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How important is it to see examples of soft masculinity? To see men cry and express themselves. To see masculine folks find joy and love. Well, I always say visibility equals possibility because once we see it, it becomes an example of what is possible for yourself. That is a huge part of this conversation with Cai Shirley, black trans poet and educator. In this episode of Dem Bois Podcast, Cai shares his journey of self-discovery, exploring themes of genealogy, family dynamics, and the complexities of transitioning.
We talk:
3:04 - Exploring genealogy and family history
17:59 - Conversations about transition
36:54 - Embracing change and identity
42:04 - Redefining masculinity through family influence
58:08 - Visibility equals possibility
1:05:21 - Excavating Black Trans histories
Episode References:
Caillou
The Will to Change by bell hooks
The L Word
Degrassi
Stone Butch Blues by Leslie Feinberg
Star Trek
Nichelle Nichols
Read more about Cai in his bio below:
Cai Sherley is a Black trans poet-educator with roots in Boston, MA. A two-time Pushcart Prize nominee, his work can be found in Best New Poets, swamp pink, Peach Mag, and Tupelo, among others, as well as the anthology I Feel Nothing Like Good: Poets Against Genocide. He has found homes at The Watering Hole, Brooklyn Poets, Tin House, Lambda, and the Chicago Poetry Center, and is a member of Trans Corner Poets. His work centers Black trans life, past and present, in the United States, and his debut chapbook, Out of Yearning, was released in October 2026.
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2026 marks ten years of Dem Bois Inc. To honor this milestone, we invite you to join our 10 for 10 campaign by giving $10 a month to help sustain the care, leadership, and visibility that trans men of color deserve.
Your support helps build a future rooted in care, visibility, and possibility.
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