Headmaster Fetish Videos & Clips
I'm Headmaster, and I specialize in the art of corporal punishment. I love the feel of a bare bottom during a session of hard caning or a long bout of paddling.
Whether it's a scene involving a school uniform or a roleplay centered on domestic discipline, I keep things strict. I enjoy the intensity of otk spanking and the sting of tawsing. My work often features classic spanking and vintage spanking styles that leave a mark.
I'm a fan of strapping and the way it complements a session of sex and spanking. For those who like it a bit more focused, I provide pussy spanking and pussy slapping.
From a schoolgirl in a classroom to a spanked wife at home, I make sure the discipline is proper. I'm Headmaster, and I'm here to deliver a classic caning you won't forget.
Headmaster Fetish Videos & Clips
I'm Headmaster, and I specialize in the art of corporal punishment. I love the feel of a bare bottom during a session of hard caning or a long bout of paddling.
Whether it's a scene involving a school uniform or a roleplay centered on domestic discipline, I keep things strict. I enjoy the intensity of otk spanking and the sting of tawsing. My work often features classic spanking and vintage spanking styles that leave a mark.
I'm a fan of strapping and the way it complements a session of sex and spanking. For those who like it a bit more focused, I provide pussy spanking and pussy slapping.
From a schoolgirl in a classroom to a spanked wife at home, I make sure the discipline is proper. I'm Headmaster, and I'm here to deliver a classic caning you won't forget.
Headmaster XXX Latest Videos
Late Again For School 1080p WMV For Media Player
10/4/26 3:39 AM•11 min•914 MB•wmv•1080p
Late Again For School 1080p WMV For Media Player
10/4/26 3:39 AM•11 min•914 MB•wmv•1080pPrice$17.99 USDCategoryCaningRelated CategoriesOtk Spanking,School Uniform,Spanking,Spanking M/F,StrappingKeywordsSchoolgirl,School Punishments,Corporal Punishments,Spanking,Otk Spanking,Caning,Spanking M/f,School Uniforms,Spanked Schoolgirls,Strapping,Paddling,Schoolgirls,School Spankings,Corporal Punishment,Hard CaningPerformersHeadmaster, Rachel Lloyd, Annie WilsonDescriptionFeaturing: Annie Wilson as Annie, Rachel Lloyd as Paula and Steve Bickerstaff as Mr Barton the Headmaster
Strict Headmaster Mr. Barton summons two mischievous sixth-form girls, Annie and Paula, to his study after the local sweet-shop owner reports them for stealing.
He orders Annie to bend over the desk and raise her skirt. A long, hard, bare-bottom hand spanking follows, sharp, loud smacks that turn her soft cheeks a vivid, glowing red while she yelps and squirms. Paula then receives the same thorough treatment, her bottom thoroughly roasted until it matches Annie’s in colour and heat.
Both girls are made to stand side-by-side with hands on their heads, skirts still raised, their bright red, stinging bottoms fully on display while the Headmaster lectures them for embarrassing the school. He warns that any further trouble will bring a far more severe punishment.
Thoroughly chastened, the two girls leave the study rubbing their sore, blazing bottoms.
Text by Mistress Eleise
Video Information
The video "Late Again For School (2002)" is a short erotic corporal punishment film written, directed and produced by Cliff James.
Please note this clip is from the Top Marks Video Archives, the quality is not up to the HD standard of videos produced today
Maid For Spanking 1080p WMV For Media Player
9/27/26 10:13 AM•11 min•1124 MB•wmv•1080p
Maid For Spanking 1080p WMV For Media Player
9/27/26 10:13 AM•11 min•1124 MB•wmv•1080pPrice$16.99 USDCategorySpankingRelated CategoriesCaning,Hair Brush Spanking,Mature,Otk Spanking,UniformsKeywordsSpanking,M/f Spanking,Spanked Wife,Big Bottom,Strapping,Corporal Punishment,Punished Maid,Paddling,Bare Botttom,Hand Spanking,Domestic Discipline,Uniforms,Maid,Mature,Jean BradleyPerformersHeadmaster, JeanDescriptionFeaturing: Jean Bradley as The Wife and Steve Bickerstaff as The Husband
After complaining about poor service — cold plates, soggy feet and not enough of a smile — Steve decides his wife Jean needs proper correction. He bends her over the table, lifts her skirt and delivers a firm, thorough bare-bottom hand spanking.
Her soft cheeks quickly turn a glowing red under his stinging palm. She gasps and admits it feels “quite nice... a bit stinging,” clearly enjoying the heat building across her bottom.
He continues the spanking on the bed, then switches to an implement that cracks sharply and leaves a deeper, hotter sting. Her bottom grows increasingly red and warm as she squirms, moans and encourages him to keep going.
By the end her cheeks are hot, well-spanked and thoroughly marked, both of them openly enjoying the long, playful session.
Text by Mistress Eleise
The video "Maid For Spanking" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
Please note: This clip is from the Top Marks Video Archives. The quality is not up to the HD standard of videos produced today.
Night Howls 1080p WMV For Media Player
9/24/26 8:44 AM•12 min•1645 MB•wmv•1080p
Night Howls 1080p WMV For Media Player
9/24/26 8:44 AM•12 min•1645 MB•wmv•1080pPrice$19.99 USDCategorySpankingRelated CategoriesCaning,Otk Spanking,School Uniform,Spanking M/F,StrappingKeywordsHeadmaster Spanking,Bare Bottom Spanking,Leather Strap Punishment,Schoolgirl Uniform,Mature Student,Over The Desk,Sit-spot Strapping,Panties Down,Strict Discipline,Detention Spanking,School Office Punishment,Skirt Up Spanking,Evening DetentionPerformersHeadmaster, JoJoDescriptionFeaturing: JoJo Mooney as Miss June Johnson and Steve Bickerstaff as Mr. Barton the Headmaster.
Headmaster Mr Barton sat alone in his dimly lit office at Waterhouse Moor, already regretting the evening classes. Then Miss Johnson walked in, a mature student who had barely attended Italian, now dressed in full school uniform: white blouse, short grey pleated skirt, knee socks and black shoes, the outfit clinging to her curvaceous figure.
He treated the costume as the invitation it was. Skirt up, white cotton panties yanked to her knees, her plump bare bottom presented over the oak desk. A long, hard hand spanking turned those cheeks a stinging pink while he scolded her for wasted lessons and the insult of the uniform. Then came the heavy leather strap, crack after crack across her sit-spots and the backs of her thighs until her backside and upper legs were swollen, welted and a deep angry red.
He left her standing face to the wall, hands on her head, skirt still raised, to think about how a grown woman who plays the schoolgirl is punished like one.
Text by Mistress Eleise
Video Information
The video "Night Howls" is a short erotic corporal punishment film written, directed and produced by Cliff James.
Please note: This video is from the archives and is not up to the standard of today's HD clips.
The Witnesses 1080p WMV For Media Player
9/18/26 11:28 AM•11 min•808 MB•wmv•1080p
The Witnesses 1080p WMV For Media Player
9/18/26 11:28 AM•11 min•808 MB•wmv•1080pPrice$17.99 USDCategoryCaningRelated CategoriesHair Brush Spanking,Otk Spanking,Spanking,Spanking M/F,StrappingKeywordsSpanking,M/f Spankings,Caning,Domestic Discipline,Hand Spanking,Strapping,Tawsing,Secretary,Bare Bottom Caning,Punishment Caning,Real Tears,Cane Marks,Cane Stripes,Bottom Marks,Red BottomPerformersHeadmaster, Mr Foxton, Rachel Lloyd, Monica, Vicky, SarahDescriptionFeaturing: Therese as the bratty Victoria, Steve Bickerstaff as Marcus Wesley-Jones, Rachel Lloyd as Debbie Wesley-Jones, Monica Rose as the secretary and John Rundell as Marcus's boss Mr Foxton
Secretary Monica has just been caned. Marcus Wesley-Jones returns to his conversation with his boss, Mr Foxton, when his stepdaughter Victoria bursts in, complaining that her stepmother has spanked and caned her.
Marcus asks why. Once he hears the reason and sees the evidence, he tells her she deserved every stroke and that he will add a hard caning of his own.
* * * Previously * * *
Debbie takes a call from the headmistress: Vicki has been swearing, misbehaving and drawing pornographic pictures in art class. Shown the drawings, Debbie is horrified.
Spare the rod and spoil the girl is her motto. She puts Vicki over for a hard spanking and strapping over her tight jeans, then fetches a crook-handle cane. Knickers down, Vicki receives a severe bare-bottom caning followed by a thorough over-the-knee spanking.
A two-part discipline clip: a stepmother’s fierce home punishment, then a stepfather who decides the lesson is not finished.
Text by Mistress Eleise
Video information
The Video "The Witnesses" (2003) is a short erotic corporal punishment film written and directed by Cliff James.
Please note this clip is from the Top Marks Video Archives; the quality is not up to the HD standard of videos produced today.
- 9/16/26 5:58 AM•18 min•5028 MB•mp4•1440p

A Rude Awakening 1440p MP4
9/16/26 5:58 AM•18 min•5028 MB•mp4•1440pPrice$25.99 USDCategoryCaningRelated CategoriesPaddling,Pussy Slapping,Spanking,Spanking M/F,StrappingKeywordsDomestic Discipline,Caning,M/f Spankings,Sex And Spanking,Spanking,Pussy Slapping,Pussy Teasing,Whipping,Pussy Spanking,Nurse's Uniform,Classic Caning,Cane Marks,Cane Stripes,Bottom Marks,Red BottomPerformersHeadmaster, JeanDescriptionFeaturing Jean Bradley and Steve Bickerstaff
Steve finishes a long evening disciplining his wife and his shoulder is aching. He calls for his favourite naughty nurse. Jean arrives in a tight white uniform, ready to oblige.
A gentle massage is only the start. Steve decides the shoulder needs a proper test and produces a collection of implements. Jean climbs onto the bed on all fours and presents her bottom.
He begins with a flexible whip, laying on crisp, stingy strokes that soon have her pushing back for more. A heavier leather strap follows, each thwack making her cheeks bounce until they glow a deep rosy red.
Then comes the cane. Six good strokes, hard and sharp, leave vivid marks across her already sore flesh. Jean takes them with a mix of gasps and laughter.
By the end her bottom is on fire. Steve rubs the striped cheeks and she grins: sore, but very nice. Next time, she says, it might be her turn to test that shoulder.
Text by Mistress Eleise
The video "A Rude Awakening" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
This clip is from the Top Marks Video Archives. Please note that the quality is not up to the HD standard of videos produced today.
The Caning of Jean Bradley 1080p MP4
9/13/26 12:24 PM•10 min•604 MB•mp4•1080p
The Caning of Jean Bradley 1080p MP4
9/13/26 12:24 PM•10 min•604 MB•mp4•1080pPrice$15.99 USDCategoryCaningRelated CategoriesClassic Caning,Mature,Pussy Slapping,Spanking,StrappingKeywordsDomestic Discipline,Caning,M/f Spankings,Sex And Spanking,Spanking,Strapping,Tawsing,Pussy Slapping,Pussy Spanking,Classic Spanking,Nurse's Uniform,Cane Marks,Red Bottom,Bare Bottom,Bottom MarksPerformersHeadmaster, JeanDescriptionFeaturing Jean Bradley and Steve Bickerstaff
The Caning of Jean Bradley - Part Two of A Rude Awakening
aturday morning. Steve wants a lie-in. Instead his wife Jean wakes him in a tiny white nurse’s uniform — unbuttoned, seamed stockings, stilettos, and a long crook-handled rattan cane in her hand. “Doctor’s orders.”
The game flips. Jean is soon face-down across the bed, bare, gripping the pillow. Steve takes the cane.
The first stroke cracks across her bottom. She gasps; he teases. Stroke after stroke follows — some “nice,” some vicious — while they banter through it: work medicals, bruises she’ll have to hide, whether he’s getting better with the cane. She laughs, then yelps. He rubs her burning cheeks when she begs, then starts again.
One last dozen. Hard. Jean’s bottom is a mass of hot red and purple stripes. She calls him cruel; he tells her she’s loving it. Final three: keep still. She tries. She doesn’t quite manage.
When it ends he stands back and inspects the welts, fingers tracing the marks. She pants that her bottom will never be the same. He kisses her shoulder. “You took that beautifully. Good girl.”
Consensual marital caning: nurse-uniform role-play that turns into a long, talky, increasingly severe bare-bottom caning on the bed.
Text by Mistress Eleise
Video Information
The video "The Caning of Jean Bradley" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
Please note this clip is from the Top Marks Video Archives, the quality is not up to the HD standard of videos produced today
No Breakfast For Steve 1080 WMV For Media Player
9/13/26 8:04 AM•22 min•3179 MB•mp4•1080p
No Breakfast For Steve 1080 WMV For Media Player
9/13/26 8:04 AM•22 min•3179 MB•mp4•1080pPrice$34.99 USDCategorySpankingRelated CategoriesCaning,Otk Spanking,Pussy Slapping,Spanking M/F,StrappingKeywordsCaning,Domestic Discipline,M/f Spankings,Paddling,Strapping,Pussy Slapping,Pussy Spreading,Otk Spankings,Hairbrush Spanking,Mature,Hard Punishment,Pussy Spanking,Cane Marks,Marks,Bottom MarksPerformersHeadmaster, SarahDescriptionFeaturing: Sally Cavender as The Lazy Wife, Steve Bickerstaff as The Irate Husband
Steve arrives home expecting the full English breakfast he requested. Instead he finds his wife Sally packing a beach bag, more interested in an afternoon of sunbathing with her girlfriend than in feeding her hard-working husband.
His patience snaps. He hauls her across his lap, yanks down her shorts and knickers, and delivers a long, hard bare-bottom hand spanking that quickly turns her soft cheeks a deep, glowing red.
A heavy leather strap follows, cracking repeatedly across the already sore flesh and raising wide, burning bands. Still not satisfied, Steve bends her over the sofa arm and gives her six precise, painful strokes of the cane, leaving vivid raised welts.
Finally he spreads her thighs and turns the strap on her exposed pussy, delivering sharp, stinging strokes directly to the tender lips until they are swollen, flushed and throbbing.
By the end Sally is left bent over, bottom and pussy thoroughly marked and burning, with a clear warning that next time breakfast will be ready.
Text by Mistress Eleise
Video Information
The video "No Breakfast For Steve" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
Please note: This clip is from the Top Marks Videos archives. As it is a vintage recording, the quality is not up to the HD standard of videos produced today.
Secretary Monica's Embarrassing Lesson 1080p WMV For Media Player
9/7/26 11:48 AM•15 min•2062 MB•wmv•1080p
Secretary Monica's Embarrassing Lesson 1080p WMV For Media Player
9/7/26 11:48 AM•15 min•2062 MB•wmv•1080pPrice$26.99 USDCategoryCaningRelated CategoriesClassic Caning,Otk Spanking,Spanking,Spanking M/F,StrappingKeywordsSpanking,M/f Spanking,Classic Spanking,Paddling,Caning,Otk Spanking,Strapping,Humiliation,Secretary,Domestic Discipline,Hard Caning,Spanked Secretary,Punishment Caning,Vintage Spanking,Classic CaningPerformersHeadmaster, Mr Foxton, Rachel Lloyd, Monica, VickyDescriptionFeaturing
Monica Rose as the secretary
Steve Bickerstaff as Marcus Wesley Jones
Rachel Lloyd as Debbie Wesley Jones
Therese as the bratty step-daughter Vicki
John Rundell as Mr. Foxton
After caning his wife Debbie to a well-striped, sobbing finish, Marcus turns his attention to the smug secretary Monica, who has been watching with open amusement. On Mr. Foxton’s orders, Monica is ordered to lower her knickers and present herself beside the still-punished Debbie.
Marcus first delivers a thorough, hard bare-hand spanking that quickly turns Monica’s pale bottom a bright, burning pink. He then straps her with his heavy leather belt, raising thick welts across her cheeks, before finishing her with a severe eighteen-stroke caning. By the end, Monica is left bent over the sofa, bottom swollen and thoroughly marked, sobbing and thoroughly humbled in front of both her boss and Debbie.
Text by Mistress Eleise
Video Information
The video "Secretary Monica's Embarrassing Lesson" (2002) is a short erotic corporal punishment film written, directed and by Cliff James.
- 9/3/26 5:02 AM•9 min•4036 MB•mp4•1080p

The Witnesses 1080p MP4
9/3/26 5:02 AM•9 min•4036 MB•mp4•1080pPrice$17.99 USDCategoryCaningRelated CategoriesClassic Caning,Otk Spanking,Spanking,Spanking F/M,StrappingKeywordsSpanking,M/f Spankings,Caning,Domestic Discipline,Hand Spanking,Strapping,Tawsing,Secretary,Hard Caning,Humiliation,Caned Secretary,Bare Bottom Caning,Punishment Caning,Real Tears,TearsPerformersHeadmaster, Mr Foxton, Rachel Lloyd, Monica, Vicky, Sarah, Susan, Sam Johnson, Teresa MayDescriptionFeaturing:
Therese as the bratty Victoria
Steve Bickerstaff as Marcus Wesley-Jones
Rachel Lloyd as Debbie Wesley-Jones
Monica as the secretary
John Rundell as Marcus's boss Mr Foxton
Secretary Monica has just been caned. Marcus Wesley-Jones returns to his conversation with his boss, Mr Foxton, when his stepdaughter Victoria bursts in, complaining that her stepmother has spanked and caned her.
Marcus asks why. Once he hears the reason and sees the evidence, he tells her she deserved every stroke and that he will add a hard caning of his own.
Previously
Debbie takes a call from the headmistress: Vicki has been swearing, misbehaving and drawing pornographic pictures in art class. Shown the drawings, Debbie is horrified.
Spare the rod and spoil the girl is her motto. She puts Vicki over for a hard spanking and strapping over her tight jeans, then fetches a crook-handle cane. Knickers down, Vicki receives a severe bare-bottom caning followed by a thorough over-the-knee spanking.
A two-part discipline clip: a stepmother’s fierce home punishment, then a stepfather who decides the lesson is not finished.
Text by Mistress Eleise
Video information
The Video "The Witnesses" (2003) is a short erotic corporal punishment film written and directed by Cliff James.
Please note this clip is from the Top Marks Video Archives; the quality is not up to the HD standard of videos produced today.
- 9/2/26 11:47 AM•11 min•6422 MB•mp4•1440p

Two Spanked Girls 1440p MP4
9/2/26 11:47 AM•11 min•6422 MB•mp4•1440pPrice$19.99 USDCategorySpankingRelated CategoriesCaning,Otk Spanking,Spanking F/F,Spanking M/F,StrappingKeywordsLesbians,Domestic Discipline,Paddling,Strapping,Sex And Spanking,Pussy Slapping,Pussy Spreading,Otk Spankings,Hairbrush Spanking,Pussy Spanking,Hot Wives,Classic Spanking,Vintage Spanking,M/f Spanking,F/f SpankingPerformersHeadmaster, Sarah, SusanDescriptionFeaturing
Sally Cavender as Sally
Steffie as Stephanie
Steve Bickerstaff as Sally’s husband Steve.
Steve comes home early and finds his wife Sally and her girlfriend Stephanie naked in the bedroom, spanking and paddling each other’s bare bottoms after a bout of playful lesbian fun.
Furious, he orders both women to the front room. The punishment has a humiliating twist: he will spank and strap them himself, and they will be made to punish each other while he watches.
Steve puts each girl over his knee in turn for a hard bare-bottom hand spanking that quickly turns their cheeks a burning pink. Then comes the heavy leather strap, laid on with powerful strokes until both bottoms are hotter, redder and marked.
The real sting is what follows. Sally must bend Stephanie over the sofa and strap her already sore cheeks. Stephanie is then ordered to return the favour on Sally. Steve directs every stroke as the two naked women reluctantly spank and strap one another, bottoms bouncing under the leather.
By the end both girls are glowing a deep fiery red, covered in handprints and thick strap marks, whimpering through the humiliation of punishing their best friend’s tender, quivering backside.
Text by Mistress Eleise
Video Information:
The video "Two Spanked Girls" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James, owner of Top Marks Videos.
- 9/1/26 2:14 PM•10 min•5445 MB•mp4•1440p

Two Caned Girls 1440p MP4
9/1/26 2:14 PM•10 min•5445 MB•mp4•1440pPrice$16.99 USDCategoryCaningRelated CategoriesClassic Caning,Otk Spanking,Spanking,Spanking M/F,StrappingKeywordsSpanking,M/f Spanking,Paddling,Strapping,Pussy Spanking,Group Spanking,Hard Caning,M/f Caning,Classic Spanking,Domestic Discipline,Group Caning,Vintage Spanking,Cmnf,Haed Caning,Caned GirlsPerformersHeadmaster, Sarah, SusanDescriptionFeaturing
Sally Cavender as Sally
Steffie as Stephanie
Steve Bickerstaff as Steve
After catching his wife Sally and her girlfriend Stephanie eagerly spanking and paddling each other’s bare bottoms, Steve is furious. He orders both naughty girls to bend over the sofa side by side, their plump, bare bottoms thrust out invitingly, for a severe caning.
With his long, whippy rattan cane, Steve delivers hard, stinging strokes that make both girls gasp, yelp, and squirm desperately. The cane bites deeply into their soft, bouncing cheeks, leaving vivid red welts as he thoroughly punishes their bare bottoms.
This is a very strict and highly charged domestic discipline scene with plenty of scolding, a long hard caning, and two very sore, glowing red bottoms by the end.
Highly recommended for fans of husband-led punishment and naughty wives getting exactly what they deserve on their bare bottoms!
Text by Mistress Eleise
Video Information:
The video “Two Caned Girls” (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
- 8/29/26 4:41 AM•11 min•1572 MB•mp4•1080p

Maid For Spanking 1080p MP4
8/29/26 4:41 AM•11 min•1572 MB•mp4•1080pPrice$19.99 USDCategorySpankingRelated CategoriesCaning,Hair Brush Spanking,Otk Spanking,Spanking M/F,StrappingKeywordsSpanking,M/f Spanking,Spanked Wife,Big Bottom,Strapping,Corporal Punishment,Punished Maid,Paddling,Bare Botttom,Hand Spanking,Domestic Discipline,Uniforms,Maid,Mature,Jean BradleyPerformersHeadmaster, JeanDescriptionFeaturing
Jean Bradley as The Wife
Steve Bickerstaff as The Husband
After complaining about poor service — cold plates, soggy feet and not enough of a smile — Steve decides his wife Jean needs proper correction. He bends her over the table, lifts her skirt and delivers a firm, thorough bare-bottom hand spanking.
Her soft cheeks quickly turn a glowing red under his stinging palm. She gasps and admits it feels “quite nice... a bit stinging,” clearly enjoying the heat building across her bottom.
He continues the spanking on the bed, then switches to an implement that cracks sharply and leaves a deeper, hotter sting. Her bottom grows increasingly red and warm as she squirms, moans and encourages him to keep going.
By the end her cheeks are hot, well-spanked and thoroughly marked, both of them openly enjoying the long, playful session.
Text by Mistress Eleise
The video "Maid For Spanking" (2002) is a short erotic corporal punishment film written, directed and produced by Cliff James.
