Meet Winston

Male escort for women in Sydney holding a wine glass.

Male escort for women in Sydney facing a window dressed in blue.

Male escort for women in Sydney laying on a bed.

Male escort for women in Sydney removing blue shirt overlooking the harbour.

Male escort for women in Sydney shirtless in white pants.

Male escort for women in Sydney in a light suit.

Male escort for women in Sydney facing a window.

Male escort for women in Sydney undressing.

Photos by Laura S

Passionate, Sensual, Seductive & Adventurous

Based in: Sydney

Caters: Women & Couples

Height: 5.9 ft

A Song: Sugar Mountain, DJ Honey Dijon

A Movie: Any sci-fi comedy

A Quote: Carpe Diem, live in the present moment

A Turn On: I love authentic and self-empowered women

Fun Fact: I speak multiple languages

Gives: Winston from How Stella Got Her Groove Back vibes

Meet Winston

Hi there!

I’m a well-travelled, multilingual soul who thrives on meaningful connections and finds deep conversations utterly captivating.

I take pride in being a companion who enjoys satisfying my liaisons on every level; mentally, emotionally, and, of course, physically. I’m a natural listener, making every moment feel effortless, engaging, and fun.

I stay active and love keeping fit through sports and outdoor adventures. My passion for travel and discovering new cultures inspires me, and I adore sharing those experiences with like-minded people. Food is another passion of mine; I enjoy exploring the culinary arts and would love to share those intimate, delicious moments with you.

You’ll find my smile warm and inviting, layered with humor, seduction, and a touch of sua de vive. I believe in creating tactile, sensual moments that leave you feeling deeply fulfilled and completely at ease.

Grace, elegance, and individuality define me, but what I admire most is the ability to connect, laugh, and truly enjoy life’s little moments together.

I can’t wait to meet you!

Tattoos are blurred or deleted to protect the companion’s privacy.

All Companions

Our satisfied clients are saying...

Wow, what a night! So much more than what I expected. I felt so incredibly at ease, comfortable and respected. Feeling that spark reignite inside of me again. He took me to places I haven't been for a long time. I felt special, adored and sexy. Just what a single woman craves and desires. Thank you so much Anna for an incredible experience, your guidance and caring nature.

Sam

It was an unforgettable, transformative and fun experience for me. It gave me an incredible boost of self confidence. I began to reclaim my sense of womanhood and attractiveness, and started plans to leave my marriage. I would recommend to any woman (even if not having been in my situation), who craves touch, to access these services.

Kate

I recommend this experience to any woman who wants great company and to feel her best self. The emotions I felt during my experience were very real and have made me realise that I was in fact, a tactile, sexual woman and that I can and should have fun. The boost of confidence gifted to me stays with me and has become a treasured memory.

Alexandra

I discovered a new level of sexuality, confidence and capacity I hadn't realised I possessed. The best thing in all of this is understanding that I have so much left to uncover… particularly as my confidence and sense of self grows. This is not a happy ever after, but a continuing adventure in sexual discovery and I look forward to exploring further in this safe space.

Anne

It has been a privilege to use this exceptional escort agency. Bokeem was not only handsome but also so highly intelligent and worldly. He immediately made me feel at ease and comfortable. He was so much more than I had imagined. Looking forward to my next rendezvous…

Steph

Since making a booking, what can I say, I am addicted. I have found the service you provide to be of first class and I have recommended your agency to my friends. Thank you Anna for all your wonderful help.

Jo

It was a pleasure dealing with your agency. I believe that I have found the best service provider in the escort industry. I have used Her Confidant numerous times, and I have to say that the service has always been exceptional.

Mel

Wow!! What can I say! Thank you Anna for making my experience so incredibly amazing and memorable. Should have done this years ago, don’t know what I was afraid of or what I was waiting for? Thank you, thank you, thank you... Till next time.

Clare

Curious?

As seen on

Articles & Mentions

Latest Posts

Male Escort for Women in Melbourne Wes showing his belly

Why Emotional Intelligence Belongs in Companionship

Looking for more than talk therapy? We explore the powerful intersection of psychology, coaching, and high-end male companionship, where emotional intelligence meets sensuality. At Her Confidant, we believe intimacy is more than sex; it’s self-care. For women navigating life post-divorce, burnout, trauma, or just craving meaningful connection, an emotionally intelligent escort can offer the kind of presence, touch, and attunement that rewires self-worth at the cellular level. From understanding trauma-informed touch to honouring consent as a living practice, our companions aren’t just attractive, they’re attuned, grounded, and emotionally safe. Learn why so many women are turning to companionship not instead…

From Fantasy to Reality: A Couple’s Guide to Booking an Escort for Threesomes

You're thinking about opening up your relationship, but not sure where to start? You’re not alone. More and more couples are exploring intimacy beyond monogamy, not out of lack, but from a deep desire to reconnect, reimagine, and reignite. Whether it’s about fulfilling a fantasy, watching your partner glow, or just stepping outside routine, this guide will show you why booking a male companion might just be the sexiest (and safest) way to start. Written by psychologist and sexologist Laura Lee, this is your invitation to explore pleasure, on your own terms, together.

Power, Pleasure & FIFO: Women in Trades Reclaiming Intimacy with Male Escorts for Women

The FIFO and mining industry has been transformed by women; leaders, decision-makers, trailblazers breaking barriers in a world that wasn’t built for them. But success often comes at a cost. Long hours, isolation, and a male-dominated environment leave little room for intimacy, connection, or even acknowledging the need for pleasure. Dating feels impossible, relationships struggle under FIFO schedules, and finding emotionally intelligent men who truly understand is a challenge few talk about. But what if there was a different way? One designed for women who don’t settle, for success, for love, or for pleasure. This article explores how elite male…

Meet Winston

Our satisfied clients are saying...

Sam

Kate

Alexandra

Anne

Steph

Jo

Mel

Clare

As seen on

Latest Posts

More content on our Instagram