Juicy Jolene

View Original

How I Became An Escort

I didn't plan on getting into sex work, it just happened. And I'm glad for it.

I had moved to Chicago to live with my family after the passing of a loved one. It was a hard time and I needed a job with flexibility that still gave me time to grieve. So I looked and looked at job listings and I knew I could NOT work with other people and definitely NOT under someone's thumb. And that's when I found a dog walking job. Not the most glamorous of occupations but I love dogs and I wanted to explore the city. I walked miles and miles during the Summer and Fall of 2016. It was great. The dogs were so friendly, the city was beautiful and the people were nice. I didn't make much money, but hey I worked for myself and it was great. But I'm not from the North. At the time I was not experienced with the brutality of winter, especially in Chicago. So I knew I had to move onto something else and soon. Winter was coming.

During the day I would walk dogs and at night I would spend time with my family: watching TV or talking. There was this one show that sparked the idea in me that sex work was not only a viable option but an option at all! The show was called Blue starring Julia Stiles. It was about a single mother leading a double life. She was an accountant by day, sex worker at night. After watching Blue, I looked into sugaring (as in sugar baby/sugar daddy dynamic). I researched mainly on tumblr, which had an active sex work community at the time, and I decided that I couldn't actively manipulate people to give me money. I just don't have it in me. So the next option was escorting, which has set boundaries in place. It was more transactional and I felt better about money being exchanged for a service being provided. I did research for six months. I read blog after blog. Even watched the informative youtube videos of my now best friend, Isla Flores. I put together a loooooong screening form for all potential clients and made a free website. You can find the details of my first appointment in my first post. I was very cautious at first. I let my family member know what I was doing and they tracked my location to make sure I was safe.

It was nerve wracking at first but after a couple appointments I was estactic with the possiblities laid out before me. And here I am now almost six years later.

I know this story is not what people are expecting when I tell it. I chose to enter this profession, I wasn't forced or coerced. I don't have a drug habit to support and I'm not pimped. So sorry if that's what you were expecting. Escorts are regular people, too.