Olivia Winsome


Note: You are currently viewing in discreet mode no images will be visible. Click here to turn discreet mode off

Profile SWA 11660XE

  • Location


  • Age


  • Phone SMS Only

    0498 839 634

  • Height

    172 cm

  • Dress size


  • Hair


  • Eyes


  • Place of Service


  • Body Type


  • E-Mail


About me

Intelligence, warmth and style...
.. the discerning gentleman’s perfect companion.

A true gentleman knows the value of a classic lady.

When we meet, you’ll immediately see what sets me apart. My poise and intelligence position me as an exceptional companion – someone you yearn to have by your side, in public and private.

I am slim and toned, with long legs, and natural E-cup cleavage that commands attention. My long, chestnut-brown hair frames my delicate features. And as our connection deepens, you may notice my green eyes intensify, sparkling with warmth.

I have previously had careers in the Australian wine industry and the corporate world, and have travelled extensively both for work and pleasure. As a result, I have extensive knowledge of and appreciation for food, wine, fashion and culture. I take great pleasure in spending time with those who have similar interests to me.

Whatever adventures we embark on together, you’ll be happy to have me by your side.
I love indulging in life’s pleasures: from theatre and ballet to fine dining. But I also enjoy simple, sweet, carefree experiences, and I’ll certainly never say no to a relaxing beach holiday where we can feel the sand between our toes and drink cocktails watching the sunset.

One of my favourite ways to spend the weekend is to escape the city and take a trip to the country to visit wineries and relax by an open fire. Often in life, we fall into a routine, and all of a sudden, we realise life has been passing us by. Getting away from it all means we can slow down, appreciate one another and really connect. And, I have to say, there’s something incredibly romantic getting to know each other in the idyllic setting of a vineyard over wine tastings, charcuterie and long conversations. When we’re finally alone, I’ll show you the side of me reserved only for selected lovers: cheeky, playful, and passionate - a woman who never holds back.

Although I am based in Melbourne, I adore travel. If you’re seeking an all-inclusive travel companion within Australia or New Zealand, I would love to join you on your next business trip. There’s nothing quite as relaxing as being met at the door with a glass of wine and a beautiful lady clad in lingerie after a long day of meetings. If this sparks your interest (and your desire), you can view my Fly Me To You packages at oliviawinsome.com/fly-me-to-you

If you’ve been dreaming of a secluded escape, whether for an evening or a weekend, I would love to hear from you. I urge you to visit my website to learn more and start planning our date – oliviawinsome.com



2 Hours $ 1100 GFE
4 Hours $ 1700 Lets take our time getting to know one another over dinner or lunch prior to play..
6 Hours $ 2200 This is my preferred booking, it really gives us the time to connect and create special memories.
12 Hours $ 3500 Wake up next to me. *I will require a min of 6 hours sleep
1 Hour $ 650 Currently Unavailable


Due to state legislation, I am unable to provide details of my services. Please contact me for information.

When can we meet?

Weekday From Until
Monday Please contact for time Please contact for time
Tuesday Please contact for time Please contact for time
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
Sunday Please contact for time Please contact for time
  • Available by appointment
  • Flexible hours by appointment
I am currently on hiatus due to COVID-19. I’m enjoying relaxing at home, but I can’t wait to be back enjoying romantic dinners and tête-à-têtes between the sheets. I’ll be letting my patron’s mailing list know when I start accepting date requests again (hopefully it’s not too far away!) You can sign up for my exclusive patron’s list by visiting oliviawinsome.com/patrons (I don’t want to ruin the surprise, but let’s just say you’ll receive a few risqué images upon sign-up…) My mailing is also the only place I ever advertise promotions – never say I don’t spoil you!

I am available by advance appointment only and am flexible with meeting times for the right gentleman. 24 notice is preferred where possible.

I happily accept invitations for prolonged engagements such as dinner dates, sleepovers, weekends away and more extended travel requests. Please view my website for more information on my all-inclusive Fly-Me-To-You packages – oliviawinsome.com/fly-me-to-you

A 10% deposit demonstrates your commitment to our meeting (*50% for FMTY dates). The deposit can be paid with a discreet online gift card of my choice, via bank deposit or Beem It. When we meet, you can pay the remainder of the fee with cash, debit or credit card. Credit card payments incur a 2% surcharge.

If you are interested in embarking on an adventure with me, please make contact via email or text message (email preferred for initial contact when possible).

To ensure a fast response, please provide your name and mobile number in your enquiry, along with appropriate date details (e.g., time, length, location, etc). I will do my very best to get back to you within 24 hours (provided your enquiry is sincere and polite).

I recognise that time is a precious resource (we’re certainly not getting any younger!), so I am selective about who I spend my time with and am flattered when others choose to spend theirs with me. I want to ensure we both genuinely enjoy ourselves. The more information you provide about your needs and desires, the more easily I can ascertain whether we are right for one another. Additionally, my mind and body are very important to me - I keep myself in great shape and immaculately groomed for you! For this reason, I prefer spending time with those who similarly value personal hygiene. (Bonus points if you also love food, wine or travel…)


Currently no tours planned. Subscribe to receive updates when Olivia Winsome plans a tour to your city


Preferred Contact Method

For bookings or enquires please email or text only.
Email is always preferred in the first instance and is monitored more frequently than text. I will do my very best to get back to you within 24 hours, that is of course if you have made a sincere, polite enquiry.

I am well-travelled, with a keen interest in cooking and fine dining, wine and theatre.
  • lingerie

    Dickory Dock, Simone Perele, Honey Birdette

  • flowers

    All of them, I adore receiving fresh flowers... call me old fashioned ;)

  • handbags

    Coach, Marc Jacobs

  • chocolate

    Anything dark will make me a happy woman

  • perfume

    I am allergic to most female perfumes, for this reason I never wear any perfume.

Gifts are not expected but very much so appreciated. I have a more specific list linked via my website if you need more inspiration. xx
  • wine

    Champagne, Margaret River Chardonnay & Cabernet, Claire Vally Riesling, Tasmanian Pinot Noir...

  • relaxation

    That first stretch first thing in the morning... especially when you don't have to get out of bed..

  • restaurant

    I adore all food and love to explore new restaurants..

My Escort Diary


View Testimonials
Write a Testimonial

Note: You are currently viewing in discreet mode to leave a testimonial please turn off discreet mode.
Click here to turn discreet mode off

Write a testimonial

Please ensure you have not written a name that you do not wish to be publicly visible.
PLEASE NOTE: We do not publish testimonials that are submitted by advertisers. Testimonials must be submitted by clients only.


Save Olivia Winsome as your favourite escort
By clicking “AGREE AND ENTER” below, you confirm that you are over the age of 18 years and have read, understood and accept the Terms and Conditions for use of this website. Please click here to read the Terms and Conditions.