Chastity slave thought he would be free in 4 days

Humiliation and Loser Captions

sissypansyweakling Thank You Mistress!!!

Show Your Tiny Dick Welcome :)

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Beg Me for My Pussy

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scrantonslave

Tease and Denial Slaves

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Little Gift for a Little Dick Slave

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scrantonslave

Mistress Locking Up Your Cock

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When You Have a Shrimp Dick, You Don’t Ca ...

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Captions for Tiny Dicks

Watch How Dumb Giving a Tiny Dick a BJ Looks

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Small Penis Humiliation GIFs

Douglas t. Gugel aka tiny dick sissy faggot wimp Yep that's how it looks when I get my tiny little dicky sucked and I cum in like 2 to 3 seco...

Tiny Cocks All Need Keyholders

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expoguy In a perfect world :-)

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Rule 1: A Sissy Does Not Have a Cock

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Sissification Captions

Fem Sissy Would you two suck it?

wannabesphcuck Hell yeah she could use and abuse me however she wanted ?

passaround I would suck it until i was told to stop

Will You Be My Sissy?

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Sissification Captions

Matt8 Won't be much work to transform me.

Fem Sissy hehehe

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This Strapon is for Your Sissy Ass

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ShowYourTinyDick Awww such a scared little sissy wimp lol

SPH Caption: My Finger Brings Me More Pleasure

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Strapons, CEI & Hot Captions

Captions for Tiny Dicks

Matt8 Your finger won't can last long enough too

Mistress Cums So Hard While Strapon Fucking His ...

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Femdoms Rule

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Stroke Your Dick at Your Mouth with My Strapon ...

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Femdoms Rule

Strapons, CEI & Hot Captions

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Femdoms Rule Remember to swallow!

Jerk off and edge yourself all day long

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Let Me Watch

Fave Cuckold Caption Pics

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Let Me Watch

Cuckold Chastity Slavery

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Everyone can see your little penis!

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Big Cock Slave

Tiny Dick Getting Bullied

His owner keeps his bitch ass locked up!

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Dick Too Small for Chastity

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sis bella I hope they do

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From a Man to a Sissy Girl

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Fem Sissies

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Everyone on campus knows you’re a sissy

Sissification Captions

Sissy Dildo Training Tip: Ride it Harder

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Sissy Academy of Feminization

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Drop to your knees and worship what you see

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Pay Piggy

Facesitting Goddess Pics and Gifs

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sissycock Its true!! I slipped out of the CB 6000

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Make Your Chastity Slave Suffer

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Get Used to the Blue Balls, Chastity Slave