But despite the good times she had as an escort, the 36-year-old said if she could have her time over again, she would not have gone down that path.
In her recently released book – appropriately titled 10,000 Men and Counting – Ms Montenegro writes very frankly about how she was gang-raped at 18, started dancing on table tops at 19 and how she became a ‘high-end’ escort by 21.
But the now-business entrepreneur didn’t start her life out as a wild child.
The Melbourne woman was born into a family with deep Christian values and wanted to ‘save herself’ until the right man came along.
She started in the sex industry when she was 21 years old after she was a table top dancer for three years
But after she was gang-raped during a night-out at a club, coupled with her low self-esteem and her lust for money, she started off table top dancing before heading into sex work.
‘I saw an ad for table top dancing back when I was about 19,’ Ms Montenegro said.
‘I was very naïve – it’s like I fell off the bus.
‘I got pretty drunk and I made $1000 cash on the first night.
‘I thought that was amazing and I thought “I must be quite decent at it”.’
To cover up she was an escort, the now 36-year-old told her parents she was modelling
The positive attention she was getting from clients was a far cry from her days of being bullied in high school.
‘It actually gave me the confidence I never had,’ she said.
‘For the first time, I connected with people, with the other girls, and it made me flourish.
‘It was like a family. That’s the good side of it.’
But after three years, Ms Montenegro took the leap into the world of escorting – working mostly in Melbourne.
Later in her career, as she ‘worked up the ladder’, she expanded her services to all over Australia and other parts of the world where escorting was legal.
Gwyneth Montenegro – a pseudonym she created to pen her book – said she went by many names while she worked in the industry.
The thousands and thousands Ms Montenegro earned as an escort was spent on a new car and luxury clothing
But the face on her book was her real face.
‘All the photos of me is like me “coming out”,’ she said.
‘I didn’t want to go by my real name because obviously I wanted to protect my elderly mother, who is 77, from it all.
‘I’ve gone by a few working names. One of them I went under was Angelina. I had to have a sexier escort name and who better than Angeline Jolie? ‘
Ms Montenegro said her main clients were white-collar workers peppered with well-known faces – including lawyers, politicians and musicians.
To ease her guilt and numb her to the idea of being an escort, Ms Montenegro blew the ‘thousands and thousands’ she earned on a new car and clothes.
‘When I moved up in the escort world, I was meeting more influential and richer clients and I had my first experience with cocaine in my early 20s and it was real A-grade stuff – he was a multi-millionaire. I thought: “Wow, this is really cool”,’ she said.
‘I ended up actually taking cocaine for six to eight months and I was also on speed.
‘It was a lifestyle of cocaine, speed and French champagne.’
It was this kind of destructive lifestyle that motivated Ms Montenegro to pen her book.
‘People have certain perceptions of escorts – you don’t know who could get into it – and I wanted to de-stigmatise it,’ she said.
‘For those who want to go in to it, I want to get them to really think about it because once you get into it, it really lives with you.
‘And I also just wanted to give those people in the [sex] industry a voice because I’m a human being, they’re human beings.
‘The main thing for me is that if I can change one person from making that decision [to enter the industry] then I would have done something good, something meaningful and that would mean a lot to me.’
But there was no one to help Ms Montenegro when her life was skidding out of control and she wanted to get out of industry.
‘The money was why I stayed for so long. I was earning thousands upon thousands a week,’ she said.
‘Money was like a drug – it let me fly around the world.’
One of the few perks of her job was being flown around the world and let her escape the reality she was living in.
‘One of the most memorable moments I have was getting flown out to Bora Bora,’ Ms Montenegro said.
‘It was a companionship – it was more a boyfriend experience booking. What made it so memorable was it was beautiful there and I felt like a princess.
‘It was really funny because it didn’t feel like work as it were.
‘It was just an escape for me – I was treated like a human being – so it was pure escapism for me.’
Gwyneth Montenegro has finally achieved her dream of becoming a fully licensed commercial pilot at 29 years old
Unfortunately for Ms Montenegro her new-found career was cut short because of kidney failure, preventing her from renewing her pilot’s license
Ms Montenegro would disguise the money she made through promotional modelling job.
During her days as an escort Gwyneth Montenegro chose Angelina as her pseudonym inspired by the actress Angelina Jolie
Though Ms Montenegro said she had no ‘horror stories’ to tell about her time as an escort, she desperately tried to turn her back on the industry.
After she was almost killed in a car crash at the age of 24 while driving her Volkswagen Golf, Ms Montenegro made the brave decision to get out.
‘I walked away with severe whiplash and shock and bruises, but I was lucky I walked away virtually unscathed,’ she said.
‘Thank God for German engineering. It was really my wake-up call.’
At the time of the crash, Ms Montenegro’s parents thought she was earning her wage as a model but the trauma of her accident sparked a hospital-bed confession about what she was really doing with her life.
‘Money was like a drug – it let me fly around the world:’ Ms Montenegro said the temptation of making good money while escorting was one she could not refuse
Ms Montenegro writes very frankly in her newly released book about how she was gang-raped at 18, started dancing on table tops at 19 and how she became a ‘high-end’ escort by 21.
‘I was very close to my parents, particularly my dad,’ she said.
‘I did a little bit of promotional modelling, and how I was able to hide my money and I was able to disguise my money outwardly – new clothes and a new car and everything – was by explaining it through the modelling work I did.
‘I was able to hide it pretty well but it was killing me on the inside to keep it such a secret too.’
Luckily for Ms Montenegro, even though they didn’t like it, her parents were understanding and supportive when they discovered the truth.
After the accident, things started to look up when she finally achieved her dream of becoming a fully licensed commercial pilot at 29 years old.
But her new life as a charter pilot and doing scenic tours was cut short when she diagnosed with kidney failure, which prevented her from getting medical approval to keep her licence.
Again Ms Montenegro fell back into the industry, but finally at 33 she retired and cut off all ties with it when she met her business partner, known only as Roger.
She started a course in neuro-linguistic programming and together with Roger they started building a business.
‘It’s like mind science – like (famous US life coach) Tony Robbins does – it’s like a new age psychology, and it really helped me deal with a lot of my issues,’ she said.