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Ambisexuality: The Anatomy of Transerotic Desire

Ambisexuality: The Anatomy of Transerotic Desire

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Ambisexuality: The Anatomy of Transerotic Desire

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May 31, 2019


Ambisexuals are men who are erotically attracted to 'women with a penis'. Michael simply smiled and said, "I've never been with a man. For me, a trans woman is a woman with masculine genitals, but she is still a woman. She looks like a woman and she acts like a woman." It's the 21st century. Trans women sex workers go to great lengths to meet these needs. Tens of thousands of men like Michael currently live around the world. You might think this is a modern development made possible by sex-change technology. But meticulous research reveals that this unrecognised sexual orientation has persisted across all major cultures throughout recorded history. In spite of this, almost nothing is known about ambisexuality. What motivates their sexual orientation… and the trans women they are drawn to? This book has fascinating anecdotal stories and hard data which leads to deep insights. It will make you re-evaluate what you think you know about human sexuality in an era of growing acceptance of gender diversity and sexual expression.
May 31, 2019

Über den Autor

Over the past 25 years, James has undertaken in-depth doctoral and post-doctoral study of trans women and their clients. He has worked with various gender organisations in the United States and Australia, and has immersed himself in the lives of the people who appear in this book. He has interviewed gender luminaries such as Carmen Rupe and Georgina Beyer and, equally, has interviewed many people who remain unknown. James has a deep interest in wanting a better world and this passion is expressed in different ways. After helping establish the 'Deep and Meaningful Conversation Meetup Group' in the United States to stimulate engagement on issues of social significance, he founded similar groups in Australia and New Zealand. James lives with his wife in New Zealand and the United States.

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Ambisexuality - James Watson


James Watson

Austin Macauley Publishers


How to access the Ambisexuality interviews

About the Author

About the Book


Copyright Information



Part 1


1. Ancient Worlds

2. Modern Worlds

Part 2

Women with a Penis

3. Transitioning Rites

4. Sex Working Rites

Part 3


5. A Hidden Culture

6. Erotic Desires

Part 4


7. The Anatomy of Transerotic Desire

Physical Bodies

Genital Display as an Indicator of Sexual Interest

The Specific Sexual Appeal of a ‘Woman with a Penis’

Contrasting Erogenous Zones of Males and Females

Psychological Orientations

High levels of attention-seeking and seductive behaviour

The Attraction to Novelty and Impulse

Predisposing Sexual Histories

Flexible Social Boundaries

Cultural Environment

The Atypical Lifestyles of Trans Woman Sex Workers

Entertainment Performance


Parties and Nightclubbing


Attitude Towards Clients

Client Atypicalities

Kings Cross Sub-Culture

Tenderloin Sub-Culture

Navy Sub-Cultures in South East Asia

Technological Environment

The Use of Feminising Technologies

The Availability of Transerotic Resources

Physical Environment

Distinctive Soliciting and Work Spaces

The Holistic Network of Atypicalities

8. Ambisexuality: An Unidentified Sexual Orientation

Terms and Definitions

Sexual Services




How to access the Ambisexuality interviews

Interactive QR code tags

Some of the trans women and one ambisexual man participating in the research for this book agreed to be filmed. This lets you engage more directly with the book’s content. You can see this filmed material whenever you find one of these designs on a page:

These are QR code tags. Simply download a QR code reader onto any device such as a mobile phone or tablet which contains a camera. You can then hold the device in front of any of the nineteen QR code tags scattered throughout the book to access the filmed material.

Download your free QR code reader

Download any QR code reader by clicking on ‘Apps’, then clicking on ‘Play Store’ (for Android devices) or the ‘App Store’ (for Apple devices).

Type in ‘QR code reader’ in the search bar and search.

A number of QR code readers will appear. Some are free, but others are not. Choose one of the free readers.

Click on ‘Install’, then follow the prompts.

Once installed, a QR code reader icon should appear on your screen. It should be on your desktop or in your ‘Apps’.

Use your QR code reader

After downloading is complete, click on the QR code reader icon.

Hold your mobile device over one of the QR codes that appear in this book. Point your camera so that you clearly see the QR code on the screen of your device. When the device recognises the code, the reader will automatically identify a URL link to the interview, which can then be played.

About the Author

Over the past 25 years, James has undertaken in-depth doctoral and post-doctoral study of trans women and their clients. He has worked with various gender organisations in the United States and Australia, and has immersed himself in the lives of the people who appear in this book. He has interviewed gender luminaries such as Carmen Rupe and Georgina Beyer and, equally, has interviewed many people who remain unknown. James has a deep interest in wanting a better world and this passion is expressed in different ways. After helping establish the ‘Deep and Meaningful Conversation Meetup Group’ in the United States to stimulate engagement on issues of social significance, he founded similar groups in Australia and New Zealand. James lives with his wife in New Zealand and the United States.

About the Book

Ambisexuals are men who are erotically attracted to ‘women with a penis’.

Michael simply smiled and said, I’ve never been with a man. For me, a trans woman is a woman with masculine genitals, but she is still a woman. She looks like a woman and she acts like a woman.

It’s the 21st century. Trans women sex workers go to great lengths to meet these needs.

Tens of thousands of men like Michael currently live around the world. You might think this is a modern development made possible by sex-change technology. But meticulous research reveals that this unrecognised sexual orientation has persisted across all major cultures throughout recorded history.

In spite of this, almost nothing is known about ambisexuality. What motivates their sexual orientation… and the trans women they are drawn to?

This book has fascinating anecdotal stories and hard data which leads to deep insights. It will make you re-evaluate what you think you know about human sexuality in an era of growing acceptance of gender diversity and sexual expression.


To those who accept people who are different

Copyright Information

Copyright © James Watson (2019)

The right of James Watson to be identified as author of this work has been asserted by him in accordance with section 77 and 78 of the Copyright, Designs and Patents Act 1988.

All rights reserved. No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without the prior permission of the publishers.

Any person who commits any unauthorised act in relation to this publication may be liable to criminal prosecution and civil claims for damages.

A CIP catalogue record for this title is available from the British Library.

ISBN 9781528910361 (Paperback)

ISBN 9781528959568 (ePub e-book)

First Published (2019)

Austin Macauley Publishers Ltd

25 Canada Square

Canary Wharf


E14 5LQ


So many people have contributed to the research, writing and completion of this book. To all those who have assisted in a myriad of ways – providing helpful information, revealing sensitive personal details, giving practical assistance, editing manuscripts, encouraging and mentoring me – I thank you. Without your support, this work would not have happened.

But there are two people who have encouraged and mentored me more than any others: Frank Lewins who, for 10 years, was my Masters and PhD supervisor and a very good friend; and my wife, Wendy, who took over this role. Thank you both for your warmth and thoughtful guidance.

If thinking never deviated from what is normal, nothing would ever change.


There are not four sexual orientations but five: heterosexual, homosexual, bisexual, asexual and ambisexual. This is borne out by the evidence of history (all of these orientations have existed in some tangible form); the substantiation of the cross-cultural record (they are universal, not culturally specific) and the sheer number of people who express a particular romantic and sexual desire when they are not culturally repressed from doing so (representing a statistically significant population). There is, of course, a spectrum of gender identities, but sexual orientation is different. Where did the idea come from that ambisexuality – an unrecognised sexual orientation – exists among men attracted to ‘women with a penis’? Notions like this were the last things on my mind when I first started my sociological field work over twenty years ago.

The year was 1996 when I began conducting interviews in Kings Cross, Sydney, Australia, as a PhD student doing my initial research. I naïvely sought to engage with male-to-female (MTF trans people to develop an understanding as to why people who were born as biological males wanted to live permanently as women. It became apparent that many trans people living there worked as sex workers and that nearly all of them chose not to have sex reassignment surgery – that is, there was little incentive or desire to have their penis removed surgically and replaced with a neo-vagina. These findings seemed to fly in the face of all that had been written about trans women at the time.

Back then, trans people were referred to as ‘transsexual’ or ‘transgender’; and were commonly defined as people who emotionally and psychologically felt a belonged to the opposite sex or gender. What was important was to do everything possible to change biological sex to be consistent with these feelings. The literature suggested that all trans women wanted – even demanded – sex reassignment surgery (SRS), so what I was being told was baffling. I asked the trans women I interviewed what motivated their decision to retain the penis. Was it the high cost of surgery? Was it the limitations of surgical outcomes? Most answered that it was not in their interest to have sex reassignment. When I asked what was meant by this, a typical response was: ‘Well, you have to cater for what the market wants, honey, and that’s what men want!’ The happily married ‘heterosexual men’ who made up the vast majority of their clients were not looking for the sexual services of a female, but neither did they want intimacy with a male. These men were attracted to a different incarnation – a ‘woman with a penis’. I was so astonished by the responses I was getting that I discussed them with my PhD supervisor, Frank Lewins. Frank’s research had taken a different path. He had recently published a book on MTF trans women, but his work had focused on individuals who had sought SRS. As such, he had little familiarity with the trans women I was encountering. So I decided to investigate the matter further by searching out the published work of other social researchers. Although there were many studies of the trans community, most of the references to sex work were incidental. Researchers were more concerned with other issues such as gender discrimination and the range of transformative technologies that were available. There were also many autobiographies which recounted the stories of the enormous physical, social and emotional changes trans women endured when coming out. Typically, these narratives described their lives before, during and after transition, and reflected on aspects of the changes that had been experienced. A mere handful of studies referred to trans women sex work itself, and these were generally brief narratives that focused more on aspects such as the inherent dangers of working on the street or the HIV/AIDS risk and less on ‘the mechanics’ of what actually took place when sexual services were provided. Most intriguingly, there was silence about the all-important role of their clients.

With my PhD research proposal finalised, I set about conducting interviews. The prime focus at that time was on the lives of the trans women who offered sexual services. During this first period of research, I learnt a great deal about their backgrounds, their friends and family, their daily lives, their concerns about gender and, of course, their work in the sex industry. What was so striking was how different the trans women who performed sex work were from those who did not. These women inhabited very different worlds: they had distinct social networks, their attitudes about transitioning were not the same, and their lives revolved around their occupational employment. As my field work proceeded, I started to wonder about the involvement of the clients who drove this demand.

The year was 2001. The field work for my PhD on trans woman sex work had been completed, but in the process, I had become intensely curious about the lives of the clients who continued to lurk in the shadows. I could see that their role was pivotal, and I now wanted to understand what motivated their sexual desire for non-operative trans women. After all, it was their agency that sustained the lives and even the identity of the working trans women who had become so well known to me. I wondered, then, what an investigation of clients’ interest in with ‘women with a penis’ would reveal. From an historical perspective, how long had a sub-culture of men expressed this erotic attraction? And how prevalent was this form of sexual desire in other world cultures? Did some women as well as some men have a sexual interest in trans women? Most intriguingly, what motivated clients who quite patently understood the genital status of the trans women to pay for sexual services? Was this erotic interest a fetish or – as I was beginning to suspect from the sheer number of clients I knew to exist – an unrecognised sexual orientation?

After graduating, I vowed to find the answers to these questions. I understood the importance of the sex workers’ views on this, but I also recognised that the clients themselves were the only ones who could explain or in some sense rationalise their own erotic interest in trans women. The literature review revealed an understanding of the circumstances and motivations that lead sex workers to engage in sex work, but very few had sought to understand the motivations or circumstances of the clients. Trans woman sex work involves two parties – the client and the sex worker. Any research which restricts analysis to only one party will obviously produce a rather one-sided perspective if the whole phenomenon of trans woman sex work is to be understood. So my post-doctoral research focused specifically on the role of clients.

From 2002 to 2007, I conducted further field work gathering new data to make intelligible the motivations, behaviour and aspirations of the clients. This is something that was then and until now has remained missing in modern scholarship on trans woman sex worker-client relations.

I knew that access to clients would be challenging. Even though it was possible to gain the trust of working trans women, few wanted to risk scaring their clients away by mentioning their acquaintance with me and my research. Even when the subject was broached with clients, the likelihood of gaining their willing participation was remote. Fortunately however, there were some individuals who agreed to be interviewed.

It occurred to me that although some clients might find face-to-face interviews too confronting, they possibly would agree to complete a detailed questionnaire. This turned out to be a very effective way of acquiring research data which revealed important new information. In particular, it helped validate the conclusions reached in the second half of the book.

The client research involved nine face-to-face interviews supplemented by the 28 clients who completed the questionnaires, making a total of 37 responses. The trans woman sex worker research involved 27 face-to-face interviews and psychological personality profile questionnaires, supplemented by a further 10 stand-alone personality profile questionnaires, also making a total of 37 responses. To evaluate and contextualise these responses, these results were compared to the information obtained from face-to-face interviews with 17 non-sex working trans women, 13 male sex workers, 6 female sex workers and 8 other individuals: a trans woman escort agency owner, an hermaphrodite, two female-to-male (FTM) trans men, a safe house sitter, a store owner who had observed trans women soliciting for many years, a clinical psychologist who worked with trans woman sex workers and the mother of a 15 year old trans woman who had given her approval for her biological male son to undergo hormone therapy to become a woman.

The client interviews provided a fascinating insight into a facet of human sexuality I could hardly have imagined. As the anatomical description of a ‘woman with a penis’ was related over and over in a succession of interviews, I began to wonder if I had stumbled onto something that applied more widely than I originally thought.

The year was 2007. The task of writing this book was underway, and I once again reviewed the historical and cross-cultural research on feminised male sex work. I was no longer content with what I had previously uncovered in my PhD literature review. This time, I really trawled through the digital and print media and bit-by-bit, accumulated a significant body of evidence that confirmed what my field work had revealed. It soon became apparent that a persistent sexual desire for feminised males – ‘women with a penis’ – is threaded through human cultures. The results of this research are detailed in the first two chapters of this book. When these findings were combined with the results of the field work, no doubts remained about the existence of this previously unrecognised sexual orientation.

Clients were neither heterosexual nor homosexual. Instead, these men fantasised about and actively sought ‘women with a penis’. These men were, as will be seen, ambisexual. Given that there was no shortage of clients, the nagging question that remained in the back of my mind was: why hadn’t this sexual interest in ‘women with a penis’ been uncovered before? It became evident that there were good reasons for this. The strong social pressure to conform to one of the four existing sexual orientations means that most people, including clients themselves, view their erotic preference for ‘women with a penis’ as decidedly transgressive. Despite the growing acceptance of gender diversity and toleration of relationships which vary from stereotypical norms, these men were uncomfortably aware that most people in the wider community – including their close friends and family – still viewed their involvement with trans women as ‘perverted’ and therefore unacceptable. To this day, clients are extremely secretive and guarded about their sexual preferences, and interviews with them are extraordinarily difficult to obtain. Their existence has largely passed ‘under the radar’, and even when their presence is acknowledged, these men are largely inaccessible to social researchers. For this reason, no significant research has been done with them and information about their motivations and sexual orientation is meagre, if not negligible.

It is now 2019. A great deal of time has elapsed since I began this journey and much has changed. Although technology, gender labelling and modes of soliciting have demonstrably altered, the phenomenon of ambisexuality has remained constant. When viewed through the prism of history and culture, there is every reason to be certain the phenomenon will continue.

Irrespective of whether one accepts the premise that a given sexual orientation is ‘natural’ or not, the fact is that there are many, many clients – literally thousands of men in most of the larger cities of the world – who consort with non-operative trans woman sex workers on a daily basis. Many of them can be accurately described as having an ambisexual orientation. These figures are derived from the number of classified advertisements listed on the internet and in newspapers and magazines. In San Francisco, for example, 46 non-operative trans woman sex workers (excluding transvestites and cross dressers) had advertisements on, 18 had advertisements on and 24 on, giving a total of 88 classifieds in December 2016. This did not include Craigslist or any other classified services. At the same time in Sydney, 74 trans woman sex workers (excluding transvestites and crossdressers) had advertisements on Locanto, a worldwide online classifieds network. Conservatively, if these trans woman sex workers attracted only one or two clients per day, it is not unreasonable to guess that at least 500 clients were being serviced each day, and around 2,500 clients were being serviced in each city each week. There are even more men who view photographs and videos or read erotic stories about non-operative trans women on the internet, on DVDs or in printed magazines.


What’s in this book? Part 1 provides compelling historical and cross-cultural evidence for feminised male erotic desire and introduces the idea that attraction to the incarnation of a ‘woman with a penis’ might be the preferred sexual orientation of a small but significant number of men. What is most intriguing is the absolute persistence with which this pattern repeats itself across cultures and across time. Buoyed by consistent client demand, modern trans woman sex workers and their forebears appear to represent a universal social pattern that keeps appearing in the historical texts of all major cultures. Sometimes, the evidence for their existence is fragmentary, sometimes it is inferred, but mostly it is blatantly obvious. This extraordinary pattern of social and sexual behaviour is recorded in both the ancient and modern worlds which, for the purposes of this book, are divided into the periods before and after 1950.

Chapter 1 ‘Ancient Worlds’ corresponds to the period in history before trans technologies – such as the use of hormones, sex reassignment surgery and cosmetic surgery – became available around 1950. The chapter is structured to provide a vivid description of feminised males and their clients in a very broad range of historical cultural settings. It suggests that the concept of some male clients being erotically attracted to a ‘woman with a penis’ incarnation is universal in each of these cultures. The historical records suggest that the berdache in North America, young feminised male prostitutes in ancient Greece and Rome, the ginks in Egypt, the xanith in Oman the shaman in Siberia, the hijras in India, the male geishas in Japan, the sodomites in the Netherlands and the mollies in England shared identities as ‘women with a penis’, and engaged in sex work with their male patrons.

Chapter 2 ’Modern Worlds’ examines the technological and cultural shift that progressively changed the expression of feminised male prostitutes around the world after 1950. The chapter starts with the medical transformation of George Jorgensen becoming Christine Jorgensen, and this ‘sex change’ inspiring Harry Benjamin to coin the term ‘transsexual’. The concept of a trans identity and the use of transformative technologies such as hormone therapy and sex reassignment surgery are introduced. The attendant concepts of the ‘elective’ and ‘extant’ trans woman which fall out of the field work done for the PhD are developed. These two identities distinguish between extant trans women who wish, as far as possible, to complete their transformation and live their lives as women in the wider community; and elective trans women who wish to appropriate some female sex and gender attributes but not others. Most notably, elective trans women do not wish to lose their penis. The chapter then shows how ancient world cultures have modernised – how the feminised males who provided sexual services to their clients have evolved to take advantage of the new transformative technologies: how, for example, the hijras in India, the travesti in Brazil and the waria in Indonesia have appropriated them.

Part 2 provides a vivid picture of the lives of elective trans women working in the sex industry. Chapter 3 focuses on the trans aspects and Chapter 4 on the sex work aspects of their identity.

Chapter 3 Describes the early life experiences of trans women, the transformative changes they undertake and the challenges associated with ‘coming out’. Facets of transitioning such as acquiring women’s grooming methods, learning how to move and speak in characteristically feminine ways and choosing suitable clothing styles and accessories are discussed. From the common sense of social dislocation in their pre-adult years, the reasons for undertaking their transformative ‘rites of passage’ become readily apparent. As mentioned earlier, one of the major research findings was that there are two discrete categories – extant and elective trans women. How and why these women are so different is clearly articulated. The selective use of feminising regimes such as hormone therapy and electrolysis and the reasons for rejecting SRS are considered. At the end of the chapter, the unique identity of elective trans women is compared and contrasted with those of men, transvestites and extant trans women in terms of gender presentation and the use of sex reassignment surgery and other feminising technologies.

Chapter 4 Describes trans women’s involvement in sex work in detail. It explains what factors induce trans women to work in the sex industry and how that work patterns their daily lives. On one hand, stories are told about the difficulty experienced in obtaining and keeping conventional jobs. On the other, an admission is frequently made that most kinds of conventional work are found to be boring and unrewarding. This is not surprising in view of the scores that elective trans women achieved in the NEO-PI-R personality profiles conducted as part of the field work. In contrast to this, becoming sex workers provides many benefits and a typical ‘day in the life’ of a trans woman sex worker is described. Trans sex workers enjoy the attention of prospective male clients, earning lucrative incomes, using drugs without losing their employment, and, generally, having more choice and control over their working conditions. Almost half the chapter is devoted to a discussion of the sexual services provided. The narrative reveals some intriguing aspects of performing sex work, such as what sexual services are provided to clients (including the contrast between generic services provided by all prostitutes such as fellatio and services that are uniquely provided by trans woman sex workers. The juxtaposition of a trans woman’s feminine body and active penis becomes the main point of difference from other sex workers. The final part of the chapter concludes that sex work is rewarding for a number of reasons. Most importantly, it connects them with other trans women and with clients – both of whom accept and value their trans status.

Part 3 turns the focus of attention to the clients of elective trans woman sex workers. Locating clients and gaining their agreement to be interviewed was exceedingly difficult for several reasons. Firstly, compared to females, the number of trans women who participate in the sex industry is small, so there are fewer clients available to be approached for a prospective interview. There was also a strong reluctance on the part of the clients to be interviewed. Like the prostitutes, clients are aware of the stigma associated with their transerotic desire. There was a clear perception that mainstream society regards the sexual services provided by trans woman sex workers to be deviant, perverse and therefore, unacceptable. A further complication that worked against clients agreeing to be interviewed was that some clients – particularly younger ones – do not fully understand their own erotic desire for a ‘woman with a penis’. It is confronting to clients, let alone trying to explain this preference to others. Such views are reminiscent of the attitudes once expressed towards gays and lesbians. Clients are fully aware that they do not conform to an orthodox heterosexual, homosexual or bisexual pattern of sexual desire. These all act as powerful disincentives to openly discuss their sexual preferences and erotic desires.

Chapter 5 Begins with a brief review of the research findings on the clients of all sex workers, then specifically focuses on clients of trans woman sex workers. The narrative then turns to the main theme of the chapter, introducing the clients who participated in full interviews for this research. A short biographical sketch of each client is provided and the motives for obtaining sexual services are described. Readers find out who clients are, where they come from and why they have an erotic preference for non-operative trans women. In many cases, the regular clients only consider trans women as sexual partners. Several clients have consorted exclusively with trans women for many years. Despite this, clients also reveal that living in a committed relationship is challenging. Most describe themselves as ‘heterosexual’. There are complex reasons for this which are discussed in detail.

Chapter 6 Shifts the focus to understand what motivates men to pay for the sexual services of a ‘woman with a penis’ when female or male prostitutes are much more readily available. Many clients were married or living in de facto relationships and most were employed in conventional jobs. It also became clear that homosexual men were not interested in sexual relations with trans women because they look and act like women, not men. Similarly, the vast majority of trans women indicated that they were not interested in advances from gay men because they wished to be treated like women, not like men. In short, trans woman sex workers did not see themselves as ‘homosexuals’ and nor did their clients. The details of the sexual encounters between prostitutes and their clients tell a great deal about their erotic preferences. In summary, the narratives indicate that the sexual preference of men for ‘women with a penis’ is something categorically distinct from both heterosexual and homosexual orientations. Consorting with a trans woman is not a ‘stepping stone’ to homosexuality – it is an end in itself.

Part 4 explores the meaning and significance attached to men’s attraction to ‘women with a penis’ using a deeper level of analysis.

Chapter 7 Introduces a new analytic model called holistic analysis to develop a more meaningful understanding of trans-client relationships. Holistic analysis is a multidisciplinary approach which seeks to explain this phenomenon by examining five dimensions of human interactions: physical bodies, psychological orientations, the cultural environment, the technological environment and the physical environment. Each dimension adds insight in its own right, but it is only when they are all considered together that a complete picture of trans woman sex worker-client interactions emerges. Three specific client sub-cultures are identified from the field work done for this book: Kings Cross in Sydney, the Tenderloin in San Francisco and the navy sailors who sought the sexual services of trans woman sex workers when visiting overseas ports in South East Asia. Just as the soldiers and sailors of antiquity were known to have a taste for feminised male prostitutes, modern sailors were found to continue this tradition. Although having sex with ladyboys and beanies is widely seen by many sailors as an initiation rite

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