Hustled and Hooked: Dating a Male Sex Worker
Before I begin, I would like to make three points. Firstly, all of what you will read from here on out is true. It may appear sensationalist, but it is not exaggerated for comic effect – this really did happen, for better or worse. Secondly, whilst I’m a big believer in legalising prostitution and thus do not want to appear ashamed of my story, for the sake of being able to find a job at some point in my life I am choosing to appear anonymous. Finally, it may be that some people who read this will have a problem with the content of this post. This could be for any number of reasons, and as such I have tried to limit how offensive this story is. However, equally, I ask that whilst reading this you try and keep an open mind – as far as life events go, this story represents a very liberating chapter of my life. I hope I can show you how taking a chance can be hilarious, and as cliché as it sounds, that you can never judge a book by its cover.
Now, with that done, on with the article! When I was asked to write about a funny or awkward relationship, I could have chosen a multitude of experiences. I mean there’s the time that a guy asked me to give him a foot job (yes, that’s like a hand job, but with your feet), which I went along with because #yolo. There was another time more recently where I lost an odds-on and actually sent two of my closest friends a picture of my dick. Every single time I’m drunk I suddenly think it’s a good idea to hit on my straight female friends (with varying degree’s of success), and I’ve lost count of the number of ex-flames I’ve bumped into whilst being attached to a different male…
Let’s be honest here – despite my anonymity, many people will recognise who the author of such an explicit blog post is. It’s common knowledge among my friends that I’m a pretty liberal kind of guy, especially when it comes to ‘fun’ times. And sure, I’m really not embarrassed to admit that I have dabbled in some things that would make my mother cringe; or any other normal person, for that matter. But it is without a shadow of a doubt that the weirdest relationship I’ve ever had was, as you guessed it, with a male prostitute.
My modern love story begins when Leo and I met, as with many homosexual encounters, over Grindr. For anyone acquainted with gay male dating apps this will probably be a familiar story, but for all those that have not had the pleasure, let me elaborate. Grindr, along with Squirt, Hornet, and to a lesser extent, homosexual Tinder, are sleazy as hell. Surprising, considering the names, eh? In a typical e-dating manner you input information about yourself and upload a profile picture. However, when such information includes your sexual position—bottom, top or versatile—and pictures vary from shirtless shots to soft porn, these apps very quickly differentiate themselves from plentyoffish.
It was on such an app then that Leo sent me a message. After breaking the ice with a number of very explicit pictures of his butt and an accompanying ‘hey ;-)’, I was suitably interested. Leo was an attractive, sexually confident man (as far as qualifications for selling sex go that’s pretty much the biggest box ticked), and as always, I was down for something casual and fun. We chatted for a bit, and agreed to meet. At this point I had no clue that he was a hooker, and it would take him six months to tell me how he really earned his white Mercedes. Yes, his Mercedes.
After having pretty good sex, we said our goodbyes, and went our separate ways. Over the next six months we chatted and met up a few times, always for sex dates, followed by hanging out. It was nice, if not bizarre. We’d been getting pretty deep, without ever going further than my bedroom. When Leo told me that he was a prostitute, I think my reply was ‘lol, u r joking’, which following that, he replied with a picture of a stack of money. In fairness, from this point the relationship wasn’t particularly funny or entertaining. Every time we would meet it would be in between him going to the gym or meeting a client, and it would consist of him flirting, followed by him trying to have sex with me, before I’d get annoyed about how I felt stuck. It used to infuriate me – I felt like our relationship was on autopilot, not really regressing or developing. It was never about being monogamous for me, but I wanted some progression from the sexual partners turned semi-boyfriends that we had arrived at. Instead we were sitting in a lull of awkward blowjobs and discussing how he gets paid an absolute boatload of money to give other men what I was getting for free.
And sure, now that I’m writing this article and I’m no longer in this relationship, I think the root of the problem was a lack of understanding on my part.
He didn’t want to give up his lifestyle or the profession that gave him so much freedom, but simultaneously he genuinely liked me and wanted me to be happy. It wouldn’t work for us to become more serious because his job was not compatible with a relationship.
Despite it being one of the most confusing and peculiar interactions, it’s one I’ve learnt a lot from. So next time an insanely attractive hooker sends you pictures of his anus over a sleazy app designed for sex, just take a moment to consider what it could lead too.