Family Roleplay
Favorite45 Matches Found
Moms In Control 16 (2021)
- Studio: Brazzers
- Starring: Aaliyah Hadid, Alura Jenson, Bailey Brooke, Jill Kassidy, Kendra Lust, Kristen Scott, Lela Star, Sarah Jessie, Keiran Lee, Xander Corvus
- Movie Synopsis: Jill Kassidy has to spend a whole weekend with her busty stepmom Lela Star and neither of them wants to be there. But the fact that the concierge, Keiran Lee, is drooling all over Lela's big fake tits... Read more
- Studio: Pure Taboo
- Starring: Aaliyah Love, Jill Kassidy, Kristen Scott, Derrick Pierce, Tommy Pistol
- Movie Synopsis: Conservative stepmom Mary Ann (Aaliyah Love) convinces her boyfriend (Derrick Pierce) to fuck her lesbian stepdaughter Charlie (Kristen Scott) because she doesn't accept homosexuality in her house. On... Read more
Stepdaughter Orgy (2021)
- Studio: She Seduced Me
- Starring: Cherie DeVille, Chloe Cherry, Jill Kassidy, Milana Ricci
Wants What She Can't Have (2022)
- Studio: Pure Taboo
- Starring: Eliza Eves, Jill Kassidy, Charles Dera, Tommy Pistol
- Movie Synopsis: Lola (Jill Kassidy), a teen waitress at a bar seduces her innocent married boss Tim (Charles Dera). Lola aggressively comes onto Tim. He tries to resist but ultimately can't as she begins to suck his ... Read more
- Studio: MissaX
- Starring: Jill Kassidy, Krissy Lynn, Chad White
- Movie Synopsis: It's early in the morning and Chad is pacing the floors of his father and step-mother's house. Krissy comes out of their bedroom in her pajamas and is surprised to see Chad dressed, "want some pa... Read more
- Studio: MissaX
- Starring: Jill Kassidy, Chad White
- Movie Synopsis: Laura has a mission for Jill. When Laura convinced Jill have sex with her godmother, it gave her the idea of the hottest foursome. It's Laura's ultimate goal to conduct the hottest scene between hers... Read more
Moms Bang Teens Vol. 27 (2018)
- Studio: Reality Kings
- Starring: Bailey Brooke, Bridgette B, Gina Valentina, Jill Kassidy, Karlee Grey, Kristen Scott, Lea Lexis, Reagan Foxx, Jessy Jones, Seth Gamble
- Movie Synopsis: These hot mommies are on the hunt for young studs! They are seriously craving some rock hard dicks and aren't willing to stop until they get what they want!... Watch these unbelievably sexy, horny mom... Read more
- Studio: MissaX
- Starring: Jill Kassidy, Krissy Lynn, Chad White
- Movie Synopsis: Jill turns her attention to Chad and whispers in Chad's ear, "let's make Mommy fuck us..." Chad says, "We're not having sex with Krissy, she's been like a mother to us.. no. it's out o... Read more
It's Stuck (2018)
- Studio: Girlsway
- Starring: Alex Grey, Cherie DeVille, Jill Kassidy, Megan Rain, Melissa Moore, Reena Sky, Samantha Rone, Syren De Mer
- Movie Synopsis: Mob boss wife Cherie DeVille gets the news that her husband's in jail. She comes to the conclusion that she's in charge now. Cherie's stepdaughter Samantha Rone hears the news and informs her wife Ale... Read more
Daughter Swap 4 (2018)
- Studio: Team Skeet
- Starring: Arya Fae, Blair Williams, Jade Jantzen, Jill Kassidy, Maya Kendrick, Eric John, Filthy Rich, Marcus London, Sean Lawless, Tommy Gunn
- Tag Line: You get to fuck his daughter . . . but he gets to fuck yours!
Daddy's Dream Date (2018)
- Studio: ATKingdom
- Starring: Alex Blake, Bella Rose, Gia Paige, Jill Kassidy, Pepper Hart, Tara Ashley
- Movie Synopsis: Brunette Beauty Gia Paige Uses Her Feet on His Cock and Fucks Him Lovely Jill Kassidy Gets Fingered in POV Cute Blonde Bella Rose Enjoys a Pussy Pounding Red Haired Doll Pepper Hart Sucks His Cock ... Read more
- Studio: Girlfriends Films
- Starring: Athena Faris, Jayden Cole, Jenna Foxx, Jill Kassidy, Julia Ann, Reagan Foxx, Ryan Keely, Scarlett Sage
- Tag Line: Mother Knows Best!
The Family Tradition (2018)
- Studio: Pure Taboo
- Starring: Ashley Adams, Aubrey Sinclair, Jill Kassidy, Alec Knight, Dick Chibbles
- Movie Synopsis: Mom and dad are sitting up in bed, watching TV, when Paula enters the room in her robe. She is holding a suspicious glass of water, which she hands to mom. When mom notices her, she tells her how ador... Read more
All In The Family (2019)
- Studio: Karups
- Starring: Christie Stevens, Jill Kassidy, Miky Love, Rebecca Volpetti, Alex Davis, Bruno SX, Dean Van Damme, Eric Masterson
- Movie Synopsis: When life gets in the way, just remember.... It's All In The Family! Her stepbrother catches her sunbathing topless and she catches him with a hard on! When a woman has a body as nice as this, all the... Read more
Trickery: Indecent Proposals (2019)
- Studio: BANG!
- Starring: Abella Danger, Brandi Love, Gianna Dior, Jill Kassidy, Codey Steele, Connor Kennedy, Damon Dice, Filthy Rich
- Movie Synopsis: Sometimes desire gets so intense that you would go to any lengths to satisfy its burning demands. Bang presents four taboo tales of trickery and hardcore sex with the hottest talent in adult films tod... Read more
Closer To My Stepdaughter (2019)
- Studio: Girlsway
- Starring: Cherie DeVille, India Summer, Jenna Sativa, Jill Kassidy, London River, Scarlett Sage
- Movie Synopsis: Jill Kassidy admits that she pushed her date away when it came time for a goodnight kiss. She's never kissed anyone before, so she got scared. In fact, that's why she's there talking with London River... Read more
I Like My New Stepsister (2016)
- Studio: Peter North
- Starring: Jaye Summers, Jill Kassidy, Lilly Ford, Summer Day, Chad White, Jessy Jones, Mr. Pete, Xander Corvus
- Movie Synopsis: Chad, Xander, Mr. Pete and Jessy have all tried to resist the temptations living underneath the same roof. But when you have a Step Sister this fuckable...who could resist? Mr. Pete's step sister Jaye... Read more
Dirty Family (2017)
- Studio: Pretty Dirty
- Starring: Alison Rey, Brett Rossi, Jill Kassidy, Kenzie Taylor, Lily Adams, Simone Garza, Derrick Pierce, Jessy Jones, Marcus London, Ryan McLane
- Movie Synopsis: Stop Fucking My Mom: When Jessy Jones prioritizes watching the game over listening to his girlfriend Alison Rey express her feelings, he hardly notices when she scampers off in tears. Jessy is too eng... Read more
Half His Age (2017)
- Studio: Pure Taboo
- Starring: Cherie DeVille, Jill Kassidy, Kristen Scott, Charles Dera, Small Hands, Xander Corvus
- Tag Line: A Teenage Tragedy
- Studio: Lesbian Glam
- Starring: Jill Kassidy, Lana Rhoades
- Studio: MissaX
- Starring: Jill Kassidy, Chad White
- Movie Synopsis: Meet Jill Kassidy. Jill has a secret friend, Laura, you may think she's merely a doll, but she is a real live girl, as real as Jill. Jill's parents took her to get psychiatric help because they want h... 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!
ATK Daddy Fucked Me Hard (2017)
- Studio: ATKingdom
- Starring: Elena Koshka, Gia Paige, Jill Kassidy, Kenzie Reeves, Lana Rhoades, Yara Skye
- Movie Synopsis: These horny, young chicks can't contain themselves! They're looking for any hard cocks they can stick in thier tight, dripping holes! What they need is a man to show them what real fucking is all abou... Read more
It's A Sister Thing! Vol. 2 (2017)
- Studio: Elegant Angel
- Starring: Ashley Adams, Bella Rose, Eliza Jane, Jill Kassidy, Lana Rhoades, Lily Jordan, Sydney Cole, Zoey Taylor
- Movie Synopsis: Elegant Angel presents It's A Sister Thing! Vol. 2 over 2 hours of steamy step sister fun! Sisters go wild in this incredible lesbian experience! For all you taboo lovers out there this is your ultima... Read more
Mother's Choice, A (2017)
- Studio: Pure Taboo
- Starring: Alexis Fawx, India Summer, Jill Kassidy, Whitney Wright, Derrick Ferrari, Robby Echo
- Movie Synopsis: Charity (India Summer), and stepdaughter Jessica (Whitney Wright) pull up to their new life with Charity's new husband. Eager to be out of the place they once were, it proves a sensitive topic for bit... Read more
Daddy's Girls (2017)
- Studio: AMK Empire
- Starring: Elena Koshka, Elsa Jean, Gia Paige, Jill Kassidy, Kenzie Kai, Kenzie Reeves, Moka Mora
- Movie Synopsis: Kenzie Reeves has her pussy pounded in pov stile and looking at her facial expressions, she's between enjoying it and regretting to take the big cock inside. She is left with a creampie and a bandged ... Read more
Lesbian Stepsisters Vol. 6 (2017)
- Studio: Sweetheart Video
- Starring: Abella Danger, Adria Rae, Ayumi Anime, Carter Cruise, Giselle Palmer, Jill Kassidy, Katana Storm, Shyla Jennings
- Movie Synopsis: What happens when you find yourself wildly attracted to your stepsister? The answer can be found in the latest installment of Sweetheart's Lesbian Stepsisters... Shyla Jennings can't stand her caprici... Read more
- Studio: MissaX
- Starring: Jill Kassidy, Chad White
- Movie Synopsis: I'm about to leave for college and everyone is wanting a piece of my time before I go. I feel drained and I haven't even got a chance to cope with the idea that I am leaving the only home I've ever kn... Read more
It's A Daddy Thing! 8 (2018)
- Studio: Elegant Angel
- Starring: Jill Kassidy, Kimber Woods, Lilly Ford, Whitney Wright, Alec Knight, John Strong, Ramon Nomar, Tommy Gunn
- Movie Synopsis: Elegant Angel presents It's a Daddy Thing #8 with over 2 hours of teen & step-daddy fun. Filthy young flirtatious teens seducing older men aka their Step-Daddies! This movie is a sexually sophisticate... Read 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
Private Family Vacation (2019)
- Studio: AMK Empire
- Starring: Carmen Rae, Emma Hix, Jill Kassidy, Megan Marx, Niki Snow, Riley Star
- Movie Synopsis: Hot Babe Niki Snow Gets Some Close Up Cock, Cute Carmen Rae Gets Some Hard Cock, Cutie Megan Marx Lets Him Touch Her Pussy, Cutie Riley Star Gets Her Pussy Touched in the Car, Pretty Jill Kassidy Suck... Read more
Daddy Tried To Impregnate Me (2019)
- Studio: JayRock Productions
- Starring: Dolly Leigh, Jill Kassidy, Khloe Kapri , Lily Adams, Jay Rock
- Movie Synopsis: These stepdaughters are in for a surprise when their stepdad takes it too far. Nothing teaches a lesson more than her daddy trying to impregnate her! These girls have grown so fast. They're all grown ... 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
Sibling Rivalry (2019)
- Studio: Family Hookups
- Starring: Eliza Ibarra, Gina Valentina, Jill Kassidy, Vanna Bardot, Codey Steele, Seth Gamble, Tommy Pistol, Tyler Nixon
- Movie Synopsis: Jill Kassidy just got home from college and her younger stepbrother wants to hear all about it. She tells him all about the wild parties and sex (including a threesome!) that she's been up to but he g... Read more
Obsession (2020)
- Studio: MissaX
- Starring: Cherie DeVille, Jill Kassidy, Chad White
- Movie Synopsis: There are two women in my life, my step-mother and my girlfriend. There's been a tension between the two, and they haven't even met yet. They both think that the other occupies too much of my time. T... Read more
Lesbian Stepsisters Vol. 9 (2020)
- Studio: Sweetheart Video
- Starring: Charlotte Cross, Charlotte Stokely, Jezabel Vessir, Jill Kassidy, Karla Kush, Karlee Grey, LaSirena69, Sophie Sparks
- Movie Synopsis: Sweetheart's fan favorite series, Lesbian Stepsisters is back! In this 9th opus, eight beautiful ladies enjoy the pleasures of their sister from another mother. Sophie (Sophie Sparks) meets her new s... Read more
Step Siblings Caught 8 (2017)
- Studio: Nubiles
- Starring: Ariana Marie, Chloe Cherry, Elsa Jean, Ember Stone, Jill Kassidy, Kacie Castle, Alex Davis, Brad Hart, Jason, Tyler Nixon
- Movie Synopsis: Ember Stone & Jill Kassidy - 2 very demanding step-sisters! These girls are always telling their step-brother what to do but that's always a bad thing! Chloe Couture & Elsa Jean - Is it wrong for you... Read more
Paternity Tested (2020)
- Studio: Pure Taboo
- Starring: Carolina Sweets, Jill Kassidy, Kenzie Taylor, Mr. Pete, Tommy Gunn
- Movie Synopsis: Kelly's (Jill Kassidy) been on the hunt for her birth father for years, with many disappointments along the way because of dishonest people. She's doubled her efforts since her mother passed away, des... Read more
Sneaky Sex 19 (2020)
- Studio: Reality Kings
- Starring: Ariana Marie, Autumn Falls, Avery Moon, Jill Kassidy, Kali Roses, Damon Dice, J-Mac, Sean Lawless, Tyler Steel, Xander Corvus
- Movie Synopsis: Sean Lawless is late for work again, and just his luck, his boss catches him in the elevator and starts berating Sean in front of his super hot Latina girlfriend, Autumn Falls. Autumn tells her boyfri... Read more
- Studio: NSFW Films
- Starring: Alex Coal, Athena Faris, Izzy Lush, Jill Kassidy, Kenzie Reeves, Naomi Swann, Scarlett Sage, Vina Sky
- Movie Synopsis: Naomi & Alex childhood girlfriends that have crossed the line and have become lovers! Vina & Kenzie met in class, their opposite look instantly attracted one another to each other! Izzy & Jill step-... Read more
- Studio: Girlsway
- Starring: Alex De La Flor, Alina Lopez, Jade Baker, Jill Kassidy, Kendra James, Natasha Nice, Sinn Sage
- Movie Synopsis: Looking up at her step mom or Strap-Mom, Kendra, Jill excitedly tells her that she's been accepted to Alaskan University! But Kendra doesn't share Jill's excitement. "Wouldn't you miss our time t... Read more
Teach me well (2023)
- Studio: Girlsway
- Starring: Blair Williams, Jill Kassidy, Keisha Grey, Samantha Rone, Syren De Mer
I Love When Daddy Cums Home (2016)
- Studio: Peter North
- Starring: Alana Summers, Jill Kassidy, Katya Rodriguez, Liza Rowe, Eric John, John Strong
- Tag Line: 4 All New Taboo Scenes
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