My Debut as a Craigslist Hooker

There are plenty of ways to make money as a broke student in London, but I decided that allowing older men to fellate me for money was the easiest. Most importantly, it met my three requirements for a job, being something that: a) I could organize from my laptop b) paid well, and c) required little skill. Despite never having a homosexual experience in my life, my decision to begin hustling older gay men seemed natural. I grew up in a small town and pretty much always figured that this was the sort of thing that went down in London Town. So, when a friend at uni told me about Craigslist prostitution, I figured it’d be easy enough.
    
Once on the site, if you wade through the bog of requests for incest, bestiality, and every other bizarre fetish you can imagine, and ads so lonely they make you want to weep, you find a surprising amount of gay guys who are turned on by the idea of pleasuring straight men. Ads such as "r u str8? looking for £un?" and "I want to suck some str8 guy's dick for cash" are two-a-penny. Although not exactly a raging "straight," this is my predominant persuasion, so these ads seemed perfect for me.
    
Once I'd realized that online prostitution was my calling, I set about replying to as many Craigslist ads of this nature as I could. After a half-dozen emails back and forth, I finally had a date set. The guy I had chosen seemed nice enough; a chubby Indian guy in his mid-40s who was firmly in the closet and lived alone. I didn't give much thought to the date, running on auto-pilot right up until I stepped off the platform in Leyton. As I followed incremental directions texted to me every five minutes my certainty of the brilliance of my get-rich-quick scheme did start to wobble. No one knew where I was, and even the few people I had told about my plans weren't aware that today was the day. However, I'd come too far to turn around now, so I bought some beer and moved on. I arrived on his street and, after being texted his address, made my way up to his door.
    
Excusing the mess in his house and offering some awkward hellos, he ushered me upstairs. The house was absolutely filthy. Not a "had a busy week, no time for cleaning but I'll get round to it" kind of filthy, but more of a "I'm hiding my mother's dead body under this pile" mess. Seriously, there were stacks of cutlery in the hallway that were only a little shorter than me. As I was pushed towards his bedroom my heart sank—this was not quite the no-strings-attached situation that I had pictured. There were tea-light candles, Heart FM was playing, a towel lay on the bed, and a strong scent of lube was wafting my way. A distorted sense of romance lay far too heavy in the air for my comfort. Despite my creeping sense of dread, the following 40 minutes or so went surprisingly well. I followed the directions of my client, moving about as he said, and the arrangement seemed to go without a hitch. I lay down on the bed and tried to relax. My first blowjob from a man was surprisingly similar to any other I'd had, if I closed my eyes I could slip right into my happy place and imagine any number of beauties replacing the chubby guy servicing me. I didn't even twitch as he gave me my first rimming to the smooth noises of Lionel Ritchie. However, I did balk when he tried to creep a sneaking finger into my ass—that was NOT part of our agreement. But a slap on his wrist sorted that out. Apart from this, our date passed without major incident.
    
I left and, despite repeatedly trying to convince myself that I was comfortable with it all, managed to spend a large amount of my new cash on comfort food, drinks, and cigarettes on the way home.
    
I have yet to see that first man again, but an awkward relationship seems to have developed between the two of us. As the weeks followed, I received a number of texts from him, all of which demanded my immediate appearance at his house. As time went on, as I continued to reject him, my one and only client grew more and more frustrated. Eventually, not long before I wrote this, he wrote me a depressing text message… he was… breaking up with me. He was ending it. He was sweet about it. He told me that "it just won't work" and that "he couldn't do it." But, as is often the case, all it took to soften his resolve was a bit of time. After little more than a week he was texting me again. He is trying to win me back! Unfortunately for him, I'd reached the limit of how much creepy internet shit I could handle, so he hasn't been receiving any replies for a while—not that that seems to deter him.
    
After a couple of similar experiences I decided that turning tricks wasn't for me, and am attempting other, slightly less soul-destroying ventures. Like writing. But honestly, I wouldn't discourage you too heavily. If you're a lazy fuck and you need the money, why not? Just make sure you've got your happy place on speed-dial.