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Chastity Fantasy: Caption 75. Won't you let me help you? I'm worried!

https://i.imgur.com/7oJylLh.jpg

User: wellhowaboutmaybe

Categories: keyholdercaptions

Make Your Choice

Try to look happy, it's going to be a long year.

Are you the guy asking if some keys were handed into lost and found?

One-time deal

So that's why you have so many notifications.

You're sure you're so desperate that you can't wait for your scheduled release next

Formal request to open cage

So mean of your gf to make that wager!

New Roommate

"Anything" is a dangerous word to use around her.

Just another cage

A key is such a fragile, meltable thing...

She loves how dedicated you are.

Don't give her any attitude.

I just found out about this /r/! ? Let's have some fun boys! ? (Yes this is me in

I guess we start a 'little' earlier this year ?

Halloween party

You know what you're signing up for, right?

Don't talk back.

How many more will you have to endure?

Rachel Cook accepted your bet, time to hold up your end of the bargain.

I wouldn't be able to resist if I'm honest.

Sudden Showers (Patreon 3/7/21) [chastity][gentle femdom][co-worker]

There are some perks to buying your toys in person rather than online.

Released with no release.

If you are good

Foreign Key Exchange

Either desperation or good training ?

Denial by Committee

You know you're in trouble.

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