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r/sissyguide

69,719 subscribers

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

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Challenge Me Feminized Reveal Unapproved Source Plugged Caged Sissy Slut Ass Up, Face Down! Open DMs Sissy Caption watch Femboy Bimbo 👄
Filtering for posts by u/Sissy_HollyQuinn
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to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Looking for someone femme that motivates me to go deeper down the sissy rabbit hole by positive rationalization. image
Looking for someone femme that motivates me to go deeper down the sissy rabbit hole by positive rationalization.
Challenge Me
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Love seeing my progress made to becoming a perfect sissy bimbo. Bois definitely make better girls. image
Love seeing my progress made to becoming a perfect sissy bimbo. Bois definitely make better girls.
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This sissy needs some sissy/trans pee play inspiration image
This sissy needs some sissy/trans pee play inspiration
Challenge Me
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This sissy is curious about pee play. Help push me over the edge. image
This sissy is curious about pee play. Help push me over the edge.
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for April Fools, Step-bro! image
April Fools, Step-bro!
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for 😍YOU'RE A SISSY😍 image
😍YOU'RE A SISSY😍
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This sissy desperately needs a mommy/daddy to force her feminization. image
This sissy desperately needs a mommy/daddy to force her feminization.
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This sissy needs a mommy to force her feminization. image
This sissy needs a mommy to force her feminization.
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for One order of Femboy Bulge with a side of special white sauce cumming right up! image
One order of Femboy Bulge with a side of special white sauce cumming right up!
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for It isn't gay if you are the girl image
It isn't gay if you are the girl
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for I am so close to tipping over the edge and becoming a fulltime sissy. I just need that last piece of motivation. image
I am so close to tipping over the edge and becoming a fulltime sissy. I just need that last piece of motivation.
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Oh no! I would hate it if a daddy/mommy tried to sissify me even more! image
Oh no! I would hate it if a daddy/mommy tried to sissify me even more!
Plugged
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for I am still straight though, right? image
I am still straight though, right?
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for The missing piece was found. image
The missing piece was found.
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for This has always been you. image
This has always been you.
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Being straight is so vanilla! image
Being straight is so vanilla!
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Bois make better girls <3 image
Bois make better girls <3
Sissy Caption
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Hey babes! What poses do you want to see me in? 💋 image
Hey babes! What poses do you want to see me in? 💋
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for I would love to be the next caption model for all aspiring sissies! ❤️ image
I would love to be the next caption model for all aspiring sissies! ❤️
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for I want to be your lockscreen! image
I want to be your lockscreen!
Challenge Me
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Hi, I am Holly. I am here for the sissy slut interview. image
Hi, I am Holly. I am here for the sissy slut interview.
Feminized
to r/sissyguide by Sissy_HollyQuinn
5 months ago
Preview thumbnail for Mommy finally got her milkers! No turning back now! Only way is forward and on my knees. 🍆💦🤤 image
Mommy finally got her milkers! No turning back now! Only way is forward and on my knees. 🍆💦🤤
Sissy Caption