Not a bed of roses
Sex work was not Sherry’s first choice of work. She dropped out of school when she was fifteen, after daily taunts from her classmates took a toll. For four years, she worked at a fast-food restaurant before enlisting in the army. After completing her national service, she — then still a pre-transition transgender woman — worked at a semi-fine dining restaurant as the hostess, sitting guests and recommending chef’s specialities. ‘I enjoyed the interaction with people, I enjoyed very much being the front person who connected with patrons.’ However, when the desire to express herself as a woman far eclipsed her need to hide her true self, she began dolling herself up. Her then colleagues began alienating her and became more distant. And without warning came her termination: her superiors cited a poor work performance and tardiness as reasons.
Shunned and stigmatised by society, for many transgender women in the early aughts, sex work was one of the few livelihoods they could turn to. It was a personal friend of Sherry who roped her into the industry. At first her family disparaged her outfit choices ad nauseum, but eventually that turned into indifference. ‘My family didn’t probe about my work, but it doesn’t take a genius to know that I was moonlighting: I’d doll myself up, head out of the house late in the afternoon and only come home past midnight. I didn’t have a day job, yet I could pay for what I wanted. I was lucky in that I didn’t get abused by my own family members, as is the lived experience of many transgender women.’
Sex work, like all other jobs, is work. ‘“Tough” was not knowing what’s going to happen. Every night, while my mind was set on making a few hundred dollars, I wasn’t sure of the type of men I’d meet.’ Thrust suddenly into an uncertain world, Sherry had to learn the ropes, first by identifying potential clients. A car circling the vicinity of the park several times. Sheepish eye contact. In hindsight, there were many close shaves with the police. While sex work is not illegal in Singapore, soliciting is, and therein is where the line is blurred. ‘I didn’t feel scared until my sex worker sisters told me to be wary of undercover and uniformed cops. Just imagine: a woman with a bagful of contraceptives — it’s not hard to suspect vice-related activity. They taught me to quickly walk away and avoid being questioned.’
While her would-be clients were discreet, hecklers, many of whom were her age, were rambunctious. ‘Faggot’ some would berate her. Others would ask her for the price or harass her with faux kissing noises. Eyes followed her every move, even if she didn’t ask for the attention. Kids would stare, out of curiosity, when she was in a coffee shop, her short skirt and skimpy dress incongruous. ‘Whenever I was in a coffee shop, I’d tone myself down and not be flamboyant or loud. Some men would try their luck and ask me for my price. That’s not very nice: if indeed you really wanted to engage my services, you’d know where to find me. I just needed somewhere to eat, to have my meal. I was not there to solicit business. I understand that the way we dress can cause discomfort, but sex workers have every right to have a meal in peace. And then we’ll leave without causing any trouble.’
The first time she completed a transaction, Sherry says feelings of disgust gnawed at her. ‘I felt dirty. Had I a choice, I would want to be intimate with someone I had a connection with. But I was doing this for money.’