Strictly Anonymous Confessions - 1128 - FETISH FRIDAY: Lilly is a Sissy Crossdresser

Episode Date: May 30, 2025

Lilly is a sissy crossdresser and he called in to talk all about it. Tune in to hear all the details including how and why he started being into panties and how that led to fully dressing, how he got ...caught dressing by his mom and how she reacted, how he told some friends in high school and how they reacted and the difference between the guys’ vs. the girls reactions, how and when he realized he’s a crossdresser and not trans, the relationship he currently has with a girl who treats him as her sissy, how and when she copped to being into his crossdressing and his sissy side,  their first hook up and how it quickly progressed to pegging and more, the tasks she makes him do for her, the sissy he met who he now Doms and what he enjoys about that relationship, what they do together online, how often he dresses up now that he lives alone, how he likes to dress and how passable he is, what he’s looking for in his future plus a whole lot more. **To see anonymous a pics of LILLY'S STASH plus see pics my other female 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 MY BOOK IS NOW OUT FOR PRE-ORDER!!!! Strictly Anonymous Confessions: Secret Sex Lives of Total Strangers. A bunch of short, super sexy, TRUE stories. GET YOUR COPY NOW: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://amzn.to/4i7hBCd⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  To join SDC and get a FREE Trial! click here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.sdc.com/?ref=37712⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ or go to SDC.com and use my code 37712  Want to be on the show? Email me at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠strictlyanonymouspodcast@gmail.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ or go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠http://www.strictlyanonymouspodcast.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and click on "Be on the Show" Have something quick you want to confess while remaining anonymous? Call the CONFESSIONS hotline at 347-420-3579. You can call 24/7. All voices are changed.  Sponsors:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://viia.co/STRICTLYANON⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Try VIIA and use code STRICTLYANON for great SEX and sleep ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.dipseastories.com/strictlyanon⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Hear the hottest stories on Dipsea and get a 30-day FREE trial PLUS 25% off your subscription ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://butterwellness.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Use the code “STRICTLY” at checkout for 20% off your entire order ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://bluechew.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Get your first month of the new Blewchew Max FREE! use code: STRICTLYANON ⁠⁠⁠⁠⁠⁠⁠⁠https://beducate.me/pd2512-anonymous⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Use code anonymous to get an additional 10% off the campaign’s current discount - that’s 60% off ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://shamelesscare.sjv.io/xLQ3Jv⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Get $10 off Shameless Care’s female viagra cream, just click on the link and use code: Strictly   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/Strictlyanonymouspodcas⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

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Starting point is 00:00:00 It's called Strictly Anonymous because most people who come on my show, I would say 99% of the people are anonymous. But if you're out and proud about your secret naughty life, you could be on the show too, okay? But I do change the 99% of the anonymous people's voices. You can make up a phony name. You can email me from a phony email. I don't care. Just email me at Strictly Anonymous Podcast.g.m.
Starting point is 00:00:20 Or go to my website, strictly anonymous podcast.com and click on Be on the Show. If you haven't wrote a review for my show, a long time ago, I started begging for reviews. I never did before my life. Now I do. And people write reviews and I love reading them. I just got one best sexy podcast, another one super hot. Everything that you guys wrote in those reviews are so appreciated by me. I read them all and I love them because I work my ass off for my show and it's so great
Starting point is 00:00:47 to know that people are listening and people love my show. So if you do love my show, hit five stars or write a review, it does actually help the show too besides making me be happy when I see them. I don't care about the trolls that write bad reviews. If you want to write a bad review for my show, go ahead. The fact that you took the time out means something. Anyway, if you have a confession that you want to leave on my confessions hotline, I have a confession's hall.
Starting point is 00:01:10 You could call that number 247-347-447-4-203-5779. That's 347-4-203-579. You have four minutes. Leave a message. If you need longer, just call back and make sure you're in a quiet place, okay? Most of those confessions make it on to a confessions episode. and the rest go on to my Patreon. Now my Patreon is super fun,
Starting point is 00:01:30 and 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-dressing tier, 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's here is $8 a month.
Starting point is 00:01:59 Crosschester, $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 years. We're talking about like maybe 50 extra episodes specifically on your fetish available to
Starting point is 00:02:26 the minute you sign on, which is a great deal. You also get access to my Discord, which has a hoser and cross-dustach here as well. And right now, okay, I am doing a whole best pussy pick contest over on my Discord. I did a dick pick contest. You could still see that over on my Discord. It was super fun. I got over like 150 dick picks. Me and Layla went through and rated them. Now we're doing a pussy pick contest if you want to put your partner up for that contest. If you want to join You win a hundred bucks and a clone your pussy kit, but you also see a lot of picks over there. You could get into my Discord through signing up for my Patreon. With my Patreon, you get early and ad-free episodes, plus you get every single picture of all of my female guests.
Starting point is 00:03:11 They all send in hot picks. You also get all of the anonymous confessions, but you also, like I said, get access to my Discord. And my Discord is a not safe for work site. That's a place where everyone gets to join in and post picks and videos and talk to each other over there. It is great. My Discord is super cool. People are hooking up over there. Like I said, there's the Pussy Pick Contest going over there.
Starting point is 00:03:34 There's so many different channels with so much content. Okay. So definitely you want to sign up for my Discord. You could also get on to my Discord by buying my book. I do have a book coming out. I work my ass off for that book too. It's coming out October 14th. It is up for presale on Amazon.
Starting point is 00:03:51 There's a link in my description. And if you purchase the book, pre-order, just send me a pick. And if you send me a pick of your pre-order, I will send you a free link to get into my Discord. You won't get into my Patreon, but you'll get into my Discord and you can participate in that Pussy Pick contest and I run contests all the time. And you could also see all the other shit that's going down there. And there's a lot of stuff.
Starting point is 00:04:10 The last thing I want to tell you about is SDC. SDC is like the world's largest adult dating website. It's not just a place where you're going to meet people to hug up with what's great about SDC and what I love about. is you could find out all the information you want to know about the lifestyle. They also have information on all the gangbanks and the meetups and the munches and the hotel takeovers and the swingers clubs in your area or all over the world. So if you're traveling, you want to go hook up or do something naughty on your trip, you could find out about it on SDC. And the good news is I have a
Starting point is 00:04:43 free trial for all of my listeners. All you got to do is put in the code 37712. That's 3771 or just go to the description and click on the link in my description is links to everything that I just talked about. Now, today I have on Lily. Lily's got a very interesting story. Lily is young, only 24. Lily's a cross-dresser and he's currently like hook it up with two different people and they're very two separate situations. One is like he's a sissy for somebody who doms him and he humiliates him and all that kind of good stuff. There's begging going on and that going on in that relationship. and then she has another relationship with another cissy and he acts as like a dom to that cissy. So he like switches roles.
Starting point is 00:05:29 It's very interesting who these people are. Okay. When you find out who these people are, super interesting. We do go all the way back. He talks about when he realized he was into wearing women's clothing, started off with panties and then progressed to everything. He talks about all the times he got caught, how his parents felt about it. both his parents wind up catching when that he was cross-dressing. So did everyone in his high school. Okay. And he talks about that, how everyone knew. He always was into being a cissy and hanging
Starting point is 00:05:59 with the girls. He talks about how at some point he wondered if he was trans and he talks about how he feels about that now. He does talk about, like I said, people finding out and how he felt about them finding out and how people reacted when they found out. Everyone reacted differently. The girls in his life reacted one way, his guy friends reacted a different way. Eventually, he did meet the one person who wanted to really boss him around and peg him and all that shit. And he's having a good time. And that's a really interesting story. He had always been into some anal action. So he wound up lucking out and finding this person that is like he's got like the best sex life going on. He's in college now. He has like I said, these two relationships and that's
Starting point is 00:06:42 enough for him. He's still figuring things out. He sent me some picks of him over. They'll be over on my Patreon. His story is super interesting, so I'm going to be right back on with Lily. Hey, Lily. Welcome to the Strictly anonymous podcast. How are you today? I'm doing okay. How are you? I'm doing great. Every fucking cross-dresser that I've taped in one week has called in and didn't flake. And that's like a miracle. I think the tides are turning. I'm very happy. Your name is Lily. You're a cross-dresser. And you have like a really interesting story because he's kind of said in your email to me. I don't know much else, right? But the short story is you're like in two relationships, one where you're like a sissy to somebody, but one where you're like a mistress
Starting point is 00:07:21 to another person. So you're kind of like a switch, right? Right. Yeah. I'm like, I've been a sissy with this one person for about six months and I just started being a mistress for, I'd say about three weeks. It's still kind of new. Oh my God. Are you cheating on the sissy relationship? it's an open relationship with the sissy yeah right okay so there's no big deal right that guy might even be married who knows i don't know i'm gonna get the whole story from you lily uh you sound kind of young how old are you now i'm 24 okay yeah you are young now let me ask you this are you do you consider yourself dating any of these people or are you basically single and these are like hookup buddies that you have right now i consider them hookup i wouldn't consider them like serious right so you're a single guy
Starting point is 00:08:13 you're single, but you're cross-dresser, and you have two people that you're with now. We'll work up to how you met them and what goes down with them and all that good stuff. But let's go all the way back to the beginning, you know? When did you realize that you were into cross-dressing? This might sound a little bit weird, but it was actually like a panty commercial on TV. It was something weird, like bridesmaids, like trying on dresses and like, I don't know, like they're like, I guess they sold me, I guess, on the underwear. and I started trying it around eight maybe 10 years old
Starting point is 00:08:47 and I just kept developing and developing over time to where I was just dressing up nonstop and whatever I could Okay so but it starts with panties right Let's go back to that first commercial Like you see a woman in panties and like for some reason it stood out And then did you go to like your mom's panties or your sister's panties Like you said you started wearing them like where'd you get them from at that age?
Starting point is 00:09:08 My mom Okay and now what did it feel like when you put it on that first time. Like, that does sound corny, but where have they been on my life? I mean, they're just more comfortable
Starting point is 00:09:21 than male underwear. Yeah, I've heard that. I mean, I wear panties. You know what I mean? Like, I only wear those, so I don't know, but a lot of guys that aren't panties are like, why don't they make them with,
Starting point is 00:09:32 you know, guys, you know, stuff with the same material? Was it the look and the feel and everything about it? Or was it typically, mostly like a tactile sensation? thing in the beginning? It was more of just the feeling of them in the beginning, but as I started getting older,
Starting point is 00:09:51 like the look of the panties and how they looked on me, like that started to develop over time. Yeah, I get it. Now, you know, the first time you're wearing them and then you're going back, like, did you know, did you feel weird about it? I'm sure you had a sense that you're not supposed to be doing this, right? You're like hiding it from your mother. Did you feel like you were doing something really bad and naughty?
Starting point is 00:10:11 Did you have guilt about it? Like, how do you remember how you felt about sort of trying on women's clothing at that age? Right, and that's what's weird about it. Like, it wasn't like they told me early on, like, doing it was bad or like, it's not like I heard it, but like it was just this innate feeling that it was bad. If that makes sense? Like it's subconscious. Yeah, you just know. Yeah, so I was very secretive.
Starting point is 00:10:35 We had one bathroom growing up, so I would just act like I was taking a really long show. shower and like just try and over clothes while doing it. Oh my God. Well, wait. So you set you start with panties, right? But then what comes next? Like the whole outfit? A whole outfit? Yeah, a whole alpha basically. But only I would only wear specifically like dresses or skirts. Yeah. But was it was panties always involved in the scenario? Yes, always involved. Right. So it really started with the panties but now then you started trying on your mom's dresses and your mom's skirts and stuff. Yeah. And when you're dressing up in those articles of clothing,
Starting point is 00:11:19 are you looking in the mirror and seeing yourself? Or are you looking in the mirror and seeing a woman? Like, what is it about you putting them on? Like, are you even looking at yourself? I like to look in the mirror, yeah. And I just see, it's weird. It depends on, I guess, my mood at the time. Like if I'm like really happy, then I guess I'll see a female. But if I'm feeling
Starting point is 00:11:46 like kind of shitty, then I guess I'll just see a guy in a dress if that makes sense. It kind of depends on my mood. Oh, that's interesting. But what do you prefer to see? Like what makes you the happiest when you're looking at that mirror? Both. Not a guy, really. Just a, just a female. Right. Now, okay, so you're trying on all that stuff. Do you ever get caught? I've I've gotten caught but like not in the act I the close well how many times how many stories of making caught do you want to hear I have a lot of them really well tell me the first one let's start off with the first time you got caught who you got caught by and what happens first time I this was during like COVID I was a sophomore in high school and my
Starting point is 00:12:40 parents were both working and i was doing like remote learning right and i got it all right i was like screw i'm just going to like try my mom's dresses and i'm just going to like make up heels like the full nine yards like i was like fully like decked out and she was supposed to be at work i was like 11 o'clock and then out of nowhere as i'm trying to wedge my feet into her heels i just hear the door open. Oh my God, you're fully dressed. Yeah. Okay. And I like I tried to like take everything off, but like I forgot I saw how to make up on my face. So like I came out. I was like, hey, what's going on? Like acting like nothing was out of the ordinary. Oh my God. And then you see your mom's face looking at you like, what the fuck is going on? Yeah. Yeah.
Starting point is 00:13:34 It was not good. Only what she said. She tried to give me an owl. She was like, anything you want to tell me? And me being the dumb as I am. I'm like, no, no, no. Everything's fine, you know, but like it wasn't. And then she eventually said, I see the fucking makeup on your face. Oh my God.
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Starting point is 00:15:19 All you got to do is go to the description, click on the link, and use my code anonymous. That's code anonymous. Use it now for 60% off plus a 14-day money-back guarantee. Again, go to the description, click on the link, and use my code anonymous. Yeah. And what did she say? Good. Only what she said. She tried to give me an owl. She was like, anything you want to tell me and, you know, me being the dumbass I am.
Starting point is 00:15:47 I'm like, no, no, no, everything's fine, you know, but like, it wasn't. And then she eventually said, Chase, I see the fucking makeup on your face. Oh, my God. Okay. And then when you realize you still had your makeup on, what did you say to her? I just made up an excuse that I was confused and I don't know. I was just like curious. I just made up some very basic mundane answers. You know what I mean? Like I was confused.
Starting point is 00:16:14 I was experimenting, blah, blah, blah. Right. Now she never caught. And she seems to take it easy. Right. But before that, all that time, taking a long time in the shower and wearing all of her clothes, she never caught you before this. So it wasn't until a high school where you're getting caught, right?
Starting point is 00:16:28 Or junior high school. What are you in middle school? No, sophomore high school, right? Yeah. Yeah. Right. So did she question you again or did she sweep it under the rug? She grounded me. She took my phone and made sure I couldn't do anything and then I got caught quite a few times over the years, both in the act and like post, because I would like to tell people that I'm a cross dresser, like just like, I don't know, like I wanted to be one of the girls, you know what I mean? So I would like tell like girlfriends I would do it. Not like people all dating, but you know, like my friends that were girls, they, they.
Starting point is 00:17:08 to do it. And, you know, sometimes they would tell and it would spread. And then she found out that way. Oh, my God. One of the moms probably called her up and was like, do you understand what they're saying about your kid? And what did she say to- Of course.
Starting point is 00:17:27 What did she say to you? She would just be like, why are you like doing this to me really? Like, why are you doing this? like do you, Ada's, are you trans? Are you this way? And like,
Starting point is 00:17:43 she's not very open. She's very conservative. And so I knew I just had to keep playing dumb. And I'm just lucky because I can still play dumb and say I'm confused, even though so many times I've gotten caught, it's hard to be confused for like 14 years, really, when you're doing the same thing. Yeah, exactly.
Starting point is 00:18:07 But, well, listen. I mean, she doesn't like, if she's not so conservative that she like disowns you, right? By all when she finds these things out right? I mean, she's conservative in that she's just not going to like have further conversations about it with you. Right. Because I mean, she doesn't like I mean, did she punish you all these other times? Like what happened all these other times? Yeah. She grunt. She punished us me all these other times whether it was taking my car, digging my phone. Yeah. And it's like the dumbest thing. Because like what is punishing you going to do? It's that doesn't even make sense. You know what I mean? Like I could see you saying, hey, do you want to go see a therapist? Do you want to talk about this?
Starting point is 00:18:47 Like let's, like, you want me help you out with this, right? Because it's a hard thing to sit with as a kid, right? You're all by yourself with this fetish. You don't know, you know, you were very open about it and telling your girlfriends and stuff. But a lot of people keep this shit to themselves. So like, you know, the punishing you isn't going to do anything, obviously. I mean, she could punish you so many times you still, and she still caught you. So at some point she's got to realize like,
Starting point is 00:19:08 punishing doesn't work. Right. And you would think that, especially like with the therapist thing, she thought I was doing this cross-saging shit because I was depressed, but really I'm depressed because I can't further or better explore this way. Right. So she didn't realize you need the therapy to work this all out because you're depressed because, you know, she's punishing you, you're suppressing it. It's more for that. And she was thinking the opposite, like you're depressed because this is what you do? What do you mean? Right? Yeah, basically. Like she's like, you're just doing this because you're depressed. I was like, no, like I'm depressed because I feel this one. Yeah, because this is a part of me and I can't fully live it out because of all of this nonsense,
Starting point is 00:19:56 including you punishing me every time I get caught. Yeah, exactly. Yeah, yeah, it's hard. It's hard. Now, do you have a father in the house or no? I do, yeah. Okay, so now is she telling your dad or is she not telling your dad. Sometimes, like, when, like, the word would get around that I was cross-dressing, then it would happen, like, actually, I remember, like, the first time, like, the word started getting around that I was cross-dressing. He was the one that told me, because he's a teacher at the school. And so, like, he pulled me aside.
Starting point is 00:20:30 It was, like, lunch. I was, like, super happy. I had pizza that day, and he was like, so, what's all? Exactly. Like, it was, like, the best day. never and he was like so what's this i hear about you wearing dresses and telling everyone about it i'm like what yeah but she like that's like the card my mom plays like do you want me to tell your dad or do you promise to stop now like that's the card she likes to play right because she's
Starting point is 00:20:57 just trying anything she can to just make you not have this fat she doesn't understand right like a lot of people don't understand this is not something that's going to really go away you know, but she thinks it can and she tries all these different tactics, you know, but like your father that day at lunch, I mean, did he wind up, he can't really have a full on conversation with you while you're at the school. I mean, does he wind up talking to you about it outside of school that same day or did he ever bring it up again to you? No, he'll try his best just to avoid it at all possible cause. Because I would think a father would have even a harder time with it. I don't know, you know, I mean, but you know, who knows?
Starting point is 00:21:39 Maybe your father's wearing panty hose secretly. You never know. I don't want damage in my head, but maybe. But no, like, the day of that, like, I was, like, in my room playing video games, like, after, like, crying. Yeah. You just came downstairs to start playing video games with me. I think, like, trying to form a connection, I guess. I'm not sure.
Starting point is 00:21:59 But, like, I could tell you was still pissed, but he was playing video games with me. Like, nothing happened. Well, that's kind of, listen, I mean, it could be worse, you know what I mean? Your father could be, like, really put you down and shame you for it and stuff. I think it's actually pretty cool of him. Like, worst case scenario didn't happen. Best case scenario didn't happen either, right? But the fact that he, like, sort of brought it up, but then was able to hang out with you and stuff,
Starting point is 00:22:28 I think that that's pretty good considering, you know? Don't you think? Yeah, like, I know I have. It easier compared to a lot of other cross-trazers and trans people out there. Like, I know that, and I always make sure to tell myself that it could be worse. Let's talk, though, more about your dressing. So let's get to the point where you're, like, in high school telling people. Like, you are literally, because I, listen, I talked to a lot of cross-dressers, right?
Starting point is 00:22:54 I just told you I taped like five people this week. And they're all, another one was in their 20s. And it's very different for cross-dresses in their 20s. And there are, like, cross-dresses in their 50s because those guys grew up in a time. where, you know, nobody was talking about this. So they've just been living double lives, their whole lives. You know, here you are like this little kid who's wearing his stuff. His mom doesn't want to deal with it, but she's old to you, right?
Starting point is 00:23:16 Like, when, at one point do you start having the balls to, like, tell your friends? Well, I would make sure to, like, tell people that I feel like I could trust first before I could do it. Right. And it was, like, really just people I liked and would, like, maybe, want to explore this with, I guess. And it was just really just COVID. Like I was just like bored out my mind and like I was like dressing up every day. And I like, you know, I like see like other like of my friends are girls like communicating stuff like that. I was like, why can't I be one of the girls? You know what I mean? Yeah. Let me ask you a quick question of everybody. I want to go back to
Starting point is 00:24:00 this train of thought. Like, you know, you are a cross-dresser and did you ever. Did you ever, wonder if maybe you're trans and you want to be a woman or do you just like to dress up as a woman and feminize yourself sometimes? That is something that sometimes I still think about but really
Starting point is 00:24:19 for me it is just the clothes like maybe one day I'll change my mind maybe I'm in denial right now but right now it is just the clothes and dressing up because I still have this like dominant side to me that I or just a little bit more masculine side that I still enjoy. I'm not like hyper, hyper femme all the time. You know what I mean?
Starting point is 00:24:40 Yeah, I think there's a very big difference between a cross-dresser and a trans person. Like, you know, a trans person feels like they are a woman like trapped in a male body, you know? And I just think a cross-dresser feels like a man who sometimes likes to dress up like a woman. I think there's a big difference. And you listen, you're only in your early 20s and you know what your early 20s and your whole 20s are, your whole 20s are about figuring out who the fuck you are and what the fuck's going on in your head. So you'll figure it out, you know, and there's really no rush. But as of now, you don't think you're trans. You just think you're a cross-dresser. Right. Right. And especially in COVID, like, that was the confusing part because I was just like, you know, I was stressing up every day. So I did get to me a little bit
Starting point is 00:25:20 more as if I'm trans, maybe, but as I started to take a little bit more breaks, I was like, this is not for me. Right. You don't want this full time, but there's something about it that you enjoy every now and then. Yeah. Right. When did it turn? sexual for you, like, just like when your hormones started raging? Yeah, basically, there's no easy way to say, but being blunt, yeah. Like, I don't know exactly when I started to feel really submissive about it, but it got to the point where, like, just wearing panties and being dressed up, it just turned me on or, like, having one of my friends being like, oh, you look so cute.
Starting point is 00:26:03 cute today, you look so gorgeous. Something about that just really turned me on in a way. Yeah, that's interesting. So it was a part of being submissive, like those panties made you feel and being submissive while you're wearing them. That was like the turn on for you. Yeah.
Starting point is 00:26:19 Now, when you're talking about your friend saying you're so whatever, like, were you dressing up at school? Oh, not really. No, I was like, I mean, this is the best part about like doing this in my 20s like Instagram, Snapchat.
Starting point is 00:26:35 I was able to just like send it to them. You know what I mean? Oh my God. But your guy friends do? No my God. Oh God. No. That was like my worst ever fear.
Starting point is 00:26:45 Is that your girlfriends were fine? You think your girlfriends didn't wind up telling the guy friends? They most certainly did. Girls have the biggest fucking mouths. They most certainly did. Yeah. Yeah. All right.
Starting point is 00:26:55 So let's go back to this thing with you're telling your friends because I'm pretty impressed with that. And it's a different world nowadays, you know? And I think that this isn't as uncommon. as it was, you know, 20 years ago that you would wind up telling a couple people. Maybe not all everyone, but the fact that you told your girlfriend, you know, there was more than one person you could trust and word got out, how did these girls react when you would tell them? Surprisingly pretty nonchalant. All of them were pretty much like, cool. They didn't really
Starting point is 00:27:26 cared by them much, yeah. Yeah, well, what people don't understand, and I came to this conclusion a long time ago, but I didn't realize it all my life. It's like, nobody cares about you that much. Like, everyone thinks about themselves. You know what I mean? Even if, like, they think about you for two minutes, like, like, if they're going to think about you badly, they're going to think about it for two minutes and then they're going to go back thinking about themselves.
Starting point is 00:27:47 Like, that's what we all do. Think about it. Do you sit around and ruminate about anyone else other than yourself? No, we all just fucking think about ourselves all the time. That's all anyone cares about. No one's thinking about you and your cross-dressing for the whole day, you know? So at the end of the day, and especially girls that age, They don't give a fuck.
Starting point is 00:28:02 They're just so concerned with their own shit, you know. No, exactly. And especially, like, I did figure out a little bit earlier. Like, even if they say they care, they care because they think they're being helpful or allies. Like, they're doing it for themselves in a way. Yeah. If that makes any sense. Yeah.
Starting point is 00:28:20 Like, they're not, like, really, like, thinking about me that way, like, 24-7. And that was something I had to really, like, figure out early on because I was like, oh, shit, maybe they, maybe they are. Like, am I, are they going to tell? man like uh but your guy friends did find out correct i mean if your dad found out yeah i was gonna be like if your dad found out everyone found out now how did your guy friends react uh just a lot of bowling really and it got of over time it got a little bit better but occasionally like i don't know i remember like it was like a year after i like got caught with all this right and we're just walking the track one day and like I made like one comment and they said dude you literally wear your mom's bra
Starting point is 00:29:09 shut up like so that was like something they could just throw out anytime yeah and they did when they could yeah hey listen you know guys have had pills since the dawn of time that get them hard right well now women have something too and it's called shamelessly aroused and it's not just some pill that's maybe going to work? No, this is topical Viagra for women and it works. All you got to do is rub it all over your Vag. Wait 15 minutes and it sends the blood rushing exactly where you need and want it. And you know what that means. That means more natural loop, stronger orgasms and more sex because you're going to want to actually do it again and again. So whether you're premenapausal, manapausal, or just tired of always having to work so hard to have an orgasm, you're going to love shamelessly aroused. Now, listen,
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Starting point is 00:30:55 at shameless care.com. Or just go to the description, click on the link and use code strictly to get $10 off plus have better fucking orgasms. We're just walking the track one day and like I made like one comment and they said, dude, you literally wear your mom's bra. Shut up. So that was like something they could just throw out anytime. Yeah.
Starting point is 00:31:18 And they did when they could. Yeah. But let me ask you this. Like what's the difference between guys and girls at that age? Like I wonder like did your guys friends stop being friends with you or did they stay friends with you and sometimes just take. digs or did you like lose your guy friends? You know it's interesting.
Starting point is 00:31:38 Like I was like, because I played sports with a lot of them. So it's not like they could. So it's not like I could never see them as they stops being my friend, right? Yeah. I feel like a lot of them like I was pretty good at just being like, I'm not trans. I'm not any of this. I would not, when they bullied me, I didn't like get involved. So I would say I was like friendly towards.
Starting point is 00:32:01 them but I wasn't being being invited to like hang out with them after school or anything. And you were before they felt? No, but were you being invited to any of those things before? Oh yeah. Oh, okay. So it did change your relationship with your guy friends. Yeah, it did. Yeah. That's tough. I mean, yeah, but it also like, they're really like, where I grew up, the guys here are really toxic and I'm kind of glad that I didn't like have to experience that 24-7 honestly because like hearing the stuff they say and like especially towards like trans like it's like I'm glad I didn't have to be towards that yeah I like that's a great that makes sense I get it so you were like when you were like in the closet so to speak around them you just heard all
Starting point is 00:32:47 their like ignorance coming out so like you were like not a big loss for you right because you couldn't be yourself with those people anyway right like it was like thank God I don't have to like deal with this any more than I have to yeah like I could just like see it from a distance and occasionally they'll throw a jab on me but like like a like a jab at a school in a public setting like I can maybe handle that yeah yeah okay so but the girls did you get closer to some of your girlfriends because of it like did any of them like see you dress up did you start dressing up in front of any of those people or was it still something that you did privately at this point? I'd dress up in front of a lot of them, yeah. I would go through their house
Starting point is 00:33:32 sometimes and they would just dress me up however they want. We would just have a girl's day, sort of speak. And how would they react when they would see you dressed? They were proud of themselves because they were being in charge of doing it. Like I was like, I was just their doll sort of speaking. Like they're like just like happy for me. Like, oh my God, you look so cute, but just what you said earlier, a lot of them don't care that deeply about it. Yeah, not at that age. Yeah. Mm-hmm. Now, when did you start dating and were you, you were dating women? Like, what, how do you, how do you identify sexually? What's, what's your, I, uh, this, you know, it's weird. Like, I, I, I, I like girls, but, you know, like dirty talk, especially, like, I mean now, like being a cissy, like, it turns me on to the thought of like being paked down by a guy or like,
Starting point is 00:34:31 just taking cocking on me. Like, so I'm still figuring that out, but I say primarily I like girls. Right. Now, do you only like men when you're dressed? Yeah. Right. Okay. So who do you lose your virginity to first?
Starting point is 00:34:46 Guy or a girl? Girl. Okay. Sadly, it was a boring missionary. she thought I was cis, you know what I mean? That's everybody's first. No one has a great first experiences, really. Anyway, it's okay.
Starting point is 00:34:59 So you lost your virginity to a woman. When was the first time you were with a guy dressed up? And how did that happen? I haven't had that yet, sadly. I've only been with girls and they've picked, and I've had people that have like paged me before, but I've never been with a guy all dressed up. Oh, okay.
Starting point is 00:35:16 So your sissy relationship and your mistress relationship are with women? Yeah. Interesting. Okay, let's get to when you meet these girls, like the first one, six months ago, you meet a girl, you said, and you are her cissy. Like, tell me about that relationship. Is she somebody, like, from your high school that knew that you were into dressing? Yeah, she was someone that I was friendly with from times of time, but, like, we never really
Starting point is 00:35:44 talked about it before. Yeah. But then, like, after we graduated and she was like, hey, are you still into, like, dressing up and all this stuff. And I was like, yeah, yeah, a little bit. And like, I mean, there wasn't really any chance in hiding there, right? But like, and then she's like, well, I was starting to maybe think about getting into that kind of like fetish territory. What do you maybe want to meet?
Starting point is 00:36:08 I was like, can we just zoom first? Like, because, you know, someone saying you want to meet after a fetish is not a good thing, usually. I guess. I don't know. To me, it's like you hit the jackpot. I was so scared True I was so scared
Starting point is 00:36:24 But Why you know this girl though right I know but like I don't know my Hindsight you're right I was probably being a dumb ass But I should But anyway
Starting point is 00:36:36 We're being overly cautious With meeting strangers And shit or anyone Is never a bad thing right You know you're never going to wind up on date line But I just don't understand it But that's okay So but you wind up meeting her
Starting point is 00:36:49 and she goes in I mean it's interesting that she did lead with that I mean that's what she was interested in with you when it came down to it was the fact that you were a sissy and cross-dresser right? Yeah and that's what she said like
Starting point is 00:37:04 I know that you did this for quite some time and I don't know if you're into this sort of lifestyle but I was but I do have sort of a fetish of being like a dom. Interesting. And I was wondering if like If you are just a crossresser or if you are a sissy, just because you're the only one I know in the town, would you maybe be interested in doing that?
Starting point is 00:37:28 Yeah. Okay. So you meet up with her. What goes down? First, it was pretty simple. Like, she would just dress me up exactly how she wants me, makeup, nails, panties, whole nine yards. And she'll just have me do, like, simple tax, you know, like simple sissy tax, like cleaning, uh, sometimes I'd have to do her homework.
Starting point is 00:37:53 I would braid her hair, like boring stuff. But then it started to elevate in terms of the tax and dares, and she'd be pegging me. She'd have me wear a bug plug for the majority of the day. Chastity, a lot. Okay, but wait, let's stop right there because you mentioned, like, anal play. You know, I'm always, like, on a mission to get every guy to try some kind of anal play. I think a lot of guys out there have gone to that area of their body.
Starting point is 00:38:19 and, you know, figured and tried stuff. Now, before she pegged you, should I assume that you had explored that area of your body before? A thousand percent, yes. Right. Like when you were young, right? I think a lot of people do. I mean, I've had some really funny thing.
Starting point is 00:38:36 Like some guys told me he shoved like a GI Joe up his ass once. He was a military guy later on. It was kind of funny. But so you had gone to that area and you knew that you liked like anal action at that point, right? she's going to peg you. Right. It really, I was, you couldn't hide a smile on my face when she asked me if I wanted to do this kind of like anal play. I was like, yes, yes, yes. Like, I couldn't even hide it. Oh my God. I mean, you really did hit the jackpot. Where are these girls? I guess the younger generation is so interesting to me because like, look at how girls are nowadays. Like, and it's
Starting point is 00:39:12 funny because all these older guys are living double lives are so afraid to bring it up. But like, how do they know that they're not dating like a woman that is dead? And, like, a woman that is dead. And like your girl is because I don't think that like people are being made differently. I just think that people are allowed to express who they really are now as opposed to back then. So that means that there's women walking around that are just like this girl that have that in them that want to express it but never could because they grew up in a different time. I mean here's this young girl who's able to be like yeah, I want to strap it on and fuck you in the ass and boss you around and all this shit. It's crazy. I mean have this just social media playing like if they have this like
Starting point is 00:39:49 urge or fetish, they're able to just look it up and see that it is a little bit more common than they think. It reassures them that, like, yeah, it's nothing wrong with that. I mean, that's what happened with me. Like, I was like, am I the only person that's ever worn female clothing before? Right. Like, that's truly the first, but then I was like, I am definitely not the only person. And that's how I found your show. Like, yeah. I've seen a lot of people being like, yeah, there's this podcast where they talk about it. You're not alone. Yeah, I love that. And that's the biggest difference between these poor guys that are older, where they grew up in a time where there was no internet imagine. We just had to sit around and think all day long. It was like the worst. You know, and there was, so there was nothing except incyclopedias.
Starting point is 00:40:27 And there's nothing in there about cross-dressers, really, you know, like there was no way to get any kind of information. There was no sense of community. So you felt very alone. So yeah, it's a very different time. Okay, so she's like literally like what kind of tasks? So you're always dressed up when you're with her, right? When you're having sex with her? Yes. Like, that's like the main. I can't wear any boy clothes when I'm. with her at all. Does she have her own place? Okay.
Starting point is 00:40:54 She has her own place. And do you let just she make you clean? Like what are the tasks she makes you do? Clean, braid her hair. Sometimes she'll have me do like humiliating tasks. Like wear her panties in a butt plug and like go out and like buy groceries for me. Right. Or how about we go shopping today and I'll like dress you up a little bit and we'll go like three hours out of town and she'll like dress me up.
Starting point is 00:41:19 Wow. I need her on my podcast. She's an interesting. I want to get in her head. Okay, so she makes you do all that. And now, like, this is obviously a sexual thing for her, right? Like, after she sends you out with like the butt plug to go grocery shopping, does she, like, is that foreplay for her? Do you come home and she's like fucking turned on? And do you go out, like, at that time, are you going out dressed or are you going out as a guy, but with a butt plug in? sometimes it's like sometimes we go out and I'm fully dressed up but sometimes she does this thing where we'll go to like Victoria's Secret and we'll like and she'll like out being fully I won't even be wearing like panties then and then like we'll like slowly like pick out stuff as I'm a guy and I'll like slowly start putting more stuff on as I as we're going to store to store. Wow. So like I'm being transformed in the store which is a little crazy. but yeah she's like this is like really turns her on for like as soon as like we get like to her place it's like
Starting point is 00:42:22 it not to be gross but it's almost insane like she's like on the floor now like she's very dominant it turns her on extremely she feels powerful right and she wants to get it on that's what i mean so it is for play for her her the fuck on just like it's turning you on i mean you are the perfect match right because it's turning you on to beat her sissy slave, correct? Correctly. This is truly a jackpot, like anything a sissy would dream of. Yeah.
Starting point is 00:42:53 Let me ask you this, because I wonder, like, you know, if this could ever turn into anything more, because, you know, there's nothing better than having a partner that not only can you have, like, great sex with, but that you could, like, really be yourself, you know. Do you guys, like, have a relationship outside of the sex with each other?
Starting point is 00:43:11 I'd say we've grown, like, we were friends before this a little bit. So we still remain like friends. And we've only grown stronger because of this. But I mean, she, we talked about it. And she's like still once like a quote unquote like real man like a little bit. And this is just kind of like a fun kink for her a little bit. And she doesn't know what she wants because like how is she going to like how is,
Starting point is 00:43:42 where's this part going to go when she's with a quote unquote real man? First of all, you do know that you're a real man too, right? Yeah, but I understand what she means by that. And plus we're both still in like college trying to figure it out. So like, you know what I mean?
Starting point is 00:43:59 Like I get it. Yeah, yeah. Yeah. I think that, you know, I could see it a little bit more clearly. I think like, you know, looking at you guys that you're just very well suited because this is something that
Starting point is 00:44:12 you could kind of do together and everything. When you were in your male form, are you more dominant? Are you like a quote unquote real man when you're like dressed up normally, like an in your male persona? Or are you more like a sissy guy always? I would say like 100% sissy when I'm like in the girl close and I'd say like 40% sissy when I'm like it never goes away, but I'm able to hide it a lot more. and boy clothes.
Starting point is 00:44:43 Right. So maybe she really wants just a much more dominant man. And maybe, because listen, there are some guys that are very dominant regularly and then they get dressed up and they're a little bit sissy then, you know, but you're a little bit not so dominant even when you're not dressed up, right?
Starting point is 00:44:57 And that might be the disconnect between the two of you guys. That has nothing to do with the other stuff, you know? Because listen, the fact that you guys have this in common and you both like it is a great thing for the both of you. Yeah, exactly. And I don't hoard to it.
Starting point is 00:45:11 I mean, We've grown a lot closer as friends. Yeah, that's great. I'm just great to just have that alone. Yeah, of course. I mean, it's amazing that you're getting to live out this fantasy with somebody who's like right there with you. You know, it's not like you're paying her.
Starting point is 00:45:25 It's not transactional. She's not doing it for you. I mean, she's really fucking into it. There's nothing more of a turn on, right, than somebody, like, because there's something, there's one thing when someone goes and it's transactional. Maybe they're paying for someone to, like, live out that cissy fantasy. But, like, this girl is, like, doing it because she's like, horny for it. That's like the top of the mountain. Yeah, and that's what we talk about all the time,
Starting point is 00:45:46 like, how kind of lucky we are that we get to explore this side together. Like, sometimes we kind of have, like, a little, like, reflection, like, session sometimes. Like, after we, like, have sex, we kind of, like, talk about what we really likes, what we didn't like, and just, it kind of how lucky we kind of are to find each other. Yeah, I agree. Now, let's get to the point where you meet the person that you are the mistress for. I mean, like, you know, another girl that's into something else, right? Right. She was a sissy friend that I met online. And this is purely an online relationship right now. Okay. So sissy meaning a man who dresses up as a woman sometimes? Yes. They are trying to transition into a girl, but they are really, really submissive.
Starting point is 00:46:37 Right. Okay. Okay. So this is someone that you met online. And now this person is more sissy than you? Or like, how did two sissy mean? And the one guy, the one sissy says, oh, no, I want you to be my, my, I want you to da me, right? That's who you are, the mistress? Yeah. Like, we were just friends, honestly. Like, I was just trying to meet like other sissies online. Yeah. And we just found each other on a Reddit and started talking. And then we moved to. Instagram, we just started to really hit it off. And I was telling her about this relationship I have with my mistress. And she was like, man, I wish I had that kind of thing. And like, she seemed like really sad about it because like that's all she wants. Like that's truly like all she wanted. And I was like, fuck, why don't I just like give it to her a little bit?
Starting point is 00:47:31 I mean, it's online. And I can just like maybe see if this is what she wants to do. I was like, what's the harm in it? And I asked my mistress and she's like, yeah, sure. I mean, especially since this is just online. Like, I don't see the harm in it. Yeah. So, yeah.
Starting point is 00:47:45 So you started playing. And how do you like being more of the dom in that situation? It's surprisingly really fun because I get to see, this is my similar, but I get to see kind of myself through someone else's eyes in the way that's like, that turns me on in a way. Mm-hmm. And it's just kind of, it's just, it's just exhilarating, honestly. Like, I guess it's just like, she's just really fucking into it.
Starting point is 00:48:16 And it just, I don't know, like, sometimes it is nice to have a little bit power, but still remain feminine, I guess. That's kind of how I look at it. Like, I still get to remain feminine. She calls me mistress, mommy. We do FaceTime and I, like, dress up with her. But, like, I, you know, she still call me mistress. and I'm still dominant. So it's just a nice way to explore my femininity in a way, just through a more dominant lens.
Starting point is 00:48:43 Right. Okay. So that makes sense because you could project onto that sissy because you are one, right? And you've been in that position. So, but you prefer, I would assume, what's going on with the other girl, right? Where you are the sissy being bossed around. Yes, 100%. And we do that a lot more frequently, I'd say, than the,
Starting point is 00:49:06 online sissy i mistress for but i mean it is still just a fun little thing we do it and it's it's still new so we're still figuring out but right now it's going really good does this person live close to you is there any chance that you'd ever meet up with them or no oh no they're like out of the country like oh okay right okay but so are you do you go back and tell those stories to your your mistress that you have something times, but I kind of like, my sister's very shy and I sometimes joke with her that I'm going to tell everyone because that turns her on, but I don't know, I kind of want to respect her privacy just a little bit because she is just so shy. Okay, so she's very shy, so you keep them separate, but everything's
Starting point is 00:49:54 cool and everything. Let me ask you this. Like, do you go out dressed up besides when she's like making you do it and stuff? Do you go out dressed or is it still something that you just do secret? and privately when you're not with her. I will shop for female clothes. I'll maybe sometimes try them on. Like, I'll go like two, maybe three hours out of town to try and shop. But it is something I kind of just like don't feel comfortable doing without anyone with me, I guess. Especially just how everything is right now.
Starting point is 00:50:29 Oh, right, because of the new, because of the new regime. Yeah. So like, it makes me feel more. comfortable just having someone there even you know what I mean yeah of course do you live alone now are you still at home or you live at college yeah I have an apartment with a roommate in college okay now does your roommate know what you do is did word get out in college what you do or because god no okay okay yeah you learned your lesson you don't go tell me learn my lesson nobody knows in your college life
Starting point is 00:51:06 I mean, like, some people know that I'm a little bit, like, some people know I cross this a little bit, but nobody knows about this lifestyle. And, like, here it's a little bit more okay just because it's college, we're all adults, like, and I won't see these people again. Yeah. Like, I, I've told maybe, like, three people. Okay. They don't give a shit.
Starting point is 00:51:26 They don't. No. And they, like, I mean, since we're all adults, we're college and, like, it's not like I'll see them, like, every day anyway. Do you know what I mean? Of course. Yeah, I get it. Yeah, it's better than high school in that word didn't. And plus it's, listen, it's a lot bigger of a community than high school, right, where word's going to spread like wildflower. Like here, it didn't spread to other people, correct? Like, your roommate has no idea. No idea. Oh, my God. Now you're making me think what if you find so.
Starting point is 00:51:56 No, well, don't worry about it. I mean, how long you've been in college for? You're 24, right? Haven't you been there for a couple years and it hasn't spread yet, right? Yeah, this is my final year. Luckily, hasn't spread. Fingers crossed are still time, but Yeah. So how many times, like, do you dress every day, you know, when you're by yourself? How many times a week do you see that girl? Well, my mistress makes me wear panties every day. Oh, you're out. So in class, at any time you're out, you're wearing panties always. Yep. Okay. Okay. Okay. And I tried to dress The ideal is to try Like being a dress every day
Starting point is 00:52:40 But usually doesn't happen But I'd say like Four times Four times out of the week Like four days out of the week I'm like dressing up Right and what's your vibe and style And like you know
Starting point is 00:52:53 Where do you get your stuff from nowadays Um Hmm We usually just do a lot of thrifting Yeah that's a good idea. That's smart. Yeah. So you go to throw shops?
Starting point is 00:53:06 Yeah. It's just hyper pink, feminine, which ideas, which is just crazy to me because when I was like, you know, a teenager that I was like, ew, like pink. Like I was still having that idea on my head. But like now like it's like just hyper pink like short, like short skirts. You know what I mean? Like just like very sweaty.
Starting point is 00:53:28 Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah. Yeah.
Starting point is 00:53:30 And that's the stuff that you're like attracted to. Where do you hide your stash in your room? Under my bed in two bags. Like I have a huge duffel bag and then inside that's a backpack that has my clothes in it. Now do you go all out? Like do you have like skirts, tops? I know you have panties. Do you have bras?
Starting point is 00:53:51 Do you have shoes? Like what do your wardrobe consist of? I have bras with C-silcon cup. And I have some painting hose, stockings. I have two pairs of five heels. Also, I can just go right now and probably look for my whole stack. No, what I want you to do is send me a picture of your stash. That's always interesting to other crossshelters, you know, like the pick of the stash.
Starting point is 00:54:19 Like lay it all out, dump it all up on your bed and take a pick, you know, and they can see all your pink stuff. What size shoe do you? How do you look, like how presentable or passable are you when you dress up, by the way? I'd say at least maybe 60%. Like I saw a room to grow, mainly because, like, the wig I have is not good at all. They're expensive to get a real one, a real good one, right? Yeah, but right now, like, just makeup alone. Like, I'm getting better.
Starting point is 00:54:47 My mistress is really good at it, too, and she helped. She's helped me and taught me a lot. I'd say I'm, maybe if you're just, like, walking past me, like, super fast, you won't recognize me. but like if we're talking like you'd be like oh you're a you're a cross-dresser right now it's you when you go home to see your family now and stuff like that is it like just something that's never discussed anymore because you haven't been living with them and they don't think they probably think that you like let go a bit a long time ago or does it ever come up sometimes like my mom like my mom and family would be like you're staying out of trouble right you're not doing any
Starting point is 00:55:29 that weird shit. Like every once in a while if they think I'm being like extra quiet or secretive. Like that's kind of my tell. Just being actually quiet. But it never really came up in a more like confrontational way. Right. Now what's your future look like for you? Like what would be the ideal partner? Would it be a woman that you could dress up as a cissy for like you have now, but would be dating them? Do you ever want to get married? Do you see yourself having a long term partner? I mean, I would love to just be a Cissy for someone, but I don't know, like, I kind of just want to live on my own
Starting point is 00:56:10 just for like a little bit, you know, just like a little bit taste of life, especially after a fishy college, you know what I mean? Of course, yeah. Listen, I never understood when people got married. In my day, people got married in their 20s. I'm like, I think I was very ahead of my time. I was like, who the fuck would want to get married now? I mean, spend the rest of your life with one person, you know?
Starting point is 00:56:29 Like, it's like, well, you got a long time. to go. There's no rush for you. Right, exactly. And I think, you know, I still want to get, in my language, I still want to get railed by guys. Someone who's experienced so many other things. So I kind of just want to like, I don't know, experience my 20s a little bit and like experiment a little bit more.
Starting point is 00:56:47 I still have a lot more time. Yeah. Okay. So that's something that you want to check off, which is like be dressed up and be with a guy. Because you've been able to do that with a woman and be pegged in the ass and everything. But you want the, you want to try it with a, with a man. Yeah, I want a real cock, yeah. Yeah. Now, why hasn't that happened for you yet? Because you can make that happen, right? You throw a picture of yourself dressed up on Grindr. You're going to have like, you know, a lot of guys hit in you up. It's just the way that it goes. There's a lot of guys. It's interesting. Like, there's just a lot of guys out, quote unquote straight guys that are, you know, are looking for this kind of hookup. Because whenever I have a cross-disse around that says they put the picture of themselves as a sissy up online, they get hit up by a lot of guys. Right, and a lot of it is just fears just, you know, not to get too political, but just the new regime and everything.
Starting point is 00:57:40 And like, even before then, like, you just hear all these horror stories that kind of like threw me off, I guess. Listen, it's scary. As a woman, I know, like, I'm not meeting some strange guy in a car to bang him, you know, because, like, I could be killed. I watch a date line too much. You know, I get it. But, like, you know, you could build up a rapport with somebody and really get to know them. ahead of time. You know, listen, it's like the way you met this person. Do you ever worry about the guy thing, like being too close to home because maybe people will find out or something? Because I'm surprised. Because like I said, if you want that to happen, like you can make that happen, you know, and it doesn't necessarily have to be with some 50 year old guy in a car. You know, you put yourself online. You might find somebody that doesn't give you the creeps, you know, it seems kind of normal and you could talk to them before you meet up with them and make sure it's a safe situation. Right. And I mean, that's something I've like slowly like wanted to develop. Like you used to just be like guys are gross. Like I just like wanted to dress up like a girl, be with a girl. And like they thought of like taking a real cock scared the actual living shit out me. But like, you know, as I slowly started. Yeah. And like that's just changed over time. And so I definitely want it to happen. And I think maybe if I like moved to a city that's maybe a little bit more.
Starting point is 00:59:01 liberal in a way because here like the guys here like they're just it's just not a good pool you know I mean like a like they look like shit and B they're also a more conservative yeah those are always the ones though I'm telling you can just for shits and giggles put up a fake pick of yourself I'm telling you you're gonna have a hundred guys in your area all those conservative freaks are going to be hitting you up trust God that'd be amazing yeah trust me I'm surprised listen you got to take it at your own speed. You know, this is something that's been percolating. I think when you're ready, you will go there and you won't have a hard time meeting anyone, but there is no rush. You are living a great life in that you get to be a cissy with this one girl. I mean, you know,
Starting point is 00:59:45 that's like something I haven't heard of a lot, right, where somebody like you meets a woman who's not only willing to do it, but it's really turned on by it. So you kind of like, you know, why go look for anything else right now, you know? And you do have your other sissy on the side who is a guy, right? So does that fulfill some of those desires? Yeah, like I just usually like if I'm not with my mistress, I still can experience a little bit of that with my sissy. So like, no matter what, like I'm still like getting the daily dosage of this. So it's always being a little bit more fulfilled. Yeah. Yeah. Now, do you ever meet like just girls, right? that like want to date you but you like and would you date somebody that doesn't know and as a guy you know because if you're gonna meet like you know do you ever does that ever happen in your regular life occasionally I'd get hit on and I just politely decline I have no I've in no way want to be a man just like plainly in that kind of relationship, you know what I mean?
Starting point is 01:01:00 Yeah, I get it. Yeah, that's what I was thinking was going to be your answer. So you don't engage. Do your parents ever wonder because you, like, have you not brought any girls home? Oh, yeah. They wonder all the time. And sometimes I'll make up stories of being like, oh, yeah, my girlfriend going to make it today, blah, blah, blah. Sometimes I'll make up bullshit like that.
Starting point is 01:01:20 You do have a girl. Listen, you do have a girl that you're with. And you've been banging her for six months, right? Yeah, like it's not alive, but it's just like not exactly the way they're thinking. Yeah. Yeah. Yeah. They, they, uh, it's so interesting how your, your parents, but you know, listen, who knows what you wind up with in the future. A girl like this who you could have a relationship as well with like down the line would be perfect for you when and if you're ever ready for a real relationship, right? Because you got the sex thing like that, you know, you want to, you know, that isn't, it's not all.
Starting point is 01:01:56 of a relationship, right? That's why you don't have a relationship with this girl, right? It's, but you have this great sexual relationship with her, but if you're a real relationship, you have to have other things going on, you know, but the fact that, you know, but you could find that eventually down the line. And who knows who you'll find that with or who you're going to wind up with now, but you are kind of living the best life. Like a lot of guys are going to be, a lot of cross-disters listening to this are going to be jealous. I'm posting one tomorrow of a young guy cross-dresser. You should listen to that one. And I love that I have yours and I'm going to put yours. out there too because I think it's so interesting to see how this kind of fetish is playing out for
Starting point is 01:02:32 the younger generation. It's a little bit different. I mean, he was more on the DL with his story. Yours is a little bit more out and the connection you have with this girl and what's going on is super interesting. So this will be up soon on a fetish Friday. Do me a favor and can you send me in some like anonymous picks for my crossdresser Patreon tier? Yeah, sure. Okay, do it. You send me some picks. Send me a pick of your stash, whatever you got. Send it to me soon. than later. And when your episode goes up, I'll send you a free access to my Patreon so you could talk to other people there if you want, as well as free access to my Discord. And there's like a whole cross-dressing tier over there too. And you could go into there whenever you want, okay?
Starting point is 01:03:09 Oh, that's amazing. Thank you. Yeah, you're the best. I love your story. It's super interesting. What do we call you? Lily? You send me those pictures ASAP. I'll send you the link to Discord so you could get it and stuff and Patreon. And, but get me the pick sooner than later so I have them, okay? for when I air it. All right. Awesome. Sounds good. Thanks, Lily. Thanks so much for calling in. Yeah. Yeah. Maybe when I found a hookup with a guy, I'll call back. For sure. We'll do the part too. I always need extra content for just my Discord. Not for my Discord, for my Patreon, Crossdes for cheer. So I do exclusive episodes over there that aren't aired anywhere else.
Starting point is 01:03:44 So like a part two or something like that would be great for that. But this one I think I'm going to put out on my podcast because it's so interesting. Okay. So stay tuned. All right. We'll do. I'll send those books immediately. Thank you so much. Thank you. Bye, Lily. Bye. Bye. Okay, I just want to tell you before you go that my book, it's called Strictly Anonymous Confession, Secret Sex Lives of Total Strangers, is now available not only in paperback and e-book, but you can pre-order the audiobook. It's still not going to be out until August 25th, but you can pre-order it. The book is basically 17.5th. different stories taken from my show. I kind of picked one story from each category that I talk about on my show. Like there's a hot wife story. There's a cuck queen story.
Starting point is 01:04:32 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
Starting point is 01:04:48 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 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.
Starting point is 01:05:19 And if you buy my book in any format or pre-order it, I will throw in a compliment. link to my Discord. My Discord does not disappoint. Okay. There's no way you get into 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 can 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
Starting point is 01:06:00 of your purchase, whether you did the audiobook, the ebook, or the paperback. Send it to me at Strictly Anonymous Podcast at gmail.com. That's strictly anonymous podcast at gmail.com. And I will send you the link to Discord. So anyway, thanks so much for tuning in. Okay, good news. I do have a book out. I wrote a book and it's coming out. The book is called Trickle Anonymous Confessions. Secret Sex Lives of Total Strangers. What I did was I picked out the 17 best episodes. That was very hard to do. Okay. I picked like one from each category. And I retold the story from the third person. So it's not interview style. It's a little bit more erotica. The only place where I took creative liberty was in the sex scene. So it's even hotter than my episodes. Like I said,
Starting point is 01:07:04 it's told in the third person. And they're all true, just like my show. I mean, these are real stories from my show, just written out. Like I said, in the third person, not an interview style, more like a story, but a true story, a true super hot story. Now, listen, it is available for pre-order now. And it's not coming out until October 14th. And I was like, oh, my God, that's a long time away. So I figured I'd incentivize people. If you want to pre-order it now, I will give you free access to my Discord if you pre-order it now. All you got to do is screenshot, a pick of the receipt, just screenshot it to me. Send it to Strictly Anonymous Podcast at gmail.com.
Starting point is 01:07:45 And then I will send you the link to my Discord. So that's a little incentive to pick it up now. It's on Amazon, Barnes & Noble, Simon & Schuster. The link is in the description. So make sure to click on it. and if you get it, send me the pick of you purchasing and I'll give you free access to my private Discord that is a totally naughty, super hot community with a lot of people over 2500 people over there having fun. Remember email me the pick at Strictly Anonymous Podcast at gmail.com.

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