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Losing Never Felt So Good: A Sissy's Dream Bet

Ever bet your dignity on a game you knew you'd lose? This femboy sure did, and now they're paying up in the most delicious way possible. Watch as pride takes a backseat to pleasure, and losing becomes the ultimate win. Perfect for those who love a sissycaption fantasy come to life.
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Your holes are the only thing of worth you have, use them' Your holes are the only thing of worth you have, use them
I think I'm seeing my brother in a whole new light now' I think I'm seeing my brother in a whole new light now
Dirty Talk or Hang Up? She’s Begging for Your Cock!' Dirty Talk or Hang Up? She’s Begging for Your Cock!
Sissy's Wild Ride: Corporate Desires Unleashed!' Sissy's Wild Ride: Corporate Desires Unleashed!
Now you know' Now you know
Think You Can Handle This? Too Bad Your Cock's Pathetic!' Think You Can Handle This? Too Bad Your Cock's Pathetic!
You found out and accidentally got hard' You found out and accidentally got hard
Teacher’s Pet' Teacher’s Pet
Filthy Cuckold Fantasies Unleashed' Filthy Cuckold Fantasies Unleashed
Acceptance is the only choice' Acceptance is the only choice
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My friend show me his cock and I decided to tell him my secret!' My friend show me his cock and I decided to tell him my secret!
Sissy Caption Stories
Sissy's Ultimate Cuckold Fantasy Unleashed' Sissy's Ultimate Cuckold Fantasy Unleashed
Sissy Caption Stories
Got drunk and dressed up and decided to see if bro wanted to come over and hang🤭 would you?' Got drunk and dressed up and decided to see if bro wanted to come over and hang🤭 would you?
Sissy Caption Stories
There was nothing to regret' There was nothing to regret
Sissy Caption Stories Sissy Captions Still Straight Captions
Not gay at all' Not gay at all
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Earn Your Cream: Are You a Good Boy or a Naughty Slut? 😈' Earn Your Cream: Are You a Good Boy or a Naughty Slut? 😈
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Filthy Sissy Addict Craves More' Filthy Sissy Addict Craves More
Sissy Caption Stories Sissy Captions
Would you like to spend a Valentine’s Day with your buddy?' Would you like to spend a Valentine’s Day with your buddy?
JamieSissyCaption NSFW Captions Sissy Caption Stories Sissy Captions Still Straight Captions
From Roomie to Babe: Turning Your Sissy Side into His GF Material' From Roomie to Babe: Turning Your Sissy Side into His GF Material
Sissy Caption Stories Sissy Captions
Blonde Bombshell Gets Her Debt Cleared in the Hottest Way' Blonde Bombshell Gets Her Debt Cleared in the Hottest Way
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Sissy face fucked by her daddy😈🍆' Sissy face fucked by her daddy😈🍆
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Tricking the Shark' Tricking the Shark
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My roommate's diary' My roommate's diary
NSFW Captions Sissy Caption Stories Sissy Captions
He’s going to make you a very famous sissy now💕 part 2' He’s going to make you a very famous sissy now💕 part 2
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Sissy cock slut' Sissy cock slut
Sissy Caption Stories
Disguised For The Exam! Part 8' Disguised For The Exam! Part 8
Sissy Caption Stories Sissy Captions
Breaking the sissy' Breaking the sissy
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Born to Be a Girly Sissy Slut [Voiced AF!]' Born to Be a Girly Sissy Slut [Voiced AF!]
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The "true" story of how I became a Cock Sucking Slut - Part6' The "true" story of how I became a Cock Sucking Slut - Part6
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Her hard work paid off' Her hard work paid off
deepthroat Sissy Caption Stories
Good ending to a bad day' Good ending to a bad day
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