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Chastity Fantasy: Caption 105. Maybe they'd best just toss a coin and get started?

User: wellhowaboutmaybe

Categories: keyholdercaptions, u_TheRopeIsForMyBoat

It's just three days [my first caption]

Choose your keyholder

She knows exactly what's going to happen next time.

They want to see me use it on you

Your embarrassment turned me on more than I expected

I did the math, and the safest answer is 19. But is "safe" the way to go?

Performance based release

Yes, obviously it was me that put that thing on your cock while you were sleeping...

That time of month

Are you scared?

Apparently your roommate is kinkier than you thought.

Blind Date in a cyberlock

Introducing your keyholder to your friends

Forgiveness

Locked after a long night of drinking

Thank you for volunteering to take part in our behavioural experiment...

You're in for a rough semester.

Chastity is just as fun as you thought. For her.

Masturbate while you still can...

No Arguments

Lucky you

April Fools

Lapdances at the best.

The pinnacle of modern medicine

Licking my lips in anticipation.

Who would you call?

Why would I?

Going to be a long summer

Don't break the rules.

Cum down

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