She was torn when two of her three sons decided they wanted to become women.
It was a double whammy Madam Monica soon grew to accept.
Her sons, dressed as girls, took part in transvestite beauty pageants and made waves.
They then went for sex change operations.
On Friday night, more than a decade after they first told their mother about their sexual inclinations, one of them emerged a beauty queen again – at the age of 38.
Ms Angel Aurora Jalleh-Hosey beat 12 other finalists to be declared Miss Exotica 2012, a competition for transgenders in Singapore and around the region at Talent Cafe in Tanjong Pagar.
The title is apt. Ms Angel was formerly a Mister and so was her sister, Ms Jessie Jalleh-Hosey, 37.
The sisters dropped their original surname of Hutchison for Jalleh-Hosey, an amalgamation of their parents’ last names.
Ms Angel’s latest win was her second attempt at a beauty title this year.
Her sister, who was in the audience dressed in a tight black lace dress, is also a former beauty queen.
In 2004, The New Paper reported that the Ms Jessie won the Miss Tiffany Singapore 2004 title, while her elder sister took the second runner-up position the same year.
They were still officially men then.
Both brothers-turned-sisters hung up their pageant heels for eight years before Ms Angel decided to get back into the game in June.
“We took a break because we both went for our sex change operations in 2005,” said Ms Angel, who volunteers for Home (Humanitarian Organisation for Migration Economics).
She is involved in getting sex workers to go for free HIV and Aids tests every month, and distributing condomsand pamphlets to them.
“Once we became women, we thought we’d take a break.”
The two women grew up as brothers until 2005, when they went for sex change operations on the same day in Bangkok, Thailand. The sisters have a younger brother who is 26.
“We ‘long chiam pas’ (played a game of scissors, paper, stone),” said Ms Angel. “I won, so I went first, in the evening, then my sister went later at night.”
The money for the operations – which cost US$6,500 ($7,960) each – came from the Ms Jessie’s then-boyfriend.
“We supported each other through it,” said Ms Angel.
Their mum, too, was there with them, having accepted her sons’ wish to become women years before.
“It was tough at first, but everything is okay now,” said Ms Angel.
She started wearing women’s clothes and taking female hormones at the age of 18, while her younger sibling did so five years later.
Back then, Ms Jessie told Chinese daily LianheWanbao: “When Angel started dressing like a woman in 1993, society was still very conservative and people would give her curious looks.”
When The New Paper on Sunday approached the girls’ mother, she declined to give her full name. The shy woman said she wanted to be known only as Mrs Monica.
She was overjoyed that her daughter had won yet another beauty pageant title. “Tonight, it’s about her,” she said.
“Something good has come out of (all of this),” she said.
Mrs Monica, an Indian Singaporean, is divorced from her Slovakian husband.
Ms Jessie has stayed away from pageants since her 2004 win, since she “won the biggest one already”.
“She thought, ‘why not let other people join?’” said Ms Angel.
After she had her sex change operation, Ms Angel got married to a Chinese Singaporean man. But the marriage ended in divorce after a year. She declined to say why.
In June this year, she decided to get back into the game with the Tru Me Pageant 2012, held at local club Play. She emerged runner-up.
“I thought I was too old already for these things,”she told The New Paper on Sunday. “But the moment I went onstage, the confidence came back.”
On Friday, Ms Angel, dressed as “Miss India”, wowed the audience. The contestants “represented” exotic countries that are usually found in beauty pageants, like Puerto Rico, South Africa and Zimbabwe.
For the talent portion of the competition, she danced to a Hindi song, Maar Dala, from the Bollywood hitmovie Devdas.
The crowd whooped when the music suddenly switched to Psy’s Gangnam Style, with Ms Angel confidently doing the horse-riding and hand-on-hips side-to-side dance.
“That was actually my sister’s idea,” she said.
The mix of contemporary and classical Indian costumes that she wore for the finals – there were five costume changes in all – were all sourced or designed by Ms Angel herself.
She revealed that her glamorous saris were made from material bought for less than RM100 ($40) in Kuala Lumpur.
Her immaculate hair and make-up, captivating costumes and the showmanship weren’t the only factors that swayed the judges.
Ms Angel also impressed during the question-and-answer round.
Asked by judge Maia Lee what she felt was one of the biggest misrepresentations of the LGBT (lesbian, gay, bisexual and transgender) community, she said: “That we are different.
“We can do things that everyone can do, like beauty contestants. Look at me, I can be here,” she said, before the rest of her answer was drowned out by catcalls and cheers from the audience.
While she candidly admitted that she has become “fat”, Ms Angel feels she has enough experience to work with the Miss Singapore Universe pageant organisers, since it was announced this year that the international and local competition will, from next year, be open to transgender contestants.
She will be travelling to KL next year to compete in the Miss Universe World pageant. She said she is keen to help any transgender contestants in next year’s pageant.
“I think I could give them some help and advice,” she said. “I can help them choose unique and beautiful dresses.”
After seven years of going for collagen injections and taking vitamins to keep her looks, she clearly knows what it takes to be at the top of her game.
Said Ms Angel: “It’s not easy being a woman, you know.”
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