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Heather Riley,

The Gentleman's Choice.


Hello, Naughty Friends.

I'm Heather Riley,  the Gentleman's Choice Companion & Upscale Escort Based in Chicago, Passport Ready Travel Companion
GFE, PSE, BDSM, Kink/Fetish, Couple Friendly

Dinner Dates & Overnights

 As a Companion, I am  based in Chicago. I am a former college athlete, well-educated, and described as bright and playful. I enjoy spending my days holding hands and sneaking kisses. 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. 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

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

Will sign NDA

for discerning clients.


I'm a sweet, kind, passionate lover. Highly intelligent, delightfully playful, sinfully incorrigible. I love taking time to find out how much we have in common while we slow dance after dinner.


Desire, intimacy, falling in love over and over again, late nights, dinner dates, social dates, hand in hand, sharing secrets, making new secrets, naughty pictures,

"I Miss You..." texts...


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

Sugar Baby-Sugar Daddy available for those genuinely interested or experienced in the lifestyle. Short-Term or Long-Term. Email me now for base terms.


I enjoy spending time with respectful gentlemen in all your forms. I do not care about age, race, weight, religion, etc. I do expect kindness, communication, honesty, and respect.


Must Verify.

Deposits preferred.

Cancellation fees speak highly of you.


Suitors may now submit tasteful reviews of our time together.

P411 - Okays




Thank you! 


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