Chapters tagged chastity

by Coy-toy

Chapter 3

Curious about rubber, and not seeing what the potential downside of this choice would be, you go to press the the rubber drone. As you reach out though, you slip and press under it by mistake, and too your horror you had selected the rubber maid. Before you can react or back out...

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 tinkerobi2

Chapter 18

Once again you work your tongue around your Masters cock, accepting this is your only choice and it is in your best interest to try your best. Using your tongue you wrap around his shaft, finding any of the leftover cum from your first blowjob. The gag prevented you from getting...

by tinkerobi2

Chapter 18

"I doubt you have had much experience in whats needed, so lets get you started!" The sissy proclaimed as they span you around and away from the mirror. You only nod and agree, finally slipping your hands from the cock cage and allow the sissy to walk you back towards the bed. "N...

by tinkerobi2

Chapter 19

You somewhat shake yourself enough to register how far down the rabbit hole you had gone, and how you were now dressed up and restrained more than your sissy assistant was when you started. How you must look in the real world actually made you laugh a little, then you felt a soft...

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 21

You feel him grabbing at your rubber covered head and push you away from his cock, "Sorry Sir, but I need an answer", you want to glare wrathfully at them, but the best you manage is a pleading look as you slowly look upwards towards they lustful eyes. "I..", is all you say befo...

by tinkerobi2

Chapter 22

You look between their grinning and lustful face, then back down the their dripping cock just inches from your face. You consider what you would want to hear from a sissy, how would they beg you in a state... the irony of the situation slipping from your mind. "Please...

by tinkerobi2

Chapter 23

"Such a and cage Sissy!", the sissy shouts with joy as they briefly jump at the edge of the bed, their cock slaps against your helpless face. "Lets get you ready!", then within moments they have strapped the gag around your face. "The blow job lips work great with your...

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 tinkerobi2

Chapter 25

As you mentally ready yourself for their cock, have to correct yourself, wanting to shave yourself bald, calling them master even to yourself. This wasn't where you aiming to be when you joined this session, but with every twitch from your caged cock more affirming thoughts of yo...

by tinkerobi2

Chapter 26

The first surprise had come at how quickly you had learnt how to breath while deep throating, you had been unsure if the game or VISS had any safety limits setup to prevent you being faced fucked or not. It even didn't seem right, in through the nose as the clock pull...

by tinkerobi2

Chapter 27

Restrained as you are and exhausted from your first blowjob, you could only continue to look forwards and between the legs of your Sissy Master. Their cock still hard even after what must have been an epic orgasm on their part, a large balloon of cum had formed at the end of thei...

by tinkerobi2

Chapter 28

And you tip your head back, was it because you wanted to? because your Sissy Master had told you to? or because this was the last part of that quest? Does it even matter at this point as there wasn't much of a choice regardless of the reason. "Now remember, Sissy's don't spit!",...

by tinkerobi2

Chapter 29

Its warm, thick and probably a lot less than it feels like, but the contents of the condom is now sitting at the back of your mouth and tongue. You are unsure if you can swallow whats now in your mouth with the gag in place without gagging, "Aww... poor sissy can swallow my cock,...

by Coy-toy

Chapter 5

You didn’t think there was a chance in hell you could win this game on insane difficulty, but you wanted to both challenge yourself, and find out what cumdrunk mode felt like. Knowing you were going to lose anyway, you designed the sluttiest character you could imagine. You deci...