Family Roleplay
Favorite9,358 Matches Found
The Car Won't Start (2018)
- Studio: Reagan Foxx
- Starring: Reagan Foxx,
- Movie Synopsis: Reagan Foxx is having a bad day as her car will not start as she is trying to get to work. As she calls in to tell the office she will not be in for the day, Reagan decides she will turn this bad day ... Read more
- Studio: Lily Cade
- Starring: Lily Cade, Natalia Starr, Natasha Starr, Nikki Next
- Movie Synopsis: Lily Cade is lucky today. She has two beautiful blonde sisters Natalia Starr and Natasha Starr join Lily and the pretty brunette Nikki Next in a fun and sexual lesbian foursome. There's plenty of puss... Read more
- Studio: Anal Fanatic
- Starring: Gia Derza, Ramon Nomar
- Tag Line: It's A Daddy Thing! 9
A Lesson From Aunt Kelly #3 (2000)
- Studio: Slippery Cat Studio
- Starring: Kelly Payne, Lisa
- Movie Synopsis: Once again Aunt Kelly is dealing with a disobedient nephew. This time his cousin catches him stealing money from her mother's pocket purse. After she tells her mother he is spanked, strapped and paddl... Read more
- Studio: African Porn Movies
- Studio: Sex Box Video
- Movie Synopsis: A horny mother and daughter are home alone, when a sexy black delivery man comes by. The daughter initiates things and gets the foreplay popping. But when the mother walks in, that's when the sparks r... Read more
Caught (2004)
- Studio: EroticaFirst
- Starring: Larisa Fox, Jason
- Movie Synopsis: I remember when I had many friends tell me their stories about getting caught by a relative jerking off, you know that sucks. But here is like a world in limbo, a world where getting caught by your st... Read more
- Studio: Michael Kahn Productions
- Starring: Paris Hershey, Serena Marcus
- Movie Synopsis: Ever fantasize about the relationship between two stunning, tattooed and sexy blondes and yourself? No need to imagine any more. Watch as these two work over the hard and erect cock, using their hands... Read more
Crossin Cousins (2000)
- Studio: Slippery Cat Studio
- Starring: Daisa, Kelly Payne
- Movie Synopsis: When an aunt leaves her nephew in the charge of his two strict cousins, you would think that he would know better than to misbehave. They soon find it necessary, however, to put him across their knees... Read more
- Studio: Mojo Studios
- Starring: Angelica Raven, Josh
- Movie Synopsis: Angelica Raven is a busty brunette beauty whose boyfriend just can't seem to please her sexually. She's horny as hell, and now has her eye on her stepbrother Josh. She's sits down with Josh wearing a ... Read more
- Studio: Mojo Studios
- Starring: Rochelle Lynne,
- Movie Synopsis: Rochelle Lynne is a busty tattooed beauty whose boyfriend just can't seem to please her sexually. She's horny as hell, and now has her eye on her older stepfather. She's here to seduce dear old stepda... Read more
- Studio: Alpha Beta Media
- Starring: Sarah Harris, Don Fernando, Lee LeMay
- Movie Synopsis: Number 109 from Diamond Collection Talk about an old, dirty man! There's only one way to know if a girl is good, and that's to fully sample the array of sexual acts she can provide! Grey panthers uni... Read more
- Studio: Amateur Spankings
- Studio: Red MILF Productions
- Starring: Charlie Mancini, Rachel Steele
- Movie Synopsis: Charlie idolizes her sexy stepmother Rachel and feels a forbidden attraction to her. When the two women go to Chicago for the wedding of a family friend, they end up sharing a hotel room. This intimac... Read more
- Studio: Red MILF Productions
- Starring: Monica Sexxxton, Rachel Steele, Stacie Starr, Shaggy
- Movie Synopsis: Rachel's stepsister Stacie was in town for a big work project. Rachel insisted that she stay with her instead of a hotel. She told Stacie to bring Rachel's niece Monica and nephew Alex along. His long... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Stacie Starr, Brian Omally, Frank, Ricky Roads
- Movie Synopsis: Sisters Rachel and Stacie vacation at a hotel on a tropical island. Rumor has it the place is haunted by mischievous spirits conjured up by long extinct natives. Should be safe for their stepsons, Rac... Read more
- Studio: Red MILF Productions
- Starring: Penny, Rachel Steele
- Movie Synopsis: Rachel's friend Penny dropped by to visit. Rachel's ex-stepson, Johnny, sat on the couch texting friends. Penny had not seen Rachel for a while and asked how she was getting along after the divorce. R... Read more
- Studio: Red MILF Productions
- Starring: Kelsie Cummings, Rachel Steele
- Movie Synopsis: Kelsie gets kicked out by her father's house and shows up at her mom's house, Rachel Steele. Rachel and she are very close. Then her son shows up at the house after Rachel has made her daughter change... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele,
- Movie Synopsis: Rachel's Husband is quite upset with her. She puts her son first for everything. He comes home after a long hard day from work. Rachel's been at her sons practice. He asks what's for dinner and since ... Read more
- Studio: Red MILF Productions
- Starring: Stacie Starr,
- Movie Synopsis: Stacey Starr's son is looking at a photo. He starts to discuss another mom and that Stacey could be hot too. Stacey says it's been hard since her husband left them and doesn't seem to care about her l... Read more
Family Fantasies - MILF 552 (2009)
- Studio: Red MILF Productions
- Starring: Stacie Starr,
- Movie Synopsis: Julia's stepson found an old photo album. As he looked through, he commented on how beautiful and hot she was. He asked her why she had let herself go. Julia explained to him that since his father had... Read more
Family Fantasies - MILF 567 (2009)
- Studio: Red MILF Productions
- Starring: Aliysa Moore, Rachel Steele, Stacie Starr
- Movie Synopsis: Stacey Starr's sex life is so boring as she complains about it to her husband. She wants his to try new things or she wants to be on top for a change. Watch these five scene's of a circle of taboo in ... Read more
Family Fantasies - MILF 601 (2009)
- Studio: Red MILF Productions
- Starring: Rachel Steele, Stacie Starr
- Movie Synopsis: Stacie Starr gets a phone call about her sister Rachel Steele about how she's drinking all the time and dressing inappropriate and having sex all over the place. Rachel is getting kicked out so Stacey... Read more
- Studio: Red MILF Productions
- Starring: Aliysa Moore, Rachel Steele, Stacie Starr
- Movie Synopsis: In this volume watch as the family goes to see Rachel Steele for some counseling in regards to their sexual fantasies. First to visit Rachel in her office is the son of Stacey Starr and brother of Lei... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Sara James
- Movie Synopsis: Rachel Steele just got a devastating letter that her son and her sister's can have no more contact with them because they are unfit mothers. Rachel goes on the internet to locate the boys. After awhil... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Stacie Starr, Brent
- Movie Synopsis: After the divorce, Rachel and her stepson Brent went on with their lives. One afternoon, Rachel was organizing her closet when she found a box high up on the shelf. She took it down to see what was in... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele,
- Movie Synopsis: Rachel Steele vents to her son how her boss never appreciates anything she does and she feels she can never do anything right for him. Her son feels bad for his mom. One day the door bell rings and Ra... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Stacie Starr
- Movie Synopsis: Rachel's sister and her step-son Brycen had come to stay for a long weekend. Brycen had turned 21 and was attending college. Julia had been divorced for several years and was finally getting back into... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, John
- Movie Synopsis: Rachel's son-in-law John had been staying with her for a few weeks while her daughter (his wife) was away on business. Their house was being remolded, so he needed to stay with Rachel. They got along ... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Sara James
- Movie Synopsis: Rachel Steele discovers that her son is taking her panties and masturbating with them. Aunt Sara is staying with them and she has also noticed her son watching her shower. She explains this to her hus... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Taylor , Brycen Ward
- Movie Synopsis: Rachel Divorced 10 years ago and chose to raise her stepson Brycen alone. Brycen and Rachel were very close. They lived in a remote farm house so social activities did not exist. Brycen took his colle... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Taylor
- Movie Synopsis: Rachel's son comes to her to discuss that his sister is having too much sex with different guys all the time. She has a talk with her daughter about it. Taylor is a very horny girl and masturbates bef... Read more
- Studio: Red MILF Productions
- Starring: Sara James, Brycen Ward
- Movie Synopsis: Sara worked two jobs trying to help out with her step-son's college. Her husband and Brycen had been very lazy because she was not home a lot anymore. This infuriated her when she would come home exha... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele,
- Movie Synopsis: Rachel gets an unexpected visit from her son Brycen. He's wearing priest clothing and she can't really believe he went into the priesthood. She hasn't seen him since he was much younger. She watches h... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Taylor
- Movie Synopsis: Taylor Rachel Steele's sister is staying with her. Rachel is having a hard time with her son Brycen helping around the house while she works to jobs to try and pay the mortgage. She finds out through ... Read more
Family Fantasies - MILF 771 (2010)
- Studio: Red MILF Productions
- Starring: Rachel Steele,
- Movie Synopsis: Rachel Steel's husband comes home early from work and has bad news that he got laid off from his job. Now they are in big financial trouble. Rachel decides to call her nephew for some help in regards ... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Frank Steele, Kenny Cox
- Movie Synopsis: The perfect family and the perfect mother... or is it? Mrs. Cleaver has a little secret; she has a side of her you will see is extremely TABOO. After the family breakfast Mrs. Cleaver sent her men off... Read more
- Studio: Red MILF Productions
- Starring: Dallas Diamondz, Rachel Steele
- Movie Synopsis: I Got a D in Biology Rachel is a very strict and reserved stepmom to Kenny. When the young man gets a D in biology due to his lack of knowledge about the birds and bees, a desperate Rachel sends him ... Read more
- Studio: Red MILF Productions
- Starring: Dallas Diamondz, Misty Cummings, Rachel Steele
- Movie Synopsis: Uptight Rachel is trying to protect her stepson Jeremy and her stepdaughter Misty from bad influences. Her late husband's Will stipulated that in order to gain their inheritance they must do well at s... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele,
- Movie Synopsis: Rodney's stepmother Rachel is a bubbly MILF with a penchant for revealing outfits. His friend Jake bets him he can seduce and fuck her within 48 hours. The young man succeeds, and Rodney becomes jealo... Read more
- Studio: Red MILF Productions
- Starring: Rachel Steele, Sarah Quinn, Jack Moore, Rodney Pierce
- Movie Synopsis: Rachel is upset at the breakdown in communication in her family. She goes to a consignment shop and buys a board game for them all to play. She hopes it will lead to everyone bonding. What she does no... Read more
- Studio: Red MILF Productions
- Starring: Charlotte Davis, Brian Omally, Kyle Chaos
- Movie Synopsis: Prankster Brian desperately wants to fuck his stepsister Charlotte - his hot cock tease of a stepsister. Whenever he tries to make a move on her, she rejects him playfully. But he perseveres. On one o... Read more
- Studio: Red MILF Productions
- Starring: Jayden reese, Rachel Steele, Frank Steele, Kyle Chaos
- Movie Synopsis: Rachel's devoutly religious boss gives her the responsibility of looking after his wayward stepson and stepdaughter while he is out of the country doing missionary work. Meanwhile, her naughty twin si... Read more
- Studio: Red MILF Productions
- Starring: Alexis, Rachel Steele, Eric, Frank
- Movie Synopsis: Rachel is being neglected emotionally and sexually by her husband Frank. She discovers that he's been getting his cock sucked in the office by his secretary Alexis. That same night, Rachel has an erot... Read more
- Studio: Red MILF Productions
- Starring: Dallas Diamondz, Rachel Steele
- Movie Synopsis: Rachel is frustrated with her impotent husband Joe. One morning she dresses up sexily and goes all out to get him hard. Joe starts to make out with her, but still is not able to deliver the goods. Lat... Read more
- Studio: Randy De Troit
- Movie Synopsis: Family planning is a joy for all families; join in the joy as a husband and his pregnant wife share the joy of having sex while his wife is pregnant. For some men the vision of a pregnant woman is eno... Read more
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