Strictly Anonymous Confessions - 241 - Is Cross-Dressing William Gay? Or is he Lying?

Episode Date: July 23, 2018

William calls in to talk all about how he started cross-dressing at a very young age and also reveals he also started hooking up with guys when he was really young. When did he start dressing up as a girl? Did he ever get caught? What exactly did he do with other guys when he was in high school? Tune in to find out and figure out if all of his stories are true of if he's actually lying and has a host of other issues. **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 [e-mail] 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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What else? I'm just going to, I don't know. I hate doing these intros, but I'm going to get right to the caller today. His name is William. And I don't know about fucking William. And I don't know if you're going to make it through this podcast. But I hope you do. because I, William wrote in and he's like, I think I'm like very obsessed with cross-dressing and I'm

questioning my sexuality. But then I don't know. Shit went down on this call and he started talking to me and I thought maybe he was lying. And then it turns out that I think he has like other kinds of problems other than his sexuality and his cross-dressing. Even though that's what he wanted to sort of talk about. I don't know. I was, I'm very confused about this because I was confused about it when I was talking to him and I accused him of lying and I felt like I was kind of mean to him. And then I'm like, you know, when I edit it and listened back, I'll have a clear view. Like, I'll hear it as an outsider, right? And like, really, I'll know whether I was right or wrong. Like, was I just me. And when I listened to it, I was just as fucking confused as when I talked to him.

So I'm looking for you guys to write in and tell me if you think this guy was lying or if you think he was just telling the truth and I was being mean to him by accusing him of lying or if you think he was jerking off the whole time because I thought that was maybe an option. I think I left that in. I didn't even edit that shit out. There was a lot of times I had to tell him to speak up because he was a low talker. Most of the time I edited it out, but there was a couple ones I just left in because I was like, you know, this is just, this is just goes with this episode because it's like it was hard. It was a hard one to do. And I feel for this guy because when he wrote it and he said he was very nervous and I'm like, don't worry. I'm so easy to talk to. And it was really like the opposite.

But anyway, so his name is William and like I said, he's into cross-dressing. He's dabbled with guys. We talk about that stuff, but then other stuff comes into play because of all the questions I ask him. I judge Judy him. Let me tell you. So anyway, I'm going to be right back on with William. So write in though if you have your opinions of what you think. Strictly Anonymous podcast at gill.com. I'll be right back on with William. Do you have a story, lifestyle, or situation you can't talk about to anyone, to anyone? Or do you just want to let your freak flag fly and be on the show? Well, Strictly Anonymous wants to hear from you. Send us an email, Strictly Anonymous podcast at gmail.com with your story

and your anonymous name. remember everything is strictly anonymous. Strictly Anonymous. Hey, William, welcome to Strictly Anonymous podcast. How are you doing today? Hi. I'm great, Kathy. How are you doing today?

I'm doing good. So all I know about you, William, is that you wrote in and said you're really masculine, macho guy. I don't know that anyone uses the word macho, but you use the word masculine, right? Does anyone use that word macho? Macho is so 80s. Yeah. You're a very masculine dude that has recently or has is very hardcore sort of into wearing

women's clothing. I don't know if it's recently or not. We'll get into that. And you also sort of are questioning your sexuality as well. And you're like, I just want to write in and like call in and just like talk about this, right? Because this is like something that's like very secretive, I'm assuming. And this is like going to be like the first time that you're sort of admitting to the all this kind of stuff.

Right. Yes, it is. Yeah, like in a weird way, this is like what my podcast has become, a place for people like you to really sort of speak their truth for the first time. And I have to say most of the time at the end of the call, people are like so relieved. You know, it was like really sort of beneficial for them to let that out, right? And talk about it. Right? Right. Yes. Yes. Yes. It is. So what's your deal? Like when did the whole women's clothing thing start for you and how into it are you? They started when I was 14. Yeah. I was always curious of what it was like to be a woman. So it started with me first trying to want mother's shoes around the house. I just do like around the house, like half an hour until an hour.

Just get a feel for walking the heels. Then it graduated to me. I would wear like my mother's panties in school. Oh, you would take them out of her drawer, put them on and wear them all day in school. You weren't afraid that she would find out? Well, no, not at first, but she found out eventually. Oh, she did? Okay, we'll get to that, to build up to that. Yeah, she did.

I started with just a pain, and then I was wearing the bra. We had the bra after a couple of weeks. Me being comfortable, I didn't have the whole stocking, the whole lot. So you were like the shoes, the stocking, like, so you were like full-on cross-dressing. in your house? Yes. Yes. Right?

Yes. I did not decide. First I was scared. I don't want to go on the street like this. Right. Like, first I was put, oh,

excuse me that, I would go like on the block. It's just dressed like a woman. Outside in your neighborhood? Yes. That's balzy. I mean, let me ask you this,

because is it like that, is it ballsy or is it that The drive to do it is so much more powerful than your fear of getting caught, right? Like, is it like some sort of thing that's inside of you that even though you know it's, like, crazy to do that someone could totally spot you and you can get busted, that you just feel like you have to do it? Or were you just balzy? I don't know.

No, I was just baldsy. I want to see people's reaction to it. But you weren't afraid of getting busted? I mean, because I'm sorry, but like, I mean, you're 14 years old. There's no way you were outside looking like a woman, right? You probably looked like you dressed in women's clothing and you're in your neighborhood. Like, wouldn't you think like people would see you? Oh, yeah.

Well, I like the reaction. Oh, my God. So you did get, so people saw you dressed like this. This isn't some secret thing because people did see you that knew you? Well Okay Not on my block No not on my block

It's around the neighborhood When I go to a friend's house Change Yeah But you would go to a friend's house Just like a girl Or dress like you And then you change at your friend's house

And they would know that you So this isn't a secret Well this person I went to The only person that would Okay Okay Okay

So there was one person that knew about this. This isn't such a secret life. I mean, you're like walking around your neighborhood in high heels and panties and you're, you're only 14. Like I said, I mean, it's going to be pretty obvious that you're you. I don't know. Not something doesn't make sense, but maybe you're not, you're telling the truth about this story, right? So, um, so you start walking around your neighborhood. So who's the friend that knows? And how does that friend, how did you break the news to that friend? Walking with my friend. We've been I know the girl's still in the middle.

What? Yeah. Yeah, and I decided, she's the only person I couldn't talk to. It was a girl. Yeah. And how was she, what was her reaction when you told her? Well, she was kind of, she was shocked because I don't really look like that kind of person to her. Right.

Uh-huh, you're masculine. She's like, wow, you? But she was like, you? Yeah. And I was like, yeah. And she first, she was like, nah, you're full of, you know, full of shit. I was like, no, I showed her the clothes. And she's like, I want to see you in them.

So I put them on. Uh-huh. And I walked around. And it was also kind of more like a day or two. It was like, you went to walk outside like that. Oh, okay. So it was like more for fun kind of thing. It wasn't like you didn't act like it was so serious.

So then you went and you walked outside? Yes. Now, did anyone that you know recognize you? I mean, one or two people from school. was like, is that? I could hear him. Like, I walked in about a bunch of people, a couple people

I knew in a park. It was like, it's like, it looks like , William Paul. I was like, I didn't say anything to him. I just kept walking, just walked straight ahead. And I heard people, like, is that William? Is that William? He looked like him.

Right, okay. And you like that. You liked sort of people. You were kind of like an exhibitionist cross-dresser at this point. Like, was there something about them kind of knowing that it was you that was like you were into it? Yeah, I was really into it. I liked the people's reaction, which I was looking for. Really?

Yeah. Like their reaction, like what, their shock? So, okay. So it wasn't like you were trying to keep it a secret. I would think that this is the type of thing that if some kids, is like really confused about and doing these kind of things that they would they would be so secretive about it but for some reason you were you kind of wanted people to know or you liked people's reaction to know that maybe it was you when you were doing this yeah because at the time

I was kind of confused and I said is this really what I want to do if I have the courage to walk outside like this okay the people's reaction the people's reaction to help me you know to help me build up the confidence to go out. Why? What was their reaction that gave you the car? Like, what kind of reactions did you get? It was mixed. I was like, oh, my, look at this.

Home model. Wow, he was working in. I had a mixed. But what was it about the reactions that gave you confidence? Was it the ones, the people that accepted it? Was it that people just, saw and said shit that you like the attention? Like, what was it that gave you confidence of them reacting to you if you were,

it was mixed reaction? Well, trust me the people who, excuse me, the people who accepted it, to get me more confidence. They were like, oh, you look nice or maybe you should do this. You'll touch yourself up here. And I'm like, okay, I'll take that advice. And for the people who hate it, I just learned to ignore it to help me. Okay.

I'm older to. Okay. So you started crossdressing at a very early age, and you were out with it. I mean, this sounds like you were like very out with it in high school. Because I'm sorry, you tell one girl in high school. Girls are gossipy even when they're 45, okay? At 14, you can't tell a secret to a girl without her spreading it, right? So there's no way that that girl kept your secret about dressing up in your mommy's clothes, okay, to herself.

So everyone must have found out in your high school, right? Absolutely good. What? They did find out, yes. Okay, and what were the ramifications for you with that? Well, most of the people, people didn't believe it, but I actually got caught. Now, how I got caught me, stuff to school, because now, I had accidentally left my own bag open.

I shared with another person and the person happened to see all the stuff in it. Okay. So we kind of, he kind of, as you put two or two to the difference. So I was kind of caught. All right,

but, but if stuff like that goes around the school, does the school, like, wind up calling your mother? Is that how your mother found out? I mean, how did your mother find out, too? You said your mom caught you eventually as well. Yeah. Well, she, first in school,

yeah, the school. Listen, Are you, like, wait, wait, wait, are you walking while we're talking? Like, what are you doing that it's making you so out of breath you could barely talk? Are you jerking off? I mean, like, what hell are you doing? No, I'm taking care of the sick relative. Okay, but like, all right, but you sound like out of breath while we're talking,

and then it's hard to understand you. So, okay, go on. So the school called your mother. Yeah, so mom came. and they said, you know, we've been hearing the sun, women, and women want models from their underwear and stuff like that. But how did they know you're wearing it?

I thought they caught it in a bag. Listen, let me just tell you something, William. If you're making this story up, you will never be able to make a story up with me because I ask so many questions that you will never be able to answer them all if this is a fabricated story. this you have to tell me the honest to God's truth or else it'll be so obvious that this isn't a real story

because I question people like judge fucking Judy okay and I will back I back you into corners that you will knock it out of if this is like this right now for some reason this story sounds fake to me because it doesn't like make sense you started off saying that like this is a big secret of yours nobody knows and this is going to be the first time you're talking about it then it turns out there's like one girl that knows about it. Then it turns out that everyone in high school knows about it. And then it turns out they found out because you had stuff in a bag. But then it turns out that they call your mom and they say he's dressing in underwear.

But who's looking at your underwear in school? I think that that's illegal. So like what I don't understand where's what's the truth in this situation? And listen, if you're lying about it, that's even more fascinating. We could talk about that, okay? But I have to call you out on it because it doesn't sound right. Like something sounds off here. I mean, I got caught in school.

That's all true. Okay. I don't know if you were seeing. You got caught? Okay, maybe. Okay, so you got caught in school, how? Because someone found your bag? Yeah, that was one.

I had two of them. And I got caught with it on because, you know, my school would be there on uniform. So you could have a white shirt. One of the guys that he could see it with the ball. through my shirt. You wear blazers, tie, white shirt. Okay, so they could see through your white top

to see you the bra that you had on. Yeah. The first of my school saw the bra through my shirt. Right. Okay. And told, went and told higher up. Okay, and then the higher up called your mother.

Yes. And then what happened? And they called me. Yeah. They called me until the, office. And I still had to know. I didn't know what they were called before.

Uh-huh. And my mom was in there. And they were in there. And they asked, they said, I said, you had this was born on. And I was actually, can't hide it. Yeah. And they said, you have it on it. It was like, I'm screwed.

Like, I'm caught. Okay. And then what happened? They sent me home that day. Yeah. And my mom was like, It's just something we do often. I told her, no, this is the first time thing.

It's like a bet. I didn't really tell her. It's just something I do all the time. Right. I just kind of lied to us and said, oh, first time thing, it's a little bet to me and a friend in school. Right. Okay.

I don't do it again. And I got in trouble. I sent me home for three days. Keep it a secret. So your mom catching you was really when your school caught you and she found out. School called me first. They told your mother,

and then your mother just let go of it after that, and that was that with your mom? No, my mom, she was kind of like, I know she told me everything is cool. I know she's kind of looking through her jewels, looking,

sure she doesn't miss you. Okay. Cool off on doing it. I know she was, I know my mother, and I know when she said something, it's cool. Back on my eyes,

she's watching me. Right, right, right. She was just trying to figure it out. She was just saying that, right? So you cooled off with it for a little bit. What about, okay, but now everyone in school knows that you wear bras. Like, I mean, was there a lot of backlash? Did you lose friends?

Like, did they make fun of you? Like, what was the deal? Because in high school, people could be pretty vicious. Most of the guys mean, funny me a lot. Like, Amy Williams, you got your bra on today? Yeah, I can imagine. A couple of girls who like. You know, I'll let you ball in my training, but it's a little, a little tough for me on now.

A couple people was like, are you gay or five or what? Uh-huh. And at that point, how did you feel? Well, the hurt. This is getting made fun of every day. Right. Like never ended. Yeah, I can imagine.

Yeah. And, but you continue to cross-dress, I'm assuming, because it was, probably like just something that you really enjoyed doing. You couldn't stop. Yes. I was upset. In what sense? It sounds like it.

In what sense? Meaning like you would still take your mom stuff when you go outside, would you keep it in, in, would you still wear shit to school even though you got busted? Like what, did? Like one of my good, like, one of my friends, I would try to, like, I would try to, like, I'll pay you if you let me follow this. Right. I'll pay you this.

to go on that. And would she? I would try it. Would she lend you stuff? If I paid her, yes, she would. Okay, well, she wasn't, she was smart. But where would you get your girl?

Would you still be wearing your mom's stuff? Well, long just, yeah. Okay, but when you were obsessed, like if you, okay, you just, you stopped going outside? Yeah, like, just around in the house when she was out of work, I would put it on. just walk around the house with it. Okay.

While she was gone. Uh-huh. And like this was like a sexual thing for you? Like it would like you jerk off when you were wearing your shit? I did, yes. Okay. And now did you question your sexuality back then? I can't be.

Okay. I'm not into that stuff. I did kind of question it a little bit. I had a friend of mine who was. very feminine. I'm not into that stuff. And me and him, that's in the room. I hear that ask me,

have you ever thought of being a guy? Is that something you'd be into? Something I thought about. Like, I dreamt about it. Right. Never acted on it. Right. I've never acted on it.

But you told him that you dreamt about it, but never acted on it. Then did you guys fool around at all? tongue anything just kiss some lips okay just the first time just a little pet see if I like this

well that's a little like that's a little romantic considering because most of the guys that I know that full around in high school they're just like are jerking each other off

and you know like I don't know touching like hard dicks like I haven't heard of guys that's just like the kissing thing is kind of sweet like I mean like you know maybe you're like that could be more like

because the difference between maybe somebody who's younger and maybe someone who might be gay as opposed to the person who's younger and might be by, right? The by guy might just jerk off while they're watching, you know, girls. But maybe you and your friend kissing was because maybe there was something a little bit more to it. Because kissing is kind of like, you know, at 14, isn't that kind of like more romantic than sexual? Like, you know what I mean? Like, there was no rubbing each other's or anything like that.

I mean, it wasn't like holding toes heads or anything. It was just like quick. Okay, so you guys kiss and that was it. Nothing happened. No, no, no. Not that time. Okay. But I did think about it.

I was like, am I really interested in this? Uh-huh. Like, it's something I made too. I mean, I was really interested in the scene. I was really curious to see. This is what I want. Right. Now, I had an incident with one summer.

I was 16. This is when I'm 17. Yeah. I stayed over at a friend's house for the summer. And then one night I was in his room. And I woke up and he was joking off. You what? Yeah, so it was really awkward.

You know, we had that look. like, oh, damn, I'm busted. Okay, so you woke up and he was jerking off and you caught him and he said, oh, shit, he gave you that look. And then what happened? Yeah, and he had asked me, like, have you ever just told him another guy before? I was like, no. He was like, do you want to? I said, ah, I gave me a try.

Uh-huh. This was your friend. This was your good friend? Yes. Uh-huh. And I did it. It took a long time. You weren't good at it.

It took a long time for him to come from you jerking him off? Yeah. Okay, maybe he was nervous. Yeah, because I didn't really know what I was doing. Uh-huh. I didn't jerked myself. I didn't really know what I was doing. At 17, you still had never jerked off yourself?

No. Yeah, but I just asked you before when you were, like, wearing your mom's clothes whether you would jerk off. because you were wearing them. It was a sexual thing. You said, yes. I said it was aroused, but I never really,

like I wasn't jerked off at the time. Okay. So you still hadn't found your penis at 17. You had never jerked off, even though all that cross-dressing, all the arousal. You know, I've heard that before. I think it's very odd,

but I have heard it before from Guy. So, okay. So I thought you did, though, say before that you were jerking up when you were wearing your mom's clothes, but you didn't know to jerk off then, even though you were aroused. You jerk this guy off before you ever have jerked off at all.

Yeah. Okay, did he jerk you off after? Oh, not the first time. Not the first time you did, no. So how many, so wait, so you jerked him off, you guys went to sleep, and then you went back another time and did it, and then you guys started to do this on a regular basis? It was like a couple days after that.

Okay. I think over there for the summer. Right. So a couple days after that, I was like I want to try it I try it again I was like yeah

I did it to him better than the first time and he's like can I do it to you so I hesitate and I said I had to take this all right go ahead he did it to me

and it felt so good that we did it a couple of times that day okay so and is that what made you start questioning your sexuality yes Okay

I kept dreaming about it I wanted I want it Okay And so did you guys do it the whole summer Yes Just jerking off or did you guys do anything else We graduated to give him You would blow him and he would blow you both

Yes Did you swallow No I was always afraid he could do it Okay Did he swallow No not just a lot so he didn't do it. Yeah, like towels. You guys were doing a towel.

Yeah. Mm-hmm. I was listening. I was always a phrase. I'm like, ugh, I don't. She looks nasty. I don't want to. All right. Was he like your best friend?

Yes, one of my good friends. So was it weird, like, when you guys would wake up the next day and sort of be out playing around, like, everything that you guys were, like, flowing around at night? Or, like, did you guys, like, discuss it during the day? Or was it just, like, or would you just, like, not discuss it? And then, like, all of a sudden at nighttime, you guys would, like, become these guys that would fill around with each other. Yeah, we made a pact. So, after we leave, once we go outside, we don't talk about it.

Uh-huh. What happens in the house? We leave it in the house. Okay. So you guys got, as far as you guys got with blow jobs? Yes. With him, yes. Uh-huh.

And so that's, like, when you're 17 and then, and you're still cross-dressing at this time, too? Yes. the low, yes. Okay, great. And so then what happens after that? Then I decided I was going to start going out to clubs, to gay clubs. Uh-huh.

Because I was 20, because I was always afraid to go out, like by myself. One day, one Friday I decided, you know what, when we go out, if I could pick up somebody. So I went out, and I met a couple of people.

nobody I would date no guys I'm really into yeah but then I had a couple of drinks and I met this guy and I met home with him and if he did me

I was the bottom for him right and that was the first time you being the bottom yes the first time I had sex you didn't get sexual with the guy yeah yeah well blowjubs are kind of sexual but you mean like you know it's of course yes

right right okay so that was the first time and you were a bottom and did you enjoy it? It hurt. But did you like it? It hurt the first time. Yeah, I enjoyed it. I did. First I was afraid because he's really big.

I was like, oh no. Yeah, but I really think like, I mean, if you're like at the point where you're like going to Gabe or cruising for a guy that, and you have never been penetrated any way, from a guy and it's like your first time I would think it'd be like amazing now it like a hurt yeah first time it hurt really bad okay so it wasn't

so great the first time maybe he didn't know what he was doing let me ask you this all this time right after all this time after all this time like or during all this time with fooling around with the guy in your the house and like this guy are you dating girls

during all of us I could have I had one girlfriend, yes. Okay, now was she from your high school? I mean, who would date you in high school if they knew you were cross-dressing? I mean, like, how long, did you have a long-term girlfriend? Had you lost your virginity yet to girls? Or did you just only lose your virginity to a guy first?

No, I dated one girl from junior high school to high school, and she was by. So, actually, she liked it. She was like, you're cool with what? The woman was cool. Okay, so she liked you dressed. So she was okay So you were open to her too about it So see this is where you're like

It seems weird Because like you start off like only one person knows And I said but you told me no one knows And you said no just this one person But now it's like your girlfriend knew Right your girlfriend knew You would dress up in front of your girlfriend This is like

Last year of high school Okay so your girlfriend No you just said you dated her the whole time So when everyone found out in high school Okay Yeah, when I came out Everybody started out at high school What?

When I actually Like in front of her Full women It was like the last year The last year of high school And she liked it Yeah Okay

So now this was in high school How old were you at that time? 16 Okay So is that at the same time That you're fooling around with that guy? I mean, did you lose your virginity to the girl? Did you fuck her?

No, I never said to do. So you dated her for years. You said you dated her for years from junior high to high school, but you never fucked her? Yeah. And she stayed dating you? Yeah. That's weird.

Was she like Mormon? No, no. I mean, what girl would stay with a guy that didn't want to fuck her for so long? We wasn't like, what would you guys do together? I mean, we kissed. I never I never slept to me Okay but I think maybe you're just

Full-on gay Are you gay? Like do you consider yourself gay At this point in your life Or are you still confused? Um I'm still by Like I consider myself fine

But why didn't you have the desire To fuck that girl You were dating her for years I don't know She only asked I have no idea Well maybe I was in for my head

No but did your dick get her Did you like tits and pussy Like did you go down on her like what would you do with her? Like I never, I never slept with me, I never, I never,

you can't get sexually just make them So maybe that wasn't your girlfriend, maybe that was your friend I mean, this is very confusing This girl's your girlfriend and you're saying you never got sexual with her? What does that mean?

If you have her, I did how to meet with course. Okay, but did you have oral sex? No, we did do anything? I don't know. I'm not going to. But, But are you positive you guys were dating?

Yes, absolutely. I don't know, maybe I'm just such a horror. I was such a horror in high school that I can't imagine. Like maybe there was like people in my school that were having these kinds of relationships. I don't know. Could people write in and tell me if this is normal behavior? Because I think this sounds very bizarre. The people are dating for years, right, in high school.

And you're 30. So you're from a different generation. You're a lot younger. So it was like you talking like 10 years ago. You're dating some girl for years. And you guys don't even go. to any basis with each other, but you're dating. Like, that sounds very abnormal to me.

It sounds almost unbelievable like the rest of your story. I mean, you guys made out? Did you feel her tits? Did she take her top off? Did you get to, did you finger her? No, I didn't do it. I didn't figure her. I sucked on a titty.

Did she blow you? No, we didn't go on. We didn't go on. Okay, but she was bisexual. So was she eating snacks? match behind your back or in front of you? Like, I mean, like, it's really weird that you say that, like, you had this girlfriend and she was bi, yet you guys were together, but you guys weren't doing anything, but she's

bisexual. So you would think she's very, like, sort of sexual as a person, right? Because she already knows she's bisexual and she knows that you're cross-dressing. But somehow you guys have these very alternative lifestyles yet you're very prude with each other. It sounds like either a total crook of shit or it sounds like she was gay and you were gay and you guys didn't know it, and so you had a relationship, but you guys didn't fool around

because neither one of you was into the other sex. Maybe she was gay, and you were gay. But you said she liked when you dressed up as a girl, but you guys wouldn't even fool around. William, William. I'm going to get to the bottom of this. I don't know. It's funny.

You mentioned three things because. Okay. with these. Wait, wait, you guys speak up. What? She's gay now. She's gay now. No, she was gay then.

If this is a true story, she was gay then and you're gay now, okay? And you were gay then. You're gay now. You were gay then. She was gay. Everyone was fucking gay.

That guy in your high school, maybe that you were blowing. He might be by. I don't know. But you, well, it took him a long time for you to jerk him off, so I'm not really sure. But, yeah.

Yeah, she was, she's gay now? Yeah, she was gay then. And you were probably gay then too, because the fact that you guys, like, were with each other for so long and you didn't have, like, because people, you're just so horny when you're young, like, you rub yourself up against anything, the wind fucking blows and you can have an orgasm. And so, like, if you're straight and you have tits, finally, like, right in front of you're telling me that you didn't even, like, jerk off your whole life.

like, right, and you have all this like hornyness going on with all this cross-dressing. And then supposedly if you're straight or by, you finally have a girlfriend and there's like tits and everything right in front of you could like go to town and you do nothing except kiss this girl. You got to don't even go down her pants and she doesn't do anything to you yet you stayed with her. That sounds very like not normal for a heterosexual sort of young guy that's coming into his own. and same with the girl well when did you

did you ever lose your virginity or a girl have you ever had a girlfriend no I don't know what yeah so you do okay so I don't know if you're confused about your sexuality but if you are I think it's like a

you definitely are probably gay right don't you think you are if you've never had sex with a girl doesn't seem like you want to have sex. It's not like you're a loser that couldn't get girls. You had a girlfriend. You had the bisexual girlfriend. Like she was supposedly the bi girl in school. You had a girlfriend, another friend who knew you were cross-dressing. Everyone in high school knew. Like, yet you, and you had a girlfriend, but you didn't do anything about it. You still, at 30, it's been 10 years. You have never had a girlfriend yet. You've been cruising guys since

you're like 20 years old. So it's weird that you're sort of questioning. your sexuality. I would think you would be, you would know by now that you're gay. No? Yeah. You know, I'm still confused. Well, what are you confused about? What are you confused about? I don't want to date a guy. I don't know if I'm going to have sex with him. I don't want to date him. Well, listen, you could be a gay guy that's like commitment-phobic or a gay guy that's like not into like, you know, it's just like a player, doesn't like relationship. and maybe you have issues with relationships and maybe you're not interested in relationships. But are you horny for girls at all?

Like does your dick, like when you Google porn and you jerk off, because I'm assuming you jerk off now, right? Yes. Okay. Do you jerk off to women or do you just strictly jerk off to guys? You do? Okay. So you have an attraction to the female body?

Well, your specific type. What type? With a body type. Well, what's your body type? I'm a breast. So you're like big tits? Yes. Okay.

Now, have you had any? Because you've never lost your virginity to a woman. Isn't that frustrating to you at 30 or is it not frustrating to you? Maybe it is. Like, I mean, you had the wherewithal to go and cruise guys at 20, right? And get laid and get fucked in the ass by a guy at 20. And like everything that you said that you have done, it sounds like you're the type of person that sort of goes after what you want. I mean, it doesn't, you don't seem that

sort of timid in sort of going after the things that you desire, right? So, why haven't you been able to score a girl? Maybe they're attracted. Maybe because why? I don't know if they don't find me attracted. I'm not too sure. Have you, have you, how many guys have you been with? So the guy in high school and the guy you fucked at 20 or another guy after the guy you fucked it at 20? Another guy after. So what happened with that guy? What happened with the guy after? So that guy did you just see him that one time, the guy that you bought him with, the first guy?

Oh, that was my friend. He was your friend? No, no, no, not your friend in the high school that you were jerking each other off. The guy that you cruised in the gay bar, that guy, the guy with the big dick that fucked you in the end. Oh, no, no. That was a one time. Okay. Right, right. That was a one-time thing. So how long after that did you have your next guy?

Like was it years? I mean, I don't need to know exactly, but like was it a couple of years? I mean, you're 20 years old, you're 30 years old. So you mean to tell me for 10 years you've only had sex with one person, because you've already told me that you haven't had sex with any girls. You told me that you had sex with a guy when you were 20, and you told me you've only had sex with one more guy. So that means that, so if I do the math correctly, and I believe your story, you have only fooled around one. Once in the past 10 years. Yeah. Is that true? Yes. Well, you might be asexual. I had a girlfriend. I called her cutney.

She didn't fuck anyone for like eight years either. I just said, this is like, I can't even, I don't even understand it. But that's like, you might have issues that are deeper than, like, I think your issues are a lot deeper than your sexuality. You might have like commitment people issues. You know what I mean? Because, like, how do you go? You know, you're a guy, right? Even as a girl, I was hornier than you.

Like, it doesn't make sense that you've had sex once in 10 years. What? I haven't gone out. Okay, but you were able to meet somebody at 20, right? You went to a gay bar, you met a guy, you fucked him, right? Did you start going to gay bars after that a lot? I stopped doing whatever. You stopped going out.

Okay, so what did you do? Did you become a workaholic? I mean, what did you do at 20 years old if you're not going out? Like, did you, you didn't have a relationship, okay? So a lot of times, you know, people don't have to go out as much when they're in relationships because they go see movies and they go out to dinner and they stay home and cuddle and eat ice cream with their lover. Like, you didn't have that going on.

Like, what did you do in your 20s if you weren't going out and you weren't having sex and you weren't dating girls and you weren't dating guys? What were you doing in your 20s? I mostly work in my life school. You're working? Yes. Okay. And what do you do for a living?

Is it like, is that like, are you, maybe you're a workaholic? Have you been in a, like, do you have a desire to be in a relationship? Are you ever lonely? Are you ever horny? Like, recently I've been a little lonely. Uh-huh. You've been going on the day and perhaps. Okay.

And how is that working? out for you. And I've talked to a couple of people. Girls or guys? Both. I have a couple of girls interested and a couple guys. But do you post yourself being bisexual

and so then you have both guys and girls hitting on you? Or are you in different apps? One app as a straight guy looking for girls, another app as like a gay guy looking for guys. I mean, how do you have both people sort of into you? What about a vibe? I'm like, especially

through the street. So you have one app where you're, you post yourself as buy, another app where you post yourself as straight. And you still haven't been able to hook up with another guy. You've had one guy a couple years ago. How did you meet that guy? The second guy that you had sex with?

That's what I went out to the court. Okay, so you went out to another club and you met a guy. So if you're lonely, why aren't you just going out to clubs? Well, kind of blessed I am. We're afraid to go on. I've had issues. talking to people. Yeah, you got like I'm telling you, William, this is the deal with you. Like, this is nothing to do with your sexuality. You have like deeper stuff going on like, I think,

with people in general. Do you know what I mean? Because it doesn't matter whether you're gay or straight. I don't think that that has anything to do with the problem in your life. Your thing is that you are not having any kind of relationships with people. Do you know what I mean? Like it's not because of your sexuality and what your orientation is or anything like that. It has to do with something else going on. I don't know what that is, but, you know, I think, I mean, do you have any friends? Yes, I do.

Okay, so you have friends. Okay, so that's cool. You're guys, guy, like guys have guys friends. Some guys are into like having girlfriends, but, and you did in high school and they were actually very cool with you because of your cross-dressing. But do you think that you keep people away because of like the cross-dressing thing? You're afraid to let them in and let them know about you. But what about, you know, like, why do you think you don't let people in emotionally or sexually?

Well, I mean, I'm kind of like more private. I want to be like more mysterious. I don't know what? Okay. But what do you think changed from like the kid that was younger, that was cross-stressing? dressing and wanting to go out and get reactions from people to the guy that you are now. To the same guy, the same guy that was like dressing up with his girlfriend and let her know and let his other friend know and went outside and let people know in the neighborhood.

And then at 20 went out to a gay bar and fucked a guy right away. Like where is that guy now? Like you seem like you're not that person anymore. Because if you like what happened after that experience or, or the second experience with a guy that you've been so closed up that you haven't been able to hook up with anybody.

Guy or girl. I mean, you've never hooked up with a girl. No. I lost my nerves. I mean, you know, it's happening. I don't know. I used to be happy.

You lost your nerve? Is that what you said? I can't understand. You talking to the phone or talk out of the phone or do something different. You lost your nerve? Yeah.

I don't know. Like, I don't know. Like, I used to be able to go. talk with the people of church. Yeah. Well, you know what happened sometimes? It's like if you stopped doing something for a long time, like you could get really in your head about something

and then you become like super maybe nervous or something. Like you need to have some fucking action. I don't know if I believed half the things you tell me. I don't know what the real story is. I don't know. Because I don't know if I believe everything that you're telling me. You could be just like a compulsive. of a compulsive liar, but I

really wonder if you are a compulsive liar and if this whole story isn't real, like what the real story is, or there's some truth in this and maybe you're like a recluse that doesn't really know. I don't know, but there's something like off here and I can't put my finger on it.

Because listen, if you haven't had a relationship or any kind of sex or anything for 10 years, like, and you're only 30 years old, I mean, you're not 60. Like, what the fuck is going on? And don't you think that's a problem? Don't you think that's the problem?

Yeah, I do. If it is, and you can start going out. I don't know what it is. When you see somebody, maybe go talk to someone. But someone, is that a girl or a guy?

When you're picturing yourself going out and meeting somebody, is it a girl or a guy? Ladies and men. Yeah, I think you should try relationship with a guy, I think you're straight of gay. I think you're gay. Even if you have a slight tendency towards women,

I think you're like if you have a percentage, you're probably like 80% guy, 20% girl, which makes you more homosexual than heterosexual. Like I think a, you know what I mean? Yes. Because you've had more experiences with guys and when you had

a girl, like every time an experience with a guy has presented itself to you, you jumped on it. You know, you wake up, your friend's jerking off and you jump to jerk him off. You had a girlfriend for years. You could have done shit with her and you didn't take the opportunity to do anything with her. So I think you're a lot more into guys than you are girls. I think you're gay. Maybe you have a slight tendency to tits. I think some gay guys are like that, but I think you're mostly gay and you should probably try to have a relationship

with a guy. Like a relationship. You're going to give it a shot? You're going to give it a shot? Yeah, I want to be more with you. You what? I want to be able to go out. But you can't go out. No one's holding you back. You said you have friends.

You go out. I don't know, William. I don't know that I believe any of this shit that you're telling me. Are you telling me the truth? I am. You are? Yes. I can't wait to hear what my listeners think about this story.

I'm going to say on the intro, like I think this whole podcast is like, I don't, like I said, I don't know what is true. and what's not and if it if you were lying what would be the point of it I don't know like because your initial email was like I'm a cross-dresser so do you still cross-dress but only at home right you don't go out

yes no no okay you're still you jerk off now I'm assuming yes to both guys and girls you haven't ever had a relationship with a girl doesn't anyone wonder

about that? I think maybe my family number of sister what? What? I mean

my family normal suspect nobody's ever asked me and nobody's ever asking. And do you think that you

haven't had a relationship with a guy in a long time because you're afraid of being gay? Like,

I mean, do you have an issue with being gay at all, do you think? Oh, I mean,

maybe going out of public with the men and kissing like I used to be But like what about bringing a guy home to your family and introducing them and like holding hands with a guy and like being like this is my guy? This is my boyfriend. I'm gay. Could you do that? At the moment, no? At the moment, no? Do you think maybe that's what holds you back? That maybe you're just not ready to sort of accept it, but yet that's really who you are and that's why you're waiting. Because I think if like you were like more by, you'd go out and just do the easy thing, which would be like get a, like, get a. girlfriend, but I don't think you have a desire

for a girlfriend that. Like, I don't think you have a desire for tits and ass of a girl as much as you do a guy. Am I right or am I wrong? No, you might. Hadnison doubts. Douts? You're having to figure out how

you act. How does it must not deserve to act. Dude, you've got fucked in the ass. You've been out. Gay guys are a lot easier to, like, I think it's like a gay guy. Being a gay guy is like the ultimate. thing to be. If I was a guy, I'd be fucking gay. I don't know. Poor straight guys. You know, they have to fuck girls and girls are like them. I mean, gay guys are where it's at. Okay. They're

like really fucking horny and the people that they date are really fucking horny too. And they're just all on the same page. And it's very easy, I think, in that world, to hook up. Okay, what are you on a scale of one to ten? What are you on a scale of one to ten? Sit? A what? like six and a half. A six and a half. Okay, so do something to get yourself up to a seven and then you'll be fine. Do you have a good body? Because guys, like, gay guys are very into like the body.

Are you into like, do you have a good body? Do you work out? You're 30 years old. You should look good. You're decent. You're decent. Do you have a big dick? Average.

Average. Okay. So, but so you're six and a half. half your body's okay. I would get yourself to a gym. Get yourself ripped and then go on Tinder. You're going to have no problem. Do you know what I'm saying? I mean gay guys are like I walk around New York. I mean New York is not filled with good looking guys. I walk around New York and like all the hot guys. I'm like oh yeah they're gay like the gay men look fucking good okay and they like other men look good because no different than straight guys. I mean they're very visual right. That's why like

women we have to look so good because like you know straight men are looking at us on the outside you know that's quote unquote shallow whatever that's just the way guys are wired so gay guys are really looking at guys that have a nice ass that have good abs you know that look good so you know or have a big dick or something you know there's got to be something you got to have it going on yeah but if you go to gay bars you're going to meet a guy you got to channel that young William in you, if that young William exists. I don't know. I don't believe a word you said, but if it

But if those stories of you walking out and all that shit is going, you could just be that person again. Go to a gay bar. You know, I think you're gay. And you should just date a guy.

You think so? You think so? I feel bad, William, because you said you were like a little nervous to call in and like, I don't know. I'm very curious to see what my listeners think and people could write in and be like, oh my God, Kathy, you're so rude to the guy. Like he was obviously telling you the truth that you did about it. Or people are going to be like Kathy, you totally knew. Like, I don't know. And then I'm starting to feel bad because I know you said you were so nervous.

And I'm like, oh, don't worry. I'm so easy to talk to you. But all I've done is like Judge Judy to you all the whole conversation and to call you like a liar. I mean, is that terrible of me? let's see, no, this for me is like high in the public. I know what I want to say and articulate it.

Right. You know, I used to have a guy on Yeah, I used to have a guy on called Tuna who had like, and people hated his episodes. People couldn't fucking stand when I had poor Tuna on, but I loved him because he was like a real socially awkward guy that really just wanted

to fuck girls, you know, and he couldn't meet any because he was like really socially kind of retarded. And that's a bad work to use, but like socially, like, he just didn't know how to be. And I really wanted to help him, because I really liked Tuna. He was like a nice guy, you know? And it's like if he was my son, I'd love him. Like he was just like a good kid. But he had no game, you know? And my listeners hated when I had his episodes because he could barely fucking talk. Do you know what I mean? He couldn't even like speak. And you're, you're not as bad as him at all. Okay. You're really not. But

you do have like a thing with talk. and maybe you have a social kind of like awkwardness and maybe you could go to like a therapist and like talk to them about that because that'll help you. I know what I want to say. No, it's even the way you talk.

It's like half the time I could barely hear what you're saying because you start off confident talking and then you like a mumble, that's what you do. Then you go someplace like you just lose your sort of steam and then it's like mumbling and I can't even hear you. know. So you have to like, you got to find your voice. I think personally, if all this stuff was true, okay, I'm going to say it again, I think that when you were younger, you had more

balls and you have to, and I think it's very natural and it happens a lot of people that when they get older, they lose their balls. It's much easier to have balls when you're younger because you don't think as much. You're not in the real world. You know, you're just more carefree. You don't, like your mind isn't evolved. You haven't had enough. sort of rejection to know to be afraid of it. Do you know what I mean all those things? So what happens with a lot of people is they just get older and they become more fearful and more afraid and more everything. And that's like the kiss of death because that's the kind of shit that makes you old and right. And before you know it, I mean, you're 30 now. 10 years have gone by and supposedly you only got

fucked once, okay? 10 more, 20 more. When you get older, life's just going to go by even faster. I mean, like, you know, another 10 years could go by and you haven't lived your life, you know. So you want to get on it now. You're still very young. I mean, you're only 30 years old, right? You want to go find your voice, get rid of some of these fears and the social stuff that you have going on. I think you're gay. Just be gay.

Who cares? And live life. You're going to have a great time being gay. And you know, and you should do it. Or become a drag queen. I don't know. You should figure out what it is you want to do and go do it because you're not. not really living a life yet.

You have no life as far as like romantically and sexually. And that's like a big, like if life is a pie and like it's equal pieces, like I don't think sex should be everything. I don't think a romantic relationship should be everything. I didn't have a lot of long-term relationships. But like you should have a little bit of everything in your life, right? You have a job. You like your job.

You have friends. You like your friends. Like you should have a little sex. That should be a piece of your pie. And you have like two pieces of pie that are totally missing. And you're too young not to have those pieces. You know, you're going to be 67 years old and a lot of people don't have those pieces of pie anymore

and they're fine with it because they're so fucking old. But like, you're not, you're really young. This is when you should be eating a lot of pie. Okay. I agree. You need to just get back out there. Put yourself up as gay, please, on Tinder and go to the gym

and get yourself at the, therapist or just get really good pictures of yourself and go meet a guy. Definitely, we do. Okay, William, I can't wait to see what people write in about this episode and what people think. I don't know. I hope that I helped in your hat. Are you happy that you called him? Yes, definitely.

Are you mad at me that I accused you of lying? Like, is that rude of me? I don't know. Oh, no. No. No. Okay. And you're cool with me.

like telling you that you're gay and not straight like is that okay with you? I don't get upset. I actually kind of expect them. I kind of guess. I should have taken to blind. It's kind of curious. That's what you think you are to. I can't understand what you're saying.

That's what you think you are to anyway. So that's cool that I said that. Yeah. Yeah. Okay. So yeah, I think your problem should have been like, hey, Kathy,

my name is William and I don't know how to talk to people and I don't know how to have relationships and I don't know how to have sex with people. can you help me? Like that should have been the problem because that is your problem. Everything else is okay. I don't even think, I mean the cross-dressing, who cares?

You have deeper issues than that. And if that's, you know, if you have, if you're cross-dressing and I tell you that that's no big deal compared to your social problems, you better start working on your social problem. So get to work, William. And please keep me posted because I would like to know that like you're back out there doing fucking something.

definitely. All right, go lose your virginity to a girl or a guy because basically you're a virgin again. You've got to go lose it. And let me know how it goes. All right. Good luck. Thanks for calling in. Hi, I'm happy. I appreciate you. 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, 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 audiobook is available coming out August 25th. But you could pre-order it now. And if you buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord. My Discord does not disappoint. Okay. There's no way you get into it. to my Discord any other way than getting the link from me. Okay, I give it to people who buy my book. There's tons of people in there. Everybody shares content with each other. And that's what you get to do there. You could post your own pictures and videos. There's tons of channels. We have lots of contests where you can win a lot of money. It's a super fun place to be. It's a total, strictly anonymous community and you will love it. I will be giving anyone who buys my book

access to my Discord. It's private. Like I said, all you got to do is email. me a screenshot of your purchase, whether you did the audiobook, the ebook, or the paperback. Send it to me at Strictly Anonymous Podcast at gmail.com. That's strictly anonymous podcast at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in. Do you have a story, lifestyle, or situation you can't talk about to anyone, to anyone, Or do you just want to let your freak flag fly?

And be on the show. Well, Strictly Anonymous wants to hear from you. Send us an email, Strictly Anonymous podcast at gmail.com, with your story and your anonymous name. And remember, everything is strictly anonymous. Strictly anonymous.