Chapters tagged chastity

A rubber sissy maid 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...

58 Likes

26,930 Views

Another Maid 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...

40 Likes

7,899 Views

Chosing to leave Jason (for now) 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...

23 Likes

4,483 Views

Marginally better 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...

10 Likes

314 Views

Training equipment! 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...

17 Likes

1,092 Views

Sissy's first blowjob 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...

18 Likes

1,093 Views

Yes, but my terms! 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...

21 Likes

1,120 Views

Needs an answer 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...

17 Likes

877 Views

Try your hardest 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...

14 Likes

870 Views

Joy and ownership? 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...

16 Likes

884 Views