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SissyCaptionStories

my hostel experience in Spain

my hostel experience in Spain

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Bodybuilding

Bodybuilding

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You used to hate the idea of chastity. But once you had your

You used to hate the idea of chastity. But once you had your

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The new intern

The new intern

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Disguised For The Exam Part 2

Disguised For The Exam Part 2

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Curiosity breeds Sissy Sluts 💜

Curiosity breeds Sissy Sluts 💜

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Would you replace his sex toy?

Would you replace his sex toy?

SissyCaptionStories

Sissy vs a BBC Bull featuring me 👉👈🥺

Sissy vs a BBC Bull featuring me 👉👈🥺

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If a man takes you out, thank him properly

If a man takes you out, thank him properly

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Getting recognized

Getting recognized

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Love this

Love this

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[OC] C'mon dude ..... try being a good friend atleast once :)

[OC] C'mon dude ..... try being a good friend atleast once :)

SissyCaptionStories

[OC] Does anyone else want to be trained by a mistress ? :) ;)

[OC] Does anyone else want to be trained by a mistress ? :) ;)

SissyCaptionStories

[OC] Isn't that the story of your life ? (Yes, I am talking to

[OC] Isn't that the story of your life ? (Yes, I am talking to

SissyCaptionStories

Your girlfriend finds out you're a sissy when she asks for a

Your girlfriend finds out you're a sissy when she asks for a

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Fantasy become reality

Fantasy become reality

SissyCaptionStories

Realizing I'm better at being a girl

Realizing I'm better at being a girl

SissyCaptionStories

I've missed making captions ;)

I've missed making captions ;)

SissyCaptionStories

You'll never make that mistake again

You'll never make that mistake again

SissyCaptionStories

My first workout session with my Dad's trainer (2/3)

My first workout session with my Dad's trainer (2/3)

SissyCaptionStories

Turns out you're pretty good at sucking dick!

Turns out you're pretty good at sucking dick!

SissyCaptionStories

Would you participate in this trend?

Would you participate in this trend?

SissyCaptionStories

Just Be Yourself

Just Be Yourself

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Passed Around

Passed Around

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Your boss has been really impressed with how you've been adapting

Your boss has been really impressed with how you've been adapting

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House Sitting Gone Wild

House Sitting Gone Wild

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Stress relief (part 2)

Stress relief (part 2)

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a little bedtime story about a powerfull voice(1:13)

a little bedtime story about a powerfull voice(1:13)

SissyCaptionStories

Now he’s your Daddy

Now he’s your Daddy

SissyCaptionStories

Interesting parts of a Sissy's day!

Interesting parts of a Sissy's day!

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[OC] Seems like you weren't lying about being tight :) ;)

[OC] Seems like you weren't lying about being tight :) ;)

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harmless prank

harmless prank

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how disagreements usually end for me

how disagreements usually end for me

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Melinda part 1/5

Melinda part 1/5

SissyCaptionStories

Your boss swore he wouldn’t tell anyone

Your boss swore he wouldn’t tell anyone

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There's no going back now...

There's no going back now...

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My kind of party

My kind of party

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Hopefully he'll need convincing again next week!

Hopefully he'll need convincing again next week!

SissyCaptionStories

Your uncles break you in!

Your uncles break you in!

SissyCaptionStories

Much needed R&R

Much needed R&R

SissyCaptionStories

You never thought your dream girl would have a dick bigger than

You never thought your dream girl would have a dick bigger than

SissyCaptionStories

Helping out a Bro?

Helping out a Bro?

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Fucked like a sissy slut

Fucked like a sissy slut

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A Scrawny Nerd's Revenge

A Scrawny Nerd's Revenge

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A maid duty

A maid duty

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Becoming His Bitch

Becoming His Bitch

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Do you remember what happened last night ? :) :p

Do you remember what happened last night ? :) :p

SissyCaptionStories

Blonde Bitch

Blonde Bitch

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Blowjob GIF by ls2222

Blowjob GIF by ls2222

SissyCaptionStories

Become a secretary today... ;)

Become a secretary today... ;)

* T O P L I S T * T O P L I S T *