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 & VIEWING EXPERIENCE!

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 Gets 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.) Hot MILF Natasha Flade Strictly Hogtied by Nephews, Gets Gagged for Talking Too Much! 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!

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