Some disciplinarians prefer to keep a lad at cane’s length during punishment. Miss James of School Mistress Fantasy, however, seems to prefer the close, personal approach.
With her naughty male student draped obediently over her thigh, she wraps one arm around his waist and uses the other to wield her favorite, whippy instrument of motivation.
While receiving discipline, a wise lad will resist every urge to peek up Miss James’ flowing skirt. To be caught in such a disrespectful act would result in horrible consequences — in front of the entire student body!
This serious matron knows exactly how to deal with misbehavior at the Boys Boarding School. First she orders the culprit to lower his trousers and then positions him atop his bed at the perfect horizontal level for her cane.
Taking her time and without a shred of mercy, she applies crimson welts from his gluteous minimus all the way down to his tender sit spot (which receives especially harsh attention).
No doubt the lad’s hard classroom chair will be even more uncomfortable than normal when he tries to sit down in the morning.
The mistress of the house doesn’t usually wear her riding outfit into the bedroom, unless she has a naughty little pony who needs to be broken. That procedure involves the subject’s naked flanks getting very well acquainted with the business end of her crop.
Thanks to Riding Boots for contributing another fantasy-provoking photograph. We suddenly have an urge to visit the local tack and saddle shop.
In her latest update, Miss Jessica hears strange noises coming from Mike’s office and walks in to find a spanking video playing on his computer. For wasting valuable office time, she sentences Mike to the very same punishment he was watching on the deviant video.
First Miss Jessica takes his trousers down and puts him over her knee for a firm hand spanking. Then she grabs a ruler from his desk and spanks him so hard that part of it actually snaps off.
After warning Mike to quit wiggling during his punishment, Miss Jessica bends him over a chair for some serious final smacks. That will teach him not to watch fetish porn at work!
Unfortunate JJ places his forearms on the desk and readies himself for a severe paddling from the voluptuous and extremely thorough Miss Betty. He’s going to be one very sorry young man after this serious lady blisters his bottom.
We’ve admired Miss Betty’s work for years — both as a Top and a bottom — and we have to say, we love her glamorous new look. Visit the Updates section at Women Spanking Men to see a much larger version of this classic photo.
Miss Lina has a painfully serious look in her eyes, the leather strap in her experienced hands, and she’s wearing her ever-so-short black spanking skirt, which means some unfortunate soul is going over her bare thighs for a good, old-fashioned whipping.
The only consolation is that the namesake of Lina’s House of Discipline has unbuttoned her blouse a bit, perhaps to give the condemned a brief glimpse of her cleavage before he’s bent over to face the carpet — and Miss Lina’s wrath.
