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Heather Riley.
The Gentleman's Choice. Elite VIP Companion


Hello, Friends.

I'm Heather Riley,  the Gentleman's Choice Companion. I am Elite Upscale VIP Escort Based in Chicago. I provide experiences Monday - Friday and weekends. I am Passport Ready and PreCheck to be your cute Travel Companion to fly me to where ever you are, go on vacation with you, or sponsor a tour to your area! When I'm not traveling, I am available for passion and fun in Chicago on an hourly basis or an extended date. If you've never booked a provider, I'll walk you through the steps!

Generally speaking, I offer GFE, PSE, BDSM, Kink/Fetish, Couple Friendly, Always Ready for Lunch / Dinner Dates & Overnights. The smallest sentence to capture a wide array of ways for us to spend time together.

 As a Companion, I believe in enjoying every moment we share together. While we are together I am entirely focused on you. I want to make your every dream and desire a reality. As for me, I am a former college athlete, sorority girl, well-educated twice, and described as bright, playful, and refreshing.

I love laughter and great conversation. I enjoy spending my days flirting over drinks and planning out next adventure. As both lover and friend, I am a safe space and a release from the crazy world around us. I am lots of fun, silly, sexual, erotic, naughty, and I'm not as shy as I look. Nobody would ever call me boring! I love Social Dates to sporting events, live concerts, musicals and operas, festivals, etc - all highly encouraged! Day time dates that include inducing in fine dining, massages, sight seeing, adventure, traveling - all things I love. I'm as sweet as can be and as kinky as you'll let me!
                                                             xoxo h                

"So sweet and delicious do I become, when I am in bed with a man who, I sense, loves and enjoys me, that the pleasure I bring excels all delight, so the knot of love, however tight it seemed before, is tied tighter still."
- Veronica Franco

Will sign NDA

for discerning clients.

Defiant enough to keep things i n t e r e s t i n g

Submissive enough to make it w o r t h i t


I'm a sweet, kind, passionate lover. Highly intelligent, delightfully playful, sinfully incorrigible. A little bit of a fire cracker.

Full of stories and life experience. I love to talk and have an opinion on everything, I love taking time to find out how much we have in common while we flirt over dinner. There's something interesting to enjoy about everyone. If you like pretty girls who will get you into trouble, you'll love spending time with me.


I specialize in long-term client/provider relationships with a true Girlfriend Experience tailored to needs and wants of my clients. Repeat clients welcome here.

I also offer a variety of 1-4 hour dates for clients who prefer shorter trysts.

If you've always wanted to meet me, I promise to treat you very well!


Screen, Book, Submit Deposit, Subscribe to my Socials, and send thinking of you gifts and tips!

I do not care about age, race, weight, religion, etc.

I do expect kindness, communication, honesty, and respect.

Pay my fee in an envelope at the beginning & shower before our date!

Light Screening

Deposits for Incall & Travel.

Cancellation Fees Required.


200+ Positive Reviews! Suitors may submit tasteful reviews of our time together.

$100 Reference Fee

P411 - Okays




Thank you! 


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