Strictly Anonymous Confessions - 090 - Jessica is Secretly Transgender

Episode Date: September 7, 2015

Jessica was born as guy but has been dressing up as a woman and hooking up with guys behind his familys back for the past 14 years. Jessica calls in and explains what it's really like to be living a secret life as a transgender female. She explains how and when she first realized that "he" was really a "she", what it felt like the first time she dressed up and went out as Jessica, how she picks up guys and what she does wiht them sexually and a whole lot more. If you've been following the Caitlyn Jenner story, then this episode is right up your alley. **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

Welcome to the Strictly Anonymous podcast. Conversations with online strangers. We place ads online. Craigslist is definitely a gift that keeps on giving. Real people respond. You go to Singapore or a Thailand. You can't not do it. The temptation is just too much.

Real problem. Does your friend know that you're banging her? No, he has no idea. And anything goes. The motto of the show, let your Greek flag lie. Probably the only good advice I'll ever give you is to re-hide your whips and change. Here are your hosts Kathy Kay and Tommy. Hey, welcome Strictly anonymous podcast with Kathy.

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Today I have on the show a really interesting guest. The guest's name is Jessica. And Jessica is a transgender person. Is that how you say it properly? I don't even know. Is transgendered? Is transgender? Jessica is married. to a woman as a man. But he lives a secret life.

Like his wife and his kids have no idea that he dresses up on the side and that he believes he's female, even though he was born a male and he's genetically still a man. He's not on hormones or anything like that. He's not out in his regular life. In his regular life, he's a married guy with grown-up kids. But for the past 14 years, he's been also living a double life as Jessica. And he calls in and explains everything.

about that. How it came about that he started to feel like he was more female than male. It didn't happen when he was younger. It happened way later in life when he started to dress up, when he started to fool around with guys, and what that's all about. It's really fascinating, especially because what's going on with the whole Caitlin Jenner thing. I watch that show. I know I don't talk about celebrities a lot, but it's not really about celebrity. It's about, you know, people and becoming more aware of transgender people. And I think it's really fascinating, really interesting. So I was really excited to get Jessica on as a gas. So I'll be right back on with Jessica. 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. Hi, is this Jessica? Yes, it is. Hey, Jessica.

It's Kathy. You're on the Strictly Anonymous podcast. How are you? Okay. Okay, cool. So you posted an ad on Craigslist, just looking for some female advice. You didn't say what kind of problem you had. You definitely made a point to reference the fact that you weren't looking for a hookup

or anything like that. So I sent you an email, and then you wrote back, and you had a really interesting story or a problem that you wanted to discuss with a female. Do you want to explain the problem? Do you want to get into it and just explain what you had wrote to me? Sure. Well, I'm married and I have been for many years. But for quite some time, I just felt different inside.

I feel like a female inside. So I wanted some advice. Is it wrong to just keep that a secret? it or is it's something that I should, you know, tell my family. And I've had mixed advice and people say, you know, hey, if you tell them, it's going to hurt them, you know, so if you can live with it, you know, and keep it a secret, you know, others say it's not fair because you're living alive, you know. So I've had mixed emotions.

And when it's all said and done, it's my decision. I just wanted, you know, other people's input. Of course. I think that always helps. You know, sometimes what people say to you or it's just a, it's just actually stuff that you would be saying to yourself, right? I'm sure you've thought of both sides of the story. I'm sure you could relate to the people that say, hey, you're going to hurt your family and you know that, of course. And then there's people that say, hey, be true to yourself and, you know, be honest and live a more truthful life, right?

And you could relate to that. I'm sure you have both sides or you see both sides of things. I mean, right? I do. I see both sides. but when it's all set and done and I've weighed all the options I don't think that

the happiness of one person should come before the happiness of a lot of people You don't think that is a... Wait, what did you say? Do you say you think that the happiness of one person should come over the happiness of a bunch?

Should not. Oh, should not, right, okay. If I were to If I were to tell my family, sure, then I can go ahead and make this Jessica and beat myself, you know, and do what, you know, do what I feel is right inside, you know, be who I want to be. But I truly wouldn't be happy because I know I'd caused the pain. So it's sort of like between I'm rock and a hard place, you know. Totally. If I come out, you know, I'll never truly be happy because forever and ever more I'll know that I hurt them.

Right. know. But let me tell you, let me just throw something out there, just another angle to look at things. And I'm certainly not the type of person that believes in, like, telling people what they have to do in life. Because everybody has their own path and what's right for you, you ultimately know. And it's ultimately your decision, right? But what I would say, which is like another sort of way to look at things, is that I know that you say, like, if you told your family, you would forever know that they were in pain and they were upset about it and you cause that and you could never live with that. So instead you'll live with the everyday pain of feeling that you actually are a female and you're living a male life, but you don't feel comfortable. And that for sure is going to be an ongoing pain too, right, that you would have.

But if you look at it like if you told your family, right, and they got really upset, I would bet a lot of money that eventually over time they would get past it on some level, most likely, and maybe, I mean, sometimes you can't even imagine what could be. Like, imagine that maybe they would get to a place where they would accept it, and maybe there would be some sort of like re-getting together in a better place, and maybe everyone would be happier. And then you would be able to be who you are. Your family would be able to move on with their life,

and everybody would be okay. That's a possibility, yes. believe me, Kathy, I've thought about it long and hard for all these years. And it is a possibility, but keep in mind, it's only a possibility. It's not written in stone. Right, it's a chance you take. Right, right. And I ask myself, do I want to take that chance?

And every time I come up with the same answer, no, I don't want to take the chance on hurting them. Okay, let's get some backstory, though, on the whole situation, because I think it's really fascinating, especially with the Caitlin Jenner thing. And, you know, so for you, I think it's really interesting, right? Because here you are a person who is transgender. Like, would you say you're transgender? Yes. Right.

So, and you're living in a time where there is this shift happening that you could technically come out of that closet, right, and be accepted for the first time in a, you know, and it would maybe be easier than if it happened 10 years ago. How long have you felt? Because you said for a couple of. of years now, you have felt like you're more female than male. And so how old are you now? You're 46, right? Yes. How long have you been married for? Just over 20 years. Like a little bit over 20 years, right. And now how long have you been feeling that you're more female than male or that you're

female trapped in a male body? Oh gosh. Almost 14 years now. Really? So how did that happen? Because Normally I would think, right? And I think probably a lot of my listeners would think that it's something that somebody feels very early in life, right? Like when you're like really little. Do you have any memories at all before that 14 years? Like when you were little, that maybe you also had those feelings? Or it just absolutely hit you just 14 years ago and you never felt it before? Well, I'm glad you asked that.

I grew up in a very strict Catholic family. and that was definitely frowned upon. So I'm thinking and again, I'm not a doctor or a psychiatrist, I'm thinking that

because it was so frowned upon you know, in my family and in the area that I grew up that maybe for self-preservation, my mind just blocked

everything out. Right. Typically you are right. That is something that, you know, I'm a firm believer that you're born with that. It takes some people

longer than others for it to to come to the surface, but typically it does so at a young age, not so, not in an older age like it did with me. Right, but maybe it was like... But I'm thinking that it was a self-preservation thing. Maybe my mind blocked it out. Yeah, no different than like somebody that maybe was sexually abused when they were younger

and they blocked out memories and then all of a sudden it comes out at a certain time. Like, you know, and it seems like it's like, you know, maybe it's made up because all of a sudden they're experiencing it. But really, they're just repressed memories. So maybe you even expressed it. maybe you did certain things and maybe you were told that that was like really bad. And then so you really suppressed that part of you. And then it came up for some reason, you know, 14 years ago, you know, and now it's there full-fledged.

Now, I know you also told me that you've been with men as well, right? Have you been with men as a female or have you been with men as a male? As a female. As a female. So one other quick question. before we get into that, do you, does anybody in your regular life, like I'm not, I'm assuming that you go out dressed up as a woman and there's people maybe that know you as Jessica, but does anybody who knows you as the male persona, does anybody in that world know about Jessica? Yes. Who knows?

And let me, let me say this. Yeah. To better answer your question, we said I've been with men. And if I think with men as a woman or as a man, my reply was as a woman because keep in mind that in my mind, whether I'm dressed up or not, I am a woman. Right. The clothes are just for appearance. I mean, to make a woman feel sexy or, you know, she's going out on it. But the clothes don't make who you are inside.

Right. I've known women who can dressing Levi's and get, you know, all dirty and mud and all. and they're just as feminine, it's just as much girl as any other woman. Absolutely. But just because they draw on a pair of guy shorts does not make them, you know, any less feminine.

So, yes, I love the clothes, but they don't define who I am inside. So, yes, when I'm with someone, I do so as a woman because it doesn't matter whether I'm in a skirt or in a pair of jeans. Totally. Yeah, no, I'm glad you made that distinction because that's, like, really important.

And I think a lot of people would see it, the way I see it, right? That when you're a female, you have to be dressed up as a female. But no, it's not. It's that you always, the fact that you feel like you're a female comes from the inside.

Like you said, it's not about putting on the clothes that that makes you a female. It's that feeling that you get inside, that that's who you are. Exactly. When all these feelings first started coming on, I was dressing up more often.

And at one point I asked myself, you know, if I were to stop dressing, I mean, is this just going to stop? So I did. I didn't dress and I went out, you know, and I was like, oh, my gosh, I still feel, you know, like a girl inside. It has nothing to do with the clothes. And that's when it all started, like, coming together, you know, sort of clicking. The only thing I could never explain is why so late in life.

But I just attribute that to my upbringing and, you know, my family and the area I grew up in. And then, as I said, being. being, you know, at this age, I grew up during a time where it was not a Caitlin Jenner, Ecker. You know, it was a lot, it was a lot harder. We're the same age. It's not something people, they don't want to come out. Do you have a therapist?

Do you go to therapy? I did for a while, and then I stopped going because it's always the same thing. I mean, therapists are never, ever going to give you answers. I think they're not there to give you the answers. They're there to, to, to, you know, to. Basically, to let me hear, because I always had the same reply from every therapist. The answers are within you. No one can tell you who you are or how you feel, much less myself.

This is something that you're going to have to work out inside. Right. And so I did it slowly. I tried to, you know, piece everything together, you know, the why and when and where and how and everything. And, you know, I've come to the conclusion and I've come to terms of the fact that, yes, I am Jessica, I am a female inside. Will I ever be able to live as Jessica?

I don't think so because I can't see sitting down and telling my family, hey, this is who I am and this is how I want to live. Right, and dealing with those consequences and dealing with making them feel terrible. Exactly. And even if you, as you said, even if they, over time start to accept it, accepting accepting, accepting, accepting. something and not feeling resentment towards someone. There's a fine line. I don't know if that makes sense, but there's a fine line. No, I mean.

Yeah, absolutely. Somebody could get over something and get past something and believe that's something and feel like everything is okay with something, but they could always sort of feel resentful that they had to go through what they had to go through. Absolutely. Yeah, and I don't want to lose that. I don't want to lose that relationship.

How old are your kids? They're all grown up in their 20s. So it's not yet. And I've been told by the people, look, they're grown up. It's not like you have little kids to worry about, you know, you can come and tell them this. It's not that easy. No, I think it's almost worse in a way because, you know, when you heard, I've heard this about Chris Jenner with Caitlin Jenner.

Like, I heard Kathy Lee Gifford. She was on a show talking. And normally I don't talk about celebrities, but this is just in the news. So I'm just going to bring it up. But she was talking about, because she was very good friends of Bruce Jenner. Somebody had asked her how does she feel about Bruce Jenner coming out? And she said, listen, you know, everybody could see it in a way. Like, you know, everyone looks at it and thinks it's like really amazing and it's really great.

But if you really knew him like we did and his wife did, there's like an odd sense of betrayal that comes with that. And it's very difficult to feel like you've been sort of duped by somebody. You know what I mean? And she sort of explained in a way that you would never. sort of imagine unless you were really close with the person. It's easy for me to say Caitlin Jenner is doing a great thing and to accept that now he's a she, right? But what about the person that has been living with him for the 20 years

or the friends that have been friends with him and feel like, you know, he was living and lying to them, right? And so that's what she was sort of explaining that the people really close to him feel. And I thought that that was interesting because that's probably something that people would feel who are close with people that are transgender. You know, they would feel, so, you know, your kids, the older they are, the more they would feel that that deception went on. So I don't think that it would make it easier because they are older.

It might almost make it harder. It might because when kids that are that young, they don't know what's going on. Yeah, they tend to adapt a lot easier than kids. You have to understand. For over 20 years, they've seen me as bad, you know, it's. macho guy, going out there and throwing a football around her, baseball, and doing this and that, and going fishing. And then all of a sudden, you know, they're going to see their dad, you know,

in a dress, you know, wearing heels and makeup, that's tough to swallow. And it may be something that they can never get over. And not to mention the fact that even adults, I think, can get teased. Their friends might say, wow, that's your dad. you know and that's something that they would have to deal with now and I don't want that keep one thing in mind that not every transgender out there is living in the Caitlin gender life right no I think that have you been watching the show

a lot of them get abused a lot of them have you been watching the show? I haven't and the reason I haven't is because they're making it seem you know like it's glamorous like hey if you're transgendered if you can come on and you're going to live like taking it no no no honestly let me tell you because you haven't watched you said two things in that situation you just said two things that are totally like hypocritical in that one sentence you said i haven't watched it because they're making it seem like it's so glamorous

how do you know that if you haven't watched it okay let me tell you that they're not making it seem glamorous they actually are talking about on the show exactly what you're talking about most of the women that he's going around with, you know, and helping spread the word, you know, through his celebrity are talking about how they didn't have it easy. They don't live his life. Like they're trying to get him to grasp that reality. So they're not. So you really should actually before you sort of just like become judgmental on it and say that

they're doing that you should watch it and then make that decision. And I'd be interested to know what a transgender person like you who's not. not Caitlin Jenner and doesn't live that glamorous life, what you take out of it and whether you still feel what you just said, but you have to watch it to be able to really say. I'll give it. I'll give it us by trying not watch it. But I stand corrected.

Okay, I was basing it on what I have seen in the news. Oh, please. You can't listen to people. When he was on the Keeping Up to the Kardashians, the daughters accepted it. No. Oh, my God, it's the antithesis of that. I have lost everything.

Yes. I've known trans genders that have lost everything, their jobs, their family. I mean, totally. And I've known some that have, you know, ended their own life because they just couldn't live with being alone because nobody wanted, you know, everybody that they ever knew and grew up with, you know, said, hey, we want nothing to do with you. Oh, yeah, you have to watch a show. I promise you, you're going to feel very differently about it. They really, it's really not what the news was saying it was about.

It's really not anything like keeping up the Kardashians. I've never watched more than one minute of that show in my whole life. It's so, I think it's really great, actually. But you have to watch it first. And I think you definitely should, considering it's so relatable to you, it's like your life. And just because he's somebody with like intense celebrity and you're not, he's working on that show is a bunch of people that he's surrounded with, that he travels with, that he learns about the community from. And they're like a bunch of regular transgender people. But some of them are people that were like sort of notorious in the world and people who were like, you know, trailblazers for the community.

So it's really interesting. Let me ask you this. Can we go back to like, okay. So when was the first, so you've said two interesting things. One was that people do know about Jessica, you know, people who know you as, you know, your male persona. Who are those people in your life that know that you've. told this secret to. There's, by the night, and I'm like, no, what are you talking?

And they're like, you can lie all you want, you know. But how did they know? I don't know. I honestly, and I asked them that. I said, well, finally when I admitted it, I said, how did you know? And they said, just little things you do. Okay, so they were like pretty perceptive. But are they friends of yours or any family members or just strictly friends?

No family members. just, just, yes, acquaintances. And they picked up because they said, if someone really were to pay attention and see the little things you do here and there, they could see, you know, feminine attributes. Right. That's really interesting. When was the first time that you,

okay, you said about 14 years ago is when you started to feel like a woman. Were you with men before that? Or did you start to have affairs with men after that? It was after. It was after. And then how did you meet the men? And where do you get the time?

Like, do you travel for business? Like, how do you live this sort of double life and get away with it? I do a lot of traveling. So I get to get some free time, so to speak. And basically how it meant them is just online, you know, different sites. That's basically it. You know, and from one, you know, he may have had a friend. I mean, I'm not stupid.

I know that a lot of these guys get with me because they see me or D. Or, hey, you know, she's going to give you what you want. And to a degree, it's true because I'm guessing it's because I don't get to be Jessica all the time. So it's like never giving candy to a little kid. And then all of a sudden you let them loose in a candy store and what happens? They're going to eat a lot of candy. Exactly. So, yes. So that's what happens. Jessica, you sound like a regular, yeah, you sound like a regular girl, like, oh, all these guys are just using me for sex.

That's very girllike of you to say, like, you know, you see yourself as the victim. But that's what you're looking for, right? I mean, that's what some part of you, Jessica really wants to be with a man, right? So you're, that's what they, so they talk a lot about this on the show, like whether you're transgender and, you're, you're, transgender and, you're, you're, you're, you're, you're transgender and, you're, you're, you're, you're. you're gay or whether you're transgender and your heterosexual, right? So Jessica likes men. Yes. Yes, she does

a lot. She likes men a lot. Right. And Jessica thinks guys are just using her for sex like most girls feel, because they are using you for sex. I realize that. That's what guys like. That's just the way that it goes. It's fine. But we... You know what? That's a double-h

sort because... I don't know how candid you want me to be. Be as candid as you want. Okay. You know what? As a girl, let's say you're giving a guy a blowout. Okay. Yes, he thinks he's getting what he wants.

Hey, I'm a tough dude. I'm a macha guy. I got her to do this. What he doesn't understand is that it's empowering. Yeah, you got his dick in your mouth, and you are in control at that point, and you can make him calm or not calm. Yes. Totally.

I agree. Exactly. When you're doing that, you look up at him and you can just see in his eyes, you're like, he's melting. And he's, you know what? He's feeling like this because of me, because of what I'm doing. Absolutely. Even though he thinks he's in control, he's not.

Yeah, I agree. Listen, I was always very open sexually, and I never felt like a victim to men in that sense. I think a lot of women do, but I think that that's like, there's a confusion about it. Because I believe what you believe that. Like when you're having sex, as long as it's consensual and it's what you're doing what you want to do, there is no sort of, I mean, like, you know, somebody holds all the power, you know. It just, that's why people, that's why people get horny when they're doing stuff to somebody else

because there's nothing more exciting than seeing yourself having that power to really turn somebody else on, right? And that's just good sex. A lot of people don't see it that way, but I think that that's people that have their wires sort of crossed and they have sort of weirdo, you know, issues surrounding sex. And a lot of women do for some reason they see themselves as victims when they're really not, okay? It's true. I can be completely doubt, you know, pretty little skirt, the whole nine yards, and be with a guy. And I can tell, you know, that he's already hard.

He's like, you know, he's all forming up. I have no time getting up and walking out the door and go home and, you know, sit back. can watch a movie. He's going to go in the cold shower. Exactly. Because he said that, you know, so who has the power? Mm-hmm. Totally.

I mean... So you're... So even sexually, do you feel like you're more wired like a woman more so than a man? Like, I mean, you know, I would think because genetically, right, like you're born a man. You haven't had any... Do you take hormones or anything? No, I do that. Okay.

I wish I could. Right. You could never do that because of your family. That would be a big... At that point, it would be out of the cat would be out of the bag. So you don't take any harm. So genetically, you're still a dude, right? So you're not like the regular guy that, like, if he got really horny because he was with somebody that he really liked that he'd have to go home and jerk off to, like, Jessica doesn't feel that need to be just like that guy that you just explained?

No, my gosh, no. Interesting. That's interesting. Right. So it's like your brain really is more so like the female. And, I mean, realistically, Kathy, you know, you know it between us. girls, most guys don't even last long enough for a permit for me. Right. Right. I mean, that's, at least that's been my experience. Most guys, I mean, it's over before, you know, before it even

starts. But do you like women, too? Like, can you be, are you turned on by your wife, you know, were you always turned on by women as well? Do you consider yourself kind of bisexual? I'm glad you that I consider myself a bisexual girl. I am more into men. I would prefer, you know, to be with a man. But yes, I can be with a woman and, you know, and I can get aroused. That's not a problem. Let me ask you this.

Have you ever cheated on your wife with a woman? Or were you completely monogamous with her as far as that was concerned? No, I have not. I've only been with men. Right. And when did that start again around the same time that you decided that you were, a female like 14 years ago, right? I just got home when they, from work, I got home early, and I thought, I was actually digging

through the cloud with some. I thought, I wonder what it's right to, you know, to dress up as a woman. Don't ask me why it's just like a light switch being turned on. Right, and then what did you do? I dressed up, and it instantly, I thought like, wow, this is amazing. It felt so amazing. It made me feel so amazing. so sexy, so feminine.

And that, basically, that started the whole snowball effect. I mean, after that, I was constantly wanting to be dressed up. And that, that really was the beginning of Jessica. That's where I started feeling like Jessica. I said to myself,

this is not just, you know, a little phase or, you know, like a mid-life crisis or anything like that. this is, I think, who I am inside. So I just kept exploring it. And eventually I got to the point where I'm like, okay, well, with Jessica, actually beat with a man. So I dressed up and went out and I got with a guy.

And that's when I said, okay, you know what? This is, this is thinking who I am. Right. I enjoyed it. You know, I enjoyed being with a guy. I enjoyed being hit on, you know, being treated, you know, as a female. Mm-hmm. Now, let me ask you this.

I'm assuming that when you came home that day after work, like you went into your closet and you tried on your wife's clothes. Is that who you, did you use her clothes in the beginning or always? Do you still use her clothes? Because I was going to ask, like, how do you live that double life, right? Like, how do you have your clothes and where are they stashed

that your wife doesn't find it? But basically you're using her clothes. You fit into the same size. That's kind of great. At the time, yes. At the time, I was very thin. and I got to a point where I tried to gain some weight because I was trying to fight these skills. Right.

I'm like, there's no way, you know, I discipline out. Yeah, you're a lot of people put that weight on to, like, hide who they are, right? It's like a lot of times sometimes it is psychological in that sense. So that's what you feel like you did? Exactly. I looked at my wife and my kids and I said, no, you know, that's my wife. These are my kids, you know, I'm a husband. I'm a man.

I refuse to do this. and I found that the more I tried to suppress the feelings, the more I tried to bury them, the worse it got. The more you were feeling the need to sort of be who you were, right? Exactly. Exactly. And I said, I just can't fight, you know. Kathy, it's impossible to fight who we are inside.

No, I understand. I'm somebody who, you know, is very true to who I, am and have had problems because of that, but I've never, I've never given up on who I am. You know, so I believe in that 100% and have lived my life that way always since I was really little. So I'm always somebody who's like, just be authentic and, you know, and whatever comes with that, you could deal with that. So I'm very big on that and I believe that.

I don't know. I can't be somebody else for longer than maybe like a month or two months. You know, I just, because the desire to be who I am is stronger than my desire to be liked. And that's just the fucking fact, you know. And so I had problems because of it. And because I'm a very opinionated sort of big personality type of female, which is very frowned upon. But, you know, what can you do? But I don't want to talk about that.

I want to talk about you. So wait, so you were using your wife's clothes and going out. Now, because I always think to myself, like, where did you go? Like, imagine you went, like, you know, weren't you afraid of being busted? Like, did you drive three hours out of town? Or, like, did you go to a place where maybe you would see people? Were you afraid that somebody would, like, see you out and about dress up as a female and know who you were? Or did you go to, like, a gay bar or a place where transgender people were hanging out?

Like, where did you go that first night where you met that guy that you slept with? I went out of town. I didn't want to take a chance on getting caught nor running into someone that knew me because I knew that would be devastating. So I basically, yeah, I drove a little bit, not extremely far. I drove a little bit out of town. And that's where I met in a couple of times.

Yes, I have gone to those day clubs. And what I have found and scares the daylight side of me is that Jessica seems to become older, you know, as time progresses. Mm-hmm. Where, just, I'll give you an example. I could be talking to someone. Like you, you might call, you know, let's say that you call me to have some work done. You know, I will actually start to, like, change my voice a little

and sort of drop little clues to try and get you to think, hey, you know what, this guy is her. Does that make sense? Oh, even in business, you mean you're starting to do that. When you say call up for some work, like if I was just dealing with you on a business level professionally, you might do that? Exactly. Let's say that I had to meet you in your office. And, you know, we're talking business. Strictly business.

Out of the blue, I might say, oh, my gosh, I love your shoes. Which, no guy is going to say that. well some guys will but you see what I'm saying but that makes sense no I get it maybe that's why your friends you said you had a couple friends who came to you and said hey listen

we know what you know what's going on here maybe you did that with them do you feel like maybe you sort of put it out there to them because you felt like maybe they were people that would accept it it's possible I don't know maybe I do it without even realizing you sometimes we do things and we don't even realize

They say, well, my gosh, did I do that? It's very possible that I may be doing something, you know, without even realizing that I'm doing it. Especially that you're becoming more comfortable with being Jessica. Absolutely. And I think subconsciously, sometimes we don't realize how we are ruled by our subconscious. We absolutely are. You know, you have this side of you where you really don't want your family to know. But, you know, I do believe that in this situation, there may come a time.

time that something happens by accident that your family finds out. But will it be an accident? I don't really know. Because if you have these, if you're living this double life, it may become stronger than you even realize. I totally understand because my life basically is a tug of war between Jessica and who I was born in. It's a constant battle in my mind. mind at the constant tug of war and Jessica has definitely been winning that war over the years. Right.

Have you had long-term relationships with men or just like one-night stands with them where you just like, you know, screw them and that's it? Or have you had actual relationships with men as Jessica? No, I have not. I've had one-night's

that's it. I have had oh my gosh, I had a guy one time after just one meeting he says, you know, I would marry you tomorrow and I would get to all the hormones you want. I don't know. I mean, he was like, I'm looking at him like, are you serious? He said, yeah.

Yeah, absolutely. I mean, you're amazing. I think you're a wonderful girl. And he's just speeding me this line. I'm like, he's either crazy or he's serious and he was serious. Have you ever had a situation where you meet a man? And, I mean, do you think most of them know off the bat that you're transgender and what they're getting into or have their average?

been any surprises with a guy? No, I'm always up front because I know how dangerous that can be. Now, again, I know, you know how guys are. They'll tell you whatever, you know, whatever a girl wants to hear, that's what they'll tell them. Right. So, you know, I've been honest with them. They said, really, I never would have known, you know. And I know that I'm not the prettiest girl out there.

And I know it, you know, unless, if. completely blind, they should be able to tell, but they don't care. Right. You have to keep in mind, you know, these guys, a lot of these guys, and here's the crazy part, a lot of these guys are married.

You'd be surprised how many married guys who act all big and tough, you know, sitting around Sundays watching football aren't, you know, girls like me. And what are they? Like, I wonder what they consider themselves. Are they gay? Or, you know,

like what would because they're with a woman right they're with jessica but they're having anal sex right with a man they're doing sort of the sexual stuff that a gay man would do so i wonder what they consider themselves well i'm glad you asked it because i've asked them myself yeah and what did they say you know when when when we meet and we talk and i'll tell them so because i i tell them right away i said look i like masculine men you know if you're you know if you're you know if you're little crazy and that's not what i want right Right. You want a man. And I want a man.

You know, and so when I've asked them, they said, oh, I'm straight. I'm not into guys at all. And I'm thinking to myself, that's kind of a, you know, double-extriced. Okay, you're not into guys, you're man. They always being very manly, you know, real macho guys. But I'm technically, like you said, I was born a guy. I mean, it's in my heart, my soul, my mind, yes, I'm just a woman. But when they're blowing you, you're, they're blowing you, right?

They're like, you're a Jessica like that has a dick, right? So, I mean, so that, to me, would be like maybe they're bisexual. Oh, see, they don't like doing that. Oh, really? Guys I've been with? Yeah, they're like, no, I won't suck a guy. That's, you know. So what do they do with you?

Basically, most of the time what they want is, you know, about God, because they always have the same story. Well, my girlfriend won't do it, and my wife won't do it. I said, okay, well, Jessica will, you know. That's so funny. Like, they just want to blow them and they just any mouth will do. But so they'll let you blow them, but they won't blow you. Will they let you fuck them in the ass, or will they fuck you in the ass?

No, they won't take anything. They'll suck me. And they'll let me suck them and they'll definitely suck me. But they won't. Like I said, the guys that I've been with, they all say the same thing. You know, I'm a straight guy. I'm not into that. I'm not going to bend over for anyone, and I'm not going to suck it,

and this and that and blah, blah, blah. I'm like, well, whatever, you know, whatever. And that's fine by me because then as Jessica, I get a guy who's basically acting like a guy, like a regular. That's what you're looking for. And he, and because he's a total dude acting like a dude, he's treating me like a girl because in his mind he wants to assure himself that hey I'm with a girl I'm not with a guy

that makes him feel like he's not gay it makes me feel good because he's treating me the way I want to be treated yeah actually that makes no yeah I never would see it that way but actually when you just explain it that way that is the perfect guy for you that is the way it works perfect for you because that's like you say is what you're actually looking for if you're him in the ass or blowing him, then you're not real, like, then you're doing more like what a man would do with a man, right?

So when you're servicing him, it's more like what the woman would do with the guy, right? And when he's screwing you, it's more like a, you're in the female position. So yeah, it absolutely makes sense. And I would never have looked at it that way unless you explained it. Okay. Well, I'm glad I was able to, I thought I was going to have trouble explaining a letter, but that's basically how it is. And it works out for everyone.

I just said they're getting what they want. They think they got over on me, but they didn't because I'm getting what I like. You know, I'm getting treated the way I want to be treated, you know, which makes me feel good. And yeah, well, heck, I like Dick. I'm sorry, you know. Right. Now, like, how many men have you been with in the past 14 years? Is it something like, oh, you could, like, count them on your one hand or two hands,

or have you been with a lot of guys? Like, you can't, you couldn't even keep track? Like, have you been super promiscuous? as Jessica or have you like tried to keep it under wraps as much as possible? Totally. Oh my God. Jessica's a total slut.

Jessica, hey, I admit that freely. I am a slut and I'm fine with it. You know what? I don't care. It's not a bad word. Right. No, it's not. And you know what? Jessica likes sex. I don't care. Jessica likes sex. Jessica loves men and Jessica

loves sex. And you know what? It's funny because if guys do it, they pat them on the back, oh man, you're lucky, you're a stud. But if a girl does it, she's a slut. You know what? Girls love sex as much as guys. And yes, I love guys and I love sex. And yes, there have been, you know, just a few guys.

Good for Jessica. No, a lot of guys. Good for Jessica. So Jessica, like, sort of knows what she wants. She goes out. She gets a lot of guys. And you've been able to, so far, never get caught. Like, where do you do, like, the email and the texting and all that stuff?

Like, do you have a separate? phone like how do you keep it so that you don't get busted well email I have a separate email account that no one knows of so that that is my main yeah that's my main form of communication because the texting it's too dangerous totally and I had a guy text me one time when he wasn't supposed to and it you know um it almost ended badly so I don't do the texting anymore because you think guys are just I'm sorry guys are stupid tell them, hey, don't text me here. And right away, you get a text, hey, girl,

what you're up to? You want to come on over? Right, right, right. I'm like, hello? Did I not tell you? But the problem is, guys, you know, I've always, guys think with, with one head. Right, exactly. And it's the one down there. You know, the guys are like. When they're horny, they're not thinking properly. I always

say, like, that state of horniness is like, sort of like being drunk. You're not in the frame of, you know, I've seen the most smartest men I know, right? Act like total imbeciles. And really not that bright. And sort of. sloppy when they're really super horny, right? Because all of that intelligence goes out the window and they're just like a horny guy is not that smart.

You're right. They're not. They're not, guys. And, oh my gosh, they're so easily manipulated. I mean, once to take their pants off, they'll pretty much dance and jumps your hoops for you. You know, if they think they're going to get something. Yeah, totally.

That's what you have all the power before they come. Or while they're hard. The wall the heart. Yeah, and you're smart girl, Jessica. But this is where I think you're not smart. I feel like you're, like, I feel like somehow you're going to be caught. I think that you're, like, you know, your secret life is very, is big. Like, if you've been with a lot of guys, right, it means that you're doing sort of this thing a lot.

Do you do it a lot on your hometown or mostly always while you're traveling? No. I guess I've become older. you know, over the last year or two, I've actually been with a few guys that live locally, which I know it's bad. So I'm trying not to come to terms with the fact that you were right when you said that, you know, this is eventually going to come to the surface to the point where people are going to start to notice, hey, you know what, he acts different or he does this or he does that and, you know,

I'm trying to deal with that right now because I'm trying my best to keep it on the wraps, but it just seems to, I don't know how it, but it just seems to be getting harder and harder every day. Yeah, because sometimes, listen, sometimes like when you're focusing on like something that you don't want or you don't want to do, it's like you're still focusing on it. And that's why I think AA sometimes doesn't work for people because you're going to this place and they're always telling you what to avoid, what to avoid, what not to do, what not to do. But really, if you think about it, what your brain is really just constantly focusing on is alcohol. And your brain sometimes doesn't process the don't drink.

They just are processing the drinking thing because it's always on your mind. So sometimes actually focusing on not doing something, you know, is a focus on that something, right? So it just makes that something stronger, right? It's not like you're not thinking about it at all. That would be, I'm going to tell you, if you want to, to actually, like a cognitive therapist who deals with like, you know, just mind fucking yourself would tell you probably the best way to put Jessica on the back burner or to quiet her a little bit would be to not think about it at all, not to try to suppress her, not to try to be her,

just try to not think about her at all, right? But to try to think about not being her all the time is no different than thinking about being her all the time. Does that make sense? it does um i know i i spend countless nights away tossing and turning because i'm thinking of being jessica of course i'm thinking hey i wish i could do this i wish i could do that you like being jessica oh no i don't like it i love right at this moment right at this very moment um what i wish more than anything is that i were in my heels, my cute little skirt, you know, a nice little top and with some hot guy.

Right. But let me ask you this. Do you want to be Jessica purely for sexual reasons? Do you actually feel romantic with men, too? Like, would you like to be Jessica, like, in love with a man, married with a man? Or do you just want to be, like, Jessica sort of having, you know, sex with guys? That's a good question. Jessica would love to have fun.

Keep in mind that Jessica, and this is going to be kind of like, you're going to say what? She is totally crazy. But Jessica, in a sense, it's almost like a teenager because keep in mind that she hasn't been around forever. Right. She's like emotionally 14, 15 years old, right? Because that's as long as you've given her the room to breathe. Exactly. Emotionally, she's a teenage girl who just wants to hang out with guys, sleep with guys.

I'm one of the, I'm, you remember when you were in school, you know, where everyone said that's the school slut? Yeah. That's Jessica right now. Oh, that was me. No. In school. Really? I was very, I was very super rebellious and I was very promiscuous and I acted out a lot.

So I totally understand that. In a time when most people, well, most women weren't doing it. Nowadays, I think there's a lot more slutty women, women that are sort of acting out and doing stuff like that. So it's different now, but when I was younger, that's that I was. And that's who Jessica is. She's the school slut. Yes. Jessica is a young girl who, she's the school slut right now.

Like I said, Jessica's young, Jessica's crazy wild girl, you know, look and have fun. But there have been many moments when, again, Jessica's thought, you know, when I get older, it would be nice to have a steady board for, you know, someone that comes home and, you know, and I have dinner ready for them, you know, and made a snuggle and not just have sex, but make love. So you do want that for just. So Jessica does want, I mean, we keep talking about Jessica in the third person, but really Jessica is you. Jessica is you, right? And you keep, like I said, talking about her in the third person.

So you feel like maybe there is, there would be a time in your life where you would want to have more from a guy than just sex and maybe have a more intimate relationship emotionally. Oh my gosh. Absolutely. Absolutely. That would be, that would be nice. But for right now, no, because. First of all, it's just not possible, you know, because it would be too risky. Because guys, I know how they are.

You know, if you tell them, hey, I can't go. I'm going to be with my phone. They don't care. They'll try to text you and say, hey, you know, can you make it? Can you sneak out? Can you do this? Can you do it? Because I've been down that road.

Oh, no, you can't. Listen, once you start really having, like, a moat. Like, that's why I asked whether you've had just, you know, sex with guys or if you've had long-term relationships. When you start to have, like, long-term relationship with a guy and your, you're having a relationship with your wife, that's when you're really heading for some trouble because that's going to be a lot harder to live that kind of double life because that both, you know, the time and the energy, you know, that you have to put in to make a relationship good

is a lot. So how are you going to be putting in 100% with your wife and then 100% with your other relationship? I just think that, you know, that's when you'd really get caught. Exactly. Right now it's easier. Go there. You know, when you're done, throw my...

my panties on. Thanks for the ride, baby. And walk out the door. And that's it. No, there's nothing there. There's no commitment. Right. And the guys know it. So it makes it easier. And the guys are fine with that. I'm sure. Right. And, and, and, and I know, I know that a lot of people may listen to this,

especially women and say, well, she's a, she's a home wrecker. No, I'm not a home wrecker. But realistically, and I know this is wrong, but realistically, it's easier with a married man because they have so much to lose, they're not going to take the risk of trying to contact or you know oh i love you i want to be with you you're the one i want no they don't do that because they have their own family their own so basically each you want where i'm going yeah is that what like ashley madison was all about sort of like you know people that are in the same boat you know married people that want to cheat with other married people like when you're a married person

you're cheating with a single person they might put on the pressure to get like all this other stuff from you but when two people have that other life going for them you know then that's the perfect person to do business with. So I totally understand that. Exactly. I'm glad you do. Yeah, I mean, it makes sense. So I'm not a home wrecker. And I don't see it as a home wrecker because they

came to me. And whose home is being wrecked? Nobody knows about it at this point, right? You guys are just people. Those men that are doing it with you are people that are living a double life and haven't sort of come to terms of what they really maybe want in life or, you know, and the same

thing with you. You know, Exactly. And I can tell them no, no, sweetie. I'm sorry. I'm not going to do that because you're married. They're just going to find another girl. Just because I tell them no, doesn't mean they're going to see the error of their way and say, well, you know what? Well, Jessica was right. What I'm doing it wrong, they're not going to stop. No, please. And I tell them no. No, and I think people would probably think I'm terrible for saying this. But really the best person for you is another married guy because just for the same reason that you said before, you both have a lot more to lose. so it's easier to just go in and get out because you both go back to your your quote unquote real lives. I mean, I don't know which feels more real to you. I think some people would think your married life is more the real life, right? And Jessica is this fantasy because you're, but who do you feel is more the real you? I'm thinking you're going to say Jessica. Oh, absolutely.

So you feel like when you're doing the whole marriage thing and you're in that life that you're just like going through the motions and you're being sort of phony and sort of. of putting on this persona of somebody that you're not. And when you're Jessica, you're really being you? Let me put it to you this for me. Okay. A lot of people would see me and say, well, he's a cross-dresser. And okay, yes.

But, you know, when I'm cross-dressing, I'm cross-dressing right now because I'm dressed up as a guy. That, to me, is cross-dressing because I'm dressing up as a guy and I'm not a guy. Right. Yes. Yes, if you were to put it in percentages, I'd say that Jessica is probably 95% of who I am. Right. The other 5% is clinging on there because of my family. If it weren't from my family, I probably, I would have been living my life as just years ago.

And very, very likely I would have gone through all the motions, you know, the sex change, the whole nine yards. I'd be living totally as a woman today. Right. And what about, like, you brothers or sisters? I have two brothers. Right. Are you close with them? With one, yes. The other, not so much. Right. And again, they wouldn't understand.

No, right. I think that, of course, that's hard. I just wonder, like, if you had, I was thinking maybe if you had any sisters or anyone that was close in your family and they could, like, sort of, maybe they would remind you of things that you did when you were younger that maybe would suggest that you always had these tendencies, you know, but I'm assuming that nothing's ever come up. Yes. In therapy, one thing came up. when I was young I had a pair of shorts. And I was, I forget what I was doing. I was playing and I ripped them a little. The in scene and I kind of finished ripping them. And in essence, I turned them into a skirt because they had no in scene.

It was just, you just slipped them on it. Yeah. And even my mom had said, what are you doing with those? They're all ripped. I said, well, they're my favorite shorts. I don't want to throw them out. Uh-huh. And I kept them for a while and I wore them all the time around the house.

They look just like a skirt because I had repeat them. That's my only, my only memory or recollection of ever doing anything that even remotely, you know, seemed sending it. Right. Maybe you were like sort of criticized or ridiculed about that or, you know, maybe your parents got really freaked out and, you know, and so, and that's why you suppress everything. That would be the reason why you would suppress the memories, more so because other people told you. you it was wrong to do and made you feel really bad about it. And when I got older and started looking at like the Playboy magazines and stuff, in the shower, I would just tuck my dick between my legs and just see what it would look

like to have, to not have a big and have a vagina. Right. And this is when you were little or younger before the 14 years. Yeah, so see, these are little things. Absolutely. So these are little parts of Jessica. that you remember and you know maybe there's like you know more there like if you had probably wrote down in a journal every day of your life when you were younger you probably had a lot of

moments where you felt stuff like that or jessica sort of showed her face to you um you just forget about it our memory is so different i wrote in a journal for many many years like 10 or 12 years i have tons of journals and um i go back and read them sometimes and i realize like oh my god it's so great what's so great about writing in a journal is we tend to rewrite history in our minds. The way we remember things is very different a lot of times than the way things played out. We don't remember the day to day. We don't remember

the things that we think about. I quit drinking 12 years ago, I think it was. And when the first year I quit drinking, I went back and I read all of my journals. And I felt like when I quit drinking, it was the first time I ever thought that maybe I have a problem and I should quit drinking. But when I went back in my journals, I realized there were so many nights where, you know, when I was in the privacy

of my own room, when I was writing and I was reflecting on myself that I had wrote that I thought that, that I felt that. And I would have sworn to you that that was like the day that it happened was the first time I ever thought about it, you know? So I think that, you know, we do have thoughts and feelings about things, but we tend to forget about them and we don't really remember them, but they're there and they exist. And like I said, unless you kept a journal of every single thought that you had and you really wrote about things, there's, you lose that stuff. You know, we rewrite history and remember things in ways that seem easier to comprehend. You can't remember all the details. We'd be

nuts, you know. I agree. I agree 100%. So listen, Jessica, I mean, okay, we're at an hour. I could talk to you for like three more hours. I think it's so fascinating. I could go on too, but actually I'll have to go myself. Yeah.

So, I mean, this is what I think. I think that you've already decided what you want to do and that is not tell your family. I wonder or worry for you because you don't want to tell your family that eventually it may come out. Personally, I think that that would be a great. thing because I tend to believe in more so in just being yourself and that other people would be okay. I really truly believe that if your family found out, you know, fast forward five or 10 years, everyone would be

okay and would probably be better for it. I believe in that. I don't believe that suffering for people is something that people should avoid. I sometimes see things like that as actually positive experiences, but that's because I see life in a certain way. But other people don't and I totally get that. So I hope for you, since you don't want them to find out, that they don't find out and that you live the double life and you could be slutty, Jessica, and you could have your fun and you could keep your family and everything's cool. But if anything changes, which it could, you never know. We never know what's going to happen around the corner. You know, I'd love for you to actually just like check in every now and then and have you on again and see what's going down like a year from now or six months from now. Or if anything happens as people find out, I'd love to hear about that too.

I will And maybe down the line I'll give you another I will I will and thank you for listening Yeah and but yeah Anytime you want to call on to be back on the show I think it's a fascinating topic

It's something that's like really going on right now Because of the Caitlin Jenner thing I think it's really interesting I think that you know If you exist there's other people like you There's probably so many people That are going to be listening to my podcast That will be able to relate

And I think that that's really interesting And so thanks so much for calling in And I'd love to be back on whenever you want. Be careful. Thank you so much. Be careful, Jessica. Bye.

Okay, I just want to tell you before you go that my book, it's called strictly anonymous confession, secret sex lies of total strangers, is now available not only in paperback and ebook, but you can pre-order the audio book. It's still not going to be out until August 25th, but you can pre-order it. The book is basically 17 different stories taken from my chef. 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.

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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.

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