Family Roleplay
Favorite54 Matches Found
Free Use Family Secrets (2023)
- Studio: Crave Media
- Starring: Alice Pink, Dixie Lynn, Kenna James, Kit Mercer, Kylie Kingston, Mia Kay, Savannah Sixx, Johnny Castle, Johnny Love, Rion King
- Movie Synopsis: Freeuse is a fetish where women are made sexually available to men anytime, any place, anywhere. In this fantasy world, women allow men to do wahtever they want, ignoring common standards, and happily... Read more
Daughter Swap 10 (2021)
- Studio: Team Skeet
- Starring: Aliya Brynn, Charlotte Sins, Diana Grace, Jenna J. Ross, Kenna James, Laney Grey, Natalie Knight, Paisley Bennett
- Movie Synopsis: Young and innocent Jenna Ross and Kenna James are excited to hang out with a couple of guys they met online, but their nosy stepdads are not thrilled about it. Especially when Kenna lets it slip that ... Read more
Mother Daughter Thing 3, A (2015)
- Studio: Digital Sin
- Starring: Dana Vespoli, Jelena Jensen, Karlie Montana, Kendra James, Kenna James, Marley Brinx, Raven Rockette, Tanya Tate
- Movie Synopsis: Frustrated by the feminist movement and women's fears about good old fashioned, lesbian sex, Kendra sets out to give her stepdaughter, Karlie, some hands-on instruction. Passions ignite after Dana adm... Read more
Lesbian Stepmother 4 (2018)
- Studio: Sweetheart Video
- Starring: Amara Romani, Cherie DeVille, Ivy Wolfe, Kenna James, Mindi Mink, Raven Hart, Sarah Vandella, Shyla Jennings
- Movie Synopsis: Sweetheart Video's popular series is back with more unruly stepdaughters and the lesbian stepmothers that love to seduce them! Enjoy four taboo stepmom fantasies, from an out of control stepdaughter i... Read more
My Dad, Your Dad Vol. 2 (2018)
- Studio: Sweet Sinner
- Starring: Britney Light, Devon Green, Kenna James, Maya Kendrick, Jay Smooth, Ramon Nomar, Ryan Driller, Steve Holmes, Tommy Gunn
- Movie Synopsis: Kenna's close relationship with her Dad has left her with a burning desire to be with an older man just like him. When she stumbles across a site called DilfFantasies.com with stories written by women... Read more
Who's Your Stepdaddy (2018)
- Studio: Zero Tolerance Films
- Starring: Adria Rae, April Aniston, Katrina Jade, Kenna James, Derrick Pierce, Eric Masterson, Ryan McLane, Tommy Pistol
- Movie Synopsis: These young sluts are looking for a father figure to fuck for a free ride! Stepdaddy fits the bill with a cock as big as his wallet! She's got the easy life on her brain, and boy is she easy! He's got... Read more
Mommy's Secret (2018)
- Studio: Girlsway
- Starring: Bridgette B, Carolina Sweets, Cherie DeVille, Kenna James, Melissa Moore, Mindi Mink, Moka Mora
- Movie Synopsis: Melissa Moore turns to step-mom Bridgette B to secretly help her release some sexual tension; meanwhile, Carolina Sweets concocts a plan negotiating with Mindi Mink to keep her questionable past a sec... Read more
- Studio: All Her Luv (AllHerLuv)
- Starring: Kenna James, Serena Blair
- Movie Synopsis: Serena Blair's stepsister, Kenna James, is self-centered, really ambitious, and hot.. undeniably sexy. Serena envied Kenna, and Kenna wants Serena. The two 18-year-old women come head-to-head when Ser... Read more
Doppelganger (2018)
- Studio: Sweet Sinner
- Starring: Alexa Grace, Kenna James, Samantha Hayes, Chad Alva, Lucas Frost, Ryan Driller
- Movie Synopsis: As technologic breakthroughs increasingly allow the ultra-wealthy to manufacture their appearance, the elite become unable to recognize their own reflection. Ryan has lost himself, and the love of his... Read more
Sister Stories (2019)
- Studio: Girlsway
- Starring: Carter Cruise, Dillion Harper, Eliza Jane, Ivy Wolfe, Kenna James, Piper Perri, Zoey Monroe
- Movie Synopsis: When Eliza Jane finds some of her missing clothes in her stepsister, Kenna James' room, she gets furious. After trying to reason with Kenna, a defeated, Eliza decides that if her sister doesn't unde... Read more
Lesbian Stepmother 5 (2019)
- Studio: Sweetheart Video
- Starring: Bridgette B, Dana Vespoli, Elexis Monroe, Gianna Dior, Kenna James, London River, Victoria Voxxx, Zoe Bloom
- Movie Synopsis: Sweetheart Video's popular taboo series is back with more insatiable stepdaughters and the lesbian stepmothers that love to seduce them! Enjoy four forbidden stepmom fantasies: a -dealing stepdaug... Read more
Almost The Same (2019)
- Studio: Girlsway
- Starring: Cherie DeVille, Ivy Wolfe, Karlee Grey, Kenna James, London River, Scarlett Sage, Sinn Sage
- Movie Synopsis: Karlee Grey is on the phone with her friends making plans for the day. Her stepmom, Sinn Sage, storms into the room and asks if she's ready to go to the beach. Karlee hangs up the phone and tells Sinn... Read more
Stepsister 3-Ways (2019)
- Studio: Zero Tolerance Films
- Starring: Alison Rey, Bailey Brooke, Daphne Dare, Judy Jolie, Kenna James, Lana Sharapova, Lyra Law, Lucas Frost, Nathan Bronson, Robby Echo
- Movie Synopsis: These dirty siblings take just about everything a "step" further. They're hot for each other, but that forbidden fucking isn't quite enough. They also want to share their horny lust to have ... Read more
- Studio: Pure Taboo
- Starring: Ivy Love, Kenna James, Jake Adams, Tommy Pistol
- Movie Synopsis: After being cheated on by her boyfriend (Mike Mancini), Avi Love seeks to rebuild her life. Although she hopes for a fresh start, Jessie's past quickly returns to haunt her when she gets hacked on her... Read more
Watching Porn with Jane (2021)
- Studio: MissaX
- Starring: Jane Wilde, Kenna James, Nathan Bronson
- Movie Synopsis: 18 year old Jane Wilde is video-chatting with her bestie Julia (Kenna James). The two young ladies are practically socialites. They're beauty is admired all over their small town, and they hang out wi... Read more
A Familiar Match (2021)
- Studio: Girlsway
- Starring: Gia Derza, Gianna Dior, Kenna James, Lauren Phillips, Rachael Cavalli, Sofi Ryan, Vanna Bardot
- Movie Synopsis: Lauren Phillips is frustrated because she doesn't know how to do basic household chores. Her stepdaughter, Vanna Bardot, hears her and she offers to give her a remedial course on basic chores. Over th... Read more
TS Taboo 7 (2021)
- Studio: TransSensual
- Starring: Kenna James, Liv Revamped, Izzy Wilde, Korra del Rio, Lianna Lawson, Natalie Stone
- Movie Synopsis: Description 2022 AVN Award Winner for Best Trans Series TransSensual presents an exciting taboo tale full of deceit and desire in TS Taboo 7 - All in the Family. Watch the four scene movie filled wi... Read more
Spank Me Instead! (2022)
- Studio: Girlsway
- Starring: Aften Opal, Gianna Dior, Hazel Grace, Katie Morgan, Kenna James, Laney Grey, Nikole Nash, Ryan Keely
- Movie Synopsis: Laney Grey is hopelessly in love with her step-mom, Ryan Keely. Luckily for her, the feeling's mutual! Although everything's been going great between them, there's still room to explore and have some ... Read more
Not My Grandpa! (2022)
- Studio: Crave Media
- Starring: Chanel Shortcake, Dakota Knight, Kenna James, Zoe Sparx
- Tag Line: Naughty selfies led to a scolding and pounding from Grandpa!
Suspicious Sister-In-Law (2022)
- Studio: Girlsway
- Starring: Alison Rey, Casey Calvert, Keira Croft, Kenna James, Rebecca Vanguard, Ryan Keely, Zoe Sparx
- Movie Synopsis: Casey Calvert and Keira Croft are two step-sisters who just found out that they're dating the same girl! It seems that Zoe Sparx has a thing for sisters and deceived them by dating both of them at the... Read more
Daddy Please 8 (2022)
- Studio: FullPornNetwork
- Starring: Alison Rey, Alix Lynx, Kenna James, Kiarra Kai, Laney Grey, Moka Mora, Norah Nova, Violet Starr, Barrett Blade
- Movie Synopsis: Black-haired Latina slut Violet Starr has a huge crush on her stepdaddy. So, she immediately jumped at the chance to fuck her stepdad's friend, who looks like him. Unfortunately for the busty babe, he... Read more
Foster Tapes Vol. 4 (2022)
- Studio: Team Skeet
- Starring: Aiden Ashley, Jazmin Luv, Jenna J. Ross, Kamryn Jayde, Kenna James, Lisey Sweet, Sheena Ryder
- Tag Line: Young girls discover the joy of foster care.
Learning to Love Yourself (2022)
- Studio: Fantasy Massage
- Starring: Adria Rae, Gia Derza, Jazmin Luv, Kenna James, Lily Larimar, Morgan Rain
- Movie Synopsis: Morgan Rain and Adria Rae, two step-sisters, are busy trying to figure out what to get their mom for her birthday. They decided that they will give their mom a massage for her birthday to go with the ... Read more
In Love With Your Mom Vol. 2 (2022) Compilation
- Studio: Sweetheart Video
- Starring: Cherie DeVille, Dana Vespoli, Elexis Monroe, Elsa Jean, Hime Marie, Ivy Wolfe, Kenna James, London River
- Movie Synopsis: Young and insatiable meets sexy and older in this forbidden film that features hottie MILFs seducing their young daughters! You'll love every titillating scenario in this sexy installment that always ... Read more
Best Of WebYoung: Sisters (2017) Compilation
- Studio: Web Young
- Starring: August Ames, Carmen Caliente, Dillion Harper, Hollie Mack, Janice Griffith, Kenna James, Mia Malkova, Nickey Huntsman, Piper Perri
- Movie Synopsis: Your biggest fantasy just came true. We have put together some of the hottest teen lesbians on earth on one DVD. Our members spoke and we listened! They're not just teens either, they're step-sisters!... Read more
My Mom's Tits (2017)
- Studio: Girlsway
- Starring: Allie Haze, Bobbi Dylan, Elexis Monroe, Gina Valentina, Jaclyn Taylor, Jasmine Summers, Jelena Jensen, Jenna J. Ross, Kenna James, Mindi Mink
- Movie Synopsis: Stepmother Jelena Jensen promises to help teen Jenna J. Ross regain her position on the cheer team. Stepmom Mindi Mink helps her teen stepdaughter Bobbi Dylan shoot a racy video to get the attention o... Read more
Three Little Sisters (2017)
- Studio: Web Young
- Starring: Ashley Adams, Elsa Jean, Gia Paige, Gina Valentina, Jenna Sativa, Jill Kassidy, Jojo Kiss, Kasey Warner, Kenna James, Lily Jordan
- Tag Line: Sisters, Students, Pizza Gals And More!
- Studio: #LetsDoeIt
- Starring: Blair Williams, Elsa Jean, Jill Kassidy, Kenna James, Lily Adams, Romi Rain, Samantha Hayes, Chad White, Derrick Pierce
- Movie Synopsis: Romi Rain is a strict stepmom but in secret she loves getting naughty with other women. Jill Kassidy has a huge crush on this foxy vixen so she oils up that curvy body then seduces Romi into a hardcor... Read more
- Studio: MissaX
- Starring: Kenna James, Maya Kendrick, Seth Gamble
- Movie Synopsis: What's a girl to do when she's failed to scare away her opponent? Kenna James is practically engaged to the man I love, Seth Gamble, who also happens to be my stepbrother. I thought that Seth would ad... Read more
Family Friction (2019)
- Studio: Fantasy Massage
- Starring: Carolina Sweets, Dee Williams , Kenna James, Eric Masterson, Nathan Bronson
- Movie Synopsis: With her step-sister's permission, Nathan Bronson offers a more hands-on lesson... Carolina Sweets first learns how to give a proper blowjob by going down on him, closing her mouth tightly around his ... Read more
Mommy's Daughter (2019)
- Studio: GirlGirl
- Starring: Chloe Cherry, Gianna Dior, India Summer, Jill Kassidy, Katie Morgan, Kenna James, Kiara Cole, Sarah Vandella, Serene Siren
- Movie Synopsis: 2020 AVN Award Nominee Best Female Mixed-Age Production Gianna Dior & India Summer Gianna hears her dad and step-mother arguing in their room. Concerned that they'll get divorced, Gianna steps in to ... Read more
- Studio: MissaX
- Starring: Kenna James, Chad White
- Movie Synopsis: Kenna is on Winter Break from college and staying at her stepfather's home. She's dressed in the sexiest lingerie, complete with garters and stockings as she teases in front of the webcam, "does ... Read more
Who's Your Daddy? (MissaX) (2020)
- Studio: MissaX
- Starring: Cadence Lux, Kenna James, Chad White
- Tag Line: Can I call you daddy?
Fantasy Factory (2017)
- Studio: Girlsway
- Starring: Adriana Chechik, Alexis Fawx, Brett Rossi, Cadence Lux, Kenna James, Serena Blair
- Movie Synopsis: Fresh out of the studio comes the newest Girlsway sci-fi thriller about a patented technology that brings "Member Fantasies" to life through next-generation virtual reality, and the lesbian ... Read more
Baddest Of Bad Daddy POV.com 2 (2021) Compilation
- Studio: FullPornNetwork
- Starring: Cadey Mercury, Charlotte Cross, Jessa Rhodes, Karma RX, Katrina Jade, Kenna James, Lena Paul, Moka Mora, Violet Starr
- Movie Synopsis: Make no mistake, BadDaddy has some of the sexiest, horniest, and most experienced cock suckers in the game. But these baddies take the cake! They're young, energetic, beyond horny, and always looking ... Read more
- Studio: Team Skeet
- Starring: Alexis Tae, Allie Nicole, Athena Faris, Charlotte Sins, Jewelz Blu, Kenna James, Kiarra Kai, Lacy Lennon
- Movie Synopsis: When stepsisters get competitive, sometimes things get nasty. Today, Kiarra Kai and Alexis Tae find themselves in a fierce battle for our studs sexual attention. Kiarra sucks him off with a deft prowe... Read more
Sis Swap (2022)
- Studio: Team Skeet
- Starring: Alex Coal, Angel Youngs, Haley Spades, Kenna James, Minxx Marley, Samantha Reigns, Skylar Vox, Johnny Love, Peter Green, Tyler Cruise
- Tag Line: The sisters trade their bodies for grades!
My New Family (2021)
- Studio: All Her Luv (AllHerLuv)
- Starring: Kenna James, Melody Marks, Rachael Cavalli
- Movie Synopsis: Joelle (Melody Marks) washes up in the bathroom and then runs off, wrapped in a towel, and finds her new stepmom and stepsister Katie (Rachael Cavalli and Kenna James) as Rachael tells Katie that she ... Read more
Step Daddy's Favorite Girls (2022)
- Studio: FullPornNetwork
- Starring: Alison Rey, Alix Lynx, Haley Reed, Jessa Rhodes, Karma RX, Kenna James, Khloe Kapri , Lexi Lore, Paige Owens, Violet Starr
- Studio: She Seduced Me
- Starring: Alina Lopez, Kenna James
World's Baddest Stepmoms (2023) Compilation
- Studio: FullPornNetwork
- Starring: Aaliyah Love, Alix Lynx, Cherie DeVille, Christie Stevens, Kenna James, Lauren Phillips, Linzee Ryder, Natasha Nice, Rachael Cavalli, Syren De Mer
- Movie Synopsis: These MILFs are super good at being super bad.
Cunning Linguist (2023)
- Studio: Girlsway
- Starring: Aften Opal, Kenna James, Kenzie Taylor, Lily Larimar, Mackenzie Mace, Mellanie Monroe, Serene Siren, Shay Sights
- Movie Synopsis: Mackenzie Mace is helping her stepmother, Mellanie Monroe, move into a new place. There's some nervous excitement in the air since both women are getting new beginnings: Mackenzie has just moved away ... Read more
Daddy Please 7 (2020)
- Studio: FullPornNetwork
- Starring: Dakota Skye, Judy Jolie, Kenna James, Laney Grey, Lena Paul, Barrett Blade
- Movie Synopsis: Super-hot, natural big tits and big ass blonde, Lena Paul finds her stepdaddy's toy in his room after she noticed it when she was cleaning, shes really curious about what it is and confronts her stepd... Read more
Cum Addiction (2020)
- Studio: Pure Taboo
- Starring: Athena Faris, Kenna James, Codey Steele, John Strong, Robby Echo
- Movie Synopsis: Lovers Carla (Athena Faris) and Rich (Codey Steele) are in each other's arms on Carla's bed, chatting and laughing. They begin having sex nervously, but as she grows to enjoy it, her skittishness fall... Read more
Pushing Boundaries (2020)
- Studio: MissaX
- Starring: Kenna James, Mona Wales, Ryan McLane
- Movie Synopsis: 2021 AVN Award Nominee for Best Taboo Relations Movie Kenna is coming home! Ryan's stepdaughter is finally coming home from college, but Mona wants Ryan cuffed and gagged in their bed. Ryan loves his... Read more
Twister (2020)
- Studio: All Her Luv (AllHerLuv)
- Starring: Brianne Blu, Kenna James, Mona Wales
- Movie Synopsis: Kenna watches the news streaming live from her cellphone, a tornado is making its way to her subdivision. Brianne runs in the house and looks for her stepsister, "Kenna! Kenna!" "I'm in... Read more
Who Rescued Who? III (2020)
- Studio: All Her Luv (AllHerLuv)
- Starring: Brianne Blu, Kenna James
- Movie Synopsis: They say 'opposites attract,' and Brianne yearns for truth in that saying. Brianne has always idolized her stepsister, Kenna James. The girls are opposites in every respect. Brianne is a reader, she's... Read more
Mixed Family Vol. 3 (2020)
- Studio: Family Sinners
- Starring: Jessie Saint, Kasey Warner, Kenna James, Mylene Monroe, Codey Steele, Nathan Bronson, Robby Echo, Stirling Cooper
- Movie Synopsis: The Mixed Family saga continues with even more family fantasy fun cum to life! Pairing up this time are: Kenna James and Quinton James, Kasey Warner and Cody Steele, Mylene Monroe and Nathan Bronson, ... Read more
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