Strictly Anonymous Confessions - 375 - David Cheats on his Partners with Strippers, Men and Transgender Females

Episode Date: February 15, 2021

David has cheated on his partners with strippers, men and transgender females and he has recently decided to stop. When did he first start cheating? Did he ever get caught? Why did he decide to stop? Tune in to find out pls hear all about why can't he remain monogamous, how far he use to go with strippers in the back VIP rooms, when he first realized he was into men and how he went about hooking up with them, what he liked to do with them, how and why that evolved into him being into transgender females, the time he kind of dated a trans woman and how he's open to dating a trans woman but why he wouldn't do it just yet, who knows about his secret life with guys and transgenders and a whole lot more. **To see anonymous pics of my female guests + hear anonymous confessions + get all the episodes early and AD FREE, join my Patreon! It's only $7 a month and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and when you join, I'll throw in a complimentary link to my private Discord! MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: https://amzn.to/4i7hBCd To Join SDC and get a FREE Trial! click here: https://www.sdc.com/?ref=37712 or go to SDC.com and use my code 37712 Want to be on the show? Email me at [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. Strictly anonymous podcast. Conversations with online strangers. We place ads online. The Craigslist is definitely like the gift that keeps on giving. Real people respond. You go to Singapore or Thailand. You can't not do it.

The temptation is just too much. Is your real problems? Do your friend know that you're banging her or no? No, he has no idea. And anything goes. The motto of the show, let your freak flag fly. Probably the only good advice I'll ever give you is to rehire. your wips and chain. Here is your host, Kathy.

Hey, welcome to the Strictly Anonymous podcast with Kathy. If you want to follow the Strictly Anonymous podcast on Instagram or Twitter, follow the show at Strict Anonymous. Today, I have a guy named David. Now, David didn't lose his virginity until a little later in life. And then once he did, he got to it. Let me tell you. David's a guy who could not be monogamous. He got busted a lot of. of times you got to hear those stories we talk about how his baby mammas he has more than one baby mama uh how they caught him and they don't just catch him with other women they catch him with trans women um he you know he started out after you know when he started to cheat at first was like with guys

and then it was like with feminine guys and then it was with transgender females and he's been with cross-dressers and like i said he's because he has a problem being monogamous and he had a thing with always wanting to be in a relationship. He got caught a couple times. He's done a lot of things with these people. We talk about how when he first started hooking up with guys and like I said, how it transitioned from like, you know, men to transgender females and how he feels about that and whether he'd ever date that way now, what label he considers himself. I don't know. We don't know. We don't know. He doesn't know if you know what you would consider him as far as a label. There's a comment about that too. But we get into all.

of it and it's super fascinating and there's a lot of details and there's a lot of stories and I actually give him advice too you know because he's like one of those guys that's always in a relationship or he used to be always in a relationship but always cheating and finding like there was a lot of conflict with that. It's like just don't be in a fucking relationship

right and that's where he's at now he's actually come full circle so it's an interesting story to listen to I'm going to be right back on with David. Hey David welcome to the strictly anonymous podcast how are you today? I'm doing good. How are you? I'm doing good.

So you have a double life, right? Like most of my callers. Yeah, I guess you could say that. I think so. I mean, what I think is really great about you because you gave me a lengthy email, which I normally don't read, but I did read through yours for some reason.

I typically like to get on and know, like less is more for me, right? Because I'm just naturally curious and I just ask a million questions and I'll get the whole story, right? but what I like about your story is that you know you did live a double life for a really long time and maybe what you're doing now

is still secret but you're not doing it behind partners back like you're finally single and doing like your shit that you're doing right like as a single person and that's totally fine whereas you have a lot of these people that are not only living a double life but they're doing it behind like a partner's back right so they're really you know fucking with somebody else right

because they're in a relationship and they're cheating right behind their back. And I've always liked to people like, just be single. Like you could fuck whoever you want if you're single. Like I don't understand. But a lot of people have this like intense need to have a relationship, right? And have that security of that. But then they have to have this other life too, right?

But you finally separated it, right? But and that's where you're at now. Right. I'm correct, right? Yes. And you got off of like needing to have that relationship in your life. yeah I finally at 34 realized that I needed to separate it until I can get my shit straight you could you could do whatever the fuck you want why do you need to have a relationship

I don't know why people are so like needy of pairing up but maybe it's because I'm just not that type that I don't get it but like you know it's like it doesn't make sense but that's not really like all that I want to talk to you about you have like a really interesting stories let's get to your thing all I'm saying is like I commend you that you're just finally single and hooking up with people because way before now you were hooking up with other people behind a lot of women's back. So you're only 34, right? To me, that's young. But let's start at the beginning. At the beginning, okay? Where would that be for this, for your story? Like I said, my email, I lost my virginity at 1819.

Right, which you even said was kind of late, right? I'm always like, oh, that is kind of late for a guy, no? Why did you wait? Especially nowadays. Yeah, I know. Even in my day, well, no, in my day it would have been more normal for a girl. Guys would have been a little bit earlier. But why did it take you so long?

Do you know? I don't know. I was pretty book smart and concentrated on school and sports and everything. And I had girlfriends. Don't get me wrong. I just never, I guess I was just afraid to take that next step. And I guess, you know, confidence gets better with age. Yeah.

Mm-hmm. Well, you really made up for it, okay? So you leave your Virginia at 18, right? And then start from there. Yeah. And then we moved in together, right? The same girl, I lost my virginity too. And then we broke up.

and I think I was 22 at the time and dating an 18 year old. And she was kind of wild and kind of opened my eyes sexually that, you know, wasn't so vanilla. And then I cheated on her. That sex wasn't so vanilla. Like you guys did more interesting things with each other sexually.

She turned you on to stuff? Yeah, like, you know, different positions and just different places, like, out in public, different things like that. Uh-huh. So I was like, you know, what else is out there kind of thing? So we dated for about a year, and that's probably around the time. I cheated on her with my kid's mom, and she got pregnant.

But she wasn't your kid's mom. Like, so she was just another woman. Where do you meet her? Like, where did she come from? My kid's mom? Yeah. At work. Okay, so you cheat on her with a co-worker?

Correct, yes. Okay, so this girl and you are like flirting at work. Because this kind of shit happens all the time, right? I mean, because you're spending a lot of time with coworkers. Mm-hmm. Yeah. So you said to get a horny for this girl, and how do you guys cheat? Was there alcohol involved?

No, not alcohol. We did drink a few kids. but that wasn't the contributing factory we we would just hook up like in parking lots and just I love parking lots I just think it's hilarious I don't know there's something so funny about it you know because that's where a lot of people that are cheating do it you know in the back of like minivans yeah I mean it's just we couldn't really go anywhere else yeah go to each other's yeah going each other's places. Was she cheating on somebody too?

No, she was single. Okay. Yeah, she was single. But, so yeah. And she gets pregnant. Mm-hmm. And now does she get pregnant and you're still dating the other one and then you tell the other one about this whole affair thing or do you keep it a secret from her?

Well, I kept it a secret for a little bit. Mm-hmm. And then I was like, well, you can't really hide this. So at first I didn't tell her that she was pregnant. I just, I broke it off with the girl I was with. And then, you know, our city is kind of small. So where it travels fast and she found out. She wanted to make it work for a little bit, but, you know, she couldn't handle it.

What, the girl that you cheated on that had a baby? She was like, oh, I'll take you back, even though you had an affair and got the girl pregnant. Yeah. Okay. And so then she couldn't, she couldn't deal with it. No, she couldn't deal with it. Yeah, that was smart. It's hard to deal with it.

It's, uh, I don't know. You say because she had a baby, but I think it was more so because you cheated on her with this girl. You know what I mean? Oh, no doubt. Yeah. Yeah, it was like the trust. It's hard to get that back.

And like, listen, I, I think when someone has a lot more invested in a relationship, I understand people trying to get past that, right? you know if you have three kids and you've been together for 20 years and something like that happens you know you could work through it but you know you guys were young you cheated on her with a co-worker she's just you know really young too right at the time why would she stay with you you know what I mean yeah that's no offense but you know what I mean right no like I said I don't blame her at all yeah yeah so go on um and then so like I'm single now and me and the

me and the girl that I got pregnant decided to try to make it work we moved in together right before my son was born and you know we just tried to see if we can make this work for the child

and everything but it really couldn't work because I couldn't being monogamous and I couldn't go to the street be on a straight arrow well did she catch you cheating I mean well like

is that what happens or you just knew that you didn't want to be with one person well she didn't really catch me per se I was real into being into strip clubs at the time some stripper kissed me on the cheek and left lipstick

you know and I was drunk and came home with it on stupid stuff right so dumb right but she's dealing the poor girl's dealing with hormones and babies and she's got to deal with you know glitter on your face when you come home it's too much yeah and i'm messing around too like for me it's like i don't know why i can't just uh settle down and just try to make this work the right way but well i think you were two years young. I mean, you just lost your virginity. Like, how many girls were you with? Like, I think you need to get that shit out of your system before you settle down with somebody.

And that's, that's most people. Yeah, I mean. That's why all the older people, okay, people in my generation are fucking divorced, okay? Because they married people, like, in their 20s. And if you do marriage math, I call it marriage math. And you say, like, oh, I figure I'll die around 85. And then you add in the time, or you minus the age. you get married at,

whatever that equals is the amount of time you're going to be with one person. Now, I don't know about you, but that makes me slightly claustrophobic if it's any more than like, you know, 12 years, you know what I'm saying? So, I mean, come on. And people are living a lot longer nowadays. In my days, people would be like, if someone died at 8,

you know, 65 or 70, you'd be like, okay, but now it's like he only died at 69. He's so young. You know, like, so you can't get married in your 20s. And so I think you were just, you were young at that time. That's why you couldn't keep, you know, with one person. You were just like, like all the floodgates had opened for you. You're finally having, like, interesting sex.

Like you said, like the second girl was so hot to you because she liked to do different positions. You know what I mean? Like, you had just started because there's even so much more than that out there. Right. And you really, I mean, I just keep teasing it. but like you really wound up, wound up really opening up a lot of doors and going after and doing a lot of things. So you obviously had a lot of stuff inside of you that you wanted to explore. Right.

And, you know, during this time, that's when Craig's list was booming. So going through the personal sections, you know, I even explored, you know, the same-sex personals. Give a word. Okay. So here you are, okay, I need more information, right? Here you are. Now, how old are you, like, the first time you're going to hook up with another guy? Oh.

Do you remember? Probably 23 or 24, somewhere around there. Okay, well, so when did you realize that you were, like, kind of hot for a guy or, like, was it, you were watching porn? And every now and then, that kind of excited you. Like, I mean, how did you, when did that itch start? I wouldn't say hot for a guy per se. Like I don't see a guy and say, oh, he's hot. No, but just like hot to like have sex with a guy.

Like what part of it up? Were you watching porn? Like, you know, how did you know that you were curious? I think it was when AOL Instant Messenger was around. And they had the chat rooms. And then they went away and then Yahoo Messenger came around. and they had chat rooms. So, like, I experienced these chat rooms, you know,

and I was just intrigued and curious about it. So just chatting with guys and everything kind of intrigued me a little bit of how it would feel and how if it's something I want to pursue, you know, just the curiosity of it. Yeah, you sort of dabbled in it online and from a distance for many years, I would assume, before yeah then you know you hear about Craigslist and the personal ads and stuff like that yeah and then you start looking at guys ads yeah and then you see your city you know your location and you're like oh you're able you're able to meet up so yeah so that was kind of the point in time and so what did you go looking for and who did you find and what happened on that first experience

I met this older gentleman who's in his 50s or so and he was kind of in the same boat I was or so he said at the time you know curiosity so I was like okay he's curious I'm curious so there's not like there's an even playing field on there so I met up with him he lived in the same actually same city as I did probably like a couple miles from me. So, uh, went over to his house one night and, uh, all we did was just oral, uh, both of both gave blowjobs to each other. Yeah. Mm-hmm. Mm-hmm. And, um, I remember telling myself after I left that night, I was like, no, it was

the same for me. Right. Uh, but. And how come, how come your, like, was it not that great or did you feel freaked out? afterwards? I want to say freaked out. I would just say kind of like gross

grossed out or ashamed of myself maybe. So it was more afterwards. But during you actually enjoyed it? But yeah, like during it, you know, your horny and your adrenaline's going. You kind of really don't think about it until after. Well, I think, yeah, right.

I always say, Well, that's why I asked because it could be two reasons why you didn't like it or you said it's not for you. Like one is that you actually did it and you were like not turned on and it wasn't even actually that good. And you were like, wow, I'm not really that attracted to men. Or it was the scenario where it was really fucking hot. But the minute you came and were done and you're back in reality, you're like, holy shit. This is not cool. You know, that kind of thing.

And so it was more that scenario. Yeah. Okay. definitely we kept in touch after that because you know we all get horny again yeah right that's what happened

and then did you see him again well I was honest with him and told him I was like you know I don't want to perform anything on you but you can perform it on me and he was like okay okay so it was just strictly him giving me blowjobs were maybe two or three times.

We met up. But then I kind of ghosted him after that. Right. So go on. But that was it for that person. He still tried to message me and text me after that. Of course. I just ignored him.

Yeah, listen. I mean, you were like half his age, right? Yeah. You probably, you know, for him it was a good score to have you around. I'm sure he must have, I'm sure he found somebody else later. So anyway, so go on with you. All right. So that's the first guy that you hook up was. Right.

When you take it further. Well, it went probably, I kind of got, he was more of a masculine guy, and I kind of went more feminine type of a guy. Mm-hmm. I think the next couple of guys I was with were more of the flamboyant, thin, clean shave. And that was a little more better, a little bit better as far as, you know, not feeling so grossed out about it. So you felt like, okay, afterwards.

And even during, did you prefer that kind of guy? guy experience? Yeah. Yeah. I got right. Okay. And now were you still finding these people on Craigslist? Yes. Mm-hmm.

Mm-hmm. Yeah, we, uh, I even, I think it was the third guy actually topped. Mm-hmm. And that was my first time to, you know, have penetration six with a guy. Right. Uh-huh. And are you a top or a switch? Have you been a bottom?

Like, what's your deal? I've tried bottoming and no it's not for me so you like the you like the top maybe that's why you prefer people to just blow you too you're more of you know that's your role yeah and like I said like if I'm with in a relationship not a relationship

but a hetero partnership or seeing somebody a girl and we're having consistent consistently good sex. I won't even think about men or get blowdrops or whatever. Right.

But like, it's just the point when maybe I'm not getting any for a while. It's just easier to go and get a blowdrive from a guy or somewhere else like that. Mm-hmm. And so that's where you typically, that's when you go looking for the guy, is when you're lacking, like, the female companionship

or just a girl that is. Is it a regular in your life that you're having sex with? Yeah, just like a regular flame. Mm-hmm. Yeah. And then, going in chronological order here. Yeah. And then I start hooking up with trainees.

So I'm getting more into the feminine type. And did you go out strictly looking for that? Because you had, like, Google, that kind of porn, and you were like, Hornyford it was just like something new maybe to be to do well I mean on the Craigslist personal that's back then they had the you know the sections yeah sections they have the trans section so you went and look there I click yeah and they had the pictures display and all that and I'm like whoa I mean it's just like a chick yeah kind of for a guy right who likes women and sometimes likes a man wouldn't that be the best

of both world. I mean, you know what I mean? You got it all right there. Yeah. I mean, for me it works. Yeah. And when I had that experience, it was a pretty good experience, you know. In what sense? Because you really, it was like really hot like the hottest experience because they were trans? Yes. You know, her tits were big and she was kind of slim.

it was just she was a she was not hairy not masculine at all so it's just like being with a you know

a chick right uh huh and then you top her him yes yeah yeah and performed oral on her

and she performed oral on me and we did it all right so it's pretty fun we did we hit it off pretty good and had

regular meetings probably like once week or so whenever she was available right and now were you dating all during this time that's what i thought i wasn't dating during this period okay um but shortly there after that me and my kids mom right that's what that's what i remember is like you guys are always trying to work it out right And we saw each other too During this all the while you're seeing these other guys right Yeah

We saw each other too like I'd go over there Take care of the baby or She would drop the baby off to me And sometimes I would just hang over there Watch a movie and then we would have sex And so we kind of saw each other On and off again but never really tried again for a relationship per se

with her right well didn't she catch you though cheating again with like a cross dresser or something like that she caught me she caught well this was this was a point in time no I didn't marry her

not got this one what I didn't marry this one this is the one of the older two kids mom the what? This was my older kids mom. Oh, how many kids and ex-wives and baby mommas do you have? I only have two baby mamas. Okay, well, when did you meet the second girl and have a baby?

Did I miss that? No, this isn't until recent. Oh, okay, so the second one, the one recently caught you cheating on her with a cross-dresser. Correct. Oh, okay, so we haven't gotten to that. Because I remember that. Okay. Yeah.

I mean, so you're back and forth, though, with your first baby mama, right? And you guys try and make work, but it never really lasts, right? And then you eventually meet a new one and get somebody else pregnant. Well, while I always experienced that first transgendered female, and me and my baby mama were, you know, seeing each other on and off, she ended up getting pregnant again. Okay. By me. Mm-hmm.

And had my daughter. Okay. So we tried to make it work again for our relationship. And that only lasted probably three or four months. And it just went back to the same old thing where I just couldn't commit to that one person as she wanted, you know. Right, and you knew that, but that's good, because, I mean, I think I gave you a whole little speech

in the beginning, not even knowing really who you are just because of about, oh, why can't fucking people just be single, you know, it was more general, you know, but I directed it at you, but, you know, you come to that, you come to that realization really early on, right? Like, I mean, it's not like you stay in long-term relationships and really have a lot of affairs.

I mean, you sort of realize it, like you said, like three months in, you're like, Like you can't. You're not into being monogamous. Yeah, but I go back and forth throughout after that. Like I had like an 18-month relationship with somebody, a year and a half relationship with somebody after that. Uh-huh. But they didn't go beyond that, you know. Right.

And then eventually my ex-wife. it all came down. I mean, I was when I was in those exclusive relationships, I would still be seeing people on the side and men and even women too, right?

Yeah, I was about to say, even like strippers in a VIP room, so I dated strippers on the side. It's a pretty dark period for a few years. there. Really? In that you were always just having this like you're always cheating on people. You mean that way? Like what was dark about it? You know, was it the fact that it was like with strippers and

always in the back of a fucking thing and with Craigslist people and behind people's backs. Like that what was so dark about it? Or is that because you were lying? I guess because of everything you said. Yeah. All in the one. It just I would thought I was going to be a better person than this. Yeah, yeah, yeah. It's kind of like how the cards unfolded for me. So I'm learning to deal with it, too. I guess it all boils down to self-control

and being honest with somebody, and I just didn't have either of those. Right, but the problem is, is you would feel bad about it, obviously. Oh, yeah, yeah. Right? I mean, because, listen, there's some people that live your life

and they don't have a fucking thought about it. Do you know what I'm saying? Like maybe 20 years later or whatever. But I mean like you weren't even while you're doing it, you're not having fun, right? Like I mean, I mean, you're having fun, but you're always regretting it or you always are feeling bad about it at the same time, right? Yeah, like I don't feel regret until, you know, after it's done. Right. You're scratching the it.

Something pulls you. You almost feel like you don't have control of yourself. You do it. And then you're like, fuck. And it's like, and every time you just like fail and you're trying not to, right? Like some part of you doesn't like to do that, right? It doesn't want to do it. But then it's like you're splitting too.

It's like you got the angel and devil. Yeah, yeah. Mm-hmm. Mm-hmm. Yeah, listen, because I talk to people all the time that are doing all kinds of things, you know, and I think that there's, like I said, some people that are doing all this stuff and they wouldn't think twice about it. You know what I mean?

But, you know, but when you do feel bad about it, like, that's when you really need to fucking get your act together, right? Right? Because it is, like I say, like I do believe that you make up your own sort of morals and values, right? Whatever is right for you. And so, and when you're going against that, that's when it's wrong. You know what I mean? Because it's wrong to you. Not to everybody else, you know? Because you don't feel right about it. Mm-hmm. Yeah. Correct. Yeah. So go on. You know, after my daughter was born, that's when, as I said, you know, the strippers came, and then Craigslist went away. A few years after she was born. I can't remember exactly year Craigslist went away, but then Grindr came up and, you know, I got on there, and I was able to, it was an easier way to meet up with, you know, femme guys and transsexuals and, you know, just trying to feed my urge and whatever I was feeling that day

or whatever sexual preference I was wanting that day, I would go and choose sometimes, you know, whatever came first. Whatever you mean popped up first? Whoever messaged me back first. Oh, right, right. So whether it was a man or a trans woman or something like that, is that the stuff that you were like looking or a regular, like a, what would you call it a cis woman? I mean, or is that like your choices?

No, just like the, just a transsexual, just a transgendered woman that was my only person who I had interest for. Oh, that's what you were looking for mostly on Grindr. Mm-hmm. Like the more feminine the better. So I would start with trans and work my way down to more thin type of guys. Yeah, yeah, yeah. I couldn't find any trans.

And, you know, there's a lot of nasty prostitutes on grinder and stuff. So you have to weed them out. And I'm not about to catch anything. Yeah. Or anything like that. Mm-hmm. But, you know, you just have. have to weed out the people who are just trying to bullshit you.

Because you wanted the real deal. I mean, you were looking, I mean, you were probably paying for the strippers in the VIP room, but you didn't want to pay for the trans women on Grindr. No, I'm like, I'm just real skeptical about, you know, who's real, who's a undercover cop and all that stuff. So I just, as a typical role, I just, just don't even bother with it. Right.

You know, because at some of these strip clubs, you know, you could go to the VIP room, pay $150 bucks and have sex. Oh, really? With the strippers? And do they pocket that cash, or do you think they have to split it with the, you know, where they work? Or is that, like, on the down low even for them? They pocket.

They pocket the whole thing. Right, right. Oh, yeah, right. There's a door guy. There's a door guy there. Yeah. I'm sure they give them a little bit of it. But you pay like 50 bucks to go back there.

Yeah. To the house. And then you pay the stripper 150 bucks. So it's like $200 in total. Mm-hmm. And do you use condoms? Oh, yeah. You'd always do, right?

So you have them on hand because you know, you go to the strip club and you could get laid. Oh, yeah. Right. Interesting. So that always... Most of the time they have them too. They have the...

Oh, in the rooms or whatever? The strippers do, like, in their purse or locker or whatever. Mm-hmm. Okay. Yeah. I'm assuming you had some... I mean, did you ever date any of the strippers? If you were, like, such a regular.

Did you have relationships? Yeah, I dated a couple. Mm-hmm. I did a couple had a pretty good relationship with one for four or five months. Right. And then she ended up ghosting me. Right. She didn't find out that you were cheating on her, did she?

No, I actually wasn't with her. I actually didn't with her at all. Okay. So she just goes to you. Do you know why? Well, I find out she ended up moving to the East Coast. with, I guess, an ex that was in the military, or maybe she was cheating on me or cheating on me.

Yeah, yeah, yeah, right. Whatever. Right. Did you ever feel like, and I don't know if you're, I mean, dating a man or a trans woman, like in having a relationship? Have you ever, did you ever? Or have you ever thought of that? I have with a trans woman.

I met her off a grinder and we had relations a few times. And then we would not talk to each other for a little bit and then reconnect. And it was an ongoing thing for about a couple of years. And I always wonder, like, you know, what about a relationship thing with a trans woman? and I think the only thing that's really, you know, holding me back is just like, as everybody probably is, you know, what would other people think in my family and friends and, you know, all that types of things. I know, like, you shouldn't really let that influence you, but. But it's there. It's hard.

Yeah, yeah, yeah, of course. For sure, yeah. But that would be your ultimate. And do you think that that would make you the happiest? I think not being in a relationship would make me the happiest. Wait, we still haven't gotten to your marriage. I was wondering if an hour was long enough. Yeah, it's long enough.

We're only at 30 minutes now. So you had that, like, when you were on and off again or seeing that a trans woman for a long time, right? That's when you started to realize that you could have feelings for a trans. woman, right? And that would be ideal for you. But so then is it around that time? And now you're always a top, right, with all these people? Yes. And that's what you're down for. Now, when do you meet that, let's get to the wife, right? Do you meet her around, and you have another baby with her, right? I mean, when do you meet her around this time, right? I meet her. How many years ago? I think it was three years

ago in 2018, so a little over two years ago. Okay. And so do you have a baby with her and that's why you marry her or do you marry her and have a baby with her? Well, we met each other like in October and then we ended up marrying in March. Okay. Why do you get married so soon? I don't know. I mean, did you just think you were so in love? Yeah, I mean, she was really a good person and good influence on my life.

So I was thinking, okay, maybe this would be the one to calming down and keep me grounded. And I can have so-called, you know, air quotes, normal life. Yeah, yeah, yeah. You had that part of you that was really always wanting that, right? That's the part of you that always felt bad about what you were doing, right? So here's the perfect girl sort of offering you that. Mm-hmm. Yeah.

And for the most part, you know, I was. Yeah. I would flirt every now and then with somebody at work, but she was harmless. Harmless flirting. But for six months there with her and then after we got married, it was pretty much monotonous. For how long? For about six months. Okay.

You know. You're like, oh, and I was so, it was really good with her. six months yeah that's the thing like yeah that's the thing like if I'll go a period of time you know a few months

six months with somebody and then I'll just go back to you know my old self right you know so six months into your relationship with the one right you thought she was the one right you marry her really early on

you're like that she's so great she's a really nice girl now did she get pregnant right away she got pregnant probably a few months after we got married okay so and then six months into it though what happens how who do you meet or

do you go looking is the itch come back and you're like I got to fucking scratch it like how does it happen that you cheat on her yeah basically the itch came back and so I got on Grindr and looked and now you said

you know you said like if every Everything's great sexually. Like I don't really go looking now. Was it because she got pregnant and she wasn't having, you weren't having that much sex with her? Like what was going on there that made you start to go look? I guess just we weren't having sex that much. And I'm not saying that because I think that it's like you should blame the other person, right?

No. Because most people, right? But I ask that only because I want to see if that is the real reason why. why that thing sort of pops up for you all the time. You know what I mean? Is it that? Is it something else? You know, so was it she,

it really was that you guys, your sex, like, kind of stopped or waned because she was pregnant? Yeah, it didn't slow down, like, all that much. It was just, uh, I guess it just boiled down to, like, it was just an itch that I had and just, right, that's what I was getting at that. Maybe it's not just when you're not, like,

because you said, if I'm with a girl and, you know, the sex is really good and everything, like, I'm fine. But I don't think so. I think that there are two separate things that are happening. You know what I mean? You have that even if the sex is good. It's not a trans woman, right? Or this other thing that you're really into and that starts to come into your head, right?

Because it's something that you've done and it's something that you've liked and it's something that you're lacking because you haven't done it in six months. Correct, yeah. Right. So you start looking, right? And then you meet up with a cross-dressor? Is that when that whole thing happened? Do you meet up with a lot of people before she catches you? Like, how much do you cheat on her before she catches you?

She was actually the only one. What was that? Just one? Yeah, just one. Oh, my God. You're like sloppy, you with the lipstick on your face. How did you get caught with the cross-dresser? Oh, it's the famous iPhone.

watch. Oh, why? I don't know much about iPhone watches. What? So you have an iPhone watch and a text comes in and it's like right there on your breast and she's sitting right next to you. Oh my God. Yeah, basically. I was talking to my dad on the phone. We were actually on vacation when she found. Was your child born or like is she still pregnant? She's still pregnant. Right, right. She's still pregnant. Now, first of all, let's just start off. Like, let's get a little bit into this cross-dresser, right? Because you've always been with trans women. It's the cross-dresser just somebody that just popped up like you said

and you're like, okay, that's kind of interesting. And I mean, how did you wind up meeting up or having an affair with a cross-dresser? You know, basically, she, basically just what you said, you know. I messaged her because she looked pretty pretty much like a chick.

Right. It didn't bother me to me, bothered me too much that she was a cross-stresser. So I messaged her. Mm-hmm. Then we met up. I met up with her before work. And that day, we were going out of town after work.

And I was just talking to my dad on the phone. She was right next to me. The text popped up on my phone. And, you know, she wanted to see my phone and my watch. But how come? Like, let me ask you this. because if you trust somebody, like, why would you be going, like, let me look and let me see? Like, why was she distrustful of you already for some reason?

I mean, why was she checking your watch or your phone? I don't know. Like, she never really done that before. She said she had a suspicion or feeling. See, that's interesting, right, don't you think? It's interesting. Women's, like, women's intuition, they call it, quote unquote, right? Because here she is not.

because, you know, this is the first time you're cheating on her, right? I mean, she doesn't know that you're a cheater. She doesn't know your history, right? You didn't tell her your history, or did you? No, I haven't told her. Well, she knew about my kid's mom and how I had an affair. Oh, all right. Well, that might have been a little bit in her mind then.

Okay, so you're getting, your phone is beeping or blowing up, and she's like, let me look at your phone. Is that what happens? How does she? It really wasn't blowing up. I mean, it was literally like two tech. you know and she said like I want to look at it yeah and did you know what it was because you saw it on your watch is that how it goes well I knew I was like I deleted the text from my phone but then right then in there I realized well I didn't delete them from my watch okay this is two separate things right

um so right new I knew I was fuck why she wants to look at your phone did you give her your phone yeah I gave her my phone yeah And then she said, give me your watch. Oh, you were fun. And, yeah. She was smart. So. I decided to play the honest card and just try to see.

Well, you didn't decide. Listen, you didn't decide to play the honest card. You were so fucking busted. There's no honesty in what you did. She just, she caught you because it was right there. I mean, you mean, honest in that telling her, like. what the truth was of what she was seeing, right? Is that what you mean?

Well, I could have just not showed her my watch and it could have ended right there. Well, that she would have known something, but you decided to just come clean is what you're saying. Yeah, yeah, yeah. Okay, so you give her the watch, oh my God, and what was in, like, what did the guy, what did the guy had said to you?

Like, what was in there in the attack? Well, she read about a few of the messages that was pretty incriminating. You know, it's just like, hey, come over. I want to suck your dick. Oh, my God. And what was this person in your phone as? Like, who is this person that it's coming from?

Like, does it say a woman's name or a man's name? Because that's like a doubly fucked. She's like doubly like, what the fuck if it's a guy's name? No, it was just Sky. Sky. Oh, okay. She called her herself Sky. Okay.

So it's a woman. She's thinking that this is a woman, right? Mm-hmm. Okay. Did she ever find out that it wasn't a woman? no she didn't okay because that would have been even more hardcore right as far as like you know for her to find out right so she no she yeah she saw about half of the the messages and i grabbed the watch and then deleted them right there and then she got you know pissed off of course because i deleted one oh yeah that was the honest i decided to take the honest route I'm so funny.

Well, I played it like that. I would rather, in my mind at that moment, I would rather played it out where to see how it went versus her calling me out, having sex with a dude or anything like that. No, that would have been much worse for you, but also much worse for her. It would have just opened up a whole other thing, right?

But does she break up with you immediately? Like what happens? Well, like I said, we were about six hours away from home. Oh, yeah, you're on vacation. Oh, my God. And she wanted to leave right then and there. And I had just drove six hours. And I said, look, if you want to go home, I'll take you home in the morning.

And she's pregnant and she's on vacation. Oh, my gosh. This is not good. No, it wasn't good. So you're like, I'll take you home in the morning. and what how did you go home well she packed up all her shit and put it in the car

and was about to leave so I was like okay so I got in the car and she's like I can't drive like this I was like well I can't either because I'm about to like pass it out fall asleep and I'm not driving six hours back like on no sleep

yeah you want to you can sleep in the hotel room and I'll sleep in the car whatever you know whatever yeah she was like no let's just go talk so we went and talked and

she was still living and pissed off but she didn't want to end things right I mean like the poor girl I mean she's newly married she's newly pregnant I mean that's a tough position for her to be in

yeah you know people could understand why she would try and make it work the first girl I would say no right because you guys, like I said, she was young. There's nothing invested there. Here, you had just invested in all these new things, right? It's a new marriage, a new baby coming.

And did you, like, want to make it work too? And did you just say, oh, like, what was your sort of, what did you pitch, how did you pitch it to her? Like, oh, this was a one-time thing. Like, I mean, didn't she want, like, details? Like, where did you meet this person? Like, what was your story that you gave her? Well, I was just vague on everything. That must have drove her crazy

She wanted to know where she lived She wanted to know You know her height Wave Everything Yeah Pictures Yeah

I didn't have any in my phone Thank God She might have seen the Adams apple Yeah You could have showed her pictures Of what of the sky you couldn't have shown her pictures

oh no so but what was like what did you say like you know I'm a girl I know I would have been like where'd you meet this person who is she like what you know where did you say you met this person like what was a story that you conjured up I told her I met her on the

because we met on a dating app yeah so I told her that you know before we came together you know this was just like an exit line and we just had like a one-time flame. All right. So that was the story you threw out there.

Okay. Yeah. And so that was, she was like, okay, let's try and make it work. Mm-hmm. But it never worked. No, because it was too many restrictions on me and rightfully so. Right. As far as going through my phone whenever she wanted.

And now you really, listen, she really was the perfect girl for you if you really want. to stop, right? And, like, be the person that you said, she was that girl. Oh, I know. You know, those restrictions, but you just couldn't, you were not able to do that. It just wasn't me. Right. You couldn't, you weren't ready to not sleep with other people. Right. Mm-hmm.

You know, even, you know, you can't force yourself to be a person who you're not. Right, absolutely. That's what I failed to realize until now. Mm-hmm. And so now how long after did you guys, like how long after she caught you, did you guys last? And then you guys, did you get divorced? About a year. Oh, so you stayed a year.

A little over a year. Right? Yeah. And then you guys got divorced. Does your first girl know about all this stuff? Because, I mean, she was probably felt very vindicated that, you know, you cheat on somebody else too. She's not the only one. Like, does she know?

Because, you know, she has two of your kids, too. so you obviously stay in touch with her, right? Are you guys friends enough that she knows what happened with this one, or is it on the down-low? Actually, my kid's mom is like, we're pretty much best friends. Right, right. I figured you do. So she knows everything about me.

Yeah. Does she know that you're with guys? Yeah. Okay, so when she found out about you being with other people, she knew it was men? Yeah. Okay. And so did she, so when she,

She found out that you did this. Was she like, oh, my God, you're just a fucking idiot. You know, because she just knows you. Yeah, basically. Right. Yeah. You know, she's been pretty cool with it. She don't out me or anything or anything like that.

She respects you, right. Yeah. Well, you guys, at this point, you guys have known each other a long time, right? You've been through so much. She, you had cheated on her. Like, she went through all that, right? All that stuff is in the past. But, you know, I think when you could work through all those things but stay together, you can develop a friendship.

And it's great that you guys are that way, considering you have two kids together. You know, that's the best way to be. Are you still, are you close with this girl now? I mean, you know, you guys divorce, right? You're not going to leave totally because you have a child with her. Are you guys friendly at this point now at all? No. No.

It's on the opposite end of the spectrum. Oh, she fucking hates you. Yeah. How come, because of the cheating or did you not, were you not like, I mean, after you got caught, like, were you a good dad to the child? I mean, I've always been an excellent dad to. Yeah. Because she had a son previously. So, you know, we were always doing stuff with the kids and everything like that.

And even with our baby now, it's, you know, like, take care of her and do everything right. is just, and she, she respects me as a dad, just not as somebody who she wants to talk to. Well, let me ask you this. You know, you cheat on her. She says, okay, let's make it work and decides to give it, like, her best. Who winds up breaking up the relationship a year later? I do. Yeah, that's why she hates you.

Yeah. Yeah, because she's like, I'm willing to put up with your cheating, and you still. fucking leave me like do you know what I mean like it got to a point where you know we were I mean it was pretty yelling at she she would get in my face and yell and it was just I didn't want to get to a point where it would escalate to anything if it even would have so I just ended it. Because you know you did the right thing. you did the right thing but I but that's why she you know still has resentment right because that kind of she even said that it was a good thing yeah because she's just she said like she

didn't have the guts to do it exactly you did it for the both of you but it still will bother even though listen just human being like behavior is it doesn't fucking that still doesn't matter even if you know that in your brain. Do you know what I mean? Your ego still gets burned by shit like that. Like who did it first? You know, like that kind of stuff is stupid bullshit stuff. But we all have been there, felt it.

I understand it, you know. So I could see why she has had a hard time getting past the stuff, you know. Maybe give her a couple more years. Oh, yeah. Hopefully so. Yeah, I mean, you have a child with her, so she's not going anywhere. Has she ever, like, remarried or anything? No, this was just recently.

How long? Last year. Oh, it's only a year. Yeah. I don't know why I'm thinking we're like three years ago. Oh, so yeah, it's just too early. That's why I'm sure that other wife that you're so close with now a year after things weren't so great, right? I mean, it's like it doesn't happen magically that you could.

What was that term, Queditha, you use couple, like, you know, unconscious coupling, like, you know, or conscious couple. You know, where you stay close and. and friends. I think there has to be a time where you're allowed to hate each other and do all that stuff. That's normal human being feelings that you have to allow and go through. And then when you come to the other side of that is the when you can unconsciously uncouple or whatever the fuck it is, where you, you know, you decide to be cool with it. But I think, you know, it's a hard thing to get passed in just under a year because it was, you know, it's not just the cheating. I mean, she was married. lot of things. It's very loaded for her, you know? Yeah. So now you guys break up and so now for the

past year have you just been like going crazy? Have you have like is that itch to actually date? It's a trans woman like something that you you think more and more about? Um, I don't know. I'm just kind of feeling it out and uh but yeah going crazy. I don't know about going crazy. Oh yeah, COVID. I forget. Yeah. COVID happened. But I'm not too, like, I'm not too worried about the COVID stuff, really. Have you had it and gotten over it or because you're young, you don't, you're not afraid of it or do you live in a place where? I had it. Oh, you did. Okay. So you've been there doing that right. Back in August, I think. Right. Did you get really sick or were you not so bad just the sniffles? Because I know, a lot of people that had it were just like, you know, I just felt kind of tired.

Yeah. Drain, tired, fatigue, you know, never lost taste or anything. Right. So have you been hooking up? Like, who do you typically hook up with now since your breakup? Well, I basically used Tinder, Bumble, and Grindr. Yeah. So those are kind of the three apps, and they keep me busy.

Right. And do you see a lot of different people? Like, or do you like variety? Do you like to keep the same ones? Or like, do you see, like, how many people a month do you see around? I have a few regular people that I met off Tinder. A few people off ground here. Probably a amount of month.

Probably like five or six people. Right. And are they all men? Are there women? How is it broken down? There's only one guy. one trans that I'm talking to. I haven't hooked up with her yet.

But the others was off of Tinder, some females off of Tinder. Right. Now, are you looking, are you glad that you are you finally at the place? And I think maybe you said in the beginning, are you finally at the place where you're not looking for that relationship and you're just keeping yourself single so that you're, you can do whatever you want and don't have to feel bad? Well, my, I guess the place I'm at now, it's kind of like, I want to be single,

you know, I need to be single. My brain's telling me to be single. And, but it's just for whatever reason. It's something about a relationship that I miss, but, you know. Well, what about trying to find a relationship with somebody? I mean, you're young, like a woman that would be interested, because I talk to people. that have successful open relationships. And I think the other people, yeah,

are much more open to different kinds of things, you know, much more so now. If I can find somebody with a mindset of like an open relationship. But like even with those, there's some rules involved in. And you don't like to follow any rules? You can't even. I don't. I can't have my cake. Yeah, that sounds so ridiculous.

Like, I mean, if you met a girl that you really liked, okay, like, you really liked and she was like and you could fuck guys when you want to you know what I mean but let's do but her boundary was like but we have to do it together and you can't do it like would you wouldn't that be okay mm-hmm

no I don't think so oh okay you're not I mean don't get me wrong like doing it together it would be fun right but you still would need to do that other stuff yeah interesting something about just doing my own thing you know so and there's nothing wrong with that yeah so i'm kind of

like at the point right now like just going to take it easy for a while be single um just just try this out and see how i like it yeah and maybe if you like really the next time you meet somebody that you like if you try maybe try being honest up front about who you are and see where that takes you you you you, you know what I mean? And maybe try an open relationship. I know that you say that oh, I couldn't, you know, because it's not like you stay with any of these people that long enough to really develop

feelings. I mean, how much was your longest relationship with any of these women? Two years. Oh, which one? With the first baby mama? Who were you with two years? The very first relationship that I cheated on with my baby mom.

Yeah. That was about two years. Okay. And then my ex-wife it was almost two years right well the next time you get the itch or maybe you meet someone I think like you know you don't know if two years from now like you might

you know if you start to meet someone that you really like and you're able to have an open relationship with them if you continue to do that and you continue to stay with the person you might wind up realizing if you really care that maybe if you develop real feelings for that person that you would be okay to live with some rules

because you would want to lose that person that I think it could maybe work for you in the future. But I think you definitely should take as much as much time as you can by just fucking being single and doing what you want and, you know, living it out because, you know, and just doing it as much as possible and getting it out of your system as much as you can before you try out. out the relationship thing. And I think if you do that, maybe one day, you can have a relationship that's open that has some rules and you'd be able to follow it.

But now is not the time. Yeah, that's my goal. It's just to, you know, live the single life a little bit, get out of my system. Yeah. And get to a point where, get to a point where, you know, I'm done with that. Yeah.

And you'll know because you'll meet someone that you like. But like right now you don't have anyone in your life, right? That's trying to, I mean, what happens when you meet the girls? Like, I mean, are you straight up with them? that you're not looking for a relationship right now? Pretty much. Right. You know, some I don't like come out and say it.

But I just navigate the conversation to strictly that. Right, right. Yeah, I think that that's good. And I think that how I sort of preface this whole episode in the beginning was how it ended. And I think, you know, you kind of were like a guy that has, you know, wants his cake and eats it too but it's not really right for you you know when you're trying to do

to me when you're trying to be in the relationship and you're trying so hard to be monogamous that's like when you're trying to do something that is like unworkable but now like you're trying to be single and do whatever you want and I think that's more workable for you do I mean like that's

a more realistic goal yeah right than for you to be in a relationship and be monogamous right like you really know that that's not fucking going to happen but I think it's much easier for you to not scratch the itch of going out and having a relationship than for you

to be in a relationship and not be able to scratch that itch to go out and fuck all these random people because that's what you're into and go do your thing and have your fun and maybe five years from now you will be in a relationship with a trans woman because you know you'll you will be okay with putting that

out there who knows you know but I think what's most important is that you're being more true to yourself now by, you know, being single. Yeah. And, you know, I think that's what my quest is right now, just to find myself and basically just live out my life the way I see fit and just see where it takes me and what road to go on and whatnot. Yeah, you already have all your babies.

You've been married. I mean, you've done a lot. You're only like, what, 34? Yeah. You have your whole life ahead of you, and you've done so much that you've checked off the box, right? It's just time to enjoy yourself. Let me ask you one last question.

If you had to label yourself, because I'm so bad with this stuff, right? What would you label yourself? Well, as far as, like, buy. Like, yeah, uh-huh, like any of those terms, you know, are you, you, you know, are you heteroflexible, by, so there's so many words now, right? Like, is there a word that you think that? you would fit into? Label?

I don't know like what label to call it, but I would say I'm straight with buy tendencies. Right. Yeah, maybe that's heteroflexible. I don't know, right? If that, I don't know. Yeah, I don't know. Maybe somebody can leave. Somebody write in and YouTube listening on YouTube.

Can you please give us the name below in the comments? Anyway, listen, what did we call you? I don't remember your name. David David David I like your story I mean you know I don't think I focus a lot on the S-E-X stuff of things but I because I just like all that other stuff because I think it's so real life you know all the cheating and that I just think and it's very relatable you know

and so I just tried to get it all in because it's interesting and I like these kind of conversations because I think like I said it's a common problem you're not the only guy or person It's not to say that women don't have these issues too that, you know, finds it hard to be in a monogamous relationship and, you know, lives with this kind of confliction in them, right? And so I think it's interesting to put it out there. So thanks so much for calling in and telling your story. Oh, no problem. Thank you for having me.

Yeah, no problem. I don't have to edit a lot out, so it'll be good. It'll be up in the next couple weeks. All right. All right. Thanks so much for calling in. 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 There's a cuck queen story. There's a cuck story. There's a gang being girl story. Like I said, 17 stories. And they're all told in the third person. And they're all true. I took the interview and rewrote it in the third person. And I wouldn't really call it like a total erotica book. Think like penthouse letters. It's more direct. It's not so over the top like erotica. I don't really like that kind of vibe, right? But these are true stories. 17 of them. They're really. short chapters, easy read. You could read, you know, one or two and then skip around. You could read the whole book. It's available in eback format, paperback format. And finally, the audio book is available

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