Heather Riley's Fall 2025 Schedule

Aug 28
3 min read

OHHHHHH LOVER BOYS! Your favorite girlfriend is here with exciting news:

Here is My Current Fall 2025 General Schedule for the REST of the Year!

NYE Exclusive Date Night is First to Claim with Deposit

Does this view look familiar? The Perfect Mix of GFE + PSE

Prebooking in Advanced is Strongly Encouraged, Same Day Requests as Allowed

School's Back in Session and so is my Weekly Incall!

Incall Located in the West Suburbs Monday - Friday 8am-2pm

please prebook the weekly incall as early as possible, but no later than by the night before

if i dont know to expect you, i may make other plans when i would have gladly seen you instead

Booking Dates for: August - December 2025 MY FAVORITE TIME OF THE YEAR Its the most incredible city to fall in love. Lets share an incredible romance. Take me out for cider and then take me to your bed...

Travel Companionship Dates for Winter 2025/26 - Romance is not limited by geography; real passion is intensified and heightened as we bond over a shared intimate escape where we can be freely and genuinely ourselves.

Chicago Area: 2 Hour Minimum for New Clients, longer dates prioritized

Currently Accepting New Clients and Reconnections with Familiar Faces

FMTY Dates: 24 Hour Minimum, no maximum, allowed for first dates, plan ahead or spur of the moment, passport ready, excellent traveling sidekick for boring business trips or unplug and sneak away for the weekend.

FUN FACT: I see male clients, but I am also couple-friendly and female-friendly. I absolutely love couples! And women are always encouraged to book a female experience with me. As a gentle reminder, I am also Disability-Friendly and Group Sex Friendly. I am considering offering a 2026 Gangbang - you know how much I love to play and show off! Forever 420 Friendly :)

Outcalls and Travel Companionship available anytime, anywhere for any reason. I'm the type of gal you like to have around. Even just being with her is good for the soul and inspires the heart. Time with Heather is always Time Well Spent. (and over too soon!) and I am such a slut for new Michelin Stars or Champagne with Oysters!

My regulars know how easy it is to book with me and they know I'm the type of person to abandon all my plans and rearrange my entire day just to accommodate a sweet respectful request. I take my job as your girlfriend VERY seriously. My men are exceptionally well taken care of. It is my privilege to be your girl for as long as you'll have me by your side.

Want to do SOMETHING but can't think of what? Its fine: I'm a professional.

Need help making an itinerary? No ideas or too many ideas? Maybe we need to plan a series of dates to achieve the perfect mega date that you always wanted to do?

I've got you covered! I can plan the perfect trip from Staycations to Dream Vacations, I'll take care of the details and all you have to do is enjoy yourself. Let me show you how beautiful life can be with a little magic and inspiration applied. You work hard enough, let me take it from here.

In the next couple of days, I'll post a list of fun fall date activities for us to enjoy or be inspired by in Chicago. I'm awesome like that.

As Always, I'm a Full-Time Dedicated Companion so I'm always available for:

Social Day Dates, Lunch/Dinner Dates, theatre dates, opera dates, festivals,

work functions, galas, auctions, social events, as well as Overnights, 24H Min FMTY,

Sponsored Tours, and the impulsive same-day afternoon romp! Anytime of day - give me a call and I'll get you your Heather fix. I'm enthusiastically yours, if you think of me, message me darling.

Contact Me Boyfriend! I miss your crazy ass. I know you miss me, too.

Email (Heather@HeatherRileyXO.com) or Text (816-456-3688) to plan a first, secdond, or 50th date with the sophisticated, charming, and darling Heather Riley in Chicago or Anywhere You Are! Fall in love this Autumn with a wonderful warmhearted girl dedicated to your happiness.