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Anna Simone | VIP Companion
Sensual Luxury Experiences with Miss Simone

Boston & Woburn Packages

Welcome to the world of Miss Simone — your exclusive, upscale escape in the heart of Boston and Western Massachusetts.

Whether you’re seeking a luxurious GFE companion, a deeply connected milking table experience, or a tantalizing body-to-body massage, I invite you to step into a world where your deepest desires are indulged in a discreet and unforgettable setting.

As a Caribbean-born, Boston-based luxury provider, I specialize in sensual experiences for discerning gentlemen of all backgrounds. I understand that true connection and curated intimacy take time — which is why my sessions are designed for quality, not speed.

💡 Note: I am not the “fast food” version of companionship. I’m the full-course, candlelit indulgence — and I’m here for those who appreciate the difference.

📍 My Incall Locations

Boston – Back Bay: Elegant and centrally located for discerning professionals
(Tue, Thurs & Sat | 9 AM – 12 AM)

Burlington/Woburn – Western MA: Spacious, discreet, and equipped for full milking table and nuru massage experiences
(Mon, Wed & Fri | 8 AM – 11 PM)
Bonus: Free parking available for large trucks and work vans.

🌅 Early Morning Appointments (8–11 AM) must be booked the night before.

✨ Booking Expectations

New clients must book 12–24 hours in advance to ensure availability.

Same-day sessions may be possible for established clients — text or message directly for consideration.

I do not offer 30-minute sessions. Every encounter is thoughtfully prepared and unrushed.

💳 Deposit & Payment Options

To confirm your booking, a deposit is required. Multiple discreet and secure payment methods are available:

Accepted Deposit Methods:
– Zelle
– Apple Pay
– PayPal
– Venmo
– Cash App
– Bitcoin
– Credit/Debit Card via online invoice (+10% transaction fee)

Upload Gift Card Here


GFE, PSE & GREEK  PACKAGES
  • 1 Hour GFE Treat $1000
  • 1 Hour Greek & GFE Bliss $1,200
  • 1 Hr PSE Tryst $1300
  • 1.5 Hr GFE Intro $1,300
  • 1.5 Hr Greek/Anal Delight  $1,500
  • 1.5 Hr PSE Tryst $1600
  • 2 Hr Pure GFE $1600
  • 2.5 Hr GFE $1,900
  • 2 Hr Greek Adventure $2000
  • 2 Hr Ultimate GFE & PSE Deluxe  $2100
  • 3 Hr GFE Delight $2100
  • 3 Hr GFE & PSE Deluxe $3000
  • 4 Hr Dinner + Milking Table & GFE ( Inquire )
  • 6 Hr Adventure (Inquire)
  • 12 Hr Overnight GFE Deluxe
  • 24 Hr Wild Boston Tryst (Inquire)
BODY2BODY ,NURU & GFE COMBINATION PACKAGES
  • 1 Hr GFE & Body2body  $1100 *(90 Min $1400(*2 Hr $1600
  • 1 Hr GFE + Milk-Table $1,200
  • 1 Hr GFE + Wet & Wild Nuru Bliss $1,200
  • 1.5 Hr Milk-Table & GFE Bliss $1,600(*2 Hr $1,800)Fav
  • 1.5 Hr GFE & Nuru Bliss $1500(Vip Nuru +$100
  • 1.5 Hr Body2Body + Milking Table $1300(2 Hr $1500)
  • 1.5 Hr Greek/Milking Table Combo $1700
  • 1.5 Hr PSE Milking Table Combo $1800 (2 Hr $2300)
  • 2 Hour GFE & Nuru $1900 (+ Greek + 400/PSE $500)
  • 2 Hr Milking Table/GFE & Nuru Combo $2,200(2.5 Hr $2400(3 Hr $2,700
  • 2.5 Hr Milk-Table + GFE $2,100
  • 3 Hr Greek + Nuru & Milking Table $3400
  • 3 Hr Fetish /Nuru & Milking Table $3500
 

Are You Over 18 Years of Age?

DISCLAIMER: Access is made available only to those who accept the terms of the following agreement. I do not find sexual or adult oriented material to be offensive or objectionable. I am at least 18 years of age and have the legal right to possess adult material in my community. I understand the laws and standards set in my community, site and computer to which I am transporting this material, and am solely responsible for my own actions. Under penalty of perjury, I solemnly affirm that I am over the age of 18 and that I am not accessing AnnaSimone.com for the purpose of obtaining information that will be used by others or me in any capacity against the Webmaster of this site, its owners, employees or any other parties associated with AnnaSimone.com. You understand that this site contains material that may be considered objectionable. You are not prohibited by law to view adult content in your area, and that adult language and nudity are not offensive to you. You agree to enter this site for your own personal entertainment only. You are not a U.S. Postal official or law enforcement agent or acting as an agent thereof, attempting to obtain any evidence for the prosecution of any individual, BUSINESS, advertiser, or for the purpose of entrapment. You are not from a government agency or organization here to obtain any information to use against the site operator, advertiser, or any person whomsoever in ANY CONCEIVABLE MANNER. You will not pass any information contained herein to minors or to those that do not wish to view this site. You will not attempt to bypass any security on this site. You understand that this site and all of its photos are protected under U.S. and International copyright laws. Reproduction, alterations, or reposting of any image is strictly prohibited without prior consent. You understand that book marking to a page on this server/site whereby this warning page is by-passed shall constitute an implicit acceptance of the foregoing terms herein set forth. You believe, that as an adult, you have the unalienable right to read and/or view any type of material that you choose. You can stop receiving such material at any time by logging off and not returning. You are viewing this material for your own personal use and it isn’t to be viewed by minors or anyone else but yourself. That at no time, will minors be subjected to said material of any kind.

* Please be aware that for legal reasons the discussion of Rates and exchange of money is for the time spent together. The discussion of sex in any context and at any time, regardless of its intended purpose in asking, will be discussed strictly from personal preferences and NOT in any type of context that might be construed as in exchange for money. Even if implicitly described as such by you, anyone, or anything.