Mature Women Spanking Boys

Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up...
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...
Dressy mature gives legjob to a boy and gets banged thru ripped open tights
Dressy mature gives legjob to a boy and gets banged thru ripped open tights
18 y.o. boy practices tit-licking and pussy-fingering on his sexy mature teacher
18 y.o. boy practices tit-licking and pussy-fingering on his sexy mature teacher
Naughty mature slut playing with her toy boy
Naughty mature slut playing with her toy boy
Phoenix Marie earns the title of Anal Queen. This incredibly sexy women with an amazing ass...
Phoenix Marie earns the title of Anal Queen. This incredibly sexy women with an...
Skinny boy gets his cock blown by a charming mature slut while taking a bath
Skinny boy gets his cock blown by a charming mature slut while taking a bath
Cock-loving boy changes into womens clothes eager for a strapon butt ride
Cock-loving boy changes into womens clothes eager for a strapon butt ride
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Naughty mature slut having sex with her toy boy
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Lustful mature seductress pleases a boy with some real nasty hardcore fucking
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Mistress Shila spanks mature slave
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Sleepy boy pushing aside mature babes panties to free her ripe wet pussy
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Horny mature slut fucking and sucking a toy boy
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Naughty mature slut fucking her toy boy on the couch
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Raunchy mature in pink undies fools with a toy before fucking a nerdy boy
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up...
Hot to trot delivery boy jug fucks and pussy pounds a chubby mature chick
Hot to trot delivery boy jug fucks and pussy pounds a chubby mature chick
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Greedy bathroom-pig Connor is perched in a grungy stall in the public bathroom anxiously...
Greedy bathroom-pig Connor is perched in a grungy stall in the public bathroom...
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Naughty mature slut fucking a toy boy in the garden
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Real black mature women
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Nasty mature housewife eyeing a young cocky boy aching for intense dicking
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Naughty mature slut getting fucked by her toy boy
Phoenix Marie earns the title of Anal Queen. This incredibly sexy women with an amazing ass...
Phoenix Marie earns the title of Anal Queen. This incredibly sexy women with an...
Hot, mature women, private pictures
Hot, mature women, private pictures
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked and gang...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked...
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Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend Yuki Mori is...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend...
We have many beautiful women come through WhippedAss.com, Chanel Preston is at the top of the...
We have many beautiful women come through WhippedAss.com, Chanel Preston is at the top...
Otk on the couch. Woman on woman. Brunette spanking blonde. We always like to see how women...
Otk on the couch. Woman on woman. Brunette spanking blonde. We always like to see how...
This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
Hot mature lady gets punished and spanked hard
Hot mature lady gets punished and spanked hard
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked and gang...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend Yuki Mori is...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend...
Amber Rayne is back domming and has Kiera King as her pet. Ambers new plaything is brought down...
Amber Rayne is back domming and has Kiera King as her pet. Ambers new plaything is...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has never been...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has...
Mellanie Monroe gets turned on by kinky bondage sex and takes hard punishment from Nika Noire....
Mellanie Monroe gets turned on by kinky bondage sex and takes hard punishment from...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has never been...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has...
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li purposely...
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li...
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This weeks update is a new style of interactive femdom putting YOU in the hot seat! Have you...
This weeks update is a new style of interactive femdom putting YOU in the hot seat!...
Cherry Torn is finally settling down and marrying the man of her dreams while her bridesmaids...
Cherry Torn is finally settling down and marrying the man of her dreams while her...
Black girl feels blondies ass and remarks how hot it is. Now the brown ass is otk. She tries to...
Black girl feels blondies ass and remarks how hot it is. Now the brown ass is otk. She...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked and gang...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked...
Welcome MILF star Anjanette Astoria to WhippedAss.com. In this women in prison role play update...
Welcome MILF star Anjanette Astoria to WhippedAss.com. In this women in prison role...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired beauty...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired beauty...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are...
This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has never been...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has...
This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend Yuki Mori is...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has never been...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires...
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This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
Savannah Fox returns for more spanking, punishment, fisting, deep anal and extreme squirting in...
Savannah Fox returns for more spanking, punishment, fisting, deep anal and extreme...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with...
Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up...
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Brawny and brash, Eros Sin is just another insolent, ungrateful young football star failing all...
Brawny and brash, Eros Sin is just another insolent, ungrateful young football star...
Never before on ANY fem dom site have you seen such a blatant form of male humiliation until...
Never before on ANY fem dom site have you seen such a blatant form of male humiliation...
Parker London may be a sight for sore eyes but does he have what it takes to be a sex slave to...
Parker London may be a sight for sore eyes but does he have what it takes to be a sex...
Liza Del Sierra gets caught flirting with her professors husband. Chanel Preston spanks and...
Liza Del Sierra gets caught flirting with her professors husband. Chanel Preston...
Liza Del Sierra gets caught flirting with her professors husband. Chanel Preston spanks and...
Liza Del Sierra gets caught flirting with her professors husband. Chanel Preston...
Welcome back Yuki Mori! Lorelei Lee has been at war in Afghanistan while her girlfriend Yuki...
Welcome back Yuki Mori! Lorelei Lee has been at war in Afghanistan while her...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired beauty...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired...
Cherry Torn is finally settling down and marrying the man of her dreams while her bridesmaids...
Cherry Torn is finally settling down and marrying the man of her dreams while her...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked and gang...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked...
This storyline was a request made by a member named yooli. Thanks, yooli for the suggestion!...
This storyline was a request made by a member named yooli. Thanks, yooli for the...
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The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked and gang...
The moment we have all been waiting for is here! On Halloween Sinn Sage gets spanked...
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei Lee....
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei...
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei Lee....
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei...
What happens when you pluck a cute, innocent girl right out of Golden Gate Park and bring her to...
What happens when you pluck a cute, innocent girl right out of Golden Gate Park and...
Leashed boy gets decent spanking before being allowed to lick dommes pussy
Leashed boy gets decent spanking before being allowed to lick dommes pussy
This week, our Boy DT, aka Deep Threat, aka Greedy got out of the pen and we decided to set him...
This week, our Boy DT, aka Deep Threat, aka Greedy got out of the pen and we decided...
Welcome the devastating Mistress Francesca Le to Divine Bitches! Francesca may be new to Divine...
Welcome the devastating Mistress Francesca Le to Divine Bitches! Francesca may be new...
In this weeks comedic but tough fantasy roleplay storyline Madeline plays an ex prostitute...
In this weeks comedic but tough fantasy roleplay storyline Madeline plays an ex...
Our eastern European expeditions continue with Mistress Lorelei Lee at an old meat factory in...
Our eastern European expeditions continue with Mistress Lorelei Lee at an old meat...
What the fuck is this small cock gonna do for me, pretty boy? Mistress Harmony is relentless in...
What the fuck is this small cock gonna do for me, pretty boy? Mistress Harmony is...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired beauty...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are...
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei Lee....
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires...

More Spanking Galleries

Lefty thought he was a lucky fucker when Samantha Sin walked onto the set to team up with...
Mistress Sandra Romains command of the male anatomy is made painfully clear as she casually...
Two naughty boys doing a horny chubby huge breasted mature lady
Cherry Torn is finally settling down and marrying the man of her dreams while her bridesmaids...
We have many beautiful women come through WhippedAss.com, Chanel Preston is at the top of the...
Cherry Torn is finally settling down and marrying the man of her dreams while her bridesmaids...
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li purposely...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
Welcome back Yuki Mori! Lorelei Lee has been away in the army while her girlfriend Yuki Mori is...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
After 4 years we welcome back Annie Cruz to Whipped Ass! This time the tables are turned and...
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li purposely...
Welcome Zoe Voss to Whipped Ass! Zoe, a tall, fair skinned, all natural, red-haired beauty...
Famous pornstar Asa Akira subs for the very first time at WhippedAss.com! Asa has never been...
Welcome MILF star Anjanette Astoria to WhippedAss.com. In this women in prison role play update...
Welcome MILF star Anjanette Astoria to WhippedAss.com. In this women in prison role play update...
Cherry Torn is finally settling down and marrying the man of her dreams while her bridesmaids...
This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot movies....
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li purposely...
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei Lee....
Involved in a DS relationship with her boss Lily Cade, smart ass masochist, Mia Li purposely...
Hot blonde AJ Applegate finds herself under the control of dominatrix Goddess Lorelei Lee....
In the dungeon of her own mind, Syren de Mer confesses her incessant sexual desires and her...
Luscious mature babe bares her rack and opens her pussy for a sheepish boy
Dressed up mature gal showing a delivery boy her sucking and fucking skills
Slim-legged mature blonde gets fingered and dicked by a horny next-door boy
Greedy mature gal takes advantage of a drunken boy eager to taste his meat
Stacked mature fatty feeds her ripe melons to a boy and gets pussy fisted
Stacked mature fatty feeds her ripe melons to a boy and gets pussy fisted
Louise and Mindy are fat mature women with massive butts taking turns in slobbering a meaty cock
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