‘headmaster’ stories

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headmaster 

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Headmaster Lucas

A headmaster uses chastity to reform troubled young women.

H
4.66
14.7k
25
3
55
0

The Caged Student Ch. 01

A stepfather discovers his ward is up to no good.

4.28
15.2k
9
3
36

Lisa, Scott and Me Pt. 06

We get summoned to the Headmaster’s study.

H
4.71
4.8k
11
3
13

My Son's a Bully?!

Only one way to resolve the matter...

4.42
30.2k
54
16
109
0

The Perverted Headmaster Ch. 02

Sweetie finds herself in Veddons office once again.

4.21
13.1k
9
0
15

A Risk has Consequences Pt. 01

Overconfident Nicki takes a risk too many!

4.39
11.5k
9
1
32

Tuition

Mom pays tuition for her son's benefit.

3.86
32.1k
22
6
38
0

Langley Circle Beginning Ch. 17

They show him just how nasty they can be!

H
4.64
3.9k
4
2
9

Langley Circle Beginning Ch. 05

She reports to headmaster for her punishment.

H
4.6
6.8k
7
3
12

Langley Circle Beginning Ch. 01

Roleplay in school uniform is just the beginning.

H
4.61
15.6k
20
5
58

Gordy Gets a Skirt Ch. 04

Gordy goes to finishing school to eradicate maleness.

4.46
9k
6
3
9

Headmasters' Harem: Candice

Candice offers herself to Dr. Kinny.

H
4.61
16.5k
23
2
55
0

Headmasters' Harem: Lisa

Teacher Lisa is disciplined for the first time.

4.18
21.1k
21
1
45
0

Taken by the Headmaster

Female teacher provokes Headmaster with painful consequences

H
4.58
37.8k
28
6
46

Summoned by the Headmaster

Young female teacher is paddled for a dresscode violation.

4.32
24.3k
9
4
15

A Student's Lesson

A senior agrees to 'tutoring' from an old professor.

4.07
67.4k
36
3
77

Trouble at Greenway Academy

Clara is singled out for special attention at Greenway...

4.32
41.4k
41
6
71
0

Icky Vicky Roberts

Headmaster makes young man his toy.

H
4.64
32.2k
29
7
40
0

The Headmaster

A desperate mother tries to atone for her son's misbehavior.

4.18
43.7k
14
5
21
0

Drug Check

When a College Master instigates a drug check programme...

4.48
16.9k
12
2
18
0

Discovering My Other Side

A woman discovers something she's kept hidden for years.

H
4.73
18.7k
13
6
22
0

The Twins at College

Sheltered twins at a new school get a rude awakening...

4.2
82.3k
52
4
98
0

The Caring Headmaster...

Naughty new school master's Wife meets the headmaster...

4.48
28.7k
11
5
17
0

Jessica at the Finishing School Pt. 05

The visitors arrive, and so does someone unexpected...

4.4
39.2k
34
1
50

Jessica at the Finishing School Pt. 03

Helen's schooling gets harder and harder...

H
4.51
72k
36
0
48

Jessica at the Finishing School Pt. 01

Jessica finds her new headmaster is a devious man.

4.41
123.2k
111
9
169

Jed Punishes Clover

Jed humiliates me for fucking Fred.

4.15
26.9k
6
2
14
0

The Adventures of Clover Ch. 04

Clover has to suck the Headmaster's hard cock.

4.12
36.2k
5
0
12

The Adventures of Clover Ch. 03

Clover is forced to suck the headmaster's cock.

4.08
35.5k
7
0
11

Clover Watches Jed fuck Miss Akin

Clover is coerced into sucking cock but then gets a treat.

4.17
24.1k
7
2
14
0

Tabatha's Taboo

The college slut learns a lesson from the head.

4.34
32.7k
17
3
28
0

Out For A Walk Ch. 01

Brother is amazed at what he sees.

4.28
117.8k
61
5
78

Greenwood Academy Ch. 01

Georgiana is sent to Greenwood Academy and meets Mr. Jordan.

H
4.5
74.8k
58
5
76
0

The Headmaster and the Pupil

A boarding school girl runs afoul of her Headmaster...

H
4.61
75.7k
32
2
40
0

Lexie's Adventures

A wild girl at boarding school.

3.84
49.2k
27
0
29
0

Daddy, Lily and Headmaster Ch. 03

Still no suitable punishment...

4.18
103.5k
36
5
50

Daddy, Lily and Headmaster Ch. 02

The punishment continues...

4.23
109.2k
55
4
67

Daddy, Lily and Headmaster

Lily has been a naughty girl, Daddy sees the headmaster.

4.46
258.7k
222
12
284

Fiona Gets Called In To School

Nigel helps arrange Fiona's summons to the headmaster

4.35
114.4k
35
1
58

The Chinese Mahogany Desk

Naughty schoolgirl gets her punishment on Mr Anderson's desk.

4.26
259k
185
11
254
0

Kate's Story Ch. 01

Kate is caught and sent to see the Headmaster.

4.46
121.1k
91
6
110
0

Six of the Best Ch. 02

The Headmaster and the habitually-wayward 'Justine'.

4.36
23.3k
1
3
1

Six of the Best

A special session in The Headmaster's study.

4.32
39.9k
8
4
11

Yes, Headmaster

A college girl has called her University's Headmaster.

4
24.1k
1
0
2
0

Lucia Gets Spanked

She plays into his strongest fantasy.

4.33
43.5k
22
2
23
0

Mary Carson's Punishment

Schoolgirl Gets Spanked by Headmaster.

4.04
61.5k
9
3
13
0

Halloween Costume

Daddy critiques her party costume. He likes it. A lot.

4.05
277.8k
76
7
120
0

Inspection

Girl is sent to 'college' to learn her place.

4.15
183.4k
47
6
79
0

Called to the Headmaster's Office

When you flaunt the rules, you get punished.

4.3
82.5k
15
4
21
0

The Program Ch. 01-06

Headmaster trains innocent scholarship student.

H
4.54
148.2k
90
3
157

Wale of a Tail Ch. 04

Jennifer finds justice.

3.74
19.8k
000

Wale of a Tail Ch. 02

Jennifer is faced with a choice.

3.49
38.3k
0
1
1

The Head Master and the Panties

What if they get caught?

4.38
53.2k
10
3
14
0

Gentlemen's Club Ch. 04

Naughty 18-year-old boys get caught by headmaster.

4.49
119.5k
30
1
35

A Very Naughty Girl Indeed!

A headmaster teaches you the error of your ways.

4.45
164.3k
52
11
61
0

Little Miss Perfect & The Headmaster

Errant schoolgirl gets her comeuppance.

4.27
114.2k
38
5
53
0

The Headmaster

When will she learn to stop talking back?

4.22
54.8k
6
2
11
0

Daddy's Darlin' Ch. 06

Sarah's first day at her new school is a long one.

4.33
446.2k
80
5
86

Daddy's Darlin' Ch. 05

Darlin' goes to 'school'.

4.29
438.2k
88
5
98

Dorm Room Inspection

Headmaster disciplines a student.

H
4.52
540.7k
285
0
322
0

Sexy Schoolgirls

They go to the club for fun and get it.

4.26
133.3k
14
4
24
0
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