Introducing Jenny
Introducing Jenny. The Headmaster commands Jenny to get over his knee. She knows what it is…
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Emma’s Exams
Emma's Exams. The Headmaster is dismayed when he sees the results of Emma's exams and he…
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Bad Party
Bad Party. We see Laura and Claire lying in a jumble, still in their uniforms, in…
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The Last Word In Sex
The Last Word In Sex. 4 Stars for The Last Word in Sex!-AVNShot entirely in Paris…
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Zettai Kanojo 2 vol.2
Zettai Kanojo 2 vol.2. In the future, the world becomes dominated by men. An epidemic rises…
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Juku
Juku. Juku from Caribbeancom Studios features a 'mature' Japanese starlet named Sayaka Takase. Sayaka has just…
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First Caning For Claire
First Caning For Claire. New resident Claire rudely enters the Headmaster's office without knocking first. Headmaster…
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Yoru Banana Exercise 2
Yoru Banana Exercise Vol. 2. Caribeancom is extremely excited to bring you another sweet installment of…
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Inattentive
Inattentive. Dana is so busy reading that she sits down on a chair without noticing Headmaster…
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Panties and Masturbation: Mercedes
Panties and Masturbation: Mercedes. Mercedes is a sexy Canadian schoolgirl who loves the look and feel…
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Amaenbou Vol.13
Amaenbou Vol.13. Yukina Mori has always had the fortune of being born into a lifestyle of…
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Invitation
Invitation. Mr. Lewis has grown sick and tired of constantly having to punish Angie. But she…
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Late Night Punishment
Late Night Punishment. Headmaster Tom brusquely pulls up Jenny's coat as she kneels on all fours…
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Family Reunion (Digital Sin)
Family Reunion (Digital Sin). Culled from the widely successful Tabu Tales series from Digital Sin comes…
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Wet Tobacco
Wet Tobacco. We see Annie, the Headmaster's assistant, enter the room. She takes a packet of…
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Oni Iki Toransu 9
Oni Iki Toransu 9. Caribbeancom is very pleased to present Oni iki Toransu 9! In this…
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Tsubaki Myuu no Ichinichi Kanshoukai
Tsubaki Myuu no Ichinichi Kanshoukai. Camellia Myuu is a celebrated sexpot in Japan. And one glance…
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The New Teacher
The New Teacher. Headmaster Tom needs to hire a new assistant teacher.The first respondent is too…
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Shirouto Hakkutsujijyou Honmono! Onna Janshi
Shirouto Hakkutsujijyou Honmono! Onna Janshi. Caribbeancom is very happy to introduce you to Airi Kagura. Airi…
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Bad Reports
Bad Reports. Mr. Lewis is berating Tina and Lizzie for having the worst end of month…
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Shirouto Hakkutsujijyou Honmono! Cabin Attendant
Shirouto Hakkutsujijyou Honmono! Cabin Attendant. The producers at Caribbeancom have been scouring far and wide to…
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6 Girls Punishment
6 Girls Punishment. The girls expected some nice, quiet Easter days. But the first day of…
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Take Good Care
Take Good Care. Rose is in trouble again. She is waiting nervously for Headmaster Tom to…
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