8 XXX : the caption

Feel the power

imgur.com category @[deleted]

You thought being a "nice guy" would get you the girl

imgur.com category @[deleted]

Aren't You Just the Cutest!

imgur.com category @Wannabesissyfuckpig

She's having more fun now than ever [caption]

imgur.com category @OneGentlemanOfVerona

You have the best jokes!

imgur.com category @sissy-discipline

Marry the man of your dreams, sissy

imgur.com category @[deleted]

Keep going down the rabbit hole, sissy!

gfycat.com category @PornMaker2048

Not the most difficult of choices...

imgur.com category @EdgyBananaInspector

How to be the best sissy you can be!

gfycat.com category @Accountnumbahtwo

Go to the gloryhole and start living your new life as a sissy cock slave!

gfycat.com category @PornMaker2048

Get caught in the act

imgur.com category @goonerbate2

I hope you like this one. The source video is sooo good.

gfycat.com category @Woolfix

You'll only have one job for the rest of your life, Sissy.

gfycat.com category @Sissycumslutandrea

You were so into sissy porn you decided to become the girl so you can always jack off to a perfect t-girl

gfycat.com category @goonerbate2

Went off the deep end

imgur.com category @Siseva

In goes the dildo, out goes your brain

gfycat.com category @MistressStella

Surrender to the power of real men

gfycat.com category @MistressStella

Girls in cute outfits get all the boys!

imgur.com category @[deleted]

Nothing beats the sensation except for... (gif)

imgur.com category @TherapistSummersTSSP

This is the only logical conclusion if you keep watching those hypnos, sissy

imgur.com category @ruskeleton

It'll be worth it once you're on the team

gfycat.com category @wongdongfromhongkong

Don't fight it. Your cock doesn't know the difference

imgur.com category @muppetgaybies

Living the fantasy..

gfycat.com category @dragoanz

Be the girl!

gfycat.com category @[deleted]

May you all be visited by the Sissy Slut Fairy

imgur.com category @taodie

My natural progression of becoming a sissy is reaching the next step...

imgur.com category @[deleted]

There's nothing more important than the support of a good friend

imgur.com category @ruskeleton

You should be so proud of the sissy you’ve become

gfycat.com category @jordan-smith123

Become the girl you were meant to be

gfycat.com category @MistressStella

Only BBC can turn me into the girl I truly am, and I worship it every night for hours on end! How many sissies here have submitted themselves totally to BBC?

gfycat.com category @sissyLoverJay

Just get naked with him and feel the tingle when you press your bodies together and put your arms around him

gfycat.com category @chaliceinlains

This is what the world wants from you!

gfycat.com category @PornMaker2048

I can't wait to take the final step!

imgur.com category @[deleted]

Find the job you love and you'll never work a single day

imgur.com category @muppetgaybies

It'll Be All The Sweeter

imgur.com category @RedCapss

Its the least you could do!(Sissy Sisterhood #3)

imgur.com category @sissy-discipline

Good thing I blew out the candles

imgur.com category @muppetgaybies

If you haven't done this before, now's the time...

gfycat.com category @MistressStella

You don't make the rules, you just follow them

gfycat.com category @random_sissy_sub

You just love hearing the sound of his balls clapping against your ass

gfycat.com category @captain_nsfw20

You love the taste, don't you sissy?

gfycat.com category @thesissygoddess

Cock on the mind

gfycat.com category @Sissy_Jessiexo

Who wants to do the stuffing this year?

imgur.com category @muppetgaybies

My first caption! Check out my blogspot and iFunny for more! All under my username

gfycat.com category @eljefetgcaptions

(First Caption Ever) Bullied

gfycat.com category @spook154

Fear the meek; you never notice the quiet ones [Straight][RESCUED][Wholesome][On the Phone][MtG Caption][Convoluted Narrative]

imgur.com category @BasedDoggoCaptions

An existing Japanese caption of Tokiko that I redid in English, using the translation from Danbooru. [pet] [gender-neutral][re-caption]

imgur.com category @Megamean10

Testing the waters... Then jumping in. r/Not_Cheating

imgur.com category @SCP_Guy

Smash The Patriarchy

gfycat.com category @CompileEros

Them's the rules (cheating)

imgur.com category @SCP_Guy