Shy college teacher, Bob Lee Jennings, is a man easily distracted by a sexy female bottom, especially encased in tight denim jeans. It becomes an obsession, and develops further into 'accidental' groping... which gets him into big trouble at a store selling cowboy boots. Despite a whipping, his bad behaviour continues at a different store, where three women delight in getting their own back by fondling and spanking him. One of them, Stephanie, blackmails Bob Lee about the incident, which does not go down well with Bob-Lee's new girlfriend, Jesse. Jesse, a cowgirl, really likes the sweetly submissive Bob Lee but is faced with the problem of how to deal with his obsession for female bottoms. She meets with Bob Lee's mother at her ranch, and his mother comes up with a plan, carried out in the barn with the aid of a saddle rack, leather strap, and Bob Lee wearing his 'spanking chaps'. A further painful session in the barn involves more sessions with the strap from each of Bob Lee's three older sisters, all equally determined to help cure him of his obsession.