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I wish I had to make this choice.

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30

It sure didn't take much more convincing than that, to lock yourself up & give her the keys!

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122

Such a Pathetic Cuck!

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24

Uh oh, Her Sister is brutal

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32

Try really hard and maybe

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49

Over time, rituals become established, that's just part of it!

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30

Women always want to feel secure. Very secure.

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42

Haha you played yourself

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36

Your big sis will keep you straining all summer.

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93

Cucks must always be in chastity

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41

Its not like I care!

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36

Begging won't do much for my hubby.

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26

Way ahead of you, i am already wearing it.

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235

Deal?

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38

Did you try to hide it and got caught? Well, then you have to explain yourself.

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192

100%

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48

friends like you

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12

Just how I like it.

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12

Happy Weekends forever.

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26

A rhetorical question

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77

Would you give up your orgasms for her?

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195

It is better that my hubby is locked up

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60

That's five. One might expect punishment when the tongue gets tired.

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29

You are shy? No problem, your mistress will protect you!

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24

Inferior males are guilty with no attempt to prove innocence at The Institute.

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13

Is this a nightmare, or is it a dream?

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174

This is your sex now.

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47

We had a deal

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33

She has been working on Her Masters in Psychology on the topic of post-traumatic stress and how it is created.

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48

Oh my god, did you just came soft?

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80

I love to lock my hubby in his little cage!

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32

Lock it up forever for a look?

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14

Haha silly slave

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34

Haha pure torture

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58

He is only allowed to cum in the cage

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198

Betsy is usually successful in extending chastity. All of Her boys get "unruly."

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23

The Cage Is Staying On...

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65

She carefully chooses

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16

Will you give in to your stepdaughter?

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20

So are you?

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49

Sometimes the decision to cuckold is very easy!

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23

Training can be pretty strenuous. She will want to upsize that one to make certain he can take the real thing in any probable size.

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22

It's your job to do as she wants

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24

Keep your dick caged all weekend beta!

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30

She sometimes catches a nap while the cuckold struggles. It's a long day.

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46

Focus on those tits, and just think about cumming.

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23

Cleaning time!

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59

the gift

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45

This will be a memorable trip for the Wife, but also for him.

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16

The smaller the better

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28

Looks like you are going to be Her new pet.

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188

This is the moment of truth, what will you answer?

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28

Race Against the Clock by TangDraws

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56

Slave to your stepdaughter

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217

She doesn't mean any harm, she's just fulfilling your wishes!

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37

You knew beforehand what you were getting into!

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19

She wants you aching and so very desperate you'll do ANYTHING for her.

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28

Inmate Chastised

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12

A whole month of intense training, he'll be a changed "man."

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43

you're going to the chastity cage

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10