Note: This takes place in the USA.
My first SD, I met off CL. I had been interested in sex work for a while, but the idea of meeting a stranger to have sex for an hour or two in some sleezy motel seemed a bit sketchy to me. I kept responding to CL postings and then freaking out when men would explicitly detail what they wanted to do with me... and then ask me to meet them at their townhouse in the middle of nowhere! No thank you, even if they did promise me enough money to pay my rent. I was pretty desperate for money in those days, and was barely scraping by every month.
This guy wanted me to come to his townhouse, but it was in a very upscale part of town, and he was funny, gentlemanly, and respectful by email and over the phone. He gave me his real name, which I was able to screen and verify, and gave me the address of his rental house in advance. I left his name, address, and phone number with my best friend before I headed off to his place.
I had to take the bus there, but he met me at the bus stop and walked me back to his place. He was incredibly cute! He had ordered sushi and we ate in... mmmm, yummy. After that, we just watched TV, got to know each other, and cuddled. I was flirty, he was blushy and non-aggressive, etc. It felt pretty similar to an IRL date. We ended up retiring to his bedroom... and the sex was great! In the morning, he gave me $500. Not quite up to the going-rate for escorting in my town, but I knew that this was different than escorting. This was like getting paid to date!
Anyway, the guy said he wanted to see me again, but he told me that there was a slight problem. His girlfriend was his accountant, and she had noticed the large cash withdrawal. He usually paid for all of his expenses by credit card or check, so this was suspicious to her. He told me he wanted to see me again, but he'd have to pay me by company check. I was suspicious, but I googled his company and found a hit. He had been quite delightful company before, and the money was good, and I decided finally that I didn't have much to lose but had plenty to gain. So I decided to see him again.
Two days after I saw him again, his check cleared! Or at least, I thought it did. The amount of the check was added to my available balance. So I saw him again, and again. A total of four times. After the fourth time, I checked my bank account again. I hadn't deposited the fourth check yet. I had a negative balance. Not only had the last two checks bounced, but my bank had charged me exorbitant fees as a result, wiping out any balance that I'd had in the account previously. I called him and demanded an explanation, he pretended to call his bank, and told me that it was a mistake and that it would all be sorted out by Friday. I didn't believe him, but I didn't know what to do except wait.
A few days later, I was chatting online with him about the expensive camera I wanted that cost a couple grand. He immediately jumped on the opportunity and offered to buy it for me and cancel the bounced checks, and then just give me a couple hundred in cash at our next meet to cover the bank fees. I agreed, but at this point, I didn't really believe him. I was just sort of playing along out of curiosity and trying to plot my next move. I asked him to send me a confirmation email for the purchase, and he forwarded me one from a small company that I had never heard of. I googled the company and found their website. The did not have the camera I wanted listed on the website, but they had several other cameras listed. I called their customer service line and asked if they had the camera listed on the receipt in stock, or if they'd had it in stock anytime recently. Of course, they did not. The confirmation email was fake.
I brainstormed with a couple of my friends about what to do to get this guy back. He was bugging me for another date. Should I accept the date, leave the front door unlocked, and then have some of my friends come in with baseball bats and threaten him until he gave me the money? Should I accept the date, do the deed, and then steal his cell phone, wallet, and very expensive laptop while he was sleeping? Should I pretend to be unavailable but try to think of something better in the meanwhile?
Ultimately, I didn't see him again, and ended up letting things go. I do know from my interactions with his bank that his account existed previously but didn't exist anymore, which made me think that the checks themselves were real and thus his name probably was too. I had spotted a couple of bills with his name on them in his house also. So I've thought about taking legal recourse, but ultimately, I haven't. Technically, of course, what I did was legal. We never even discussed sex before the meeting, and the cash compensation was clearly specified as being for my time. Legal recourse sounded messy though. I didn't care if anyone knew what I had been doing, but it just sounded like it would probably cost more than it would gain me. And that's only if I was even right about his name being real.
Afterwards, I tried to think clearly about the experience and reflect on it. I could identify several mistakes I had made out of desperation. I had made more money than I had lost, and he hadn't been lousy to be with, so I had really just lost some time and been tricked by someone. It could have been a lot worse. Ultimately, I had also broken the ice on sex work and would be less fearful about trying it again, as well as learned some lessons about what I was and was not comfortable with.
One of the biggest conclusions that I drew from this is that men who were requesting extended dates for lower rates than escorts were charging were probably all phonies looking for cheap or free sex! I was pretty resolved to try escorting the traditional way. Per-hour flat rate, no exceptions. I felt confident that this would give me a better shot at success. In some ways, I was right. That strategy would be successful in ensuring that nobody tricked me again. But in other ways, I was obviously quite wrong. I had not really heard of or considered the concept of a sugar daddy yet though...