Spanking Bad Boys

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...
Lily Lane is bored to death unpacking candles day in and day out. Things at her job start to get...
Lily Lane is bored to death unpacking candles day in and day out. Things at her job...
Lily Lane is bored to death unpacking candles day in and day out. Things at her job start to get...
Lily Lane is bored to death unpacking candles day in and day out. Things at her job...
Rosy just got a really bad pedicure by a worthless foot boy. She shows you how to pamper her...
Rosy just got a really bad pedicure by a worthless foot boy. She shows you how to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
This is one FILTHY cuckolding shoot you DO NOT want to miss! Welcome Princess Penny to Divine...
This is one FILTHY cuckolding shoot you DO NOT want to miss! Welcome Princess Penny to...
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...
the InterviewShe is told to peel off that hot little dress and sniff the cuffs. A thick dildo...
the InterviewShe is told to peel off that hot little dress and sniff the cuffs. A...
Very bad student is spanked as punishment
Very bad student is spanked as punishment
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
While Bella Rossi waits for her boyfriend in a night club, she is approached by two sexually...
While Bella Rossi waits for her boyfriend in a night club, she is approached by two...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
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In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
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...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
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!...
Bare bottom otk spanking for bad lad over strict mistresss knee - flaming buttocks
Bare bottom otk spanking for bad lad over strict mistresss knee - flaming buttocks
Very bad girl gets a yardstick spanking
Very bad girl gets a yardstick spanking
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she...
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...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
The office boy gets fucked in this update. Being called out on the carpet by Harmony Rose is not...
The office boy gets fucked in this update. Being called out on the carpet by Harmony...
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Seductive brunette mistress in black boots punishing her slave for being bad boy
Seductive brunette mistress in black boots punishing her slave for being bad boy
div idmm h3Divine Bitch Mistress Lorelei Lee brSlave Drake Templeh3 pI was fed up with slaveboys...
div idmm h3Divine Bitch Mistress Lorelei Lee brSlave Drake Templeh3 pI was fed up with...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
This is one FILTHY cuckolding shoot you DO NOT want to miss! Welcome Princess Penny to Divine...
This is one FILTHY cuckolding shoot you DO NOT want to miss! Welcome Princess Penny to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Porn Star Mckenzie Lee makes her debut on WhippedAss.com in a fantasy roleplay about a nosy...
Porn Star Mckenzie Lee makes her debut on WhippedAss.com in a fantasy roleplay about a...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses...
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...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
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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...
Ashley Jane is so pretty and cute that you almost feel bad for her when shes getting punished....
Ashley Jane is so pretty and cute that you almost feel bad for her when shes getting...
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...
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...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Mistress Sandra Romains command of the male anatomy is made painfully clear as she casually...
Mistress Sandra Romains command of the male anatomy is made painfully clear as she...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
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...
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...
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...
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In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
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style typetextcssmm h3,mm h4,mm p,mm ol,mm ol li,mm ul,mm ul li font-familyVerdana,...
Femdom Cheyenne straightens out a punkass kid with a good old fashioned beating! She has the...
Femdom Cheyenne straightens out a punkass kid with a good old fashioned beating! She...
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...
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...
Femdom Annika humiliates her slave by forcing him to dress up in bad drag, complete with a wig....
Femdom Annika humiliates her slave by forcing him to dress up in bad drag, complete...
Sexy Kacie Castle loves to play the punishment game. Kacie was a Bad Girl, and Seth Gamble gives...
Sexy Kacie Castle loves to play the punishment game. Kacie was a Bad Girl, and Seth...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
Ashley Jane is so pretty and cute that you almost feel bad for her when shes getting punished....
Ashley Jane is so pretty and cute that you almost feel bad for her when shes getting...
Ready for your buttons to be pushed again? Do you sincerely have true and utter devotion for the...
Ready for your buttons to be pushed again? Do you sincerely have true and utter...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
Mistress Lotus Lain returns home to find her bitch boy Jonah Marx bound and waiting to serve...
Mistress Lotus Lain returns home to find her bitch boy Jonah Marx bound and waiting to...
Heavily tattooed vegan straightedge punk, Rukus, is caged and left as a surprise in Maitresse...
Heavily tattooed vegan straightedge punk, Rukus, is caged and left as a surprise in...
Garrett Nova is a 19 year old student whos parents pay his way through college. Problem is...
Garrett Nova is a 19 year old student whos parents pay his way through college....
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The stunning Ana Foxxx is at a high fashion photo shoot with the nervous and sweaty Will Havoc....
The stunning Ana Foxxx is at a high fashion photo shoot with the nervous and sweaty...
The office boy gets fucked in this update. Being called out on the carpet by Harmony Rose is not...
The office boy gets fucked in this update. Being called out on the carpet by Harmony...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we...
The stunning Ana Foxxx is at a high fashion photo shoot with the nervous and sweaty Will Havoc....
The stunning Ana Foxxx is at a high fashion photo shoot with the nervous and sweaty...
While Bella Rossi waits for her boyfriend in a night club, she is approached by two sexually...
While Bella Rossi waits for her boyfriend in a night club, she is approached by two...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who...
Porn Star Mckenzie Lee makes her debut on WhippedAss.com in a fantasy roleplay about a nosy...
Porn Star Mckenzie Lee makes her debut on WhippedAss.com in a fantasy roleplay about a...
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...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy yet bad...
Homecoming queens Annika Albright and Ash Hollywood are the princesses of the academy...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses...
In this roleplay update sexy redhead Elle Alexander plays a rookie cop who busts known sexy MILF...
In this roleplay update sexy redhead Elle Alexander plays a rookie cop who busts known...

More Spanking Galleries

Mistress Sandra Romains command of the male anatomy is made painfully clear as she casually...
19 year old piano student, Tiger Wilde, gets more than she bargained for when she finds out her...
Ashley Jane is so pretty and cute that you almost feel bad for her when shes getting punished....
Top notch talent agent Chanel Preston is fed up with entitled actress Zoey Monroe making her...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
Music nerds know this never, ever try to impress the girl behind the counter Especially when she...
Officer Moreau has been lusting after one of his inmates - the gorgeous, busty Lana Knight - for...
Music nerds know this never, ever try to impress the girl behind the counter Especially when she...
Music nerds know this never, ever try to impress the girl behind the counter Especially when she...
Officer Moreau has been lusting after one of his inmates - the gorgeous, busty Lana Knight - for...
Corruption in the sinful city of San Francisco has never looked so sexy. The bad boys of law...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
In this prison roleplay newcomer Vicki Chase and Penny Barber play two hookers who land...
Missy Minx, Felony and Maitresse Madeline have explosive chemistry in this kinky tale about a...
Trust fund brat, Penny Pax is a control freak. Day after day she tortures her maids by making...
Simone Sonay has arrived to Divine Bitches and she is fierce!!!! Bow down to Mrs. S, boys and be...
If Bobbi Starr wants tits, Bobbi Starr will get tits. Bobbi hires a big titted stripper for her...
Trust fund brat, Penny Pax is a control freak. Day after day she tortures her maids by making...
Bad girl is spanked for losing her bfs report
Dominatrix legends Maitresse Madeline and Aiden Starr unleash their cruelest impulses to haze...
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...
Missy Minx, Felony and Maitresse Madeline have explosive chemistry in this kinky tale about a...
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 making...
Trust fund brat, Penny Pax is a control freak. Day after day she tortures her maids by making...
Mistress Nyxon gets creative with a classic hand drill that involved nipple clamps and one very...
Gwen Diamond and Little Billys first MIP pairing revealed such a hot chemistry that we had to...
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