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Cutesissycaptions

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

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

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Wake up, Sissy...

Wake up, Sissy...

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All this. . ..

All this. . ..

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Sissy truism #24

Sissy truism #24

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Can't Understand Why...

Can't Understand Why...

Cutesissycaptions

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

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

Cutesissycaptions

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

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

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You're turning into such an anal addict

You're turning into such an anal addict

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You know it's true...

You know it's true...

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I want to hear you say it

I want to hear you say it

Cutesissycaptions

Blowjob Practice!

Blowjob Practice!

Cutesissycaptions

Another boring public service announcement for sissies...

Another boring public service announcement for sissies...

Cutesissycaptions

You're so far gone!

You're so far gone!

Cutesissycaptions

Have you made any "bad" decisions? lol

Have you made any "bad" decisions? lol

Cutesissycaptions

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

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

Cutesissycaptions

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

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

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You're so far gone!

You're so far gone!

Cutesissycaptions

There's no going back

There's no going back

Cutesissycaptions

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

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

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This is what masturbation is for you now

This is what masturbation is for you now

Cutesissycaptions

Wouldn't you love a pretty necklace?

Wouldn't you love a pretty necklace?

Cutesissycaptions

But why do you let him?

But why do you let him?

Cutesissycaptions

Take it easy and trust the process...

Take it easy and trust the process...

Cutesissycaptions

Enjoy the Ride

Enjoy the Ride

Cutesissycaptions

Every part has a purpose, doesn't it?

Every part has a purpose, doesn't it?

Cutesissycaptions

You Look Like You're in Love, Bro:

You Look Like You're in Love, Bro:

Cutesissycaptions

Maybe you're nothing more than entertainment?

Maybe you're nothing more than entertainment?

Cutesissycaptions

Now you are addicted cum drainer for him

Now you are addicted cum drainer for him

Cutesissycaptions

Which attract you more, the hypnosis or the sissification?

Which attract you more, the hypnosis or the sissification?

Cutesissycaptions

Haha, No going back for you, Sissy!

Haha, No going back for you, Sissy!

Cutesissycaptions

Wish I was a girl so I can become a fucktoy

Wish I was a girl so I can become a fucktoy

Cutesissycaptions

How long would it take to grow a pretty bottom?

How long would it take to grow a pretty bottom?

Cutesissycaptions

cute cockloving sissy

cute cockloving sissy

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What are you willing to pay, hm?

What are you willing to pay, hm?

Cutesissycaptions

Wanna go camping with me bud?

Wanna go camping with me bud?

Cutesissycaptions

It's always been a clit.

It's always been a clit.

Cutesissycaptions

Did you ask yourself this question, sissy?

Did you ask yourself this question, sissy?

Cutesissycaptions

just anal doesnt have to mean anything

just anal doesnt have to mean anything

Cutesissycaptions

Caption GIF by tomtame

Caption GIF by tomtame

Cutesissycaptions

Anyone obsessed with boobs?

Anyone obsessed with boobs?

Cutesissycaptions

These are so your relationship goals, sissy!

These are so your relationship goals, sissy!

Cutesissycaptions

The "tipping point" is different for everyone ;)

The "tipping point" is different for everyone ;)

Cutesissycaptions

Weddings are interesting...

Weddings are interesting...

Cutesissycaptions

Good Friends

Good Friends

Cutesissycaptions

Bounce baby bounce!

Bounce baby bounce!

Cutesissycaptions

A "tip" for sissy happiness

A "tip" for sissy happiness

Cutesissycaptions

It's just too small!

It's just too small!

Cutesissycaptions

There really is no going back! You're in too deep!

There really is no going back! You're in too deep!

Cutesissycaptions

Sissy math...

Sissy math...

Cutesissycaptions

You have a girl's mouth.

You have a girl's mouth.

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