In her heyday, Jennifer Bobbi was Long Island’s Tupperware queen, selling hundreds of thousands of dollars’ worth of kitchenware and earning herself a six-figure salary.
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For about a decade in New York, she hosted parties and ran her business as Aunt Barbara, a drag queen whose brash attitude and sassy comebacks were part of her act.
Bobbi was living as a man at the time, and portraying Aunt Barbara allowed her to dress up in 1960s-era dresses and a black bob wig to host her Tupperware parties, to the delight of her clients, she said.
“I believe that most people thought it was a great, fun thing to do in their house,” Bobbi told ABC News. “It was a comedy show, but it was a comedy show in their minds because it was a man dressed as a woman playing a character.”
But she didn’t want to just act like her female character; she said that from a very young age, she knew she was a woman.
“I held it inside through my teenage years into my 20s, and finally, at one point when I think my parents could not figure me out, my mother sat down with me, and she said, ‘We know that you’re gay. We know that you’re homosexual,’” Bobbi said. “What I wanted to say was, ‘Well, it’s half the story. It’s half the story because I’m attracted to men and I’m biologically and physically a male, but intuitively, mentally, organically, I’m a female. And I have been my whole life.’”
When Bobbi came out as a trans woman on April 1, 2015, she said, she was surprised by how some of her clients suddenly treated her.
“I considered Aunt Barbara just a character of who I am. It’s a part of who I am. And I guess I thought that, well, they accept Aunt Barbara. Why wouldn’t they accept me? I’m just the person who’s behind Aunt Barbara,” said Bobbi, 48.
But after her transition, people began canceling their Tupperware parties, she said, and her business suffered.
“I do think that my transition was a major contributing factor to the decline in my business,” Bobbi said. “I noticed that some people don’t understand the difference between what they perceived as a drag queen or as being transgender or a cross-dresser.”
Bobbi is far from alone. Advocacy groups have released studies showing that the unemployment rate is far higher than average for transgender individuals, though no government agency has released similar data.
Even though societal awareness about the issues trans people face has grown in recent years and a number of high-profile celebrities have opened up about their transitions, advocates say there is long way to go in the fight for true equality in the workplace. On Oct. 5, Attorney General Jeff Sessions announced his decision to strip trans individuals of protections against discrimination in the workplace under the Civil Rights Act. And in July, President Trump said in a tweet that trans people will not be allowed to serve “in any capacity” in the U.S. military; the matter is currently under Defense Department review.
For Bobbi, like many other trans people, living as her true self came with a steep financial cost.
At her sales peak in 2013, Bobbi said, she was so busy, she “couldn’t handle the bookings. I could have done two or three parties a day.”
“I earned a Ford Mustang or a cash bonus. I took the cash bonus and bought a Cadillac. I earned a trip to Hawaii, trips to Florida, trips to New Orleans,” she said.
She sold hundreds of thousands of dollars’ worth of Tupperware, and while she wouldn’t specify the number, Bobbi told ABC News that her take-home pay at the time was six figures.
Fast-forward four years, and Bobbi was facing bankruptcy. She said that after she came out and began taking hormones as part of her transition, her business dried up.
“It’s funny — it’s all fun and games when you’re perceived as a man dressing as a woman but you don’t want to be a woman,” she said. “But when you’re biologically a man and internally and innately you’re a woman, then it’s not so funny anymore.”
She said people didn’t want to see that she was “a person with a struggle”; they wanted to view her merely as a funny character.
“Aunt Barbara’s all about helping people forget their problems. They don’t want Aunt Barbara to come to their house with a problem,” Bobbi added.
Omar Gonzalez-Pagan, a staff attorney at Lambda Legal, an LGBTQ advocacy group, said Bobbi’s experience is troubling but common.
“Here what we can see is the pervasive discrimination faced by transgender people day to day in their interactions as they move about society,” Gonzalez-Pagan told ABC News.
The paradox of being accepted and celebrated as a man in drag and rejected as a trans woman “shows some of the progress that has been made and some of the shortfalls that we have encountered,” he said.
Gonzalez-Pagan said that it is important for people to understand that people of any gender can perform drag, which is viewed within the LGBTQ community as a historic art form, and while transgender individuals have long been pioneers in the field, they are not the only ones who participate.
Bobbi went from local celebrity to someone struggling to make ends meet. She had to change many parts of her lifestyle, downsizing apartments and eventually moving in with a longtime friend in another part of Long Island.
"I was able to have a good standard of living, and that went away, just slowly went away, little by little. Things got harder,” she said. “Eventually, I wasn’t able to pay for basic necessities.”
Now Bobbi is working as an executive assistant at a nonprofit and as an aide to an individual with disabilities. She said she earns a small fraction of what she was making before she began her transition. Her bankruptcy was discharged as of early June, she said.
She said she still performs as Aunt Barbara, though rarely, and is pursuing an acting career in local theater.
Bobbi said that she didn’t receive overly negative comments on her coming-out Facebook post. But she said she has experienced some instances of strangers looking at her curiously and has been verbally harassed by strangers.
She added that while her sisters have been largely supportive, “My friends have really been my family.”
“I didn’t ask for this. No person that’s transgender asks to be transgender. This is not an easy route,” Bobbi said.
“I would love to continue being who everyone wants me to be or needs me to be or thought I was, but I can’t,” Bobbi said. “I have to be true to myself. I have to be who I am. I’m the one who’s going to be living the rest of my life. I have to. I have to be happy with myself. I have to feel whole. I have to feel right, and I’ve never felt right. I finally am feeling right. That’s huge.”
ABC News’ Kaelyn Forde, Jessica Hopper and Michael Huberman contributed to this report.