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Touching Gender for Healing and Pleasure by Caffyn Jesse

Challenging Gender Assumptions

One of the many wonderful things my clients and students have taught me is that I need to continually examine and contest my assumptions. Nowhere is this process more important and fruitful than the realm of gender.

Gender is typically the first thing we identify about someone who calls us on the phone or walks into our practice. Is this a man or a woman? We mark someone as either male or female, and as we do so, we call into play a whole host of assumptions about their chromosomes, hormones, gonads, socialization, self-identity, social identity and partner choice. How are we gendered as only either male or female in the complex interaction of biochemistry, individuality and society? All the elements that constitute our gender are much more diverse than the bifurcation of gender into male and female would allow. Yet this bifurcation is an all-pervading structural element in how we think, act, and move in the world. Assumptions we make about gender can shape and misshape our relationship with clients and the choices we offer them.

As givers of erotic massage, we create an environment in which clients can explore their sexuality. We invite them to cultivate the erotic capacities of body, mind, spirit and emotions. On this journey to erotic freedom, some will break open the prison of gender and the ways it constrains erotic imagination, embodiment and society. I believe that as erotic massage practitioners we have both reason and responsibility to work and play in ways that help expand possibilities in the realm of gender identity, partner choice, and the social, psychological and physical consequence of being designated either man or woman. As we educate ourselves, and make our practices more open, perhaps we can imagine gender outside its social designations and compulsions. Perhaps gender can become a sex toy people can try on, play with or discard.

Tantric and Taoist traditions of sacred sexuality—at least in the forms they reach us today—don’t play much with gender. They can get stuck in advocating the worshipful communion of an opposite-sex couple, yoni and lingam. No doubt such communion can be beautiful. But suggesting that this is the highest form of erotic interaction is harmful, ugly prejudice. The tradition of Somatic Sex Education in which I am trained is one that celebrates the diversity around and within us. We honor same-sex erotic exchanges, solo sex and group rituals.

This is work that challenges gender oppressions as it invites women to experience the full extent of their orgasmic energy, and men to experience their softness, flexibility and inwardness, and gender-variant people to explore and express all the joy we are capable of. We support queer, transgender and gender-variant people on their gender journeys. Can we touch the people that come for erotic massage in ways that support gender diversity and invite transformational consciousness, while honoring each person exactly where they are? Take time to consider your preconceptions and how they are affecting you in your encounter with each person who comes to see you. Then push your assumptions aside, and make space to understand this person as an individual. If they are to encounter you, and not your assumptions, you will need to do this ongoing work. By keeping your mind and heart open, and free of expectations and conventions, you can offer people the space they need to define and redefine who they are sexually.

With your touch and imagination you can bring mindful attention and creative play to the fact that so-called male and female genitals are not so different after all. We all have inner bits and outer bits and beds of erectile tissue. In early fetal development our genitals are undifferentiated. We can explore how to touch in ways that invite a swim in this undifferentiated consciousness.


Gender Identity, Gender Expression,Biological Sex and Who We are Attracted To

Sam Killerman has created a treasure trove of online resources about gender and sexual orientation. He points out that Gender Identity, Gender Expression, Biological Sex and Who We are Attracted To are different aspects of how gender is felt, constructed and expressed in every body. Rather than seeing an opposition between Male and Female in the various aspects of how we constitute our gender, we can notice different continuums that allow for the “infinite plot and label combinations” that actually exist.

A person can be non-gendered in their gender identity. At the other end of the continuum, they can identify as 100% male or 100% female. They can identify as bi-gendered, gender-fluid, or some combination of male and female. They can adopt different gender identities with different people and in different circumstances, and this is something that can remain constant, or shift and change throughout a massage or throughout a lifetime. I have worked with people called women who find that identity limiting or unbearable. Some need support to explore and express their maleness. Others find a home in a more fluid identity, while some feel right rejecting gender identifications entirely. I have held people designated as men through the grief, relief, fear and joy that can be experienced when that gender designation releases its grip. The embodied experience of penetrative pleasures can be transformative for the gender identity of men.

“Gender expression” refers to how the person you are working with presents their gender. We make assumptions based on people’s gender expression, but it is usually just the tip of the iceberg. A woman can feel butch and present as femme, or feel femme and present as butch, and the dissonance between gender identity and gender expression might or might not affect how she likes to be touched. I have worked with many cross-dressing people who disclose that they have fully-developed male and female gender expressions as part of their lives. “Ron,” who arrives at the studio as self-evidently male, may have “Rhonda” within as a secret gender identity, or Rhonda may already have a flourishing female gender expression with her own lipstick, lingerie and friends. People who present as hypermasculine men can be gay in their attractions, bi-gendered in their gender identity and female in their sex.

Biological sex is another area where we make assumptions. Based on people’s gonadal structure, we might imagine we know their biological sex. But here again, nothing is so simple as the notion we are always only either male or female would suppose. I have worked with an intersex person who recognized and re-experienced the gender assignment surgery they had as an infant as I mindfully mapped their genitals. A colleague has worked with someone identified as female who appeared to be extremely feminine, with breasts and female genitals. She turned out to be chromosomally male, with Androgen Insensitivity Syndrome. Her vagina was short, without a cervix, and she looked to increase its dilation and depth with genital massage. I have worked with pre-operative, post-operative and non-operative transgender people who experienced their biological sex as different from the one they were assigned at birth, based on their gonadal structure in infancy.

And then, of course, there are so many plot and label combinations in the area of who we are attracted to. We can be bi-gendered in our identity, queer in our gender expression, female in our sex, and attracted to masculinity. We might get tangled in assumptions that someone with this particular combination is either a straight woman or a gay man. We can be asexual or ambisexual in our attractions, fixed or fluid in our expression, gender-consonant or gender-dissonant in our sex, expressive or hidden in our identity—and these characteristics are likely to shift and evolve as we build levels of connection and trust. Erotic massage can be a safe and healing path for people who want to explore various aspects of sexual orientation and sexual preference. Queer, transgender and gender-variant people are boldly creating possibilities for all people to have a more playful and creative relatioship with gender, whatever their sexual orientation. As innovators and pioneers, they pit their bodies and desires against the status quo, and they are likely to encounter many forms of violence. Practitioners of erotic massage can offer sanctuary. The massage studio can be a safe haven where a gender pioneer can relax into embodied exploration. Or it can be another place of oppression. We need to have sufficient cultural competency to make our practices welcoming to everyone on their gender journey.


Working with Gender-Variant People

How do we make our practices welcoming to gender-variant people? First, check your assumptions. Understand that gender is not tied to genitals. These additional suggestions help bring us to a starting point.

  1. Scrutinize cisgender privilege.
  2.  Learn the language.
  3.  Ask good questions.


Cisgender Privilege

When all or part of us is cisgender, that is reinforced with enormous privilege. Our validity as a man/woman/human goes unchallenged, and does not depend on how much surgery we’ve had or how well we “pass.” Those people without cisgender privilege, or the parts of ourselves that live without cisgender privilege, lose the ability to walk through the world unremarked. Gender-variant people are stared at, whispered about, pointed at, or laughed at because of our gender expression. We face violence or the fear of violence every time we walk down the street, seek medical treatment, look for an apartment, use a washroom, apply for a job. We find that strangers assume they can ask what our genitals look like and how we have sex.

We can work to create space in the world for queer, transgender and gender-variant people by supporting their rights and addressing cisgender privilege. March in the Pride Parade. Show up at the Transgender Day of Remembrance in your community. Oppose unjust laws and advocate for human rights protection. Address transphobia and cisgender privilege when it comes up in conversation, physical structures, intake forms, workshop offerings, designs for living, and your own heart. Be explicit in your welcome to gender-variant people. Ask questions, both of yourself and others.


Learn the Language

As providers of erotic services we need to take responsibility for basic literacy in the special concerns of queer, transgender and gender-variant clients.

Somatic Sex Educator Dr. Captain Snowdon says, “When we travel to a new country or want to interact in a new community, we try to learn their language. With Transgender and Gender Variant clients this is a respectful and logical way to start. In Transgender communities, there is constant dialogue about terminology and its application for diverse members of the community. This can be both exciting—as it is a deeply creative place to be able to invent language that fits us individually—and frustrating, as it is not always easy to decipher the ‘right’ language to use with our clients.”

We need basic literacy on LGBTQ identity definitions. When it comes to erotic touch, however, we will need more understanding and sensitivity than any identity definitions can afford. The ways gender, identity, expression, sex and desire combine is individual and infinite. The biggest danger lies in making assumptions. We might assume our clients have or want to have certain body parts, or that they like or don’t like certain kinds of touch, that their genitals will or won’t function in certain ways like becoming erect, self-lubricating, penetrating or ejaculating. Sometimes your assumptions will be right and other times they will be insulting and wrong. The wrong touch, or inappropriate vocabulary, can trigger dysphoria and traumatize a client.

The anonymous author of “Transcending anatomy: a guide to bodies and sexuality for partners of trans people” (available at no charge on the internet) guides, “As a general rule, always echo the language your partner uses for their body.” They write: “Trans people’s genitals come in many different forms, and so do the terms used for them. Some trans people use the same words that many cis people use to talk about their genitals—whether to describe their anatomical form or the way they conceptualize them: vagina, penis, clit, cunt, pussy, dick, cock. Others have come up with new words or phrases specifically to describe trans genitals: diclit, click, manhole, strapless, cockpit, front hole. Some use words that are nonspecific: stuff, bits, junk, downstairs.” If you or they use toys, learn from your client how to refer to them. Does your client think of the toy as an object, or are they more comfortable discussing it as part of their or your body? You can also find ways to navigate your interactions without actually naming body parts or acts.

Honor the courage and vulnerability of any gender-variant person who comes to your practice. Show them that your respect for their gender identity will not be diminished because of how their body looks or because of the ways they want to be touched. Commit to conceptualizing their body as they do and using the language they use to describe their parts. Catch your assumptions, make mistakes, and try again.


Ask Good Questions

Sam Killerman guides, “If you aren’t sure what pronouns to use for a person, simply ask them. A good way to ask this question isn’t ‘Are you a boy or a girl?’ but rather ‘What are your preferred gender pronouns?’ This is a great question to get in the habit of asking in general, and one that will make the gender-diverse people in your life way more comfortable being in your life.”

In any offering of erotic massage, you can ask, “How would you like to be touched?” You can ask this question over and over. Asking “May I touch you in this way?” is a very different question, as sex educator Betty Martin teaches. The phrase “May I?” suggests that you are asking permission to touch in a preconceived way that proceeds from your own desires. All too often, a vulnerable client will endure this kind of touch to keep the peace and avoid insulting you. In contrast, the question, “How would you like to be touched?” invites the client to speak from their heart, and to answer in their own vocabulary, as they request touch they want without regard to your agenda. With attention to nuance, you can shift your language from prescriptive to heart-opening.

“Show me what feels good” can be a serviceable and open way to invite a client’s direction while avoiding inappropriate names for body parts. Let your client know you would enjoy and appreciate the honor of witnessing their self-pleasuring. You can also put their hand over yours and invite them to move your hand so that you touch them the way they like it.



Erotic massage can be a sacred gift in the lives of queer, transgender and gender-variant people. As practitioners, we can offer an environment for safe and respectful exploration of how their bodies feel, and how to be sexual, as they investigate bringing their inner experience of gender into the world. We can address scar tissue from surgeries (see more in the chapter on Healing Painful Sex). We can offer touch that honors each person’s internal gender experience and helps it to unfold. People who explicitly identify as queer, transgender or gender variant have special needs and concerns, but their journey to find a home within genders, between genders and beyond gender is common to every person we touch. Erotic massage can support people in exploring the touch that brings them pleasure in an environment of complete acceptance. Our work can empower each client to come home to their own body and access the body’s wisdom, wherever they are on the gender journey.



Anonymous, “Transcending anatomy: a guide to bodies and sexuality for partners of trans people,” widely available online, 2014.

Caffyn Jesse, Mapping Queer Meanings, www.queermap.com

LGBTQ Identity Definitions: A List by Sam Kellerman, available online 2014.

Sam Kellerman, It’s Pronounced MetroSexual, http://itspronouncedmetrosexual.com/

by Caffyn Jesse, www.erospirit.ca


Don’t miss Barbara Carrellas’s film:  Transcendent Bodies: Erotic Awakening Massage for Trans and Gender Non-Conforming People


© Caffyn Jesse, 2018

All rights reserved. No part of this document, words or illustrations, may be reproduced or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without prior written permission of Caffyn Jesse. The ONLY exception is short quotes shared in a review or discussion online with full accreditation to Caffyn Jesse and a link back to www.erospirit.ca.


This e-book is an excerpt from the book Erotic Massage for Healing and Pleasure by Caffyn Jesse. The purpose of this book is to educate. The author is an educator and not a therapist. The book is not intended to give medical advice or psychological therapy. Whenever there is concern about mental or physical illness, a qualified medical professional should be consulted.

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