August 13, 2025 - (720p - 3:30 min.) Naughty Babysitter Chastity Rhoades Punished by Mom for Letting Her Son Tie Her Up! Classic Bondage from 2006 - Now in 720p for Highest Quality!

2 Damsels! 2 Updates This Week! Up next this week we have a newly re-edited video in 720p! Your babysitter today is busty Chastity Rhoades! You asked her to play a tie-up game with you and she agreed. Yay! Now she's tied-up and gagged, bound seated on the kiva fireplace in her denim miniskirt, tights and boots.

You watch with delight as she wiggles around and mmphs from behind her knotted cleave-gag. Her cleavage is pouring out of her top. You wonder if maybe her boobs will pop right out! It's your lucky day!

But not so much for poor Chastity because just then your mom Natasha Flade comes home. Worried what she'll say, you run off and hide. Not knowing what to do, Chastity stands and tries to hop away, but your mom catches her!

She's none too pleased to find the babysitter all tied-up by her son! She drags Chastity back to the fireplace and decides to punish her by pulling down her top. There! If the naughty babysitter wants to play tie-up, she can sit here bound and gagged a while longer!

Mom makes sure you're in your room and the helpless Chastity is left alone to struggle, now tied up topless, and wondering what the heck sort of mess she's gotten herself into!

2 UPDATES! 2 DAMSELS! What a day to become a member of Babysitter Bondage!

August 13 - Mom Natasha Flade, Barefoot in Shorts, Tied Standing to Bed Post and Cleave-Gagged! 48 New High-Res PHOTOS! (2,200 Pixels Hight)

2 Damsels! 2 Updates This Week! Up first in this week's update we have 48 new MILF bondage photos! Your mom, Natasha Flade, is sitting on the bed, barefoot in shorts, when you approach and ask to play a game of "ransom." Your mom loves to indulge you, so she agrees to play and throws her hands up into the air. "Oh no!" she says, pretending to be scared. But she's smiling a lot, too, because she thinks these tie-up games of yours are really fun!

You have her stand up against the bed post, then her hands are bound behind it. Her ankles are roped together next, then ropes are tied about her thighs and chest. Her boobies really poke out like that! Mom poses for you as she plays her damsel part. It's amazing!

But you say she needs to be gagged, too, so she doesn't call for help. Mom goes along with that as well and winds up cleave-gagged with a robe sash. She makes the best damsel expressions as she continues to pose for you, sometimes concerned, sometimes smiling. She's the best mom in the world!

2 UPDATES! PHOTOS + VIDEO! What a day to become a member of Babysitter Bondage!

August 7, 2025 -- (720p - 8:30 min.) Nanny Natasha Flade & Office Mom Kylie Samone Bound Back-to-Back for Mad Scientist Game, then Dad Comes Home for Fun! Classic Bondage from 2002 - Now in 720p for Highest Quality!

2 Updates This Week! Up next this week we have a newly re-edited video in 720p! Kelly (Natsha Flade) is little Joey's nanny. It’s Kelly's job to entertain her charge, but she’s finding out that Joey just likes to play different versions of the same game where his babysitter always gets tied up and gagged! And Kelly loves to indulge him! But this time, Joey's mom Laura (Kylie Samone) returns home from her job at the office to find the nanny all tied-up and stuffer gagged on the floor!

Kelly is worried she might be in trouble! But Joey's mom thinks it's funny and asks her son what's going on. Joey doesn’t miss a beat. It's an opportunity to tie up mom, too! Keeping up his mad scientist shtick, he says to his mom, “Now I have to tie you up, too!"

"Oh, you will, will you?” Laura says with a smile. She laughs and holds out her hands to be tied up, going along with her son's game. The scene cuts to mom and babysitter tied up together, bound back-to-back, hands tied in front and roped tightly to their thighs. Looks like even mom allowed a stuffer-gag, too! Both ladies struggle like real damsels-in-distress for Joey’s entertainment, and they look so damn good doing it, too! We get great shots of Natasha's bare feet contrasted with Kylie's high heels and office attire.

After a while, Kylie’s husband (Isaac W.) returns home to find the two lovelies tied up and gagged on the floor. Natasha is worried what he might think, but he just laughs. Then he ungags his wife to get the story. Laughing, she tells him they were playing Joey's mad scientist game just for fun. Then her husband re-gags her just for his fun! He tells them his son did a good job, but looks like they need another two hours like this. Kelly and Natasha try to protest as Isaac strolls off, leaving mom and babysitter to struggle some more, but now just a little bit angry!

Some cute outtakes included at the end!

Kylie Samone is wearing office attire: pantyhose, Mary Jane heels, and a business suit. Natasha Flade is barefoot in a miniskirt sleeveless turtleneck sweater in this MILF bondage and babysitter bondage video all in one!

2 UPDATES! PHOTOS AND VIDEO! What a day to become a member of Babysitter Bondage!

August 7 - REAL-LIFE Babysitter Bondage Game! Natasha Flade Tied-Up Barefoot in Jeans & Cleave-Gagged!
59 New High-Res PHOTOS! (2,200 Pixels to a Side)

2 Updates This Week! Up first in this week's update we have a photoset from a real-life babysitter bondage game.

“Escape, huh? Let me guess how this goes. You guys get me all tied up and I have to get loose, right?” That’s how this photoset begins with nanny Natasha Flade playing along with a real-life game for Isaac W.'s birthday. Natasha is standing, barefoot in jeans and a tank top (with plenty of nips!). She tells you to get your ropes and poses playfully as you proceed to wrap several miles of rope tied sloppily about her everywhere! She dances and poset. She’s having lots of fun!

Then you approach her with a scarf. Nanny Natasha tells you that a gag has nothing to do with this game. But you boys insist, saying that she shouldn’t be able to bite at the ropes like that. Smiling, Natasha relents and agrees to be gagged. Now she's cleave-gagged and mmphing for the boys’ benefit. She wriggles in the ropes and tries to hop away. But she’s captured!

And now your nanny is bound seated on the floor with her lovely bare soles pointed straight out! Closeups of her cleave-gagged face and perfect soles are plenty! At the end, she gag-talks that she lost the game, she couldn’t get loose!

2 UPDATES! PHOTOS & VIDEEO! What a day to buy a pass and become a lucky Babysitter Bondage member!

July 29, 2025 - Natasha Flade Tied-Up by Chloe's Son While Babysitting After Work, Chloe Comes Home to Get Her Topless & Play With Her! 61 NEW Photos + 1,200 Word STORY!

TWO UPDATES THIS WEEK! I was at the office when Chloe called me. It was a call, not a text, so I knew it was important, so I picked up. “Sorry to hit you up at work, but I really need a favor. I have to step out and I can’t take Jackson with me. Is it possible you can watch him until I get back? I’ll be gone an hour or two. No more. Promise.” [...] She paused. “One more thing. Jackson has been really into tie-up games lately. He had me all tied up to the chair in the den the other day. Just so you know, he might try to get you to play.”

I laughed, picturing Chloe all tied up at Jackson’s hands, maybe with a gag in her mouth but I didn’t ask for details. "That’s fine. Jackson can capture me if he wants. He’s a sweetie.” [...]

“You may come home to find me bound and gagged.” Now Chloe laughed. “I promise to rescue you.” [...] I went upstairs to find Jackson. [...] So, do you want to play a game or something until Mom gets back? How about your favorite board game?” Jackson shook his head. “I don’t think so.”

“So, what, then?” He scratched his curly brown hair, pretending to think on the issue. “How about ransom?”

“Ransom? How do you play that?” I decided to play dumb.

“Well, I play like I’m a kidnapper, and I tie you up and hold you for ransom.”

“Tie me up? What would your mother think, coming home to find me all tied up?”

“She plays this game with me. She would think it was funny.” I chuckled. She would, indeed. “Okay. I’ll play and you can tie me up. How do we start?” [...]

# # #

Chloe appeared at the top of the stairs and laughed, seeing me in my predicament. “Glad to see you two having fun.” She turned to Jackson. “Did you clean your room? You were supposed to have that done. Well, get downstairs and get to it. I don’t want to see you back up here until your room is spic and span.”

He sighed. “All right.” He got up and headed downstairs, but not before turning around one more time to take a good gander at me sitting there tied up and gagged. Chloe giggled again. “Thanks for being a sport and playing his game.”

I nodded, “Mmm-hmmm.” She kneeled in front of me. “You do look hot all tied up.” I rolled my eyes. Chloe began unbuttoning my top. What was she doing? “Hey,” I said through my gag. She placed a hand over my lips. “Shhh. We don’t want Jackson up here. I need to see your titties.” Chloe went back to the buttons. [...]

The entire story and all 61 high-res photos are in the member area!

PHOTOS AND VIDEO! What a day to buy a pass and become a lucky Babysitter Bondage member!

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