The Headmaster is unhappy with all the Academy girls behavior as of late. As the Head Girl, Daija is at least partially responsible for the other girls' behavior. As a result, Daija is given a second monthly punishment day. The Headmaster takes the opportunity to try out a new hairbrush and work on some new spanking positions as well.

The Headmaster instructs Becca on appropriate dress for a proper young women. She is bent over a table. Her skirt is lifted and her panties pulled down. The Headmaster spanks her to tears with his trusty red ping-pong paddle.

The Headmaster interviews Daija about her most recent transgressions at the Academy. He then immediately follows this with some negative reinforcement correction in the form a painful caning with a fiberglass cane.

Coed Bailey is caught smoking when she is supposed to be studying. The Headmaster orders her to his office where she is made to strip naked and bend over a desk. She is given a very hard strapping as she sobs heavily. A long painful punishment.

Sleepy Mila is awakened warmly by the Headmaster with a loving caress and a taste of the strap. She then goes over his knee for a brisk and invigorating hairbrush spanking.

Daija, in a futile attempt to flee the Headmaster's wrath, takes to the woods. But alas, escape is not so easy and he catches her in the old abandoned building down by the river (some say it is haunted). Justice is swift and painful as the Headmaster skillfully wields the ping pong paddle of righteousness on the troubled lass' tender bottom.

When Mila tries to sneak into the house after having stayed out all night the Headmaster is waiting for her. Her punishment continues in the bedroom, where she is order to strip naked and get on the bed on knees and elbows for a dose of the strap. She then goes over his knees for a spanking with the hairbrush.

When Mila tries to sneak into the house after having stayed out all night the Headmaster is waiting for her. He punishes her on the spot with hand and strap, then sends her to her bedroom for more.

Naked Daija is put in the legs up position on the conference table by the Headmaster and spanked hard with a hairbrush. Tears and sobbing ensue.

Shy new girl Casey is welcomed into the Academy by the Headmaster. She is interviewed, inspected and punished several times.