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by NoWayStraight from Cutesissycaptions

Believe me, you should try it once and your eyes will roll as

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by thomas_the_tame from Cutesissycaptions

What are you, sissy?

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by thomas_the_tame from Cutesissycaptions

Is there such a thing as Spank Hypnosis?

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by thomas_the_tame from Cutesissycaptions

How it really goes for a sissy...

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by thomas_the_tame from Cutesissycaptions

Blackmail 2

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by BoringKate from Cutesissycaptions

Estrogen really made my tits kinda huge

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by BoringKate from Cutesissycaptions

Be a good girl for me

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by iLoveBlowjobstoo from Cutesissycaptions

not so straight after all

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by iLoveBlowjobstoo from Cutesissycaptions

your wife loves to watch

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by thomas_the_tame from Cutesissycaptions

Do you have a sissy friend yet?

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by BoringKate from Cutesissycaptions

It's just getting smaller and smaller

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by BoringKate from Cutesissycaptions

I love stretching you out!

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by SissyTittie from Cutesissycaptions

So true...

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by Cassiehack666 from Cutesissycaptions

Come in

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by thomas_the_tame from Cutesissycaptions

Each one is a gamble, sissy...it only takes one...

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by iLoveBlowjobstoo from Cutesissycaptions

just perfect

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by BoringKate from Cutesissycaptions

You're turning into such an anal addict

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by thomas_the_tame from Cutesissycaptions

Do you have a "roommate"?

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by mrcave81 from Cutesissycaptions

A sissy reward

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by thomas_the_tame from Cutesissycaptions

What was my name? Oh, right. Toy #3.

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by thomas_the_tame from Cutesissycaptions

It will at some point become normal...lol

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by BoringKate from Cutesissycaptions

Be a good girl for me

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by BoringKate from Cutesissycaptions

This is what masturbation is for you now

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by BoringKate from Cutesissycaptions

This is what masturbation is for you now

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by BoringKate from Cutesissycaptions

Be a good girl for daddy

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by thomas_the_tame from Cutesissycaptions

An imperfect sissy timeline

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by thomas_the_tame from Cutesissycaptions

It begins when it gets real. When did it get real for you?

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by PersonalityOk592 from Cutesissycaptions

No Going Back

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by SissyTittie from Cutesissycaptions

This is what I want today

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by thomas_the_tame from Cutesissycaptions

Is this how you view sissy captions?

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by thomas_the_tame from Cutesissycaptions

It's funny how sissies want to be trained, even though they don't

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by thomas_the_tame from Cutesissycaptions

Wake up, Sissy...

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by thomas_the_tame from Cutesissycaptions

All this. . ..

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by thomas_the_tame from Cutesissycaptions

Sissy truism #24

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by NoWayStraight from Cutesissycaptions

Can't Understand Why...

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by thomas_the_tame from Cutesissycaptions

No one says "be careful what you wish for" anymore?

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by BoringKate from Cutesissycaptions

You'll learn to love it even more than stroking that little clit!

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by BoringKate from Cutesissycaptions

You're turning into such an anal addict

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by sissycdxxx from Cutesissycaptions

You know it's true...

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by BoringKate from Cutesissycaptions

I want to hear you say it

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by swapdrops from Cutesissycaptions

Blowjob Practice!

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by thomas_the_tame from Cutesissycaptions

Another boring public service announcement for sissies...

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by BoringKate from Cutesissycaptions

You're so far gone!

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by thomas_the_tame from Cutesissycaptions

Have you made any "bad" decisions? lol

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by thomas_the_tame from Cutesissycaptions

What would you give to have her do this to you? lol

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by thomas_the_tame from Cutesissycaptions

Sissy hypnosis works even when you don't realize it's working.

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by BoringKate from Cutesissycaptions

You're so far gone!

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by BoringKate from Cutesissycaptions

There's no going back

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by thomas_the_tame from Cutesissycaptions

What was your first time like, sissy? (seriously! I want to know)

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by BoringKate from Cutesissycaptions

This is what masturbation is for you now

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by thomas_the_tame from Cutesissycaptions

Wouldn't you love a pretty necklace?

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by thomas_the_tame from Cutesissycaptions

But why do you let him?

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by thomas_the_tame from Cutesissycaptions

Take it easy and trust the process...

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by PersonalityOk592 from Cutesissycaptions

Enjoy the Ride

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by thomas_the_tame from Cutesissycaptions

Every part has a purpose, doesn't it?

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by AllenGoonsberg from Cutesissycaptions

You Look Like You're in Love, Bro:

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by thomas_the_tame from Cutesissycaptions

Maybe you're nothing more than entertainment?

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by NoWayStraight from Cutesissycaptions

Now you are addicted cum drainer for him

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by thomas_the_tame from Cutesissycaptions

Which attract you more, the hypnosis or the sissification?

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by Head_Ad_9061 from Cutesissycaptions

Haha, No going back for you, Sissy!

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