The trade in the area prompted George Hawkins, then an MP, now on the Local Board, to introduce a bill which would allow the city council to ban sex workers from specific places. The bill is still before a select committee as groups representing community and sex workers negotiate the details - a proposal to shunt the workers a kilometre away from their stamping ground doesn't look like it's going to fly.
"It's important that everyone works together to come up with a solution that works for everyone," Pickering tells me. "Street sex work has been prevalent in Hunter's Corner for 14 or 15 years. A lot of the workers live in the area. They don't want to come into K Rd because it's too far to go.
"But we have an understanding with the council that the workers will only work between 9pm and 6am, and there are no-go zones - we keep away from residential areas."
In partnership with Charlotte Ama, from the Auckland City Mission's Outreach programme, Pickering works a night or two each week, keeping track of how the workers are doing, spotting new arrivals, inquiring after old hands.
They hand out "street safe" packs - small zip-lock bags of condoms and lubricants, which include pamphlets explaining how to work safely, and how to deal with an attacker (the high heel raking down the shin is a wince-worthy image).
"After decriminalisation, people thought the 'problem' would go indoors," Pickering says. "But most of the people on the streets can't get hired in a brothel because they have tattoos or missing teeth or they are transgender.
"This community is on the fringes of society. Society looks on them as outcasts but they are the most vulnerable people in our community and we need to look after them."
At first glance, Alexis - a transgender worker I meet near the steps of a single-storey office building - doesn't exactly look vulnerable. Well-built enough to step into a lineout, she projects an air of hard-won seniority as she talks of life on the street.
Many of her co-workers resort to sex work because it's the only way to ensure their families are fed, she explains.
"A lot of girls like their fries [meth or P]," she says, swigging on a can. "Not me; I just drink now. You've got to be on something, whether it's alcohol or green or fries. They are just trying to get in and out of cars quickly to get money to pay their bills."
The workers look after each other, she explains, because "a lot of them don't have a family connection. This is their family".
Elsewhere and later, Pickering listens to another worker's housing woes - her leaseholding grandmother has died and her mother earns too much to be allowed to stay in their state rental. Pickering scribbles notes for passing on to the Mission staff.
In Manurewa, she warns a newcomer against undercharging because of the danger from rivals angry that she's driving prices down. Across the street, she stands guard while a flamboyantly tipsy woman has her details taken by police.
Taylor, a veteran of 15 years in hospitality, who only works to be able to "afford the things I like" gives Pickering and her colleagues high praise. "She's a friend and a confidante," Taylor says.
"If you're having problems she'll find a solution. A lot of people look down on us, think they're better than us. You don't get that with Annah."
