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

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

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

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

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

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

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

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

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

# # #

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

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

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

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

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

July 29 -- (720p - 3 min) 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!

TWO UPDATES THIS WEEK! 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 mom 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 DAMSELS! 2 PHOTO UPDATES! What a day to buy a pass and become a lucky Babysitter Bondage member!

July 12 -- (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 -- (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 – Now 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!

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