Holly Winter


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Currently touring in Sydney

  • Location


  • Age


  • Phone SMS Only

    0421 646 559

  • Height

    178 cm

  • Dress size


  • Hair


  • Eyes


  • Place of Service


  • Body Type


  • E-Mail



Australian Tours

To From Until
Sydney 16th January 19th January
Bowral 23rd January 24th January
Sydney 6th February 9th February
Bowral 27th February 28th February
Sydney 5th March 8th March
Holly Winter - Private Escort Sydney

About me

Country charm seeks city thrills
Holly catches the eye of both men and ladies of distinction, who appreciate beauty and have an eye for all round class.

Holly is based in peaceful country NSW but regularly enjoys visiting the lights of the big city where she likes to ramp up the energy. She is well spoken, well travelled and well educated with 2 undergraduate degrees and a masters degree.

Her cheeky, mischievous energy is infectious and sure to enthral you and capture your attention while her positive and refreshingly open demeanour will garner your admiration and respect.

It also needs to be said...Holly is a complete knockout. 5 foot 10inches, size 8, lithe athletic figure, gorgeous legs and a peachy bottom. She is super-fit, very-fun and always-ready to play! Holly is of Australian/European heritage, chocolate brown hair and mesmerising blue eyes. Since her profile photos, Holly has upgraded to a perky sensual C cup that compliments her toned athletic frame.

Whether you need a plus one to an event, an intimate dinner date and conversation, to unwind and de-stress over hotel drinks, a relaxing and sensual hotel massage or a full out fun and frisky good time- Holly can do it all. I love dichotomy in life; black to white, Jekyll to Hyde, sugar to spice. So whilst I can be the most elegant lady in the room, get me alone and I will bring your naughtiest dreams to life.

Kind yet fierce, elegant yet naughty, physical yet submissive, country and city...Holly is your the perfect match to any need or desire you may have.



1 Hour $ 600 Cheeky kiss under the mistletoe.
4 Hours $ 700 Hello Holly
4 Hours $ 1800 Hello Holly GFE
Overnight $ 3400 Little Hollyday
Duos with another escort $ 2500 MF Duo (MMF/FFM/MFMF/Voyeur)
IPT $ 750 Intimate Personal Training (2hours)
Couples $ 1500 3 Kissing Under the Mistletoe
"Cheeky Kiss under the MistleToe" - Christmas is 365 days a year with Holly. Whilst you can never have too much Holly, you can have the gift of just 1 cheeky hour of her time - good things can come in small packages... $600/hr of GFE Extend at $450/hr.

"Hello Holly" - Wine and Dine Only - minimum 4 hours, $700.

Are you looking for just a date or a Plus1 for a work event but aren't needing much more than a sweet kiss farewell at the end of the night? You can have Holly partner you for 4 hours of wine & dine, corporate event +1, social outing or just exquisite 1-on-1 quality company. With three university degrees, Holly can hold an intellectual conversation over a formal dinner or regale funny stories at a chilled out casual affair.

Need a beard for a family event to keep Grandma Doris off your back? Let Holly put on the charm offensive for you and resolve the end of day family-event-anxiety with a shoulder massage.

Extend at $150/hr

"Hello Holly GFE" Wine and Dine + GFE - Min 4 hour booking, $1800

2hours date and 2 hours "dessert" - Holly is quite the food and wine aficionado with many friends in the restaurant and wine-making world. Would you like Holly to take charge of the wine selection only to hand over the "in-charge" baton on return to the hotel? Maybe you'd like to take Holly to a special event or just a 1-on-1 dinner knowing someone so alluring is coming back to your hotel room for an intimate night-cap.

Have you always wanted to take that hot gym-bunny from the hotel gym back to your room for a post-workout "warm-down"? Sure! See IPT below too.

Fancy a proper "hands-on" tour around Sydney? Holly is equally up for being a tour-guide in her favourite city or take this country girl to your favourite harbourside spots for a cuddle with a water view and explore the hedonistic delights of Sydney together.

Extend at +$450/hr

Little Hollyday - Overnight* - $3400

Up to 12 hours included, concluding no later than 8am the next morning

Want to take Holly out for a huge night on the town knowing you'll not be able to get back out of bed once you get back to the hotel? Be sent off for sweet dreams by Holly only to get some help to "get-up" and at em in the morning.

*6 hours actual sleep minimum

Extensions to an overnighter can be made based on any package above or simply that "1 more hour" at $150/hr for a sexy friend, $450/hr for a sexy friend-with-benefits. Multi-day or travel bookings considered on request.


"When I think about you I touch my elf". - Regular or one-off Skype sessions can be performed for $60/30mins, (no fee for booking co-ordinations). Very limited availability.

COUPLES: Holly loves to entertain couples at any described rates above + $500 only. Minimum 2 hour booking to really get the most out of it for everybody.

MF DUO: Holly also has a Male Escort partner for anyone wanting to explore Voyeur, MMF, FFM or MFMF fantasies. Both Singles (men & ladies) or couples are welcome but all couples/MFMF bookings are a minimum of 2 hours. MF Duo bookings at $1500 for the 1st hour and $1000 per hour thereafter (for the duo, not "each"). A more PSE experience, whether just watching the Duo together or partaking is an extra $500.

INTIMATE PERSONAL TRAINING - Holly used to be a pro-athlete - what could be hotter than hitting the gym together for a workout, knowing that hot gym-bunny you're checking out is coming back to the hotel room? Up to 1hr gym and 1hr in the hotel. This can be a couples session too for an extra $250, or I can bring another ex-athlete male escort to the workout for an additional $800.


All bookings incur an Uber fare to you when travelling more than 20mins from Sydney CBD.

Disabilities are welcomed by Holly - Just let her know in advance, especially if there's any specific logistical or medical assistance you require.

If you'd like a bit of variation to any of the above packages or you have any special requests (especially special event clothing like Black Tie or themed events), please just ask in advance.


Absolutely no unprotected sex.

Greek, BDSM and all PSE - Solely at my discretion, for additional $500

Credit Card payments incur a 1% surcharge.

All bookings will require a 20% deposit, only refunded on cancellations more than 48 hours in advance. If you need to postpone, I will consider holding the deposit over to the revised booking - I travel 4 hours each way to Sydney so please be considerate if you need to change plans!

When contacting for a booking: Please advise who you are, when you would like to meet and for what service/s.


  • Affectionate cuddling
  • Affectionate kissing
  • Anal play
  • BBBJ – bare back blow job
  • BDSM
  • BJ – blow job
  • BLS – balls licking and sucking
  • BS - body slide
  • Bi twin (double)
  • Brazilian
  • CBJ – covered blow job
  • CIM – cum in mouth
  • CIMWS – cum in mouth with swallow
  • COB – cum on body
  • COF – cum on face
  • Costumes
  • Costumes and role play
  • Couples
  • DATY – oral on me
  • DDP – double digit penetration
  • DFK – deep French kissing
  • DP – double penetration
  • DT – deep throat
  • Dinner companion
  • Dirty talk
  • Disabled Clients
  • Doggy style
  • Erotic sensual massage
  • FK – French kissing
  • FS – full service
  • Facial - cum on face
  • Filming
  • Fire and ice – hot and cold BJ
  • Fly Me To You
  • Full oil massage
  • GFE - girlfriend experience
  • Gagging
  • Greek – anal sex
  • HJ – hand job
  • Happy ending
  • Italian
  • Kissing
  • LK – light kissing
  • Lesbian / Bisexual (Female To Female)
  • Light bondage
  • Light spanking
  • MFF – male female female
  • MILF – mother I’d like to F
  • MMF - male male female
  • MSOG – multiple shots on goal
  • Maid
  • Massage
  • Masturbation
  • Multiple positions
  • Mutual French (oral)
  • Mutual masturbation
  • Mutual natural oral
  • Natural oral
  • Nurse
  • Overnight stays
  • PSE – porn star experience
  • Passionate kissing
  • Pearl Necklace
  • Photography
  • Role play
  • School girl
  • Secretary
  • Sex toys
  • Sexy lingerie
  • Sexy shower for 2
  • Snowballing
  • Social escort
  • Spanish
  • Spanking - On me
  • Spanking - On you
  • Strap on
  • Strip tease
  • Tea bagging
  • Travel Companion
M/F or F/F Duo, booking available
Voyeur booking available (Solo or couples to watch me with a duo partner - live or via WebCam)

When can we meet?

Weekday From Until
Thursday 10:00 am 12:00 am
Friday 07:00 am 02:00 am
Saturday 07:00 am 12:00 pm
Sunday Please contact for time Please contact for time
  • Available by appointment
  • Pre bookings preferred, but can be available at short notice
  • Flexible hours by appointment
  • Please contact me for my availability
For Fly-Me-To-You bookings, please allow at LEAST 1 week notice. Sydney/Blue Mountains, Melbourne, Brisbane, Canberra and Country NSW, I "might" be able to accomodate less than 1 week's notice.
When I am not on a Tour, I love to do Fly-Me-To-You bookings in Australia or overseas, especially if there's a little notice.


Preferred Contact Method

Please provide booking name, time, duration and any special requests.

I am fit and active...try to keep up with me if you can! I like to get outdoors, get the blood pumping and have a playful time.
I have two undergraduate degrees, a post graduate certificate and a masters degree. I am well travelled, well spoken and can dress for any occasion.
I am well read and I am across current affairs.
I am a sexual creature and love to develop chemistry to build a strong sexual tension. Possibly because I am so in control of my daily life, I love to be submissive in a sexual context, but am equally comfortable taking the lead if you prefer.
  • lingerie

    Honey Birdette and IM Imports

  • spa / massage

    Who doesn't like being pampered! (Sydney venues are great)

  • shoes

    Louboutins and Jimmy Choos

  • vouchers

    David Jones - I love the old-school feel of DJ's in Sydney

  • country


  • wine

    Pinot Noir

  • designer

    Jimmy Choo

  • relaxation

    Anything by, in or on the water

  • car

    Mercedes SLS

  • smell

    Cookies, any baked goods really - my diet nemesis!


View Testimonials
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  1. BY Il Dottore

    I had the pleasure of taking Holly out for one of her dinner dates. Firstly, I’ll be booking again. Amazing. She is every bit as conversational as she is beautiful. She was impeccably presented and there was no suggestion she was anyone other than my girlfriend for the night (I’ve had bad experience...

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