Categories

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

Could be an expensive time

Could be an expensive time

Take it all in

Take it all in

Get me the strapon baby 😈

Get me the strapon baby 😈

Down Here

Know Thyself

Know Thyself

Anyone else also feel cum denial, ruins and cuckolding suits the chastity lifestyle?

Anyone else also feel cum denial, ruins and cuckolding suits the chastity lifestyle?

When she gives you a choice that doesn't really feel like a choice

When she gives you a choice that doesn't really feel like a choice

Making you close the lock.

Making you close the lock.

Reorientation

Reorientation

You wanna go to the beach? The conditions are easy 🤫

You wanna go to the beach? The conditions are easy 🤫

She ignored you completely

She ignored you completely

Not all men are created equal.

Not all men are created equal.

Tinder dom dates (part 5 )

Tinder dom dates (part 5 )

You Belong Beneath Her

You Belong Beneath Her

She really doesn't care

She really doesn't care

Dont worry about her in Locktober

Dont worry about her in Locktober

Even the hung studs get locked up 🔒

Even the hung studs get locked up 🔒

I'm in charge now

I'm in charge now

Finally, some relief—maybe?

Finally, some relief—maybe?

I know you're having a hard time in chastity, but I can't just unlock you when you ask...

I know you're having a hard time in chastity, but I can't just unlock you when you ask...

She’s happy

She’s happy

It would be so obvious 😬

It would be so obvious 😬

Nothing else needed to say huh? 😈

Nothing else needed to say huh? 😈

I will be putting these on you, and I have a surprise...

I will be putting these on you, and I have a surprise...

Deal is a deal

Deal is a deal

More than roommates

More than roommates

I hope you will thank him for taking care of your wife

I hope you will thank him for taking care of your wife

If only they knew

If only they knew

Algorithm Chastity RPG • HOT HORNY MILFS IN YOUR AREA (you need a D6 🎲, other rules in comments)

Algorithm Chastity RPG • HOT HORNY MILFS IN YOUR AREA (you need a D6 🎲, other rules in comments)

Friend Zoned

Friend Zoned

Give me the keys, I won't lie 😏

Give me the keys, I won't lie 😏

Hope you enjoyed your night with her

Hope you enjoyed your night with her

Entertain your Goddess

Entertain your Goddess

She loves nipple play and knows how to get what she needs

She loves nipple play and knows how to get what she needs

Anything for that pawg wife.

Anything for that pawg wife.

The good boy WANT to stay locked up, just so you know 🤓

The good boy WANT to stay locked up, just so you know 🤓

Slave

When she gives you a choice that doesn't really feel like a choice

When she gives you a choice that doesn't really feel like a choice

Locked up and good to go...

Locked up and good to go...

I don't know any better way to start the day 😏

I don't know any better way to start the day 😏

Unfulfilled yearnings

Unfulfilled yearnings

Definitely a keeper

Definitely a keeper

Is it a sacrifice you’re prepared to make?

Is it a sacrifice you’re prepared to make?

She's so pretty but so cruel. You don't deserve her.

She's so pretty but so cruel. You don't deserve her.

Heaven

Your wife knows best!

Your wife knows best!

I gave you a chance

I gave you a chance

A new cage

Handsome Boyfriend

Handsome Boyfriend

A company of women. This was inspired by a story by the same name, on Literotica. (Feet, pussy, oral, public humiliation)

A company of women. This was inspired by a story by the same name, on Literotica. (Feet, pussy, oral, public humiliation)

Teachers plaything

Teachers plaything

It was worth it.

It was worth it.

How late will this party be going?

How late will this party be going?

The Winner’s Reward Choice

The Winner’s Reward Choice

Local Authorities

Local Authorities

Good luck with that 🤭

Good luck with that 🤭

Her plans for you are unspeakable

Her plans for you are unspeakable

Not for at least a month, anyway...😍 You can't lie to those eyes

Not for at least a month, anyway...😍 You can't lie to those eyes

Serving the Lady

Serving the Lady

Armpits

Dealing With Hyperbole

Dealing With Hyperbole

sudden orgasm

sudden orgasm

My chastity slave made this for me

My chastity slave made this for me

Dirty feet

Like it's never crossed your mind

Like it's never crossed your mind

I'm ready Goddess

I'm ready Goddess

How else would I secure these things? 😈

How else would I secure these things? 😈

It's hard to explain, really

It's hard to explain, really

She holds the keys, and makes the rules

She holds the keys, and makes the rules

What if I just...?

What if I just...?

You will stay locked in your cage Until..

You will stay locked in your cage Until..

Your little plan didn't exactly work out.

Your little plan didn't exactly work out.

I'm not so easy to escape

I'm not so easy to escape

You still get to watch porn

You still get to watch porn

I wonder if its a Trick or another treat?

I wonder if its a Trick or another treat?

His only future

His only future

Choose your Keyholder

Choose your Keyholder

Still At It

Still At It

Holidays

last chance

last chance

After 2 weeks panty teasing, my stubborn numb cock dribbled salty cum down the shaft and over my big blue balls.

After 2 weeks panty teasing, my stubborn numb cock dribbled salty cum down the shaft and over my big blue balls.

You have GOT to start being more specific.

You have GOT to start being more specific.

Fitness Chastity

Fitness Chastity

Who's pleasure is more important?

Who's pleasure is more important?

Because Reasons

Because Reasons

no stamina

That's what she said last week.

That's what she said last week.

No release for my tiny shrimpy! Mommy knows!!

No release for my tiny shrimpy! Mommy knows!!

Betrayed by your lack of self control.

Betrayed by your lack of self control.

Visualizing Things

Visualizing Things

She hunts the hunters.

She hunts the hunters.

Convincing the wife.

Convincing the wife.

I'm often asked to explain to her visitors how much i enjoy the cage, and how my need to be locked up for longer is for my own good.

I'm often asked to explain to her visitors how much i enjoy the cage, and how my need to be locked up for longer is for my own good.

I've been locked at Electric Forest 🥴 what an adventure

I've been locked at Electric Forest 🥴 what an adventure

😩 blissful torture

😩 blissful torture

The bride

As Close As He'll Ever Come

As Close As He'll Ever Come

Beach Milf want to be your new keyholder

Beach Milf want to be your new keyholder

So close