Holly Winter

Country charm meets city sophistication

Holly catches the eye of men of class, who appreciate beauty and have an eye for all round quality. 

Holly is based in peaceful country NSW but regularly enjoys visiting the lights of the big city where she grew up. 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 fit, fun and ready to play!  Holly is of Australian /European heritage, has brown hair and mesmerising blue eyes. 

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. 

Kind yet fierce, sensibly yet naughty, fun yet mischievous, country and city...Holly is your the perfect match to any need or desire you may have.

Location: Bowral , NSW

My Stats

Age 30s

Height 178cm

Eyes Blue

Hair Brown

Body Type Athletic and lithe

Ethnicity Australian

Please contact me and I will happily discuss my list of services to you. Good etiquette is essential, please be polite and well mannered.


  • FFM Doubles
  • Ball Licking
  • Straight
  • Sexting
  • Skype
  • Videos
  • Webcam
  • Light Bondage
  • Anal Play on Me
  • Light Anal Play
  • Finger in Pussy
  • Mutual Oral
  • Deep Throat
  • Cum on Body COB
  • Cum on Face
  • Cum with Swallow
  • Cum in Mouth CIM
  • Bareback Blowjob BBBJ
  • Covered Blowjob CBJ
  • Nipple Sucking on Me
  • Nipple Sucking on You
  • Manual Masturbation
  • Italian Sliding
  • Spanish
  • Multiple Shots on Goal MSOG
  • Handjob
  • Role Play
  • Costumes
  • Disabled Clients
  • Female Clients
  • Couples
  • Striptease
  • Sexual Intercourse
  • Passionate Kissing
  • Deep French Kissing
  • Light Kissing
  • Oil Massage
  • Cuddling
  • Erotic Massage
  • Spooning
  • Body Slide
  • Webcam
  • Skype
  • Sex Toys
  • Dirty Talk
  • Digital Penetration
  • Oral on Me
  • Companionship Only
  • Blowjob BJ
  • Spanking
  • MMF Doubles
  • Anal Sex
  • Snowballing
  • Bisexual
  • BDSM
  • Strap On

Advance bookings are recommended to avoid disappointment, please check my availability below.


Standard Services

Cheeky Kiss Under The Mistletoe
Hello Holly
Hello Holly - GFE
Little Hollyday
MF Escort Duo (MMF/FFM/MFMF)
Intimate Personal Training
3 Kissing Under the Mistletoe

Additional Rates

"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 does entertain couples herself 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 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 $200, 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 perfectly OK with 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 & PSE - Solely at my discretion, for additional $500

BBBJ, CIM/CIMWS, Heavier-BDSM and Kink Requests - Only considered for repeat customers on multi-hour bookings and solely at my discretion + PSE Fee.

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 and when you would like to meet for what service. 

Available Angels has not conducted an interview with Holly Winter yet but watch this space

Reviews of Holly Winter


Holly Winter was simply amazing. On arrival, the first thing you noticed is those blue eyes and model looks, as she turns to draw you into your room, that bum makes your eyes pop. Holly immediately put me at ease and made me feel like we’d met before I was so comfortable in her company despite her beauty. She looked exactly like her photos.

We shared a kiss and a couple of glasses of champagne together and had an amazing conversation - I did not expect my “date” to be so well educated and travelled and it was literally like having a 1st date with a future girlfriend. Holly really does nail the whole GFE thing.

It’s not hard to become aroused by Holly thanks to her looks, and those abs - wow!… but the sex was amazing. She read me really well, some smoking hot sub-moves that really fired me up and rode me like I imagine only a country girl can. My only regret was only booking 1 hour and despite extending it an extra hour, I just wanted to stay wrapped up in her delicious body. I’ll definitely be looking to take her up on a dinner date or away for a weekend.

Holly Winter has not published any blogs yet but watch this space