The Babysitter is the most cuckold-heavy movie I've ever seen. From 1995, Alicia Silverstone stars as the object of three men's fantasies- her boyfriend, her boyfriend's rival, and the father of the children she's watching. Every character is extremely sexually frustrated, and the movie frequently slips into various character's kinky fantasies.
The Babysitter (1995) Alicia Silverstone Part 5 FIVE - YouTube
In this clip, at about 50 seconds in the father fantasizes about catching the babysitter and her boyfriend going at it in his house. He fantasizes about humiliating the younger guy, pulling him off of Silverstone, scaring the hell out of him with threats of calling the cops and calling him "boy." When the kid tries to get dressed, he rips the clothes out of his hand so that the kid is ******* in just his boxers, and the father laughs "Look at that little thing poking out there," cruelly pointing out his small teenage hard-on to Silverstone. He then roughly forces the kid out of his house, telling him to "run home bare ass." The father now enjoys the babysitter to himself.
There's definitely an element of a middle-aged man wanting to prove his virility over a younger riva reestablishing his masculine authorityl. He wants to put the kid in his place, belittle and humiliate him in front of her so that she no longer sees him as sexually viable.
All throughout the movie, the boyfriend's friend is trying to get him to meet up with Silverstone so that they can double team her. In truth, the friend wants to bang her in front of his friend, taking her away from him forever. He tries plying him with alcohol and weed to make him submissive and uninhibited. 5 minutes in to the above clip, the friend imagines all three of them naked, him laying the pipe into her as his naked friend watches, dazed and defeated, as his friend proves his superior sexual prowess. and takes his girlfriend from him
The Babysitter (1995) Alicia Silverstone Part 5 FIVE - YouTube
In this clip, at about 50 seconds in the father fantasizes about catching the babysitter and her boyfriend going at it in his house. He fantasizes about humiliating the younger guy, pulling him off of Silverstone, scaring the hell out of him with threats of calling the cops and calling him "boy." When the kid tries to get dressed, he rips the clothes out of his hand so that the kid is ******* in just his boxers, and the father laughs "Look at that little thing poking out there," cruelly pointing out his small teenage hard-on to Silverstone. He then roughly forces the kid out of his house, telling him to "run home bare ass." The father now enjoys the babysitter to himself.
There's definitely an element of a middle-aged man wanting to prove his virility over a younger riva reestablishing his masculine authorityl. He wants to put the kid in his place, belittle and humiliate him in front of her so that she no longer sees him as sexually viable.
All throughout the movie, the boyfriend's friend is trying to get him to meet up with Silverstone so that they can double team her. In truth, the friend wants to bang her in front of his friend, taking her away from him forever. He tries plying him with alcohol and weed to make him submissive and uninhibited. 5 minutes in to the above clip, the friend imagines all three of them naked, him laying the pipe into her as his naked friend watches, dazed and defeated, as his friend proves his superior sexual prowess. and takes his girlfriend from him
