
guys date for. I know you're still friends, but like you're not dating anymore, right? How long are you guys friends?
Or just how long did you date for? We dated for about a year and a half. We've broken up for about
three months now. Why did you break up? She needs to explore herself and her life and things that
she's had on it. She has a girlfriend right now. Oh, okay. That's interesting. So she feels like she might be
gay and she wants to date a woman or something like that? And she's figuring that out. She's, she
experience she messed around a little bit when she's younger the other day I asked her I'm like okay
your first day went well yeah and she stayed over I'm like okay did you try the pie did you
have something because you had never tried pie before yeah she's like did it doesn't taste like
anything I'm like was it great shouldn't taste like anything so it should yeah yeah yeah if it's
crusty that's a problem yeah if it has any kind of odor that's something's wrong yeah she never
so actually I'm I was oh I actually stayed with her
last two nights helping her move.
She does a little tiny house living and I help her.
Oh, she has one of those?
Is it cool?
Yeah.
Does it look as good?
Can I ask you a quick question about those?
Does it look as good as it does in these magazines that they show you these little
tiny house places?
She does a tiny house with a trailer, not a full on tiny tiny house, but that is a dream.
Yeah.
And that's something she's like, oh, and you're going to build this for me.
Okay, cool.
All right.
Let's get back to her.
So you were just helping her the other day.
I'm still helping her today.
And then her girlfriend that she just started dating is coming over today.
So I'm assuming your breakup wasn't bad considering that three months later.
It shattered my fucking heart.
Okay.
Oh, so what happened?
Did she just come to you one day?
Or was she talking to about it a lot?
She was done.
I just, I don't, I'm not feeling anymore.
I just can't, I can't do this.
And she had fallen in love with me big time in the beginning.
And then I was trial bond, not ready, holding off.
okay every woman's left i don't want to put the effort out and then finally you know four or five
months in i'm like okay i'm going to put the effort all the way out she was kind of nope you didn't you waited
too long tried working it for the next year there was good times there was bad times and it was like
it's just not so i was not expecting it it kind of came out of nowhere right so you because you had
never you had no inkling of this before i knew things weren't good and
relationship, but we were working on it.
We were trying. I thought we were.
But I mean, she had never mentioned to you that
she might feel like she
wanted to be with a woman. Oh, yeah, we had
talked about it. Okay. We had talked about it. We had talked about
maybe we could add a woman,
go into the Swinger lifestyle.
Okay. We had looked into
that. And
when we broke up, she started
talking to people, she's like, I might be
a couple of want me as a unicorn. She's all
excited and happy. And I'm like,
well, damn, like,
Why can you stay with me?
Damn it.
Yeah.
But she even all of a sudden, she's like, you know, I get this figured out and then I can find something with me and you.
Like, this would be great.
I love her like a best friend.
So even though we broke up, that love and that friendship on both sides is still there.
When she's told, she dated a couple people after we broke up.
And she told the first thing, like, my best friend is my ex-boyfriend.
He's going to be in my life.
he's going to be part of my life and now she's got the girlfriend they've only been dating like two weeks and she's
already said oh we get married you're going to be my maid of honor you're wearing a dress and her new
girlfriend's no he's wearing a skirt she's wearing she's wearing she's wearing she's wearing she's
I love how you guys are both making choices for me already oh my god how old's your girlfriends
how old is she she's five years younger she's 41 so had she ever been married she has okay so she's
single and now.
16 years and two kids and
Now do you think that there's a chance if she finds a woman who is down for you entering into the relationship that you would ever have a place in there or you just will remain friends?
100%.
Yep.
Yeah?
That's a possibility.
Or into her, I have the most beautiful cock in the world.
And it's the best thing is she wants to mold it and sell it.
She's like, seriously, we can mold this and sell it.
It's that good.
Yeah.
She's, it's.
So, yeah.
If there was a situation.
like that, she's even sad.
And then her and her girlfriend were like, they've already talked like, I want to make
videos.
She's like, yeah.
So Tiffany said, I record it.
And she's like, well, we do need a videographer.
So even the new girlfriend was like, eh, she wants to record it.
She can record it.
She would allow it.
So there's even like already open this there.
Like she knows, but she knows about.
She knows.
And she's, that's great.
Her girlfriend's been open and out for a long time.
And she's like, I know places we can.
go. Let's plan it out and let's do our makeup and let's all get dressed up and let's all go out.
This is a thruple in the making.
So, but then it's where do the emotions come in?
Somebody that you still adore that you're with for a long time with somebody else and then you get brought back in.
So it'll be interesting to see what happens if something ever does happen.
Well, let me ask you this though, because that girl wasn't involved when you were with your girlfriend and you said that you guys did
have problems when you were dating. So maybe is there a chance that you guys just aren't
compatible dating regardless? Because what were the issues that you had with her to begin with?
It wasn't that she was gay because she wasn't bringing that up. It took you by surprise. So is it
just you guys maybe aren't compatible as lovers anyway? Love, yeah, love languages are
completely different. She's very spiritual numerology, all that kind of stuff. Yeah. I learned a lot about
it. And sometimes it's, I think, one of the best ones I saw was just because your moons here
doesn't mean you can blame your attitude on that. Don't stop using that as a crutch. I get part of it,
but don't blame all this on your shitty attitude and shitty decisions. So, you know. So,
but you just weren't compatible is what you're saying. Yeah, we weren't, but we're way more
compatible as friends. So maybe even if you were brought in, you're going to have to get to
place and I think over time
that will eventually happen maybe I don't know
because you're not really taking any time apart
but you're gonna so that you don't
get emotionally fucked again
right because you already had to
rip the band-aid off and it really hurt like
you said you don't want that to happen again
I mean I think it's hard to get
over somebody when you're actually seeing
them all the time but there's nothing wrong with that I love
that you guys are still great friends but I just
she was dating somebody and needed to move
her trailer and he was living
with her because he moved in really quick
I mean, he was only around for about a month and a half.
I went to help move his ass out
so I can move her trailer.
But all these things might not ever...
That was a little awkward.
I get it, but I don't care.
We're talking about your crowd.
This is a cross-ressing episode.
I don't want to get too involved in that.
But what I'm just trying to say is that you just want to make sure that...
Because regardless of whether she's gay or not or whatever,
you guys don't work as a relationship.
So whether you're ever brought back...
Yeah, but yeah, so whatever.
whatever so if you're ever brought back into that thing you start videotaping you start sleeping like
you know i just i want you to maybe make sure that you still continue to go and try to find
you're a partner for you that you can be more than just friends with benefits with because
most likely it's never going to work out with her didn't in that whole year and a half so it's never
going to but like you don't want to get so stuck on keeping her around and getting crumbs from her
and then never going and finding your own relationship because she's already moving on.
Correct.
Correct.
And there's some of it like she's still teaching me things on makeup and stuff.
So it's really, really great still having somebody that you.
Yeah.
See, I mean, that's the Catch 22.
I mean, like the fact that you have this woman in your life, regardless of whether you could be in a relationship or not.
I mean, that friendship is like invaluable to you.
This is like the first woman that was so.
accepting. She's helpful. She's still doing that. Still helping you do stuff. Like, how could you ever
not talk to her? But, like, maybe you just won't date her. But what a great friend to have.
Extremely. And there's things that I need to learn makeup wise. And she's times that we've, there's been
sometimes like, okay, let me show you how to do eyelashes. Okay, let me show you how to do this.
Okay. You need more practices. Keep practicing. So it's not full dress up or anything, but maybe
we let's practice on do your lipstick, do this, like little things and just the repetitiveness.
Because as women, you guys grew up learning how to do your makeup.
Yeah.
You guys have all these years of experience.
Some of you are way better than others.
I'm horrible at it.
So it's having somebody.
Yeah, having somebody to help me and somebody that is now dating somebody in that community
that is totally open with it, cool with it.
and she's even excited like let's go find him somebody yeah that's amazing yeah that's amazing so having
having the cheerleaders having your back and somebody that you're comfortable going out with
because that was a big thing for me is the confidence of going out going out fully dressed up
yeah and get looked at him is something going to happen yeah um having people with you just kind
of breaks down that whole anxiety issue and it's just and explain that to other cross-dressers
there who are listening who have never had the balls or maybe the best friend to get them to do it what is
how do how is it to be out and proud in public with something that you had kept hidden for so long
it's amazing yeah and even me and her have talked and she's like i want you need to go find other
people like you that enjoy this but are scared maybe we can start a business doing this and
go out with them. I can do their makeup. I can do this. And then take them out and let them experience it.
Where do you live, by the way? Southern California. Oh, because I just had a guy on. Did I, did I tape him yet or put him out? Oh, yeah, he was my Michael. No, Michael, my fetish Friday, Michael. Did you hear that yet that episode?
I haven't heard that one. Okay, because he's in Vegas. He's in Vegas. Okay. And I'm just going to tell you, he was, he's literally looking for someone to go out in public with. And this guy is so fucking.
Vegas is a huge event in October.
Listen, this guy is so passable.
No offense.
I've never seen your body, but this guy's body and fully dressed.
I have pictures of him on my Patreon.
You wouldn't fucking, like most of my friends would die for his body.
Okay.
Like he is very skinny and tall and he fully dresses and he's so passable.
And he's looking for a buddy who lives in California because he's close enough and he's in Vegas to hook up and go out with.
You guys are like a perfect pair.
great name too
and he has a good name too
so Michael
solid name you gotta go with Michelle
or Michaela or something
yeah I don't remember is it Michael like I'm
trying to think but anyway so let's keep
I'll have to check it out I'll listen to it
yeah so you're thinking about yeah I just aired it on Friday
you need to listen to that episode and then if you want me to put in contact
with
with her I will fetish Friday
Michael's into cross-dressing panty hose
guys and more he's a little into guys
you gotta listen to the episode and if you want me to put you guys in
I can because what you're thinking kind of like is like what he's into.
But I do think it's a great idea for you and your girl friends to set something like that up.
Because imagine helping other people do what she did for you.
Yeah.
They get the full hair, hair, nails, makeup.
And she's got like probably 15, 20 wigs now that she's even got something like,
oh, I want to put a wig on and work something different for the day.
So she can get that stuff, but then be able to help somebody and say, look, yeah, it is possible.
You didn't think, I didn't think I was possible.
I didn't think there's any way I could go out in public.
She completely changed my perspective on it and built my, and the main thing is it builds the confidence.
Totally.
Because a lot of, a lot of guys are lacking the confidence because they just don't, you know, don't think it's possible.
But then once you experience it, you're like, so bitch, this is the, this is the,
amazing. And it, the weight that came off my shoulders the first time. And she even said,
she saw it. She's like, you were extremely more confident. She's like, don't get me wrong.
She's like, I like hanging out with her a lot more than I like hanging out with you sometimes.
Because you're in a bad mood. It's not like, you're just annoying. That girl, she's always in a
fun mood. And she's always listening and she's just fun to be with. So.
Tiffany is better. Tiffany's cooler.
And I've been on a couple like websites and stuff and posted pictures.
And I've had other cross-stressers and trans people are like, you're hotter as a chick than you're as a dude.
And it's kind of funny.
I'm like, damn it, why does I keep hearing this?
Now, do you ever see yourself being like completely out and proud?
Because I know you go out with her and you do this.
But does anyone in your vanilla life, your regular life know about this besides her?
Not really. Nobody really knows.
It's, she's even, we've had a lot of deep conversations about it.
She's like, you want boobs.
I'm like, well, yeah, they're freaking fun.
I'd probably just play with them all day.
So, nah, you'd get tired of them.
I'm like, but that's for me a big thing about passing.
I also thought you needed a breastplate.
Yeah.
I don't have a lot of extra skin.
I'm pretty thin.
But even the tape-in bras, she was able to tape up really tight and create cleavage.
Yeah. And to me, that's what was a big seller on my confidence of going out is a little bit. And she's not, she's got, she all says, I'm part of the Itty Bitty Committee. She's like, you don't have to have, it just looks too obvious and too, too much. She's like, they have padded bras, they have padded shirts, create a little cleavage. The rest of it's all under padding, nobody's going to see it. Totally works. And it looks more realistic.
Yeah.
And she's a look at, we went online. She's like, how fake that looks.
people are going to see that. That's the first thing I can see. Then I'm going to start looking at
noticing other things. You look more like a caricature. You know, you want to look more
possible. She's smart. She's saying that you want to look more possible. Be more real.
You want to blend. You want to blend in. You don't want to stand out. You're not wearing the stripper
platform heels. Yeah. I was going to ask you, what is your vibe? We have like 10 minutes.
What is your style of dress? What do you like to wear?
I like, obviously, it's easier with like a flowy type of dress towards a waist. It's easier to
hide, especially when tucking, and I'm getting better at that.
But, yeah, like, more of a midi dress or a skirt is more of my style.
Wedges are, you know, a love.
It's easy to walk in.
I mean, yeah, I can rock, I can rock six-inch stilettos, but, you know, bitch walks around all night,
six-inch solos when I start on stage.
Yeah, uh-huh.
So.
What color hair do you like?
What's like your favorite wig, what, you know, that you like to wear?
My real hair wig is my favorite.
It's brown.
She wants to add some highlights to it.
And now everybody's doing tensile in their hair.
I don't know.
You've seen that.
No, not really.
Brade in like little tinsel strands and those different colors.
So you can do red, white, and blue during Fourth of July.
You can do red during Christmas time.
But having hairstylists is somebody, I don't really get to choose.
So my hair is done and I don't get to choose.
That's pretty much something I've given up.
Because she's like, nope, this is what's, but I do want some blonde streaks in it.
So it's going to be more of a brown with some blonde highlights in it.
Okay.
And now how many times is it a monthly thing, a weekly thing, a yearly thing, like how much are you dressing up and, say, going out?
Once we did that, it was about every, about every two months to the end of a relationship that dressed up and like full dress up.
We didn't always go out.
A lot of it was just around the house.
If we didn't have the kids, then there was a lot of days I put this on.
I want you to wear this skirt, wear this lingerie, cook me dinner.
And we would have fun just walking in the house, cooking, and I'd be dressed up just around the house.
Not fully dressed up, but at least wear a wig, put on heels, put on a dress or some lingerie and, you know, let's hang out.
My last question I keep forgetting to ask.
So, you know, I'm assuming while you're dressed up with this woman, you were having sex with her dressed.
Not fully.
Never had sex fully dressed up.
Okay.
Fully dressed up?
No.
Partially dressed up, yes.
So like in your lingerie or whatever?
Yeah.
Okay.
She says, I don't know.
Is it something when you're fully dressed up?
I can't.
She's different.
Okay.
So she hasn't crossed that.
For her, it's a, it's a stopping point.
So she hasn't been able to get past that point.
That's okay.
But she was down for you being dressed in your lingerie or your panties or whatever.
Yeah.
Okay, cool.
Yep.
Now, did you ever, did she ever think to herself or bring up after she realized she wanted to get back with chicks like that?
Maybe you being dressed up like feminine was a way of her getting in touch with that part of herself, of the fact that she liked or wanted at least and had some curiosity about being with a woman?
maybe that was a part of why she was helping you with that.
Oh, I'm so going to ask her that.
Yeah.
I've never.
And I don't think it ever came up.
Yeah, I wonder if you helped her to listen.
As much as she helped you me,
but you helped her.
I could make a comment once.
Yeah.
Because I was like, you like women.
Yeah.
But I'm full of yourself as a woman.
Yeah.
And she's like, yeah, but I gave birth to you.
I'm the one that created and built and, you know, made that possible.
She's like, it's different.
So, but maybe it was something in the back of her head thinking about it.
Maybe it touched upon and made her remember and gave her the sort of green light to go and
really be who she was.
She helped you.
Yeah, and I'm super proud of her now and happy for her.
And she's, you're going to, you're next.
She says, I went and did it.
So you need to go.
We need to find you somebody that you can do this.
But what I think is, what I think is comparable to her.
And what I think you both did at the same time was learn to fully accept who you are.
You as a cross-chester out and proud, passable, out there doing stuff.
She helped you with that.
And at the same time, she came to terms with the fact that she was maybe gay and wanted to go and or maybe bisexual and wanted to have a real relationship with a woman.
And that's what she's doing.
So I feel like you guys both sort of realized that and you both were probably like a catalyst to that happening in
each other for each other and i think that that's wonderful definitely and we we've still taught i still want to
go and do like a cruise and go the entire time dressed up yeah yeah Halloween you know that would be
that'd be a lot of fun and it's maybe that because she's asking she's like would you want to live
the rest of your life as a woman yeah what is the answer yes part of me is no having a kid
and there's a lot of things you got to answer to yeah my ex-wife found out about it she even tried
bring it up in court and the judge didn't say shit.
How did your ex-wife find out?
I forget how she found.
She kind of knew that I was like that.
And I think it's something.
Yeah.
Oh, I finally tried it because we were still amicable.
Yeah.
And then she completely changed.
She tried to use it against you in court?
She tried to use it against me in court.
And the judge didn't, he didn't even touch it because it's what you do on your own
personal time.
It doesn't matter.
Exactly.
It's not.
I don't think there's any legal ramifications for that.
Terrible.
But I think if I, it sounds great.
I would love, I mean, currently right now, my nails are painted.
I got eyelashes on.
And I'm just as a guy.
Yeah.
And I'm probably going to run into people today and I just don't give a shit.
So.
So you're getting there.
Interesting.
Well, do me a favor.
I'd love to see picks of you for my Patreon.
When this airs, whether it airs on my Patreon or my podcast, I will, I could post,
picks of you dressed up for my Patreon.
Yeah, I do definitely have something I can send over.
All right, send me those and I'll put them up.
I love your story.
I love your girl.
If she ever wants to maybe come on.
I think she maybe has an interesting story.
But I will let you know when this airs.
I'll give you also free access to my Discord.
There's a whole cross-dressing channel on there.
You could go in and make sure you listen to Michael's episode.
I'll send you a pick of Michael dressed up.
You'll be fucking impressed, okay?
and you, after you listen, if you're like, oh, Kathy, I would love to hang out and go out with this person because that's what he's looking for. Let me know, okay?
Yeah, because having somebody to, I think the biggest thing, a lot of guys that start enjoying a cross dressing, and if you have nobody to go out with, you feel just so alone.
That's exactly true.
And scared.
Yeah.
And having a group, and if you're in a group type setting, then people weren't really going to,
Especially you got to go to the right places.
You're not going to go to the jock bar.
You've got to go to the right.
Of course.
Right places.
Palm Springs is really close for us, even from Vegas.
And it's a great place.
It's a very openly gay, tolerant type place.
It's been out there with partial nails and lipstick and eyeliner and eyelashes as a guy.
And nobody cares.
Nobody says anything.
So it's a good place for guys that are getting into it to enjoy and not feel judged, I would say.
Well, listen.
I have found you your best friend, okay?
I forget if he's in Vegas or I think he's in Vegas, but he loves to dress.
He's so passable, like I said.
And when you see, I think it was Michael or maybe I talked to him and I haven't aired it yet.
I'm going to look into it and find who that person is that wants to go out.
I do think, like you said, and the same thing as this person said, too, that I spoke with,
that going out with somebody else dressed would really be ideal.
He also does like to hook up with guys when they're dressed, by the way, so I don't
I don't know if there's anything like that going on.
He's cool.
And I'm going to put you in touch.
I'll find out who it is and I'll email you, okay?
Send me the pictures.
Yeah, and I'll email over some pictures for you.
All right.
Awesome.
Thanks so much for calling in.
I loved your story.
Super interesting.
Thank you.
Thanks, Tiffany.
Thank you.
How a great day.
You too.
Bye.
Bye.
Bye.
Good news.
Strictly Anonymous podcast is looking for people to call into the show.
So if you lead an interesting, naughty secret life that you want to talk about while
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If you're out and proud, that's cool.
to send me an email, strictly anonymous podcast at gmail.com. That's strictly anonymous podcast
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If you have a short confession that you want to get off your back, call my confessions hotline.
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The links and everything else I spoke about
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Thanks so much for listening.
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 audiobook.
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 audio book 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, 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.
then 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 could post your
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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
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Send it to me at Strictly Anonymous Podcast at gmail.com.
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