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Sissycaptionstories

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by MichelleVenus97 from SissyCaptionStories

How You Became Addicted

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by accountens from SissyCaptionStories

You prank your friend by becoming his sissy slut ;)

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by CaptionsOnCommand from SissyCaptionStories

CaptionShorties: Drunk Buddy

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by stoak_too from SissyCaptionStories

The New You

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by [deleted] from SissyCaptionStories

Best secretary in town

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by JamesHayesee from SissyCaptionStories

Dance for him, sissy!

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by Mootzgoo from SissyCaptionStories

Bud is always getting wasted at my place...

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by CicadaWhole1428 from SissyCaptionStories

Daddy is going to bully you into enjoying his cock~

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by serenehypno from SissyCaptionStories

You're not gay, but that ass is quite tempting 😳

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by ssatyr7 from SissyCaptionStories

The bully becomes the bullied

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by egx123 from SissyCaptionStories

You're a slutty drunk

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by TheQrious1 from SissyCaptionStories

Your sister's boyfriend

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by Winter-Town621 from SissyCaptionStories

Dance for him, sissy!

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by TheVeryBestOnly from SissyCaptionStories

How It Started

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by Old_Competition_5792 from SissyCaptionStories

They were supposed to contact you, but they never called

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by Blackwidow0619 from SissyCaptionStories

If you get ghosted i’ll let you use my ass as a treat

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by boomplantar from SissyCaptionStories

Be A Good Friend!?

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by Distinct-Thanks6093 from SissyCaptionStories

You have such a busy schedule

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by [deleted] from SissyCaptionStories

She tried to pull a prank on you... but ha! The prank's on her!

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by bisexualpatel from SissyCaptionStories

I become a different person

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by Party-Shirt8081 from SissyCaptionStories

Your Friend Was Right

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by Mammoth-Clock9453 from SissyCaptionStories

Rapid Feminization Disorder claims another victim

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by OkPomelo2730 from SissyCaptionStories

What are friends for?

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by Sissy-Fiction from SissyCaptionStories

A booty full of hot, creamy cum and a bull ready to fuck your

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by Successful-Emu-1293 from SissyCaptionStories

When You Started Dressing Up Around Your Roommate

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by Successful_Trash_830 from SissyCaptionStories

Of course we love it

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by SquirtingTrap from SissyCaptionStories

My boss really likes how I dress now

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by [deleted] from SissyCaptionStories

Turns out you shouldn't bet with your girlfriend... but hey,

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by Ankita0001 from SissyCaptionStories

Would you want this to happen to you ? :) ;)

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by TheQrious1 from SissyCaptionStories

A sissy's first date

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by Katiee4uu from SissyCaptionStories

How I ended up getting fucked by my online jerkbuddy! 😉

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by Winter-Town621 from SissyCaptionStories

You wanted to get caught, didn’t you? 😘

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by mimi_boyy from SissyCaptionStories

Studying HARD

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by InformalAd3443 from SissyCaptionStories

Caught by her bf

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by stoak_too from SissyCaptionStories

Rapid Feminization Disorder claims another victim

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by OnlyMiaaa from SissyCaptionStories

If only your landlord had seen you dolled up sooner!!

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by Brian_Lewis48 from SissyCaptionStories

You're not sure why so many people are scared of getting their

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by mimi_boyy from SissyCaptionStories

Think you'll start going out more often...

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by OkPomelo2730 from SissyCaptionStories

You can't watch a movie without having a salty snack🍿

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by TheQrious1 from SissyCaptionStories

Your followers made you do it!

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by mimi_boyy from SissyCaptionStories

And you were second-guessing yourself!

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by Quick-Host7794 from SissyCaptionStories

Gf's toxic ex

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by SnooPickles5129 from SissyCaptionStories

Better than a girl

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by pinksissypanda from SissyCaptionStories

Caught by the rich neighbour

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by TwistedTranSista from SissyCaptionStories

Helping your roommate has awoken the Sissy you were always meant

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by Sissy-Fiction from SissyCaptionStories

Next year, you're thinking of asking if the loser can get fucked

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by Euphoric_Amount_9464 from SissyCaptionStories

The Accident

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by LockerRoomHero from SissyCaptionStories

Your Friend's Cum

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by finiteless_chicks from SissyCaptionStories

Fucked by your best friend... a dream come true

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by Old_Competition_5792 from SissyCaptionStories

Such a lovely girlfriend

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by stoak_too from SissyCaptionStories

Becoming His Bitch

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by Successful_Trash_830 from SissyCaptionStories

I'm better than my sister anyway

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by SnooPickles5129 from SissyCaptionStories

Kinda Sexy

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by Ok_Antelope9195 from SissyCaptionStories

Diagnosis: Slut

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by Onedollarsissy from SissyCaptionStories

Cheerleader tryout part 1

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by Kaneki_Ken009 from SissyCaptionStories

Caught by my brother in law...

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by Reasonable_Still994 from SissyCaptionStories

What your late night texting usually leads to...

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by TwistedTranSista from SissyCaptionStories

Your roommate has been training herself just for you

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by Euphoric_Amount_9464 from SissyCaptionStories

From the bully to bitch

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by Realfield2001 from SissyCaptionStories

Exit Interview

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