Olivia Winsome

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

Location: Melbourne, VIC

My Stats

Age 30s

Height 172cm

Eyes Green

Hair Brunette

Body Type Slim

Ethnicity Caucasian


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


  • Please ask me about my services

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


Standard Services

Meet for a drink or breakfast and build a little excitement for whats to come...
Lets take our time getting to know one another over dinner or lunch prior to play..
(12 hours) Wake up next to me. *I will require a min of 6 hours sleep

Additional Rates


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…)

Patron’s List
For gentlemen who wish to receive periodic updates from me, my patron’s list is the only place I ever off promotions (never say I don’t spoil you!) I don’t want to ruin the surprise, but let’s just say you’ll receive a few risqué images upon sign-up… Join the list by visiting oliviawinsome.com/patrons

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