Anal Pain Movies

Raisa did not care about the pain that came with having anal sex for the first time. She wanted...
Raisa did not care about the pain that came with having anal sex for the first time....
Krissy Leighs overnight stay at the hospital is full of sexual domination and lesbian sex. Nurse...
Krissy Leighs overnight stay at the hospital is full of sexual domination and lesbian...
2 amazing babe starring riley evans discipline their 2 employees by having them fuck them in the...
2 amazing babe starring riley evans discipline their 2 employees by having them fuck...
Funny, Mz Berlin never actually shot for Men In Pain back in the day yet she remains a legend to...
Funny, Mz Berlin never actually shot for Men In Pain back in the day yet she remains a...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
Episode 4 Audrey has already proven herself to be an anal whore and a pain slut. Who can resist...
Episode 4 Audrey has already proven herself to be an anal whore and a pain slut. Who...
This was a rough anal sex tryout where we witnessed a lot of pain but also a lot of pleasure....
This was a rough anal sex tryout where we witnessed a lot of pain but also a lot of...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
4 Movies of swinging BI teens and an ANAL Cream Pie
4 Movies of swinging BI teens and an ANAL Cream Pie
Episode 4 Audrey has already proven herself to be an anal whore and a pain slut. Who can resist...
Episode 4 Audrey has already proven herself to be an anal whore and a pain slut. Who...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Kayden was excited about being dominated by Isis Love in sexy latex. Kayden specially requested...
Kayden was excited about being dominated by Isis Love in sexy latex. Kayden specially...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and Aiden Starr...
Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and...
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Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and Aiden Starr...
Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and...
To get in the Halloween spirit I wanted to do something extra special for the members of Whipped...
To get in the Halloween spirit I wanted to do something extra special for the members...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi Starr. She...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Goddess Starli has an anal virgin to play with. She starts small and works her way up to shoving...
Goddess Starli has an anal virgin to play with. She starts small and works her way up...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore...
When a beautiful slave girl, Nora Riley, falls in love with her Master, Derrick Pierce, she...
When a beautiful slave girl, Nora Riley, falls in love with her Master, Derrick...
Veruca James and Charlotte Sartre are butt sucking vampires invited in by the secret wishes of...
Veruca James and Charlotte Sartre are butt sucking vampires invited in by the secret...
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In this scene we will see this cute anal virgin named Ashley get down on all fours and take a...
In this scene we will see this cute anal virgin named Ashley get down on all fours and...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales walking...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi Starr. She...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi...
Sea J Raw is quit the pain slut. She seems to get turned on from being punished and obedient to...
Sea J Raw is quit the pain slut. She seems to get turned on from being punished and...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging,...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
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Young Mary felt pain and pleasure as she had her first anal. But as the pleasure increased, she...
Young Mary felt pain and pleasure as she had her first anal. But as the pleasure...
Two Girls eagerly await Ariel X. They get in position to be spanked, Gaped and Fisted. Alexa...
Two Girls eagerly await Ariel X. They get in position to be spanked, Gaped and Fisted....
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi Starr. She...
Amber Keen is a beautiful BDSM lifestyler who gets tied up and dominated by Bobbi...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and submission but...
Welcome newcomer Bailey Blue to Whipped Ass. Bailey is new to punishment and...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging,...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to be kinky,...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to...
To get in the Halloween spirit I wanted to do something extra special for the members of Whipped...
To get in the Halloween spirit I wanted to do something extra special for the members...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales walking...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales...
Dr. Torns FemDomme Laboratory Pushed, Probed, Fucked and Cucked!Dr. Cherry Torn conducts medical...
Dr. Torns FemDomme Laboratory Pushed, Probed, Fucked and Cucked!Dr. Cherry Torn...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
This girl promised her boyfriend anal sex. Since they had not had it before, he was excited and...
This girl promised her boyfriend anal sex. Since they had not had it before, he was...
Nicki Blue and Dana Vixen get intense domination and anal abuse from Isis Love and Mark Davis!...
Nicki Blue and Dana Vixen get intense domination and anal abuse from Isis Love and...
As his cock entered young Harpers ass, she felt a mixture of pain and pleasure. But she...
As his cock entered young Harpers ass, she felt a mixture of pain and pleasure. But...
Chastity Lynn and Alice Frost get an intense lesson from Chanel Preston about the pain and...
Chastity Lynn and Alice Frost get an intense lesson from Chanel Preston about the pain...
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Veruca James and Charlotte Sartre are butt sucking vampires invited in by the secret wishes of...
Veruca James and Charlotte Sartre are butt sucking vampires invited in by the secret...
When Lady Roxanne Rae catches her wealthy husband Derrick Pierce getting his dick sucked by the...
When Lady Roxanne Rae catches her wealthy husband Derrick Pierce getting his dick...
We love Darling not only for her amazing talent of flexibility but also how this hot cunt can...
We love Darling not only for her amazing talent of flexibility but also how this hot...
Chastity Lynn and Alice Frost get an intense lesson from Chanel Preston about the pain and...
Chastity Lynn and Alice Frost get an intense lesson from Chanel Preston about the pain...
Skin Diamond is a blend of unique beauty and maso-slut. Today, we challenge her with endurance...
Skin Diamond is a blend of unique beauty and maso-slut. Today, we challenge her with...
Super juicy hot ass booty shorts babe gets her amazing ass fucked and cumfaced in these 2 cocks...
Super juicy hot ass booty shorts babe gets her amazing ass fucked and cumfaced in...
As the cock got inside young Tatjana, she screamed in a mixture of pain and pleasure. But she...
As the cock got inside young Tatjana, she screamed in a mixture of pain and pleasure....
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first...
Two Girls eagerly await Ariel X. They get in position to be spanked, Gaped and Fisted. Alexa...
Two Girls eagerly await Ariel X. They get in position to be spanked, Gaped and Fisted....
This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot movies....
This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot...
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I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to be kinky,...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to be kinky,...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to...
Welcome back the tough and beautiful Elisa Graves to WhippedAss.com! Lorelei Lee and Aiden Starr...
Welcome back the tough and beautiful Elisa Graves to WhippedAss.com! Lorelei Lee and...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to be kinky,...
I did my research on Melina Mason. She comes from Jersey, thinks shes kinky, wants to...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales walking...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging,...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales walking...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales walking...
Drinking coffee on a sunny after noon, Rose Rhapsody spots hot dominatrix Mona Wales...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging,...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor...

More Anal Galleries

Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
This fantasy roleplay shoot is an ode to sexploitation, women in prison, revenge plot movies....
To get in the Halloween spirit I wanted to do something extra special for the members of Whipped...
Chloe Camilla gets fucked on camera for the first time! This sexy little nympho takes some...
Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and Aiden Starr...
Cruel and sexy dominatrix Cherry Torn allows hot pain slut Violet Monroe to pick her implements...
Submissive babe Savannah Fox crawls into Mistress Chanel Prestons dungeon eager to serve. The...
Hot anal sex movies from the sixties
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
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Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
Nicki Blue and Dana Vixen get intense domination and anal abuse from Isis Love and Mark Davis!...
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Dr. Torns FemDomme Laboratory Pushed, Probed, Fucked and Cucked!Dr. Cherry Torn conducts medical...
Sensual latex domme, Bella Rossi uses all her electro toys to make horny busty blonde, Angel...
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Welcome Tia Ling back to Whipped Ass in one of her hottest movies yet! In the first scene Tia is...
Blonde beauty bent over in pain - deep anal fingering and hard bare bottom spanking
Welcome back the tough and beautiful Elise Graves to WhippedAss.com! Lorelei Lee and Aiden Starr...
Welcome Odlie to Whipped Ass. A lifestyle submissive with a hunger for pain and domination. In...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Pink the pain slut visits brutal dominatrix Felony for a session filled with flogging, spanking,...
Holly Hendrix is a sex-hungry pain slut being kept for observation by devious doctor Cherry...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
Welcome 20 year old Mandy Muse to Whipped Ass! Shes young, sweet and eager to explore all her...
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