Categories

SELECT COUNT(*) FROM gallery WHERE topic_category="keyholdercaptions"

More frustration

More frustration

May the odds be forever in your favour

May the odds be forever in your favour

My Keyholder Is A Green Lantern

My Keyholder Is A Green Lantern

Maybe they'll massage your balls until you squirt again!

Maybe they'll massage your balls until you squirt again!

Yeah...you get this a lot.

Yeah...you get this a lot.

Are you prepared to give up everything for her to be your key holder?

Are you prepared to give up everything for her to be your key holder?

She can't help but treat you like shit.

She can't help but treat you like shit.

A difference you only appreciate when you've been denied

A difference you only appreciate when you've been denied

Sisters humiliate you

Sisters humiliate you

She never rushes these procedures.

She never rushes these procedures.

Release Cancelled

Release Cancelled

That's my foot

That's my foot

Welcome home

Welcome home

complete control

complete control

Pavlov

These two things are connected...

These two things are connected...

Your girlfriend has...interesting friends.

Your girlfriend has...interesting friends.

It’s the only way

It’s the only way

Your quiet day.

Your quiet day.

Just so that you know 😄

Just so that you know 😄

If you ever wanna get out again, you better follow my demands 😈

If you ever wanna get out again, you better follow my demands 😈

Sister introduces you to your crush

Sister introduces you to your crush

Serve her guests

Serve her guests

Milked

In Ruins at the Edging Clinic

In Ruins at the Edging Clinic

Your Chastity Counsellor

Your Chastity Counsellor

You are going to become my new chastity slave!

You are going to become my new chastity slave!

It's so unfair! He always takes so long to give back your key!

It's so unfair! He always takes so long to give back your key!

The key was in my my suit case, and baggage claim said I would get a call when it was found.

The key was in my my suit case, and baggage claim said I would get a call when it was found.

I used to be almost 8 inches before I played with chastity 😅🥴

I used to be almost 8 inches before I played with chastity 😅🥴

Footjob during locktober

Footjob during locktober

Keyholder Joke

Keyholder Joke

What if you never stop?

What if you never stop?

Time for milking !

Time for milking !

She forgot it on purpose

She forgot it on purpose

A good breakfast to start the day out right.

A good breakfast to start the day out right.

As Close As He'll Ever Come

As Close As He'll Ever Come

Everyone knows I'm in chastity and she has the keys

Everyone knows I'm in chastity and she has the keys

Yes please

Teachers plaything

Teachers plaything

OC - The teddy could be you, but I lost the key to your lock. (Original Picture - Turning my keyholder fantasies into captions.)

OC - The teddy could be you, but I lost the key to your lock. (Original Picture - Turning my keyholder fantasies into captions.)

She has a point

She has a point

Yes, that's why

Yes, that's why

Feet

Aww, Is It Hurting Already?

Aww, Is It Hurting Already?

little reminder.. 👅

little reminder.. 👅

Next year?

What have you been hiding?

What have you been hiding?

Canceled

Changing room dare

Changing room dare

A very special weekend indeed

A very special weekend indeed

Femdom Chastity Propaganda!

Femdom Chastity Propaganda!

Found out

All you can eat in the coming days

All you can eat in the coming days

Smaller and smaller

Smaller and smaller

An intimate little get together

An intimate little get together

Sissy, crossdressing, pegging

Sissy, crossdressing, pegging

Punishments or incentives

Punishments or incentives

I'll bet She goes on all of Her Daughter's jobs.

I'll bet She goes on all of Her Daughter's jobs.

Can I please cum mistress?

Can I please cum mistress?

MIL's obedient bitch

MIL's obedient bitch

Try not to embarrass yourself!

Try not to embarrass yourself!

How Long Can You Hold Your Breath?

How Long Can You Hold Your Breath?

The Hearing

The Hearing

cucky, you are mine to play with..

cucky, you are mine to play with..

You know you're getting in that car....

You know you're getting in that car....

Normal size

Normal size

Holiday humiliation

Holiday humiliation

Start serving me bitch 😈

Start serving me bitch 😈

Perfect memory

Perfect memory

Give her what she wants

Give her what she wants

Cumming like a girl.

Cumming like a girl.

Pals

No trouble at all.

No trouble at all.

No gag reflex and no mercy

No gag reflex and no mercy

A very special weekend indeed

A very special weekend indeed

Frequency chart for your future orgasms

Frequency chart for your future orgasms

At least you get to watch still!

At least you get to watch still!

The month begins

The month begins

Squeeze those little useless balls.

Squeeze those little useless balls.

Just FYI upfront 🤓

Just FYI upfront 🤓

I guess my rules are not that hard huh? 😬

I guess my rules are not that hard huh? 😬

Moms pool party

Moms pool party

Do you mind if my ex hangs on to your keys for a bit? He’s only leaving the country for like two months.

Do you mind if my ex hangs on to your keys for a bit? He’s only leaving the country for like two months.

You do not come to bed like that

You do not come to bed like that

Shrinking your dick in chastity

Shrinking your dick in chastity

New cage

Teachers cuck

Teachers cuck

Don’t embarrass yourself anymore. Let her lock it up

Don’t embarrass yourself anymore. Let her lock it up

What would you reply and do boys?

What would you reply and do boys?

Incoming torment from step-sis

Incoming torment from step-sis

awww sorry white boy!

awww sorry white boy!

That sneaky loophole

That sneaky loophole

You maybe hoped for a better start

You maybe hoped for a better start

Serving the Lady

Serving the Lady

When your key holder decides it’s time to tell her sister…

When your key holder decides it’s time to tell her sister…

Kneel and beg...

Kneel and beg...

Spoiler: she won't...

Spoiler: she won't...

You're never allowed out of your cage anymore!

You're never allowed out of your cage anymore!

Icky