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Penny Barber Takes the Shot for MILFY - Image 01 (February 12, 2026)

Penny Barber Takes the Shot for MILFY

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Kinky Mommy Dom, Strap-on Boss, and multi-award-winning MILF Penny Barber stars with Rissa May and Dan Damage in a new release for MILFY.
Directed by Derek Dozer, “Seductive MILF Penny Shares a Cock with Rissa” opens with fashion photographer Penny Barber doing a shoot with model Rissa May, while assistant Dan Damage helps out. Seeing the way Rissa is looking at Dan, Penny pulls her aside to tell her to go for it. Wanting to help, Penny takes the photoshoot in a new, sexy direction, and soon all three of them are on the bed with their clothes off. Rissa and Penny give Dan a double BJ before Penny climbs aboard to ride Dan in cowgirl. Next, it’s Rissa’s turn to ride Dan, while Penny licks her nipples. Dan does Penny in doggy and missionary before side fucking Rissa while Penny looks on. Finally, Penny and Rissa take turns again riding Dan, before getting down on their knees so he can finish in their mouths.
“I always know when I shoot for Vixen and Derek that it’s going to be a special scene, and it felt so on brand for everyone that I got to play a sexy Annie Leibovitz-type, and getting to do that with two of the hottest people I know in Rissa and Dan just made it that much better,” says Penny Barber.
ABOUT PENNY BARBER
Entrepreneur Penny Barber wears many hats, from producer/director to performer to storyteller/filmmaker to author and beyond. She’s known for playing the busty, glasses-wearing Taboo MILF who likes to sling verbal humiliation and Kinky Mommy Dom.
In her 10+ years in the industry, Penny has made countless clips, authored two books on age play, and shot with various independent clip producers. She’s also worked with Deeper, Brazzers, Blacked, Slayed, MILFY, Blacked Raw, Girlsway, Pure Taboo, Team Skeet, Elegant Angel, Digital Playground, Sweetheart Video, Family Sinners, Transsensual, Transfixed, Kink.com, Reality Kings, Nubiles, Deep Lush, AllHerLuv, Missa X, and many more. In January of 2022, she was crowned MYLF of the Month (aka MOM) by MYLF.com. She’s entering film festivals and making professional cinematic pieces when not shooting for top-shelf studios.
Penny scored the Hustler cover, 10-page feature, an exclusive interview in the April 2024 issue, a 12-page piece in XBIZ’s X3 magazine, and the cover and multi-page layout in the January 2023 issue of Kink Queens. She’s also been interviewed by mainstream media outlets like Vice and The Daily Beast. She’s already won multiple impressive awards, which include MILF Performer of the Year from the AVN Awards, Best MILF Performer from the NightMoves Awards, MILF Performer of the Year from the XRCOs, MILF Performer of the Year and Best Sex Scene – All-Girl from the XMAs (twice), MILF Performer of the Year from the Urban X Awards, Best MILF Clip Artist from the XMA Creator Awards, Fan Favorite Fandom Video from the Bazowie! Awards, and Best Scene in the Fleshbot Awards. Penny has also scored multiple nominations from the XMA, XMA Creator, AVN, Pornhub, Bazowie! GayVNs, Urban X, Cammy, Fleshbot, XCritic, TEAs, and Inked Awards.
Stay in the know about everything in her world by following her Twitter/X @pamperedpenny and TikTok @misspennybarber.

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