Would you like to see your picture captioned and posted in a ClubSissy Captions Gallery? Post your pics here to be captioned, and let the artists work their magic!

Photos posted here will retain their original size, up to 1600x1600 pixels, for benefit of captioning. By posting your photo in this gallery, you grant permission for your photo to be modified and/or captioned and posted in the ClubSissy Captions Gallery. You still retain full rights to your photo, and captioned works based on your photo may not be posted outside of ClubSissy without your express permission.

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goth/emo sissy (8)

humiliating names, interracial related, cum related and oral related stuff use your imagination :D

Oct 02, 2016

Sissy Maid Sarah (4)

SPH, sissy humiliation, bisexual suggestions & anything relating to being a maid

Oct 01, 2016

Satin cd (9)

Satin panty ass...huge cock...Caption me pls!!

Oct 01, 2016

This Sluts name is Cody (5)

Loves: Facials, Gangbangs, men and TS, getting fucked, bukkake, deepthroat. Please no chastity.

Sep 30, 2016

sissy bryanna (43)

Forced fem humiliation

Sep 30, 2016

My boi pussy (4)

Just wanna know what y'all think of my pussy.

Sep 30, 2016

Sissy jessica (3)

Humiliation

Sep 30, 2016

My sissy self (4)

Go ahead, impress me ;)

Sep 30, 2016

Dreaming of Cock! (6)

Cock drunk and craving a big cock gagging me and penetrating my ass filling it deep and hard.

Sep 27, 2016

Ashley's Caption Me!!!!! (1)

Wanna see what you can come up with.

Sep 27, 2016


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