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Harsh Numbing

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66

A whole new side to your roommate

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138

There will be loud moans and cries

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28

Shopping with the keyholder

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210

Hmm I don't believe it

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71

Another few months, and your balls will be just how she wants them... Hopefully.

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55

Great, now I'm horny!

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186

Trust, but verify.

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58

coz I'm Hot

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64

I believe that she will make you beg for it!

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57

Therefore, check beforehand how the rules are, otherwise it can quickly become a very long stay in the chastity cage!

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33

Beta marriage is the only kind you'll know.

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24

Happy Caprice, happy life...

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20

Who Cums First

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348

Poor chasty...

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34

Damn...

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63

The cage is much too big for the tiny cock!

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21

Placement

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64

Word gets around

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94

pixles are your new porn

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21

Better be a good boy

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39

Teased by them[GIF]

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116

She is sure you won't be back home to wait up for Her tonight.

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13

Mom extends your chastity

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35

sounds fair ...

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25

You're let out of chastity AND allowed to cum AND allowed to lick her perfect soles... Win-win-win, right?!

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73

So stop asking

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71

Cyberpunk chastity slave (art and caption by me)

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52

Another lazy sunday

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74

Chastity creates a complete change in the dynamic.

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37

at least she's thoughtful

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63

good opportunity

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16

Congratulations, you really pissed her off.

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117

The Wife Returns

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16

If she asks what it's for, you can explain

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34

And stand up straight!

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11

Teaching her friend to expect male service.

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13

Matrimonial bliss and a new life.

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15

Beta cucks don't need to have the caged removed for their yearly milking!

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16

Which does he hope for?

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12

Oops!

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43

I'm learning a lot here... and so is he!

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29

Keyholders don't always have it easy either, often you have to pick your prey carefully

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17

five weeks

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28

Simply awesome to be used like that.

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10

The lie that has launched a thousand female led relationships.

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98

The Cuckysitter Earns Her Keep.

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29

no more nudes for you

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63

Is 2D against the rules?

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66

With age comes assurance and heavier kinks.

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10

She has been doing this for a long time. She is an expert.

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27

All captions should be beta safe

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22

mother does you a favor

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70

Taking a seat after a workout is good for a cool-down

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19

So small that even chastity leaves you with room..

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105

How does it feel?

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45

Whats better then keyholder captions? Censored keyholder captions!!!

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41

vacation pics

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34

Having no say in the matter is common these days.

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12

Be careful what you say

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60