Tag Archives: Strict Headmistress

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 …

Both my teacher and student need to learn a lesson about respecting the headmistress! I reach for a birch bundle, driving the point home on Miss Montford’s bare bottom, before …

My four naughty students and their teacher have all taken two punishments with my cane, but their harsh lesson isn’t yet over. Bending shy and sore Melanie over, I administer …

The girls have been naughty again… and this time even with their teacher… carousing about town, and even inviting boys back home with them. Only a hard punishment will do! …

The girls have been naughty again… and this time even with their teacher… carousing about town, and even inviting boys back home with them. Only a hard punishment will do! …

The girls have been naughty again… and this time even with their teacher… carousing about town, and even inviting boys back home with them. Only a hard punishment will do! …

The girls have been naughty again… and this time even with their teacher… carousing about town, and even inviting boys back home with them. Only a hard punishment will do! …

The girls have been naughty again… and this time even with their teacher… carousing about town, and even inviting boys back home with them. Only a hard punishment will do! …