August 23 - Babysitter Angel Chairtied Barefoot and Tapegagged, You Daydream She's Topless!
60 NEW High-Res Photos (2,200 Pixels High)

2 Damsels! 2 Updates This Week! Up first in this week's update we have 60 gorgeous babysitter bondage photos! You super-cute sitter is Angel and today she agreed to play a tie-up game! Now she's all tied-up to a chair, barefoot in a denim miniskirt and sweater. She even let you tapegag her! Angel poses like a real damsel in distress and she's simply amazing at it! You watch in sheer delight as she wiggles and struggles playfully.

You're so mesmerized that you drift off into a daydream where Angel's top fall down! You can't believe her gorgeous boobies! You wish you could stay in your fantasy forever...

"Hey, is this game over yet?" you hear your sitter ask, muffled by all that tape across her lips.

Is the game over? You don't want it to ever end, but better untie her so she lets you play more games another day!

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

August 23, 2025 - (1080p - 9:30 min.) REAL-LIFE Babysitter Bondage! Barefoot Natasha Flade Plays Ransom, Gets Caught Hopping Away, Gets Hogtied! Classic Bondage from 2010 – Now In 1080p for Highest Quality!

2 Damsels! 2 Updates This Week! Up next, we have a real-life babysitter bondage game that Natasha Flade played for Isaac W. on his birthday. In the game, Natasha Flade is watching two boys and they want to tie her up AGAIN! She’s on the couch in her pink robe and barefoot when her charges approach and invite her to play a game called ransom.

Natasha smiles and laughs. She knows how you boys (and Isaac!) love their tie-up games. But she likes playing along, so she agrees and throws her hands up at your toy gun. She crosses her hands behind her back to be tied up. Soon your sitter is bound hand and foot on that sofa. But you want to see your pretty nanny gagged, too! So you ask really nicely if that’s okay. Natasha agrees and allows a large, balled-up cloth as a stuffer gag. Your babysitter plays the part of a real damsel, playfully struggling for your entertainment. And she keeps rattling on in gag talk from behind that huge wad in your mouth. Wow! You’re such a lucky boy!

Then Natasha decides to hop away all the way into the kitchen to get a knife and cut herself loose! It’s a great scene with your babysitter hopping while she’s tied up and gagged, and looking around to make sure you don’t see her trying to escape. But she gets caught by you boys! You decide your naughty nanny needs to be hogtied so she can’t get away. And now she's cleave-gagged with a kitchen towel, too!

Natasha spends the remainder of the video hogtied barefoot on the kitchen floor, rolling around, her bare feet and soles wriggling, her damsel eyes wide and pleading, and gag-talking a LOT! She's getting a bit mad as she asks if the ransom has been paid yet so you can let her go. Nah, what fun would that be?!

Some cute outtakes at the end!

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

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!

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