Lecherous old Harry (Jamie Gillis) is dying in the hospital. Uncertain as to how he should will his massive fortune, he makes a wager with his four children to challenge them to engage in the wildest and most erotic sexual escapades they can think of

What could be better than group activities to strengthen bonds between colleagues?

As a housekeeper in a luxury hotel, Avril knows every little secret behind every door.

Everything was fine until his son (Tyler Cruise) brought home his beautiful new girlfriend (Kay Lovely) to meet the family and those old familiar feelings came rushing back. Now Derrick has to make a decision between betraying his wife and son or keeping his promise to be faithful.

Whitney meets Ryan on a dating app and realizes that he used to be her sociology professor when she was in college. They reconnect and fall in love but eventually Ryan confesses to being in The Lifestyle and invites Whitney to a swingers retreat for the weekend.

Vic is tired of "dating down" and wants some security in her life. She meets Derrick, a handsome and generous man who whisks her and her best friend Bunny away to a luxury resort for the weekend. All seems to be perfect until she meets a handsome bartender with big dreams and an even bigger heart.

Shot at San Francisco's Kearny Street Cinema, Punishment Pony chronicles a bizarre sexual stageshow.