Episodes

  • Ep010: Sophia Anderson, Delightfully Delicious Lady From Down Under
    Dec 4 2025

    Get ready for a fabulously flirty episode! Jenny Raven cozies up with the dazzling Sofia Anderson, a cross-dresser from Australia, for a playful, intimate chat about all things feminine. From favorite lingerie and sky-high heels to the delicious dance between masculine and feminine energies, these two share their journeys, fantasies, and the cheeky thrill of embracing their true selves. With giggles, confessions, and a dash of daring, Jenny and Sofia explore self-acceptance, sensuality, and the joy of living authentically—heels, lipstick, and all. It’s girl talk with a twist, and you’re invited!


    • Introduction & Setting the Scene (00:00:04) Jenny introduces Sofia, their connection, and the purpose of the conversation.
    • Quickfire Questions: Preferences & Playfulness (00:01:38) Rapid-fire questions about fashion, style, and playful preferences.
    • Sophia’s Favorite Outfit & Style (00:03:33) Sophia describes her ideal outfit and her attraction to classic, mature femininity.
    • Attraction to Classic Femininity (00:04:28) Discussion on why Sophia prefers a timeless, sophisticated look over girlish styles.
    • Ideal Social & Intimate Company (00:06:07) Sophia shares her favorite company and social experiences as Sophia.
    • Perfect Evening & Social Dynamics (00:06:53) Sophia details her ideal night out, the mix of personalities, and the importance of female energy.
    • Masculine Sexual Energy vs. Feminine Erotic Energy (00:09:53) Jenny introduces the concept of masculine vs. feminine sexual energy and their personal experiences.
    • Sophia’s Experience of Feminine Energy (00:12:06) Sophia reflects on her enjoyment of foreplay, seduction, and mutual pleasure as Sophia.
    • Integrating Feminine and Masculine Personas (00:15:39) Discussion about embodying feminine personas in real life and the differences in behavior and energy.
    • Public Expression & Social Reactions (00:18:05) Jenny and Sophia discuss the challenges and implications of being publicly out as cross-dressers.
    • Visibility, Acceptance, and Social Media (00:20:24) Jenny shares experiences with public reactions, social media, and the spectrum of acceptance.
    • Creativity, Intelligence, and Tolerance (00:23:01) Exploring whether creative industries are more accepting and the role of intelligence and tribalism.
    • Honesty, Relationships, and Family (00:26:38) Jenny discusses coming out to her partner, concerns about her son, and generational differences in acceptance.
    • Transformation & Public Presentation (00:29:48) Sophia and Jenny talk about changes in mannerisms, public outings, and the risk of being recognized.
    • Identity, Labels, and Integration (00:32:02) Reflections on being oneself beyond gender labels and integrating all aspects of identity.
    • Personal Histories & Early Experiences (00:33:48) Jenny and Sophia share their childhood experiences, early desires, and the evolution of their feminine personas.
    • Sexuality, Gender Roles, and Relationships (00:36:40) Discussion on sexual preferences, gender roles, and the impact on relationships.
    • Private vs. Public Expression of Femininity (00:39:50) Sophia questions whether keeping Sophia private allows for more rebellion and playfulness.
    • Sexual Energy, Taboo, and Media (00:41:45) Exploring how sexual energy was expressed in youth, the impact of cultural taboos, and media influences.
    • Eroticism, Porn, and the Power of Writing (00:48:24) Frustration with mainstream porn, the appeal of erotic writing, and the importance of mental stimulation.
    • Aging, Testosterone, and Freedom (00:53:45) How aging, changing hormones, and life circumstances allow for more freedom and expression.
    • Living Authentically & Regret (00:57:00) Encouragement to embrace femininity early, but also acceptance if it happens later in life.
    • Therapy, Support, and Small Steps (00:59:16) Advice on seeking therapy, finding support, and taking incremental steps toward self-acceptance.
    • Recognizing Allies & Coming Out (01:00:21) How to identify supportive women and the ease of coming out to receptive people.
    • Conclusion & Next Episode Tease (01:01:06) Wrapping up, excitement for the next conversation, and Jenny’s closing remarks.
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    1 hr and 3 mins
  • Ep 003: TransMichaela, Fashion & makeup model and so much more!
    Jul 20 2025
    Jenny and Michaela's Raw, Real Talk About Gender, Identity, and Living Your TruthJenny 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.Introduction & Welcome (00:00:04) Jenny introduces Mikayla, sets expectations for a candid conversation about identity and experience.Quickfire Questions: Preferences & Sexuality (00:00:40) Rapid-fire questions about color, clothing, sexual roles, and preferences, revealing Mikayla’s tastes and experiences.Sexual Fantasies & Challenges (00:05:09) Mikayla discusses threesomes, fantasies like gangbangs, and the challenges of finding compatible partners.Role Play & Bedroom Dynamics (00:07:35) Mikayla shares her love for role play, favorite bedroom outfits, and memorable role play experiences.Childhood & Early Gender Identity (00:10:50) Jenny and Mikayla reflect on childhood experiences, early awareness of gender identity, and the impact of societal norms.Adolescence, Coming Out, and Transition (00:14:21) Mikayla recounts teenage years, early adulthood, and the journey toward embracing her trans identity.Struggles, Guilt, and Hiding (00:16:37) Mikayla discusses the emotional toll of hiding her true self and the guilt from living inauthentically.Jenny’s Experience: Shame & Suppression (00:17:35) Jenny shares her own struggles with shame, family rejection, and the spiritual impact of self-expression.Cross-Dressing, Identity, and Therapy (00:20:18) Jenny explores her own journey, questioning whether she is trans or a cross-dresser, and the role of therapy.Advice on Coming Out & Living Authentically (00:21:26) Mikayla offers advice on coming out, relationships, and the importance of living one’s true life.Transition Logistics & Support (00:24:15) Practical advice on ...
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    45 mins