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SissyCaptionStories

Studies & Biologist Say it's Not Gay!! So Get Sucking

Studies & Biologist Say it's Not Gay!! So Get Sucking

SissyCaptionStories

Every time is like the first time...

Every time is like the first time...

SissyCaptionStories

A warden delight (OC)

A warden delight (OC)

SissyCaptionStories

Yoga Sissification (OC)

Yoga Sissification (OC)

SissyCaptionStories

Have you been enlightened yet ? :) ;)

Have you been enlightened yet ? :) ;)

SissyCaptionStories

I'm A Sissy For Daddy Part 3 (Step Daddy Caption)

I'm A Sissy For Daddy Part 3 (Step Daddy Caption)

SissyCaptionStories

Next tkme you'll get caught on purpose...

Next tkme you'll get caught on purpose...

SissyCaptionStories

Special video

Special video

SissyCaptionStories

When in doubt..

When in doubt..

SissyCaptionStories

Cheerleader tryout part 2 (with sound)

Cheerleader tryout part 2 (with sound)

SissyCaptionStories

It's not even gay. Right?

It's not even gay. Right?

SissyCaptionStories

delicious meal

delicious meal

SissyCaptionStories

[OC] He does seem like a very nice boss :) :p

[OC] He does seem like a very nice boss :) :p

SissyCaptionStories

Are all girlfriends devious?

Are all girlfriends devious?

SissyCaptionStories

Everybody Likes to Watch

Everybody Likes to Watch

SissyCaptionStories

If you're on this subreddit, this moment is inevitable...

If you're on this subreddit, this moment is inevitable...

SissyCaptionStories

Who would've thought... ;)

Who would've thought... ;)

SissyCaptionStories

Sissy April Fool’s

Sissy April Fool’s

SissyCaptionStories

Caught staring in the woods

Caught staring in the woods

SissyCaptionStories

Annoying ex

Annoying ex

SissyCaptionStories

Seems like you are gonna get a raise :) ;)

Seems like you are gonna get a raise :) ;)

SissyCaptionStories

Abused by a ghost

Abused by a ghost

SissyCaptionStories

taking the walk of shame 🙈

taking the walk of shame 🙈

SissyCaptionStories

Neighbor cums all over me

Neighbor cums all over me

SissyCaptionStories

Old Caption I Want To Show The World

Old Caption I Want To Show The World

SissyCaptionStories

You loved it sissy

You loved it sissy

SissyCaptionStories

Sissy journalist

Sissy journalist

SissyCaptionStories

The sissy pills

The sissy pills

SissyCaptionStories

Lose The Bet, Lose Your Manhood (w/ sound)

Lose The Bet, Lose Your Manhood (w/ sound)

SissyCaptionStories

A new chapter

A new chapter

SissyCaptionStories

Drunk sissy

Drunk sissy

SissyCaptionStories

Pimped By My Girlfriend Pt 3

Pimped By My Girlfriend Pt 3

SissyCaptionStories

Taking your mom’s date

Taking your mom’s date

SissyCaptionStories

You can't wait till he comes over again...

You can't wait till he comes over again...

SissyCaptionStories

Part of the Team

Part of the Team

SissyCaptionStories

Team Cum Dump

Team Cum Dump

SissyCaptionStories

Trying to Prank Your Coworker Gone Wrong ;)

Trying to Prank Your Coworker Gone Wrong ;)

SissyCaptionStories

My Sissy Dad tried to keep our hung trainer to himself 😡

My Sissy Dad tried to keep our hung trainer to himself 😡

SissyCaptionStories

Decision time

Decision time

SissyCaptionStories

Losing the game

Losing the game

SissyCaptionStories

got my drink of choice on my 21st birthday!

got my drink of choice on my 21st birthday!

SissyCaptionStories

Total Commitment

Total Commitment

SissyCaptionStories

The Perfect Girls Night!

The Perfect Girls Night!

SissyCaptionStories

Kidnapped By the Sissy Modeling Agency

Kidnapped By the Sissy Modeling Agency

SissyCaptionStories

Next time don’t forget to log off

Next time don’t forget to log off

SissyCaptionStories

Melinda part 4/5

Melinda part 4/5

SissyCaptionStories

Your work colleagues find out you're a sissy and surprise you

Your work colleagues find out you're a sissy and surprise you

SissyCaptionStories

That's how everything starts - Part 4

That's how everything starts - Part 4

SissyCaptionStories

NNN is right around the corner. Are you ready?

NNN is right around the corner. Are you ready?

SissyCaptionStories

I wanna start camming, but id rather try the real thing before

I wanna start camming, but id rather try the real thing before

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