By Day, I’m An Average British Man. By Night, I’m A “Sissy Escort”

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Shave. Moisturise. Lingerie. Heels. Divinity.

Hi, I’m Bonnie. By day, I look like every other white British man. What sets me apart is that I’m secretly making a living as an escort and exploring my sexuality and gender as I go. 

In casual conversation I’ll tell you I work in IT audit – chat so reliably boring it will only ever happen once – but the truth is I quit that job. I stopped using LinkedIn. I stopped spreadsheets and ‘catch-ups’ and started meeting strangers in hotel rooms wearing high heels and a pink wig. 

A combination of things has led me here: passion, privilege, climate fatalism, a high sex drive, and a general disdain for capitalism. 

It started innocently enough – I had bought a sexy little skirt that I had planned on gifting to a girl I was sleeping with. The pandemic had made hookups difficult, so on one particularly horny night alone I ended up trying it on myself. 

Over time the natural course of action followed; one I’ve learned is a common experience for all types of men young and old; more dressing up, more femininity, more experimenting, and eventually – hookups. I change and femininity washes over my body; a divine and graceful feeling, an earthly joy to experience and a privilege to have access to. I’d pack a bag, go out after work and get myself into sketchy situations. It was a thrill. A few more of these hookups and a pattern began to emerge; these men were saying some really nice things about me. Having given some of these same compliments myself to girls, I felt I understood their legitimacy. I started getting ideas. I even asked them about it. Could I charge for this? The last guy I slept with for free told me, “You should set your rates really high.”

Exploring My (and Their) Desires

Meanwhile, my desk job was stagnating and keeping me from enjoying my hobbies; theatre, film, acting, and writing. There is so much joy in life and I found time at my desk to be time wasted. I wasn’t spreadsheeting enough. My managers could see me slacking (only my head and shoulders, not the skirt and heels I wore under the desk.) Something had to give. 

After performing webcam shows in the evening and testing out a few clients in a cheap hotel, I glimpsed the earning potential I needed and cut myself loose from the world of international auditing. My hookups had acclimatized me to the feeling of going to bed with a male stranger and the excitement of visiting unfamiliar places, and the sums of money they were handing me made it much sweeter. With my last paycheck, I bought a cheap little work phone and booked another hotel room. Within a week I was texting clients, taking my PrEP, and stretching.

I work from a very popular website and, fortunately, reach a wide range of clientele who all help to keep me afloat. One night I could be visiting a hardware shop after hours where the owner has put out a mattress on the floor closed the shutter and dressed himself up – a too-small black wig, a leather dress, and thigh-high suede boots (an outfit I wouldn’t be seen dead in) and the next night, with a Muslim gentleman terrified about keeping our meeting a secret, going against a lifetime of cultural norms to experience a ‘girl’ like me (that was a great night, obviously.) And the next night (literally, as I write this, last night), a nerdy middle-class kid in his twenties with a bedroom full of Xbox and Warhammer wants an hour of my time to recreate his favorite pornos. Even when work is slow, I can get by at £200 (USD $225) an hour. 

“Not A REAL Girl”

So why me and not a ‘real girl?’ People want to experiment – a reliable third of my clients are married men who want to experience the sensations of giving head and are happy to pay for the privilege (and if you’ve never sucked on a deserving cock, trust me – it’s a thrill!)

There is also a shared covenant of comfort and understanding between men, the same sense I imagine exists between women when there are no men around. My clients don’t feel they have to explain themselves or keep up their defenses – we are on the same wavelength from the beginning. I don’t identify as trans, not for work or otherwise. My life is not that of a transgender person; it is only performance, wig, makeup, perfume, exercise, and certain affectations and movements which come together to cast a spell. In the UK sex industry, what I do is referred to as ‘sissy’ or ‘cross-dressing,’ but they are terms I disagree with – I’m not dressing like anyone else; they’re my clothes!

To a certain extent, I understand this business relies on my genetics – I have good skin and am comfortably endowed. Also, my outlook on life influences why I do this; I want time more than money. I am trying to find more of what truly matters to our souls – connection, moments, joy, and fun! Whether that’s the sense of adventure I get from escorting or the pleasures of life I enjoy elsewhere, I prioritize them above a soulless desk job.

Without other passions in life, I can’t say how I would feel about this line of work. It is an unsustainable job for me and it could only ever be a stepping stone. I want to create and explore life while it is here to be enjoyed, and escorting is the medium through which I am exploring gender.

I have learned that the world is already queerer than we realize. The queer ‘experience’ is happening in its own way all around us, and most surely has been since the dawn of humans. The way we feel is important to us as individuals. I see no difference between the old electrician in an ill-fitting leather dress and the young, open kid in an outlandish, gender-bending fit. It is all life – here to be lived.