Strictly Anonymous Confessions - 1310 - Sissy Madeline is a Gender Fluid Crossdresser who Hooks up with Men and Women

Episode Date: December 19, 2025

Sissy Madeline is a gender fluid crossdresser who hooks up with men and women and he called in to talk all about it. Tune in to hear all the details including when he started wearing feminine clothing, when he realized he was into guys, when he started buying clothing and what he bought, how and why he came out to people about everything he was into, how and why he now identifies as now as queer, what he went through to get to the point to accept himself, how his parents were very conservative and how and when he found out his father was gay, ahis explorations with guys when he was younger, when he got into bbc and why “smell” plays a part in what and who he’s attracted to, why he’s never had a relationship with a guy, his interest into ruined orgasms and chastity play, his experience with woman and what he enjoys doing to them the most, his interest in being cucked plus a whole lot more.  GET A COPY OF THE STRICTLY ANONYMOUS BOOK! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY HERE: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://amzn.to/4i7hBCd⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ To see anonymous a pics of my guests + get TONS of exclusive CROSSDRESSER and or HOSER episodes and content + hear all the anonymous confessions, join my Patreon Crossdresser tier it's only $8 a month for Hosers and $10 a month for crossdressers (you get also get Hoser episodes too!) and you can cancel at any time. You can sign up here: ⁠⁠⁠⁠⁠⁠⁠https://www.patreon.com/StrictlyAnonymousPodcast⁠⁠⁠⁠ 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." Want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. All voices are changed.  Sponsors: ⁠⁠https://beducate.me/pd2540-anonymous⁠⁠⁠— Click here to take the quiz and  get your personalized roadmap to sexual happiness ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bluechew.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Get 10% OFF your first month of Bluechew GOLD! Use code: STRICTLYANON⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://motorbunny.com/strictly⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Holiday Sale PLUS $50 off! ⁠⁠⁠⁠⁠⁠http://loadboost.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — To get 10% off LOAD Boost by VB Health use code: STRICTLY ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://butterwellness.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — Use the code STRICTLY at checkout for 20% OFF your entire order⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.quince.com/strictlyanon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ — For premium quality Quince clothing plus FREE shipping and 365 day returns! Follow me! Instagram  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.instagram.com/strictanonymous/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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

If you want to be on the show, it's called Strictly Anonymous because they change everyone's voices and everyone's names. You could call me from a phony number. I don't care to know exactly who you are. I just want to hear your true story. So if you got an interesting, true, naughty story that you want to talk about while remaining, remaining anonymous, send me an email, strictly anonymous podcast.com, or just go to my website, Strictly Anonymouspodcast.com and click on be on the show. If you have a confession, you want to get off your back, call my confessions. Hotline, 347, 4203579. That's 347, 4203579. My Confessions hotline can be called 24-7. You have four minutes to leave a message. If you need longer, just call back. I will edit the calls together. I change all the voices over there as well. They all get aired on my Patreon and some of them wind up on a Confessions episode. Now listen, since this is a Fetish Friday episode, what's great about my Patreon is I also have two. separate tiers. Each tier, whether it's the hoser tour or the cross-dusters tier, it gets one

extra episode a month, an exclusive episode. So the hoser tier gets one extra exclusive hoser episode and the cross-dressing tier gets one extra cross-tressing episode and the one extra hoser episode. So hoser tier is $8 a month, cross-dester $10 a month. It's very specific. What's great about that is that you don't just get the episode for the month that you sign up. You get access to all the episodes that I aired before, right? So for $10 a month or $8 a month, you're getting access to probably 50 episodes. I don't know how many years I've been doing Patreon, but you're getting 12 extra episodes a year, a couple of years.

We're talking about like maybe 50 extra episodes specifically on your fetish available to the minute you sign on, which is a great deal. You also get access to my Discord, which. has a hoser and cross-dusters search here as well. Now listen if you're interested in signing up for SDC, which is like the most popular online dating website for adults, it's SDC.com, the worldwide. You can now sign up for SDC. If you use my code 37712, you're going to get a free trial. So if you want to check it out, SDC.com, use my code 37712 or just go to the description and click on the link.

The thing about SEC that everybody loves is it's not just a place to hook up, right? Like you could post picks. It's an online date adult website. But it also has all the munches and the meet and greets and the parties and all that kind of good stuff in your area as well as in every area. So if you're traveling and you want to meet other cross-dusters like you, maybe you could look for them over at SDC. You get a free trial, click on the link or use my code 37712.

Hi, Sissy Madeline. Welcome to the Strictly Anonymous Podcast. How are you today? I'm doing okay. So listen, Sissy is your kink, Sissy name, right? You're into a scissification play, your gender fluid, you just realized that recently, I think. You're into Chastity play. You love BBC, cuckling, all that kind of. I mean, you're perfect for my show. You're checking off a lot of boxes here. You know, Sissy Madeline. I want to keep calling you Missy Madeline, but it's Sissy Madeline. Yes. So Missy Madeline, let's get.

your whole story. Let me just find out for you right from you right now. Are you a single? Are you single? I am. Okay. Have you ever been married? Not married. I've been in multiple relationships. But anyone long term, I only ask that to see if like, you know, if you're with somebody or

have been with partners that knew about like, you know, what you were into. So longest relationship was six and a half years from 19 to 25. Oh, okay. So that was early on. We're going to get your whole life story.

You know, so it's okay. Let's work, like, we'll hear about your relationships throughout the whole thing because we have so much to talk about, okay? So let's go. Now, like, what do you consider yourself? Like, if you're, like, are you a cross-stressor? Do you, you consider yourself just gender fluid? Do you, are you like a sissy boy?

Like, what would you label yourself if you had to? So, gender, I'm gendered fluid, but I play around with cross-stressing. or cisification. Gender bending, I guess. Like if I go to a club. That word doesn't, you know, we just use that word more in the past. I kind of dig it, gender bending, right?

Yeah. Yeah, you're a gender bender. Okay, so let's go all the way back. Like, what, like, what started, like, what was the first thing that you got into early on? Because I'm assuming early on, I don't know, did you start dressing up? Did you start wanting to be a cissy?

Like, what was it that first came up for you when you were younger? So I actually started at four years old as one of my first four or five years old. And I was with a female friend who I think she was eight at the time. And I tried on one of her dresses because we were playing. She was probably so happy. Yeah, we were playing dress up. And like, I just remember, like, the clothing just felt good. And the, how airy it was just felt different and really good just on my skin.

Yeah. And I kind of, you know, played around with my female friends. And if they wanted me to, like, put on a dress to be funny or whatever in elementary school, I'd do it. Yeah. And like every time I did it or they'd put makeup on me or something like that, it just always felt good. So like it wasn't a sexual thing back then, but like looking at all the stuff I'm into now, like that feeling has always been there. Yeah, it's interesting because I think a lot of kids play around like that, right? But for you, it was more than just like having fun, right?

Like something about it was appealing. Yeah. It just felt kind of right. And again, I didn't question it at the time. And, you know, I guess I've never really questioned that until I kind of came out as gender fluid. Yeah. In 2024. And it was just like, oh, I've always felt this way.

I just never put a label on it. Yeah. That's why I think labels are super helpful. Everyone's so anti them. I don't think you need to label yourself forever, but I think certain points in your life, whether it's you at, you know, two years ago or people when they're younger and in their 20s

or somebody like you, like I said, you know, coming into their own. Like I think, you know, realizing and being able to have a label for how you feel and who you think you are is super helpful. And when I grew up, there were like barely any labels, right? And people didn't fit into them.

But so you felt like a fucking weirdo, right? Because there was like two things you could be. Now I think it's great that there's so many labels. People are so anti them. But I think that they're super. helpful. Yeah, well, I've like made fun of kind of the labels when they all came out in the early, you know, teens, because I'm, I'm 36, I'm a millennial. So like in high school, yeah, it was either your cisgender male, cisgender female, or you're trans. I knew I wasn't trans. Yeah.

And so it was like, oh, okay, by defaults, I'm a cisgender guy. And then it's like, oh, actually, all these different levels are really helpful because gender fluid describes me perfectly. Right. You found the one. And that's why all of these need to exist because, you know, there's so many different concoctions. I love it.

I think it's fine. And like I said, you know, maybe 10 years from now, you're not, like, you don't even need to use that language anymore, right? Like, you know, but I think at a certain point in time, they are helpful. But let's stay back, you know, in time. You're like trying all this stuff. You're having fun. You're doing what little kids do. But for you, it's like, you know, you're kind of like, oh, more into it than usual. Do you start like dressing up in private, in secret or stealing any like girly clothes or anything? Like, what do you wind up doing with the, with, uh, yourself when you were younger? Started trying on panties. Let's see, my junior year. Okay. So I was like 16, 17. And I know I definitely. saw it from like porn online and I just remember how like the guy getting off in the panties like

described the feeling of the fabric and I was like I have to try how that feels right and so I stole some of my moms at first and then I went to Target and bought a pair very nervously That's kind of balzy. Yeah, and use those for a while. And then I started shopping at Victoria's Secret, and the ladies there have loved me. I haven't shopped there in a little bit, but... But did you let them in on the fact that you were buying for yourself?

Yeah. Yeah, really? They love that. And they said, like, multiple guys actually do that. or gender benders do that, but hardly any of them openly admit it. Yeah, right. So they kind of liked that I was just honest about it. I was like, no, it is for me.

Yeah, I love that. I think it's like, listen, you know, at 36, and the time that you were 36 is a lot easier than people, unfortunately, that are like 56 now. They could have never done that back then because it was just a different world. But it's funny that they know that plenty of other guys are coming in there and they're just like fucking lying. you were like the first one that was honest about it and you're young i think that that's like amazing yeah no it's been fun always doing that i've always enjoyed that and it's a little like kinky

so that part of me i guess gets you know a little excited there just by being honest about it yeah i could imagine i've heard that it's there's something a little naughty about it right like there's a turn right uh-huh yeah exactly now were you out to any about this or just to the clerks at the Victoria's Secret? Some close girlfriends. You let them know. Yeah. And over time, I've been more open about it.

And now that I, like, we'll go to one of the more kinky clubs in downtown Minneapolis, I'm pretty just open about it with my friends. Right. But this is so many years later. We're still when you're younger, you just told some girls that you knew. Yeah, like my longest-term relationship in my 20s. She knew that I love doing that stuff because I'd do it in the bedroom. And sometimes I'd just be wearing panties all day.

And she was okay with that? Yeah. Yeah. So, yeah, it's funny. I came out as gay, queer, and gender flu. and she's androgynous and asexual, which explains a lot of our relationship. We both realized both of those things after we broke up,

which is funny, but we're friends now. All these years. Yeah, exactly. We're just like, oh, that actually, looking back, it makes a lot of sense for many different things. Go on. Yeah, she was totally okay with it, is my point. Right.

Well, because she probably obviously had her own secrets of her own going down, right? Yes. At the time. So who is she to be judgmental, right? Right. So, okay. So now do you start, like, you did say you came out as gay. So I'm wondering, like, when you were younger, do you have feelings of attraction

towards men as well? Or did you not put that together? I, so growing up, like, going all the way back to elementary school, I, had a crush on plenty of guys. Actually, I remember first grade. Again, it wasn't sexual, but it was emotional. Me and my best friend, we had crushes on each other. And like, when we'd sleep over, we'd build forts.

And we'd literally cuddle naked together. And it just felt good. Again, there wasn't a sexual element to it, but it was just like, yeah. this is me. I'm attracted to this. And growing up, like, until I got into sex ed in like sixth grade and stuff, I just thought everybody was into everybody and you just settled down with the person you fall in love with. You were that open with yourself or that dot? Like, I don't understand where that's coming from that you would just assume that.

Yeah, I don't actually know. No, either? Really? It just, I think I've learned that some people like men, some people like women, I was attracted to both. And I guess I just assumed out of my ignorance that everybody was like me. Yeah. Nobody was really, you know, we'd talk about like crushes, but it would always also be like, girls have cooties. So you can't be attractive.

to them. And it was like, oh, okay, well, I guess all the dudes like dudes. So, and then it was like, no, that's not the case. And everybody's not like me. And that kind of was shitty in middle school for a while. But yeah, there's negative parts to that. But no, it, I became very private about my sexuality after I lost it, few friends being as open as I was. that's interesting. So people even in your generation were like, oh, not into it. Like they, they axed you out because of it. Right. Yep. I lost two of my best friends and I learned one actually was gay. But it wasn't copping to it? You mean you found it way later that turns out, oh my god, and that's always the case. He came out in late high school and then my other friend, I think he got scared

because we had a sexual relationship and I think it was more fooling around for him, but I actually developed a crush on him. Oh, okay. And I was so comfortable with how I was feeling and what we were doing. They were afraid that, like, I'd be open at school. Yeah. Not necessarily about them, but, like, about myself. and they were afraid that by association,

they'd be labeled as a day. So they pushed me away, ostracized me. Okay, but let's get back to like maybe the dressing and the panties. Tell me about that more about that. So that. Because you do have a lot of stuff going on. And you were like, I have a lot of different ways I could go. I'm like, oh, don't worry.

We'll just get your whole life story. But now I realize, like, you do have a lot of different ways you can go. So why don't you just kind of lead? the call. Okay. So, like, again, the panties thing and really playing around with like lingerie and bras and things started junior, senior year of high school. And then I played around with it more in college. And then I was, yeah, openly buying panties and things from Victoria's Secret in, in my mid-20s. And it's kind of just continued on from there.

But would you wear other things? Like, did it, like, was the panties like the gateway jug to skirts and dresses and full, like all that stuff? Or do you ask? Yes. Okay. Yeah. And so, like, I'll only wear skirts or dresses because I'm actually fairly

masculine looking. Uh-huh. So, like, unless I'm going, like, clubbing downtown. or like I'm around my house or going to like a specific, you know, queer party or something. I don't dress up in public. Uh-huh. But I gladly do it in the bedroom with multiple partners, both men and women.

Right. So, yeah. And that's where I guess the turn-on, the sexual piece comes in. and yeah. And then, okay, so when did you start living out your, the turn-on and the sexual piece of it? With that one girl? Yeah. It started with my longest-term relationship and it's just continued on from there.

And basically any partner I've had I've been open about it with. But what about your first experience with a guy? So first, I've only had one romantic boyfriend. and he was much older than me, but he loved me dressing up and thought it was hot as hell, and it would turn him on. How'd you meet that guy? Let's see.

It was Grindr or one of those sites? Oh, okay, so you were like looking and stuff? Yep, and it was a sexual hookup at first, and then we kept seeing each other, and then we had about a seventh month romantic relationship. And yeah, he, every guy, I don't do it with every guy hook up with, but the guys I've done it with have all been into it. So. The dressing up you mean. Yep, the dressing out for, yeah. Listen, if you just put your, I mean, when you were on Tinder, were you presenting as a sissy because I feel like cissies get hit up a lot. Like there's a lot of guys that happen to be into that. Yeah. Yeah. When I've been on, on, Grindr, I mean, when I was on Craigslist and now I sometimes use double list.

Yeah. Yeah, it's pretty popular. The one turnoff that guys actually have is like the fact that I don't have wigs or because I have like a little bit of chest hair or whatever and I'm not completely feminine. Right. You said you look very masculine. They want you to really present as a female. Right.

And it's like, yeah, not there yet, y'all. I may never be there. What kind of sissy are you? Are you classy? Are you slutty? Like, what kind of vibe do you like when you dress up? I'm totally. Oh, my favorite kind.

Yeah, because I love slutty too. I mean, I grew up with Barbie. My Barbie dolls have the sluggiest clothes. She had stripper heels. Like, I don't know why people are so shocked that girls like to dress slutty. Like, Barbie was the biggest slut around. Like, I love slutty. You know, but listen, I think it's really interesting when some, you know,

of the cissies want to be, like, really classy or like dressed up like secretaries. I do feel a kinship with the slutty, cissies. You like the slutty outfit, the slutty vibe, the slitty look. Yeah, since I've learned that there's such a sexual connection to me being a sissy. Yeah. Like, I just lean into the slutty because that's part of the fun and that's part of the turn on. And actually, that's when I'll get hit on by men and women at the clubs I go to. No way.

Like, everybody loves me and they want to take pictures with me and all kinds of shit. I was like, yeah, absolutely. But you're that out when you, well, okay, like when you, when did you get really out with everybody that you will go to a club, like out and proud kind of thing? That's only been in the past, probably since that was 28. Okay. Mm-hmm. So past eight years.

So what happened at 28 that made you decide to, you know, to change things up? Just one, I was fully single and had been for a few years at that point. And two, I was accepting myself more and more, especially accepting my sexuality. Because I've had issues with being gay growing up. And I will say I identify as queer because I'm romantic. into men. So when looking at like a long-term relationship, I only want to date guys. Oh, okay.

That's interesting. Not girls. Right. But having a one-night stand, I enjoy being sexual with everybody. It may not be like intercourse, but like I have, I enjoy sexual things with all genders across the board. Right. You're naughty.

You're a slutty. That's like what a slutty person would be. like, you know, that's the definition of slutty. That's true, I guess. Yeah. I mean, listen, you are, I mean, I do remember you put in there like, oh, I like a very, I'm a porn addict, you know, I mean, do you think that like, you know, this sort of, you know, sluttiness and all this sexual stuff?

Like, I mean, it does come from like all the porn that you've watched and like being so into it at all. I mean, I don't know. You tell me. Probably. I've never really questioned that or like, you know, really. thought about that, but I'm sure there actually is a probability they're connected. Well, listen, I mean, you know, everything in moderation, you know, I don't know when you say like

you're like addicted to porn. Is it a negative thing? You know, like I'm an addict and I had to quit drinking, you know, but there's plenty of people that could drink until they're blacked out and they're fine and they don't have a problem with it. You know, so I think, you know, everything in moderation is okay, you know, and some people say, oh, I'm addicted to porn, but they're like just, you know, exaggerating, you know, if like, but you don't think you have a serious problem with it, correct? So, I do and I don't. Well, that's kind of interesting. If my mental health suffers and I get very depressed, then the porn can become a problem because it's my, like, go-to drug where people, you know, would drink for example or gamble or whatever.

I turn to porn. It's my escape from reality. But when things are going well, like currently in my life, it's not a problem at all. I can control it. You know, if I have two to three hours on a Friday night and I want to goon and just edge myself to oblivion, then great. But like, I won't be on it all day or things like that. Or, you know, I don't need to look at it at work or other things like that. So why would you think you have a problem? Well, because I've, let's see, I think the longest I ever went was a 16-hour binge. What?

With, yep, with, this was back when I was in college, so I probably was 22, 23. Mm-hmm. And there was bathroom breaks and eating breaks in between, but. very little to no sleep. And yeah, I think I went on 16 hours. Wow. Let me ask you this. Did you feel like, like, were you going through a very stressful time at that time in

your life? Was like anything going on that would have made you need to check out for that long of a time for some reason? Oh, yeah. Stress, there was definitely stress. And like I said, when my mental health is poor. or my depression starts getting bad. That's when I check out from reality.

Yeah, like I'm going to have Dr. David Lay on, and he doesn't believe that porn addiction exists. But I think you could become addicted to anything. And because of what I think addiction is is just like a, you know, somebody that wants to, that can't handle their feelings. They feel too intense or whatever. It feels like an emergency and you need to get away from them as fast as possible. And so everyone gets away from them in different ways.

I think somebody that's too into religion could be like no different. than the fucking alcoholic, you know what I mean? That checks out. You could check out with anything. And if you're running away every time you're like dealing with something difficult, like that could be a problem, you know? Well, the thing is, like my parents, they were workaholics. Yeah, there you go.

You know, there's workout addicts or running addicts. Exactly. No difference. It's just in America, we view those things as good so we don't label them as addictions. Yeah, but let me just tell you, you know what I always say? I'm like, they're just like boring addicts. At least I was fun. I was addicted to alcohol. You're addicted to sex. We're more fun addicts. Like, it's so boring. My mother was a workaholic and a Jesusaholic, so it's like, right. And that's the thing is like, yeah, okay, it's, I agree with people when

they say like porn addiction, quote unquote, doesn't exist because it's not actually the porn. I'm addicted to the dopamine. But that's the same with everything. Right. It's just that is the route I decide to get high off of the show. Thank you. You're right there with me. Yeah. Well, you know, you might want to like look into that. You know what I mean? Oh, I have. I have. Okay. That's good. Therapy and everything. Yeah. Well, let me ask you this. Like the two years ago or, you know, in 2024, you really came into your own and kind of like was able to label yourself and everything. Do you feel like, you know, at that time in your life, maybe you did hit a crossroads that was positive? at all? Like, I mean, is that what helped you sort of realize things about yourself? Yeah, I think so. I think since 2021, I've been on a pretty positive journey.

Yeah, especially around my gender and sexuality. Yeah. And do you think that that played a part in your depression and everything, like all this kind of maybe confusion about all the things that you were into and that you were thinking about? Um, so I definitely have. And, you have, self homophobia thanks to religion. And I basically, in the 90s, we were still a pretty homophobic culture. And I just internalized all that. So my depression and hatred over me being gay, queer, has always been linked. Yeah. So the older I've gotten, the more accepting I've gotten, especially in the past eight years. Yeah, that's amazing. Because unfortunately, it was like put on you because you said like,

it sounds like you were raised in a very religious household that sort of hypnotized you into believing that who you were was wrong. Right. And the funny thing is neither one of my parents are actually religious, but we went to church every Sunday because my dad liked to use it for business and my mom like the social aspect of it. Oh, he was networking and she was socializing. Right. But like when the pastors and stuff were freaking homophobic, it's like, well, I'm still going to internalize that, even if, you know, and my dad used the gay slurter F word all the time. Yeah. He actually has become my biggest supporter, and I realized he's not straight either. He's never going to tell anybody that. But, but,

But he's bisexual for sure. Oh, how do you know? Did he caught me to you? He talked to me a little bit, but my mom actually caught him cheated with women and men. She read his emails. We really are going in weird places on this call, but I love it. Sorry. Like I said, don't talk good.

Like I said, I guess it's good. I'm sorry. Wait a second. Do you remember being in the house and your mother flipping out because she's like men and women? How did you find out that it was men and women? Like, how do you know their personal business? Because my mom told me when they, after they got a divorce, she had dirt that she told me about. Oh, my God.

And here it was the guy walking around making all those comments about, you know, people. He was one of them. I bring that up because I learned that he was in love with his best friend in the 80s and his best friend died. in the AIDS epidemic of AIDS. Oh. And he blamed his best friend for being gay. He, like, blamed the gayness for taking his best friend, basically. Right.

He hated that fact that he was gay because he felt like if only it wasn't for that, he'd be alive, and that was his best. Right. That kind of makes sense. And it took me coming out for him to start basically doing his own self-fell. Oh my God, I kind of just got the chills. That's kind of very profound for your father. I feel like, you know, you might have really helped him come to terms with something,

you know, that whole thing that he went through. You know, he might have been able to come full circle. That's like pretty amazing. Yeah. And, yeah, he's only talked to me about his personal experiences, I think, two or three times. as an adult and I was

going back to middle school I was caught being sexual with two of my best friends two of the three best friends I was playing around with at the time Uh huh What for you again? Middle school or high school?

Uh, middle school After I was caught a couple of times By my parents Sleep it around Oh my God Oh my god Both of my parents were like Oh we played around with the same gender

In middle school too You're kids No. They're like, oh, no, that exploring is normal. Right. Okay. And I was like, yeah, I think this a little bit more than exploring for me. It might have been for them too, but in their generation, they couldn't sort of cop to it. Look at your father. You know what I mean? So my point is, neither one of my parents are 100% straight. Right. Don't you think most people are in 100% straight? Well, that's the thing is I think that our culture would be far more accepting if we just told what percentage we were because you're not going to find anybody, well, rarely somebody 100% gay and somebody 100% straight. Yeah, most people fall someplace in the middle.

And it's funny because somebody was doing some sort of graph or like I felt like it was like Pierce Morgan and Tucker Carlson were having this whole conversation about why there's so many more gay people now. And one of them, I think it was Pierce Morgan, was like, it's because they're allowed to be. And they're like being fucking honest about it. And Tucker was like blaming it on crazy shit. You know what I mean? It's like, come on. Yes.

I'd see it because of my show. And I've grown, I've been, you know, I was born and have been alive through these different times. And the only reason why there's more gay people now is because people could be fucking honest. I talk to all the gay and by people that are from my generation that are still sucking dicks and cars, okay? But they existed back then.

You know what I mean? And it just they weren't allowed to raise their hand and say it. Every girl's by. Every guy's by now. And I think that that's wonderful. But it's not like anyone's changing anything. This is just the way everybody always was. I'm using this.

And I'm using the straight term in huge air quotes. But I've hooked up with plenty of straight men on grinder. Exactly. Yeah. And those are guys probably older, you know, that couldn't call to it. And so they'd check off the box that they're straight. And everyone's thinking there's all these straight people, but there never was. It's always been that a lot of people fall somewhere in the middle of that Kinsey scale, right?

Totally homo or totally heterol. And I definitely think there are people that fall into those categories for sure. But I don't think it's the minority. Well, since I'm mainly a bottom and more submissive, I run into plenty of guys. And one of my high school friends was the same way. it's not considered gay when they're not the taker. Interesting. Right.

Okay, hon. Whatever you need to tell yourself. But it's like, I'm going down on you or yeah. You rail me. Yeah. Pretty sure it counts as gay. Yeah. And, you know, that's the problem.

It's the gay word. First of all, it's a problem because there's so much negativity to being gay. And it's like, what's the fucking problem with that? Second of all, it's like, that's not gay. actually anyway, even if you just like to suck a dick. If you don't want to date a guy, then it's not gay at all, right? Like, but why, first of all, why if it was gay is that bad? You know, and that's like there and lies the problem.

It's just like all this sort of stigma that exists with guy and guy action that so much has to be hidden, which is ridiculous. But so I know that you love BBC. Like, when did you start hugging up with black eyes? I mean, was that just something that you always had done or did you have an experience and you're like, oh my God, this is like the best thing ever? So I had an experience senior year of college or senior year of high school, freshman year of college. I think I was using an adult friend finder at the time. And I met this guy with a 10-inch dick. Oh, my gosh.

And I had to kind of train to take it. But when I was able to take it, it was magical. And I just love, I've noticed that I have like huge, my two, like, when it comes to our senses, I'm huge on taste and smell. Okay. And I've just noticed that, like, black guys to me smell amazing. and the guy that I was hooking up with tasted amazing too. Interesting.

And it must be like the furmoons, right? You're not talking about the wearing a specific cologne. It's just like it's like the pheromones that they're given off, right? Compared to like white people or an Asian person, right? Yep. Natural body sense. Yeah, interesting. I just hooked up with one of the gay bars in Minneapolis did their kink night.

they do it once a month and i just hooked up with a guy who was wearing a black guy wearing a puppy mask he was like six four and i licked his armpits he wasn't wearing deodorant and then i went down on him and he had a nine-inch dick which i couldn't fully take in my mouth but no like that's that's just the thing. I was like, you smell and it taste amazing. And then I just blew him and it was great. But it sounds like you like strong smells, right?

Like you like it to be in your face, right? Because if you're licking an armpit without anything, like you want to, you want the scent. That's the thing. As long as you have good hygiene, I am down with it. Right. Completely.

And that's the thing. It's like, if you have bad hygiene, I'll let you know or I'll just be like, no. Right. And that could be anybody. But you find that if like everyone, say there was like a black guy, a white guy, an Asian guy, like, and everyone was clean, you would like the scent of the black guy the most. Yes. Yeah.

That is what I've noticed about me. Yes. Absolutely. Yeah. It's interesting, right? Yeah. And so it's a scent and it's the big dick. Yes.

Have you ever dated a guy? only the one guy I dated who was older than me for like six months right we actually technically only really dated in person for one month and then he moved to texas and it was like a six months long distance like long distance thing where we were both allowed to hook up with anybody we wanted so you know it was whatever was it like a real real you know intimate dating relationship. But you said, though, that that's what you prefer, right? Like, you don't want to be in a romantic relationship with a woman. You want to be in a romantic relationship with a guy. You just have, do you think it's that you just haven't met the right person? You're just not ready for a relationship just yet?

Like, why do you think you haven't had a long-term relationship yet with a guy? Because, one, in my 20s, I tried dating too many women because I think I was still in denial about that I was gay and I was still trying to be like no I'm by I can date both and it's like no no no I'm not yeah and in the past couple of years one was in for medical reasons my mom lived with me in my one bedroom apartment for 11 months and so that was kind of hard to even hook up with people and then I've had some health issues which has made it hard to hook up, but definitely date. And I've decided to get my mental health in check before dating. And in the past year, I'm just having too much damn fun with all

genders right now. Maybe you've been having fun this whole time. Like maybe you have never really wanted. I typically think like whatever kind of life we have at the moment in the past is like what we really want. I mean, sometimes people are running around talking about how much they want something else when they never have it. It's like, what's the time? Like, whatever you have concocted for yourself. And I'm not talking about like extenuating circumstances like if you have a disease or anything. You know, but like if you're single all the time, it's probably like on some level like that's what you want. Because if you really want to be in a relationship, you would. I never had very long term relationships, you know, at all. I didn't want it. You know what I mean? I wanted to live my life the way I wanted. It was way later in life that I thought like, oh, maybe I

be ready to settle down with somebody, but I never really had that desire before that. And I think sometimes people don't understand that that could actually possibly be. But, you know, maybe you just didn't, you know, you were just, you know, listen, you've been trying to figure yourself out. You've been dealing with things, you know, and doing all that work on yourself. And that could be, you know, that could have you looking in a totally different direction. And I did a lot of that too when I was younger, you know? Yeah, for sure. And yeah, it's just now I'm just having, Too much damn fun. Right.

And now you've come full circle and you're feeling great and now you're having fun. So it's like, you know, maybe after you've been there done that, you know, you'll be like, okay, now I'm ready to settle down, right? But maybe you just feel like you're just started, right? Because you're finally like, come to terms with everything. That's kind of how I see it is like, you know, two to three years from now. Yeah. All right.

Maybe I'll, you know, go and do a relationship again. But I'm like, right now, I'm just having fun. And I got stuff. I joke I'm making up for lost time for my 20s. Yeah, that makes sense. Yeah, because you were like living a lie, dating women, not what you want to do at all. Right. And so it's like, no, now I'm just fooling around with everybody I want.

And it's still mainly guys. I see two guys regularly have since 2022. Oh, okay. Are they like your booty call guys? Oh, yeah. Kind of, yeah. One guy, he's into edging, teasing, denial, ruined orgasms, chastity like me. Oh, okay.

It's funny because he always likes for me to edge him instead of the other way around, which is fine. But you like it too? Oh, God, yeah. It's fun, and he eats my ass while I do it normally, and he's addicted to that, it seems, which is fine by me. I like it. And no, it's just we have fun. And then there's another guy I kind of is more vanilla.

I cuddle with. We make out. I go down on him. And yeah, it's a good time. Yeah. Okay. So you have those two guys. You finally come into your own.

You wasted all that time dating women. In the future, you might date a guy. So what is like you get into Chassis play as well as T's and Denial, ruined orgasm, all of the above too as well? Correct. Or just. chastity or all of that. No, all of the above. I actually so addicted if I use that word in a good way here to ruined orgasms. Yeah. I don't actually like jerking off with just my hand and giving myself a full orgasm anymore. I'd rather use like a vibrator in my panties or something like that.

and yeah it's it's amazing I love ruined orgasms they feel way better to me what does it mean ruined orgasms like not being allowed at all or stopping in the middle

what's a ruined orgasm so it's like non-stimulus so you get yourself to the edge and right before right as you start coming you take like all stimulation away and I can come like four or five times in a row that way.

Wow. Because it's not, you're not getting a full release. There's still, it's like, yeah, you're coming, but your body's like, wait a minute, there's a part missing here. Like, and it just increases the dopamine and the pleasure and the, all the tinglingness and sensations in your body. And it's just a heightened feeling of, eventually and it's way better than a regular orgasm where it's just one and done.

I know there's guys that can come multiple times and things, but it's like for me, no, I'm a one and done guy if I'm giving myself full orgasm. So yeah. Yeah, I totally get that. So, okay, let's get now, do you wear panties under your clothes when you're walking around? Do you just fully dress up when you got like what do you like how? what's the cross-dressing or the cisification have? Like how, what's that?

So the, the cisification is mainly, like, when I'm gender bending or whatever in a club, or it's mainly in the bedroom with a partner. Mm-hmm. Playing around dressing up in different outfits I have.

Right. And that's when you're being intimate. Yep. Uh-huh. And, uh, yeah, it's, there's, with certain partners there's a sexual humiliation piece that can come with cystification which is part of the fun turn on to me yeah and yeah it's just being treated more quote unquote girly and more submissive and things like that which is just a huge freaking turn on for me right and yeah it's so that's

part of the fun. But no, I'll wear panties under my clothes all the time. Right. I actually wear more panties than boxers now. So. And how come? Just because it's a turn on, because you're used to the material now too and you like it better or like, I like the material to feel better. I like how it fits me better because I'm not huge. I'm average size. And Yeah, there's also a sexual piece to it for sure. Right. So, and what about other sort of feminine clothing gear? Or do you wear anything other than panties, like bras or panty hose, heels?

I mean, I'm assuming you do when you go dressed and go out, right? Yes. I do when I'm dressed and go out, definitely like pantyhobs, stockings, love some sexy thigh highs. Yeah. I have a short schoolgirl shirts. I have a few bras. I have worn a small bra or two out and about in my daily life. Like I'll go to a mall and things.

And it doesn't seem all that noticeable. And I definitely played around with it more in 2020 and 2021 when everybody was masked. Oh, yeah. Yeah, no, when we were all masked and I could kind of hide part of my face at least. Yeah, I can imagine. Yeah, I was a little bit more bold about it. But, no, it's mainly just panties on my everyday life. And then it's in the bedroom or, yeah, when I'm going out to a party or a club, something like that.

How often do you hook up with women? Is it typically like when you're out and about, do you go and seek them out? because I know that you are down to hook up with women sexually. Yes. So I don't hook up with a lot of women. Right now I have one of my good friends is one of my key holders for my chest V cage. And then the other friend, she's also gender fluid. And she's the one that I had intercourse with in September, which was.

my first time with a female presented woman. And I was more curious. Wait, that was losing your virginity. You lost your virginity of a woman for the first time? Yep. I think I didn't understand. I never.

All that time back then, well, because we know that that first girl, because she's asexual now, she wasn't into sex. So you guys were not fucking. Well, well, we loved going down on each other.

Okay. It's just, she was waiting for marriage for personal reasons at the time that she didn't, I think, fully understand. Okay, and all the rest of the women, how did sex never come up? So it's, there have been a few women that I've dated or played around with since then, and I could just never get it up when the time came. Interesting. So I couldn't get hard enough to actually go in.

side of a woman. So how was your first experience? Yeah. Yep. And it was more just to try it because I was curious. There wasn't even like a huge sexual desire to try it. It was just like, huh, I wonder what this feels like. And I've wondered for far too long, let's check it off.

How was it for you? It's okay. Yeah. I kind of want to try it again, but I can kind of leave it. It's not. It's it. So maybe you're like 95-5 or 90-10. Yeah.

Right? Well, the funny thing is my favorite sexual act of all time is going down on a woman. Oh, fascinating. You're like so interesting. Nothing makes sense. I could live in between a woman's legs. Interesting. I love eating them out for as long as they want me to.

Okay. And it's, again, it's a taste and a feel thing. Oh, right. That's you. Yeah. Yeah. And I've noticed I love hairier women, overshaved women. But I've done both.

But again, it's like a scent and a feel thing. And the girlfriend who's asexual now, she had the most amazing screaming, squirting orgasms of all time and she could go until her body like couldn't do it anymore and so we'd go for like hours wow and it kind of like like that i think got me really addicted to go down on women yeah i could imagine oh oh this is so much fun that oh my god and no it's funny like i joke with especially my female friends, I get bored sucking dick after a while

because it's like you can only do so much and then it's like okay dude like come already or let's do something else Yeah and you feel like going down on girls is totally different Oh yeah because

I can use my tongue in all different ways you can suck in different ways kissing the clit like when it's really sensitive like gets them off and I'm just noticed that you know guys aren't the biggest into or at least the guys I've been with aren't huge into me like kissing their cock or licking their cock or teasing it they're all like deep throat it and it's like there's something more to that

than just deep throat in Jesus. Like come on now. Yeah but you know you're you're doing these like quickies with these guys you know like just pure hookups. Like maybe like when you're in a long-term relationship, you'll take your time and try new things. That's kind of what I'm hoping. Yeah.

That's actually one of the things I'd look forward to. Yeah. Gay relationships. Like, I need a partner who's cool with playing around for a while in the bedroom. Yeah, not these little quickies you're used to having. I know that you said you're like, you haven't tried cuckolding yet, but you are into that. Is that something you think you'd be down to do when you do get into a relationship?

you want to be cucked? Yes. I would love to date a by guy and be cucked by him and like a woman. Oh, I love this. I haven't never heard this before. Or I'd love. Yeah. Or?

Or I'd love to like do a short-term fling or just sexual kind of relationship with a woman over a few months and have them cuckled me. and I'd be their cuck partner. They could put me in chastity if they wanted or not. But like I'd be the helper or the watcher in the bedroom. Yeah. So whether it's a man or a woman, you want to be, you want to be the cuck. That's so interesting.

This is like a first for me hearing this kind of shit. Yeah. And that definitely comes from porn, but God, I fantasized it about it so fucking much. I mean, listen, somebody that's into like tease and denial and ruined orgasm,

Like don't you think the cuck thing kind of goes in in in that right it it lines up with it yeah yeah yeah for sure makes sense yeah totally it's like it like makes it last longer you're savoring it you know what I mean like tease and denial does uh you're sitting there watching and you're turned on the whole time yeah absolutely yeah oh my god let me just tell you I have to wrap it up but like I have to say. I love that there was like, not much. Like, we didn't get like a straight line whole life story here, but we got a lot of information about your sex life, which is very interesting. A lot of times with, I got to say, like a lot of times when I get on the phone with someone who I consider to have a fetish, fetish episodes don't be that. They're not really

that sexual, right? Because it's more about the fetish and what they like and blah, blah, blah. But like your episode was more about sex, really. Which I didn't realize it was going to be, glad that I like you just let you kind of go because there were so many like interesting stories and interesting things that you're into and interesting angles of your sexuality and what you're dig and what you're down with and what you've tried. So I love this episode. I think it's super interesting and people are going to dig it. Awesome. Yeah. This has been amazingly fun and I love talking to you. Yeah, yeah. Yeah. That's fun too. And like I know we both didn't know where it was going to go and it went in so many different directions, but I think everyone's going to be happy because

there were so much interesting stuff in there. So thanks for calling in and, you know, telling me all your stories. They were super interesting. I say interesting a lot, but I mean it. No, I love it. Thank you so much. Yeah. It's been fun. What was your name again, Sissy Madeline? Thanks to see Madeline for calling in. It's great. Yes, absolutely. You're very welcome. Okay. Bye. All right. Sounds good. Bye-bye. Bye. Okay, I just want to tell you before you go that my book, it's called Strictly Anonymous Confession, Secret Sex Lives of Total Strangers, is now available not only in paperback and ebook, 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 talked about on my show. like there's a hot wife story. There's a cuck queen story. There's a cuck story. There's a gang being girl story. Like I said, 17 stories. And they're all told in the third person. And they're all true. I took the interview and rewrote it in the third person. And I wouldn't really call it like a total erotica book. Think like penthouse letters. It's more direct. It's not so over the top like erotica. I don't really like that kind of vibe, right? But these are true stories.

17 of them. They're really short chapters, easy read. You could read, you know, one or two and then skip around. You could read the whole book. It's available in eback format, paperback format. And finally, the audiobook is available coming out August 25th. But you could pre-order it now. And if you buy my book in any format or pre-order it, I will throw in a complimentary link to my Discord. My Discord does not disappoint. Okay. There's no way you get into it. to my Discord any other way than getting the link from me. Okay, I give it to people who buy my book. There's tons of people in there. Everybody shares content with each other. And that's what you get to do there. You could post your own pictures and videos. There's tons of channels. We have lots of

contests where you can win a lot of money. It's a super fun place to be. It's a total, strictly anonymous community and you will love it. I will be giving anyone who buys my book access to my Discord. It's private, like I said. All you got to do is email. me a screenshot of your purchase, whether you did the audiobook, the e-book, or the paperback. Send it to me at Strictly Anonymous Podcast at gmail.com. That's Strictly Anonymous Podcast at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in.

This is the Strictly Anonymous podcast. Did you come here looking to hear some super hot stories? Well, then I know where you can tune in and read a ton more hot stories. And that is in my book. Strictly anonymous confession, secret sex lives of total strangers. It's finally out. It's available anywhere where you buy books. The links will be in the description.

The book contains 17 stories, sort of like the best of from every category I have on my show. There's a hot wife. There's a cock. There's a bull. There's a bunch of swingers. There's a gang bang girl. There's a gilf porn star. There's a girl that fucked her best friend's mom from high school.

All those stories are in the book and they're all true. Think Penhouse Forum meets my show. That's the vibe of the book. It's available anywhere where you find books. The link is in the description. And for this week only, I am giving anyone who buys my book complimentary access to my private Discord, which is super fun. It's a not safe for work site. It's a place where people get to post their own picks and videos. People are hooking up over there. We have naughty contests. It's super fun.

The only way you get in is through me. If you purchase the book, send me a pick of your screenshot. Email it to me. It's strictly anonymous podcast at gmail.com. And I'll send you a private link to my Discord. So if you want to buy the book, just go to the description and click on the link.