Meeting Another Trans Woman in Men’s Prison Made Me Believe in My Future Again

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'Being socially and emotionally connected with another trans woman like myself allowed me to see the possibilities in my own femininity and existence,' says Vanessa del Rio, as told to nadjaguyot.

Lying in my cell at Sing Sing Correctional Facility after lights out, relaxing my body and mind to prepare for sleep, I dream about freedom. I dream of stretching out my limbs and taking a few huge gulps of air, gently running my hand against a tree and feeling the nourishing bark. I dream of being able to dress as I am, in women’s attire, quality makeup, nice wigs, miniskirts, and stilettos. I dream of having all things femme. I dream of being a woman.

But in a way, Penny’s presence also revealed to me how profoundly precarious it truly is for women like us in a place like Sing Sing—a truth too painful to think about while alone. Being in this prison setting prevents me from having all things femme: I can’t wear real makeup, wigs, or gender-affirming personal attire beyond a prison-issued sports bra, which I mostly wear when I’m alone in my cell. I’m never able to truly relax and feel at ease.

I think back to when I was a kid at the Darien Lake theme park, riding on all the big, scary, thrilling rides, like the Viper roller coaster, which navigates loops and sharp bends and curves, and the Pirate, a large boat-shaped ride that swings really high, back and forth, like a huge pendulum over water, and, at the apex of the swing, staring vertically down into the water, gave me the brilliant but terrifying sensation that there was nothing I couldn’t do.

Still, thinking about how fundamentally unnatural prisons are, I ponder when, how, where, and if I’ll reacclimate into society with the stigma of being an ex-con convicted of homicide always stuck on my back, and after being subjected to more than three decades of racist trauma and violence in a prison system energized by white supremacy. This reality, and my decades-long exposure to it, has damaged me in ways that I don’t yet fully understand myself.

 

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