Olivia Winsome


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Profile SWA 11660XE

  • Location


  • Age


  • Phone SMS Only

    0498 839 634

  • Height

    172 cm

  • Dress size


  • Hair


  • Eyes


  • Place of Service

    incall, outcall

  • 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


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


Please contact me for my services.

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


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  1. BY Mr M

    From the minute I met Olivia for the first time I felt like we had known each other for many years. Olivia was classy, elegant and every bit the lady I had expected her to be from our communications before meeting. Right throughout dinner to our intimate time together It was an absolute delight to...
  2. BY Richard

    On August the 25th I met Olivia Winsome and what a fabulous night we had. I had arranged a six hour meeting so we could get to know each, have an enchanting dinner together and then more fun in the bedroom afterwards. I have truthfully been reluctant to send in a testimonial as I selfishly don’t wan...
  3. BY James

    A Double Date with Olivia and Alannah I have seen Miss Olivia Winsome several times now; however this was to be the most fun yet. Her friend Miss Alannah Dove, whom I have followed for about a year now was to join us. It was a great pleasure to finally meet Alannah. Both these ladies are far more...
  4. BY James

    It was a hot and steamy Saturday when I most recently met Miss Olivia Winsome for lunch. We dined inside to avoid the worst of Sydney’s sultry heat. After a couple of hour’s great conversation we retired to her hotel. A cool southerly change and the air-conditioning working flat out made for a ver...
  5. BY Mark

    Yesterday I had the pleasure of another “date” with the gorgeous Olivia. Olivia reminded me that yesterday was our 5th date - and let me tell each and every meeting has been special !!! I have seen a number of girls from Scarlet Blue in the past, but none compare with the wonderful Miss Winsom...
  6. BY Mr Lucky

    It has taken me a long time to write this review and I can honestly say I don’t know why. I had been following both Alannah Dove and Olivia Winsome on Twitter for a while and could not decide on which one of these lovely ladies I should see when one day a tweet went up that we’re doing a double so i...
  7. BY Mr Impulsive

    Needing to be in Melbourne for a full day of business meetings recently it was with surprise I noted a few days prior to leaving Sydney that my schedule included plans to meet colleagues flying in from Sydney mid-evening for dinner. With this I realised that it meant I fortunately had a brief window...
  8. BY James

    From the first sight of Olivia’s’ profile on Scarlet Blue, this was a lady I knew I wanted to meet. Only problem was Olivia is Melbourne based and I was in Sydney with no excuse for a Melbourne trip. The solution came with the announcement of Olivia’s first Sydney Tour. Contacting her via email was...
  9. BY Sydney Lover

    Olivia is a rare gem. Your first introduction to Olivia may be through twitter/scarlet blue. Her photos are stunning, her precise is engaging, her Twitter gives you insights to her. The reality far exceeds the advertising. The booking process is easy. Olivia is very responsive to email & sms....
  10. BY Sean

    I had the immense pleasure of meeting Olivia for the first time yesterday. She is simply stunning! The attention to detail she puts into her appearance is way beyond anything I have experienced before. Her high end designer lingerie is exquisite! Her looks are matched in equal parts to her bubbly fu...
  11. BY Andrew

    And when struggling for words, I turn to song. And with apologies to Billy Joel “she has a way about her”. Olivia, is one of those ladies who has a presence, and a twinkle in her eye. A great conversationalist who looks at home in any corporate setting. And a wonderful, talented and generous lov...
  12. BY Geoff

    Last evening I had the pleasure of the company of an absolutely delightful young lady - so delightful the memories are still lingering today. It took some time to align our schedules, but Olivia's communication leading up to our agreed date was excellent, and during the course of making arrangeme...
  13. BY Mr N.

    I am a mature aged professional man. I was fortunate to meet Olivia 6 months ago and have had an ongoing arrangement since. Last weekend I was heading to Noosa for some winter sunshine and thought how wonderful it would be to fly Olivia up to join me for a couple of days. Olivia is a beautiful woma...

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