Unlike many other transsexuals in Asia who prefer to live privately because of the social stigma of sex change, the British-educated, Singaporean transsexual woman has chosen to live a normal life, but in public.
Smart, confident and articulate, the communications specialist who heads her own public relations company has embarked on a mission to help turn around the "culture of shame" surrounding transsexuals in Singapore and the region.
"Somewhere out there, not just in Singapore but throughout Asia, there are lots of young people who are suffering the way I suffered years ago," Leona, 32, tells AFP in an interview.
In her former life as a man, she was called Leonard.
These days, she draws on her experiences of gender identity crisis, rejection and discrimination to challenge social mores on behalf of the so-called silent community.
"It's this entire culture of shame that gets under your skin. It's not something that you can isolate and demolish because it is so much a part of our culture," she says.
While a few transsexuals are gaining prominence in Asia -- notably China's Jin Xing -- most continue to live in silence.
In May, a 32-year-old South Korean transsexual entertainer, whose sex alteration led the country to change its family registry laws, married her rapper boyfriend.
Parinya "Nong Toom" Charoenphol's rags-to-riches story was made into a movie, "Beautiful Boxer." Former Chinese People's Liberation Army colonel and now woman Jin Xing is a prize-winning dancer and choreographer.
Slim and taller than the average local woman, Leona packs charm and gets animated when talking about children.
But her lipsticked mouth creases into a pensive smile when she says: "I can't bear children. I have to be on hormones for life and I have this body structure of a guy."
The hormone treatment has "feminised" the former man. While traces of masculinity are evident, Leona says she has already come to terms with being a woman -- although a transsexual one.
"I can't deny that biologically I'm different," says Leona, wearing a blue dress, the muscles on her shoulders and arms clearly visible.
Discrimination is the biggest challenge faced by transsexuals, she says, recalling repeated rejection by prospective employers in Singapore despite her academic credentials.
"Singapore may be a cosmopolitan city, but many things are still swept under the carpet," Leona says.
No reliable figures on the number of transsexual men and women in Singapore, or the region, are available, mainly because those who feel they have been born in the wrong body prefer to endure their situation in silence rather than embarrass their families, Leona says.
"It's because a lot of transsexual women face discrimination at work and experience failure of relationships that a lot end up in suicide, depression. They end up on the streets as prostitutes," she says.
This is why she has taken time away from her thriving public relations consultancy promoting beauty products to wage her campaign.
After much persuasion, one local university allowed her to speak to an audience of students but she is finding it hard to pry open a window to share her thoughts in the corporate world.
On September 14 she is to launch her autobiography, "From Leonard to Leona -- A Singapore Transsexual's Journey to Womanhood."
From Singapore, Leona plans to travel across Asia to bring her message for greater tolerance of gender diversity.
Medical experts on gender believe transsexualism is a medical condition, and that transsexuals are different from transvestites and homosexuals.
In contrast, transvestites are always males and do not dislike their genitalia although they may derive sexual arousal through dressing as women, Goh said.
For transsexuals, dressing as a man or a woman for one year before a sex change operation is part of the transition process and is not related to any sexual pleasure, the experts say. The surgery is "the finishing touch," Goh wrote.
Leona says the association of transsexuals with prostitution in Singapore harks back to the 1960s when there was a flourishing culture of drag queens, including some transsexuals, on Singapore's Bugis Street.
As Singapore transformed rapidly into a modern Asian business centre, the government cracked down on Bugis Street. Transsexuals were lumped together with homosexuals, transvestites and prostitutes.
It was in this environment that the young Leonard -- Leona's original identity -- grew up.
As early as age 10, Leonard had already started developing feelings for boys.
But he was forced to remain silent because of a dearth of information about transsexualism and for fear his traditional Chinese family would be scandalised.
"I did not think I was gay. I just felt that I was a woman trapped in a man's body," says Leona, who has a younger sister.
At age 15, Leonard discovered a book about transsexualism, which sowed the seeds of his eventual decision to undergo a sex-change operation in 1997.
"I discovered that book in the library and I said 'Oh my God! There are actually people like me!'" she reminisces.
"That changed my life and I discovered that I could go for the sex change operation."
As an able-bodied man, Leonard entered Singapore's compulsory two-year military service at around 19.
Pressures of being forced to be "macho" during the training led to a nervous breakdown and drove him to attempt suicide by drug overdose, she says.
After military service, Leonard in 1996 went to study in Britain, where a more tolerant university environment allowed him to cross-dress for a year as part of his preparation for sex-change surgery.
In 1997, Leonard flew with his tuition money from Britain to Bangkok, where he walked into a clinic for the life-altering operation.
"I was afraid. I could go in and I could die. But I knew at that point that I was going to change my life forever," she recalls.
"I had carried that burden within me for so long and I couldn't live anymore without doing it."
Leona endured a lot of pain during the procedure, which took 14 days, but the feeling of having a new identity was "wonderful, euphoric!"
She warns other transsexuals who might be considering sex change surgery that getting a new identity "is not a magic wand" and they will have to live under a culture of shame and discrimination.
Family support is crucial. Her mother was the first person she told after the operation, and her father had already learned to accept her for who she is.
"By that time, they had already decided that they would rather have me as a woman than lose me as a child," she says.
What is her dream now?
"To be a wife and a mother," she says. "I look forward to a fulfilling relationship with a loving man, getting married and adopting three children.
"I've also reached a critical juncture where I'm more self-assured and finally able to lay to rest the painful aspects of my past and move confidently as a woman."