Maddie's Firsts - Unveiling the Journey: Firsts in Dressing and Self-Discovery
- Maddie Taylor

- Dec 15, 2025
- 16 min read
In the latest episode of "My Girl Life" podcast, Maddie Taylor takes us on a heartfelt journey through the memorable "firsts" in her dressing experience. These moments, etched in her memory, have shaped her path and resonate with many who share similar journeys.

The Mirror Moment
Maddie begins by recounting the transformative experience of seeing herself fully dressed in the mirror for the first time. This moment, she describes, is mind-blowing and exciting, overshadowing any imperfections. It's a switch that once turned on, never goes off. This initial glimpse is not just about appearance but about unlocking parts of oneself that were either hidden or unknown.
The Feel of the Fabric
Another significant first for Maddie was the sensation of wearing clothes that felt right. From a young age, the feel of the fabric was special, but it wasn't until later that she could process these feelings. The act of dressing became more than just wearing clothes; it was about aligning her inner self with her outer appearance.
Shaving and Smoothness
Maddie shares the exhilarating experience of shaving her body for the first time. The smoothness of her skin was a revelation, marking a new chapter in her journey. This act, once a novelty, became a routine, yet it remains a cherished memory of self-discovery.
Making Connections
The journey of self-discovery is often solitary, but Maddie highlights the importance of making connections. Her first friend, Rachel, invited her to a girls' night out, transforming her experience from solitary dressing to a shared journey. This connection made her feel part of a community, adding depth to her experience.
Public Appearances
Maddie recounts the nerve-wracking yet thrilling experience of spending an entire evening as a woman in public. From dining to dancing, these experiences were not just about being seen but about living authentically. Each outing built her confidence, making her feel more at home in her identity.
The Power of Social Media
Facebook was a game-changer for Maddie, opening up a world of connections and friendships. It provided a platform to share her journey, find support, and feel less isolated. Social media became a window to the world, allowing her to connect with others who understood her journey.
Karaoke and Confidence
Singing karaoke as Maddie was another memorable first. Despite initial nerves, she found that most people were supportive and accepting. This experience taught her that the fears she had were often unfounded, and it encouraged her to embrace her identity more fully.
Conclusion
Maddie's journey is a testament to the power of firsts in shaping our identities. Each experience, from the mirror moment to public appearances, has contributed to her self-discovery and confidence. Her story encourages us to embrace our own journeys, take calculated risks, and find joy in the process of becoming who we truly are.
Subscribe Now
Join Maddie on her journey by subscribing to "My Girl Life" podcast. Discover more stories of transformation and empowerment, and be inspired to embrace your own path with courage and authenticity.
Transcript:
Madde Taylor:
Welcome everyone to another episode of My Girl Life podcast. Please show me some love and subscribe to the channel and like the episode if you liked it. It tells me I'm doing something worthwhile and allows me to keep doing it so thank you in advance. Today I'm gonna talk about firsts. No, not those firsts, dressing firsts. I don't know about you guys but I'm guessing we all have firsts with regards to our dressing that have burned into our minds and our memories forever. And I'm gonna share some of mine and maybe some of you can relate. I know coming out firsts are huge and very impactful and very memorable, but I've already covered those in other episodes, so I'm not gonna be covering those. So the first one I'm gonna talk about, which I think out of all the experiences, there are a few that shape every cross dresser's journey.
Maddie Taylor:
And the one that stands out the most for me and I think for a lot of people is that first moment you see yourself in the mirror. You look in the mirror and see yourself fully dressed and it's hard to describe. It's kind of mind blowing, it's exciting, it's transformative. And you're not necessarily worried about the quality or the perfection of your presentation. It's just transformative enough to overshadow any of the imperfections. And I know I'm sure it's different for everybody, but I think there's a lot of overlaps. I personally think when this happens, there's a switch that goes on and I don't think that switch ever goes off. And I think you guys know what I'm talking about. Once you dress, see yourself, experience that moment, it's very addictive, it's very exciting.
Maddie Taylor:
It opens up things inside of you that either you knew you had and you couldn't let out or you didn't know you had and all of a sudden it's coming out. It's pretty amazing. As many of you probably like me, the full length mirror became my best friend, right? How many times have we posed? Well, how many times have we got out and got a full length mirror for our room, for our house? And lots of pictures and lots of looks in the mirror. I also at that kind of that same time remember being in a skirt and heels and how my legs looked and that was just I think I've talked about this in the past. I think when I first originally started dressing there was a sexual component to it. There was a turn on to it. I'm not sure how that works but I do know there's part of the mind that doesn't necessarily know what's real and what's not real and what it takes in, what you see. There's part of your brain thinks it's real and I think that's the part it touches. And it's just pretty amazing. Then came the desire to keep improving the look, the presentation and striving to become passable. I personally don't think I'll ever be 100% passable. I don't.
Maddie Taylor:
expect to and I don't really try to, my goal is to become 100 percent presentable. And I think it's important to make that distinction because I think you can drive yourself crazy trying to be passable and there's very few people that can truly, pass. And I'm talking about close proximity and interaction with people and they still don't know. I think from a distance if I walk in or somebody doesn't really hear me talk or whatever. I think I'm fairly passable in some situations. But if they have a conversation with me or if they see me at any length of time, I think at some point they realize that I'm a guy. But I just want to be presentable and that's my goal.
Maddie Taylor:
So my first makeover, which would have been the first time I saw myself in the mirror, was a makeover with Chris from Studio Lights, back when Studio Lights was in Denver. This was a while back. And Chris did the makeover, and if you've ever had one, usually they won't do it in front of the mirror, you're facing away from the mirror, and then you have that big reveal where they turn you around. And again, that moment is very memorable, burns into your brain. He did kind of do my eyebrows a little drag-ish. He pulled them up with tape under the wig, which I later, you know, I didn't really want to do that. But other than that, it was really good and it was amazing. So I hadn't thought about where I was going to go afterwards. So Chris suggested an LGBTQ bar.
Maddie Taylor:
down the street so I went there and just kind of sat by myself. I didn't really talk to anybody. I do remember I had a lot of vodka and Red Bulls and when I got home I was so sick. I can't even smell Red Bull now and definitely would not drink a Red Bull vodka. But that was a fun night. It was a great experience for getting out and having that moment in the mirror is probably the number one memorable first that I have.
Maddie Taylor:
Lastly, the big moment for me was putting on the clothes and the feel of them. And we've all talked about that, how amazing that is. Even when we were young, young, young kids, we didn't really know what we were doing. When you put the clothes on, it felt a certain way, but you didn't process it. But as we get older, obviously you process it, but seeing it on in the mirror is amazing. So that's number one.
Maddie Taylor:
Number two, these aren't in any, these, and these are not in any particular order. The next one is shaving my body. The first time of feeling smooth, a smooth body. And I wasn't that hairy to begin with, but even a little hair makes a big difference when you rub your skin and especially the legs and the chest, when they were smooth.
Maddie Taylor:
That was exhilarating. That was amazing. I remember back when I used to say, I get to shave and now I say I have to shave. That kind of that newness wears off and I've also talked about how that happens. So yeah, shaving the body and having smooth skin was very memorable and a great first. Next would be making a friend.
Maddie Taylor:
So my first friend, her name is Rachel, and I went to an LGBT club here in Denver called Tracks. And again, kind of like the other time I went out, I just kind of sat by myself. There was dancing, it's a discotheque, different dance floors and bars, et cetera, lots of people, and all walks of life. The night I went, it's called First Friday, and it's kind of a melting pot. There's no particular theme.
Maddie Taylor:
It's just, you know, first Friday. So you get to see all the energy and all these people that I think probably had to hide a lot of themselves during the week. And it's Friday night and they get to go out and they get to be themselves and be around people who are like them and have the same energy and you can feel it and you can see it. So at that time, that first time I went, I met Rachel and we started talking.
Madie Taylor:
and got to know each other a little bit. And she invited me to this girls night out dinner that they were doing every week. And she invited me out to a girls night out that they do every week where they go to a restaurant. And then once a month they would go from the restaurant to this bar, this discotheque and spend the rest of the evening there dancing and having cocktails and visiting. making that first friend was pretty amazing. And it, for the first time, it became more real. I had somewhere to be.
Maddie Taylor:
I had people that I knew, I had some obligations. If I said I was gonna be there, I kinda felt like I needed to be there. And then you start making plans with people and this whole thing starts to become real. It's not just you putting on some clothes, looking in the mirror and then putting them away. It starts to take on what a real woman would be doing and more importantly would feel like. So that was pretty cool.
Maddie Taylor:
this also includes driving for the first time because, know, I had to drive to these places and driving dressed was, was fun and exhilarating and a little nerve wracking. I don't know about you guys, but I was scared to death to get pulled over, by a policeman and, and having to show my ID and explain. And I think back then you kind of feel like you're doing something wrong. Like it's almost illegal.
Made Taylor:
I say that in jest, but you think you'll get in trouble by being stopped. Now I don't think that. fact, a funny story, my niece's husband is a sheriff here in town. And I always worried that one day or one night that he would pull me over, because nobody in the family knew this was before I came out to anybody. And he pulled me over and I'd have to show him my license and he'd figure out who I was.
Maddie Taylor:
Never happened, but it was always in my mind. Now. I kind of look look back at it and just kind of laugh It's kind of funny now, but at the time it was not necessarily funny Another first was just spending an entire evening as a woman in public and There's just something about Not going to a place and and kind of sneaking and and then sitting in the corner or not talking to anybody
Maddie Taylor:
You're just kind of a fly on the wall, which is interesting and fun in the beginning. But being able to spend a whole evening where you meet somebody for dinner and then you go out to a nightclub or go to a different bar and you just kind of spend the evening as a woman doing all those things, ordering your food and drinks as a woman, paying your bill as a woman. That kind of caused me to get for Maddie to get her own credit card.
MaddiTaylor:
going into the ladies bathroom in a public place was all part of that. So just spending an evening in public as a woman was a great first and I still appreciate that today. Another first were these events, Wild Side and TGR and they kind of coincide with the spending the whole evening as a woman because that truly felt like
Maddie Taylor:
You get ready in the hotel room. You go downstairs fully dressed and you're basically bouncing around town fully dressed as a woman for the entire evening. Then you come home and you get undressed just just like she would. It's just kind of a great fun experience. Specifically, when I used to go to Vegas or really if I went to a hotel, I would get ready with my makeup.
Maddie aylor:
and my clothes, but I'd leave my wig off and I would put the wig in my backpack and in a change of clothes. And then I would go downstairs in with boy clothes over my girl clothes. And I put a hat on as low as I could to kind of hide my face and pray that there was nobody on the elevator. Right. I would even ask for rooms on lower floors. So I would have to spend less time in the elevator.
Maddie Taylor:
in case somebody else was there. That was real. Now I just take it for granted. But Wildside, for me, and it would be TGR or Wildside, but Wildside for me was my first event and I wasn't going to go to my car and get ready. We were meeting at the bar, at the hotel bar. And so I just got ready and I got to the front door of the hotel room, held my breath and just said,
Maddie Taylor:
did it for the first time. And I was nervous, it was exciting, and absolutely nothing happened. And I never turned back from there. So I've said this before, WildSide and TGR and some of these other events can be life changing, game changers for people. It gives you a sense of confidence because you're in a group. And then I think, you you take that confidence back home with you. And just to a certain degree,
Maddie Taylor:
And then it changes. So consider, strongly consider going to these events and experiencing that because it really can be a life-changing thing for your dressing and for your girl journey. There's lots of firsts as part of that. Dancing was one of them. I'd never danced as Maddie. And that was fun and it your feet. And you're like, you got to kind of get used to that.
Maddie Taylor:
You know, just little things like that you wouldn't think of, but dancing as a woman was pretty cool. It is a little self-conscious because you're used to dancing like a guy, but I think I pulled it off pretty good. Next one would be like going to a public event, like a concert or taking public transportation, Uber, Lyft, those types of things where you are that person, you're the girl.
MaddiTaylor:
to that person, the Uber driver, the Lyft driver. In public transportation, you can't go hide in the corner, you're front and center. And it's fun to do something that you've done so many times in boy mode and then experience the same thing in girl mode. Kind of hard to explain. Most of you probably understand. I don't think somebody who doesn't dress probably wouldn't understand that. But just doing things that you did as a guy, doing them as your female persona.
Maddie Taylor:
is pretty cool and very memorable. Next would be Facebook. Facebook was, talk about Game Changer. When I got on Facebook, my whole world opened up and making so many friends online. And yeah, they're online friends. They're not true, true friend friends that know you. But what it led to is when I did go to events,
Maddie Taylor:
I felt like I knew these people because of our communication on Facebook. And so was a natural segue to pick up a conversation or go up and say hi to them, or as maybe you wouldn't meet that person. But if you've been chatting with them or liking their posts and you feel like you almost know them, it really gives you a jumpstart at these events. And then just the interaction, not feeling alone, feeling connected.
Maddie Taylor:
very similar to like when my mom was in a nursing home, we got her an iPad and that was her connection to the world. I mean, that was everything other than I guess the TV, but you know that she texted with the family. She got to see her grandkids pictures and keep up with what the family was doing. Otherwise she wouldn't know what what's going on. So it was really a window and a connection to to the rest of the world. And I think you know as a cross dresser.
Maddie Taylor:
We're in a similar situation where we're probably isolated. We're probably hiding part of it or all of it. And Facebook or social media allows you to connect with people and open up your world, your female persona world. And I think that's very important. I was nervous at first. think everybody thinks, you know, when anybody sees them in girl mode, they're going to exact.
Maddie Taylor:
automatically know exactly who they are. And in some cases that can happen, but I don't think it's realistic in most cases and I've never had any problems. Now everybody I know in my family all knows about Maddie, but you know, back then it was a little unnerving, but if you do it, just be careful with the privacy and make sure you know that friends you connect with are the only ones that can see your stuff and maybe just be careful of what you post. But anyway,
Maddie Taylor:
And then I had to come up with a permanent name. Before I had just kind of made up a name and used it here and there, but it wasn't like a real name. And I didn't have a last name. So I had to come up with a first name and a last name, which was Maddie Taylor. And that was because of Facebook. And again, it just opened up my world exponentially.
Maddie Taylor:
Okay, so one more that would be doing karaoke. So singing has Maddie in front of people was very memorable. Again, nerve wracking, very nerve wracking because of my voice. And I'm a little self conscious of my voice. I don't try to sound, you know, I don't try to talk with a higher pitch. I just want to talk natural. I don't think I have too low of a voice.
Maddie Taylor:
I've been fighting a cold. sounds kind of low today, but I still think I sound like a guy and then singing as a guy, I was self-conscious. But again, nobody cared. Nobody cares. Most people don't care about the things that we're so worried about. So try not to worry yourself about every little thing because people are just not thinking that much. don't really care. And if they enjoy you and enjoy your company,
Maddie Taylor:
And then I think it's all gonna start to, they're gonna start to forget that you're dressed in the moment. They're just gonna be talking and communicating and sharing with you. But getting up there and singing as Maddie was a thrill and very memorable. And I continue to do it to this day. And a lot of these things, I'm glad I got over that moment of fear, got over the hump. Because if I didn't,
Maddie Taylor:
Maybe I wouldn't know what I'm missing, but I'd be missing a lot. so I think pushing yourself a little bit and, you know, do it, do it carefully and do it purposefully. Do it, do it carefully, do it intentionally, but take some of those risks. Take some of those calculated risks. Just to kind of summarize everything. The sense.
Maddie Taylor:
that something inside of me had finally matched what I saw on the outside. And again, I'm referring to really the makeover in the mirror. The sense that something inside now is matching what I saw on the outside is pretty amazing. And I don't think you necessarily consciously think through that, but I think it's definitely going through your mind. It's definitely locked in there as a memory. And I think it comes out as a feeling.
Maddie Taylor:
And I think it comes out as an energy and that feminine energy. So when you do see yourself in the mirror, when you put the clothes on, when you do things as a female that you did as a male and you have friends and you're spending an evening or even more as a woman, I think that energy just gets released and it's transformative. And that's when I think the dressing becomes a long-term thing.
Maddie Taylor:
because for most of it, it doesn't go away. And I know a lot of us have purged. I've purged several times and, you know, hopefully you can get over the hump of the last purge. And if nothing else, if you need to stop for a while, put the stuff in storage or hide it somewhere. Don't throw it all away. I know it feels hard if you're feeling guilty or shameful, throwing it away is part of that process of getting rid of it. But if you can hold on to it,
Maddie Taylor:
I'm pretty sure you're gonna come back to it and you tell me.
Maddie Taylor:
Also, when I step into Maddie, it's not necessarily the dress or the heels that change me, it's that internal shift. Body language softens, kind of a feminine rhythm kicks in. I smile more probably, I've been told. When I let myself feel more, I definitely do that. And I'm pretty outgoing as a guy, but I'm even more outgoing as Maddie. And I'm actually a little more candid and...
Maddie Taylor:
honest and it's led to some really good quality conversations and good quality friendships. Just being candid and not agreeing with everything and kind of developing who you are as a girl, as Maddie, and having my boundaries, which some of them are different than gyms. But cultivating all that.
Maddie Taylor:
You know, it really becomes real. think that's the best thing I can describe is the whole thing starts to become real when you start experiencing these firsts. Take it in, write them down so you can remember them. A lot of them you probably don't have to because you'd never forget them. I think all these first steps, whatever you want to call them, it's a revealing process.
Maddie Taylor:
of revealing the feminine side of us in a more holistic way than just putting on the clothes. So, you know, just wearing clothes feels more like a costume now. But these things I'm describing that I did in it are first, those I would define as revealing. They revealed Maddie in me. anyway, with that being said, that's all I have for today. Thanks for watching and listening.
Maddie Taylor:
Appreciate your support and I hope these episodes help support you in your journey and be careful out there and remember be bold, be kind, be you.





Comments