Comedian Derek Furtado brings the audience along as he learns to parent a transgender teen

Derek Furtado has performed in front of LGBTQ audiences before, but his comedy set at Laguna Beach’s Main Street Bar & Cabaret was his first at a gay bar. So he played up his own confusion and naivete.

“I was just making fun of the whole thing, letting them know that I was soaking it in,” says Furtado. “There was a sign on the wall that had the letters M and S [for Main Street], and I was like, ‘Well, I know that doesn’t stand for menstrual cycle.’ ”

Furtado lives in Rhode Island, but he recently performed nine shows in five days at the Orange County Comedy Festival, which ran from Nov. 14 to Dec. 16.

The inaugural festival gave Furtado, 35, an excuse to reunite with old friends from Irvine’s Rancho San Joaquin Middle School, where he was voted “funniest,” and University High School.

After a few more jokes, he wanted to let the Laguna audience know that he might look like a fish out of water, but that he is the parent of a transgender boy.

Every day, he wears a gay pride rainbow paracord bracelet given to him after a show by a couple of lesbians after he discussed his teen.

“I wasn’t making it a bit,” he says. “It’s just that there’s a lot of honesty in comedy, and every once in a while, I found it therapeutic to talk about. When they gave [the bracelet] to me, it was serious for me. I thought, I’m going to wear this. I want to wear it for my kid to see. And maybe it can open up conversations.”

Furtado remembers the day that his teenager came out to him as transgender. Furtado was sitting in the same living room in which he confessed to his own parents in 2001 that his high school girlfriend was pregnant.

So even though he was caught off guard by his child’s tearful confession, he remembers wanting him to know that he was — and is — OK with it.

“The first thing I said was, ‘Honey, do you understand how much money you’re saving me right now?’ ” he says. “ ‘Do you know how much prom dresses and wedding dresses are? Thank you so much. This is such a relief … financially.’ ”

They shared a few laughs and talked it through. It wasn’t until after Furtado dropped his teenager off at his mother’s house that he was overcome.

“I just started bawling,” says Furtado, “because I was watching my little girl walk away from me for the last time. I wasn’t mad, but it was just my own selfish sadness. I don’t feel guilty about it, but I just had to let that go, and it was sad. It was going to be different from now on.”

Derek Furtado is a self-defined “dirty comedian.” He tells provocative jokes about gender, race and sexuality.

He also often tells stories about his kid. He has a joke about buying his young daughter earrings and worrying that she’ll attract attention from leering men. He has another about being paranoid that he will one day call his daughter while she’s having sex. These are jokes that he recognizes have a shelf life.

All of his jokes come from a positive place, he insists, but he’s retired certain bits — including one that used a hand gesture and a slur in how to tell if someone was gay — from his 13 years of stand-up because they now make him uncomfortable.

“So now I know I not only want to be positive, but also aware of certain words or things that can trigger people; otherwise that’s not the point of what I’m trying to say,” he says. “The point of the joke was in the subtleties that I think are funny, but people won’t be open to the subtleties if they’re offended by a word … Is my awareness heightened now because of my son? Of course, 100%.”

Like many comedians, he believes in pushing boundaries to find humor. But sometimes to find the line, he explains, comedians need to cross it.

“Then you learn the limit and say, ‘OK I can work from there,’ ” he says. “I feel like it’s not malicious, but people take such offense to things, and not even just as an entertainer, but when it comes to kids dealing with families who don’t really understand them — or maybe not even realizing they’re saying something dumb at Thanksgiving dinner, not knowing the kid’s situation. [The family members are] not always trying to be mean about it. They know their own ways, but if there’s something that’s close to home and they do care about somebody, they might look at things a little differently.”

Furtado was performing at a college about a year ago when he realized one of the students in the crowd was gay. He started opening up to the audience about his own experience with his transgender teenager, now 17.

“I wanted to let them know, ‘Listen, I don’t get everything, but I’m trying,’ ” he says. “ ‘And I think a lot of parents are trying as well, so you guys have to be patient with us. And just ’cause there’s a reluctance doesn’t mean the answer is no. You just gotta be able to teach us as we go along.’ ”

Furtado played football in high school, but he also performed in school plays, including a lead role in “Fiddler on the Roof.” He once encouraged his teammates to sing ’N Sync’s “God Must Have Spent A Little More Time On You” for a talent show.

Being in both sports and drama was more common in Southern California, he says, but once he moved back to the East Coast to complete high school, classmates called him “gay.” He tried to use humor to enlighten ignorant classmates.

The transgender experience is less familiar to him, and he understands that this time he’s the one who needs an education.

“People are so willing to scold those who are ignorant to things,” says Furtado, “but the greatest way to deal with ignorance is through enlightenment. For me, that’s one of the greatest feelings in life, because you not only gain knowledge but you gain empathy.”

Furtado is open about the fact that he’s unsure of the best way to guide his son.

“Do I drag my feet sometimes? Sure,” he says. “And my kid’s like — let’s move forward [with therapy and testosterone] … because my kid knows how he feels, and I get that. But I just remind my kid that me going at the pace I am is coming from a good place and not a bad place because it scares me.

“The world sucks and people are really mean. So maybe it’s more of a protection thing that I drag my feet a little bit. Maybe a little bit of selfishness. I just want to make sure as a parent, I’m doing the right thing. People dealing with a loved one who is transgender, they’re just taking baby steps and soaking it all in.”