For trans film-maker Kristen Lovell, her new documentary The Stroll – co-directed with another trans film-maker, Zackary Drucker, and premiering on HBO this week – was about including an ignored chapter of trans history, one that she herself lived. Young, Black and trans in 90s New York, Lovell was fired from her job when she began to live her truth and was forced to sustain herself via sex work. The Stroll is a testament to what she went through just to be herself and the stories of so many other women like her that she met along the way.

“It was just time to tell this story,” Lovell told me. “There was a void, a generational void, where we went from the likes of Sylvia Rivera and Marsha P Johnson to this new generation that’s coming up and fighting again for trans rights, and there’s a generational gap. Trans history is something that’s not taught in schools, so the new generation really didn’t have an understanding of all this stuff.”

Drucker added that, “because of the dominance of the trans sex worker trope, there was this impulse to focus on other representation of trans people. That led to this erasing of trans sex work from our history. Trans people have always survived through the centuries as sex workers and in underground economies. It’s overdue for us to highlight and foreground the stories of trans sex workers.”

The Stroll tells the story of New York’s west 14th Street, once a central hub of sex work and slaughterhouses, two economies that have been displaced as the city’s so-called Meatpacking District has been transformed through gentrification, now sporting high-end restaurants, boutiques, the High Line and the Whitney museum. With lots of archival footage, the movie brings this lost world to life, centering a subset of the trans community that is often left out.

A veteran artist and documentarian focusing on transgender women, Drucker was the ideal collaborator for Lovell, who makes her directorial debut with The Stroll. Although Lovell had been using a video camera to document other trans women on The Stroll since about age 19, she wanted someone who could help her harness the archive of footage she had been collecting for years. “Being a first-time director I needed someone who was more experienced,” she said. “I knew Zachary would be the perfect fit.” Drucker added that from the very first meeting she felt a kinship, saying: “We Zoomed in December 2020, and I just had this fluttery feeling of fate, meeting Kristen. I’ll never forget it. This was a story that wanted to come into the world. There was such harmony behind the scenes.”

The movie is part oral history, granting many of the surviving sex workers the space to tell their stories of how they managed to oversee complicated medical transitions while navigating the twin dangers of potentially dangerous clients and police officers. As The Stroll documents, many of these women ended up serving lengthy prison sentences at Rikers Island for little more than trying to subsist in the gray economy, and many of them died before they had the chance to tell their stories to Lovell and Drucker.

“From back then, in the 80s, let’s say there was 1,000 girls; today living from that era, it might be five,” said Egyptt, a former sex worker, in The Stroll. Her testimony was followed by Nicole, another sex worker, who said, “If you made it to live beyond [40 years of age], you are tremendously blessed and you have changed the dynamics of the system.”

Starting in the 80s and 90s, and moving forward through the decades, The Stroll pauses on the murder of Amanda Milan, a Black transgender sex worker who was stabbed to death in 2000 in a hate crime in the early morning hours in Times Square. While the New York Times’s three-sentence notice of the event typified the muted response to the murder, describing Milan as “A man [who] was fatally stabbed in midtown Manhattan yesterday after a dispute with two other men … dressed in women’s clothing,” the murder became a rallying call among trans people seeking better inclusion into the LGBTQ+ community.

“It really was a turning point in the trans community for mobilizing,” said Drucker. “It’s one of the touchpoints in our community.” Lovell added that, “I tell young people today that we’re more mobilized than we have ever been in history. We’re all so much more aware of each other – we’re communicating and sharing our experiences now. So it was a big thing, it was a really big thing.”

The Stroll offers Milan the dignity and empathy that she did not receive from the media at the time, while also focusing on the contrasting responses to her murder and that of Matthew Shepard. As The Stroll attests, while Shepard’s vigil received an outpouring of support from New Yorkers of all kinds – as well as an address from then-president Bill Clinton – Milan was jeered at while she was being murdered and was only commemorated by other women like her. The film features archival footage of an aghast Rivera lamenting that only 200 people showed up to honor Milan’s death.

“A lot of these women’s stories are my stories,” said Lovell. “I really knew these women. I’ve experienced a lot of things that they all experienced. I had been attacked a few times, with razors to my throat, or being locked in a car with a knife to my stomach. To know that the same place that Amanda Milan had walked, I had been there, it could have been any of us. She was stabbed, and no one wanted to help her because she was trans. It woke me up as a young trans person.”

As demonstrated by the film’s documentation of Milan’s murder, one of The Stroll’s strengths is how it helps audiences understand the indignities placed upon trans people, even from other members of the LGBTQ+ community. At one point the film shows a segment filmed by an up-and-coming RuPaul, as he joyfully skips along The Stroll with a film crew, saying: “I asked some of the girls – boys – girls, whatever, if I could take a look inside of their world!” chirpily laughing at his own degrading jokes. For Lovell and Drucker, unearthing that bit of trans history was surprising, even to them.

“I think it just goes back to RuPaul’s claim that, when he has been held to account for excluding trans people in the past, the claim is always that ‘we were all in it together back in the day, we all come from the same place’,” said Drucker. “And that clip just highlights that that is not true. To be able to take the drag off is a privileged existence, whereas when you’re committing full-time to living a trans life, you – especially back then – paid consequences.”

The film also documents how the nature of sex work and the Meatpacking District have changed over time. Due to the twinned influences of 9/11 – which in effect shut down The Stroll for some time – and the rise of the internet, sex work happened more and more online than on the street. Michael Bloomberg’s subsequent institution of tough-on-crime policies – epitomized by stop-and-frisk, which in effect criminalized simply walking while trans – further led to the transformation of the Meatpacking District.

The Stroll ends on a high note with footage of Ceyenne Doroshow, founder of Glits Ink, addressing a crowd of 15,000 in June 2020, celebrating the lives of Black trans people and announcing that Glits’s fundraiser to build and own housing for Black trans people had raised nearly $1m in just three days. The film is also a celebration of the long-overdue arrival of Lovell as a trans film-maker and documentarian, one who will hopefully have many, many more stories to tell. “It’s been a long journey,” she said, “and so we finally made it to this point, which is still a little bit of a surprise.”

• The Stroll is available on HBO and Max from 21 June and in the UK at a later date