Categories

SELECT COUNT(*) FROM gallery WHERE topic_category="sissycaptions"

My fantasy is to meet a single mom with a sissy son. I’d marry her, properly adopt him, feminize him into a true sissy and be the man of the house in this wholesome, mutually sexual relationship between all 3 of us. Our happy family.

My fantasy is to meet a single mom with a sissy son. I’d marry her, properly adopt him, feminize him into a true sissy and be the man of the house in this wholesome, mutually sexual relationship between all 3 of us. Our happy family.

It’s what you crave 💕

It’s what you crave 💕

Yes

lick up your little mess you made on daddys tummy!

lick up your little mess you made on daddys tummy!

Sissy goals

Sissy goals

When your sissy training has lead you to the perfect place in life!

When your sissy training has lead you to the perfect place in life!

mhmmm you're more than right

mhmmm you're more than right

Keep practicing like a good slut...

Keep practicing like a good slut...

Cant go back anymore

Cant go back anymore

Always!…

Become a pornstar

Become a pornstar

take a selfie with his massive cock to show everyone what a whore you are

take a selfie with his massive cock to show everyone what a whore you are

Sexuality is so simple

Sexuality is so simple

Question Time

Question Time

Submit Slut

Submit Slut

It’s your time…

It’s your time…

It's time ⏲

It's time ⏲

It's only natural 😌

It's only natural 😌

Suprise for the little Princess

Suprise for the little Princess

Clean up your masters Load. You serve Alpha Males Now.

Clean up your masters Load. You serve Alpha Males Now.

You are owned..

You are owned..

Being a sissy was best decision I've made in my life

Being a sissy was best decision I've made in my life

Good things await the sissy who takes initiative 😉

Good things await the sissy who takes initiative 😉

Now they only hit you in the face with their big meaty cocks 🤤

Now they only hit you in the face with their big meaty cocks 🤤

Listen to her

Listen to her

Let’s play another game… vote in the comments

Let’s play another game… vote in the comments

I hope my pose is submissive enough, sigh...

I hope my pose is submissive enough, sigh...

Show daddy what he’s working with sissy! 🤤🥰 in collaboration u/babimunizTS

Show daddy what he’s working with sissy! 🤤🥰 in collaboration u/babimunizTS

I love it this way!

I love it this way!

Woke up craving cock so bad🥴

Woke up craving cock so bad🥴

Isn’t it true sissy

Isn’t it true sissy

Your Future

Your Future

Which naughty boy needs to be bred by daddy?

Which naughty boy needs to be bred by daddy?

It was never suppose to be like this🙈😋

It was never suppose to be like this🙈😋

Your bully made you wear the 'girls' uniform to school. You should thank him for helping you take the first step towards bein a Sissy..

Your bully made you wear the 'girls' uniform to school. You should thank him for helping you take the first step towards bein a Sissy..

When you lose your anal virginity at the same time <3

When you lose your anal virginity at the same time <3

Mmmh

Your roommate walked in on you playing with a Huge cock... so you invite him to take out his big cock too! two is better than one, after all.

Your roommate walked in on you playing with a Huge cock... so you invite him to take out his big cock too! two is better than one, after all.

You thought of yourself as a MAN before the pandemic... but now youre a proper sissy girl.

You thought of yourself as a MAN before the pandemic... but now youre a proper sissy girl.

You look so much prettier with his cum on your face :)

You look so much prettier with his cum on your face :)

My destiny

They are tears of joy!

They are tears of joy!

Hopefully your roommate likes your new Outfit enough, so that he'll bend you over & Pound your sissy ass

Hopefully your roommate likes your new Outfit enough, so that he'll bend you over & Pound your sissy ass

Open wide…

Open wide…

You live for it

You live for it

Don't fight it girls♥️

Don't fight it girls♥️

It’s all you can think about

It’s all you can think about

Creepy Neighbor pt 1: I was crossdressing like I had many times before, but this time was different. My neighbor had been snooping around and snuck his way in the house. He had a thing for sissies, and he knew I just had my 18th birthday, so he finally m

Creepy Neighbor pt 1: I was crossdressing like I had many times before, but this time was different. My neighbor had been snooping around and snuck his way in the house. He had a thing for sissies, and he knew I just had my 18th birthday, so he finally m

Question Time

Question Time

You need this…

You need this…

Need a Tx Daddy

Need a Tx Daddy

One way or another, his big dick will be balls deep in your sissy body 🧚‍♀️

One way or another, his big dick will be balls deep in your sissy body 🧚‍♀️

Sissy Training with the Girls

Sissy Training with the Girls

You’re the toy…

You’re the toy…

Can't resist (Caution: British pun...)

Can't resist (Caution: British pun...)

Asspire..

Time to get owned by a real man 💞

Time to get owned by a real man 💞

Did anyone catch you crossdressing?

Did anyone catch you crossdressing?

Wear

Wear "Fuck Me Pumps" = Get fucked?

It wasn't always daddy's hole, bit with all the hard work he's put in feminizing it, it's only fair that it belongs to him now

It wasn't always daddy's hole, bit with all the hard work he's put in feminizing it, it's only fair that it belongs to him now

Would you become a street whore?

Would you become a street whore?

It's so true

It's so true

Daddy loves to tease you before he rearranges your insides <3

Daddy loves to tease you before he rearranges your insides <3

Become his bitch. Become Alpha Owned.

Become his bitch. Become Alpha Owned.

Destroy me

Sissy boys are for a reason

Sissy boys are for a reason

Which one would you rather be?

Which one would you rather be?

Even before

Even before

Use your girly assets to make him hard for you sissy 🍆😍

Use your girly assets to make him hard for you sissy 🍆😍

Perfect colour

Perfect colour

i need daily cum🤤

i need daily cum🤤

The Sissy's Mantra

The Sissy's Mantra

I’m definitely a sissy now! Say it with me 😉

I’m definitely a sissy now! Say it with me 😉

Yep

Make your dreams come true…

Make your dreams come true…

My future wifey wanted me to turn our own life into a caption

My future wifey wanted me to turn our own life into a caption

Can I be a sissy secretary? caption please

Can I be a sissy secretary? caption please

Just buy me shoes and pretty clothes Daddy, and I'll do anything you want...

Just buy me shoes and pretty clothes Daddy, and I'll do anything you want...

One of my admirers captioned me

One of my admirers captioned me

Options

Replace your toy…

Replace your toy…

Will make captions for people feel free to send requests

Will make captions for people feel free to send requests

It's your destiny to be his sissy bitch, forever.

It's your destiny to be his sissy bitch, forever.

What Stage Are You On?

What Stage Are You On?

YAY! I just got to 1k karma! Thanks for all your help...but I can't help but wonder what's happening to me...

YAY! I just got to 1k karma! Thanks for all your help...but I can't help but wonder what's happening to me...

Thanks to U/lyndseygurl for the caption. Sissy Amanda loves it

Thanks to U/lyndseygurl for the caption. Sissy Amanda loves it

Goals

Anyone else genuinely think it would be hot to be kidnapped, feminized, and forced into prostitution?

Anyone else genuinely think it would be hot to be kidnapped, feminized, and forced into prostitution?

What age did you realize you’re a sissy?

What age did you realize you’re a sissy?

Down the 🐇 hole

Down the 🐇 hole

You had a wrestling match to determine who made the rules of the house... You didn't win.

You had a wrestling match to determine who made the rules of the house... You didn't win.

Don’t deny yourself…

Don’t deny yourself…

My favorite hobby is begging hung daddies for their cum.

My favorite hobby is begging hung daddies for their cum.

do ANYTHING to please daddy!

do ANYTHING to please daddy!

Sluts❤️🖤

Sluts❤️🖤

Love to be treated like this!

Love to be treated like this!

Express your talents

Express your talents

Be Yourself, Be Happy… (art Kantai - caps fenris616)

Be Yourself, Be Happy… (art Kantai - caps fenris616)

Show daddy what’s for supper

Show daddy what’s for supper

I found mine

I found mine