The Cheeky Sissy Podcast 🎙️

No episodes yet

Check back soon — the first episode is on its way! 💕

The Cheeky Sissy Podcast is an honest, warm-hearted audio series exploring the everyday realities of crossdressing, feminization, and feminine self-expression. Each episode is a relaxed, conversational dive into topics that don't get talked about often enough — body image as a short curvy guy in feminine clothes, the quiet courage of being yourself behind closed doors, navigating relationships, and the small wins that build a confident feminine identity over time.

I created this podcast because reading articles only goes so far. Hearing another voice — someone who's been through the same moments of doubt, joy, embarrassment, and pride — makes you feel less alone in a way text can't quite match. Whether you're listening on a commute, while getting ready, or curled up at home, my hope is that each episode feels like a friend talking you through something they've already figured out.

What You'll Hear

Episodes cover a wide range of topics: starting out as a crossdresser, building a wardrobe that flatters a male frame, talking to partners about feminization, dealing with internalized shame, finding the right wig and makeup for your face shape, dating apps for feminine men, and reflective stories about real-life experiences out in the world. Some episodes are solo musings; others feature guests sharing their own paths.

How to Listen

All episodes stream directly here, no app required — just press play. New episodes drop on a regular cadence, and you can revisit older ones anytime. If a particular episode resonates with you, share it with a friend who might need to hear it, or start a thread about it in the community forum. The conversations don't have to end when the audio does.

Thank you for being part of this growing audience. Audio is a uniquely intimate medium, and I'm grateful you've chosen to spend a little of your time with me. 💕