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r/sissydresses

1,843 subscribers
Show off your sissy outfits, bonus points if you're wearing them! Although it's called sissy dresses, you can post any outfit you want as long as it's sissy related. We want to see those puff ball sleeves, pretty layered petticoats, satin dresses, and you being the prettiest little sissy you can be.

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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Prissy Sissy Sissy Slut Little Sissy Sissy Maid
New Top (24hr) Top (Week) Top (Month)
to r/sissydresses by SissySuki
4 weeks ago
Preview thumbnail for My favourite outfit of 2024. image
My favourite outfit of 2024.
Prissy Sissy
to r/sissydresses by SissySuki
4 weeks ago
Preview thumbnail for My favourite colour! image
My favourite colour!
Prissy Sissy
to r/sissydresses by SissySuki
1 month ago
Preview thumbnail for Pretty in pink! image
Pretty in pink!
Prissy Sissy
to r/sissydresses by SissySuki
1 month ago
Preview thumbnail for Not my usual colour…. image
Not my usual colour….
Prissy Sissy
to r/sissydresses by SissySuki
1 month ago
Preview thumbnail for This is my Maids Dress. image
This is my Maids Dress.
Sissy Maid
to r/sissydresses by SissySuki
1 month ago
Preview thumbnail for One of my favourite dresses. image
One of my favourite dresses.
Prissy Sissy
to r/sissydresses by Background-Elk-8155
5 months ago
Preview thumbnail for I got this new satin rumper yesterday and I love it 😍 image
I got this new satin rumper yesterday and I love it 😍
to r/sissydresses by Background-Elk-8155
5 months ago
Preview thumbnail for Who likes my new dress and boobs image
Who likes my new dress and boobs
Little Sissy
to r/sissydresses by jacquelinesissy
3 months ago
Preview thumbnail for Well, THAT Was Embarrassing! Windy Day Public Upskirt. image
Well, THAT Was Embarrassing! Windy Day Public Upskirt.
Sissy Maid
to r/sissydresses by Background-Elk-8155
5 months ago
Preview thumbnail for I think the dress looks so nice image
I think the dress looks so nice
to r/sissydresses by Background-Elk-8155
5 months ago
Preview thumbnail for I love the Print on these panties image
I love the Print on these panties
to r/sissydresses by jacquelinesissy
3 months ago
Preview thumbnail for Wearing My Pink Satin Sissy Maid Outfit to Get My QoS "Sissy Slut" Tattoo image
Wearing My Pink Satin Sissy Maid Outfit to Get My QoS "Sissy Slut" Tattoo
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Let's talk about how the Sissy kink can effect relationships....
to r/sissydresses by Bullys_n_Barbeez
1 year ago
I want to lock a cock, shrink a cock, abuse a cock, turn someone into a girl, and I want to find a new cuckold...
to r/sissydresses by Bullys_n_Barbeez
1 year ago
I want to lock a cock, shrink a cock, abuse a cock, turn someone into a girl, and I want to find a new cuckold...
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Being single makes sissy play easier but what about the closeted married sissies??
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Staying in a sissy mindset....
to r/sissydresses by Bullys_n_Barbeez
1 year ago
DISCREET Sissy Training
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Sabrina's Secret Sissy Society
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Sissy Roll Call
to r/sissydresses by Bullys_n_Barbeez
1 year ago
How many of those things would you let me do to you?...
to r/sissydresses by Bullys_n_Barbeez
1 year ago
The holidays are here that means it's time for you to be a complete ho ho ho ho! 🎅
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Sissies over 40....
to r/sissydresses by Bullys_n_Barbeez
1 year ago
Stop just watching from the sidelines......
to r/sissydresses by _Vortex_thb
1 year ago
Preview thumbnail for Black or white? image
Black or white?