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Chastity Fantasy: Caption 104b. He wasn't supposed to be up there tonight!

https://i.imgur.com/ZxDWoYW.jpg

User: wellhowaboutmaybe

Categories: keyholdercaptions

Your best friend

Three views

An offer too good to refuse

On the other hand, if you're not nice, it'll obviously be another story.

Is she using supplements?

A Numbers Game

Girlfriend is trying to understand

Would you let her into your life if it met a permanent sentence in chastity?

You should really be careful what you ask for...

Objects In Front Of You May Be Smaller Than They Appear

Cruise

Inspection

She wakes up horny and hungover

Will you do it?

A New Kind Of Fun

Asking for a loan

You'll learn.

What did you think I meant?

She has a goal, and your complaints won't stop her from achieving it.

I wonder if everyone will still be able to tell that your dick size is so small with

She knows how powerless you are.

It's what you deserve for upsetting her.

Mistletoe + Cameltoe

Good boys gets thighs

Better start working out!

If you think it's hard now, wait until she's kept you locked for a few weeks.

Escort Extortion

Things changed a bit ?

Pleasure for Pain

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