SimmySammy

Cartoon of three girls in heavy bondage gear. They are shackled and chained together, and each of them wears an orange garment that is basically a table runner with a hole cut out for the head, it doesn't cover much. A pair of gloved hands reaches out to try and catch them

Prison break!!

Cartoon of a girl restrained in bondage gear. She's wearing an orange bodysuit and tall boots. Her torso is strapped inside a box that looks like an old suitcase, her ankles are cuffed and attached, and she's muzzle gagged. A large sticker reading "FRAGILE" has been placed over her left eye

Keep your luggage securely stowed for extended travel 💙

Cartoon of a girl in bondage. She's wearing a witch costume, tied with a chest harness and gagged. She's crouching behind a tree, looking back at the ghosts in the woods behind her

Very, very, very lost 👻🍂

It’s never too late to start!

Wow hello!! Howdy to all the new faces, thank you for checking out my goofy bondage cartoons 💙

Cartoon of a girl in bondage. She's wearing a muzzle and a butterfly straitjacket dress, and she's standing in a closet behind a tall pet gate. The muzzle is stylized to look like the muzzle of a dog, with a big nose and teeth. The straitjacket dress has the word "PET" printed on it, and cinches just above the knees.

Got a time-out for being too rowdy 😭

Cartoon of a girl in bondage. She's locked inside a piece of furniture that looks like an old secretary desk with big double doors in front—only her head is visible from the outside. She's wearing a harness panel gag with a plug, and she's looking at the viewer. The furniture sits next to a pair of banisters and a staircase, and a bright window sits in the wall in the background.

It can be a struggle to find the right decor to complement an old house 💙

Cartoon of two girls. One of them is tied up in a simple rope harness, and wearing a t-shirt that says "UH-OH". The other is standing close behind her, hooking her fingers into the other's mouth and holding her mouth open. The girl in the back says "Big mouth", and the tied-up girl in front says "Haggh"

Jerk Bullies Local Nerd

Ach, should’ve reposted this on the 1st. Happy Kinktober, weirdoes! I’m there in spirit, if not in practice

Cartoon of a girl in bondage. She is wearing a t-shirt, a chunky spiked collar, and a ball gag, and her arms are restrained with a bit of rope

Keepin' it casual 💙

Oh wow the compression on bsky is horrible. It looks a little less bad here? www.deviantart.com/simmysammy/a...

Sequel to this one here

Cartoon of two girls in bondage. One of them is kneeling and strapped down to a cart, gagged and collared. The other is pushing her along, wearing goggles and a respirator

More testing required—right this way!

Cartoon of a girl in bondage gear—we see two figures, both the same person, wearing different clothing. The figure on the left is wearing a shirt and skirt and sandals and is smiling broadly. The figure on the right is wearing bondage gear, blindfolded, muzzle gagged, an armbinder, and leg cuffs, all secured with many straps

Before and after 👀

Cartoon of a girl in bondage. She's handcuffed and gagged, wearing a short dress and looking surprised, and lying down in a person-sized hole in a wooden floor, with a heavy lid and a series of padlocks resting nearby

Sammy looks surprised to find herself holed up! At least it's just for a little while ... right??

Cartoon of a girl in bondage. She is muzzle gagged, kneeling on all fours, and tethered to the floor. A fantastical looking mechanical arm approaches her naked butt

This exam looks a little, uh ... invasive 👀💦

Happy new year's! Stay toasty in 2025 💙

Cartoon of a girl in bondage wearing a reindeer outfit

Happy holidays!!

Cartoon of a girl in bondage gear. She's sitting with her legs splayed, and her legs are bolted to the floor at her ankles and above the knees. Her hands are locked in a hand pillory which is attached to a chain that is bolted to the floor. She's wearing close-fitting shiny pink clothes, stockings, gloves, and collar, and she looks mildly worried

Sometimes you just feel like a sitting duck

Cartoon of a girl in bondage gear—we see two figures, both the same person, wearing different clothing. The figure on the left is wearing a shirt and skirt and sandals and is smiling broadly. The figure on the right is wearing bondage gear, blindfolded, muzzle gagged, an armbinder, and leg cuffs, all secured with many straps

Before and after 👀

Cartoon of a girl in bondage. She's restrained in a ball-tie position by an orange harness and wearing a muzzle gag. Another woman lifts her into the air via a handle on the back of the harness, but appears to be struggling. Lifter: "You BETTER fit in the overhead." Restrainee: "Nngh!"

Not every passenger wants to deal with the hassle of checking their luggage...

Cartoon of a girl restrained in bondage gear. She's wearing an orange bodysuit and tall boots. Her torso is strapped inside a box that looks like an old suitcase, her ankles are cuffed and attached, and she's muzzle gagged. A large sticker reading "FRAGILE" has been placed over her left eye

Keep your luggage securely stowed for extended travel 💙

A cartoon of two identical looking blue people wearing bondage gear. One is dressed like an angel and floating off the ground, wearing a loose white mini dress with wings and a halo. They're restrained with a blindfold, muzzle, padlocked in a set of metal cuffs around their wrists and ankles, and wearing a metal chastity bra belt. The other person is dressed like a devil, wearing a hot pink catsuit with pink heeled boots and horns on their forehead. They're restrained with a mesh muzzle, collar, body harness, cuffs around their thighs and ankles, and a ball-and-chain. The two of them are chained together at the ankle. A word balloon above the angel reads "?" while the devil, looking at the viewer with a toothy open-mouth smile, has a word balloon that reads "!".

your angle or yuor devil

Cartoon drawing of the same person in three different poses: squatting and shackled to a small bike rack, wearing office attire; standing, secured in a one-bar prison, with spreader bars attached to their hands and feet, wearing a harness ballgag and a simple red dress; and hopping forward, wearing a pink straitjacket, a muzzle, and straps securing their legs together. Picture has a pink color scheme

Same as previous, but with an orange color scheme

Sammy says "hi"! Can't decide if I like the pink or the orange better

A pixel art portrait of a cartoon person with blue skin, chin-length blue hair, wild pink-and-yellow eyes, and a toothy grin, set against a pink background. They're wearing a muzzle and a collar with tag on it that says "HONK"

Hi!! Sammy's the name, drawing cartoon bondage is my game