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Sissycaptionstories

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by pinksissypanda from SissyCaptionStories

How to become popular

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by WetDreams6969 from SissyCaptionStories

Sissy slut loses bet - PT.2

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by Own_Habit_5609 from SissyCaptionStories

You try to deny that this is why you always invite him over,

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by LockerRoomHero from SissyCaptionStories

Edibles make you HORNY

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by idk57277 from SissyCaptionStories

I hope i get a bud like this 🤷‍♂️

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by AdApprehensive8437 from SissyCaptionStories

Sissy Streamer

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by egx123 from SissyCaptionStories

Did such a good job that you kept hiring him

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by [deleted] from SissyCaptionStories

A small Career change

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by sirtaco8 from SissyCaptionStories

Vibrator

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by TwistedTranSista from SissyCaptionStories

You first turned Sissy to help, now you can’t ever go back

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by mimi_boyy from SissyCaptionStories

Time to get wet, sissy!

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by [deleted] from SissyCaptionStories

The last minute replacement

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by thegoodsissyBBC from SissyCaptionStories

There's no going back now...

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by Separate-Main599 from SissyCaptionStories

Times are tough

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by Spiritual-Basket-847 from SissyCaptionStories

A sissy's first date

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by Femboii8D from SissyCaptionStories

No homo bro

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by Realfield2001 from SissyCaptionStories

Yes Sir

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by mimi_boyy from SissyCaptionStories

Talk about a 5-star ride

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by Western-Outside788 from SissyCaptionStories

Oral Fixation

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by Old_Competition_5792 from SissyCaptionStories

Now you have to visit him after work…

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by candycreatescaps from SissyCaptionStories

Entering the Friend Zone

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by mimi_boyy from SissyCaptionStories

What your late night texting usually leads to...

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by Euphoric_Amount_9464 from SissyCaptionStories

You lost a bet (part 2)

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by Old_Competition_5792 from SissyCaptionStories

Do you think you would win against your buddy?

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by NoDoctor3099 from SissyCaptionStories

Losing control (4/4)

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by Old_Competition_5792 from SissyCaptionStories

Would you like to have a girlfriend like that?

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by JoyPornAdmin from SissyCaptionStories

How to tell you're a Sissy

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by Jennny_Denny69 from SissyCaptionStories

following ur dream

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by AnyaBray from SissyCaptionStories

Should I tell him my sissy secret?~

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by SissyCaptionPalace from SissyCaptionStories

Teasing neighbor gone wrong!?

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by TheQrious1 from SissyCaptionStories

Movie Night

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by Winter-Town621 from SissyCaptionStories

A Scrawny Nerd's Revenge

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by Euphoric_Amount_9464 from SissyCaptionStories

Husbands revenge

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by DurianPlastic524 from SissyCaptionStories

From jerk bud to cocksucker

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by Throwaway1929489 from SissyCaptionStories

You really proved him wrong

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by mindbreakcaptions from SissyCaptionStories

Your friend has a great plan to get you both laid

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by Wilder_Entity from SissyCaptionStories

when your football team loses, you win something else...

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by Ok_Magazine46 from SissyCaptionStories

Paying off your debt

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by Trick_Ad_511 from SissyCaptionStories

Your new favorite game

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by LockerRoomHero from SissyCaptionStories

Sissy Contract

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by Difficult_Load_4132 from SissyCaptionStories

I hate this

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by Old_Competition_5792 from SissyCaptionStories

Would you like someone to lock you in a cage?

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by MichelleVenus97 from SissyCaptionStories

That worked just fine!

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by stoak_too from SissyCaptionStories

A Scrawny Nerd's Revenge

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by Additional-Hunter231 from SissyCaptionStories

Do you believe in magic?

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by LockerRoomHero from SissyCaptionStories

First College Party

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by stoak_too from SissyCaptionStories

Would you stay?

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by Old_Competition_5792 from SissyCaptionStories

One silly mistake changed your entire life

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by Sissy_Jessiexo from SissyCaptionStories

Admit it. You wanted to get caught

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by OkPomelo2730 from SissyCaptionStories

It's hard work being a sissy

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by LockerRoomHero from SissyCaptionStories

Frat Party Fun

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by Euphoric_Amount_9464 from SissyCaptionStories

The blackmail (part 1)

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by Euphoric_Amount_9464 from SissyCaptionStories

Know your place slut

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by accountens from SissyCaptionStories

Bi-curious or just a sissy?

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by AdApprehensive8437 from SissyCaptionStories

Your First REAL Cock - Part 1 of 3

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by JamesHayesee from SissyCaptionStories

Gym buds

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by New-Bench-3495 from SissyCaptionStories

Your followers made you do it!

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by blackneckgrowth from SissyCaptionStories

Your freinds always said you looked cute and girly and you hated

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by takeachance194 from SissyCaptionStories

Sleepovers always get interesting late at night...

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by mimi_boyy from SissyCaptionStories

All this "hiking" is gonna get you sore!

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