Boys Underpants Spanking

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18 year old Sam Truitt gets the punishment that such a young man deserves in this hot domestic...
18 year old Sam Truitt gets the punishment that such a young man deserves in this hot...
18 year old Sam Truitt gets the punishment that such a young man deserves in this hot domestic...
18 year old Sam Truitt gets the punishment that such a young man deserves in this hot...
asian femdom spanking bad boys
asian femdom spanking bad boys
Ariel X has been named the newest director of Ultimate Surrender while Darlings been tooting her...
Ariel X has been named the newest director of Ultimate Surrender while Darlings been...
This girl is hot, hot, fucking hot. She is tall, blonde, pretty face, nice ass and great tits....
This girl is hot, hot, fucking hot. She is tall, blonde, pretty face, nice ass and...
Welcome 19 year old year old Yhivi to Whipped Ass. In this kinky roleplay fantasy Yhivi has a...
Welcome 19 year old year old Yhivi to Whipped Ass. In this kinky roleplay fantasy...
Even when she is sleeping she is hot she was wearing these little blue underpants. Her whole ass...
Even when she is sleeping she is hot she was wearing these little blue underpants. Her...
This weeks update is the edited version of the live show from last week with the cute and tough...
This weeks update is the edited version of the live show from last week with the cute...
Lazy teen stripping off to gets punished with painful ass spanking from a naughty guy
Lazy teen stripping off to gets punished with painful ass spanking from a naughty guy
ALL HAIL PRINCESS DONNA!! Its her birthday and she is out to test the perverted loyalties of her...
ALL HAIL PRINCESS DONNA!! Its her birthday and she is out to test the perverted...
When our spanking Master and Mistress are in the room to punish, their victim did something...
When our spanking Master and Mistress are in the room to punish, their victim did...
Welcome 19 year old year old Yhivi to Whipped Ass. In this kinky roleplay fantasy Yhivi has a...
Welcome 19 year old year old Yhivi to Whipped Ass. In this kinky roleplay fantasy...
Hot blistered butts and well striped cheeks - severe spanking and paddling
Hot blistered butts and well striped cheeks - severe spanking and paddling
Various pencil arworks of spanking and flogging
Various pencil arworks of spanking and flogging
Whipped Ass would like to wish you a Happy Halloween with this weeks special, Sins Of The Flesh....
Whipped Ass would like to wish you a Happy Halloween with this weeks special, Sins Of...
Slave applicant Kristine Kahill is tied to the cross and offered up to the Brunch guests.Slave...
Slave applicant Kristine Kahill is tied to the cross and offered up to the Brunch...
Cute teen lowers her panties and spreads her ass cheeks - blistering spanking - hot tears
Cute teen lowers her panties and spreads her ass cheeks - blistering spanking - hot...
Trust fund brat, Penny Pax is a control freak. Day after day she tortures her maids by making...
Trust fund brat, Penny Pax is a control freak. Day after day she tortures her maids by...
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Tyron cant keep herself out of trouble. This time, its serious. Both our spanking Master and...
Tyron cant keep herself out of trouble. This time, its serious. Both our spanking...
Barra just started her work out routine when her spanking Mistress decided she wanted some...
Barra just started her work out routine when her spanking Mistress decided she wanted...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Marie Luv makes her debut on Whipped Ass! Bella Rossi puts this hardbody whos built for sex...
Marie Luv makes her debut on Whipped Ass! Bella Rossi puts this hardbody whos built...
Jenna Rose and Maddy Marks try Spanking
Jenna Rose and Maddy Marks try Spanking
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Miela finds herself at the mercy of our spanking Master yet again. Admittedly, hes much more...
Miela finds herself at the mercy of our spanking Master yet again. Admittedly, hes...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Welcome Alisha Adams to Whipped Ass and Lea Lexis our hot and evil Romanian domming for the...
Welcome Alisha Adams to Whipped Ass and Lea Lexis our hot and evil Romanian domming...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be challenged...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and looking to...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and...
Bonnie Day, a petite local masochist who likes lesbian sex and punishment has her work cut out...
Bonnie Day, a petite local masochist who likes lesbian sex and punishment has her work...
Yet again, Ines has to be disciplined. It seems our spankings have no effect on his dark haired...
Yet again, Ines has to be disciplined. It seems our spankings have no effect on his...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
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Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be challenged...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be...
No one likes a lazy bitch roaming around their house. Even if shes as hot as the lazy bitch in...
No one likes a lazy bitch roaming around their house. Even if shes as hot as the lazy...
This weeks update is the edited version of the live show from last week with the cute and tough...
This weeks update is the edited version of the live show from last week with the cute...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Newcomer Ella Nova gets destroyed in this high energy role play scenario about a massage...
Newcomer Ella Nova gets destroyed in this high energy role play scenario about a...
Katrina Jade enjoys rough sex and punishment in her personal life. She comes to the Armory to...
Katrina Jade enjoys rough sex and punishment in her personal life. She comes to the...
Carissa Montgomery is a gorgeous MILF who pushed her boundaries in this sadistic lesbian update....
Carissa Montgomery is a gorgeous MILF who pushed her boundaries in this sadistic...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
Live Show Mondays brings you part 2 of the June live show that featured Princess Donna, Jame...
Live Show Mondays brings you part 2 of the June live show that featured Princess...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Mielas back just healed from her last spanking. Thats good enough reason to mark it up again.
Mielas back just healed from her last spanking. Thats good enough reason to mark it up...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
The House is renovating. Help us to take apart the Upper Floor doctrine and rebuild the...
The House is renovating. Help us to take apart the Upper Floor doctrine and rebuild...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and looking to...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
They can stay for awhile, but they have to earn it. One by one, she takes them over her knee,...
They can stay for awhile, but they have to earn it. One by one, she takes them over...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
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Jade gets put over her Princess knee and receives a hard OTK spanking for being a dirty little...
Jade gets put over her Princess knee and receives a hard OTK spanking for being a...
Barra has been a very naughty girl. Her spanking Master didnt even wait for us to record the...
Barra has been a very naughty girl. Her spanking Master didnt even wait for us to...
Voluptuous babes spanking their round asses
Voluptuous babes spanking their round asses
This weeks update is the edited version of the live show from last week with the cute and tough...
This weeks update is the edited version of the live show from last week with the cute...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be challenged...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be...
Penny Pax and Ella Nova get stuck in customs on their way back from a whirlwind trip to Panama....
Penny Pax and Ella Nova get stuck in customs on their way back from a whirlwind trip...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
Oh dear Katty. When will this beauty learn her lesson. Her spanking addiction keeps her coming...
Oh dear Katty. When will this beauty learn her lesson. Her spanking addiction keeps...
Already hog tied and sitting for her spanking Mistress to appear, Laura tries to prepare herself...
Already hog tied and sitting for her spanking Mistress to appear, Laura tries to...
The House is renovating. Help us to take apart the Upper Floor doctrine and rebuild the...
The House is renovating. Help us to take apart the Upper Floor doctrine and rebuild...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be challenged...
Welcome local model and masochist Bianca Stone to Whipped Ass. Bianca likes to be...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
She pulls one of the school girls across her knee and gives her a bare handed spanking, as her...
She pulls one of the school girls across her knee and gives her a bare handed...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
Every once in awhile we have a girl come through the doors that really likes to be degraded, I...
Every once in awhile we have a girl come through the doors that really likes to be...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
Lily Labeau, Aiden Starr, Juliette March, and Princess Donna star in this smoking hot Wiredpussy...
Lily Labeau, Aiden Starr, Juliette March, and Princess Donna star in this smoking hot...
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This weeks update is the edited version of the live show from last week with the cute and tough...
This weeks update is the edited version of the live show from last week with the cute...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than torturing...
You smell like fear, little boy. Nothing makes Mistress Aidens pussy more wet than...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and looking to...
Mz Berlin dominates two large breasted submissives. Lylith Lavey is new to BDSM and...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
things arent so joyous and lesbionic in this spanking video. Our spanking Mistress has found out...
things arent so joyous and lesbionic in this spanking video. Our spanking Mistress has...
Casey Calvert is an adorable all natural girl with a thirst for pain and this is her very first...
Casey Calvert is an adorable all natural girl with a thirst for pain and this is her...
We love inviting Katty for a spanking session. She loves being tied and is always prepared to...
We love inviting Katty for a spanking session. She loves being tied and is always...
Leonelle has been a very naughty girl. Her spanking Master has had enough.
Leonelle has been a very naughty girl. Her spanking Master has had enough.
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be challenged by...
Welcome local model Coral Aorta to Whipped Ass. Coral enjoys pain and likes to be...
This weeks update is the edited version of the live show from last week with the cute and tough...
This weeks update is the edited version of the live show from last week with the cute...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then Bella has...
Bella Rossi returns to sub on Whipped Ass for the first time in 4 years! Since then...
After catching Cry Baby drawing more inappropriate pictures, her teacher pulls her over her knee...
After catching Cry Baby drawing more inappropriate pictures, her teacher pulls her...
Have you ever heard of a caning competition? Well, the best way to be enlightened is to watch...
Have you ever heard of a caning competition? Well, the best way to be enlightened is...
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House dom Christian Wilde sits on his throne as Randall OReilly approaches, locked in chastity...
House dom Christian Wilde sits on his throne as Randall OReilly approaches, locked in chastity...
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Its time for another dungeon session. Muscular Master Nick plays with his handsome slave boy...
Its time for another dungeon session. Muscular Master Nick plays with his handsome slave boy...
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The Australian exchange program has placed Kelly in the USA. Shes free at last to fuck boys,...
The Australian exchange program has placed Kelly in the USA. Shes free at last to fuck boys,...
The Australian exchange program has placed Kelly in the USA. Shes free at last to fuck boys,...
Many have tried. Some have failed. Some made it through the final day of training. In this...
Many have tried. Some have failed. Some made it through the final day of training. In this...
Blake Daniels is blindfolded and in metal bondage. Tyler Saint takes him into a room of horny...
Blake Daniels is blindfolded and in metal bondage. Tyler Saint takes him into a room of horny...
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Kevin Case is a punk trying to get away with returning a skateboard that he thrashed in the...
Kevin Case is a punk trying to get away with returning a skateboard that he thrashed in the...
Presley Wright is brought into a balloon shop here in the Castro for a little fun. Hes bound and...
Presley Wright is brought into a balloon shop here in the Castro for a little fun. Hes bound and...
Its friday night here in San Francisco and the bar is standing room only! The crowd makes way as...
Its friday night here in San Francisco and the bar is standing room only! The crowd makes way as...
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