Meet Heather Riley.
The Gentleman's Choice.
The Crown Jewel of the Everleigh Club.

Hello, New Friends! Familiar faces, I'm happy to see you again. 

I'm Heather Riley,  the Gentleman's Choice Companion. I am Elite Upscale VIP Escort Based in Chicago. I provide curated experiences during the work week Monday - Friday and fun lazy Weekends. Casual or dressed up, I am a total babe. I am available for dates in the Chicagoland area or I can come to your city! 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 city! I am an expert level traveler. And I love that airport bartenders don't blink when you're having cocktails at 7am. When I'm not traveling, I am available for passion and fun in Chicago full time on an hourly basis or multi-hour dates such as 4 Hour Afternoons at the Adult Pool Hotels, Broadway Shows, Summer Baseball, Indulgent Dinners at Michelin Star Restaurants or Steakhouse, even Overnights and multi-day trips! My schedule is up-to-date and posted for your planning purposes.If you've never booked a provider, I'll walk you through the steps! It's very easy and simple. I'm a very sweet and friendly girl, I'll take good care of you.
 

Generally speaking, I offer a wide range of dates featuring GFE, PSE, BDSM, Kink/Fetish, Couple Friendly, Always Ready for Lunch / Dinner Dates & Overnights. That is the smallest sentence to capture a wide variety of ways for us to spend time together. The amount of time we spend together is up to you! I recommend a 4-6 Hour Dinner Date to start for new friends. However, I am available for 1 hour dates to multi-date dates! Sometimes I have flexibility to extend if we're having too much fun and dont want to slow down. No matter the duration, we will have so much fun and the date will feel like it ended too soon. It is never enough time when you're enjoying someones company! Invest your time for best results.
 

As a Companion, I believe in enjoying every moment we share together. While we are together I am entirely focused on you. I do not even like to have my phone out! The rest of the world can wait. I want to make your every dream and desire a reality. Let me satisfy your cravings. I am tall, athletic, curvy, with an hourglass body. I am a beautiful woman. My classic style is dresses and heels. I am tall in heels, I don't mind if you're short. I call you "boob hight."  As for me uniquely, I am a former college athlete, sorority girl, well-educated twice, and described as bright, charming, and a breath of fresh air. I am the girl in the pictures! That is me! My favorite color is pink, my lucky number is 13, and I have 2 cats and a dog. I am an excellent and gifted conversationalist. I drink champagne by the bottle,  I am a weed connoisseur, I like my oysters Rockerfeller, and I like my steak medium rare plus. I fly first class. I park valet. I sit in VIP. I do not like to wait in lines. If we go to a concert or sports event, I will insist on matching outfits. I live life to the fullest!

 

I offer Personalized Concierge service Companionship, Affection, and Attention. I am confident in my skills, talent, and abilities because I have proven myself over a beautiful 10-year career! I am celebrating 6 years as a Chicago Exclusive! I do not consider myself a touring provider even though I offer Travel Companionship. I am the legendary, the iconic, the infamous, the fabulous, the one & ONLY Heather Riley. There has never been anyone like me - there will never be anyone like me again. I am a rare gem that will not happen twice in a lifetime! From my head to my toes, my personality, my background and lifestyle, my attention to detail and care - The Heather Riley Experience is unmatched and in a league of its own. 
 

I am beautiful, tall, olive skinned, almond eyes, and  wild curly hair. I have the most perfect pair of hand crafted breasts. My waist is 30 inches and my rear is 43 inches! A true hourglass body. I am only getting more perfect and beautiful with age! You can see it with your own eyes. I love laughter and conversation so all you need to do is be yourself.  I enjoy spending my time with you flirting over drinks and planning out our next adventure. You will want to do so many things with me! I am going to encourage and indulge you. It's lovely to see you once, but it's delightful to continue to see each other! I am the Gentleman's Choice Companion. I have dedicated the last 10 years to fulfilling fantasies and long-term ongoing relationships. As both lover and friend, I am a safe space to let loose and a release from the crazy world holding you back and stressing you out. You deserve a woman like me in your life. We can do whatever you like! I am lots of fun, silly, sexual, erotic, impossible to miss, and I'm not  shy. I love to share may wild stories but my jokes are terrible. I love to entertain so nobody could ever call me boring! (Unless they are the boring one. hehe) I love Multi-hour Dates to sporting events, live concerts, musicals and operas, festivals, etc - all highly encouraged! I thrive in longer engagements. I am just a good time girl! Day time dates that include inducing in fine dining, massages, shopping, sight seeing, adventure, night life, unique experiences, traveling - all things I love. I'm as sweet as can be and as kinky as you'll let me! You are in for a treat. Everything you've heard about me? It is true. It's all true. Maybe.

(The rumor about me running 5 minutes late

is usually true! Shh!)
 

While my main focus is in in-person dates, I am also online via OnlyFans every day! If you do not have an account yet, may I strongly encourage you to reconsider? You are missing out on all my best content and gorgeous nudes. Subscribe to unlock 2400+ Pictures and Videos, Private DMs, Exclusive Adult Content, 4-6 Live Shows a week, and a fun interactive menu. I am currently expanding to Fansly. I am a verified model on PornHub. I am at Exxxotica Chicago 8 years in row. You might find me on a couple other spicy sites but I am not active elsewhere at this time. Subscribing to my fan sites is a great way to get to know me more intimately and also support my continued success! I love being a content creator. I'm having a lot of fun being the reason you get aroused. I am proud of my body and I want you to see every inch. I do not have a lot of content posted on social media.

But I am available 24/7/365 with the click of a button. My profile bio lightheartedly describes me as a big tiddie, 240 friendly, tattooed MILF. JACKPOT. 

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If you'd like to hear me talk about my career, you can listen to my podcast episode featured on Full Service Podcast with Tank Smith. It was such a fun interview!

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Lastly, I am a proud Kansas City girl. I live in Chicago but grew up with summers in the Ozarks. I am not a true city girl. I will always love the Chiefs, BBQ, and small town culture! I will always love my hometown.

I had a lot fun growing up. It was great!

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I have lived in Chicago for 6 years and I still do not know my way around. I am GPS dependent! I will always ask for an exact address. I had no idea the suburbs were so large. Now I understand why Chicago has two baseball teams, two airports, and two zoo's! Chicago is just a huge area! No matter where you are, I'm probably an hour away. And there's a good chance I'll be 5 minutes late. That is just life in Chicago for ya.

I guess I'm not in Kansas anymore!

 

Now that you know a little bit about me, I would like to learn a little bit about you! Email or text me to schedule your first date. Tell me a couple of fun facts about you! Reach out to introduce yourself or to reconnect with me. I would love to see you! If I don't respond, it's because I have lots of things to do and sometimes things get lost! I do not have an assistant so feel free to send me a quick text to return to your inquiry. That usually does the trick. CashApp notifications always get my attention if I'm busy running around.

            Looking forward to hearing from you!

 

                                      Heather Riley            

"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