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10 Intimate Questions You Always Wanted to Ask a Male Escort for Women

Ever been curious about what a male escort for women really thinks about his job? In this piece, one of Her Confidant’s companions spills the beans on a bunch of really intimate questions.

 

From surprising requests and making genuine connections to some seriously funny and heartwarming moments, you’ll get a peek into the ups, downs, and everything in between. Whether you’re after the emotional bits or just some juicy stories, these answers will give you the lowdown on the life of a male companion. Let’s get to it…

1. What’s the Most Unexpected Request You’ve Ever Received?

It wasn’t weird so much as it was spontaneous and different.

 

A client in her late 20s wanted to lose her virginity in a special way. So, she called Anna to book a last-minute weekend with me in a little cabin in the Dandenong Ranges near Melbourne. She later confessed that if Anna or I had shown any hesitation, she would have hung up the phone and never called back. Thankfully, I love being spontaneous, and I felt that’s what she needed, so I jumped right in.

 

She picked me up, and I could tell she was nervous while driving. To help her relax, I started asking light questions about her week and made jokes throughout her shy replies, which slowly led to deeper conversations about her life and goals. We discussed why she chose an escort to have her first intimate experience, and she opened up in such a raw and honest way that it helped me understand her better and be there for her in the way she needed.

 

When we got there, we found the cabin was cozy and secluded. Which sounds like a dream, except at one point, the power went out. It was pitch dark, and we both froze for a moment before bursting into laughter. We fumbled around with our phones, using the flashlight to find candles and matches. It turned into a hilarious situation, with us tripping over furniture and bumping into each other. Once we got the candles lit, the room filled with a warm, flickering glow, which added an unexpectedly romantic touch to the evening. We joked about the cliché, our lack of survival skills and how we would never make it in the wild. The whole situation made us both relax so, by the time we were together, she was comfortable and free.

 

The entire experience was very powerful. It allowed me to connect deeply with her during such a vulnerable moment. Being able to provide her with a beautiful, memorable first experience was truly an honour. It reminded me of how important it is to be present and caring, especially when someone is trusting you with such a significant part of their life.

2. How Do You Create Genuine Connections with Clients?

Creating genuine connections starts with active listening and remembering the small details—favourite books, childhood memories, pets’ names.

 

One regular client loved discussing literature, and we would spend hours dissecting her favourite novels, in between intimacy. Remembering our past discussions and bringing them up in future meetings made her feel valued and understood. For instance, she adored poetry, and I surprised her by reciting lines from her favourite author during our third meeting. This sparked deep, intellectual conversations and personal stories that brought us closer.

 

These gestures show women that you care and are invested in their interests and well-being. I love my job because of moments like these. It’s not just about being an incredible lover—though I do hear that quite often — but more about how you make people feel around you. That’s what truly moves me.

3. What’s the Nicest Compliment You’ve Ever Received?

A client once told me that our time together helped her rediscover her confidence and sense of self-worth. She had gone through a rough divorce and felt disconnected from her sensuality, not having been intimate with anyone for over 10 years.

 

After a few meetings, she felt encouraged to start dating again. She initially came to me feeling broken and ashamed, but through our encounters, she began to see herself in a new light, like her old — yet revamped — self. The day she told me she was ready to date again, her face beamed with happiness.

 

It takes courage to step out of your comfort zone and seek help. That’s why breaking stigmas is so important — it shouldn’t take 10 years for someone to reach out for help to navigate their sexuality. The more we discuss this, the easier it will be for every woman to use this powerful tool for their emotional and physical benefit.

 

Knowing that our interactions contributed to her healing and self-rediscovery was incredibly fulfilling.

4. How Do You Balance Physical Intimacy with Emotional Boundaries?

Balancing physical intimacy with emotional boundaries is all about clear communication and mostly, empathy.

 

I had a client who started to develop feelings, and it was important to handle the situation with care. I genuinely appreciated her feelings and took it as a compliment, but I knew we needed to keep things professional to protect both of us. We had a nice conversation where I gently explained that while I valued our time together, we had to set clear boundaries to avoid any potential heartache. I emphasised that her emotions were valid and natural, given the genuine connections we build.

 

By having an open and honest conversation, she felt supported, and I felt respected. It’s about being there for them emotionally, but also knowing when to draw the line to ensure both parties are protected and safe.

5. What’s Your Go-To for Making Clients Feel Comfortable?

A warm smile and genuine interest go a long way.

 

I start with light, easy conversation to break the ice. Once, a client was incredibly nervous at our first meeting, almost shaking and unable to look me in the eye. I suggested a walk in a nearby park before dinner, pushing the restaurant booking back a bit. The fresh air, physical movement, and a few laughs about the situation helped her relax.

 

By the time we sat down to eat, she was much more at ease, setting the stage for a positive and enjoyable experience.

6. What’s a Common Misconception People Have About Your Job as an Escort?

Many people think it’s all about the physical aspect, but that couldn’t be further from the truth. A large part of my job is emotional labour — providing companionship, empathy, and understanding.

 

I once had a client who just wanted someone to hold her and listen while she talked about her stressful job. She was a high-powered executive, always under immense pressure. During our encounters, she vented about work in a way she couldn’t with anyone else, and I listened attentively, offering support and understanding.

 

Sometimes, all she needed was a hug and a few comforting words; other times, feeling relieved turned her on so much that we naturally transitioned to other activities.

7. Have You Ever Had a Client Teach You Something New About Yourself?

Absolutely. One of my clients was a professional vocal coach, and between laughs, she decided to give me an impromptu voice lesson. We started with humming scales to get my vocal cords warmed up, then moved on to tongue twisters to improve my diction. It was pretty funny, I must say.

 

Next thing I knew, we were singing “I’m on Fire” by Bruce Springsteen. I did pretty good—or at least she said so. Maybe she was just being nice because we were sleeping together. I’ll never know.

8. What’s the Funniest Thing That’s Happened During an Appointment?

Once, I spent a week with a client, and she had a friend visiting for coffee one day. She asked me to help prank her friend by pretending to be a clueless handyman fixing things around the house during the visit. We planned it meticulously, and I showed up in tight jeans with a toolbox, acting completely out of character.

 

Her friend’s reactions were priceless as I “fixed” imaginary problems and asked ridiculous questions like, “Is it normal for the sockets to buzz when I plug something in?” and “How often should I change the air in my tyres?” The laughter was contagious, and by the end, we were all in stitches. The whole situation was hysterical.

 

And before you ask, no, it didn’t turn into a three-way party. My client wanted me all to herself; and that’s exactly how it went.

9. How Do You Make Each Experience Unique for Your Clients?

It starts with understanding what makes each client tick. If it’s a first-time or one-off encounter, I actively listen, paying attention to body language and how they react to each interaction. For regular clients, I dive even deeper.

 

One client in her 60s loved vintage films, so I proposed a movie night with a projector and popcorn. She mentioned her love for black-and-white films, so I set up a cozy space with blankets and her favourite movie. We spent the evening watching a classic and discussing the storyline and her views on modern cinema. This created a natural, intimate connection, showing her that I genuinely listened and cared about her interests.

 

The idea behind all this is that it’s all about you. So, these thoughtful gestures can turn a simple meeting into a memorable and meaningful experience.

10. What Do You Enjoy Most About Being a Male Escort?

What I enjoy most is the diversity of experiences and the chance to make a positive impact on someone’s life.

 

Every woman is different, and each encounter teaches me something new. Whether it’s helping someone regain confidence, providing a listening ear, or sharing a laugh, the connections I make are incredibly rewarding.

 

The variety keeps the job exciting and fulfilling. And yes, the pay is good, and the sex is great; I won’t lie. I have a high libido, so I’ve found a way to use that to my advantage. But, knowing I can use my time to make a difference in someone’s life, even in a small way, is what truly makes it all worth it.

Bonus: Why Don’t You Show Pictures of Yourself on the Website?

I have a pretty important role in another industry. So I keep this part of my life under wraps.

 

Honestly, it gives me a bit of a thrill — like living a double life, which is kind of exciting and quite a turn on, if I have to be honest.

 

It’s my way of staying protected. But don’t worry! I always encourage new clients to book a 20-minute Meet & Greet so we can see if the energy is right. Trust me, real life is way better than any photo on a website.

 

See you soon, I hope.

Chris

Discover the secret to your sensual truth with Her Confidant – Australia’s premier male escort agency for women, by a woman. From a handsome plus-one to a bespoke sensual adventure, we’re at your intimate service.

 

Get in touch with us to book or have a confidential chat about your needs on 0449 918 907.