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Your girlfriend has a friend over to play with

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109

You look forward to your birthday because you know youll finally get released. This year your desperation got the better of you... and your girlfriend is not the forgiving kind....

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99

First caption (not me in pic)

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34

Let's play?

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27

It appears that your Wife's Girlfriend had designs on you all along. Life-changing designs on you.

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39

Hope you're a quick study. And you like the taste of ass.

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19

Goon marathon

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50

you will finish locktober for them

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16

Locktober is over when she says it is.

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31

I'm tempted

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32

be honest.. did you see the pixels?..

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16

There, all nice and put away in a safe place. A safe place you will never experience again because everyone knows.

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28

Did mommy give you permission?

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She can get you to do just about anything for a taste of her ass.

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21

not a nightmare

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47

Ass-slave conditioning.

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94

Would you rather? Option A or B?

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61

Now why would I do such a thing?

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60

It's simple, Really.

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23

Some Psychologists say that negative reinforcement can be more effective than positive reinforcement.

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What a thoughtful keyholder!

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30

Her friends love bullying you.

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15

She's going to have so much fun with you.

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34

So sad and pathetic...

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Your keyholder is very easily distracted.

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75

You asked your friend to hold your keys for locktober

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107

Yes dear. I hope your friends don't laugh at me next time I see them

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67

Do you see chastity as a sexual meditation?

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74

thank you dear

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Getting the entire list done seems like a requirement, not a request. Perhaps, if you do, She'll bring you home a nice, creamy dessert.

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Your honeymoon isnt going as planned...

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71

All day. After several hours you'll be utterly soaked, which will provide Her with more lubrication. And it is very hard to breathe through that.

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27

Better then any release could have been

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34

Dove Cameron steals your promotion

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37

October is Locktober for you

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62

Tools for the month

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68

No hard feelings

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59

Goth GF

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284

Remember...

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64

Of COURSE you can lick it!

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167

He asked for it. Soon you will, too.

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15

Cruel girlfriend Marya

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154

Servitude is the only logical option for weak beta men..

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138

In the comments you will find a continuation

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168

Amouranth loves that you can work from home

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18

DECORATING FOR THE HOLIDAY [Darkest-Muses]

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47

Maybe

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51

What am I going to do with you?

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108

Show more enthusiasm!

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17

A New World Femdon Society

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25

Rita Ora extends your chastity sentence

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41

It's just the right thing for a beta like you! Chastity for you, big cock for me

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36

So dumb, so Desperate.

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53

New University Rules

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122

Truly a shame...

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33

Obviously, Her orgasms are much more important and valuable than yours.

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37

365 days to go

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15

Complaining is unacceptable behavior.

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64

How lucky you are to get to worship Me.

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29

I love teasing you while your in chasity

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20