Eight years into marriage, Anna Woods's husband Harry told her something that changed everything: he was a crossdresser.
Anna had never really known what crossdressing was. She grew up in the UK in the 90s, where the only crossdressers she'd ever seen on television were the butt of the joke. She had questions — did this mean he was trans? Did he not want her as a woman? Did he actually prefer men?
What followed was one of the most honest, brave, and generous conversations I've had on this podcast. Anna talks about the fear of "the ick" before seeing Harry dressed for the first time. The insecurity that crept in — "am I not feminine enough anymore?" The moment she realized so many of her feelings weren't actually hers, but what society had told her to feel. And the devastating truth that "you've been carrying this alone — we could have done it together."
Today Anna and Harry run Cross Dressed UK, a resource and community they built so no other partner would have to go through what Anna did without support.
This episode is essential listening for:
▸ Any crossdresser terrified of telling their partner
▸ Any wife who's just discovered her husband crossdresses
▸ Any couple stuck in "don't ask, don't tell" and quietly rotting
▸ Anyone who wants to understand what real curiosity, patience, and honesty look like in a marriage
🇬🇧 Find Anna and Harry:
▸ Website: https://www.crossdressed.co.uk
▸ Instagram, Facebook, YouTube, Pinterest: @crossdresseduk
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🌸 Outrageously Her — Launches July 28, 2026
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If this episode moved something in you, Outrageously Her is where we go deeper. A 4-month intimate cohort for men who are ready to stop managing a secret and start building a life that includes ALL of you.
What's included:
✓ 4 months of live group work — bi-weekly 2-hour calls
✓ Small group sister pods — journey with 2 accountability partners
✓ Community platform for real intimate connection between calls
✓ 1-1 deep dive coaching call with Emily
✓ Guest expert sessions
Apply now: https://www.soulkink.com/outrageously-her
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Chapters:
0:00 – Meet Anna: wife of a crossdresser, half of Cross Dressed UK
1:30 – The bombshell — Harry came out 8 years into marriage
3:00 – Struggling to find real information (and the internet rabbit hole)
5:00 – Growing up in the UK: crossdressers as the butt of the joke
8:00 – The grief every man secretly carries
10:30 – "Am I not feminine enough anymore?"
14:30 – "It's not how you feel — it's how you've been told to feel"
17:00 – How Anna's relationship with her own body changed
21:00 – Chronic illness, losing her career, and Cross Dressed UK as healing
28:30 – The "ick": Anna's biggest fear before Harry dressed
33:00 – What actually happened the first time she saw him
37:00 – Why "don't ask, don't tell" rots marriages
44:00 – Generosity as the foundation of this work
50:00 – The story of Cross Dressed UK
54:00 – The 70-year-old crossdressers who still haven't told their wives
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Topics in this episode:
• Wife of a crossdresser — the partner's perspective
• Coming out as a crossdresser to your wife
• How to tell your partner you crossdress
• Don't ask, don't tell relationships and why they don't work
• The "ick" and how to move through it
• Cross Dressed UK — resources for crossdressers and their partners
• Chronic illness, identity, and finding purpose
• Crossdressing and heterosexual marriage
• Outrageously Her — 4-month cohort for men exploring their feminine
#crossdresser #crossdressing #crossdressedUK
