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Encounters of a Craigslist Fetish Worker: The Most Bizarre Sex Stories You’ll Ever Read

You’ve probably heard this tale before. A girl from a small town moves to the big city to escape her boring life and follow her dreams, only to discover she probably doesn’t have what it takes. So now what? She can’t go back home and tell her parents they were right, that she never should have left in the first place. With no college degree, no job training or experience and little skill to speak of, her options were limited. That is, until she posted in the Casual Encounters section of Craigslist and began making money later that night.
New to the business, she started by offering massages that were followed by happy endings. She quickly built a base of loyal customers so she felt comfortable upping the ante, so to speak. She looked at it as a business, and as time passed, she wanted to make more money. The only way to do this, aside from sleeping with a lot of new clients, was through fetish work.

Samantha’s* first experience in the fetish world was with a man who wanted a golden shower. He lived in Long Island though and she was hesitant because of the distance. He offered to pay for a car service to take her out there, wait for her and then take her back. She agreed. After riding in the car for over an hour, she arrived at a modern four-bedroom house. She had never done anything like this before and had no idea what to expect. He paid her upfront ($1000 not including the car service) and offered her a drink. She asked for a glass of wine as she felt she needed to loosen up a bit. He could see how nervous she was and tried to make small talk to calm her down. He told her that he was just a regular guy who worked on Wall Street, but that he happened to like it when women peed on him. This made her laugh, albeit uncomfortably. They talked for another 10 minutes and she started to relax a bit. She asked him why it turned him on and he said he couldn’t explain it, but he had been doing it for years. Then he explained what was going to happen. After she peed on him, he was going to jerk off and he wanted her watch. She hadn’t even thought about that – about how he was going to get a “release” – because she had been so focused on the fact that she had to pee on someone. So they went into the bathroom and got into shower (which was large enough to fit 12 people) and she took part in her first golden shower. He finished within minutes and then he wiped himself off. He asked if she wanted to take a quick shower alone and, having never been in a bathroom as luxurious as that one, she couldn’t say no. That was the easiest $1000 she had ever made.

Another client wanted her to do the opposite. She could not believe what she was hearing. Initially, that was not what they had agreed on. She had gone to meet him for a little, light S&M. He liked to be humiliated which seemed easy enough. She was just supposed to tie him up and blindfold him while he was wearing only his “tighty whities” and yell at him and call him all sorts of emasculating names. He also wanted the occasional smack across the face, chest or behind. For this, Samantha got paid $600. During their third encounter, he asked her if she would be up for something different. He told her that he wanted her to go “number two” on his back. Completely shocked, she said the first thing that came to her mind, which was that she didn’t have to go. He told her not to worry, that he had brought a suppository for that reason exactly. She thought about it for a few minutes and decided she had nothing to lose, but only after charging him an additional $1250. She reasoned, if she got paid $1000 to pee on someone, she should be getting a lot more for this.

Before meeting Ian, Samantha thought she had seen it all . When they had spoken online, he never specified what his fetish was, but offered her $2000 and promised she wouldn’t have to engage in any conventional sexual activity or anything dangerous. In fact, he told her that she would barely have to touch him. Slightly nervous, but highly curious, she agreed, even after he told her that his sexual proclivities prevented him from carrying on a relationship because no one, not even him, understood why he was turned on by what he was. He told her to strip down to her bra and panties and he began taking his clothes off as well. As he pulled down his pants, she noticed that he was wearing diapers. Trying not to laugh, she stared at him with bewilderment. Without even mentioning the diapers, he asked her to hit him in the crotch. The first time she didn’t use a lot of force because this went against conventional wisdom. “Harder,” he implored, and she did just that. She couldn’t believe she just watched a grown man cum in diapers after being punched in the privates, and that she got paid for it. Not wanting to make him feel like a freak, she didn’t question his predilections. The next time they met, he asked if he could call her mommy.

Then there was Simon. He also had some requests that she was confounded by. Originally from Germany, he told her that he frequented S&M clubs back home and that was where he developed specific tastes. He unzipped a small leather bag he called his starter kit and began pulling out q-tips, a lighter and a dildo. He lit the biggest candle he could find and then asked if he could play with her feet while the wax got hot. As she bent down to take off her shoes, he pushed her hands away and did it himself. He caressed her bare feet slowly, and began to suck each of her toes one by one. Noticing that the wax had started to melt, he asked her to drip it on him. Next, he instructed her to stick as many q-tips in in the hole at the tip of his penis as she could fit. Speechless, she slowly did as she was told, stopping at three. He told her she could fit more in, having once made it to five himself. She put one more in but stopped there, distraught by the realization that now she had to take them out. All that was left from the kit was the dildo, but she wasn’t sure what (or who) it was for. Simon handed the life-size toy to her and asked if she would be comfortable using it to penetrate him anally. Without even thinking, she immediately said no. This was a line she couldn’t bring herself to cross. The $600 she made was half what she would have had she done everything he asked. Suffice to say they never saw each other again.

*Name has been changed

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