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Total SCENES 234 PAGES « 1 2 [3] 4 5 6 . . . 44 45 46 47 » SORT VIDEOS BY:   DATE |  NAME

ALL NEW FEATURE PRESENTATION Join This Site & Get Access To 40+ HD Helplessteens.com Videos Callie Calypso Endures Domination, Outdoor Rough Sex & Rope Bondage for a Ride Description: Poor Callie Calypso. She took her mom's car without permission and got into an accident. Now she's stranded in the middle of nowhere. This helpless teen can't hold back her tears. She's in big trouble! Luckily, a white van pulls up. She talks to the driver and begs for a ride. She'll do anything to get home and fix the car. Her hero seems like a great guy but wants to be satisfied first before bringing her home. He surprises her with plastic wrap around her face and ties her wrists together with rope. He throws her in the back of the van for more fun. Callie resists at first with a spicy attitude but eventually submits to her new Master's love of rope bondage, domination, BDSM, rough sex and deepthroat blowjobs, all outdoors. He even has a dungeon with sex toys for a slave training session. Callie becomes an obedient slut and begs for cum. CLICK HERE TO WATCH MORE VIDEOS

Lara's Return Apparently some women have trouble recognizing the wrong they had done. Lara was one of these people,who despite everything that is done to them, the just refuse to learn their lesson, Perhaps it’s defiance, or perhaps deep down inside she enjoys the burning sensation felt on her bottom. The marks from before were still visible, making new blows all the more painful. We doubt she'll stop, but we'll make sure to continue punishing her.  Updated April 4, 2024

Blonde in orange Adriana had been working outside, as part of her punishment for stealing from her room mate. She however felt that she was above manual labor, since she had come from a rich. The headmistress wasn't a particular fan of this thought process. She then brought her into our punishment chamber, and had her tied up from above. Her back is completely exposed to the savage flogging. The red marks color is once milky colored skin, marking her as one of the punished.  Updated March 21, 2024

Spanking Orgasm Sylvia is one of those repeat offenders, always coming back to the headmasters punishment room, always in some form of trouble. It is made apparent that the harder Sylvia was spanked, the more and more she screams. Whether they are screams of pain of pleasure, the headmasters aren't sure. Nonetheless they punish the little slut, thinking that someday she will learn.  Updated February 21, 2024

ALL NEW FEATURE PRESENTATION Join This Site & Get Access To 40+ HD Helplessteens.com Videos Lizzie Bell is Lost & Must Endure Outdoor Rough Sex, Rope Bondage & Deepthroat BJ for a Ride Description: Description: Helpless teen Lizzie Bell went out for a simple walk. She took a wrong turn and is now lost. She doesn't know how to get back home. She's getting scared, hoping she'll find her way back before it gets dark. She's been walking for hours. Fortunately, a white van approaches and the driver stops to see if she needs help. She begs him for a ride, telling him she'll do anything. He agrees to help and she gets in. They talk for awhile, but he eventually gets right down to business. If she wants a ride, she better be willing to have some fun. She's a bit nervous but wants to get home. She's thinking a deepthroat BJ will be enough but learns that's it won't when her wrists are tied to together. He pulls her to the back of the van where she must endure rope bondage, more domination, BDSM, rough sex, all outdoors. He even has a dungeon with sex toys for a slave training session. He wants to Lizzie squirt over and over. CLICK HERE TO WATCH MORE VIDEOS

School Of Pain Lara is in todays caning video, with the headmasters leading the punishment. She was found smoking in the girls bathroom, and her streak of rebellion had to end. They then knew corporal punishment was the only way to teach a slut of this magnitude, and thus they commenced the canning. During the process, they managed to break the skin a few times, ensuring that she would indeed learn her lesson, at the very lest for sometime. We knew she would be back.  Updated January 31, 2024

Will Nikki learn? Nikki is at it again, this time with a problem in gym leading to her latest punishment. The headmaster picked up a wooden staff, knowing the full effect it would have on her. He repeatedly struck her until bruises began to appear, reminders for the rest of the week.  Updated January 10, 2024

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Total SCENES 234 PAGES « 1 2 [3] 4 5 6 . . . 44 45 46 47 » SORT VIDEOS BY:   DATE |  NAME

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