Adopted from the video, Adams in Heels
“Annie” is a closet transvestite who cross-dresses to fulfill his own sexual desires. Since young, “Annie” has a fetish with women’s underwear and uses “Annie” as a role for him to portray his fantasy girlfriend. He feels that cross-dressing is not something to be proud of, and has felt embarrassment and guilt and tried to stop without success. As he fears getting found out by his friends, he has to cross-dress in privacy and thus feels very much isolated, as it is difficult to find other cross-dressers. “Annie” also feels that cross-dressing is a perversion that goes against society norms as it requires him to ‘steal’ female gender roles.
Helda’s drag queen career started as a performance for a club in Boat Quay. Since then, the audience’s compliments act as motivation for him and encouraged him to continue with this career. Cross-dressing as a drag queen has also led Helda to find his self-worth and think of himself as someone important. Helda feels that cross-dressing allows him to show two sides of him, his feminine side besides his masculine side. With regards to societal objections, Helda is a drag queen who performs for himself and will not stop because of what others think of him.
Erin is a transsexual has been indulging in femininity since young through influence from Sherry, her older brother who is a drag queen performer. Erin started cross-dressing as she felt like a woman, not a man at all. Despite facing violent objections from her family, Erin was determined to go for sex change operation which since then has allowed her to be who she really wants to be.
From Benjamin to Bernice
source: http://www.trevvy.com/scoops/article.php?a_id=51&c_id=3

Benjamin was a famous drag queen who went by the name 'Bernice' in the Singapore gay clubbing scene! He started becoming a drag queen due to his involvement in the Action for Aids project, but is now enjoying his career as one. In drag, he has to take on the mind of a woman and act like a woman. His career as a drag queen hence jeopardized his relationships with his friends and family as most of them were unable to accept him in women's clothings. Thus, Benjamin decided to retire from his drag queen career in 2007 and go back to his normal gay lifestyle and hopefully get into a relationship as "most gay men in Singapore are simply unwilling to consider a serious relationship with a drag queen".
