the 2023 Boundless RETREAT: CLASSES WITH Sinclair Sexsmith

JD of Two Knotty Boys


Sinclair Sexsmith (they/them) is a queer trans butch, a leather dominant, and a writer, focusing on individual, interpersonal, and institutional systems of power. They study dominance and submission, social & restorative justice, the energetic body, trauma, and transformation. They have been in the kink community since 1999, and orchestrate transformative kink scenes through written erotica and ritual practice. They actively explore the philosophies of power exchange and the practicalities of sustainable, long term D/s.

As a leather community member, titleholder, and organizer, Sinclair has presented and performed 200+ times at 75+ venues, including International Ms. Leather, Dark Odyssey, SXSW, Harvard, and Oz Kink Fest.

Their short story collection, Sweet & Rough: Queer Kink Erotica, was a 2016 finalist for a Lambda Literary Award, and they have edited 7 queer erotica anthologies; their latest book is Daddy4Daddy: Queer Kink Erotica.

Find more at &

SINCLAIR at The Boundless Retreat


Flirting Dirty (with Flirting Bingo!)

Many of us come to kink retreats for enlightenment — just kidding, I meant: to flirt, fuck, and play. But making it happen in real life can be a lot harder than we want it to be.

Do you wish more people would hit on you? How do you make yourself more available?

We can all use some practice asking for what we want, but how do you escalate from flirting to foreplay and foreplay to fucking? Learn to perfect the art of the tease, use negotiations as foreplay, and make sex even hotter in the process. We’ll play “flirting bingo,” have a chance to practice different flirting styles, and who knows?

You might even find somebody of interest.

    Writing Spicy: Erotica Writing WorkshOp

    I bet you already write erotica — you text dirty things to lovers or play partners, right? That’s basically it.

    In this writing workshop, we’ll talk about questions like, How do I write the actual sex tho? and, What if I want to get published? We’ll do some writing prompts together, and folks will be invited to share their work and offer positive feedback. You will leave with words written down on a page, and (hopefully) more permission to put your dirty thoughts to paper.

    Participants in this workshop will have priority in the Spicy Showcase on Sunday.

    What to Bring:

    • A notebook and a pen, or something equivalent. 

    Spicy Showcase: Erotic Reading

    Come witness brave folks as they read their dirty words out loud in front of others — which is an act of resistance, an act of revolution.

    There will be content warnings (because we’re going to get nasty) and big feelings and queer lust and politics and who knows what else. Participants in the Writing Spicy erotica writing workshop will have first crack at the mic; find Sinclair and get your name on the list if you want to read.

    Sinclair will MC, and share some of their own erotic poems and stories, too.

      One-on-One Coaching with Sinclair

      Sinclair will be available for 1:1 sessions throughout the Retreat weekend for D/s theory & support, gender puzzles, using energy in kink, and facilitating kink ritual.

      If you’re interested in 1:1 coaching, please contact them directly,, for more information.