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Miss Ruby Marks

1,190 Clips

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1,227 Followers

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Gambler's Dilemma (Shot in 4K)

Gambler's Dilemma (Shot in 4K)

Gambler's Dilemma (Shot in 4K)

4/9/26 3:40 AM•29 min•7697 MB•mp4•4k

Price$28.99 USD

CategoryGames

Related CategoriesBlouse Fetish,Bruises,Classic Caning,Femdom,Paddling

KeywordsCorporal Punishment,Bruises,F/m Domination,Humiliation,Bastinado,Paddling,Sjambok,Caning,Strapping,Hand Tawsing,Satin Blouse,Pencil Skirt,Stilettoes,Mistress Scarlet Graves,House Of Graves

PerformersMiss Ruby Marks, Miss Scarlet Graves, Kevin Caned

Description

kevin has been caught gambling after informing me he couldn't possibly afford an amazing experience at The Day Of Dominance - but then it becomes clear he can, he'd just rather gamble his money away at the racing track instead. So I tell Mistress Scarlet Graves of his transgressions and We present him with a challenge - the gambler's dilemma ... he must guess a number between 1 and 18 (the roll of 3 dice) which is the number of strokes he will receive and then another number will be thrown to decide what implement we use. Will kevin ever win the gamble?

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clips with Mistress Scarlet Graves

sinful sissy in latex lust

circus puppy play

chastity training - full length

prissy princess program - full length

sissy school - full length

Sent to The Sissy Circus (Full length)

a prissy sissy spanking

fucked, fisted and fingered

becky's wake up call

roasting rosie

a slutty spitroast

the bedroom boot bitch

trained and purged

Dr Graves Prosthetic Pussy Clinic

a prissy sissy roast
caught in the act

clips with Madam M:

stable boy swirly

soaped and stroked but not in the way they hoped

Deloused and Locked In The Cells

Wellie Weigh In

Cock Locked, Mouth Wide Open

Clips with Miss Anna Elite

Slutty kitchen slave fucked all over the room

epic pantyhose denial

painfully punished by his stepmum and her hot friend

Clips with The Hunteress:

Double Domme, Double Discipline

Becky Bends Over For Some Extra Motivation

Beat Him Til He Screams

Bought & Broken In

Captured & Contained

Prison Guard Brutality

Clips with Mistress Baton:

soaped and swirlied

sweaty pits post punishment denial

filled and fucked across the room

locked forever in pantyhose denial

Judicial Justice

Prisoner 971 spread and spanked

No wanking in jail!

kevin vs the carpet beater

A merciless mouthsoaping

Worshipping The Polar ends Of Perfection

Fisted & Face Slapped

The Witches Revenge

Dressed for destruction

gerry vs ALL the carpet Beaters

Bastinado brings her to tears

Suffering For sadists

gerry vs ALL the carpet beaters

whipped and welted

caned to her senses

peggy's pain and punishment

Alexia Vs 2 Corporal Caners

Bruising Up her Backside

Sadistic Stripes

Breaking The Brat

2 Teachers 1 Tawse and 1 Very Naughty School Girl

18 Strokes To Break Him

Clips with Miss Suzanna Maxwell:

Filled With Dick, Fisted and Fed Our Feet On The Bed

Spitroast sacrifice

Double Trouble Wedgie edging

Lust For Our Leather

Cruel Canes & Luscious Leather

Caned For His incompetence

Wicked Wellie Worship

Spitroasting The Stable Boy

Reverse Penectomy Ruin

Micro Penis Clinic Consultation

Milked By Three

A Face full Of Cum

Filthy Cocksucker Gets whipped

Busted Until he drops

Three Whips To Make Them Beg

Ballbusting Competition: Bust Off the Rematch

Boys Dont Get To Breathe

Pissing On The Spitroast

Sissy Hunters - fridays catch

Sissy Hunters part 2

Made To Suck Off the Stallion

Fired Or Fucked

Barefoot Destruction

Starved Of Oxygen and kicked In The Balls

Whipped In His Tiny Cock and Covered In Spit

Demoted To Our Ashtray

Whipped In the prison

Imprisoned In a cell of pain

Specimen of failure

31 Kicks to the Balls

Stomped In The Cock and Balls Until He's Hard

2 Boys Fucked face to face

A Fearsome flogging

Trampled By the Pool

Drying Our Feet On the Slave

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