Hey big bro, I want to hear you admit to

Hey big bro, I want to hear you admit to me what the keys are for.

You know the rule (OC)

You know the rule (OC)

Raw Deal

Raw Deal

Time to get serious

Time to get serious

We try your chastity thing (OC)

We try your chastity thing (OC)

She doesn't care about being fair

She doesn't care about being fair

I almost have you where I want you

I almost have you where I want you

I might have made a mistake...

I might have made a mistake...

I spoke to your sister today at school because

I spoke to your sister today at school because I was planning on asking you out.

Your embarrassment turned me on more than

Your embarrassment turned me on more than I expected

Special birthday present for a friend

Special birthday present for a friend

Why leave them on the keyring if you didn't

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

Don't be so selfish

Don't be so selfish

Are you the guy asking if some keys were

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

I hear my sister still hasn't let you out

I hear my sister still hasn't let you out of the chastity cage.

5k bet, no max limit, no going back

5k bet, no max limit, no going back

Stay still, let me send my friend a pic of

Stay still, let me send my friend a pic of your current cage.

Evil Cuckolding Wife

Evil Cuckolding Wife

Cuckolding Girlfriend

Cuckolding Girlfriend

Sexy tease and denial expert

Sexy tease and denial expert

Chastity-Enforcing Cocktease

Chastity-Enforcing Cocktease

Cheating Girlfriend Bends the Rules

Cheating Girlfriend Bends the Rules

Teasing and denying is hard work!

Teasing and denying is hard work!

Freshly Cleaned Titnosis

Freshly Cleaned Titnosis

Cuckolding bitch works the glory hole

Cuckolding bitch works the glory hole

Cross post from r/xxxcaptions. Let's get

Cross post from r/xxxcaptions. Let's get this subreddit going again!

Evaluation

Evaluation

Come Along (x-post from /r/keyholdercaptions)

Come Along (x-post from /r/keyholdercaptions)

down on your knees

down on your knees

Go on honey, I know you want it...

Go on honey, I know you want it...

Suck and fuck.

Suck and fuck.

imagine all the cum they unloaded

imagine all the cum they unloaded

After the Sale

After the Sale

So Much Cuter (x-post from /r/keyholdercaptions)

So Much Cuter (x-post from /r/keyholdercaptions)

Male Slave Auction

Male Slave Auction

The Jungle Cougar

The Jungle Cougar

thank you for popping down to see us in human

thank you for popping down to see us in human resources

Fairness

Fairness

it’s gross and you still can’t help lapping

it’s gross and you still can’t help lapping it up. in your mouth, drinks, off my shoe... I revel in ruining the small luxuries for you, reducing you to the pathetically desperate groveling worm you are. and you love it. love me for breaking you down so sm

I think you need to be punished!

I think you need to be punished!

"Good luck getting rid of that boner" (SPH,

Sister (x-post from /r/keyholdercaptions)

Sister (x-post from /r/keyholdercaptions)

Breaking In The Virgin

Breaking In The Virgin

Benign neglect

Benign neglect

Until I Say (x-post from /r/keyholdercaptions)

Until I Say (x-post from /r/keyholdercaptions)

Birthday Present (x-post from /r/Sissyperfection)

Birthday Present (x-post from /r/Sissyperfection)

"OMG is that seriously as big as it goes?"

Taming Him

Taming Him

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