Ten-year-old Jack Khan feels more comfortable in his own skin when he's wearing a dress.
His mum worries that his dressing up may cause her little boy some strange stares, or worse - make him the subject of teasing and judgement - but she hopes he will be shown love and acceptance as he finds his way in the world.
"I love to dress up and wear dresses, I feel more comfortable when I dress up," the Mt Ousley Public School year five student told the Mercury.
"It gives me more confidence. I really like light pink dresses. And I'm better than my mum and sister at walking in my heels," he said.
"It's so much fun. I think I'm a better singer when I'm dressed up. I just love it. It makes me happy."
Jack's mum Ally said her boy could sing before he could talk.
"You'd take him shopping and he would let out these enormous opera singing notes, quite embarrassing actually, not believing that sound could come from a little kid," she said.
"He does drama too and loves musical theatre.
"As far as the dressing up is concerned, from a very young age he was always into his sister's things.
"And then he just became a little bit more."
Ally said her son doesn't want to be a girl, he just likes to dress up loves clothes and makeup.
"To be honest there have never been any challenges, he's such a well behaved kid, my only fear is always going to be if he starts getting bullied or teased which he never has.
"I'm concerned about high school. His dream would be Wollongong High, I think he would fit in better in that community.
"I worry how he will be accepted by other. But for now in primary, Mt Ousley is the most beautiful, inclusive school."
His sister Maggie, 15, and brother Hyder, 13, are the little performer's biggest fans.
"He idolises his big sister, she's into drama too. His brother is a real boy's boy but so supportive of Jack too.
Jack first went out in full drag around December to a show at Bulli, where he met well-known Wollongong drag queen Roxee Horror.
"From the minute he met Roxee Horror he said 'this is what I want to do, this is what I want'.
"From a mum's point of view him meeting Roxee was wonderful.
"While I'm happy for him to be whoever and whatever he is and support him, having Roxee in his life and the whole drag community behind him is fantastic. Roxee has taken him under his wing.
"It's all new for me. I just want him to be happy and love seeing him doing something he is passionate about.".
When Jack dresses in full drag he becomes Jackaranda.
"My sister and I were having some fun brainstorming and we came up with that name, which I love," Jack said.
Adam Larkhan, aka Roxee Horror, recalls meeting Jack in December last year.
"The first time I ever saw Jack I was walking back stage they were talking about this young drag queen.
"I thought it was a young glammed-up girl.
"I stopped in my tracks I was blown away that there was a passable drag queen of Jack's age. Jack got me the first time I saw him.
"I bumped into him and his family outside the venue we got a few photos and had a chat about drag and what got him into it.
"We found each other on social media and have been keeping in contact that way and I offered to help with some makeup tips, jewellery and dresses," Adam said.
"I've helped him the best I can to mentor him to shape himself into the drag queen he wants to be."
Adam said he was shocked to see a drag queen so young.
"I thought 15 was the youngest, I didn't really think there were younger queens than that but when I saw him it made me so happy because we are living in a time now that someone Jack's age can feel the way he wants to feel and be the way he wants to with no discrimination from people who love him."
Adam is also wary about the broader community's response to Jack but says the boy is "nothing but a ray of sunshine".
He hopes he will be embraced and is encouraged by Wollongong's response to his own show as Miss Roxee at the controversial and much-publicised Drag Storytime at Wollongong Library last year.
Roxee left Wollongong library feeling like a rock star after a crowd of 300 people turned out for the first-of-its-kind event in Wollongong.
"The positive far outweighs the negative so I just hope that keeps growing and people become more and more accepting," Adam said.
"I see Jack's transformation when he changes to Jackaranda.
"It's more than the clothes.
"It's still Jack but it's like an extreme heightened version.
"Like when I become Roxee, he feels more comfortable in his own skin ... which is ironic because he's in a dress."
Jack will get a special treat this weekend, meeting one of the country's most famous, long-time drag queens in Carlotta.
The cabaret performer and TV celebrity who inspired the making of the hit movie Priscilla Queen of the Desert, will be performing at the Spiegeltent.
The minute she heard about Jack she was keen to arrange a meeting.
You can catch Roxee and Jackaranda live on stage on May 17 at Shellharbour Youth Centre where they will be performing in Cherry Ripe's Drag through the Decades production.
Jackaranda will also be special guest at Roxee Horror's Drag Extravaganza at the Music Lounge on July 13.
"I'm so excited to have Jackaranda join the cast for the drag extravaganza," Roxee said.
"Watching how much he has grown in a few short months has been amazing.
"Wollongong's drag scene has a lot to offer and this is just the beginning for Jackaranda.
"It's going to be fantastic to perform alongside Jackaranda and watch him in all his glory."
You can watch Jack's career evolve by checking him out on his instagram page Jackaranda which is closely monitored by his mum.