Jizz

Keyholdercaptions pics

How long is your chastity duration

How long is your chastity duration

keyholdercaptions

Waiting until midnight

Waiting until midnight

keyholdercaptions

A lot can be said with only a facial expression

A lot can be said with only a facial expression

keyholdercaptions

Overslept

Overslept

keyholdercaptions

She shows your cage off to a friend

She shows your cage off to a friend

keyholdercaptions

No Way

No Way

keyholdercaptions

Convincing her friend

Convincing her friend

keyholdercaptions

Thus you will learn to control yourself

Thus you will learn to control yourself

keyholdercaptions

What he wants and deserves

What he wants and deserves

keyholdercaptions

Looking for love at work

Looking for love at work

keyholdercaptions

Don't you have anything you want to ask of her?

Don't you have anything you want to ask of her?

keyholdercaptions

When you've been married for a while...

When you've been married for a while...

keyholdercaptions

Experimenting Methods

Experimenting Methods

keyholdercaptions

New Toy

New Toy

keyholdercaptions

Catch me if you can

Catch me if you can

keyholdercaptions

You have a decision to make.

You have a decision to make.

keyholdercaptions

Dealing with two keyholders will make things interesting.

Dealing with two keyholders will make things interesting.

keyholdercaptions

Chastity 101

Chastity 101

keyholdercaptions

She didn't plan to use you the way you expected

She didn't plan to use you the way you expected

keyholdercaptions

Reuniting with a girl from middle school

Reuniting with a girl from middle school

keyholdercaptions

One for the scrapbook ?

One for the scrapbook ?

keyholdercaptions

What did you get her that could possibly be better than keeping you locked another

What did you get her that could possibly be better than keeping you locked another year?

keyholdercaptions

Every couple should do regular trust exercises

Every couple should do regular trust exercises

keyholdercaptions

Blurple

Blurple

keyholdercaptions

More teasing is needed

More teasing is needed

keyholdercaptions

She needs help for a lost key

She needs help for a lost key

keyholdercaptions

Dating in the 21st century

Dating in the 21st century

keyholdercaptions

Big cock = Big ego. Big cock + cage = ...

Big cock = Big ego. Big cock + cage = ...

keyholdercaptions

She takes charge pt11

She takes charge pt11

keyholdercaptions

Good job! You've earned yourself a reward! :)

Good job! You've earned yourself a reward! :)

keyholdercaptions

??

??

keyholdercaptions

Check-up

Check-up

keyholdercaptions

She knows exactly how to use the carrot

She knows exactly how to use the carrot

keyholdercaptions

Excited about Vacation

Excited about Vacation

keyholdercaptions

Brave soul

Brave soul

keyholdercaptions

A new owner 7 months into chastity

A new owner 7 months into chastity

keyholdercaptions

Would you be able to control yourself?

Would you be able to control yourself?

keyholdercaptions

Not cute

Not cute

keyholdercaptions

It will be worth it, right?

It will be worth it, right?

keyholdercaptions

Summer Sleeping

Summer Sleeping

keyholdercaptions

Patience

Patience

keyholdercaptions

We will work together

We will work together

keyholdercaptions

Hopefully she'll teach him well

Hopefully she'll teach him well

keyholdercaptions

That Damn Dildo

That Damn Dildo

keyholdercaptions

It's kinda sweet when you get my demands in the wrong way.. ? Just to clarify..

It's kinda sweet when you get my demands in the wrong way.. ? Just to clarify..

keyholdercaptions

Your wife really knows how to commit to a role.

Your wife really knows how to commit to a role.

keyholdercaptions

Monthly cleaning

Monthly cleaning

keyholdercaptions

Nudist island

Nudist island

keyholdercaptions

Your date isn't looking for a boyfriend

Your date isn't looking for a boyfriend

keyholdercaptions

So close honey... Don't you miss the feeling of my lips wrapped around your cock?

So close honey... Don't you miss the feeling of my lips wrapped around your cock?

keyholdercaptions

You have a fundamental misunderstanding of what she's going to do to you.

You have a fundamental misunderstanding of what she's going to do to you.

keyholdercaptions

Nuzzling her

Nuzzling her

keyholdercaptions

It's like magic...

It's like magic...

keyholdercaptions

Throbtastic

Throbtastic

keyholdercaptions

35 Strokes

35 Strokes

keyholdercaptions

Making a caption for every 12h of my chastity sentence 6/16

Making a caption for every 12h of my chastity sentence 6/16

keyholdercaptions

Valkyrae tries a new, chat-integrated chastity program on her stream.

Valkyrae tries a new, chat-integrated chastity program on her stream.

keyholdercaptions

Caged Engagement

Caged Engagement

keyholdercaptions

Oh, how I love playing with you.. ?

Oh, how I love playing with you.. ?

keyholdercaptions

Swollen balls are a common 'side effect' ?

Swollen balls are a common 'side effect' ?

keyholdercaptions