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‘headmaster’ stories

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Headmaster Lucas

A headmaster uses chastity to reform troubled young women.

by dothemath in Fetish 12/19/2023
H
4.67
16.1k
27
3
56
0

The Caged Student Ch. 01

A stepfather discovers his ward is up to no good.

by StrappingMan in Mind Control 12/14/2023
4.3
16.4k
9
3
38

Lisa, Scott and Me Pt. 06

We get summoned to the Headmaster’s study.

by DDorset53 in Gay Male 09/25/2023
H
4.71
4.9k
10
3
12

My Son's a Bully?!

Only one way to resolve the matter...

by PURE_GAY_FICTION_STORIES in Gay Male 08/25/2023
4.43
31k
54
16
110
0

The Perverted Headmaster Ch. 02

Sweetie finds herself in Veddons office once again.

by Craptastic_Invalid in NonConsent/Reluctance 07/23/2023
4.23
13.5k
10
0
16

A Risk has Consequences Pt. 01

Overconfident Nicki takes a risk too many!

by duke1951 in Group Sex 06/22/2022
4.41
11.6k
9
1
32

Tuition

Mom pays tuition for her son's benefit.

by yellowjacket66 in Loving Wives 05/19/2022
3.86
32.4k
23
6
40
0

Langley Circle Beginning Ch. 17

They show him just how nasty they can be!

by wafflingman in Novels and Novellas 03/09/2022
H
4.64
4k
4
2
9

Langley Circle Beginning Ch. 05

She reports to headmaster for her punishment.

by wafflingman in Novels and Novellas 02/04/2022
H
4.6
6.9k
7
3
12

Langley Circle Beginning Ch. 01

Roleplay in school uniform is just the beginning.

by wafflingman in Novels and Novellas 01/27/2022
H
4.61
15.9k
20
5
59

Gordy Gets a Skirt Ch. 04

Gordy goes to finishing school to eradicate maleness.

by KristaMorane in Transgender & Crossdressers 11/02/2021
4.46
9.1k
6
3
9

Headmasters' Harem: Candice

Candice offers herself to Dr. Kinny.

by LittleKay in Fetish 04/16/2021
H
4.62
16.6k
23
2
56
0

Headmasters' Harem: Lisa

Teacher Lisa is disciplined for the first time.

by LittleKay in Fetish 03/06/2021
4.18
21.3k
21
1
45
0

Taken by the Headmaster

Female teacher provokes Headmaster with painful consequences

by Sexykit in BDSM 11/21/2020
H
4.58
38.3k
28
6
46

Summoned by the Headmaster

Young female teacher is paddled for a dresscode violation.

by Sexykit in BDSM 11/10/2020
4.32
24.5k
10
4
17

A Student's Lesson

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

by StrappingMan in Novels and Novellas 05/18/2020
4.07
67.7k
36
3
76

Trouble at Greenway Academy

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

by MALIBUMAN666 in Incest/Taboo 05/07/2019
4.32
41.6k
41
6
71
0

Icky Vicky Roberts

Headmaster makes young man his toy.

by JimBob44 in Gay Male 03/09/2019
H
4.64
32.3k
29
7
40
0

The Headmaster

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

by PaulieCelt in BDSM 03/07/2019
4.18
43.9k
14
5
23
0

Drug Check

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

by MALIBUMAN666 in Fetish 01/03/2019
4.48
17k
12
2
17
0

Discovering My Other Side

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

by janon314 in BDSM 12/01/2018
H
4.73
18.7k
14
6
23
0

The Twins at College

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

by MALIBUMAN666 in NonConsent/Reluctance 06/28/2018
4.2
82.5k
52
4
97
0

The Caring Headmaster...

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

by JOHNKEY2222 in BDSM 03/06/2018
4.49
28.9k
11
5
17
0

Jessica at the Finishing School Pt. 05

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

by MALIBUMAN666 in Incest/Taboo 06/01/2017
4.4
39.3k
34
1
49

Jessica at the Finishing School Pt. 03

Helen's schooling gets harder and harder...

by MALIBUMAN666 in NonConsent/Reluctance 05/26/2017
H
4.51
72.3k
36
0
47

Jessica at the Finishing School Pt. 01

Jessica finds her new headmaster is a devious man.

by MALIBUMAN666 in NonConsent/Reluctance 05/17/2017
4.41
123.6k
112
9
170

Jed Punishes Clover

Jed humiliates me for fucking Fred.

by clovermoffatt in NonConsent/Reluctance 08/08/2016
4.15
27k
6
2
14
0

The Adventures of Clover Ch. 04

Clover has to suck the Headmaster's hard cock.

by clovermoffatt in NonConsent/Reluctance 08/06/2016
4.12
36.3k
5
0
12

The Adventures of Clover Ch. 03

Clover is forced to suck the headmaster's cock.

by clovermoffatt in NonConsent/Reluctance 08/04/2016
4.08
35.6k
7
0
11

Clover Watches Jed fuck Miss Akin

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

by clovermoffatt in Erotic Couplings 07/30/2016
4.17
24.1k
7
2
14
0

Tabatha's Taboo

The college slut learns a lesson from the head.

by MisterRe in BDSM 10/15/2015
4.34
32.7k
17
3
28
0

Out For A Walk Ch. 01

Brother is amazed at what he sees.

by Scot1234 in Incest/Taboo 05/04/2015
4.28
118k
62
5
78

Greenwood Academy Ch. 01

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

by kiradarkwinter in NonConsent/Reluctance 05/02/2015
H
4.5
75.1k
58
5
76
0

The Headmaster and the Pupil

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

by irisheyesgirl in BDSM 09/19/2014
H
4.61
75.9k
32
2
40
0

Lexie's Adventures

A wild girl at boarding school.

by Mysteria27 in Incest/Taboo 05/30/2014
3.84
49.3k
27
0
29
0

Daddy, Lily and Headmaster Ch. 03

Still no suitable punishment...

by Lilytoy in Incest/Taboo 05/14/2014
4.18
103.8k
36
5
49

Daddy, Lily and Headmaster Ch. 02

The punishment continues...

by Lilytoy in Incest/Taboo 05/10/2014
4.23
109.5k
55
4
66

Daddy, Lily and Headmaster

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

by Lilytoy in Incest/Taboo 05/07/2014
4.46
259.5k
224
12
288

Fiona Gets Called In To School

Nigel helps arrange Fiona's summons to the headmaster

by MILowner in NonConsent/Reluctance 11/26/2013
4.35
114.7k
35
1
58

The Chinese Mahogany Desk

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

by TheTallDarkTruth in NonConsent/Reluctance 04/21/2013
4.26
259.8k
187
11
255
0

Kate's Story Ch. 01

Kate is caught and sent to see the Headmaster.

by Robert_Anthony in NonConsent/Reluctance 11/21/2012
4.46
121.4k
92
6
111
0

Six of the Best Ch. 02

The Headmaster and the habitually-wayward 'Justine'.

by KinoKe in BDSM 10/10/2012
4.36
23.4k
1
3
1

Six of the Best

A special session in The Headmaster's study.

by KinoKe in BDSM 09/26/2012
4.32
40k
8
4
11

Yes, Headmaster

A college girl has called her University's Headmaster.

by Literalist in Letters & Transcripts 10/15/2011
4
24.2k
1
0
2
0

Lucia Gets Spanked

She plays into his strongest fantasy.

by jennanips in BDSM 07/01/2011
4.33
43.5k
22
2
23
0

Mary Carson's Punishment

Schoolgirl Gets Spanked by Headmaster.

by Lissette in BDSM 06/28/2011
4.04
61.6k
9
3
13
0

Halloween Costume

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

by storyteller_no_9 in Incest/Taboo 05/13/2011
4.05
278.3k
76
7
122
0

Inspection

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

by MALIBUMAN666 in NonConsent/Reluctance 01/13/2011
4.14
184k
47
6
79
0

Called to the Headmaster's Office

When you flaunt the rules, you get punished.

by edgeofdesire in BDSM 12/29/2010
4.3
82.7k
15
4
21
0

The Program Ch. 01-06

Headmaster trains innocent scholarship student.

by IdeeFixee in BDSM 06/30/2009
H
4.54
148.6k
90
3
157

Wale of a Tail Ch. 04

Jennifer finds justice.

by BasilBasset in BDSM 02/22/2009
3.74
19.8k
000

Wale of a Tail Ch. 02

Jennifer is faced with a choice.

by BasilBasset in NonConsent/Reluctance 02/20/2009
3.49
38.3k
0
1
1

The Head Master and the Panties

What if they get caught?

by Misslexia in Fetish 10/31/2008
4.38
53.3k
10
3
14
0

Gentlemen's Club Ch. 04

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

by Ywashere in Gay Male 07/02/2008
4.49
119.7k
30
1
35

A Very Naughty Girl Indeed!

A headmaster teaches you the error of your ways.

by Jonathan Phillips in BDSM 01/28/2007
4.45
164.4k
52
11
61
0

Little Miss Perfect & The Headmaster

Errant schoolgirl gets her comeuppance.

by bbwsweetstuff in BDSM 02/20/2006
4.27
114.4k
38
5
53
0

The Headmaster

When will she learn to stop talking back?

by amethyst wind in BDSM 04/14/2004
4.22
54.9k
6
2
11
0

Daddy's Darlin' Ch. 06

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

by FuckDoll in NonConsent/Reluctance 04/29/2003
4.32
446.8k
80
5
86

Daddy's Darlin' Ch. 05

Darlin' goes to 'school'.

by FuckDoll in NonConsent/Reluctance 04/27/2003
4.29
438.8k
88
5
98

Dorm Room Inspection

Headmaster disciplines a student.

by Benoni in NonConsent/Reluctance 12/25/2002
H
4.52
541.4k
285
0
323
0

Sexy Schoolgirls

They go to the club for fun and get it.

by Mag58 in Exhibitionist & Voyeur 09/01/2002
4.26
133.3k
14
4
25
0
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