About

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.

• The Revelation (00:00:00) Anna describes the night Harry revealed his crossdressing to her, her initial shock, and immediate emotional response.
• Introducing the Podcast & Anna (00:00:17) Jenny welcomes Anna, introduces the episode, and sets the stage for discussing partners of crossdressers.
• Life Before the Revelation (00:01:10) Anna shares her and Harry’s life before the revelation, their background, and her openness to diversity.
• Kink or Identity? (00:03:19) Discussion about whether Harry’s crossdressing is a kink, an identity, or somewhere in between.
• The Night of the Revelation (00:04:20) Anna recounts the details and emotions of the night Harry came out to her.
• Initial Reactions and Aftermath (00:06:24) Anna describes her questions, confusion, and the difficult weeks and months following the revelation.
• Societal Roles and Shock (00:08:08) Jenny discusses societal expectations, the shock of revelations, and the journey of couples facing hidden truths.
• Harry’s Transformation and Boundaries (00:10:12) Anna talks about Harry’s excitement, spending spree, and the process of setting boundaries as they adjusted.
• Harry’s Unchanged Core (00:12:41) Reflection on how Harry remained the same person, just with a new dimension, and Anna’s feelings about it.
• Jenny’s Personal Journey (00:14:39) Jenny shares her own experience with crossdressing, coming out to partners, and how honesty shaped her relationship.
• Intimacy and Bedroom Dynamics (00:18:36) Anna discusses how crossdressing was introduced into their intimate life and her evolving feelings about labels and attraction.
• Labels and Acceptance (00:21:16) Jenny and Anna reflect on the usefulness of labels, societal expectations, and embracing partners as they are.
• Going Out as Harriet (00:23:11) Anna explains whether Harriet goes out in public, their decisions regarding family and children, and societal influences.
• Deceit vs. Survival (00:26:19) Exploring the difference between feeling deceived and understanding the survival instinct behind keeping crossdressing secret.
• Societal Shame and the Spectrum (00:27:39) Jenny discusses shame, societal reactions, and the broad spectrum of gender expression.
• Strength in Sharing (00:30:50) Jenny and Anna talk about the courage it takes to reveal crossdressing and the strength of their relationship.
• Advice for Partners and Crossdressers (00:33:44) Anna offers advice to both crossdressers and their partners on navigating revelations and emotional responses.
• Crossdressing as a Benign Kink (00:35:07) Jenny compares crossdressing to other kinks, emphasizing its harmlessness and playfulness.
• Coming Out to Friends and Family (00:35:50) Anna discusses who knows about Harry’s crossdressing, reactions from friends, and concerns about family and community.
• Societal Reactions and Personal Drama (00:37:28) Jenny reflects on how most people react briefly and move on, and the importance of context in coming out.
• Aging, Testosterone, and Embracing Femininity (00:40:06) Jenny discusses how aging and hormonal changes can influence the desire to express femininity.
• Survey Insights: Unhappy Relationships (00:42:23) Jenny shares survey results about crossdressers feeling trapped and the risks of coming out.
• Advice for Women Discovering a Partner’s Secret (00:44:13) Anna gives advice to women whose partners have just come out as crossdressers, emphasizing research and open-mindedness.
• Creating Supportive Resources (00:48:08) Anna explains why she and Harry started their website, aiming to provide honest, supportive information for the community.
• Mother-Daughter Fantasies and Social Media (00:49:00) Jenny describes a viral post about mother-daughter dressing up, and the overwhelmingly positive response online.
• Advice: Don’t Throw Away Relationships Lightly (00:52:41) Jenny shares relationship advice: consider carefully before ending a relationship over crossdressing.
• Rediscovering Intimacy (00:53:43) Anna describes how introducing crossdressing rekindled excitement and intimacy in her marriage.
• Relationship Cycles and Recommitment (00:54:58) Jenny discusses the natural cycles in long-term relationships and the importance of recommitment.
• Reading Jenny’s Books (00:56:06) Anna reviews Jenny’s books, describing them as spicy and refreshing, and discusses the genre of trans erotica.
• Writing and Experiencing Trans Erotica (00:57:09) Jenny explains her approach to writing erotica, focusing on tease, sensuality, and the veneer of femininity.
• Audiobooks and Immersive Experience (01:00:04) Anna shares her experience with Jenny’s audiobooks and how they enhance the stories’ immersive quality.
• The Art of Tease in Storytelling (01:02:12) Jenny discusses the importance of tease and anticipation in her writing and the essence of crossdressing.
• Character-Driven Stories (01:04:21) Jenny talks about her character-driven approach to storytelling and the real-life inspirations behind her books.
• Launching Crossdresser UK (01:05:23) Anna introduces their website, its resources, community growth, and upcoming premium features.
• Final Advice for Coming Out (01:08:32) Anna gives practical advice for crossdressers planning to tell their partners, emphasizing timing, honesty, and self-care.
• Closing Remarks (01:09:47) Jenny thanks Anna, wraps up the episode, and invites listeners to join her website and mailing list.
• Are you happy with the results?

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