Painful Anal Sex Stories

This girl has always wanted to try anal sex but was too scared. She thought it was going to be...
This girl has always wanted to try anal sex but was too scared. She thought it was...
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...
All girls crave for anal sex, you can take that for the bank. Even when they tell you they think...
All girls crave for anal sex, you can take that for the bank. Even when they tell you...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In...
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...
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...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
Watch Harpers first ever anal sex tryout. Her tight asshole actually responded quite well to the...
Watch Harpers first ever anal sex tryout. Her tight asshole actually responded quite...
To show what shes made of, young Raisa chose to ride a huge cock on her first time having anal...
To show what shes made of, young Raisa chose to ride a huge cock on her first time...
When the guy inserted his cock inside Vladas young ass, she felt like screaming. It started out...
When the guy inserted his cock inside Vladas young ass, she felt like screaming. It...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
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...
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 the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
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Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
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Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
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...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back....
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back....
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back....
Slave trainee Veruca James learns to manage all the fuck holes at the hands of Slave Trainer...
Slave trainee Veruca James learns to manage all the fuck holes at the hands of Slave...
Dahlia Sky is a fucking dream wife submissive, gorgeous, and a voracious anal slut. Plucked...
Dahlia Sky is a fucking dream wife submissive, gorgeous, and a voracious anal slut....
Dahlia Sky is a fucking dream wife submissive, gorgeous, and a voracious anal slut. Plucked...
Dahlia Sky is a fucking dream wife submissive, gorgeous, and a voracious anal slut....
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your heart, swell...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your heart, swell...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your...
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Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your heart, swell...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your heart, swell...
Irresistible Zoey Monroe is a gorgeous little blonde bombshell that will melt your...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back....
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back....
Elise Graves and Amber Rayne take on a feast of anal punishment and pleasures as they fuck,...
Elise Graves and Amber Rayne take on a feast of anal punishment and pleasures as they...
Two cuties take some painful anal sex
Two cuties take some painful anal sex
They met at the club. After a few drinks and dances, they ended back at his apartment and had...
They met at the club. After a few drinks and dances, they ended back at his apartment...
Jack fights with his wife and storms off to a strip club to dare himself to do what he has...
Jack fights with his wife and storms off to a strip club to dare himself to do what he...
Jack fights with his wife and storms off to a strip club to dare himself to do what he has...
Jack fights with his wife and storms off to a strip club to dare himself to do what he...
Jack fights with his wife and storms off to a strip club to dare himself to do what he has...
Jack fights with his wife and storms off to a strip club to dare himself to do what he...
Jack fights with his wife and storms off to a strip club to dare himself to do what he has...
Jack fights with his wife and storms off to a strip club to dare himself to do what he...
Its always fun watching girls get fucked in the ass for the first time, especially when they are...
Its always fun watching girls get fucked in the ass for the first time, especially...
Slim and smooth hardcore blonde in lustfully mad anal sex erotica
Slim and smooth hardcore blonde in lustfully mad anal sex erotica
Arianna is an anal sex virgin who wants to see how all the fuss is about. She was scared about...
Arianna is an anal sex virgin who wants to see how all the fuss is about. She was...
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Sweet nympho Victoria had her tight ass stretched for cash during her first anal sex experience
Sweet nympho Victoria had her tight ass stretched for cash during her first anal sex...
Some girls simply cannot live without anal sex. Once they try it they are completely hooked for...
Some girls simply cannot live without anal sex. Once they try it they are completely...
Cute inexperienced in anal sex slutty girl with an extra narrow virgin asshole fucked tenderly
Cute inexperienced in anal sex slutty girl with an extra narrow virgin asshole fucked...
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...
This teen is full of lust and desire she is always ready for the filthiest experiments with her...
This teen is full of lust and desire she is always ready for the filthiest experiments...
Samantha had finally arrived at the time in her life when she wanted to try anal sex. She is...
Samantha had finally arrived at the time in her life when she wanted to try anal sex....
Carter Cruise and Dakota Skye star in this epic feature presentation with James Deen. Two girls...
Carter Cruise and Dakota Skye star in this epic feature presentation with James Deen....
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In...
Nataly is trying anal sex for the first time and letting us film all the action. Get comfortable...
Nataly is trying anal sex for the first time and letting us film all the action. Get...
When are two strangers the same person?When the seemingly prudish wife of a lottery winner is...
When are two strangers the same person?When the seemingly prudish wife of a lottery...
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...
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Unsatisfied with her current sex life, Calico dreams up a dark fantasy where she gives up all...
Unsatisfied with her current sex life, Calico dreams up a dark fantasy where she gives up all...
Unsatisfied with her current sex life, Calico dreams up a dark fantasy where she gives up all...
Unsatisfied with her current sex life, Calico dreams up a dark fantasy where she gives up all...
To get in the Halloween spirit I wanted to do something extra special for the members of Whipped...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
CiCi Rhodes has a close relationship with Mark Davis off camera. On camera, they show us how...
To get in the Halloween spirit I wanted to do something extra special for the members of Whipped...
Kimber Woods is clearly smitten with her coworker Penny and jumps at the chance to have a drink...
Kimber Woods is clearly smitten with her coworker Penny and jumps at the chance to have a drink...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new but she arrives with a...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new but she arrives with a...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Welcome the adorable Adrianna Luna to WhippedAss.com! Adrianna may be new, but she arrives with...
Gabriella gets her tight ass fucked by her boyfriend who caught the whole thing on video tape,...
Ass pounding and pussy drilling were followed with moaning. Ira has never had anal sex before...
This is the first time Dana ever gets her ass fucked and she already wanted to sit right on top...
Elise Graves and Amber Rayne take on a feast of anal punishment and pleasures as they fuck,...
Mellanie Monroe gets turned on by kinky bondage sex and takes hard punishment from Nika Noire....
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The beautiful and very submissive Cherry Torn returns with new guy Xander Corvus! In this...
The insatiable wonder that is our sex slave Veronica Avluv takes on her greatest apprentice yet...
The insatiable wonder that is our sex slave Veronica Avluv takes on her greatest apprentice yet...
Slave trainee Veruca James learns to manage all the fuck holes at the hands of Slave Trainer...
Slave trainee Veruca James learns to manage all the fuck holes at the hands of Slave Trainer...
Slave trainee Veruca James learns to manage all the fuck holes at the hands of Slave Trainer...
Gorgeous little Holly Hendrix is an out of control 18 year old that needs some discipline in her...
Gorgeous little Holly Hendrix is an out of control 18 year old that needs some discipline in her...
Gorgeous little Holly Hendrix is an out of control 18 year old that needs some discipline in her...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Simone is both sly and slutty. When she catches a look at the elegant new maid, she hatches a...
Gorgeous little Holly Hendrix is an out of control 18 year old that needs some discipline in her...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
Daisy Ducati and Savanna Fox have met in Champion vs Champion match a few years back. See that...
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