Penny Barber Turns 40: Inside Her Birthday Bash With Ryan Keely

Penny Barber Turns 40: Inside Her Birthday Bash With Ryan Keely

Penny Barber turns 40 years old this month, so the veteran performer decided to celebrate in style with a very special birthday bash alongside her best friend, Ryan Keely.

“I feel like 40 is a big birthday, and a big MILF birthday especially,” Barber tells XBIZ.

While many people dread turning 40, Barber says she’s been looking forward to it for quite a while.

“Originally, what I really wanted to do was have a gangbang with guys who were literally half my age, all 20-year-olds,” she says. “Unfortunately, there’s not a lot of those.”

Barber decided to pivot after chatting with friend and fellow performer Keely.

“I get along with her really well, and she and I had been talking about doing this big, crazy MILF Hotel thing — a very elaborate feature,” she explains. “I’ve been pitching around to companies a little bit more these days, and as much as I really would have loved to do that big, insane idea with Ryan, I was like, ‘They're probably not going to give us the $50,000 to $100,000 that this is going to cost.’ So I really pared it down and just started making cuts.”

Barber began chipping away at the script and budget while still keeping her own pleasure in mind — and never losing sight of celebrating a milestone.

“I was like, ‘What’s the closest I can get to that idea where I'm still going to enjoy myself, and it's going to be something that Ryan will still be excited to do, and I also get to fuck the guys who I want to fuck?’” she recalls. “So we kept the hotel setting and just leaned into Ryan’s really big personality and my more reserved personality. I really like being coerced into things, so she’s sort of corrupting me and getting me to open up for my 40th birthday.”

In keeping with her personal brand and flavor, Barber also wanted it to be taboo.

“Axl Hayes plays Ryan's stepson, and he’s gorgeous, just so hot,” she enthuses. “Unfortunately, he had the audacity to turn 21 before I turned 40. So I didn’t even get one 20-year-old, though I did get a 21-year-old, so it’s worked out pretty good. It was a compromise, but I'm so happy.”

Barber also gushes over working with Max Fills, who plays her stepson.

“He’s just my absolute favorite,” she says. “I love him. He fucks so well. Seriously, he’s the best I've ever had in my life, and he’s really sweet too. He really wants to be on set, he wants to do well, and he works hard.”

When Barber pitched her idea to Adult Time, she didn’t show up empty-handed.

“Whenever I pitch something, I put together a full video presentation with custom graphics and everything,” she shares. “And they went for it, which I was very happy about. Bree Mills was a lot of help in getting things started.”

Since Barber would be on camera, her friends Siouxsie Q and Michael Vegas stepped in to help her direct.

“We did our best with monitors and everything, but I couldn’t always see the shots,” she says. “I’m still baby directing, so I was trying to talk to Michael about lens choices while also trying to be onscreen, but when you’re on camera, you’ve got to focus on the performance.”

The premise involves Barber and Keely taking a special trip for Barber's 40th birthday.

“She's like, 'We're going to have this special weekend, go clubbing and pick up some younger guys,'” Barber teases. “And I'm like, 'Oh gosh, I really don't know. I don't usually do that sort of thing. What would my husband say?' And she's like, 'Well, I bought you this really slutty dress and you're going to wear it.' And I capitulate eventually — but then, of course, as soon as we get outside, who do we see off campus when they're not supposed to be, and sneaking off to go have their own little wild weekend? Our stepsons.

“So there's a moment where Max — he takes after me, so he's very demure — looks up, and all of a sudden, his mom is there dressed like a slut with Mrs. Ryan Keely, who is also dressed like a slut,” she elaborates. “And he's embarrassed, and I'm embarrassed, so we both run off. Then Ryan is like, 'I'm going to go calm your stepson down, you just stay here,' but then through the wall, I can hear them fucking.”

To capture the feeling she had in mind, Barber tried using some slow-motion shots.

“I really like that moment where you come in and it's like the world has slowed down,” she explains. “You're seeing this beautiful but also kind of terrible thing happening, and you're into it, and you're questioning yourself. The camera that we were using only had the capacity to do 40 frames per second when I really wanted 120, so I'm not sure quite how floaty and dreamy it's going to look, but I really hope that we captured that moment because that's what I think is fun and hot and dirty: just coming in and seeing Max's perfect, beautiful cock repeatedly slamming into Ryan Keely's absolutely gorgeous mouth.

“I'm very grateful to Adult Time for bankrolling it,” Barber adds. “And the sex was really fucking great!”

She credits DP Joel Sinclair as another key collaborator.

“I love Joel,” says Barber. “He's really cool. He's a second-generation pornographer, as I think his parents were distributors. What I really like about working with Michael and Siouxsie and their crew is that everybody wants to be there, and they want to do their absolute best. Joel just really embodies that.

“As the DP, he'll do anything to make the shot good,” she marvels. “I've seen him climb up on things and hold things up with his arms, so he's very physical and he always has good suggestions. He'll take little shots to show me afterwards. I think we first met on a Vixen set, but he's worked for everybody and I love working with him.”

Barber notes that Keely picked out the wardrobe.

“Costumes are her thing, because she has so much stuff!” Barber laughs. “I'm really glad she was involved because she also wants to make each production the best it possibly can be.”

“She wore this beautiful sparkly thing, and I had just got this really slutty little white dress sent to me from a custom order, so I just wore that,” she adds. “It's very tight.”

In order to properly celebrate the release of her birthday video and promote it online, Barber made sure to take a bunch of BTS videos on her phone.

“I talked to both Lauren Phillips and Ariel Demure, who have directed for Adult Time,” she says. “They both said, 'You're going to have to promote it, and that's going to be on you. So have your freaking phone in your hands and record things!' Which I did. So I'm going to be releasing a lot of stuff on social media, and maybe I'll try to do a watch-along or something with my fans.”

Barber's husband is a photographer and has helped her shoot in the past, though he wasn't involved in this shoot.

“He decided to go back and be a 'normie' and work in corporate America again,” she laughs. “But he and I are both into film gear and we've been together for a very long time. So we both buy each other film gear, and I'm never sure if I bought something for him or if he bought it for me. I have this really nice all-glass 85 mm lens that I don't use enough, and I have this 100 mm macro lens — that was a good present, though I'm not sure if it was for my birthday or for Christmas... or if I bought it for him! Either way, I really love it.”

While Barber counts herself a movie buff, she says she doesn't watch a lot of new movies.

“Lately, I've started getting into dark fantasy films from Eastern Europe,” she says. “‘V’ is good. 'The Kingdom of Crooked Mirrors' is good. 'Rusland and Ludmila' was great. Weird, but great. I highly recommend that one. And I've got this 1972 version of 'The Little Mermaid' on my docket, which I'm really looking forward to watching.”

At 40, Barber remains in great shape, which she attributes to calisthenics and bodyweight exercises, as well as eating a lot of protein.

She also keeps her social media diet manageable, sticking to OnlyFans and her own website, Pampered Penny, so that fans don't have to track her across a dozen different platforms.

“I like to keep it easy and keep it tight,” she explains.

Barber plans to spend her birthday with fellow performer Little Puck.

“I started seeing her not too long ago, so I'm sort of focusing on my relationship with her right now,” she reveals. “I just want to do something low-key, but she keeps saying we're going to do something, and I know she has something special planned. We'll probably just have dinner and then go screw, but maybe she can talk her boyfriend into doing pushups while I watch or something. That would be fun!”

Barber teases that she and Little Puck are making plans for a “really big, crazy shoot,” but she does not want to reveal any details just yet.

“It's very ambitious and we don't want to jinx it,” she says.

In the meantime, Barber shares, she also would not say no to a “princess cake” for her 40th.

“I want the green fondant icing all over it,” she confides. “And raspberry jelly in there.”

Looking back on past milestones, Barber recalls that her 21st birthday was a lot of fun.

“Or at least, what I can remember of it,” she says. “To be honest, I'm a little bit of a nerd. I remember one year, we played the role-playing game 7th Sea, which is like Dungeons & Dragons but with pirates, so it's very swashbuckly and it uses a d10 system instead of a d20 system. We played that, and then we did karaoke, and I threw up in the sink.”

Looking ahead to the next milestone, Barber promises to do a special shoot for her 50th birthday — ideally involving a bunch of 25-year-olds.

“If I put my mind to it, I think I could do it,” she vows. “I'm certainly going to try.”

What's clear is that Barber shows no signs of slowing down and plans to continue performing for as long as possible.

“I've been doing it since 2003, and I don't know why I would ever stop doing this,” she affirms. “I mean, something terrible might happen to me where I can't do it anymore. But barring that, I'd love to do this forever.”

Surely, her millions of fans hope that her birthday wish comes true.

All photos courtesy of Modest Pup and Michael Vegas.

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