Best 5 Sissy Chastity Stories

Lily’s Mistake This story may not be suitable for all readers. This story contains CNC, pain-inflicting, and torture. This is a work of fantasy. The relationship depicted in this story is a consensual one. The

Lily’s Mistake

This story may not be suitable for all readers. This story contains CNC, pain-inflicting, and torture. This is a work of fantasy. The relationship depicted in this story is a consensual one. The relationship has clear and defined rules, limits, and safewords. This should not be acted out without serious discussion and consent.

The character of the owner/Lily’s owner/her owner is created to identify as whatever gender identity the reader wants so enjoy! 🙂

Lily is doing the dishes in the kitchen, as a good maid does, she tells herself. She does all of the chores every day. She knows her place.

She’s naked, of course, because she is not allowed to wear clothing in the house, except for her collar, a plug chosen daily by her owner, and her chastity device, which she is allowed to choose herself –a special treat for being a good puppy.

Lily’s owner enters the kitchen and takes a good, long look at her ass, plump, firm, and toned. Lily does her exercises in between her chores; she has to keep in shape if she wants to keep her owner. They grin sadistically.

Her owner grabs her hips lightly and starts to carefully grope Lily’s ass cheeks. She freezes instinctively, she knows that she is to let them do what they want and not interfere.

They pull their hand back and thwap! spank Lily hard. So hard it leaves a deep red handprint on her cheek. Lily is used to spankings, she makes no sound, just flinches slightly as it connects.

Her owner reaches around and grabs her nipples, twisting them. This is her owner’s favorite game: make Lily cry. The nipple torture does nothing but make her clitty twitch in her cage.

They reach around and slap her small, swollen, blue balls, and she tries her hardest not to make any sound. Her owner slaps them again, much harder, and she whimpers quietly.

They chuckle and bite Lily’s ear, whispering, “Bad pet, you know you’re not allowed to make any noise unless I tell you.” Lily starts to tear up and cry.

They throw her roughly to the floor, and she tries to crawl away but they grab her legs and pull her back in front of them.

Her owner positions her face down, ass up and starts spanking her hard, saying “who the fuck do you think you are, trying to crawl away?”

Lily knows what is coming and she silently pleads for mercy. Her owner slaps her already sore balls and continues spanking her until her ass is red as an apple.

Her owner rises up. They spit on her, and tell “you’d better not fucking move.”

They rip their top off and slowly unzip and slide their pants down. Their cock rises out of their pants, long, thick, and hard. They present it to Lily, making her take a good long look at every single inch of their cock.

They rip her plug out and immediately shove their cock all the way in Lily. She screams, they laugh; the scream only makes them hornier. They start pumping viciously on her sore, raw boipussy.

Lily begins crying now, she can tell they will last a long time, they’ve already brutally fucked her throat that day, and she’s sure they’ve made themself cum to prepare for this.

Her owner plans these things, everything they do is based on Lily’s actions throughout the day. Lily is just thankful she properly lubed her pussy this morning. She dreads the day she doesn’t remember.

They rail her roughly and brutally for what seems like forever, before they pull out and say, “Don’t you dare fucking move.” Lily obediently waits, face pressed against the cold, hard floor, and her throbbing, sore pussy in the air.

Lily doesn’t know how long she waits there before they come back.

Lily’s owner dropped a pillow on the floor before they made sure Lily could see they had a riding crop in their hand, and she whimpered out, “Please no..”

They smack Lily’s balls hard with the crop, making her jump. “You think you can talk back to me,” they yell.

“Get up,” her owner commands. Lily obeys, she doesn’t want the crop again. “You’re gonna ride my cock and tell me how good it feels.”

Lily hangs her head as her owner lies on their back on the floor. Her clitty leaks, and the drop connects her clitty to the floor.

“That’s fucking pathetic,” her owner laughs, “Get going slut.”

Lily squats down on wobbly, jelly legs and starts to position her owner’s cock at her puckered hole. She begins to lean back and sit down on the cock, inserting the head first, and slowly letting it inside of her

Riding cock was one of the few things Lily had to do for her owner that she liked. She got to control the speed somewhat and, even better, she could control the angle, allowing her to hit her sissy g spot just right. Since she is basically in permanent chastity, if there’s one thing Lily learned quickly, it was where her G-spot is located.

Lily tries to angle it just right, or at least as right as she could get without falling over. Her owner begins to grow impatient; every second spent adjusting is a second that Lily isn’t riding the way they want her. They bring the crop down on Lily’s chastity cage, knowing it won’t hurt really, but it will send a message.

Lily finally gets the angle and starts to bounce on the cock, prodding her G-spot with each stroke. She moans out.

“Good whore,” her owner chuckles, “I don’t hear you telling me yet.” Her owner taps the crop head gently on Lily’s thigh.

“It feels so good,” Lily half moans and half cries. She feels the pleasure, but it is bittersweet at best: her hole is sore and raw from her owner’s prior assault on it.

Then, it happens. The moment for which Lily had been waiting.

Sissygasm.

Her legs give out and she falls down on her owner’s cock. She tried to ride it as best as she could, but she could barely move.

She quivers and whimpers as her locked clitty oozes sissy cummies onto her balls and thigh. Ecstasy. Pure ecstasy.

Her owner slides their cock out of her hole amidst Lily’s sissygasm. They scoop some of her cummies off Lily’s thigh and jam their fingers into her mouth. Lily licks them clean, she is a good sissy after all.

Her bliss is short-lived.

Her owner grabs her throat and pushes her on her back before grabbing her knees and forcing the length of their cock into her pussy again. They start fucking her even harder than before.

They snack her balls and nipples more as they fuck her. “Who said you could cum?” Her owner holds her knees to her chest, using the leverage to force themself deeper inside of her.

The tears begin again. “You want to be bred slut,” her owner says as they pick up their pace.

“Yes,” Lily weakly responds between moans and tears.

“Say it like you mean it!”

“Yes, I want to be bred by your big cock!”

With that, her owner slaps hard against Lily, forcing their cock as deep as they can, and orgasm, grunting and groaning.

Her owner slips their cock out of Lily’s well fucked hole. She sighs, it’s over.

They come up next to her face and drop their cock on her lips. “Clean up your mess,” they command.

She takes their cock in her mouth and they force it down her throat, making her gag on it. She can taste their cum and her own anal juices on it.

They pull out and slap her playfully across the face. “Open.” Lily obeys. Her owner spits in her mouth. “You don’t swallow that until I’m gone.” And with that, they leave.

Lily doesn’t dare move until she stops hearing their steps.

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