8 XXX : keyholdercaptions xxx pictures

New Pyjamas

imgur.com category @SpikesandAsians

Choose your keyholder (Gentle to Moderate/Heavy)

imgur.com category @HentaiChastity

She knows exactly what she's doing.

imgur.com category @gr0undstone

A perfect release day, with some strings attached

imgur.com category @[deleted]

Conditioning a man to love his agony (/u/realankri)

imgur.com category @NecessaryConfection

Your new reality.

imgur.com category @jugstrago

Look baby, no hands!

imgur.com category @SpikesandAsians

Smallest cock gets locked

imgur.com category @chant9

An extremely consistent release schedule

imgur.com category @AmpleWang

Chastity Fantasy: Caption 145. Her reputation precedes her. Will she be able to "crack" him?

imgur.com category @wellhowaboutmaybe

At least you'll be flexible by the end

imgur.com category @PM_Me_Caption_Ideas

No excuses

imgur.com category @Iamonefatman

Size matters. To her.

imgur.com category @prettybadhorse

Won't you rest a little while?

imgur.com category @castempress

Got to know when to hold 'em and when to cage 'em... (OC)

imgur.com category @castempress

There's nowhere to escape the chastity cloud... (OC)

imgur.com category @castempress

Met a kinky girl playing D&D

imgur.com category @xChangeFan

Should have read the contract

imgur.com category @unusual_dialogue

This is no time to be selfish.

imgur.com category @prettybadhorse

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

imgur.com category @SpikesandAsians

You thought you were ready for this?

imgur.com category @prettybadhorse

Switching Up Roles

imgur.com category @gasolinetrain

How long you're going to spend in chastity

imgur.com category @Kalergian

You want to serve them?

imgur.com category @SoDaR95

Twitching

imgur.com category @NecessaryConfection

Winning the No-Nut-November Sweepstakes

imgur.com category @xChangeFan

Experimenting Methods

imgur.com category @SpikesandAsians

She likes to spice things up

imgur.com category @TotalLambdaUser

Taking Control

imgur.com category @Anti_Wil

You'll learn your place eventually.

imgur.com category @prettybadhorse

Born in the wrong century

imgur.com category @castempress

Now she has to wait another month

imgur.com category @NecessaryConfection

She might even make it permanent

imgur.com category @iBXxPwninxX

Roommate curious about mysterious delivery

imgur.com category @xChangeFan

Princess Amidala

imgur.com category @cindy_sissy

Full Control

imgur.com category @Anti_Wil

Your true calling

imgur.com category @PM_Me_Caption_Ideas

Dungeons and Chastity: Quest for the Missing Key

imgur.com category @xChangeFan

Make the right [Choice]

imgur.com category @SpikesandAsians

Tricky situation you've got yourself into

imgur.com category @chant9

Strap-on Misunderstanding

imgur.com category @LockedDragon

Cruel and Unusual Punishment

imgur.com category @PM_Me_Caption_Ideas

So anyway, I started blastin'

imgur.com category @NecessaryConfection

Her *final* decision

imgur.com category @NecessaryConfection

Danielle wants to have fun.

imgur.com category @Thumba95

Matching!

imgur.com category @gasolinetrain

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

imgur.com category @NecessaryConfection

She wants to wait until your wedding night

imgur.com category @xChangeFan

Cum comparison

imgur.com category @TheKatelynMarie

Boobs

imgur.com category @NecessaryConfection