Guest Post: Writing A Trans* Woman for "Milk & Cookies & Handcuffs" by Kathleen Tudor

My first ever trans* story was written for a call for submissions for Storm Moon Press, for a trans* anthology that never got produced. (Although my story will be released as a single, if I can ever get around to finishing the epilogue! Argh!) I wrote it because it was a challenge for me, since I knew very little about being trans* and what that means or entails for those who identify in that way. It was something that I wanted to get right, and to treat respectfully and emotionally, so it required a lot of talking to people, reading blogs, and empathizing.

And oh, my, did I learn a lot! I came to feel that I was beginning to truly understand and empathize with trans* people (and trans-women in particular), and only then was I able to write the story about a trans girl who has to come out of the closet to confess her love for the boy she's been friends with for ages.

It was an exciting challenge, but it was certainly a challenge, and I was pretty sure that it was the only trans* story I was ever going to write. After all, it wasn't really in my range of personal experience, and it still didn't quite fall within my comfort zone.

So, imagine my surprise when I saw the call for kinky Christmas stories for Milk & Cookies & Handcuffs, and a trans* story popped into my head, fully fleshed, like the birth of Athena. No! I thought. I don't know what I'm doing! I'll write something else!

But the idea for this story between Jeff and Athena (who I named as a nod to the way my idea was formed), would not leave me alone. How could I walk away without telling the whole world about Athena, the kick-ass woman who lovingly dominates her house boy, Jeff, and Jeff's dawning realization that he is, well, really more of a she, when it comes down to it.

Jeff—who starts to call herself Jessie—and Athena have a lot to deal with. Their relationship has been stable and happy for years, and Athena feels like Jeff/Jessie is throwing a wrench into what has been comfortable and familiar for a long time. For one thing, if Jeff/Jessie is a woman inside, where does that leave the heterosexual Athena?

Jessie was a really fascinating character for me to explore. She is a woman who has hidden, even from herself, the truth of her nature for a very long time. This is rather near and dear to me, since I didn't realize I was a lesbian until over halfway through my twenties.

But Jessie isn't just coming to terms with being a lesbian.

For as long as she can remember, Jessie has been a masochist who cherished pain, particularly to her cock and balls, a region she felt deserving of pain and punishment. Though she thought of them as disgusting and unworthy, it took years and a flash of insight before she realized why she had such a love/hate relationship with the body-parts she loved to torture: they were foreign to her inner image of her woman's body.

Let me tell you, it took a lot of work to feel like I was getting Jessie right. I didn't want to imply that every CBT lover is trans*. I didn't want to imply that Jessie was just self-hating. (She's not!) I didn't want to imply that she was deranged or disturbed. And, when Jessie told me that she didn't want to go through with sex reassignment surgery, I didn't want to portray her as any less female or any less trans*.

Jessie is a woman, a masochist, and a slave. She loves her cock because her Mistress loves it, because it hurts so good, and because it tickles at emotional masochism. She hates it because it doesn't really, truly belong to her. And having it doesn't make her any less a woman than wearing a strap-on and pegging your boyfriend does.

Jessie's story felt both inspiring and terrifying to me. It was a tight-rope walk over some very deep waters, and I hope very much that I have managed to make the crossing and to do honor to the trans* community with my words.

And, of course, I hope you read her story one-handed.

Kathleen Tudor (aka D.K. Jernigan) is a writer, and editor who sometimes walks on the wild side. Her work has appeared in Best Bondage 2012 from Cleis Press, Hot Under the Collar from Xcite Press, and many other anthologies. She is also co-editor of the Circlet Press anthology, Like Hearts Enchanted, with more forthcoming in 2013. Her novella, Hearts of the Hunted is available now through Storm Moon Press, along with "Gift of Self" in the Milk & Cookies & Handcuffs anthology. She can be found via e-mail at PolyKathleen@gmail.com or by visiting her website, KathleenTudor.com.