“A Pineapple Is Not a Broken Orange” — A Sexual Journey in Three Acts

The hilariously awkward — and poignantly personal — tale of sexual awakening of a late-blooming trans woman

Cassie Brighter
Fearless She Wrote

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Author’s photo

Prologue: The Seductress

I was seventeen years old. I was at a party, and there was this girl. She had gorgeous hair, wide hips, a big round ass, large perky, bouncy boobs. She was an effortless flirt. A sensuous seductress, sure of her sex and her sexuality. She knew she had it going on. The way the boys looked at her!

Oh, this story is NOT about her. But all eyes were on her. They saw her.

And I was invisible. I was in hiding, even from myself. It felt… helpless.

I left that party really wound up. How come she gets to do that?

And I knew the answer. The answer was obvious. I grew up very aware that there are only two sexes: Some got the GOOD one, and the unlucky ones got the other one. She had the good one. The boobs. The hips. And a vagina. I got stuck with the other one. Flat chest. No ass. This… awkward thing, with unpredictable, unscheduled erections and white icky stuff coming out of it.

You think YOUR puberty felt awkward? I remember how surprised I was, in talking to boys…

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Cassie Brighter
Fearless She Wrote

Activist. Public speaker. Writer. Community Organizer. Mom. Creator & Host, Empowered Trans Woman Summit. Managing Editor, EmpoweredTransWoman.com