A Tryst With Chicago Escort Juicy Jolene

Well hello my loves! Welcome back to our provider interview series, A Tryst With, we're so happy to have you. Today we're catching up with the bold, the scintillating, the gorgeous,  Chicago Escort, Juicy Jolene!

We’d love to know a little of your backstory - what do you do and how has that journey been for you?

I am a GFE companion or a “vanilla” escort. I started escorting at the end of 2016 because of a TV show where the main character was an accountant by day and an escort at night. I don’t think the show was meant to promote escorting, but that’s what it did for me. It got me thinking, “That’s something I can do!” So, I started off looking into becoming a sugar baby.

After my research, I decided the boundaries of sugaring were too thin and flexible. I needed plainly stated limits, so I directed my tumblr research into escorting. After six months of research, I dove in head first and haven’t looked back. The journey into sex work for me has been enlightening and enjoyable. I appreciate the ample amount of free time this career affords me where I can focus on my hobbies. I feel blessed to have found sex work.

Is there anyone in the industry you consider a role model or someone you looked up to when you first started your journey?

As mentioned previously, I did a lot of research into escorting before jumping in. The source I used was mostly tumblr, which hosted many escorts at the time. There was one post that directed me to a woman giving advice on YouTube. She had many videos on how to maintain clientele, how to keep safe, and just talking frankly about the industry. I didn’t see anyone else doing that.

Her videos would be 15 minutes long, she would speak with this charming New York accent, and give out indispensable advice. She told me to create a Twitter, so I did. And she retweeted me! I was awestruck and tweeted back, “The great so-and-so noticed me!” She invited me out and we became fast friends. This woman is the buxom Isla Flores. I looked up to and still look up to my friend. She is a well of information and she shares it freely. She is definitely my role model in the industry.

For escorts, lingerie is a core part of our work uniform. What are some of your favorite lingerie brands, why do you love them and how do you think other brands could improve?

Sometimes people ask me where I get my lingerie because I’m a curvy girl and it’s hard to shop for BBW’s. I shop at Yandy, Ann Summers, Playful Promises, Solstice Intimates, and occasionally at plus size clothing shops like Torrid. I prefer these brands because they fit me and they have plus size options.

My secret go-to has been Ann Summers. You don’t see a lot of US providers shop there as it is a UK based lingerie and sex toy shop. A lot of their sets are gorgeous and high quality. I am voluptuous on top and definitely on the bottom, so I need extended bra sizes and bottoms that are larger than XL. The way other brands can improve is to expand their sizing to include us curvy girls! Especially for bottoms. I need a thong large enough so it doesn’t cut me in half!

As someone into the retro/pin-up aesthetic, is there anything you spend more of your budget on (like seamed stockings)?

The retro/pin-up aesthetic is something I’ve done in the past but haven’t picked back up in a while. At the time, I invested heavily into all the colors of seamed stockings from What Katie Did, a hairdresser that knew how to do the pin up curls, and a photographer who is well-versed in the pin-up aesthetic. My pin-up pictures have certainly been popular and show the playful side of my personality. I will definitely be doing more themed shoots like that in the future.

What are your hobbies and interests outside of work?

When I’m not working, I enjoy playing video games, reading, and dancing. I love playing early 2000s simulation games like The Sims 2. When reading, I prefer books of the self-improvement variety. Another hobby that I started recently is dancing. I’ve taken belly dancing and burlesque dancing classes and I absolutely love it. My body doesn't love it the next day, but I can’t get enough! Maybe you’ll see me one day headlining as the next Dita von Teese.

Has sex work influenced your relationship with your body? (positive and negatively)

I’ve learned a lot about myself, physically and mentally, because of sex work. I’ve learned what turns me on and gets me going. But I’ve also gained so much confidence in myself and my abilities. I didn’t truly know how to hold a conversation before sex work, now it comes easy as pie. Being a BBW, self-confidence didn’t come easily to me either, but sex work has really assured me that I am gorgeous, interesting, and nobody can bring me down because of my body size.

Do you find that there is a type of client who seeks you out, who you really enjoy seeing?

The clients that seek me out enjoy and appreciate ample derrières, curves, and a bubbly personality. They come to me for a judgment-free, happy, relaxed, and enjoyable time. Not to toot my own horn, but I’ve been told that I'm great company, a good conversationalist, and I instantly make them feel comfortable. I enjoy seeing clients who are easygoing, share their interests with me, and treat me well. I love learning about what makes people tick and I appreciate openness in my dates.

My favorite scent is: Pine trees.

My ideal date would consist of: Sushi dinner, drinks and dessert. ;)

Something dangerous or exciting I want to try is: Perform Burlesque in front of a large audience.

The way for a client to win me over is: Generosity and kindness.

A social cause I care about is: Environmentalism.

Want to meet Chicago escort Juicy Jolene in person?  

Head over to her profile! 👇👇👇