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

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27

How does it feel?

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45

coz I'm Hot

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64

Placement

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64

Which does he hope for?

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12

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

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29

The Wife Returns

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16

no more nudes for you

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63

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

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17

Better be a good boy

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39

Happy Caprice, happy life...

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20

pixles are your new porn

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21

Damn...

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63

Shopping with the keyholder

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210

I believe that she will make you beg for it!

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57

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

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19

Matrimonial bliss and a new life.

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15

With age comes assurance and heavier kinks.

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10

Trust, but verify.

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58

So small that even chastity leaves you with room..

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105

And stand up straight!

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11

Teased by them[GIF]

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116

Teaching her friend to expect male service.

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13

Word gets around

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94

A whole new side to your roommate

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138

Be careful what you say

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60

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

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55

sounds fair ...

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25

Harsh Numbing

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66

Mom extends your chastity

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35

Oops!

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43

Having no say in the matter is common these days.

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12

mother does you a favor

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70

five weeks

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28

The cage is much too big for the tiny cock!

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21

Is 2D against the rules?

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66

So stop asking

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71

All captions should be beta safe

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22

There will be loud moans and cries

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28

Beta marriage is the only kind you'll know.

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24

at least she's thoughtful

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63

good opportunity

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16

Hmm I don't believe it

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71

Great, now I'm horny!

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186

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

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41

Another lazy sunday

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74

The Cuckysitter Earns Her Keep.

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29

Poor chasty...

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34

Chastity creates a complete change in the dynamic.

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37

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

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16

Who Cums First

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348

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

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34

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

Simply awesome to be used like that.

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10

vacation pics

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34

Cyberpunk chastity slave (art and caption by me)

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52

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

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13

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

The lie that has launched a thousand female led relationships.

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98

Congratulations, you really pissed her off.

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117