Your Search Returned 1085 Results
Daija: Birthday Spanking
For Daija's 21'st birthday, the Headmaster gives her a fully nude paddling.
Updated: Wed. Feb. 02, 2022
Jenna: Hairbrush Spanking
When the Headmaster picks Jenna up from school, he discovers she is not wearing her uniform, but rather something much more revealing and inappropriate. While lecturing her on the importance of proper dress and modesty, she interrupts repeatedly asking for a soda. Annoyed at the girl's insolence, the Headmaster pulls over the van and spanks her OTK with his trusty hairbrush.
Updated: Mon. Jan. 31, 2022
Daija: Cleaning the Van
As Daija cleans the Academy van, the Headmasters offers guidance and gentle instruction.
Updated: Fri. Jan. 28, 2022
Jenna: Fashion Police
Jenna and the Headmaster just cannot seem to see eye-to-eye on fashion. When Jenna arrives at the institute wearing yet another 'slutty' outfit, the Headmaster has had enough. Jenna receives a long hard multi-implement punishment that includes; hand, hairbrush, strap, ping pong paddle, wooden paddle, a rubber glove inspection and finishes with her naked, trembling and in tears.
Updated: Wed. Jan. 26, 2022
Maria's Attitude Adjustment
Maria receives a long hand spanking in various positions from the Headmaster in an attempt to improve her attitude for the better.
Updated: Mon. Jan. 24, 2022
Daija & Kelly: Bare Bottoms in the Boardroom
Daija and Kelly are both given given bare bottom hand-spankings by the Headmaster for inappropriate dress, first OTK and then bent over the end of the table.
Updated: Fri. Jan. 21, 2022
Olivia: Learning the Rules
New girl Olivia is still a bit rough on the rules at the Academy. After arriving late and failing to remove her shoes before entry, the Headmaster graciously offers Olivia some private instruction on the Academy rules.
Updated: Wed. Jan. 19, 2022
Angelina: Learning to Obey
Stubborn Angelina needs guidance and motivation to be more obedient to her boyfriend. She is ordered to strip out of her school uniform and is given an OTK hand spanking on her already red and sore bottom by the Headmaster.
Updated: Mon. Jan. 17, 2022
Brooke: Spanked by Daija
A naked Daija spanks a naked Brooke with the ping-pong paddle.
Updated: Fri. Jan. 14, 2022
Daija: Not Ready on Time
Daija does not spend the time to fix herself up as the Headmaster has instructed her again and again. Her hair is a mess. Her make up is done haphazardly. To help remind her to always look her best, as a young lady should, the Headmaster gives her a bare bottomed OTK hand-spanking. During her punishment Daija will not hold still. The Headmaster has no choice but to use the hairbrush on her. He then sends her to fix her make up properly and checks the results. The Headmaster finishes up with a few more swats to Daija's bare bottom.
Updated: Wed. Jan. 12, 2022
Angelina: Long Paddling
Angelina arrives at the Academy in disarray. She seems to have forgotten all the rules with regard to the Academy dress code. The Headmasters orders her to strip naked and then soundly paddles her with a wooden paddle on bottom and foot. She is left bruised and teary eyed.
Updated: Mon. Jan. 10, 2022
Daija: Bedtime OTK
The Headmaster gives young Daija a before bed OTK hand-spanking on her bare bottom.
Updated: Fri. Jan. 07, 2022
Jenna: Bed Strapping
Jenna is laid out naked on the bed and strapped by the Headmaster with his belt.
Updated: Wed. Jan. 05, 2022
Brooke and Daija: Two Girl Naked Paddling
The Headmaster paddles naked Brooke and Daija together in their bedroom. Each girl is put on the bed on-all-fours and paddled while the other girl kneels on the floor awaiting her turn.
Updated: Mon. Jan. 03, 2022
Taylor: The Punishment Room
Taylor is led by her hair to the punishment room. The Headmaster positions her on-all-fours, applies some judicious groping and then spanks her already very red bottom.
Updated: Fri. Dec. 31, 2021
Daija: Bad School Girl
Daija is being insolent as all get out. The Headmaster is not amused. He deals swiftly and decisively with her disrespectful attitude. She is ordered to bare her bottom and is then properly paddled. That stings!
Updated: Wed. Dec. 29, 2021
Jenna: Strapped at the Picnic Table
While on the road, the Headmaster pulls over and finds a secluded picnic area to give Jenna a much needed strapping.
Updated: Mon. Dec. 27, 2021
Daija: Hairstyling Tips
The Headmaster offers Daija haircare tips, first with his hand and then with a ping-pong paddle.
Updated: Fri. Dec. 24, 2021
Angelina: Dress Code Violations
Poor Angelina is still figuring out this complicated dress code situation. She is given a long painful punishment with yardstick and hand on her bare bottom, with a dash of ruler on her feet to remind her about proper footwear.
Updated: Wed. Dec. 22, 2021
Daija: No Whining!
Daija is called into the Headmaster's private executive office to discus her poor attitude and continual whining. Stubbed toe or not, she will be punished. The Headmaster bends her over his desk for a bottom blistering dose of the wooden paddle.
Updated: Mon. Dec. 20, 2021
Daija: School Girl Beat Down
Daija the school girl is given a long painful punishment with strap and paddle. She is reduced to screams, sobs and begging.
Updated: Fri. Dec. 17, 2021
Jenna: OTK and On-All-Fours
Jenna is given an early before bed spanking by the Headmaster. He starts with some hard OTK and finishes with her on-all-fours on the coffee table.
Updated: Wed. Dec. 15, 2021
For missing her curfew time, a very flexible Brooke is giving a traditional Murgha punishment by the Headmaster.
Updated: Mon. Dec. 13, 2021
Daija & Brooke: Not Making the Bed
When the Headmaster discovers the girl's bedroom and bed to be a complete mess, he punishes them both with a wooden paddle.
Updated: Fri. Dec. 10, 2021
Jenna: Naked OTK in the Bedroom
Jenna waits naked on the edge of her bed. The Headmaster enters and, without a word, pulls her over his knee and gives her a long hard OTK hand-spanking. He then sends her to bed sobbing.
Updated: Wed. Dec. 08, 2021
Daija: Progress Report
Daija is invited into the Headmaster's private office to discuss her progress at life. Although she has made undeniable gains, there is still room for improvement. In the spirit of personal growth and self-improvement, the Headmaster bends her over the desk and beats her bare bottom with a wooden paddle.
Updated: Mon. Dec. 06, 2021
Amber: OTK, Hand and Paddle
Amber receives a preemptive punishment to help with her attitude. The Headmaster punishes her OTK with hand and wooden paddle.
Updated: Fri. Dec. 03, 2021
Bridget: Runaway Beat Down (Part 3)
Bridget has run away from the Academy and the Headmaster is forced to search the streets for her. When he finds her, punishment is swift and painful. In part three, Bridget is sent naked to the punishment room for some intensive strap work.
Updated: Wed. Dec. 01, 2021
Bridget: Runaway Beat Down (Part 2)
Bridget has run away from the Academy and the Headmaster is forced to search the streets for her. When he finds her, punishment is swift and painful. In part two, the punishment in the van continues. Once they return to the Academy, Bridget's punishment continues with ping-pong paddle, hairbrush and leather strap. She is then sent down to the punishment room.
Updated: Mon. Nov. 29, 2021
Bridget: Runaway Beat Down (Part 1)
Bridget has run away from the Academy and the Headmaster is forced to search the streets for her. When he finds her, punishment is swift and painful. In part one, the Headmaster takes the belt to her right where he finds her.
Updated: Fri. Nov. 26, 2021
Daija: School Girl, OTK Hand Spanking
The Headmaster gives Daija a bare bottom OTK hand spanking in her school girl uniform.
Updated: Wed. Nov. 24, 2021
Jenna: Before-Bed Inspection and Hand-Spanking
Jenna is given a before-bed rubber glove inspection and an OTK hand-spanking on her already very red and sore bare bottom by the Headmaster.
Updated: Mon. Nov. 22, 2021
Daija Receives a Maintenance Spanking in the Bathroom
The Headmaster generously makes time from his busy schedule to give a hard hand spanking in the bathroom to help keep the wayward girl on the path of discipline and proper behavior. Standing, but bent over with her hands on the floor, she is quickly reduced to sobbing as the Headmaster applies corrective negative reinforcement.
Updated: Fri. Nov. 19, 2021
Abigail: Dungeon Odyssey
The Headmaster decides new girl Abigail could benefit from a trip to his dungeon. With Daija assisting, a terrified Abigail is put on knees and elbows and is given a healthy dose of the paddle. Much crying and redness ensues.
Updated: Wed. Nov. 17, 2021
Brooke and Daija: Forbidden Fun (Part 2)
The Headmaster catches Daija and Brooke playing with a very large dildo. Bad girls! In part 2, the Headmaster props each girl up on-all-fours on a bench and paddles them both with a heavy wooden paddle.
Updated: Mon. Nov. 15, 2021
Brooke and Daija: Forbidden Fun (Part 1)
The Headmaster catches Daija and Brooke playing with a very large dildo. Bad girls! He puts Daija over his knee for a hard OTK punishment.
Updated: Fri. Nov. 12, 2021
Brooke: High Heels, Hair Brush and Paddle
The Headmaster is not pleased with Brooke's 'street walker' outfit. He works hard to improve her fashion sense with a long painful punishment that includes hand, hairbrush and wooden paddle, and finishes with Brooke completely naked.
Updated: Wed. Nov. 10, 2021
Daija: Paddled in front of Shay and Lynn
Daija fails to send naked and kneeling new girl Shay to the punishment room. Instead she spends the time chatting with Shay and Lynn. The Headmaster is not amused and paddles Daija's bare bottom with the ping pong paddle in front of the other two girls.
Updated: Mon. Nov. 08, 2021
Pretty new girl Mila, continues her transition into life at the Academy. Naked and kneeling on the floor, she is lectured by the Headmaster. She then goes over his knee for a long hand-spanking. The Headmaster finishes her orientation with a taste of the ruler on her shapely pink bottom.
Updated: Fri. Nov. 05, 2021
Amber & Daija: Punished School Girls (Part 2)
Amber and Daija, already tender and sobbing from their earlier paddling, are further punished by the Headmaster with hand and hairbrush.
Updated: Wed. Nov. 03, 2021
Amber & Daija: Punished School Girls (Part 1)
Amber and Daija, in their school girl uniforms, are punished together by the Headmaster with hand and heavy wooden paddle.
Updated: Mon. Nov. 01, 2021
Angelina: Caught Stealing!
The Headmaster finds a new ring in Angelina's bag and immediately suspects she is stealing again. He confronts her on it and, under the Headmaster's skillful interrogation, she quickly confesses to stealing the valuable ring. The long arm of justice descends upon the troublesome girl in the form of a painful hairbrush spanking. First with her kneeling on the floor next to the bed and then, in an increasing state of undress, she is ordered onto-all-fours on the bed.
Updated: Wed. Oct. 27, 2021
Daija: Daily Chat
Daija and the Headmaster sit down together for their daily chat. Unfortunately for Daija, the Headmaster does most of his talking with the ping Pong paddle.
Updated: Mon. Oct. 25, 2021
Jenna: Hard Strapping
As Jenna's grades continue to suffer due to her out of control drinking, the Headmaster heroically attempts to modify the troubled young girl's behavior through careful and selective negative reinforcement. She is sent to her room to strip and assume the appropriate position on-all-fours on the bed to receive a long hard strapping.
Updated: Fri. Oct. 22, 2021
Daija: Hard Strapping and Tears
Daija sits waiting for the Headmaster, his heavy leather strap in her hands. The Headmaster enters the room, orders her to bare her bottom and then bends her over the arm of the couch. She then receives a hard painful strapping that leaves her screaming and sobbing in pain.
Updated: Wed. Oct. 20, 2021
Amber: Haibrush on the Ottoman
Amber, in her best school girl uniform, is made to kneel on the ottoman in an exposed and humiliating position. The Headmasters gives her a very painful hairbrush spanking. She is left well marked and sobbing.
Updated: Mon. Oct. 18, 2021
Daija: The Five Minute Spanking
The Headmaster lectures Daija about her repeated failings to do even the simplest office work. He follows this up with a five minute hard OTK hand-spanking briskly delivered to a fully nude Daija.
Updated: Fri. Oct. 15, 2021
Lynn: Late for Appointment
When Lynn keeps the Headmaster waiting for her scheduled appointment, he punishes her with a wooden paddle, OTK.
Updated: Wed. Oct. 13, 2021
Daija: Tattletale Paddling
The Headmaster bends Daija over the arm of the couch, her elbows on the floor, bares her bottom, and paddles her for being a tattletale.
Updated: Mon. Oct. 11, 2021
Brooke: Ready for Bed
Brooke, dressed for bed in her long nightgown, is given an extended before-bed punishment by the Headmaster that includes hand and paddle.
Updated: Fri. Oct. 08, 2021
© Alpine Entertainment Group Inc. 2009