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Keyholdercaptions

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A keyholder challenges herself on release day
Seems like she might be into it.
Helping You Reach Your Goals
Try to look happy, it's going to be a long year.
Was it worth it?
One-time deal
Size queen
Should have picked a better hiding place.
Compromise is a wonderful thing!
You were right about the amount but not the distribution of enjoyment
Penis Trap
Role reversal is fun! Even if it's only pretend.
So mean of your gf to make that wager!
She's going to make this take hours.
Your roommate is pretty devious.
Self control has never been your strong point.
New Roommate
"Anything" is a dangerous word to use around her.
Click the lock and you've lost all bargaining power.
A cruel game
Just another cage
A key is such a fragile, meltable thing...
Another half inch and you might have something worthwhile...
Fingers crossed
I shouldn't have snooped but I'm so glad I did
You don't like the evil glint in her eye.
Why is she so mean to you?
Will you? ??
Need a bib
Your wife is becoming a bit of a size queen.
What a perfect solution.
She loves how dedicated you are.
Your names don't even start with the same letter!
New to keyholding
Made to stay soft
She wants to keep things nice and clean.
Air hostess, I like the way you undress
Different rules for betas.
Your wife can torment you in her sleep. Literally.
I guess we start a 'little' earlier this year ?
Halloween party
Dinner date
She doesn't want to hurt you.
You know what you're signing up for, right?
Bet your Balls
right into her trap
Photo Op
How many more will you have to endure?
Making a caption for every 12h of my chastity sentence 7/16
There are some perks to buying your toys in person rather than online.
If you are good
You've got a lot of learning to do.
Foreign Key Exchange
Release Anxiety
Denial by Committee
You were hoping for a release, but she had other plans.
You know you're in trouble.

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