Crossdressing, Identity, and Personal Freedom: My Intimate Conversation with LadyC

This episode was such a joy to record. Sitting down with my dear friend LadyC, who has an endless curiosity about human sexuality, felt like two friends sharing secrets over coffee. We laughed, we reminisced, and we explored a subject that has shaped so much of my life: crossdressing.

I came into this conversation with the results of a survey I conducted with over 1,000 people, most of them Baby Boomers, GenXers, and older Millennials. The responses were fascinating and revealed how different generations view gender and sexuality. Early on I found myself saying something that has been sitting in my heart for a long time: “Crossdressing is such a harmless sexual kink, or as we’re going to discuss, it may well be partly identity as well.” That idea, that what we wear can be more than just clothing and can reflect who we truly are, set the tone for everything that followed.

It was not just about numbers and theories. LadyC and I both shared personal stories and I opened up about my own journey in a way that felt both scary and freeing. I even went back to childhood memories, those innocent and confusing moments when you first start to wonder about sexuality. I laughed as I recalled, “I knew that sperm made babies, but I didn’t quite know how it came out of me.” It is funny now, but those early questions planted the seeds of a lifelong curiosity about identity and desire.

The deeper we went, the more we talked about the energy of crossdressing. There is something so electric and yes, erotic, about it. For me, slipping into a different set of clothes is not just a physical act. It feels like stepping into another dimension of myself. LadyC and I explored how that “erotic energy” is not only about sex. It is about transformation, empowerment, and the thrill of becoming another version of me. At one point I said, “It is not just about wearing clothes, it is about inhabiting a different version of yourself,” and I still feel that truth vibrating inside me.

We also unpacked society’s shifting attitudes. It struck both of us how, in many ways, it is now more socially acceptable to transition fully to another gender than to embrace a crossdressing alter ego. That observation shows how complicated and sometimes contradictory our culture’s understanding of gender expression really is.

Perhaps my favorite part of the conversation was when we talked about liberation. There is such joy in this kind of self-expression. I found myself confessing, “When I slip into the feminine, I don’t have any fear of what my body looks like.” Clothing can be transformative in that way. It can dissolve shame and invite freedom.

By the end, LadyC and I were practically buzzing with excitement. We are already planning to attend future events in costume and to keep exploring this world together. At one point I exclaimed, “We have unleashed the wild woman,” and we both burst into laughter.

That is the heart of this episode for me: the wild woman, the hidden self, the part of us that wants to be seen, celebrated, and free. Crossdressing is not just about looking pretty in a dress. It is about stepping boldly into every part of who I am and inviting others to do the same.

From Shock to Acceptance: A Partner's Journey with Crossdressing

When I sat down with Anna for this episode, I knew we were about to share a story that so many people need to hear. As a crossdresser myself - and an erotic author who writes about the delicate dance of gender expression - I’ve had countless conversations about identity, desire, and relationships. But Anna’s journey with her husband Harry truly moved me.

Anna told me about a Friday night that completely flipped her world upside down. Eight years into their marriage, Harry dropped what felt like a bombshell: he wanted to share his desire to cross-dress. In that moment, Anna’s mind raced. She admitted her first thought was that something far worse was coming, an affair, a terminal illness. But instead, Harry’s revelation opened the door to an unexpected journey of love, acceptance, and growth that changed their relationship forever.

What I love about Anna’s story is her honesty. She shared how, after the initial shock, she had to quiet all those “what will people think?” voices in her head and focus on her own feelings. “If I ignore society, if I ignore what other people might think about this, how do I feel about it?” she asked herself. Hearing her say that gave me chills. That kind of raw self-reflection is exactly what creates space for true connection.

And here’s the beautiful twist: their intimate life actually blossomed. Anna lit up when she described how, when Harry becomes Harriet, it feels like they’re back at the very start of their relationship, those early butterflies and nervous excitement returning after years of marriage. How many couples can say they’ve rediscovered that spark in such an unexpected way?

But Anna and Harry didn’t stop at their own relationship. They recognized how few resources there were for couples navigating cross-dressing together, so they created CrossDressed.uk, a safe, welcoming space for crossdressers and their partners to find real support and information. No judgment. Just honesty, understanding, and care.

Of course, our conversation also wandered into my world—my erotic writing. I explained how I approach cross-dressing in my stories, not with graphic explicitness, but by capturing the subtle moments: the glances, the anticipation, the emotional charge when two people truly see each other. For me, those quiet, tender details are far more erotic than anything overt.

Before we wrapped, Anna shared some heartfelt advice for anyone thinking of coming out to their partner. Timing is everything. Honesty is crucial. And most of all, you have to listen, really listen, to your partner’s reaction without defensiveness. Sharing your truth is only half the journey; creating a safe space for them to process it is just as important.

This conversation reminded me why I started this podcast in the first place. Love isn’t about fitting into society’s boxes. It’s about creating a space where both partners can be their truest selves. Anna and Harry’s story proves that with patience, understanding, and open communication, relationships can not only survive unexpected revelations, they can thrive because of them.

My Enlightening Chat with Trish from Be A Lady

I recently had the absolute pleasure of sitting down with Trish, the amazing woman behind Be A Lady, and let me tell you - it was one eye-opening conversation! As someone who's personally explored cross-dressing, I was thrilled to chat with someone who's dedicated her life to supporting people like me on their journey of self-discovery.

Right from the start, Trish's energy was infectious. We kicked things off with some fun rapid-fire questions about clothing preferences, and her motto "live once, try twice and don't die wondering" really set the tone for our entire chat. I love how she approaches everything with such openness and enthusiasm - it's exactly what this community needs.

What really struck me was hearing about how Trish started Be A Lady. She shared this fascinating story about her early days working in adult shops and her first encounter with cross-dressing clients. You could really hear the passion in her voice when she explained how she went from being somewhat naive about the whole thing to creating this amazing safe space for people to explore their identity.

One of the most powerful parts of our conversation was when we dove into the challenges many cross-dressers face. Trish revealed that most of her clients are secret cross-dressers who haven't come out to their partners, which really hit home for me. We talked about how society's attitudes are slowly changing, but there's still so much fear and stigma to overcome. It's why spaces like Be A Lady are so incredibly important.

The way Trish described the transformation process at her service was absolutely beautiful. It's not just about putting on makeup and a dress - it's about that moment when someone looks in the mirror and sees their true self for the first time. She told me about clients having these incredible moments of realization, saying things like "Oh my God, that's me. The real true me that needs to shine every now and again." Those stories gave me goosebumps.

We also got into some really interesting discussions about the emotional and erotic aspects of cross-dressing, which I know can be a sensitive topic for some. But Trish approached it with such professionalism and understanding, explaining how it's all part of exploring one's identity and feeling sexually empowered. It was refreshing to have such an honest, judgment-free conversation about these aspects that often get swept under the rug.

Throughout our chat, we kept coming back to this idea of self-discovery and personal liberation. Trish's approach really resonated with me - she believes in creating a space where people can safely explore who they are, try new things, and never have to live with the regret of wondering "what if?" Her service isn't just about transformation; it's about empowerment and acceptance, something that I think we could all use a little more of in our lives.

In this powerful and deeply intimate episode of Gurl Talk, Jenny Raven delves into her personal journey of self-exploration and discovery with therapeutic kink practitioner Emily Letts. Emily, based in Boulder, Colorado, shares her expertise in using kink and BDSM as tools for transformation and healing. The conversation delves into the complexities of unlocking suppressed desires, navigating societal expectations, and embracing one's true self.

We cover a wide range of topics, including the intersection of divine masculine and divine feminine energies within us, the importance of exploring one's squishy emotions, and the power of breath in processing pain and pleasure. Emily offers valuable insights on how individuals can approach their journey of self-discovery with curiosity, authenticity, and a commitment to embracing all parts of themselves.

Don't miss this raw and authentic conversation that shines a light on the transformative power of embracing one's true desires and embarking on a journey of self-discovery.

In this heartwarming and eye-opening conversation between Jenny Raven and Katie Gardener, two Gen X cross-dressers share their intimate journey of self-discovery and gender expression. The chat feels like eavesdropping on two old friends catching up over coffee, with Katie's candid admission that she'd ideally be Katie full-time setting the tone for an honest and revealing discussion.

The conversation takes us back to the not-so-distant past of the 70s and 80s, where being different wasn't exactly celebrated. Katie opens up about her earliest memories of being drawn to women's clothing, particularly the fabrics and styles that seemed exclusively feminine. It's fascinating to hear how these early experiences shaped her identity, even though society wasn't ready to understand or accept such expressions of gender fluidity.

What really hits home is the generational perspective they bring to the table. Both Jenny and Katie point out how today's world is so different from their younger days. They note how trans identities are now more accepted "on the high street," while also acknowledging that cross-dressing occupies its own unique space in the spectrum of gender expression. It's like watching society evolve through their personal lens.

The discussion gets particularly interesting when they dive into the physical and emotional aspects of their journey. There's this fascinating bit about how aging and changing testosterone levels might influence gender expression - it's the kind of real talk that you rarely hear in mainstream conversations about gender identity. Katie's observation that "the more something is sort of dark and driven underground, the more it wants to come out" really captures the struggle many face with hidden identities.

When it comes to relationships, both hosts don't hold back about the challenges of revealing their true selves to partners. The quote about Katie being "undiscovered" and becoming a bigger bombshell the longer she stays hidden really drives home the emotional weight of keeping such a significant part of oneself under wraps. It's a reminder of how personal relationships can be both challenging and transformative for those exploring their gender identity.

The conversation wraps up with some seriously heartfelt advice for younger folks who might be wrestling with similar feelings. Their message is beautifully simple: enjoy who you are, and don't feel pressured to come out if you're not ready. It's refreshing to hear such accepting and nurturing guidance from people who've walked this path before. The whole discussion feels like a warm hug for anyone who might be questioning or exploring their own gender expression.

This honest and open dialogue serves as a powerful reminder that everyone's journey with gender identity is unique and valid. Whether someone identifies as a cross-dresser, transgender, or is still figuring things out, there's something incredibly valuable in hearing stories from those who've navigated these waters before. It's like they're saying, "Hey, wherever you are on your journey, it's okay - you're not alone in this."

Jenny Raven's latest podcast episode with TransMichaela is like eavesdropping on the most honest conversation you've ever heard about gender identity and self-discovery. From the get-go, these two don't hold back - they dive straight into the deep end with a quick-fire round that sets the tone for what's coming. When Michaela casually drops that she enjoys "cuckoldry in both roles," you know this isn't going to be your typical sanitized chat about gender.

The childhood stories they share hit different - like Michaela's memory of being drawn to the Yellow Power Ranger and playing Barbies with her friend Amanda. It's those little moments that often tell the biggest stories, right? And Jenny opens up about her own journey too, sharing those early feelings of wanting to be female but feeling stuck behind society's expectations. It's raw, it's real, and it's incredibly relatable for anyone who's ever felt like they're living in the wrong skin.

The conversation gets even juicier when they start talking about personal transformation. There's this amazing moment when they discuss the pure joy of finally presenting as your true self. Michaela's got this fantastic quote about Victoria's Secret lingerie that just captures the essence of feeling comfortable in your own skin. It's not just about the clothes - it's about finally feeling like you're living your truth.

The real gut-punch comes when Michaela shares her advice to her younger self: "Stop pretending you are trans. Get on with the transition. Come out. Do not spend any more of your time pretending to be something that you are not." Like, damn. How many of us have wasted time pretending to be something we're not, whether it's about gender or anything else?

They tackle the professional side of things too, which is super interesting. Michaela's got this whole life in finance, plus she's doing modeling and building an online presence. She's really clear about keeping her professional life separate from her online persona, which is something a lot of people could learn from. The way she handles her dual identities is pretty impressive - keeping it real while protecting what needs to be protected.

The conversation wraps up with this powerful message about living authentically. When they drop that line "Wear what the fuck you want," it's like a battle cry for anyone who's ever felt constrained by society's expectations. The whole episode feels like a permission slip to be yourself, whoever that might be.

What makes this podcast so special is how it manages to be both deeply personal and universally relatable. Whether you're trans, questioning your gender identity, or just trying to figure out how to live more authentically, there's something here for everyone. It's like sitting in on a conversation with two friends who aren't afraid to get real about the messy, beautiful journey of finding and accepting yourself.

The episode shines a light on the complexities of gender identity and self-expression, but does it in this super approachable way. It's not some academic lecture - it's just two people sharing their experiences, their struggles, and their victories. And somehow, through all the heavy stuff, they manage to keep it light and even funny at times, which makes the whole thing feel like a chat with your most honest friends.

Let's dive into a fascinating conversation between podcast host Jenny Raven and Miss Naughty, an Australian filmmaker who's been shaking up the adult industry for over two decades. Miss Naughty isn't your typical adult content creator - she's a self-described feminist pornographer who prefers to stay behind the camera, bringing a fresh perspective to an industry that's traditionally been dominated by the male gaze.

It's pretty cool how Miss Naughty got her start. She began writing for a women's magazine in Australia, which led her to discover a whole community of women making their own kind of porn - the female-friendly kind. This opened her eyes to new possibilities in adult filmmaking, and she decided to jump in and give it a shot herself. Talk about a career change!

What makes Miss Naughty's work stand out is her focus on authenticity and real connections between performers. She's not interested in that over-the-top, performative stuff you see in mainstream porn. Instead, she lets her performers be themselves and explore their sexuality naturally. There's this great moment she talks about where a performer had an emotional response during filming, and instead of yelling "cut," they decided to keep rolling and capture that raw, genuine moment.

The technical side of things wasn't always smooth sailing, though. Miss Naughty shares this hilarious story about her first time directing, where she was so nervous she ended up taking over camera duties herself. But that's what makes her journey so relatable - she learned as she went along, improving her skills and developing her unique style over time.

One of the most interesting parts of the conversation is when she digs into what makes feminist porn different from mainstream stuff. It's not just about who's behind the camera; it's about the whole approach. Miss Naughty focuses on storytelling, consent, and making sure everyone's comfortable on set. She's moved away from that classic "pouting at the camera" style, preferring to capture something that looks more like how people actually have sex in real life.

The interview wraps up with some great insights about how the industry is changing, especially with platforms like OnlyFans giving performers more control over their content. Miss Naughty's pretty excited about this shift, saying it's fantastic that performers now have the power to create what they want and get paid properly for it. But she also believes there's still room for the kind of thoughtful, professionally produced content she's been making for the past 24 years.

Looking back at her career, Miss Naughty has some regrets - like not having the chance to work with trans actresses - but overall, she's been a pioneering force in creating adult content that puts female pleasure and authentic experiences front and center. Her work shows that porn doesn't have to follow the old-school rules - it can be ethical, feminist, and still totally hot.

You know how some conversations just stick with you? This chat with Jennifer Lunden is definitely one of those.

Jennifer, a transgender woman who creates erotic content online, really opened up about her journey, and let me tell you, it's fascinating stuff.

What really struck me was how Jennifer's path to becoming her authentic self was totally transformed by the internet. Remember those early days of online shopping? For Jennifer, it was a game-changer. She could finally explore her feminine side through fashion and self-expression without the awkwardness of in-person shopping. It's pretty amazing how something as simple as being able to buy clothes online can make such a huge difference in someone's journey.

The way Jennifer describes her entry into erotic content creation is super interesting - there weren't any nerves or second thoughts. As she puts it, "There was no nerves, no apprehension... because I'd already been on a journey for so long of living my sex life and my fantasies out in public almost." That's some serious self-confidence right there! She jumped right in, focusing on creating intimate, sensual content that really connects with her audience.

Here's something that really surprised me - and Jennifer too, apparently. She went into this thinking people would want all sorts of kinky, hardcore stuff. But you know what her audience really loves? Simple, intimate moments. Kissing, gentle touches, real connection. It kind of makes you think about how mainstream porn might be missing the mark on what people actually want to see, right?

Our whole conversation about the business side of things was super enlightening too. Jennifer's pretty upfront about the fact that this isn't making her millions - she still keeps her day job. But she's clearly found something really fulfilling in this work. She treats it like a proper business, putting in the effort to create quality content and build genuine connections with her audience. The way she describes her favorite outfit (corset, suspenders, and heels) just shows how much thought and care goes into every aspect of her work.

What I found really powerful was Jennifer's advice for others who might want to follow a similar path. She emphasizes being true to yourself and not feeling ashamed about embracing your sexuality. As she puts it, "If you feel that your sensual side, your sexual side is feminine and you feel satisfied and fulfilled, then just don't be afraid to embrace it because there's plenty of us." That's pretty solid life advice, whether you're creating content or not.

And you know what's really cool? Throughout the whole conversation, there's this underlying message about authenticity and self-acceptance. Jennifer's not just creating content - she's living her truth and helping others feel more comfortable with their own desires and identities. In a world that can sometimes be pretty judgmental about sexuality and gender expression, that's pretty dang revolutionary if you ask me.

The whole discussion really challenges our preconceptions about erotic content creation, showing it as something that can be both professionally managed and deeply personal. It's not just about the spicy stuff - it's about connection, expression, and being true to yourself. Now that's something worth talking about!