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.

Previous
Previous

My First Couple

Next
Next

My First BDSM Session