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Gritting his teeth as the Headmistress applies her cane

Gritting his teeth as the Headmistress applies her cane

11

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Thrashed for mouthing off to Miss Saddler

Thrashed for mouthing off to Miss Saddler

28

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Over stepping her authority

Over stepping her authority

33

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Thats where cheek gets you

Thats where cheek gets you

19

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Detention with Miss Atwell

Detention with Miss Atwell

26

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Caning the comedian

Caning the comedian

25

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Miss Atwell canes the bottom watchers

Miss Atwell canes the bottom watchers

26

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Thrashed on the bare bottom by Miss Atwell

Thrashed on the bare bottom by Miss Atwell

43

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The school mistresses knickers

The school mistresses knickers

42

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Sent to Miss James to be caned

Sent to Miss James to be caned

31

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Given the plimsol and strap by the headmistress

Given the plimsol and strap by the headmistress

25

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A good hard spanking over the headmistresses knee

A good hard spanking over the headmistresses knee

40

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Miss Rose; Slutty Teacher Satin Glove Masturbation

Miss Rose; Slutty Teacher Satin Glove Masturbation

54

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Sent to Miss James for the plimsol

Sent to Miss James for the plimsol

39

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Caned by his stepmom Miss James

Caned by his stepmom Miss James

37

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Sent to Miss Wood pt2 caned to tears

Sent to Miss Wood pt2 caned to tears

53

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Sent to Miss Wood pt1

Sent to Miss Wood pt1

44

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Watching the headmistresses bottom

Watching the headmistresses bottom

40

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Miss Lee; Ass Tease & Spreading For You To Cum All Over

Miss Lee; Ass Tease & Spreading For You To Cum All Over

45

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48

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Sent to the Headmistress pt1

Sent to the Headmistress pt1

30

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Repeatedly caned by Miss James

Repeatedly caned by Miss James

93

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Sent to Miss James

Sent to Miss James

66

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The long list of offences in Miss Yorks office

The long list of offences in Miss Yorks office

55

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The cheater and Miss Grangers wrath pt 2

The cheater and Miss Grangers wrath pt 2

122

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The cheater and Miss Grangers wrath pt 1

The cheater and Miss Grangers wrath pt 1

77

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Pretty Teacher Miss LaLay Strips While Playing With Worn Gym Panties

Pretty Teacher Miss LaLay Strips While Playing With Worn Gym Panties

63

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Making Peaches dance on the end of the tawse

Making Peaches dance on the end of the tawse

195

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The broken cane

The broken cane

101

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Caned across her bare bottom for smoking

Caned across her bare bottom for smoking

115

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Pretty Essie Peeps On Matron Kay While She Masturbates

Pretty Essie Peeps On Matron Kay While She Masturbates

84

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Sexy Miss Page Begs You To Stop Tickling Her Nylon Feet

Sexy Miss Page Begs You To Stop Tickling Her Nylon Feet

170

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No mercy for naughty Peaches

No mercy for naughty Peaches

49

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Caned after having her hands tawsed

Caned after having her hands tawsed

72

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Peaches the potty mouth caned

Peaches the potty mouth caned

108

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In front of Headmistress Granger pt2

In front of Headmistress Granger pt2

235

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In front of Headmistress Granger pt1

In front of Headmistress Granger pt1

105

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Cute Pixiee Plays With Miss Lee’s Big Bouncy Boobs

Cute Pixiee Plays With Miss Lee’s Big Bouncy Boobs

100

100%

Cute Lily Peeps On Sexy Headmistress Mackenzie In Stockings

Cute Lily Peeps On Sexy Headmistress Mackenzie In Stockings

113

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Cute Bex & Sexy Miss Cooper Compare Their Legs In Sheer Stockings

Cute Bex & Sexy Miss Cooper Compare Their Legs In Sheer Stockings

112

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Ordeal in the Headmistresses office pt3

Ordeal in the Headmistresses office pt3

94

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Ordeal in the Headmistresses office pt2

Ordeal in the Headmistresses office pt2

89

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Ordeal in the Headmistresses office pt1

Ordeal in the Headmistresses office pt1

292

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Sexy Miss Ray Masturbates While Wearing Latex Gloves

Sexy Miss Ray Masturbates While Wearing Latex Gloves

80

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Expert cheek giver pt2

Expert cheek giver pt2

49

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Sent to deputy Headmistress Hall

Sent to deputy Headmistress Hall

61

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Pretty Essie Gets Caught Smoking By Strict Matron Kay

Pretty Essie Gets Caught Smoking By Strict Matron Kay

87

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84

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Sexy Lucy & Miss Leah Tease You As They Strip & Dangle Their High Heels

Sexy Lucy & Miss Leah Tease You As They Strip & Dangle Their High Heels

73

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The sweep stake pt2

The sweep stake pt2

77

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Naughty Pixiee Plays A Prank & Makes Pretty Miss LaLay Strip In Class

Naughty Pixiee Plays A Prank & Makes Pretty Miss LaLay Strip In Class

133

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Lose Yourself In My Blue Grey Eyes While You Edge Your Cock

Lose Yourself In My Blue Grey Eyes While You Edge Your Cock

131

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Sexy Miss Page Strips While Playing With Headmistress’s Satin Clothing

Sexy Miss Page Strips While Playing With Headmistress’s Satin Clothing

116

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Truancy caning by Miss Hall

Truancy caning by Miss Hall

99

100%

Sent to Miss Hall for truancy

Sent to Miss Hall for truancy

77

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Sexy Miss Tolman Knows You Are Peeping On Her As She Strips

Sexy Miss Tolman Knows You Are Peeping On Her As She Strips

155

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Sexy Ivy & Pretty Miss Thompson Make You Stroke Your Cock

Sexy Ivy & Pretty Miss Thompson Make You Stroke Your Cock

98

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Touch his toes for being late

Touch his toes for being late

100

100%

Sent to Miss Wood

Sent to Miss Wood

183

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Report to the deputy Headmistress for caning

Report to the deputy Headmistress for caning

106

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