JamieSissyCaption: Videos, Pictures & GIFs

Dripping Hot Morning Service: Sissy Barista Edition'

Dripping Hot Morning Service: Sissy Barista Edition

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Global sissy slut spectacle: Your ultimate humiliation'

Global sissy slut spectacle: Your ultimate humiliation

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Begging for Daddy's Dominance'

Begging for Daddy's Dominance

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Dirty Heels & Daddy's Throat Bully'

Dirty Heels & Daddy's Throat Bully

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When Did You Kneel & Know You Were Just the Backup Bitch?'

When Did You Kneel & Know You Were Just the Backup Bitch?

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Dare to Dive In When He Demands You Take Her Spot?'

Dare to Dive In When He Demands You Take Her Spot?

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Throat Training 101: Sissy Edition'

Throat Training 101: Sissy Edition

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Dare to Ride the SISSYTRAIN_v1.7? Bet You Can't Handle It!'

Dare to Ride the SISSYTRAIN_v1.7? Bet You Can't Handle It!

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Daddy's Plaything: Begging for Dominance'

Daddy's Plaything: Begging for Dominance

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Bro Job or No Job? Helping Your Mate Out Never Felt So Right'

Bro Job or No Job? Helping Your Mate Out Never Felt So Right

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Oops, Forgot to Log Out? Now You're My Sissy Slut'

Oops, Forgot to Log Out? Now You're My Sissy Slut

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Dirty Pretend Play: Be His Slutty Wife Tonight'

Dirty Pretend Play: Be His Slutty Wife Tonight

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Filthy Weekend Fuckfest!'

Filthy Weekend Fuckfest!

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Shocked or Aroused? This Sissy Slut's Reaction Will Blow Your Mind'

Shocked or Aroused? This Sissy Slut's Reaction Will Blow Your Mind

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Think He's Gonna Seal the Deal This Time?'

Think He's Gonna Seal the Deal This Time?

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Daddy Owns This Sissy Slut Now'

Daddy Owns This Sissy Slut Now

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What would you do if someone found your sissy stash?'

What would you do if someone found your sissy stash?

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Would you accept an offer like that?'

Would you accept an offer like that?

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Would you like to have a buddy to watch porn with?'

Would you like to have a buddy to watch porn with?

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If you can’t get a girlfriend, just become one'

If you can’t get a girlfriend, just become one

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Do you think they’ll be proud of you?'

Do you think they’ll be proud of you?

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Would you like to be sissified by an older guy?'

Would you like to be sissified by an older guy?

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Daddy will make a real star out of you'

Daddy will make a real star out of you

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You just didn’t want to end up homeless…'

You just didn’t want to end up homeless…

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You came back a bit different from the school exchange'

You came back a bit different from the school exchange

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Next time, be careful what you sign'

Next time, be careful what you sign

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Would you like your roommate to caught you like that?'

Would you like your roommate to caught you like that?

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Will you repay him now?'

Will you repay him now?

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Would you like to spend a Valentine’s Day with your buddy?'

Would you like to spend a Valentine’s Day with your buddy?

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Would you like someone to lock you in a cage?'

Would you like someone to lock you in a cage?

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From now on, whenever your boyfriend leaves, you run to his room'

From now on, whenever your boyfriend leaves, you run to his room

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Now Halloween is so much more fun'

Now Halloween is so much more fun

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The best date ever!'

The best date ever!

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You just wanted to help a friend in need…'

You just wanted to help a friend in need…

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My body started changing after I tried to prove him wrong'

My body started changing after I tried to prove him wrong

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You need to make sure no one ever finds out about this'

You need to make sure no one ever finds out about this

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They were supposed to contact you, but they never called'

They were supposed to contact you, but they never called

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