8 XXX : keyholdercaptions

Acquiring herself two chastity slaves for the price of one

imgur.com category @NecessaryConfection

Honeymoon Choices

imgur.com category @xChangeFan

Seven Stages of Chastity

imgur.com category @Kalergian

Pretty misleading of your roommates. But they have the key.

imgur.com category @[deleted]

Seems like she might be into it.

imgur.com category @prettybadhorse

Do you accept the terms?

imgur.com category @[deleted]

Chastity sentence, in gif form!

gfycat.com category @Cashewnoten

It's just three days [my first caption]

imgur.com category @knot2nice

The polylesdom dream

imgur.com category @NecessaryConfection

Did he really make it

gfycat.com category @qalazar

She's willing to keep your chastity a secret, but everything has a price.

imgur.com category @prettybadhorse

Trying to earn her release

imgur.com category @xChangeFan

Dream experiment

imgur.com category @SpikesandAsians

Choice of Wares

imgur.com category @SpikesandAsians

Bet between friends

imgur.com category @chant9

Was it worth it?

imgur.com category @kinky_sex_enthusiast

Helping You Reach Your Goals

imgur.com category @AmpleWang

A keyholder challenges herself on release day

imgur.com category @castempress

A Cruel Game

imgur.com category @kinky_sex_enthusiast

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

imgur.com category @gr0undstone

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

imgur.com category @chant9

Make Your Choice

imgur.com category @Kalergi_

Preparing for his first full day in chastity (gif)

gfycat.com category @xChangeFan

Choosing your chastity sentence [1/2]

imgur.com category @NecessaryConfection

Smirking

imgur.com category @Anti_Wil

Birthday treat

imgur.com category @NecessaryConfection

But when she takes it off, the urge disappears.

imgur.com category @TotalLambdaUser

Of course, just the cage is never enough (/u/liz_103)

imgur.com category @NecessaryConfection

You're the guy that let me lock up his cock at that house party.

imgur.com category @chant9

Release days have become quite humiliating.

imgur.com category @[deleted]

She's letting you choose your reward

imgur.com category @xChangeFan

It's what you deserve

imgur.com category @Iamonefatman

She's not playing fair

imgur.com category @unusual_dialogue

I know that we made a detailed agreement, but...

imgur.com category @chant9

Why leave them on the keyring if you didn't want me to claim them?

imgur.com category @chant9

You should probably start watching what you say.

imgur.com category @prettybadhorse

Surgery complications

imgur.com category @SpikesandAsians

Don't worry about the keys, you trust me don't you?

imgur.com category @chant9

Minx

imgur.com category @SpikesandAsians

College rules

imgur.com category @chant9

They want to see me use it on you

imgur.com category @chant9

Losing Hope

imgur.com category @LockedDragon

Choose your keyholder

imgur.com category @Kalergi_

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

imgur.com category @FailedTheReCaptcha

OMG

imgur.com category @Anti_Wil

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

imgur.com category @gr0undstone

Your embarrassment turned me on more than I expected

imgur.com category @chant9

Long-distance girlfriend reconsidering her plan

imgur.com category @xChangeFan

As Fate Would Have It...

imgur.com category @SpikesandAsians

If you take things too far, she'll lock you up for a looooong time.

imgur.com category @[deleted]