Holly Winter


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  • Location


  • Age


  • Phone SMS Only

    0421 646 559

  • Height

    178 cm

  • Dress size


  • Hair


  • Eyes


  • Place of Service

    incall, outcall

  • Body Type


  • E-Mail



Currently no tours planned. Subscribe to receive updates when Holly Winter plans a tour to your city

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 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 D cup that compliments her toned athletic frame.

Whether you need a plus one to an event or intimate dinner date, to unwind and de-stress over hotel drinks, a relaxing and sensual hotel massage or a full out fun and frisky good time by yourself, your friend, your partner... Holly will bring the VIP experience to you. 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.
Additional Hours $ 400 Additional GFE time per-hour
Social date $ 450 Hello Holly (3hr. Companion Only)
4 Hours $ 1800 Hello Holly GFE
Overnight $ 3400 Little Hollyday
Duos with another escort $ 2500 2hr MF Duo (MMF/FFM/MFMF/Voyeur)
IPT $ 750 2hr Intimate Personal Training
Couples $ 1000 3 Kissing Under the Mistletoe (1.5hr)
VIP Hosting $ 150 Minimum 2 hours. Lingerie, French Maid, Bavarian or Grid Girl waitressing.
"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 - $600/hr of GFE Extend at $400/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 +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.
* Extend at $150/hr

"Hello Holly GFE" Wine and Dine + "Dessert" - Min 4 hour booking, $1800
* 2 hours 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.

"Little Hollyday" - Overnight* - $3400
* Up to 12 hours included, concluding no later than 8am the next morning
* Want to take a truly elegant lady 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


"When I think about you I touch my 'elf". - Skype sessions can be performed for $60/30mins.

COUPLES: Holly loves to entertain couples at any described rates above. Minimum 1.5 hour booking as above and then $500ph thereafter.

Dynamic Duo: Holly has male and female partners for anyone wanting to explore Voyeur, MMF, FFM or MFMF fantasies. Both Singles (men & ladies) or couples are welcome but all Dynamic Duo bookings are a minimum of 2 hours. Duo bookings at $1500 for the 1st hour and $1000 per hour thereafter (for the duo, not "each").

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 $200.

VIP Hosting: Holly, and friend/s, make great flirty hosts for your poker, footy, motorsport, whiskey/wine appreciation night. Sexual services are not included but can be negotiated.


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. Note Lingerie Waitressing is just that - any additional services are not included, ask for options around that when booking to avoid disappointment.


Absolutely no unprotected sex.

All PSE activities, especially Greek, Natural Oral, CIM, MFM & Heavy BDSM - Solely at my discretion, for additional $500.

Fly-Me-To-You - the travel and accomodation expense etc is NOT inclusive in the rate. A deposit sufficient to cover flights and transfers that I book + 20% of the service fee is required for FMTY. FMTY is outcall only and minimum overnight booking.

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.

WHEN ENQUIRING/BOOKING: Please advise who you are, when you would like to meet and what service/s entice you.

COVID-19: All reasonable precautions are made. Please postpone your booking if you have any flu like symptoms or if you have been to a flagged outbreak area within 14 days of your appointment. If I cancel or I am already on-tour, all deposits will be refunded in-full, immediately. Otherwise, deposits can be held over to a postponed time.


  • 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
  • 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
  • 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
  • Strap on - on me
  • Strap on - on you
  • 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 - in-person or via WebCam)

VIP Event or Party Host - Holly is available to host private functions, including with friends! RSA qualification.

When can we meet?

Weekday From Until
Wednesday Please contact for time Please contact for time
Thursday Please contact for time Please contact for time
Friday Please contact for time Please contact for time
Saturday 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 or overnight bookings other than on-tour, please allow at LEAST 1 week notice to avoid disappointment.
When I am not on a Tour, I love to do Fly-Me-To-You bookings in Australia or overseas.
Note, overseas tours and FMTY bookings are VERY limited due to COVID Travel restrictions.


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 (32D top, S bottom)

  • spa / massage

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

  • shoes

    Louboutin, Manolo Blahnik and Jimmy Choo, Balenciaga, LV where to stop...

  • vouchers

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

  • country


  • wine

    Pinot Noir

  • designer

    All things Italian and French plus Morrisey, Sass & Bide, Camilla & Marc, Christian Louboutin

  • relaxation

    Anything by, in or on the water

  • car

    Mercedes AMG 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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