September 9 - Mom Natasha Flade Post-Tied Outside! 27 BRAND NEW High-Res Photos (2,200 Pixels High)

You and your brother have convinced your redhead mom, Natasha Flade, to let you tie her up outside in the woods! You have her tied up against a really big post, in her jeans, sneakers and tank top. You tied her really well, too! Her wrists are bound together behind the post and the chest ropes have been wrapped around it, too. Mom Natasha teases you guys about your tie-up games and says you only get to play this bondage game for a half hour today. After all, she let you tie her to a chair just earlier this week!

But Natasha is actually having lots of fun playing your game today. She even agreed to be cleave-gagged, too. Yay! So here’s your hot mom, bound and gagged in the woods in the middle of nowhere! She plays along, acting out the part of a real damsel in distress. Looking around fretfully, she says throug her gag, "What am I going to do?! These bad guys just left me here!”

Natasha playfully struggles, but after a while, she starts calling for you boys to come back — your time is up! But you take your sweet ole time getting there, much to mom’s dismay. So she promises she’ll let you boys tie her up again tomorrow, this time to a chair, if you just please come back and untie her from the tree. That’s good enough incentive for you! It will be hard to sleep tonight, waiting for more tie-up games tomorrow with mom!

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

(720p - 15:30 min.) Ebony Babysitter Jasmine Taliana Tied-Up for Game, then Molested, Spanked & Tickled by Your Mom & Her Hot Blonde Friend! Classic Bondage from 2008 – Now In 720p for Highest Quality!

Ebony babysitter Jasmine Taliana let herself get into a real bind! She’s watching TV on the sofa when her charge comes in and asks if she would like to play a game. Jasmine agrees. She’s approached with a toy gun and ordered to pout her hands up. Babysitter Jasmine holds her hands up and plays along. She winds up tied up on the sofa with jump ropes, hands in front. When she playfully calls for help, she’s OTM gagged! She struggles like that for a bit as we get peeks of her cute soles and closeups of her OTM gagged face.

The kid’s mom, Natasha Flade, and her hot blonde friend, Kordelia Devonshire, return home to find the sitter bound barefoot and gagged in her denim miniskirt and sweater! They laugh at at her situation, then the two ladies decide to have some fun and teach the naughty nanny a lesson! They whip out some real rope and tie Jasmine’s hands behind her back. They even give her elbow ties!

Jasmine isn’t quite sure what to make of all of this. She’s nervous because she doesn’t want to lose her babysitting job, but she’s also worried since Natasha and Kordelia are acting sort of crazy in her opinion. Not that she can voice her protests since they stuffed her mouth with a big cloth with a scarf wrapped on top. With poor Jasmine now effectively silecned, they can really get down to business!

Poor Jasmine is stripped topless, then her miniskirt and panties pulled down! She’s mostly naked now and completely at their mercy. Kordelia and Natasha take turns tormenting Jasmine by tickling her bare feet, with great close-ups of Jasmine’s soles being tickled relentlessly! Kordelia even bites her toes! Then they spank her bare ass and grope her tits, laughing as she squirms about. Jasmine tries to plead for them to please stop, but it all comes out in muffled gag talk. This ebony babysitter should learn her lesson by the time Kordelia and Natasha are done with her!

Lots of cute outtakes at the end!

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

TWO UPDATES THIS WEEK! - Neighborhood Girls Angel Lee & Danielle Trixie Tied-Up Together On Sofa! 34 NEW High-Res Photos (2,200 Pixels Wide)

In the first set, you convinced the neighborhood girls Angel and Danielle Trixie to let you tie them up! They're bound together on the sofa in their little skirts/dress and summer heels. They're attached to each other at their arms and they're cleave-gagged, too. Damn, they're hot!

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

Cousin Angel Lee Plays Tie-Up Outdoors in Dress! 80 NEW High-Res Photos (2,200 Pixels Wide) PLUS 1,100 Word STORY!

I’d been excited all week that my parents were going away for a little vacation without me. They were going to some resort that didn’t have anything fun for kids, so I didn’t want to go with them. I knew they would leave me with a sitter, which would be fine. Every sitter so far allowed me to play videogames all I wanted, which was cool. But then they told me my older cousin Angel would be with me the whole weekend! She’s really hot. Hot enough to make me nervous when she was around. I loved looking at her. So then I was seriously looking forward to my folks packing their bags!

# # #

After we got home from the zoo, I was super excited, but kept it to myself. I didn’t want to act all hyper over getting to tie her up. I made it this far being the perfect kid, I didn’t want to blow it. We ate the hotdogs she made, me squirming in the chair as I thought about Angel with a gag in her mouth. That hotdog disappeared in a minute.

When Angel was done and put our plates in the dishwasher, she said, “Ready to tie me up?”

I raced upstairs for my ropes. And mask and toy gun. I came back down with the ski mask on, the gun in hand, and ropes in my backpack. She acted scared seeing me. “How did you get in my house? What do you want?”

“Just be quiet. I’m here to kidnap you for ransom. Now put your hands behind you.”

She crossed her hands behind and I tied them. I pulled a longer rope from the pack and went to work on her elbows. No reason to be easy on her. She knew what was up. “Wow, Mr. Kidnapper. That’s awfully tight.”

“I don’t want you escaping.” I put my backpack back on and marched her to the back door.

“You’re taking me outside?” We lived on a few acers of woods. “No one will see. I have to take you to my hideout.”

All the photos plus the entire story is yours today if you buy a pass to Babysitter Bondage!

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 new 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!

(1080p - 9:30 min.) REAL-LIFE Babysitter Bondage! Barefoot Nanny 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?!

Includes 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 + 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 + VIDEO! What a day to become a member of Babysitter Bondage!

July 29, 2025 - TWO UPDATES THIS WEEK! 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!

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.”

Jackson looked to the floor. “No.”

“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!

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

Real-Life Babysitter Bondage Game! Natasha Flade Bound and Gagged in Red Sweater Dress, Pantyhose & Heels! Classic Bondage from 2005 – Now In 720p for Superior Quality!

Up first this week we have a video from a real-life babysitter bondage game that Natasha Flade did for Isaac's birthday. (The accompanying 56 high-res photos are in the member's photo section (July 19, 2025). This was shot in 2005, back when no-one could download a video more than a few minutes, and so it begins after you have your sitter all tied-up. Although it's short and sweet, the emphasis is on sweet!

Natasha Flade is your babysitter today. She's wearing a tight turtleneck sweater dress, pantyhose and high heels. Her mouth is stuffer and she's cleave gagged with a long scarf on top. Earlier, you had her stand and turn around to have her hands tied. Now there's tons of rope everywhere about her chest and thighs. You love how her boobies stick out tied-up like she is! Your pretty babysitter tried to hop away, so you told her the bad guys have made a call to take her away and she best try to get loose before they return!

Natasha puts on an awesome damsel show for you! She wiggles everywhere all over that sofa: sitting, then laying on her side. She shows off those sexy high heels and her lovely gagged face. She's the best pretend kidnapped damsel ever! It's so awesome to play a real-life babysitter game with sexy Natasha Flade!

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

July 20, 2025 - 2 Damsels! 2 Photo Sets! REAL-LIFE GAME! Babysitter Natasha Flade Tied in Sweater Dress & Heels PLUS Office Mom & Friend Britnigh Banks Play Tie-Up After Work, Their Heels Fall Off! 104 NEW Photos! (2,200 Pixels to a Side)

TWO PHOTO UPDATES THIS WEEK! In the first photoset we have 48 gorgeous photos of beautiful blonde Britnigh Banks and hot redhead Natasha Flade. And it goes like this:

It's your lucky day! When your Mom got home today from her office job, her hot blonde friend Britnigh Banks was with her! You always ask your mom if you can tie her up when she gets home, but now there's two to ask to play! To your surprise, Britnigh smiles and agrees. She thinks it will be a lot of fun! And boy of boy, it sure is! You tie them up together with their arms attached to each other and give them stuffer gags with a cleave on top. Natasha and Britnigh play up their damsel roles for you. They look so cute with their wide damsel eyes and expressions. Mom kicks her heels off and shows off her stocking feet. Then Britnigh's shoe falls off, so now you can see both their pantyhose-feet!

Then you hear Dad come in downstairs! When he sees what you've been up, he just laughs and says you're a great son to leave him a double present like this. He tells you to leave for a bit so he can play with the office mom and her friend by himself for a while. Sullenly, you go to your room, but you can hear the peals of laughter from the loft...Wish you were old enough to play Dad's games! Oh well, someday!

In the second photoset, we have 56 photos from a real-life babysitter bondage game. Natasha Flade is your babysitter today. She's wearing a tight turtleneck sweater dress, pantyhose and high heels. Her mouth is stuffer and she's cleave gagged with a long scarf on top. At your request, she stands and smiles, then turns around to show off her hands tied behind her back. There's tons of rope everywhere about her chest and thighs. You love how her boobies stick out tied-up like she is! Your pretty babysitter is having so much fun as she tries to hop away!

But she falls down onto the sofa, where she poses for you: sitting, then laying on her side. She shows off those sexy high heels and her lovely gagged face. Natasha puts on the best show for you, looking damsel-concerned at times, but mostly smiling and enjoying herself. And so are you! It's so awesome to play a real-life babysitter game with sexy Natasha Flade!

2 Updates! 2 Damsels This Week! What a day to buy a pass and become a lucky Babysitter Bondage member!

July 12, 2025 -- (1080p - 6:45 min.) Mom Natasha Flade & Friend Chloe Night Hogtied Barefoot in Robes for Video School Project! Classic Bondage from 2008 - Now in 1080p for Superior Quality!

2 Updates This Week! Up next this week we have a new 1080p video! Your mom's hot blonde friend, Chloe Night, spent the night at your house. Your Mom (Natasha Flade) and Chloe just got up from a girl's night of chatter. They're in their robes and barefoot. As they head into the kitchen for some coffee, you asked if they could help you with your school video project. You're supposed to be making a commercial about home alarm systems and want to demonstrate the pitfalls of not owning one.

Your mom knows this so-called video project is likely just a ruse to get her all tied up again, since it is your favorite thing to do after all! And she enjoys endulging you. But she's a bit worried what Chloe will say about this tie-up business. But Chloe just smiles and says, "Why not? What harm can it do?" The two ladies will soon find out!

Excited, you run and grab your bag of ropes and rope your mom and her friend into barefoot hogties. You tell them to pretend a robber got them because they never bothered to buy an alarm system. Now this robber is especially tricky: he tied the women together at their forearms to make sure they don't get loose! They both have been gagged with knotted cleaves, too.

Natasha and Chloe play up their parts really well! They roll and wiggle as best they can and mew and mmph dramatically. What an awesome sight! But then you disappear...The front door slams...What the heck?! Natasha and Chloe are more than a bit upset at this turn of events! They struggle for real now (and their boobies popping out!). Your mom has no clue what her son is up to, but one thing's for sure: you better hope they don't get loose before you return!

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

July 12 - Barefoot Babysitter Natasha Flade Plays REAL-LIFE Game! Tied-Up in Sundress and Cleave-Gagged!
48 NEW High-Res Photos! (2,200 Pixels to a Side)

2 Updates This Week! Up first in this week's update we have a never-before-released photoset from a real-life babysitter bondage game. Natasha Flade is your babysitter today. She's barefoot and wearing a cute sundress. Her mouth is gagged with a scarf. She stands and smiles, then turns around so her hands can be tied behind her back. Your babysitter is having so much fun!

At your request, she sits down and her ankles are tied crossed with her lovely bare feet and soles sticking right out at you! Natasha poses some more, looking surprised and contemplative at times, but mostly smiling and enjoying herself! And so are you! Your barefoot babysitter is so darn hot tied-up and cleave-gagged on the floor!

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

July 2, 2025 -- (720p - 8:30 min.) Mom Natasha Flade Plays Escape Challenge Game! Scoots Down the Stairs, Uses Bare Feet to Get Away! Classic Bondage from 2008 Digitally Remastered in 720p for Superior Quality!

2 Updates This Week! Up first this week, you convinced your Mom Natasha Flade to let you tie her up and then try to get away! You want to see if she can escape. Mom accepts the challenge and lets herself be bound hand and foot in her miniskirt and little top. You make her challenge harder by binding her elbow tightly and wrapping more ropes above her knees.

You tell her she’s been kidnapped and must get loose before the bad guys return. Natasha really plays up her part of the damsel in distress! She crawls and scoots down the stairs, with lots of closeups of her soles and her cute panties poking out! Mom finally makes it to the front door and uses her bare feet to try to turn the door knob, but she doesn’t succeed.

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

July 2 - Office Mom Natasha Flade Chair-tied in Red Suit & Stockings, then Her Heels Come Off! 83 NEVER-BEFORE-RELEASED 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. They were shot on a lark one day for Isaac W.’s birthday. He told Natasha his fantasy and she just ran with it, adlibbing everything. The game begins with office mom Natasha Flade in her red secretary suit, pantyhose and high heels. She's standing as she teases you, pretending to ponder your request to play a tie-up game. Then she throws her hands up into the air and does your bidding. She turns and crosses her hands behind her back to be tied up.

Your mom poses like that for a bit, then she winds up chairtied! Her hands are tied behind the chair back, her ankles bound and tethered to the base of the chair. Natasha vacillates between surprise, concern and amusement. She really enjoys putting on the damsel show for you and goes along with your request to tie her up even more! Now she's strictly tied to that chair with ropes wrapped everywhere about her chest and lap. She poses more, making the best damsel expressions ever. Then her heels fall off! You don't mind, in fact, you LOVE it!

For your final request, Natasha gets OTM gagged with a thick black scarf. Our office mom looks simply smashing! We get lots of closeups of everything: pantyhose feet, lacy thigh-high stockings peeking out, the tight rope work. She's looking right into the camera at you with her beautiful and wide damsel eyes, smiling a lot then pleading to be released. Natasha knows that really turns Isaac on. (And you, too!) At the end, she gag-talks that you should let her go now. But you don’t plan to let her loose. We think she knew that the entire time, but Natasha’s not one to turn down a request to fulfill your real life MILF bondage fantasies!

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

June 26 -- (720p - 2:40 min) Classic Bondage from 2000 – Re-Edited in 720p for Superior Quality! Up next in this week's update, we've got two young college girls, Tabitha Katz and Olivia Simon (first time tied!), bound and gagged in a university apartment. Short but sweet, this video is sure to get your blood flowing!

As a little background here, Tabitha introduced producer Isaac W. of Centaur Celluloid to Olivia; it turns out that they both had had the same babysitter when they were growing up!

Olivia offered up her university studio apartment for a bondage shoot and agreed to be tied-up together with Tabitha. So Isaac bound and ball-gagged the two hotties back-to-back on a little table: hands bound in front and tethered to their laps, ropes wrapped about their chests, ankles tied. Both girls are scantily clad in skimpy shorts, miniskirt, and little flimsy tops. The newbie Olivia Simon is barefoot, but Tabitha kept her heels on.

They really entertain us with their helpless struggling and mewing. There's great close-ups of the tight ropework, their ballgagged faces, bare feet, heels, body slides of their tight young bods!

Since this was shot way back in the day of dial-up internet, the video had to be kept pretty short. This is how bondage video got done back in the aughts - short and sweet but with lots of emphasis on sweet! If you're looking for some great classic bondage of college girls from the 2000s, this video is for you! Although the runtime is only 2:40 minutes, you won't find better vintage bondage footage or hotter chicks! Enjoy!

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

June 25 - Busty Babysitter Chastity Rhoades Tied & Tape-Gagged in Denim Miniskirt and Pantyhose, Her Boyfriend Arrives to Get Her Topless! 47 NEW Photos (2,200 Pixels to a Side!)

Up first in this week's update is beautiful and busty babysitter Chastity Rhoades. And boy oh boy, she sure is hot! She always wears these skimpy tank tops and you can see her cleavage everywhere! How many fantasies you've had of her boobs just popping right out! But the best part is that she always lets you play your favorite game: tie-up! Today you're a CIA agent and you suspect she's KGB. You tell her you have to keep her captive as part of a sting operation.

Chastity laughs at your imagination, but she goes along like she always does and soon finds herself tied up on the sofa. You bound her wrists behind her back, her thighs are roped just above the knees, and you tied her ankles apart to the sofa legs. A red tape-gag seals her lips. She looks simply smashing!

Chastity poses and plays her part of the kidnapped damsel and her expressive eyes make you think you're going to faint! She leans over as she playfully struggles in her bonds and for a minute, you think your dream of her titties popping out will come to fruition, but nope... Still, you're mesmerized! Her denim miniskirt hikes up a bit so get some peeks at her panties, and her wiggling pantyhose-clad feet are the icing on the cake. It's bondage sensory overload!

Then the doorbell rings. It's her boyfriend! You're worried what he'll say, but to your amazement, he's more than happy to see Chastity all bound and gagged. "Wow, you left a present for me!" he says with a wink. Then he tells you to scram for an hour so he and Chastity can be alone. Reluctantly, you sulk off into your bedroom. But you can hear delighted squeals coming from the loft. You drift away into your fantasy land, waiting for the day when you can play those kinds of games with your hot babysitter!

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

June 9 - Mom's Smoking Hot Friend, Justine Adams, Hogtied & Triple Gagged in Stockings, You Fantasize She's Half-Naked! 41 NEW High-Res Photos (2200 pixels to a side)!

Mom's friend, Justine Adams, is smoking hot! Damn, that girl could set the house on fire. She sure sets you on fire! Today, your mom had some errands to run, so she asked Justine to watch you for a while. You can't believe it. You get to be alone with Justine.

Justine doesn't know it, but you have a little secret: you fantasize about tying her up. With your mom away, you decide to take your chances and go for it. You ask Justine if she'd like to play a game where someone breaks in to rob the place and they tie her up so she can't call for help.

Justine thinks about it for a minute, then she smiles and agrees. Wow! You're in heaven! So now you have her strictly hogtied on the bedroom floor with her elbows bound. She makes the most delicious pouty damsel expressions. Just amazing! Then you ask Justine to open wide her mouth and in goes a wad of cloth. Justine's eyes grow wide as she gets cleave-gagged next. But you're not finished yet! Next, you add an OTM gag on top. Now she can't call anyone for help. In fact, all she can do is make little mews through those huge gags you gave her!

Justine rolls and wiggles around, showing off her stocking feet. Her dress hikes and you see her thong panties poking out. You don't let her know, though...Why ruin a good thing, right? Then you wander off into fantasy land where Justine's dress slips down to reveal her gorgeous boobies. Her dress slides up even higher, so you can see her hot ass, too! Justine's not aware that you're imagining her half naked as she continues playing up her role as the bound and gagged damsel who got tied up by some bad guy.

What a day to become a member of Babysitter Bondage!

May 28 - Hotties Danielle Trixie & Natasha Flade Play Home Intruder, Get Tied Barefoot to Railing, then Dad Comes Home to Get Them Topless! 44 NEW High-Res Photos (2200 pixels wide)!

2 Updates This Week! Up first this week we have 44 photos of two hot AF babes, Danielle Trixie and Natasha Flade. Your Dad hired two of the most smoking hotties he could find to watch you while he works. You're pretty sure he just hired them because they're young and gorgeous. That sweet old grandma he fired did a fine job...No, she wasn't smokin' hot, but she let you play your favorite game: tie up the babysitter!

So now here you are with these two newbies and you're not sure if they'll go along with your fave game. But you take a deep breath and ask if they'd like to play this game where you pretend you're a robber and you break in and hold them up. Your Dad told them to keep you entertained, so Danielle and Natasha agree. You explain the game and have Danielle stand at the balcony rail so you can sneak in and handgag her! Now that blonde Danielle is barefoot in little shorts and a tight tank top. She's not even wearing a bra, which makes it hard for you to concentrate!

But you really want to tie her up! So you pretend to grab and drag her to the floor. She had to kneel first at the railing because she's taller than you. (Hey, you're creative.) Then Danielle winds up cleave-gagged and tied seated on the floor to the railing, her hands bound behind her, her bare feet and soles sticking straight out. Just the way you like it!

Natasha Flade is pretending to be Danielle's roommate. She's barefoot and wearing shorts, too. Natasha pretends to come home and finds her friend all tied up and gagged! She rushes over and tries to untie Danielle, but when she bends down, you jump her and handgag her! Then she suffers the same fate as her pretty blonde friend, Danielle, so now you have your two beautiful babysitters tied up barefoot and in pretty tight bondage, too. You've been practicing! Both are cleave-gagged with their pretty soles on display! You tell them to struggle for a bit before the big, bad robber returns. Danielle and Natasha laugh. They think this game is cute and so they mew and wiggle. They're so amazing!

But then your Dad returns home unexpectedly! Your mind is racing; what's he going to say when he sees you have the new babysitters all tied-up and gagged? You rush to untie the girls, but your Dad is already there! Wait a minute...your Dad's the one who gave you the idea for this particular tie-up game. He even bought you brand new rope. You're not stupid. You're thinking now that Dad just wanted you to tie the new sitters up for him! He tells you the game has a new ending. But you can't watch until you're 18. Uggh! You can't believe your Dad stole these gorgeous girls for himself! You sulk and go into your room to fantasize about what your Dad is doing with those girls.

What he's doing is this: Dad tells the ladies he's playing the big, bad robber now. But no worries; they'll each get a $200 tip for their trouble! Natasha and Danielle exchange looks. What's this situation they've gotten themselves into? And he doesn't think they're for sale, does he? He seems pretty cool and $200 is a lot, so they tell Dad to just keep his hands off their goods. Dad agrees, happy just to see their lovely titties. He pulls their tops up and the two damsels struggle while Dad watches it all: amazing shots of their bare feet and soles, gagged faces, and jiggling tits! Spoiler alert: Dad gets some feelies in of those boobies in the video to this photo set!

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

May 28 -- (12:12 min) Classic Bondage from 2008 – Re-Edited in 1080p for Superior Quality! Creatively shot POV-style from YOUR point of view! Nanny Natasha Flade (barefoot in jeans and a cute ski top) is watching her new boyfriend’s sons for the day. You ask to play a game of "spy" where she's the bad spy who's taken prisoner by the good spies (YOU!). Natasha laughs and throws her hands up with pretend fear. She's soon chairtied with her hands behind the chair back, her bare feet bound and ropes about her lap.

Now it's time to gag her! Natasha says she'll be good and you don't have to do that. But you don't listen! Her mouth is stuffed with cloth, then tons of duct tape are layered on top! She’s not happy about this state of affairs and protests vehemently in gag talk, but you can't make out what she's saying because her tapegag is so huge! Being the naughty boys that you are, you secure her to the chair with yards of duct tape and electrical tape wrapped everywhere. She’s truly helpless now! You guys leave and Natasha mmphs and struggles hard in her tape bondage, rocking that chair back and forth so hard she nearly breaks it!

When Natasha’s boyfriend, Isaac W., returns home, he finds her all taped up to the chair! Natasha tries to tell him to get her out of this mess, but his boys have his new girlfriend just the way he likes her! He takes advantage of the situation and uses a knife to cut holes in her top so her boobs poke out. Then he fondles and kisses her tits. Natasha is getting annoyed, but Isaac is having a really great time! He grabs another chair and props her bare feet atop it and ties them with her soles sticking right out. How tempting they are! He starts tickling her soles. Being extremely ticklish, Natasha's squirming all over the place and wiggling her bare feet frantically! She doesn’t like being tickled! But Isaac's having the best day of his life!

He leaves to go see what his two boys are up to, leaving Natasha bouncing and scootching her chair about in her efforts to free herself. She can't believe her boyfriend just left her like this! She’s not getting very far, though, which is okay with us as nothing's finer than a barefoot Natasha Flade tied and tapegagged with her bobbies hanging out!

May 22 - 2 Damsels! 2 Photo Sets! Dad Teaches You How to Hogtie Babysitter Danielle Trixie! PLUS Cousin Connie Sims Tied Barefoot then Her Boob Pops Out! 80 NEW High-Res Photos (2200 Pixels Wide) + 1000 Word STORY!

Point-of-View of Dad: I had left the babysitter, Danielle Trixie, in charge of my son Bentley as I ran a few errands. When I came home, she was on the floor with a scarf tied in her mouth! I was shocked in the best possible way! I mean, this babysitter is seriously hot. I could tell she was cool with the game by the pretend horror in her eyes. I laughed at her predicament and Bentley was happy to show off his captures. I was about to tell him that he shouldn’t be gagging the babysitter, but then I stopped as an (probably inappropriate) idea sprang into my mind. “Hey, Bentley, you want to see how to hogtie someone?”

“Yeah!”

“Mmmm?” said the sitter, her blue eyes wide. I helped Danielle to her feet and walked her into the bedroom. Danielle was cool with this new part of the game as I told her to lay down on the floor. She obeyed, looking up at me with the biggest and most beautiful damsel eyes I think I’ve ever seen. She was cool with it all as I tied her ankles together. Then I rolled her onto her belly and roped her bare feet to her bound wrists for a nice, tight hogtie. Bentley just stared at us the whole time. I think he was too enraptured to do much else. [...]

That’s when I decided to go for it. I told Bentley to inform his captive that the ransom money hadn’t come in and so he couldn’t untie her just yet. She pretended to be shocked (or was it just pretense?) that she wasn’t going to finally get untied. Then Bentley left and I gave him $50 bucks to run down to the arcade for an hour.

I thanked Danielle for being such a good sport and shoved a $100 buck tip in the back pocket of her jeans. Yeah, I know that’s a lot, a real lot, but watching this hot babysitter hogtied on the floor, let’s just say that it was more than worth it. Especially with what I had planned. I asked her if she was okay if I pulled her top and jeans down just for a bit. Danielle gave me a look. She probably thinks I’m a huge perv. I am, but whatever, right? And hey, I just tipped her $100! [...] The whole story is in the member area!

In the second photo set, your hot cousin Connie Sims is watching you for the afternoon. She's pretty lazy and was just laying around on the sofa. She looked so hot like that in her super short denim shorts, and a top that barely covered her huge boobs. I mean, come on, they were practically falling right out of her top! She looked up at you with a bored expression on her face. "You want to play a game, I take it?"

I nodded and asked if we could play robbers. "Again?! You just like tying me up!"

Well, yeah, of course I do. Connie went along and soon found herself bound and gagged, her bare feet dangling off the end of the sofa, and a huge stuffer gag in her mouth! She's pretty good at playing up her damsel role, I'll give her that.

Then something amazing happened! Connie didn't notice, but one of her nipples had escaped. I didn't say anything. I know that's not nice, but whatever. I'm just a boy, right? But eventually, she looked down and saw her tit poking out. She gasped and her eyes grew even wider. "Cover me up!" she tried to say but it was all muffled by that huge gag. I pretended I didn't understand what she say saying and tried not to laugh as her struggling got a big more frantic.

That's when Dad came home! Cousin Connie sure was embarrassed to have my Dad find her tied up and gagged and her nipple poking out! He gave me a lecture and told me the game was over. He's going to untie my cousin. Or so he said...

2 Damsels! 80 NEW High-Res Photos + STORY! What a day to be a Babysitter Bondage member! ALL these exclusive, brand new pics plus the entire story are yours today if you buy a PASS!

May 13 - (1080p - 8 min.) TWO DAMSELS! TWO UPDATES! Barefoot Nanny Natasha Flade Plays Cops 'n Robbers! Tied With Jump Ropes & OTM Gagged In Sundress! Classic Bondage from 2002 – Digitally Remastered in 1080p for Superior Quality!

TWO UPDATES THIS WEEK! Up first, we have a video that is especially dear to me (Natasha Flade). Isaac W. had an idea to shoot a movie that was entirely from the boy’s point of view, voice and all. No one had done such a thing in the bondage world. “The Nanny” was an immediate hit and, I believe, set the tone for my career in the years to come. I poured my heart into the digital remastering of this footage so my fans could enjoy a superior video. I hope you enjoy it as much as I do. ❤

Natasha Flade plays Kelly, who's been hired to babysit Joey and entertain her little charge. The video begins with Joey sneaking downstairs as he explains how much he's been dying to tie up his beautiful babysitter. He's been too shy to ask, but today he finally gets his nerve up. He approaches his nanny, who's on the sofa reading. She's wearing a sundress and barefoot. Kelly smiles and asks if he'd like to play a game or go to the park. Joey takes a deep breath and says he'd really like to play a game called cops 'n robbers and explains that first he's the robber, then he comes back as the cop to rescue her.

Kelly isn't quite sure about letting her charge tie her up, but decides it's harmless enough and plays along. Joey pulls his toy gun and Kelly throws her hands into the air, then holds them out in front to be tied up. Soon she finds herself bound hand and foot with jump ropes! Our nanny playfully struggles as the "robber" burgles the house. Then she starts to call for help. Joey can't resist this opportunity! He wasn't planning on gagging her, but she's practically begging to be gagged! And now our nanny is OTM gagged with a thick white napkin, detective style.

May 13 - 72 High-Res PHOTOS! Blonde Babysitter Justine Adams Tied on Sofa in Miniskirt, Boyfriend Arrives to Get Her Topless & Have Some Fun! 2200 Pixels High - Perfect for Your Huge Smartphone!

TWO UPDATES THIS WEEK! Up next in this week's update we have 72 gorgeous photos of beautiful blonde Justine Adams. And it goes like this:

It's your lucky day! Your mom left to do some errands and asked that hot AF blonde chick down the street to watch you. Justine Adams strolled on in wearing a tight-ass top, strappy summer high-heels, and a miniskirt so short you could see her panties poking out! Damn, she's so smoking hot you think the house is gonna catch on fire!

She greets you with a smile and you can barely reply, you're so flustered. But your mind is racing a million miles a second with all the things you've dreamed of doing if ever you were alone with Justine! Now's your chance! She asks you what you want to do for the afternoon and you blurt out, "Do you like to play robber games?"

"Robbers? How's that game go?" Justine asks you.

You say you'll show her and run and grab your bag of ropes. Justine's surprised when she finds out you plan to tie her up! But she's sweet and goes along. You tie her hands and ankles, then attach her wrists to her knees. You hope she doesn't notice you staring at her undies while you're finishing up those knots...Or her cleavage pouring from her top...

Justine makes the most perfect damsel! She poses and pouts for you, pretending she's been robbed and all tied up by some bad guy. She tries to call for help, getting into the game. Great! That's your cue to say she's got to be gagged, too! So she gets a knotted scarf between her lips. She poses and pouts some more, wriggling in those bonds you tied so well.

Then the doorbell rings. It's her boyfriend, James. He thought since no one was home, he'd stop by and have some fun with Justine. Crap. Just what you need. A third wheel. Justine's sort of nervous what James will think about her being all tied up and gagged -- and by a kid no less! But when James sees Justine, he grins and tells you thanks! Turns out he's always wanted to play bondage with Justine, but he was too shy to ask. Now you've done the hard part and James can have some fun! He tells you to come back in an hour and locks the door behind you. Man, you wish you were in that room. Sure sounds like they're having lots of fun. You sit in your room and fantasize that Justine's still tied up on that sofa, but now with her boobies hanging out!

2 Updates! 2 Damsels This Week! What a day to buy a pass and become a lucky Babysitter Bondage member!

May 3, 2025 -- (FULL HD - 10:15 Min.) NEW FOOTAGE IN FULL HD!

Up first is a never before released video. You’re a young guy who’s really into bondage, but you’re terribly shy and a recluse who can’t even leave your house. That makes it rather hard to fill your needs. So you hire sexy private sitter Natasha Flade to help you out around the house, do your shopping and just sit and talk to you. Now you two have become friends and you’ve disclosed your bondage fantasies to her.

Today, when your bi-speckled sitter Natasha visits, you gather up your courage and ask to play a role play game where you kidnap her. Natasha says that sounds like fun, then announces that she has a surprise for you. She produces a scarf and some rope from her purse. She wants you to practice your bondage fantasies by tying her up. You’re overwhelmed and shocked, but really excited, too.

Natasha says she’ll start the game and gag herself, but makes you promise to tie her hands afterwards. You watch as Natasha gags herself, then she holds her hands out in front for you to tie up. You oblige your pretty sitter and stare as she sits there on the sofa, bound and gagged, and gag-talking about how much fun it is to be tied up by you.

But the biggest surprise is yet to come! Natasha reveals that she has a secret crush on you and she’s been dying to have you tie her up and gag her. She really brought the rope and scarf for her own ulterior motives. She tells you how excited it made her watching you tie her hands together and asks you to tie her up even more. You’re in ecstasy! What a lucky day for this young shy guy!

Natasha Flade is wearing a long skirt, pink sweater and sexy glasses in this video.

May 3 - Candle Boxxx Hogtied Barefoot, then You Fantasize She's Naked! 73 NEW High-Res Photos! (2200 pixels wide)

Up next in this week's update is sizzling blonde Candle Boxxx hogtied in a t-shirt and miniskirt, barefoot. You convinced her to play a game like you saw on TV where someone broke in and tied up the wife. Candle thinks it's cute and plays along. She's so awesome with her pouty damsel expressions and smiles. She even agrees to a cleave gag. You watch with sheer delight as she wiggles and poses for you. Candle sure is hot! And she really knows how to show off that amazing body!

As you sit and stare, your mind wanders off into fantasy land. Candle is unaware that you're imagining her with her clothes suddenly disappearing! First, she's topless, then her miniskirt hikes up to reveal that she's not wearing any panties! Everything is on display! She smiles at you as you oggle her ass and those amazing breasts. You hope you never wake up from this dream...

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

23 April - 2 Damsels! 2 Photo Sets! Babysitter Danielle Trixie Hogtied then Dad Gets Her Naked! PLUS Nanny Natasha Flade Plays Your Game: Ghairtied in Jammies, Sock-Gagged, then Wrap Gagged! 96 NEW High-Res Photos (2200 Pixels Wide)

In the first photo set, hot blonde babysitter Danielle Trixie agreed to play tie-up with you. You have her strictly hogtied on the garage floor in her sundress and strappy sandal heels. She's stuffer gagged with clear tape holding it in. Damn, she's smokin' tied-up like that! Her boobs are practically falling out of her dress as she wiggles around, playing the damsel for you.

Then you hear a knock. It's your Dad! What's he going to say about this tie-up business? Before you can figure out what to do, he comes strolling in. Danielle is pretty nervous about this, but your Dad just laughs. "I see you've been tying up the babysitters. Just like I did when I was your age." You laugh nervously, then Dad hands you $20 and tells you to scram. Danielle looks at you with wide and worried eyes, but you don't know what else to do...except leave.

Poor Danielle soon finds out your Dad loves bondage even more than you do! And he likes to see his damsels a bit more naked. You don't know what happened, but you hope Danielle spills the beans one day when you're older!

In the second photo set, nanny Natasha Flade, barefoot in jammies, is roped to a chair. Her wrists are tied to separate chair arms and there's rope is wrapped about her chest. She's so cute as she poses for you, testing her bonds and exclaiming that a big, bad robber got her! Then you tell her you want to tie her ankles, too. Natasha teases you by kicking her feet out and laughing. But she goes along and now her bare feet are tied and tethered to the rungs at the base of the chair.

"You want to gag me, too?" your nanny exclaims. She pouts and frets, but winds up with a big white sock stuffed into her mouth! She poses some more for you and gag-talks that she doesn't know what on Earth will become of her now. You think she's making too much noise; you don't want the neighbors to hear! So you wrap an ace bandage on top of the sock gag. There! Now she can only make little mews and mmpphs, but Natasha still plays along because she loves playing tie-up with you. It's her favorite game to play with you! You lucky boy!

2 Damsels! 96 NEW High-Res Photos (2200 Pixels Wide)! What a day to be a Babysitter Bondage member! ALL these exclusive, brand new pics are yours today if you buy a PASS!

15 April -- Barefoot Babysitter Quimm Anaheim Tied Ass-Up on Bed PLUS Aunt Natasha Flade Tied in Pantyhose by Her Nephews! 70 NEVER BEFORE RELEASED High-Res Photos (2200 Pixels Wide) + STORY!

In the first photo set, Quimm Anaheim is doing an overnight babysitting job. She’s barefoot in bed when you approach and ask to play your favorite game where you tie the babysitter up! Even though it’s past your bedtime, Quimm agrees to play on the condition that you go to bed straight afterwards! You run and get your ropes and Quimm soon finds herself tied stretched out, belly-down, on the bed. Her cute ass is peeking out from her silk nightshirt, covered only by super skimpy thong panties.

Quimm realizes her ass is sticking out, and that you’re staring at it, too! (You little perv!) She doesn’t think your mom would appreciate this situation very much, so she demands that you either tie her up in a different position or at least pull her nightshirt down! Instead, she gets cleave-gagged! Now you're a naughty boy whose getting plenty of peeks at her exposed buns. This doesn’t make Quimm very happy to say the least. But oh, what a sight for you! Especially with her wriggling bare feet and soles! What a night!

In the second photo set, Aunt Natasha Flade is tied up by her favorite nephews after she got home from the office! You have her bound seated on the floor to table leg with her pantyhose-feet sticking straight right out at you! "Why is it every time you come over you have to tie me up?" Aunt Natasha laughs. She knows you guys just love seeing her all tied up! She teases you about staring at her feet and wiggles those stocking feet in your faces! Then she says that once you’re done staring at her pantyhose feet (which might be a really long time...), you should gag her, too! And so you do! Now she's cleave-gagged with a red bandanna to match her red dress.

Now Aunt Natasha is a real gag-talker and never shuts up! You wander round the table, staring at your hot aunt while she spins her tales. What fun! You love listening to Aunt Natasha telling stories while she's bound and gagged! Then she tells a story about how she let some boys tie her up for a game one time, but they didn’t tie her up as well as you guys do! That's no surprise because you two boys spend hours practicing your rope work, dreaming of all the ways you can tie up and gag your hot Aunt!

2 Damsels! 70 NEVER BEFORE RELEASED High-Res Photos (2200 Pixels Wide)! What a day to be a Babysitter Bondage member! ALL these exclusive, brand new pics are yours today if you buy a PASS!

April 8 - (1080p - 3:50 min.) NEW MODEL Sakura Sky! Babysitters Sakura Sky (with the HUGE tits!) & Natasha Flade Play Robbers, then Big Brother Strolls In to Get Them Topless! RE-EDITED IN 1080p for HIGHER QUALITY!

This video hasn't been seen it's original release date way back in 2006. It's been re-edited from the source tape in 1080p and stars Sakura Sky, who makes her video debut here on Babysitter Bondage.

Babysitter Natasha Flade invited her friend, Sakura Sky, to help watch Kyle, the boy she's watching. Kyle asked the two ladies to play a game of robbers. They thought it was cute, so Natasha and Sakura agreed to play the game.

Now here they are: both tied-up and gagged on the floor, bound to the dining room table. Their hands are tied behind the table legs, and their ankles are tied, along with more rope wrapped above their knees. The babysitter and her friend have been tape-gagged, too. Sakura's lips are covered with silver duct tape and Natasha's with yellow tape.

They struggle playfully, but it's not long before things take a turn! Their charge Kyle takes off, leaving his sitters all alone. Or so they think. Because once he's gone, in strolls his older brother! He pulls their tops down and their bras up, then he plays with Sakura's (huge) boobs for a bit!

Natasha and Sakura are shocked at this turn of events! They can't believe it! They've been pranked! That little brat Kyle is going to be in big trouble when they finally get loose!

Natasha Flade is wearing a denim miniskirt and t-shirt, barefoot. Sakura Sky sports a miniskirt, pantyhose and Baby Jane heels.

30 March -- Hot Babysitter Nessa Luscious Chairtied Barefoot (Backwards!) in Miniskirt, then Dad Comes Home to Get Her Topless! 61 NEW High-Res Photos!

You approached your hot Latina babysitter and asked her if she'd play robbers with you. She was skeptical at first, but then she went along. Yay! You're so excited! So now you have her tied-up on a chair, kneeling, her butt facing backwards and her lovely bare feet and soles pointing right at you. Just the way you like it! She's cleave-gagged with a thick scarf. Nessa wiggles around playfully for you, putting on a wonderful damsel show. Damn, she's hot in that denim miniskirt with her thong panties peeking out!

Then you hear a knock at the door. It's your Dad! You get nervous and try to loosen the knots as fast as you can. But you're not fast enough and in strolls Dad. You fear he'll be mad, but instead he says his son is a chip off the old block. You sigh in relief, but poor Nessa is looking concerned. It's one thing to let the kid tie her up, but what's this with the Dad?!

Dad hands you $25 and tells you to scram. Go see a movie or something. Not wanting to get into trouble, you take the cash and head toward the back door. But as you're leaving, you hear your sitter giggling. You're not sure what your Dad is up to, but it sure sounds fun! Maybe one day he'll tell you what happened. But the viewer gets to see it all -- beautiful Nessa with her boobies and ass hanging and as she poses and plays the damsel for Dad now, too!

61 gorgeous new high-res photos! What a day to be a Babysitter Bondage member! ALL these exclusive pics are yours today if you buy a PASS!

March 22 - (720p - 13:18 min.) Mom Natasha Flade & MILF Kordelia Devonshire Tied-Up Barefoot in Robes for Ransom Game, Molested & Tickled by Jasmine! RE-EDITED IN 720p for SUPERIOR QUALITY!

Blonde babysitter Kordelia Devonshire (with huge tits!) sips her morning coffee while watching friend Natasha Flade’s son. You stroll in and ask to play a game of hostage. Your mom said you weren’t supposed to be tying up the babysitters, but Kordelia laughs and goes along when you pull your toy gun and order her to sit on the floor and cross her hands behind the table leg. Kordelia is now all tied up barefoot in her robe, chest ropes encircling her prodigious chest!

She struggles playfully for a bit, then in walks your mom Natasha in her flimsy, silk robe. What’s this?! You’ve got the babysitter tied up again! Then you pull the toy gun on her! Kordelia thinks your mom should join in, too! So Natasha acquiesces to your hostage game and allows herself to be tied-up next to her friend to the other table leg. But they won’t stop chatting, so MILF Kordelia gets a sponge ball shoved into her mouth. Natasha is stuffer gagged. Now you have your mom and sitter both tied-up barefoot in their sexy robes, their bare feet and soles on display and wriggling all about! Wow! A dream come true! You leave them there like that to struggle a bit.

But wait, there’s more! Jasmine Taliana comes strolling in and finds them! She says they’re naughty and must be punished. Just then, you come strolling in and ask Jasmine to play hostage, too. She says that wasn’t part of the deal and tells you to scram. But you’d really like to stick around. Natasha gag talks, “You can tie us up again later!” Awesome! So you head out, leaving your mom and babysitter alone with Jasmine and her scheming.

Jasmine wraps two scarves over the gags they already have, then sets to molesting poor Natasha and Kordelia! She pulls out their boobs and gropes and squeezes their luscious tits. As she’s fondling Kordelia’s ginormous breasts, Jasmine reveals this is all revenge and payback for when they found her tied up by Natasha’s son and molested her! Then she tickles their bare feet and soles. Natasha and Kordelia giggle and scream behind their huge wrap gags. Jasmine’s relentless with the tickling!

If you’ve ever dreamed of tying up your mom and babysitter at the same time, if you’ve ever dreamed of two hot MILFs tied-up barefoot in robes, if you’ve ever dreamed of your mom and sitter getting molested by some hot chick…this is the video for you! A couple of bloopers and outtakes at the end!

12 March -- 2 Photo Sets! 2 Damsels! Mom Natasha Flade Chairtied in Sundress for Your Dad's Magic Trick PLUS Babysitter Daphne Paige Bound Barefoot in Jersey! 112 NEW High-Res Photos!

In the first set, your cute blonde babysitter Daphne Paige has agreed to play a tie-up game with you! You can't believe it! So now she's bound barefoot on the floor in her jersey top. You even gave her elbow ties. Daphne's a bit surprised at that, but boys will be boys she says. She even agreed to a stuffer gag with a cleave-gag scarf on top. What a cool babysitter she is to go along!

She's rolling all around, playing up her part of a real damsel in distress who's been taken hostage for ransom. But as she's wiggling, her top slips up! You don't say anything, just stare a lot at her boobies and her hot ass in thong panties. Wow! You hope she doesn't notice...or tell your mom you saw her tits and buns!

In the second set, you told your mom Natasha Flade that your Dad asked you to tie her to a chair for his special magic trick. "Magic trick?" Natasha says with a smile, but she plays along, pretending to be alarmed but she's also amused, especially when you give her a knotted cleave-gag. She wiggles playfully in her chair, kicking her heels and just having lots of fun.

After a while, mom wants to know when is the magic trick going to happen? You tell her that your Dad has special powers and run off to fetch him. Dad shows up and announces that he has special powers that make her clothes disappear! And so the top of her pink sundress falls off! Dad just laughs at his "trick." The real trick was getting his son to tie up his wife so he could see her boobies!

TWO damsels, TWO tie-up positions, 112 gorgeous new high-res photos! What a day to be a Babysitter Bondage member! ALL these exclusive pics are yours today if you buy a PASS!

March 4, 2025 -- (FULL HD - 11:45 Min.) BRAND NEW FOOTAGE IN FULL HD!

Hot MILF Natasha Flade is sitting on the bed reading when her son comes in to remind her that his cousins are coming over. Natasha knows they’re just coming over to get her all tied up. After all, it’s their favorite game! The doorbell rings and Billy rushes off to let them in.

Now our hot MILF is hogtied on the bed in her little white sundress, barefoot. Natasha teases the boys about how much they love to tie her up. Heck, they probably don’t even play with her son — just come over to tie her up! And what’s this with her elbows bound, too? She thinks it’s a bit too much. Who have they been practicing on? Their own moms? No? She’s not surprised since they probably want to tie their elbows, too!

She asks how this game goes anyway? Kidnap or robbers? What’s the plot? Better not be just leave poor mom here all tied up on the bed and take off with the car! She tells them what lucky boys they are to have a Mom and Aunt who goes along with all their games. And enjoying herself, too!

That’s when she winds up cleave-gagged! “What’s this? Oh, I’m talking too much?” Natasha chides. “No gag can stop me from talking. It’s impossible!” But the boys want to see if it does. Ha! Nothing can stop this chatter box from her constant gag-talk.

She rolls and wriggles, showing off her bare feet and soles (and a nipple here or there…), and gag-talking nearly the entire time about how much fun she’s having and how she loves being tied up. The kids think it’s cute. But hottie MILF Natasha eventually gets upset when she discovers her son and nephews have run off and left her! She is an awesome Mom and Aunt, but enough is enough! She starts to plead, then resorts to threats and bribery.

But none of it works. Turns out this poor mom has been left all tied up and gagged on the bed just as she feared!

February 21, 2025 -- (FULL HD - 10:20 Min.) BRAND NEW FOOTAGE IN FULL HD!

Your sexy mom Natasha Flade is barefoot in her robe when she’s approached by her son to play a game. “Can’t you see I’m getting ready for bed?” she tells you. But she relents (as she always does for you!). “Ok, just one game. What would you like to play?” You tell her you’d like to tie her up to a chair and Natasha laughs. “What? You must be kidding!” But she goes along and winds up chairtied. She’s surprised how well you tied her up and she’s pretty impressed! Then she asks how this game goes. Does she wiggle around, maybe try to get loose? All that sounds just great to you.

Your sexy mom wiggles around playfully in her chair, testing her bonds, of which there are plenty! Then you decide she’d look even better with a gag, so now Natasha is cleave-gagged, too. She makes the cutest mews and mmphs as she’s wriggling about, laughing and smiling a lot, too. Seems your mom likes this game as much as you do! After all, she knows she’s one hot barefoot MILF! You run off to hide and watch as mom continues playing up her damsel part.

Then she notices her boob is coming out of her robe! She starts to panic and calls for you to come back and untie her. But you don’t come back…! She struggles harder now, worried that you’ll see her tit hanging out! She’s jumping that chair up and down, back and forth. The result is that now both her boobs have fallen out! And her panties are poking out from beneath her robe, too! Mom Natasha starts getting a bit distressed and angry that you won’t come back, so she can cover herself.

But what fun would that be? It’s just way too much fun to watch your sexy mom struggling (now quite angrily) all tied-up and gagged with her tits swinging around!

February 12, 2025 -- (FULL HD - 7 min.) NOW IN FULL HD!

Beautiful and sexy blonde Danielle Trixie just got home from her secretary job. As she sits down on the sofa, still in her tight office dress and high heels, she gets a call from a friend who's in need of a babysitter for her son, Jimmy. Danielle isn't keen at first, but she agrees and the boy arrives shortly. Now Jimmy thinks his new babysitter is hot AF and what he really wants to do is to tie her up! So when Danielle asks if he wants to play any games, he jumps at the chance! He eagerly tells her that he wants to play this ransom game where he ties her up.

Danielle isn't sure about letting herself be tied up by a kid, but he convinces her by saying that he ties up all his other babysitters. Danielle thinks it's cute, so our gorgeous babysitter goes along with the game. At his request, she puts her heels up on the ottoman, then she lets herself be tied hand and foot, hands bound together in front, ankles tied crossed. Danielle pretends she's a helpless damsel in distress, mewing and struggling (playfully and sexily!) for your amusement. Those high heels up on the stool are hot to watch and when she wriggles about, you can see her panties poking out! Wow! She compliments your rope work, then agrees to let herself be OTM gagged with a bandanna scarf!

Then you ask if she can take her shoes off so you can see her bare feet. Babysitter Danielle is so great! She agrees to your request and dangles her heels off the ottoman until they fall right off! Now she's tied-up barefoot, and you sit and stare at your sitter's beautiful bare feet and soles! You just love Danielle Trixie for playing your game and letting you tie her up! She's your very favorite babysitter because it's tons of fun watching this super-hottie put on a damsel show while she's babysitting you!

3 February -- 2 Photo Sets! 2 Barefoot Damsels! Cute Babysitter Sindy Lee Chairtied in Dress PLUS Nanny Daphne Paige Bound Hand & Foot in Jeans! 92 NEW High-Res Photos! (2200 pixels wide!)

In the first set, your cute babysitter Sindy Lee has agreed to play a tie-up game with you! You've got her tied to a chair with a ton of rope everywhere! Sindy plays up the damsel part, pretending to be scared and shocked. She makes the best expressions! Then you announce that she has to be cleave-gagged so she can't call for help. Sindy goes along with that, too. She playfully struggles for you, her damsel eyes amazing, her boobies practically falling out of her dress! Damn, she's so hot!

In the second set, blonde nanny Daphne Paige agreed to your game of "hostage." She's so beautiful tied up and cleave-gagged on the sofa in her tight tank top and jeans. Her bare feet are simply perfect, and they look even better with the ropes you wrapped about them! Daphne is smiling and having a super fun time. She wiggles around, mews through her gag, and pretends to call for help. But you know she doesn't really want to be let loose. Look at all the fun she's having!

What a lucky boy you are! Your nanny and babysitter both tied up and gagged, happy to indulge you. Maybe you can get mom to hire another sitter or two that you can tie up...!

TWO barefoot damsels, TWO tie-up positions, 92 gorgeous new high-res photos! What a day to be a Babysitter Bondage member! ALL these exclusive pics are yours today if you buy a PASS!

January 26, 2025 -- (FULL HD - 10:45 Min.) BRAND NEW FOOTAGE IN FULL HD!

Mom Natasha Flade is sitting on the bed in her red dress and pantyhose. She told her two sons they could play a tie-up game after she got home from work. "You guys said you wanted to tie me up," Natasha says, smiling. "So go grab your ropes and gag. I'm waiting to be surprised!"

And so she is! Now you have your mom bound hand and foot: hands and ankles tied crossed, ropes wrapped about her chest, stocking-feet pointing straight out. She's cleave-gagged with a polka dotted bandanna.

"Here I am!" Natasha exclaims. "You've got mom all tied up after the office. So what do I do now?" You tell her she has ten minutes to get loose. A challenge! Natasha accepts, sure she'll win your bet! She starts to struggle, laughing and gag-talking. She puts in a really good effort, wiggling all over the place. (She knows you like that part.) But the ropes are tighter than she expected and after a bit, mom starts to worry that maybe she won't get loose after all!

Now mom tries even harder! She's determined not to lose your escape challenge! She rolls onto her belly and tries to undo the knots on her ankles. She gives it her best shot, with great close-ups of her pantyhose feet. It's a valiant effort, but she doesn't succeed. And to make matters worse, you boys have run off and left her there all tied up and gagged on the bed!

"I hope you're entertained!" Natasha says. This is a mom who loves to talk, gagged or not! Wow, this is a lot more work than she expected! Eventually, Natasha concedes she can't get loose after all. "I give up!" she calls out. But you two guys are nowhere to be seen. Is someone going to come back and let our poor office mom go? Nah...!

Cute outtakes included at the end!

24 January -- Hottie Sister Antoinette Hogtied Barefoot in Miniskirt, then Her Boyfriend Gets Her Topless! 45 NEW High-Res Photos! (2200 pixels wide!)

My best friend's sister Antoinette sure is hot. I asked Kyle if she'd mind playing a tie-up game with us. He was skeptical, but he asked her anyway. When she agreed, I thought I'd die for sure. But I managed to keep it together and get her roped into a hogtie on the bed. It was amazing! Here she was, tied up and gagged on the bed. Her bare feet were so cute as she wiggled about. And she made lots of cute mewing from behind the cloth and scarf I'd used to gag her with.

But then there was a knock on the door. It was Antoinette's boyfriend here to pick her up for a date. Kyle and I exchanged looks. Oh boy, we're in trouble now for sure. But wait, we're not! This dude was pretty shocked to see his girlfriend hogtied on the bed like that. He shot us a look, then broke out laughing.

"How'd you guys manage to convince her to let you tie her up? I've been trying for months!"

We stammed and just said we were playing some robbers game. A lame excuse, but he didn't seem to care. In fact, all he seemed to care about was Antoinette tied up on the bed. We slithered off. What happened after that, I can't say because they locked the door. There was a lot of giggling and...other noises, too.

You can get ALL these exclusive, high-res photos (2200 pixels wide) if you buy a PASS!

January 18, 2025 -- (FULL HD - 15:10 Min.) BRAND NEW FOOTAGE IN FULL HD!

Mom Natasha Flade invited all her son’s friends over to have a little chat. She wants them to stop bullying Jordon — or else! She says they don’t want her going to the principal and she’s pretty sure they can settle this themselves. To her surprise, the boys offer a deal: they’ll stop teasing Jordon if Natasha lets them tie her up. What?! The kids explain none of the neighborhood moms will agree to being tied up, so here’s their chance!

Natasha goes along with the deal and winds up roped to a chair. Her hands and ankles are tied, lap ropes keep her secure, and the boys wrapped rope about her chest. That really makes her boobs stick out in that tight tank top! Natasha thinks the deals done now, but no, there’s more! Those kids tells her she has to be gagged, too! Umm, no one mentioned that part. No matter. Mom Natasha now finds herself cleave-gagged with a thick winter scarf. “Oh, I see I’m gagged whether I like it or not!” Natasha chastises. But she plays along like the good sport she is. And she keeps on with her banter, only now it’s all in cute gag-talk.

The boys then explain she has to try to get loose, so Natasha does her best. But they did a really good job and the knots are just too tight! Still she gives it her very best shot, laughing and gag-talking as she’s struggling, rocking the chair up and down, to and fro.”You didn’t say I couldn’t have a good time while I’m at it!” she tells them. She certainly is having lots of fun!

But when 15 minutes go by, Natasha tells the boys it’s time to let her go. Do they? No, they don’t! Instead, they tie her bare feet atop a second chair — and stare! The boys (and the viewer) are treated to lots of delicious angles and close-ups of those wiggling soles, with those jiggling tits in the background. What a marvelous sight!

Eventually, mom concedes she can’t get loose. And your 15 minutes were up long ago! Then she sees you guys approaching. “Oh, there you are! Yeah, your time’s up. Let me go!” But you don’t want to…

Outtake at the end included with lots of gagtalk!

January 9, 2025 -- (FULL HD - 9:30 Min.) BRAND NEW FOOTAGE IN FULL HD!

Mom Natasha Flade is hosting her son Billy’s sleepover. She’s seated on the couch in her cute pajamas, barefoot. Next to her is a pile of ropes and a long scarf. Natasha excitedly tells you it’s the tradition to play tie-up with the mom hosting the sleepover. But you guys don’t know anything about that. Natasha’s surprised, but she’s going to teach you! She holds up the rope and gag and explains you’ll tie her up and then she’ll pretend she’s been kidnapped and try to get loose. “It will be fun!” she promises.

So all you guys agree and now Billy’s mom is bound hand and foot on the sofa, bare feet tied together, hands tied crossed behind her back. “See?” Natasha exclaims. “Isn’t this tons of fun?” She can’t believe the other neighborhood moms don’t let you tie them up, too!

Mom Natasha wiggles all around, pretending to be your hostage. She’s having a really great time! You boys are having a really great time, too! Billy’s mom is so hot all tied up with her long red hair, those sweet bare feet, and she’s nipping out through that tight pajama t-shirt top!

Natasha teases that she could just call out for help, so you have to gag her! And so you do! She gets cleave-gagged with three wraps of a scarf between her lips. Mom Natasha keeps on playing the game, playfully struggling and mmpphing like a real damsel would. How exciting!

But she could still hop away if she really wanted to…so you guys approach with more rope. Natasha’s eyes grow wide and she jumps up and down when she sees the rope! She’s so excited that you’re going to tie her up even more. She can’t wait!

Now you have your friend’s mom hogtied on the sofa! What a sight she makes! She’s laughing as she playfully struggles, pretending to be your kidnapped damsel, but she laughs and smiles a lot, too. She loves this game and it shows! You guys get to see lots of bare feet and soles from all kinds of angles. What an awesome mom Natasha is to play “tie up the hosting mom at the sleepover” tradition!

Includes a few cute outtakes at the end!