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. 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 when Max — he takes after me, so he's very demure — looks up, and all of a sudden, his stepmom 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 when 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,” Barber notes. “So I'm not quite sure 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.”

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.”

Looking ahead to the next milestone, Barber promises to do a special shoot for her 50th birthday, ideally involving — you guessed it — 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 legion of fans hope that particular wish comes true.

All photos courtesy of Modest Pup and Michael Vegas.

Related:  

Copyright © 2025 Adnet Media. All Rights Reserved. XBIZ is a trademark of Adnet Media.
Reproduction in whole or in part in any form or medium without express written permission is prohibited.

More News

Jade Greene Makes Her Reality Kings Debut

Jade Greene has made her Reality Kings debut alongside multi-XMAs winner Mick Blue in "Ski Boat Skeet."

Vicki Chase Stars in Dorcel's 'M.I.L.F.S. Vol. 2'

Vicki Chase headlines the latest feature from Dorcel, titled “M.I.L.F.S. Vol. 2.”

Anastasia Doll Headlines 'All Girl Sex Addict' From Harmony

Anastasia Doll stars in the latest title from Harmony Films, “All Girl Sex Addict.”

Blake Blossom, Madison Wilde Topline 'The Art of Kissing 4' From Sweetheart Video

Blake Blossom and Madison Wilde headline the fourth volume of “The Art of Kissing” from Mile High Media studio imprint Sweetheart Video.

Chloe Amour Toplines Latest From Tushy

Chloe Amour stars with Dante Colle in the latest release from Vixen Media Group (VMG) studio imprint Tushy.

Jade Venus Fronts 'Trans Cheerleaders 2' From GenderX

Jade Venus stars with Evie Christian and Sage Roux in the second volume of GenderX Films' "Trans Cheerleaders," directed by Jim Powers.

Leilani Li Stars in Latest From Transfixed

Leilani Li stars with Avery Jane and reigning XMAs Trans Performer of the Year Ariel Demure in the latest release from Transfixed, titled "Bolstered and Pampered."

Ember Snow, Teal Conrad Topline 'Lesbian Neighbor Affairs 3'

Ember Snow and Teal Conrad headline “Lesbian Neighbor Affairs 3” from Girlfriends Films.

Chloe Amour Fronts Latest From New Sensations

Chloe Amour stars with Milan Ponjevic in the latest release from New Sensations, titled "He’s in Charge."

Octavia Red Stars in Latest From Deeper

Octavia Red stars with Manuel Ferrera in the latest release from Vixen Media Group studio imprint Deeper, titled “She Done Him Wrong.”

Show More
OSZAR »