Strictly Anonymous Confessions - 257 - Eddie is a Crossdresser
Episode Date: November 12, 2018Eddie calls in to talk all about his secret life as a cross dresser. How did he go from a pantyhose fetish to full on cross dressing? How did he learn how to look good while dressed as a woman? When d...id he start hooking up with other cross dressers and what does he like to do with them? Tune in for all the details which include the threesome he had during his first encounter, details about a couple of his other hot hook ups, how he feels about dating women and what does he like to do with them and a whole lot more. **To see anonymous pics of my female guests + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: https://www.patreon.com/StrictlyAnonymousPodcast and when you join, I'll throw in a complimentary link to my private Discord! 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 confesss 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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Welcome to the Strictly Anonymous Podcast.
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Today I have on a guy named Eddie.
His name is Eddie.
That's his guy name.
And when he dresses up like a check, he's a cross-dresser.
His name is Rissa, which I think is kind of a hot name.
You don't like the name Rissa, right?
I think it's Rissa.
Maybe now I'm wrong.
But anyway, Eddie is a cross-dress.
dresser in secret. This is a total
secret life that he has. He said he
dresses up like in Halloween and shit
you know, like full on.
But besides that
day of the year, nobody else knows that
he does that a lot of
the time as well behind closed doors
with other cross-dressers. It makes
you think, right, like how many other people
that we know, other guys that we know
that are really into dressing up as a chick
on Halloween are, you know, really into
that all the time. I think we
always kind of think that, right? So maybe there's
truth to that. I don't know. But Eddie
talks about that. He actually started out
with that Paniho's fetish, and
it sort of snowballed into the whole
shebang. Like I said, he's a cross-dresser, so at this point
he dresses up like a woman. He talks
about how good he looks as a woman.
And he hooks up with other cross-dressers, and he talks
all about that. Where does he meet those cross-dressers?
What does he do with them? Where does he meet
them? That's what he
explains.
What else do we talk about?
All that good stuff.
It was always interesting to me is what people sort of label themselves out, right?
As I don't know if you listen to my podcast before,
you always hear guys that don't think that they're by or anything,
even though they like suck dick.
This guy, we talk about that too.
But anyway, so I'm just going to be right back on with Eddie.
How are you doing today?
I'm doing good.
How are you doing, Gabby?
I'm doing good.
So you're another panty hose guy, but you took a panty hose to a place that I have always asked people about because I could see it being connected, though it's not always typically connected, right?
I mean, and we're going to get to all the details of it, but the fact is that you started like with a panty hose fetish, and now you're like a total cross-dresser.
Like you dress up in high heels, clothes, make up the whole nine yards, right?
And that's like your thing.
Yeah, the whole nine hours.
I look totally like a female when I'm all dressed up.
But yeah, it did start for me with panty holes.
You know, a lot of the guys that I listen to most of your podcasts,
the panio guys were on.
And you would say, like, is it a gateway?
For me, it kind of was.
Like, obviously I started with, it was just me and my mom.
So I started wearing hers at a young age.
And like, that's what I first noticed, I think was like elementary school.
Like, it was dumb as it sounds.
I had this one teacher.
And she was white, but I noticed one day her legs were black.
And that was just like,
And it's like, what, six?
Yeah, six or seven.
Were you like, what the fuck?
Or so curious.
Yeah, and I guess that's what the trigger of it, I guess.
I mean, my mom always wore two, not that I was ever into my mom or anything like that.
But that's the first time I remember noticing.
And then always from there, I kind of looked out and eventually found out what tights and pantyhows were and everything.
But that's the first time I really remember, you know, noticing them.
You know, obviously I love the feel.
Yeah, that's what I was going to ask.
You had all that stuff going on.
too, right? Yeah, like all the other guys you had. I know a lot of guys you had were really into
like the nude or suntan color. That's like your main thing. For me, not so much. I prefer black
the most. That's my favorite. Right. I mean, not that I don't like the other colors too. I like
all colors, you know, like there are guys I know, you know, control top and shirt waist and
European brands and all that. Yeah, that all rang true for you like you, right? Oh yeah. Like listening
to them, for the most part, I agree with
the, you know, what they would say about, you know, it's like my mom be at work and I'd sneak
home from school and just try and like take a pair and put them on and, you know, fill my
legs and everything. Like even when I'd even know what masturbation was yet.
Right. Like before it was even a sexual thing, right? That's what was interesting to me that,
like, it started out as like a tactile. Is that like the right word for it, right thing? Like it's like
the feel and the touch and you're curious about it and you just like it. Maybe it's soothing,
whatever, but it wasn't so much a sexual thing at first.
right that's what was interesting for me to hear from some guys yeah not at first because you know
when you're like seven or eight you don't even have that you know yeah yeah yeah you never know what sex
is yeah yeah yeah you just put them on and feel them like oh this feels really good and i like you know
you don't know anything you know eventually i would like lay on the bed with him and help it and like
first time i ever had orgasm was in a pair of panic it was actually so right right eventually it turns
sexual yeah yeah and then you find out you're like oh my god so um right that's what it was all
about and so you were into the black and so you were into the black and so you're
your mom ever catch you like early on was there any kind of stuff i don't know why i always
no question yeah no it's okay i was always very careful you know if i put them on and i'd wear
him i try and put them back exactly how i found him because i didn't want to be caught or anything
like that that wasn't i know some people have a turn on for that not not for me you know that would be
the end of the world so yeah so let me ask you this because you're like full-on cross-dresser
now right yeah and you say you like taking pictures and stuff like that and posting them
putting them out there.
Like, do, is this a secret life that you have or no?
Like, you're totally out and open about it.
Well, it's, it's more secretive, but I mean, I do have,
I don't have you heard of the website, FetLife.
Yeah, uh-huh.
Yeah, yeah, yeah.
You know, it's like, that's how I post pictures on there.
And at first I wasn't posted my face because I was like,
I don't want, you know, any connection, like my friends or anything.
But then I was like, you know, I ask, ah, I'll just post one.
And, like, you know, I do look pretty hot dressed up.
I will, I mean, not to brag, but I look pretty good.
I'm not like a big burly guy.
Like, I'm in good shape.
and everything, and I know how to do makeup, so I don't look like a freak.
Yeah, yeah.
So, you know, a lot of people, but when you look really good, you look hot, so it kind of, you know, fuels you to take more pictures.
But, yeah, so I don't, but I'm not like, I don't, like, want to transition or have sex change or anything.
No, but let me ask you this.
Does your family and friends know that you do this, or do they just know, like, Eddie and Guy Close?
Well, I do, like, for Halloween.
Like, I, I, like, I've been on Halloween.
You know what I mean, like, to the, you know, yeah, yeah, but this is a thing.
Yeah, but that's what I'm saying.
No, not as like just to go out and go shopping or anything.
But like Halloween, I dress up and they know that I dress up like as different characters like a viral and stuff like that.
But other than that, nobody knows about, you know, that I dress up fully like a woman.
And then, of course, meet up with our cross dressers, you know.
Right, right, right.
Yeah, we'll get to that because you like that's like that's like you have sex with them.
Like that's like your thing.
Are you in a relationship or anything like that leading a double life or are you single and just like having your fun?
No, no, I'm single.
No, I'm just having fun.
I'm like 35.
So, you know.
Okay.
So let's get back to when you were little.
So you're taking the panties.
Eventually it turns into like a sexual thing, right?
When do you start to sort of say, oh, like maybe I'll wear high heels and then let me take my mom's dress.
Like, is that how it starts?
Like how to, like, when does that happen?
Yeah, probably like, I don't know.
I'd say around like still pretty young, 10 or 11, you know.
You know, obviously I wasn't seen no girls dressed up in school, but like, you know, TV and stuff.
So I remember like seeing a lacy black brawl and I really like that.
So I was like, well, why not I try that all, you know?
Yeah.
A lot of times are just panty hose and a bra and then like a nighty or a dress.
But, you know, stuff, I was little so it didn't really fit me that well.
Yeah.
And then I remember, like, her heels never really fit me because I feet really is too big.
So I couldn't wear heels for a while.
So I eventually bought my own.
But that's what really kind of started it was like, you know, I'd see I seen the bra and it's like, this was really sexy.
I'm going to wear this too.
So that kind of, you know, connected it all.
Eventually, I would buy my own stuff, obviously.
But like, yeah, but that's kind of ballsy to be buying your own stuff.
It's like, what are you going into the store and saying?
Like, oh, I buy for my sister, my girlfriend.
Well, yeah, I would try to never bite in the store unless, like, you know,
you're buying a couple of different things and you can kind of hide it.
But, like, I did it down.
Thank God for the Internet and ordering stuff on there.
Oh, yeah, you're right, right.
You're just buying Amazon.
Yeah, when I was still with my mom, that was my main place to buy things.
I go on the Internet and, you know, order panty hose or a dress or heels.
You know, I finally got a first pair of heels.
Like, obviously, they were too big because I didn't understand the sizing ratio.
Yeah.
But I finally did get it to them.
And I was like, wow, this is super hot.
So, I mean.
Was there a lot of, like, inner turmoil for you at all?
Like, were you, like, am I gay?
Am I straight?
Am I trans?
Like, do I want to be a woman?
Or, like, was it, like, clear to you?
Like, did it freak you out at all?
Like, the fact that you were into this stuff?
And, you know, like, a little bit at first.
Because, like, you know, you think you're obviously the only person in the world.
Yeah.
I'm doing this.
But I never thought about, you know, that I wanted to be.
I think it's cool to like kind of dress this girl and like you know like one but like I don't have a need to be you know a female and uh you know I didn't think about being uh you know gay or anything like I don't consider myself gay like I love women I love having sex of women you know but I also like having sex with cross-shirts too so at the most buy I guess you get certain I'm not into regular guys at all or anything right like you wouldn't be into like a hairy burly male male man no no I could get money if uh you know I couldn't get harder of money was involved but if a burly hair
Mary manly man was dressed up as a chick, right, with the high heels and the panties.
And he still's got his dick and the hairy body, all that stuff going on.
You could still get down with that guy, right?
Not so much if they were like hair.
They have to be somewhat feminine.
Like I try to like when I do meet with her across dress, it's like I want them to be as feminine as possible.
Like I understand.
But like I don't like, like I don't have any leg hair or body hair or anything.
So I try to want them to be smooth and like, you know, it's.
It's feminine looking as possible, I guess you could say.
Yeah.
And but let me ask you this.
How far do you go with them?
Like, because they obviously have dicks, right?
So I don't know if, like, you stop there and that ruins it for you, like, because you want to really sort of pretend that they're female or like, do you, like, do oral and all that kind of stuff?
Yes.
Okay.
Everything.
So, so one of the turn on for me is a chick with a dick.
So that, to me, is, like, super hot.
Right.
So, um.
So that's what that is for you.
Right.
Yeah, yeah.
So like when I like they lift up their dress and like a big hard dick under a panty hose like that's super turn on for me.
So like but I'm not into like anything else masculine, which is weird.
Like I don't like body hair.
I don't like big jack guys or anything like that.
Trannies.
Yeah.
Yeah.
Yeah.
Yeah.
I haven't.
I haven't met any like I live in a really smaller town.
So I mean, it's not like it's in New York City where I can just go out and find a tranny.
But I would love to.
I think that would be, you know.
What about that life?
Where do you meet your people that you hook up with the other cross-trizzles?
like it on fat life and people that are close and like to where you live yeah some are so on fat
life I mean it was Craigslist now that's gone obviously now there's double list I don't know if
you heard of that no I could go there to get gas I mean I have so many people email me I don't
really need to but so there's a thing called double list and that's like the new Craigslist yeah it's
basically the same but it's not as spread out so like whereas like Craigslist had like 20 cities
double list might have like three per state you know so it's a little more but I just found that
actually like two weeks ago, but I used to go on a panty hose message boards.
That's where it all started.
And there was people talking about paint holes.
That's where I started like taking pictures of myself and post them.
And it was just started like just my legs.
Yeah.
And then until I started, you know, getting more dresses.
Of course, people are like, oh, you look really good.
You look hot.
So I talked to some people on there.
And then they would like, there was a threat one time about Yahoo Instant Messenger when that was the thing.
Yeah, yeah, yeah.
So I got that.
Somehow there was a first thing.
I met with their cross-dresses.
One lived like half an hour from me, and we were talking on there.
And, you know, at first I was really nervous, and I didn't really, I didn't know if I wanted to do or not.
Because I don't know about, you know, being gay or whatever.
Yeah.
And, you know, but she was really nice and really cool.
So the more we talked, then she invited me one time, I was like, nah, I don't think I can.
She's like, we'll just come up and hang out.
And then the next time when she asked me up, I was like, you know what?
I'm just going to do it because, like, I would look online about pictures, like, about, you know, guys dressed up.
Like, first it was like men and pantos.
but I wasn't really super into that.
Like, I wanted to look more feminine.
Yeah.
So, like, the crosshers of pictures really turning me on.
So that's why, you know, I was like, well, I really want to try this.
So the hell with it.
I'm just going to do it.
And the first time I met with her, she actually had an other friend that was crosshairs.
And they were full and they had, like, hair and nails and everything.
And at that point, I didn't have too much yet.
So there was two of them there at the house when you showed up.
Yes.
Okay, cool.
Yeah.
Yeah.
So the first time that I ever met with any other crosssters, it was two of them.
And, you know, I was now super nervous and everything.
And, you know, I got, we got there and they were already, it was a hotel room.
So they were already full on, you know, dressed up.
Yeah.
So I got there as the guy.
And then I went in the bathroom, I changed.
And, you know, a little nervous at first, but it was like, no, this is like such a turn on for me.
Yeah.
And that was the first time I'd ever do anything with like a guy, but like, like, like, I don't like to say, yeah, yeah.
What happens?
Um, what, what we did you do everything?
Not, not at first.
Like, that was very, um, nervous and everything.
So, like, we just, like, I came out and they were like, oh, you look great and everything.
I look so are you.
And, you know, like, fill each other's legs.
I was because they were both super into panicos, too, which a lot of cross-dressers are.
Right.
So, like, that's a start for a lot of them.
But, you know, we fell each other up.
And then, before I know, like, they were both blown me.
I'm like, well, this is pretty cool.
Yeah.
Right.
Yeah.
So that's all we did that time was just, we just blew each other.
Like, the first time I ever sucked a dick.
And I was like, because I was always kind of curious about that, too.
You are.
Yeah.
Yeah.
I would say you're by.
But like I just don't like regular guys.
Yeah, yeah, yeah, yeah, definitely.
Everyone's unique like that.
Yeah, so, yeah, we just, we just blew each other that time.
And that's basically it for that first time, that first meeting.
And did they give you, like, tips of the trade?
Like, because you said they were, like, really done up there, the nails and you weren't, like, didn't have all that yet.
Did they, like, help you sort of, you know, up your game?
Yeah, a little bit.
I mean, they gave me, like, you know, a little bit of tips and stuff, like, dress.
sizes and stuff and I knew some because I'd search
on the internet. Because I really wonder like where you learn how
did you make up where you figure
out how to do the, I mean, did you get
a lot of advice on that forum? Or is it
just like Google and the internet?
Some was the forum like I remember
there was a Pany Ho's and there was another
Pany Ho's discussion. There's an ever website called the Lake Song
that was kind of like Facebook for
Pany Ho's fetishist but
it doesn't exist anymore. But there
and I was searching Google and like
just trying like conversion of like
women's heels to like men's sizes.
And they always say like two sizes, like two sizes up for your men's size and women's is your size.
Oh, interesting.
Right.
Yeah, yeah.
So if you have a 10 in men's, you would take a 12 women's.
But like, luckily you have small feet.
So I only need to 10 women's.
So I can find heels pretty easy.
So I figured that all out.
Then like I would watch YouTube for makeup tutorials.
And that's how I learned to do makeup.
And I'm actually pretty good.
Yeah, you're probably better than I am.
I've never watched a makeup tutorial.
Yeah.
So yeah, like foundation.
I can do eye shadow all kinds of crazy things.
And I don't like to do like real drag.
egg heavy makeup. I like to do more of like kind of like an everyday makeup,
but maybe just a little bit more like, let's say like going out for New Year's Eve
makeup. That makes sense. Right, right, right, right. But wait, so you're, when you're,
when you met those guys, the two guys or girls, you call them, right? What? Yeah, how old were you
around your first experience? Jeez, it was probably about like 10 years ago. So like,
probably around like. Now were you out of the house at that point and living in an apartment or like
were you still not yet, no. So was your shit like, where did you have?
all this stuff like I didn't have too much but like my I had like my my my bedroom they also had like
a little room in the basement so like I would hide stuff in there like the closet like my my I had a couple
pairs of heels and like I would stuff like I would stuff like I had and you know bra and stuff so I kind of
hit it there like that's what one of the big things about moving out it's like hey I can dress up whenever
I want yeah yeah yeah right you don't have to hide everything in or so but like what was going on like
with the straight part of you like you know the guy part of you like were you dating did you lose your
virginity yet? Did you fool around with guys before you fooled around with girls? Like, what was going on with
women? Yeah. Well, I mean, like I do, I love women. So I think that it was pretty late on. Like,
I would date a girl here or there when I was younger, like 14 or so, you know, nothing serious.
Yeah. And I didn't think the first time I had sex was probably like 19 or 20. So I was a little bit
there. But, you know, I did love it, obviously. You know. But do you have any girlfriends?
Long-term girlfriends? Not really. Here and there a little bit, but nothing like long-term.
Right. Okay. So it wasn't like you had to really hide it. Did you ever confess to any of the girls like that you were really into Panty House? Because that's not easy. That's easy to say, I think. Yeah, but I mean, it was always kind of hard. Like I would just say it's a girl that like, well, what are you into? I like, well, I like stockings, you know, because they think that's a little more acceptable. I do like them. I do like them. But I would say that. Like I got a couple girls to wear stockings for me, but like never. Only one did I wear two. And I mean, that was kind of hot.
And I just said, well, if we both wore, you know?
Like, she's like, oh, okay.
I don't know if she was like really into it, maybe into it because I was.
But, you know, other than that, I mean, and then I did, when I was dating one girl, like, I've never, if I haven't dated a girl, I don't meet up with other cross-dressers.
Like, you know, I just stayed at one girl.
Right, right, right.
Like, like, faithful to her.
Right.
Yeah, yeah.
Because I don't, I feel bad.
Yeah.
You know, I wouldn't want to do that.
So, like, all the times when I hooked up with other cross-dressers or CDs, as I've been single.
so uh what is your ultimate though like say because you're single now and everything right and
yeah like say 10 years like you know in the future when you want to sort maybe settle down
somebody or be with someone what does that person look like for you is that is it a woman is it a
cross-dresser like what do you what would be ideal for you um as far as like a long-term partner
yeah like i have no like uh like i have no desire to date a guy or a cross-dresser like i would
one that, like, only have, like, emotions for women, if that makes sense.
Yeah, yeah, yeah.
So, you know, like, I'm not really, like, really into relationships.
It makes sense.
Like, they're all right.
But, like, I've never, I've never been one to be like, oh, I'm so, you know, I'm alone.
Lonely, right.
Yeah, yeah, I don't really get lonely.
I'm always, I have tons of hobbies and friends and stuff.
So, like, like, if something comes along, I'm not against it, but I'm not like,
I have to, you know, meet someone and get married.
But, like, I would, I would, if I was, I would want to be with a woman.
And obviously, I would like her and be into cross-dressing.
Right, and maybe you would, well, you wouldn't be with a man that's a cross-dresser, right?
You would want to be with a woman that was open to you cross-dressing, right?
Because you wouldn't be able to live a double life.
You're not into that, right?
So it would have to be somebody who's sort of like open to it and someone because you would be honest about it.
Yeah, yeah, I'd rather, right?
I don't want to, like, go behind someone's back and be like hooking up with cross-dressers and then my coming home to my girlfriend.
I don't want to do that, you know?
Right.
I want her to be like, to know about it and be into me dressing up.
But maybe having a threesome, you know, that'll be.
Right, with the guy, with the cross-dresser, right?
Yes.
So you would be open, but you've never, nobody in your life besides the cross-dressers that you've met online,
and now me and all of my listeners, know about this whole thing, right?
You've never told any of them.
Like, they know, like, hey, he dressed up for Halloween, blah, blah, blah,
but they don't know, like, I dress up and meet with other cross-dressers and have sex with them.
You know, my God, no.
So after those two guys, right, the two cross, well, the two,
girls, right? And you did that. Yeah. Was it like amazing? Like, because you said, you had thought
kind of about like sucking a dick, right? But now there you were actually doing it. I guess you
suck two dicks that time, right? Yeah, I did. So my first day was two different ones. And, you know,
it was nice. They weren't real big. Because I don't want, I'm not into like a real big, huge
horsecock or anything. Yeah. Yeah. But I did like it. And then a little bit, you know,
afterwards, you kind of feel like a little guilty and like, you know, it's like anything sexual at
first. You're like, I don't, you know, I don't know. But I'm like, you know, my mind is
Did I just do?
Yeah, kind of.
But then I'm like, you know, I liked it.
It's not hurt me.
It's not hurting anybody else.
You know, I'm not like cheating on anybody.
So, man, what does it matter?
Hell of fuck it.
I'm into it.
I'm into it.
Yeah.
So, I mean, you know, and then like, after that, like, they got home and I was like,
well, that was pretty hot.
And I was like, well, maybe I'll go do it again, you know.
And I did meet up with the one girl a couple more times.
Like some crosshressers I meet up with a couple times.
Some is just once and done.
You never hear from them again because like, it's weird.
Like a lot of cross-dressers are like real neurotic or crazy or something.
That's what I think like, I'm pretty normal.
I just like to dress up like a girl.
Yeah.
Yeah, yeah.
But what do they say?
What do people think?
What?
What did you just say that people think that they're psychotic?
Well, a lot of cross-dresses are like crazy and neurotic, not psychotic.
Oh, really?
Yeah, like when I, like, I would post it out in Craigslist when I was around.
And I wouldn't show my head.
So just like from like my neck down.
Yeah.
And, you know, saying I went to me with neurocrossed or bowl.
blah, and, you know, a lot of times you get, like, really weird responses or, like, they want to meet up, like, immediately.
And it's like, I can't meet up, like, in an hour.
You know, I was like, because I would, you know, put out, like, let's, you know, talk and separate day.
But, like, it's just, it's weird that a lot of cross-hers are just really out there and hard to deal with.
So that's why I don't meet up with so many because it is hard to find, like, saying ones.
Oh, interesting.
Did you stay in touch with the two of them?
Yeah, yeah.
I'm actually friends with them both on, on Fat Life.
And, uh, I met up.
with them both about a couple months ago back in, I think it was May or so, and it's pretty hot.
Oh, wow.
So that's like 10 years later.
Yeah, yeah.
Still talking to them and still meet up with them occasionally.
Like I don't, I would say like every couple months I meet up with their.
So you've been doing that ever for the past 10 years.
It's not like out of the blue you met up with them again.
No, no, no, off and on.
Oh, okay, cool.
Whenever, whenever our schedules and we have time, you know, to meet up.
Like, I think the one is married.
So, like, I kind of feel weird about that.
I'm like, well, you know.
That's his problem.
Yeah, yeah.
It's not my problem.
Like, I'm not married.
Does his wife now?
I would say no.
Right.
You don't know.
Yeah, I don't know.
It's true.
But yeah, them two, they weren't into anything other than just kind of blowing each other and feeling each other and making out.
Like at first I didn't make out with their cross-stressers, but then like kind of got into it.
And it's pretty hot.
As long as they're like sexy looking, you know?
Yeah.
Kissing can be hot.
And I, but I get people so that sometimes it's like, you know, some people with kissing, it's just like,
like, you know, they won't do it with everybody.
It's more intimate or something, you know, but I think it could be very sexual, right?
Kissing.
Yeah, definitely, yeah.
Like, especially if you're, like, turned on and just turned you on more.
Yeah, totally.
I really like making out.
Yeah.
I think it's great.
So after that first experience, like, because obviously you say you've done everything
with the cross-dressers.
So obviously you sort of did more and more.
Like, what was your second experience after the two guys, the two cross-dressers,
the two women?
Should I be calling them women, right?
Because you're calling them she's, like, right?
I usually do just of like default.
I don't know if it makes you feel better about or whatever, but like, you know, not that I'm, you know, yes, I like second dick and getting fucked.
But, you know, maybe that's what they would prefer.
Like maybe it's because you, if you were them and when you're dressed up, you want to be a she, right?
That you're sort of, it's like a projection.
Like you think that's what you would want to be called, right?
Because that's what you're going for.
Yeah, like when I'm all dressed up, like I even have a girl name and everything.
What is your girl name?
Rissa, like Marissa, but just Rissa.
Rissa.
I got it from a girl.
that I liked in high school. Thank you. I like Rissa. Rissa. She sounds kind of slutty.
Yeah. It sounds like hot. So it's a good name, you know.
Hot and slutty. I remember I had one from a long time ago at cross-dresser. It might not be like it's hard to find. I have like, you know, 250 something episodes, right? I've been doing this for four years. And there's one that was, I forget what her name was and she's far back. I did her many years ago. But she was, she was a cross-dresser a couple times. And she was really into being slutty. Like that was her thing.
She'd love to be like our super slutty girl.
Yeah.
Some do.
Like they want to be like,
some want to be like total horrors.
Yeah.
Some want to be like the sissy thing, which I'm not,
I'm not into that at all.
Like they want to dress by a little girl and kind of be like insulted and every like,
that's just not for me at all.
And then some of like ruined the bondage.
Someone,
it's weird.
It's like,
it's kind of like you're a cross resort,
but you also have like a secondary fetish as well.
Yeah.
It's like regular people.
That's just the way that it goes.
Right.
It's just like that's a second thing that adds on top of it, right?
For sure.
Yes.
So like for me.
It's just like prostressing and pantyhoes and heels, I guess you can say.
But like other than that, I'm not into anything else like that.
But I think the first time that I met up and got fucked was probably maybe a year or so after I met those two.
I think it was like I used adult friend finder at the time.
Yeah, I used to go on there to look for guests too.
I know all about that place.
Yeah.
Because Craigslist was like I would go to Craigslist and then I'm like sometimes like Craigslist I wouldn't get people.
So I would have to like really work hard to get guests in the beginning.
inning. So I was on
I got a couple of people from adult friend finders.
Oh, okay, yeah. So then you know.
I know about it. Yeah, for sure. Yeah. So I used that and I was talking
this one CD. She lived
about about an hour for me, but we were talking about four, she sent some
pictures, she looked pretty hot. And I said, like, what are you into? And like,
she said, you know, fucking getting fucked. I'm like,
and I wanted to try it. And of course, I bought a dildo. And like,
I didn't know what I was doing first, but like I just really wanted to try it.
So I tried that myself. I was, well, this is kind of, you know,
I kind of like this. So,
You know, I did have some practice rather than I just show up and like take a dick in the ass right away.
Yeah, yeah.
But, yeah, I met up with her and she was really, like you said about making out to be hot.
Like she was super into like, like, for play and making out and everything, which I'm like, this is cool, you know.
Yeah.
And I think I fucked her first.
And I'm kind of big.
Like, not the brag.
So like sometimes it's hard to fuck them because they don't, you know, it's a lot to take at first.
Yeah.
But I mean, look, you said you don't like a big dick.
No, I don't.
I don't.
I like a nice, like, average size.
I don't want a big one.
Right.
I'm kind of big like like seven and a half and then thick so it's it's kind of hard for some girls
um even real girls yeah but uh yeah so i fucked her first and then we were messing around and like
that was the first time i got fucked and i think i was like i think i was in i bent over first
and like at first i was like ah but then like after a while it felt really good and i really do like
getting fucked so like that was pretty awesome that first time like i think i was riding her and
I came right of her.
And then do you like, you like doing it as well.
So you're like a top bottom, both.
Yeah, yeah.
Yeah, for versatile, as they say, like, I think I would have anything more top than bottom.
But like, not that I don't, I do love getting fucked, but I think I like to fuck a little bit more.
Right.
And you use condoms, right?
Yes, yes.
Yeah, because, you know, you never know, you know, especially when you're talking to someone,
you don't really know, you kind of know them, but not really.
So, you know, you won't be safe.
Yeah, no, totally.
It's smart to do.
Only because, like, the whole AIDS thing with guys that.
It's not because, like, I think people never really sort of understood why it was more prevalent in the gay community,
but it's just because of the nature of the kind of sex they have, right?
It's anal sex.
So it's like a woman.
It's the same thing with the woman.
It's just such a tight sort of place that you could get like little cuts in there and then the transfer of the sort of stuff could happen.
You know, it happens more there because it's such a small area, right?
Yeah.
So that's where you have to just be more careful is whether you're with a woman or a man.
You're anal sex.
It's what is the problem or the thing that could be dangerous.
Yeah, I mean, it's tag in, and you need loob, and you kind of got to work your way in and stuff first.
But, yeah, that's, like, where you just said it is a little more dangerous.
And probably because more, like, gay guys more are more open to having sex, so they're doing it more.
So that's why it's by the AIDS and stuff, you know, why it was more prevalent.
But, uh, I'm very, very clear of what they're doing.
It's like they have anal sex.
You know what I mean?
In anal sex, you could get tears from it because it is a different kind of entry place.
You know what I mean?
It's not like a vagina.
You know, like, it's not, you don't get, like, little cuts in there.
It's different, you know?
That's why I think for women, it was a little lot.
Not that women can't get it, women have, you know.
But with guys, that's why guys should be very protective when they're having sex with other guys, because that's, it's, because it's what they're doing.
Yeah.
Yeah, especially.
It's just taking a big old cock, you know, yeah.
Yeah, for sure, right?
So that was your, so, and then, so you realize you like that, too.
Yeah, like when I went up with her and she didn't have a real sex.
And she didn't have her big dick, which was good because I didn't want to, especially the first time I didn't want a huge one.
So it felt really good.
I liked it, you know, a couple different positions and stuff.
And I was like, well, I like this.
But I also like fucking.
So like, meeting up with other cross dressers like, like, it's probably going to be hard to find a girl that will like wear a strap on and fuck me.
Like I'm sure it's out there.
But like, yeah.
Yeah.
Yeah.
Yeah.
But you have to get a girl like, listen, you're 35, right?
What age range do you date girls?
Like what kind of, what age girls do you typically?
I try to stay within like, you know, within five either up or down.
years, you know. Right. So 30. If you go into your 20s, you'd probably be find more open, you know,
I think women are pretty more open than when I was growing up, please. Like, it's a very different
world out there. Like, I was like considered like really slutty because I like sex and fucked
around. Like, you know, because nobody did. It wasn't really common when I was growing up. Like
most girls were in relationships and that's when they did things. They didn't try other things.
It was just like a different place, time. But now I feel like girls are.
are so much more open-minded and so much more like I was when I was younger.
You know, they're just like doing their thing.
It's a very, you know, so I, and I, and I hear on my show lots of men, and it's more
of the younger ones that are with women that are open to all kinds of things.
Yeah, which, which that would be great.
But, I mean, it is hard to tell a girl, like, what are you into it?
Like, I don't want to tell her.
I want to get fucking ass.
Like, you know.
Yeah.
And also because you don't have, like, long-term relationships.
Do you have, like, at least long-term booty calls?
No, not really.
Yeah, that's the problem.
Yeah, the longest girl I was with was probably like almost a year.
So like, you know, and I never brought up to her because I'm like, well, that's probably going to be like, I always feel like, well, that's going to be the end if I bring it up to her, you know.
And I only actually did dress up with her once, but I did a drag show.
So it was kind of excuse to, you know.
Yeah, but what were you doing a drag show for?
Was it a Halloween or?
No, it was like a local like amateur one.
And like my friend's like, well, you dress up for Halloween.
You should do it.
Now, of course, I was like, oh, yeah, I went.
Right. But did you guys go home and have sex after that?
Yes, we did.
Oh, so that was perfect.
Yeah, that was. Yeah.
Did you ever do that again?
No, we only did that one time.
And then she's like, well, you seem like you really like that.
So she kind of like hell.
Did she be right after or did she keep coming back?
No, no, we still dated for a couple of months.
And I don't think that was what ended the relationship.
So that means she wasn't not into it.
Yeah, I mean, she was, but I was like, I felt like so scared.
to be like I really like that can we do it again like yeah right right yeah you have to ease it in but
it is easier I think you know even if you don't have like full on relationships if you have like
a longer term sort of even just sexual relationships with somebody where you're close enough with
them that over time you could like really talk about things and communicate and after a while
you could like ease into things without coming right out and you know what I mean without it
feeling like you're sort of, that's what you want, you know, you could bring it up casually
over time, you know, but you're not going to do it with a, or, you know, if you don't have like
longer term booty calls, what's the big deal to sort of throw it out there to a one-time person?
Like, who cares?
Maybe they'll go for it.
Yeah, yes.
And then it'll be, I mean, they do.
Great.
And if not, it doesn't matter.
You're not losing anything because it's like a one-time thing, right?
I'm talking about with the women, you know, like to find a woman that wants a fucking.
you in the ass, you know.
Oh, yeah, definitely.
So, yeah, I mean, you're right.
I mean, I just always been so, like, I can't mention it to him because they'll just,
like, you know, let's never, they'll tell everybody, you know, it's embarrass me.
That's what in my mind, you know, probably one half a minute, just probably like, no, but
that's what I think.
So.
Yeah, it's hard.
Well, if there are people, no, listen, if it's somebody like in your town bar where
you go and she knows everybody, I wouldn't say throw it out there because if she's not
into it, she might tell everybody and you know that exactly what you just
that. But if it's like a girl that you meet, you're away or like, you know, and it's not
somebody that would ever, anything would ever get back, you know, why don't you try it?
But it's like the type of thing where then you have to have a strap on ready for them to do it.
Do you know what I mean?
Yeah. That's not really something to carry with you.
I just think that you can, you know, if that's what you were looking for, it's not that
you could maybe find that. You need a freakier girl, you know?
Yeah.
And they're out there.
Because like a lot of the girls I've been with have been more.
more, I guess you could say, traditional.
They didn't want to do too much because I don't want someone to think I'm a whore.
It's like, well, who's going to know?
And first off, you're already having sex.
That's because you're going for 35-year-olds.
If you go for 25-year-olds, you might find a different scene.
Yeah, well, I mean, I'm open.
Not like I can't date anyone, you know, below 30.
Yeah, yeah.
I'm open, but, you know.
But are, I don't really.
Who do you have sex with more, do you say, like cross-dressers or females?
Now, now it will be cross-dressers just because it is a little,
easier, you know, because I just, you know, fat life and stuff and hey, you want to hook up,
or you know, you can't really just message girls on there. Because most of them, like, if they're
not with someone, then they might be fake. And, you know, yeah, it's, it's much easier for
to have sex with crosshressers. So that's what I mainly do. I mean, not that I don't want
have sex with women. I do, but it's just hard. Well, that's because, first of all, listen,
a lot of girls are looking for relationships, right? Or more. They're not just going to meet you
in a hotel, like those people and you're going to come out of the door and fuck them. You know what
mean like women aren't don't operate like that sexually you know they might need a little bit more
foreplay you have to take them out to dinner you may never talk to them you know yeah yeah and I don't
like don't have the patience I guess because I if I can get this you know right away I just do that
but like yeah yeah and your needs are met like I mean do you ever but like when and what's great
about you is like when you're kind of because you say you love women right like do you love to go down
on women like when you want pussy like quote unquote like I'm not yeah I'm not like you're not like
ew, pussy.
Like, I do e-girls out and everything.
And, like, I love, you know, figuring out of everything and boobs.
And, you know, I do love women.
So it's not like I'm just like, you know, I just like cross-stressers.
It's, you know, I like both.
Right.
You like both.
And you have, but you mostly sleep with crush-dressers.
Like, when was the last time you're with a woman?
It's actually been a really long time.
It's been like two years.
Right.
So, because I was wondering, like, when you have that urge, right?
Yeah.
What do you do?
Is it just that, like, you wish you could be with someone?
or like in the past two years,
but you just can't find someone?
Or is it more like you're just so satisfied
with these cross-dressers that you're fine without it?
Kind of a little bit of both.
Like, I'm satisfied.
Like, I do want to have sex with women too.
But, like, it's because it's a little bit more work to do.
And I'm kind of just like, well, I'll just fuck up with the cross-dresser and that'll
be fine, you know?
Right.
Now, do you your friends?
Like, does anyone, like, pick up on any of this shit?
Like, you know what I mean?
Like, I feel like if I was your friend, right?
I might, but I'm like a real prying kind of person, obviously, that's why I do my show.
You know, I ask a million questions.
So I might be like on you, if you were my guy friend, like, why haven't you fucked someone
in two years?
Like, what's your problem?
You know, like what?
Yeah.
And it might maybe alert me that maybe something else.
You know, I don't know.
Like you're 35, you know, what do people sort of wonder?
You know, probably.
You know, obviously, I don't know what you're thinking.
But like, you know, I mean, my friends have, you know, I've had girlfriends and stuff.
And, you know, I'd be here and there.
So, I mean, if they do, maybe, like, I don't, I don't know if they would put it together and be like, hey, he's like not having sex with any girls.
Yeah, yeah.
You know, if they do, I'm oblivious to it, but, you know, maybe.
Right.
I just wonder if I knew you or, like, what people that know you, if there's any sort of signs besides the fact that you haven't been with a woman, you know, like, if there's any signs or maybe some people might have sort of a thought maybe or an idea that.
maybe you're doing something on the side because of the Halloween, I don't know, like, do you think
that they would be shocked or do you think that they might be somebody might be like, oh yeah,
I kind of thought something was that.
I think that would be a little shocked, but then be like, well, he does like to dress up at
Halloween and stuff.
So, like, I don't think you're really good at it for the Halloween thing.
Yeah, yeah, like I totally look like a virus and one Roman stuff.
So, you know, and I have like fake, fake boobs I wear and stuff.
So, I mean, yeah, I'm pretty good.
Like, I do look really good dressed up.
So I think they'd probably be like, well, shocked at first.
but I'm like, well, it kind of makes sense, you know?
Right.
And you have sisters or brothers?
No, I don't.
I don't have any.
Right.
Okay, so you're the only child.
That's like my son's going to do the way.
So it's not like they would, they...
Yeah, yeah, they would have no idea, obviously, because they don't have any.
But, uh...
Right.
Yeah, it would just be my mom.
So...
And so your mom, is she, like, wishing you would be married because, like, you're the only
child and she wants, like, grandkids, or does she not give a shit?
I, she doesn't care about kids.
And, you know, and, you know, do I?
Like, I don't really want any kids.
that really indicates.
But like, she probably would, like, she always like, well, why didn't you get a girlfriend or
meet a girl or something?
Like, well, I mean, we do live in a smaller area.
So, you know, there's not, it's like, you know, if you know a girl, like everyone you
know, has either been with her boyfriend or married for 10 years.
So, you know.
Right.
And it's not like you meet new people.
When you're on Fat Life, because you said a lot of people, like, hit you up and
like, oh, you look really good.
Like, do you get women ever?
Or is it always mostly other cross dressers and straight guys?
Do you get a lot of straight guys, like, sort of like you?
Yeah, I do.
I do.
And I'm not, I'm not into that.
all like they'll message me.
Like if you're looking for a guy and it's like, well,
one of the first things I have on my profile was not intimate, you know,
right,
but like I get messages from dudes all the time.
Right.
And it's like, no.
And a lot of times a profile picture is just their dick.
And like that's,
that's the total turn off.
Right.
As far as women.
Such a straight guy thing.
Yeah.
Yeah, it is.
Yeah.
Even though I like it, you know, connected.
But I only talk to like two women up there, but they're obviously like,
when you do meet someone, they're like seven states away and it's like never
possible at whatever hook up.
ever so yeah really like they're too far yeah yeah so like I I I did talk to but I did
meet that reminds me I met up with a couple one time oh interesting yeah a couple years
yeah no they were they responded to a Craigslist dad that I had and it was it was the the guy first
obviously he said it was cross-dresser and I was like okay I sent some pictures look pretty good
and then she was like well do you mind if my girlfriend comes I'm like well hell no you know like honestly
I'm not like that so uh we met up with them and
And I mean, she looked pretty good.
Well, the guy looked pretty good dressed up.
And then the wife was like, her girlfriend was super hot.
But like, they didn't really want me doing too much with her.
Like, I felt her up and stuff.
But like, they fucked each other.
It was kind of a shitty hotel room too.
And it was like real hot.
So like, we didn't really do too much.
Yeah.
No air conditioning.
Yeah.
Yeah.
The air conditioner was like a little bit.
Like I was sweating because obviously, I have long hair, but like I wear
a wig because it's nicer.
Yeah.
And so like it wasn't the best, uh, meet up like with a
couple. Like, and then she did have a strap on, but it was like, so it was like the size of my
finger. So like, she did fuck with the strap on, but it was like, I kind of didn't feel this.
And so, like, it was hot on paper, but overall it wasn't that great.
Oh, interesting. And you didn't keep in touch with them because that would have been maybe
if you got the better place and it would have been good, right? Did you ever see them again?
No, I didn't mail the guy a couple times. And, you know, we sent pictures back and forward
for them and kind of, I'd never heard from again. Like, that's weird. Like, a lot of the cross-thros that I
I meet up with like sometimes you keep conversation
then all of a sudden they just disappear totally.
Right, because maybe they got in a conversation
with another person and you know what I mean?
Yeah, either that or like even though like I'm not
looking for a relationship with them and just saying, you know, I'm just looking
to hook up like I don't know if it's, they feel
ashamed or guilty and that's why you don't hear from them.
Or sometimes like you won't hear from them for months and then you hear from
them again. So I guess that's part of it.
Yeah, maybe they get freaked out and then
they're like, I'm never doing that again.
And then time goes by and they get horny for it again.
They're like.
Yeah, yeah.
right? Yeah, definitely.
I mean, because you had that, like, it's interesting with you.
I mean, you had that, like, maybe on your first experience, but you sort of came to terms
with that, and you don't feel that way anymore, right?
No, like, I did first, and I felt like, like, kind of a little shamed, but like I said,
like, I was just, I really like this.
So, you know, even if it is gay, who gives a shit, you know?
Yeah.
So, yeah, so right away, like, you hear a lot of things about cross-dress, they'll say
they purge, which means they take all their clothes and throw it away because they're done.
They're never coming back.
Oh, really?
though. Yeah, yeah, that's a thing with the cross-rises. And I've never done that because, like, for me, I'm like, well, I like, like, these heels I paid for, you know, and I'm like, keep them. And, like, I've never really been ashamed of it. But, like, I honestly, I don't want to tell everybody, you know. Yeah. Yeah, you don't. Like, I have, I have gay friends. I don't even tell them, you know. Right. So it's not like you're ashamed, but you do, you don't want people to know. And I don't know if that's ashamed or it's just like, because it's just like opening up.
a whole thing like there's just so much explaining to have to do yeah and to like and to like and to like
you know and then the you know all the questions they have i kind of just want to avoid that so that's why i
usually don't tell anybody like probably if i was with a girl for like a long relationship i probably
would tell her eventually but you know right you would yeah you'd want to because wouldn't it be
ideal if you could have like what that guy had because you said like your thing would be like you're with a
woman who's cool with the cross dressing and would like to have three
reasons every now that guy had it so you know that it exists that there's women out there that would
be totally cool but you would have to be with someone like you said a long term for because you're not
that's not something you're going to throw out on the first date no no not even like a month like hey
i like to yeah not even right yeah you probably look better than you do so i'm like yeah i've been
stealing your clothes what kind of shit do you like to wear like are you like like you like skirts and
dresses and uh yeah i kind of like i'm always
to the like sexy secretary type of look like that like i love i love glasses on a woman too so like
when i dress up i have a pair of glasses like in a non-prescription so like that's so i try like sexy
business woman so like oh like i don't wear any like latex or anything like that and i wanted that sissy
shit uh kind of just like nice long like not like kind of short dresses there's i have some short skirts
but nothing like club wear more like it wouldn't be that outrageous if you see me like in our
office you know what i mean like yeah like kind of like sexy but somewhat kind of like
conservative like that's my thing let me ask you this because you said the first time that you met
that guy in the hotel you went into the room and got dressed so is do is that still the way you roll
like you don't go out at like you're not even in your car dressed up like it's just something
that you do when you're in a plate because god forbid like you get an accident or pulled over
something like that yeah yeah yeah yeah yeah I would say like what are you thinking yeah that's a lot of
explain to do you know yeah yeah usually like I'll even say to me like is it okay if I get
change once I get there. And a lot of them they are like some said no they don't like that.
I'm like well, you know, it's kind of hard to you know dress up completely like a woman in the
middle of summer and no one's seeing anything, you know.
Yeah, walking out to your car and your neighborhood and stuff. Yeah, which like it's like maybe
if I lived on the country and I could possibly do it. But then still when you get to wherever
you're going to meet them, you're going to have to go out and you know, I don't want to cause
a scene, you know, I'm not, I'm not into like some cross-wresters, there are big things to go out to a bar.
Yeah, maybe they have the little exhibitionist. Yeah, that's what's going to ask like if you
ever were out of town or something where you can sort of do it and nobody would know and you say
you look good dressed up like have you ever sort of walked out and about in front of people like
when you're not in your neighborhood or no no no i haven't like people have invited me like there's
some place in new jersey i forget the name of it it's like um i don't know but it's they have like
a cross-dressing event like every whatever once a month or twice a month yeah and like i i got
invited there and i'm like i don't know and i'm just i'm real timid about it because i don't
Like, a lot of them, they're big things, like, go out and show offwards.
Not so much, you know.
I'm kind of just happy with taking pictures and showing off that way.
Right.
There's no turn on for it.
There's no upside for it.
So, like, what was why even bother?
Yeah.
So I've never really gone out, like, dressed up, you know, especially, like, some of them when I go to, like, the supermarket.
Like, I haven't heard.
Yeah.
I've heard.
Yeah.
I had a guy on here who, like, told me.
It was like, I thought he was lying.
I said in my intro, like, I think maybe he was lying.
But he was saying, like, he would walk out in his neighborhood.
And I was, like, questioning him.
like we'd use oh is not that that one guy that was really like hard to hear
yeah yeah that guy seemed out like totally insane yeah I thought he was and like he was
like you like you even called out and said like uh are you making this up as you go and it kind of
yeah he kind of seemed like because he would say one thing but then he'd say the other yeah
it doesn't make sense I'm like I grill you like Barbara Walters like you can't really
lie to me like it's hard because I will ask a lot of questions if something doesn't make
sense I'm going to be like what the fuck you know yeah so that's why I want that like
fueled me to call it and like well let me tell you my
story and like I'm actually a cross-dresser
so I'll tell you how we go. Yeah and you don't go
and you say but and I think that's why
listen I'll have like a million guys on that are
panty-hose 50
guys that have cheated on their wives like
20 people you know they're all the same kind of
topic right but everybody's story
is so different because each person
like I always say like people are like a concoction
right of like different things
and that's what makes people unique
right everyone has like little different parts so
you could be like another cross-dresser
but your story is completely different to
somebody else's and even though you're into panty hose you're into them in a very different way and that's why i will
always have everybody on my show even if it's the same thing like i said because it's like you can listen to all
my panty hose people right but each one was different you know some of them are more the same but
everybody's story is unique and different oh yeah and like some i would agree with what they're saying
some of like i don't hear that but like yeah that's what's different like i said some cross-dresses are
really into uh just hooking up with guys where i don't hook up with guys at all that aren't
cross-rars like real guys right they want to be the girl and be with a guy some people yeah go on yeah there's this weird uh like
there's this i don't know the group like cross-dresses where they want to hook up with any guy so like they even go with like fat and old gross guys and like they call it something i don't know what it is but like
what that's like a thing yeah like daddies or something kind of yeah yeah yeah where they're always like these gross guys because like obviously i look at cross-dress are porn all the time you know
yeah that's a lot of the videos i'm like this is ugh that's a turn off you
Right, but for them it's a turn on.
Yeah, so they're really into, whereas I'm not, I'm just into like, you know, cross-dresser or cross-dresser.
And you want them to look hot.
I mean, do you like get turned off, like as far as like when a cross-dresser hits you up?
If they, like have bad makeup or don't look so good, like are you like, no thanks?
Yeah, kind of.
Or I just won't even reply.
Like, what's your type?
My type is, excuse me.
Do you guys burp?
Yeah, I did.
That was awesome.
That was the first.
I don't think anyone else.
Really?
How professional.
I know.
It doesn't matter.
Yeah.
Yeah.
My type is kind of I try to look like, try to find ones that kind of look like me sort of.
I mean, not exactly.
Like I don't care about hair color and stuff.
But as long as they like they have full makeup and they have a wig or real hair and they, not not fat, big fat things.
Because there's a lot of like, I'll get messages like some big fat guy.
He has like panties and a bra.
I'm like, no, I don't think so.
And like as long as they're, they look feminine and they're somewhat.
but, you know, in shape, because I'm in real good shape.
Yeah.
So, you know, I try.
You work out and stuff.
Yeah, yeah.
So I keep myself in shape.
So I want to be with someone also in shape.
So let me ask you this.
If you're really buffed, does it get in the way of you feeling feminine when you're dressed up?
Or are you not, like, so, like, jacked up with muscles and just super toned?
No, I'm not, like, super jacked.
I do have a little bit, like, I have, like, white shoulders and stuff.
So, like, I don't want to get any more muscular because then I won't look as good in the dress, you know?
And I want to be some big bulky thing.
Right.
But, yeah, so I try to stay more lean.
Yeah.
But, yeah.
And what about nails?
Do you paint your nails and your toes and shit like that when you go out and then you take them off or you just like press on nails so that it's easy?
I've never really been into like the nail painting thing.
Like I don't like nail polish on girls so much.
I like the French nail.
Yeah.
Press on.
And that's about it.
That's about it as far as I go for that.
Right.
Because that would be annoying to have to like put it on and then take it off and then put it.
Right.
So that's probably the cross just juice is they just snap.
They put the pressons on.
Yeah, usually like the pressons.
I mean, some do paint their neck.
But I mean to paint your nails to hook up for someone for an hour and then take it off like it's a lot of work
So yeah what do you think is like the majority of the people that you see? Like do you feel like the majority of them are like living double lives that are married guys that are someplace? You know what I mean? Like do you ever find ones that are gay and gay relationships? Like what do you find that most of these cross dressers are? For the most I know like ones that I've hooked up with and ones like on vet life they are married. Yeah, you know, they do hide it from their wives. I guess I guess.
they feel like I can never say this or be over.
But like, you know, I couldn't be married because like I would always like, I want to do this.
So either tell her or get out of the relationship.
But yeah, most of them are married.
I don't so much full on like gay guys because I think like I don't think gay guys are so much into it.
Like you know.
Right, right, right.
They like they like want a big jack guy or something.
Yeah, yeah, yeah.
And they want to be a guy with a guy.
Yeah.
Yeah.
Yeah.
So very rarely do you see like a process as like an open gay man.
Right.
But you're usually married.
And then the younger single people, too.
That's about, you know.
Young guys.
Yeah.
Right.
And what's the old, like, what's the, do you have,
you had any, like, weird experience, bad experiences, great.
I'm always into extremes.
Yeah.
Yeah.
I mean, I had a couple great ones I'll talk about.
I think the one, like, the first time I got fucked, it was great.
And then first the two girls I met up with.
I'll tell a one that was really hot.
But, excuse me, you know, I met a girl.
I was talking to her, I think it was two.
felt like my
craigslist
yeah
and I got there and
she was dressed like a guy
which I was like
I was immediately turned off
I was like well
you're in your house
but did you discuss ahead of time
because maybe she was doing
what you were doing
I should go in the room
which which I'm okay
like yeah
you know with that
but like it was her house
so like
I was like well like
well he could have been dressed
whatever you know
and then she did get dressed up
but she looked okay
and like kind of helped her
with makeup and
but she kept like
drinking and smoking
babe like crazy
and like
This is, that was eternal.
Because I don't drink or smoke or anything.
Yeah, yeah.
So, so she got like really drunk.
And, you know, we did.
Was it her first time, maybe?
Yeah.
I guess, like, for her super nervous or whatever.
So, you know, we just blew each other.
And she was really, like, into, like, taking huge things in her ass.
So, like, I did get to fuck her.
Like, it took forever because she's like, oh, I don't know and blah, blah, blah.
And, uh, no, we, we probably did do it.
And it was like, she was super loose, which I'm.
not used to at all.
And like, yeah.
And she was like totally drunk.
And I'm like, I just am not into this at all.
And then I just kind of, she was like, well, do you want me to fuck you?
And I was like, no, I think I'm going to go.
Oh, God.
It was that bad.
Yeah.
She just was so drunk and like, and I was like, I was like, I was like, I was like, I
might as well be with a corpse.
It's not even like you're with a real person.
They're so checked out, right?
That's why I don't get people that like, like to fuck really, really drunk people.
It's kind of like a weird.
It's like a not even like you're not a real person.
Yeah.
And then you might not even remember it afterwards.
And like that's the whole point of it to have fun and remember.
Yeah.
And then like and before I fucked her like she's like, well, I'm going to go out and have a smoke.
And I'm like, what?
Like you're smoking this vapor left.
And she like went and like took her wig off and stuff and put like jogging pants and stuff on.
And then went out in the porch and smoked the set.
I was like, what?
And I was like, do I leave now?
Because like I just wanted to get the hell out of there.
Yeah.
Yeah.
Yeah.
It was.
And then like so I fucked her a little bit.
And I was like.
she wanted to do me and it's like no
I was like I'm gonna go and she was just like to the point
like slow in words and everything and I was like I got
the hell out of there the only good thing is I took a couple
good pictures of myself and she took good pictures of me
so that was like the only positive of that experience
so wait how did you know that she'd like to put
really big things in her asses because she told you and then you felt that she was
so loose oh she had told you when you guys were taught
yeah she told me like before because like usually I like to like
have some type of conversation with them emails back and forth or
or texts you know to like kind of see if they're
nuts or whatever you know yeah
And she seemed all right.
You did a good job betting her or not.
Yeah, yeah.
And she's like, well, I really like to take it to extremes.
I'm like, what do you mean?
And she's like, I really like sticking big things up my ass.
She sent me a picture of dildo.
It was like, it's like big as my hand.
I'm like, yeah, I'm not into that.
Right, right, right.
And then when you fucked her, it was like, like, you barely felt it.
It's kind of like, like, just super loose.
And I'm like, this is the first.
and like it didn't really feel good for me too much.
And I just,
and I wasn't into it too because she was drunk
and I was just totally turned off kind of.
So you spread.
Yeah,
so that's nice.
I was like,
I got to go.
I got to get at her.
Right.
That was the bad one.
There was another super hot one you said you were telling.
Yeah.
Yeah, there was another girl that I would talk to.
And she actually had a Craigslist at the time.
So it was like two years ago when Craigslist was still going on.
And I replied,
and I didn't hear nothing for a couple days.
And then she finally got back to me and said,
oh,
I was busy and blah,
and,
uh,
you know,
I would like to meet up because I sent some pictures.
Yeah.
And then, you know, then she sent some of me with her face.
I'm like, wow, she's really cute.
And we talked like for two weeks.
And then we were going to meet up one day.
And then I guess her girlfriend was there or whatever.
And then we did finally did meet up.
And she was really cute when I got there.
And then I got changed.
And we took some really hot pictures together.
And, you know, of course, we made out and everything,
we blew each other.
But I, I fucked her.
She didn't fuck me.
But that was like super hot because how cute she was.
She was good luck.
Yeah, yeah.
Like she would, like, she would have been.
a good looking guy, like, but then with makeup and everything, she looked awesome.
So that was like, probably my favorite one.
Then I did meet up with another girl that was, like, totally versed like me.
And she's like, well, I usually don't let people fuck me, but you're really hot.
So, and then she was like, she had this awesome, like red dress on, like, real blonde
hair and everything.
And we, uh, we actually fucked each other like two or three times each.
So the same night or other times, right?
Yeah.
Yeah, the same night.
And that one, that was probably, like, my top two favorite, which Ohio.
Because like you guys obviously had good chemistry if you were like into it for that much, right?
Yeah.
And they're both normal and cool and stuff.
Yeah.
And like, yeah, if we can like suck each other and fuck each other a couple times and come a couple times, that's like, that's the best.
Besides that one couple, do you keep in touch with most of these people or do a lot of them just fall?
But like how many do you have like in rotation besides that two that you see once a month?
Do you have other ones that you remain in touch and see all the time every now and that?
I try to.
Sometimes it's hard with schedules.
because a lot of them want to meet during the day during the week, and I can't because of work.
But I do try and keep touch.
I probably have like four to five that I talk to, but like as far as meeting up, it's very rare, you know, once in a while, like maybe once or twice a year, if that even.
Right.
So I would like, like, if I wasn't dating one, I would like someone to hook up with like every two, three weeks or so.
You know, like a regular.
Yeah, yeah.
I'm surprised you can't find that.
It's, it is.
It's hard to, like, especially because I look really good.
I'm like, I don't understand what's going on.
But like, you know what it is?
Like you said, most of them are married and have kids.
So they can't get that involved probably.
You know what I mean?
Yeah.
They have like too much other shit going on in the real life.
They're living a double life, you know.
Also, guys like variety.
We all know that.
Even though they're fucking girls and they're dressing up like girls, they're guys, right?
Yeah.
So they like variety, right?
And maybe they're like, you know, so I think, you know,
it's hard probably it makes sense that it would be kind of hard to keep one yeah because they you know especially
if you're you know you're married you didn't have kids and they have no idea obviously like yeah i get it you know
obviously i'm single so i've tons every time you know i'm like whenever i want yeah yeah you're more
rare right most people wind up hooked up and relationships i'm more like you i get the whole like not
needing a relationship or wanting it like i love being alone like i don't know it's like to me it's more
like scary to be in a relationship it seems more like boring to me to be in a relationship than to be
sort of free right and i get it you know i have always felt like there's a commitment phobic part of that
in me but there's also just another part of me like that just is like just loves like is super
independent you know what i mean and doesn't want to be sort of i never had that fantasy
with someone my whole life like that was like it sounds like the worst thing imaginable you know
but most people are not like that right it's like everyone's different
right and people like you exist
people like me exist but a lot of people
the majority do like to be partnered up
you know so it's
you know it's harder to find
a thing for you yeah I agree with it
yeah what you said totally like I like
I love being able like take a nap whenever I want
and I have to like you know argue and you're not lonely
for whatever you know I don't know that that's a bad thing
that's just the way that you are you know
maybe you write it's like like I said I always felt like
oh I'm so commitment phobic but
Like I think even with that gone, because I commit to things now and stuff, I still like don't have like I'm not dying for anything.
But I do feel like, you know, you never know.
Like if you met somebody, like it's a different thing, you know.
But you're super young and that's how you feel.
But I think that's why it's hard for you to find someone on the regular, you know, as far as like a booty call cross dresser, a regular person.
And you're not, you're fishing out of a much smaller pond, right?
I mean, it's like...
Yeah, I mean, yeah, you're limited a way you can pick.
And especially if you don't, like, if I just want to go with any crossresters,
then it would be a little bit easier, but like I'm not going with some totally disgusting thing, you know?
And there's a lot that are just like, they know makeup, but they look like, you know,
like a five-year-old did their makeup.
And it's just like, you know.
Yeah, you know.
Get on Google.
Like, get on YouTube.
Yeah.
That's what I say.
And a lot of them are like, well, I don't know how to do makeup.
And I'm like, well, near to die until I learned.
So like, go watch makeup tutorials.
That's how I did it, you know?
Yeah.
But some people just aren't like they're not interested in getting information that way.
Like I'm a Googleaholic too.
Like I, that's how I do figure out everything, learn everything.
Oh, yeah, me too.
Right?
But a lot of people, because most of my friends are, and I give them all the information that I Google.
I'm like, I do it for everybody else, you know.
But a lot of people just aren't that way.
So that's why I was wondering where you got your tips.
But you're just that type of person that goes out and figures it out on your own.
Yeah, like that's with anything.
If I don't know it, I'll just Google it and like, well, well, I'm sure I can figure it out.
It's not like rocket science.
or anything.
Right, exactly.
I'm just curious of when you're going to be with another girl.
You've got to keep me posting on that.
I always do an end of the year sort of update show.
We're so close to the end of the year, so I don't know if you'll have an update by then.
But, you know.
Yeah, I'll definitely do it.
Yeah, it's not that, like, I don't want to.
Like, if I meet a girl and we hit it off, sure, you know.
But it's just I'm not, like, motivated to go out on Tinder or anything.
Yes.
Yeah.
You're content and you're happy.
That's cool.
So just like, you know, it's that.
But you just never know if that'll ever change.
You know what I mean?
Who knows?
Yeah, you know, I wake up tomorrow and want to get married or something.
But yeah.
Probably not.
That probably won't happen.
But like you might wake up, you know, six months from now and be like, I really want pussy.
Like, and maybe just go have like really put the effort into meeting a girl and having a hookup because you just want that.
Or that can happen three years from now, you know, that you could eventually be that way.
But, you know, keep me posted.
I will, definitely.
All right.
Thanks so much for calling in and sharing your story.
Oh, no problem.
Hopefully, made a good episode.
Definitely, for sure.
And I'll let you know when I'm going to air.
I might air it this Sunday.
I'll email you.
Okay, all right.
Well, thank you.
Thanks, Eddie.
Thanks for calling in.
I'll know problem.
See you later, Kathy.
Bye.
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,
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