After years of planning and waiting, he finally took the first step towards being legally recognised as a man.
Christopher Khor was born with female genitalia but has been identified as male since childhood.
"I've always known I was transgender," said the 23-year-old assistant producer who works in the television sector. I was in kindergarten when I saw the distinction between genders, and related more to the males. I just saw myself as a boy."
He learnt of the term "transgender" at 16, and soon after, of the complications involved.
To legally change his gender marker on his identity card, he needed to surgically remove his breasts, ovaries and womb.
There were many causes for hesitation - among them the social perceptions attached to sex change and the costs of such transformations.
Surgery to remove his breasts alone would cost about $15,000 in Singapore at a private clinic with public hospitals no longer offering the procedure.
But Mr Khor felt it was a change he needed and began preparing for surgery, first going on steroids that gave him a deeper voice and more facial hair.
After scouting for alternatives, he decided to have the breast removal done in Bangkok, and this month successfully completed it at a cost of $4,400 - about a quarter of the expense here.
But it was not without its difficulties.
He "nicked an artery" from excessive movement after the operation, and "bled so much" that the doctors had to put him back under anaesthesia to sew it up.
But "beyond that, everything went great". It helped that his girlfriend made the trip with him, and assisted with post-surgery care.
Mr Khor has taken 14 days of annual leave for the surgery and recovery, and it will be another two months before he can return to more strenuous activities, as well as show off his new upper body when he finally gets to swim topless.
His employers are aware of his transformation and are supportive. His mother, a nurse, and father, a physics teacher, are "coping with it".
"They are not supportive of the surgery itself, but of me," he said.
Plans for the removal of his ovaries and womb, at the end of next year, are in the works, said Mr Khor.
He also raised $14,000 through crowdfunding earlier this year to do a film project to document his reconstruction, with the money going towards equipment and travel costs for a crew of four, including himself.
"I always knew I was going to pursue surgery - just didn't know how public I was going to be about it because it is easier to not have to face discrimination."
His documentary, likely to be the first on transgender men in Singapore, is an effort to erase that stigma: "We are too invisible as a community, and I want to let others know it's okay to be transgender."
