A new painter arrives at art broker Darla Crane's residence afraid to show her his work because he knows she's a bit harsh when it comes to business. When he does, though, the redhead with the huge bust is too busy admiring him to focus on his painting. Nevertheless, she reels him back and pulls out the cock between his legs, sucking and fucking it till he demonstrates to her the true meaning of a flesh brushstroke, painting her cougar pussy with his sperm! Instead of sending him home with his tail between his legs!
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Johnny sneaks into his friend's house, revealing his undressed body to Lezley Zen, her hot mother. She catches him red-handed, chastising him for school pledge week. Johnny explains it's for school pledge week, saving him from Hell Week, and Ms. Zen inserts his cock into her.
Krystal Summers hires her son and friend Johnny to help her prepare for a yard sale. She becomes enthralled with Johnny, and to have time to fuck him, she asks him to perform another errand.
Emma Starr, a cougar separated from her husband, Johnny, a movie producer, supports Johnny by arranging a meeting with her ex-husband. Emma plays a game, "hiding Johnny's cock inside my vagina," and commands him to follow rules for success in show business.
Johnny, Ryan Keely's assistant, is responsible for ensuring smooth operations and timely completion of duties. However, he makes a mistake, leading to Ryan's loss of trust. To rectify the situation, Ryan hires Johnny to work on her pussy, hoping to atone for his transgressions.
Sara Jay tries to seduce her niece's wedding planner, but a miscommunication leads to her revealing that the man is not gay just because he works as a wedding planner and wears a pink blouse. She continues to sex him before revealing the truth.
Alura Jenson and Ava Addams promised Johnny's parents academic support, but Johnny's antics led them to demand payment, forcing him to repay them.
Johnny, a budding illusionist, learns a new card trick from Charlee Chase. However, the blonde, Charlee, believes Johnny is too skilled for it. Johnny learns "The Disappearing Pickle" and uses it to shoot a cumshot.
Phoenix Marie is upset with her boyfriend's constant fun with men, and her son Johnny consoles her. They become lustful, and Johnny forces his prick inside her, causing her to burst.
The narrator accidentally left their wallet in a grocery store cart, causing a fucking encounter with a hot guy in the parking lot. Upon returning home, they heard a knock on their door and recovered their wallet.
Johnny, Alison Tyler's boyfriend, visits to sew a dress for her, revealing her enormous tits. Johnny is fixated on them, but Alison allows him to penetrate her.
Johnny's girlfriend supports him in earning his master's degree, expressing her pride with a graduation present. Education seems to be rewarding.
Johnny, a blackjack player, is working to get a job, but is surprised when his father steals his credit cards after buying Brooklyn new boobs. Brooklyn flashes her new breasts to Johnny, who demands to see hers, expressing his frustration with his father's lack of interest in her.