Chapters tagged sissy

by Darthnova1313

Chapter 16

Not hearing a reply in time another maid enters the room clearly read to clean it. They are pulling a cart of cleaning supplies with feather duster, gloves, a small vacuum, several bottles of heavy cleaner, and a large amount of used sex toy. Some of the sex toy still dripping va...

by Darthnova1313

Chapter 18

It is a hard decision but in the end you chose to let Jason sleep. Not willing to risk your deal being altered more you walk with the Maid leaving the room. Before you get far it hits you, they haven't given their name. Swiftly grabbing the maid's hand to stop them you ask "I kno...

by Coy-toy

Chapter 14

The maid pulls on your leash, having you follow the sissy out of the room and through the mansion. “There is a specific place for all our slutty little puppies after all, though some may prefer to use such a cute little bitch like you fufu.” He laughs as you are pulled along. You...

by Micem

Chapter 11

Maybe it's because you are simply too mentally weak to deny this sissy what he wants when he seductively asks, but you agree. The moment you whisper "ok, do it" through his kisses he giggles with a hit you glee. He keeps kissing you as he uses both hand to work your shaft. Someho...

by Micem

Chapter 12

"You look so cute with closed caged penises, just like a real sissy." He says. He resumes passionately kissing you, his free cock hard and rubbing against your tightly caged cock. You let out a long, low, and extremely horny moan, before the sissy suddenly breaks off the kiss to...

by Micem

Chapter 13

He giggles before saying, “Of course, doesn't your ass, hungry for my cock, confirm this? I don’t know why your mother gave you such a shitty male name, but now is a good day to change that.” His mocking words excited me and my penis tried to become hard again, but the plastic c...

by Micem

Chapter 14

"I... I am a sissy! I am an obedient sissy who loves when my maid dominates me and fucks me in the ass!" He laughed. "Please... Please fuck me with your cock!" He smirks at your predicament. "I don't think you realize how weak you are. I can make you my sissy bitch and make yo...

by Micem

Chapter 16

"You look so pretty in this outfit. Maybe you would even be somebody little sex toy tonight! Do you think you're man enough to handle the strap-on?" "You're... You're not going to make me go out dressed like this?" Hi gives you a smirk, "Oh, you look very cute. You are so gentl...

by tinkerobi2

Chapter 20

The sissy's cock was only in your mouth for a moment, they hadn't tried to push deeper or even to start thrusting, they just pulled you right off it. "Sir wants an early release option, So, here is the deal!" the sissy mocked! They tip you back slightly so you can now see their...

by tinkerobi2

Chapter 24

You hated to admit it, but you were sure you were starting to get used to the constant squeezing of the cage trapping your cock, what was once a painful misjudgement on your part was becoming an unwelcome reminder of your position.. its crushing reminder less painful as you accep...

by Coy-toy

Chapter 8

You feel embarrassed that the sissy maid kneeling before you would laugh at you. You didn’t choose panties, the stupid game did, right? Blushing and frustrated, you decide to cover your embarrassment by punishing the AI. “Oh you think that’s funny? What’s your name maid?” You as...

by Coy-toy

Chapter 9

You are in heaven as the sissy keeps sloppily kissing and sucking up your shaft. You let out a surprised moan when his one of his fingers slides past your ring and into your clinching hole. You might have said something, but at that same moment he gobbled your cock in one fluid m...

by Coy-toy

Chapter 10

He noticed you approach the edge, and while keeping two fingers in you he stops gagging on your cock, slyfully licking the side now as he asks “is ‘sir’ close? Would he like to cum?” Barely surviving the pleasure, you simply whimper “yes I wanna cum.” “You know, I don’t...

by Sparkee23

Chapter 7

You wonder what type of present the game would have in store, and curiosity ends up winning out. You look at the sissy, saying “ok maid, so me what present you’ve gotten for me. If it’s good I may even reward you!” The sissy smiles widely, grabs your hand and leads the way. His s...

by Coy-toy

Chapter 8

“We have been to serve your family long enough to learn some interesting things, such as the male heir was a closet sissy!” He gave a look to one of the maids behind you, who pulled down your tight jeans revealing your bubble butt in a pair of bright red satin panties. All...

by Coy-toy

Chapter 6

Though you are curious on just how far you can really go with the staff, you chose this game for the main story, so main story you will complete. Leaning into your role, you tell the maid “I’m sure my mother is not known for her patience. Let us not leave her waiting.” The maid...

by Coy-toy

Chapter 6

Your curiosity peaks with the potential submissive roles, and after reaching out and pressing the words a new list replaces the old. Submissive Sand Box: - House sissy maid: fulfill daily roles of a regular maid. Chastity and bondage is a normal part of maid attire, and any may...

by Coy-toy

Chapter 7

It sound painful, horrible, and draining... but that only makes you more and more curious. You can’t help but grin and blush as you reach forward, pressing the sissy cow words. Everything fades around you, quickly replaced by a large barn interior. There is moans and groans all a...

by Onyxdragon100

Chapter 5

You gulped, as you got to work. You picked a simple femboy appearance, with blonde twin tails with pink tie and bright blue eyes. You choose a schoolgirl outfit. Which was a white blouse, with a short red tie. A short red and black pleated skirt, with pink thigh high stockings an...

by Coy-toy

Chapter 5

You decide to dress like a cute goth girl you knew from school did. You chose black and white striped knee high socks and arm warmers, a black skirt with a sliver metal chain belt, and a black tank top with a low cut. You went with black bangs and shoulder length hair that went w...