Tag Archives: Older Woman / Younger Women

Ceclia had never been spanked before today, and now it is time for her *first* ever caning. She’s not sure what to expect, and her poor, unconditioned bottom is already …

A painful caning viewed in full from four angles! Dear Prudence has done it again! Ever the troublemaker, this little miscreant will endure a day-long punishment for all the school …

Cecilia returns to my office for her second punishment of the day. Holding out her tender palms, she receives three stinging swats from my tawse on each of her naughty …

Dear Prudence has done it again! Ever the troublemaker, this errant student is back in my office, and I am tired of it. This little miscreant will endure a day-long …

Cecilia enters my office for her first ever spanking. Her ample bottom bruises quickly under my heavy leather strap, and a relentless punishment leaves her with dark purple marks. Poor …

Dear Prudence (Mila Grant) has done it again! Ever the troublemaker, this errant student is back in my office, and I am tired of it. This little miscreant will endure …

Matilda is supposed to be doing her homework, but when her Governess comes to check on her progress she tries to hide in the wardrobe. Unimpressed, her Governess grabs her …

Miss Suzanna Maxwell and Miss Ruby Marks are really the most beautiful of sadists – stunning in their mini skirts and satin blouses, they stand before a bratty, young lady …

Miss Mathews reports significant improvement in the girls’ classwork, but there is still room for improvement. Looking darling and innocent in their fresh pink pyjamas, these four wayward students will …

Veronica just doesn’t do well with the pain. Each stroke of my cane makes her shriek and shake in agony, and I am not entirely sure she can make it …