r/sissydressing

▲ 211 r/sissydressing+24 crossposts

Trying Blue Archive Kazusa cosplay

u/Shinen2022 — 5 hours ago

▲ 1.2k r/sissydressing+19 crossposts

u/AngelAvaa — 9 hours ago

▲ 16 r/sissydressing+2 crossposts

Hey❤️

u/Evaskye615 — 3 hours ago

▲ 349 r/sissydressing+10 crossposts

Playing with myself

u/justadream96 — 9 hours ago

▲ 20 r/sissydressing+8 crossposts

hiiii

u/Odd_Guess5490 — 4 hours ago

▲ 88 r/sissydressing+21 crossposts

is it too revealing? Will you stare at me if I wear like this ?

u/Extra_Dog_1959 — 8 hours ago

▲ 140 r/sissydressing+3 crossposts

Posing like a woman to pass as a woman 🥰✨️

u/DelilaBee — 10 hours ago

▲ 144 r/sissydressing+4 crossposts

Dig deep daddy

u/BIackBootay — 11 hours ago

▲ 25 r/sissydressing

Dressing up is fun but taking it off is better

u/CutieRaya — 8 hours ago

▲ 5 r/sissydressing

Which pose works better?

u/summerfun901 — 6 hours ago

▲ 8 r/sissydressing

Would you bring me home to meet your mom

u/Cassiehd — 8 hours ago

▲ 9 r/sissydressing

First time trying lingerie

u/Similar-Boot3077 — 6 hours ago

▲ 18 r/sissydressing+1 crossposts

Kinky playtime 😋

u/xxCandySarahPinkCD — 10 hours ago

▲ 20 r/sissydressing

my pronouns are thicc/asf hehe >.<

u/lilyrosereal — 10 hours ago

▲ 142 r/sissydressing+18 crossposts

I feel the prettiest when my girl dick is out

u/LovelyLitten — 17 hours ago

▲ 8 r/sissydressing+1 crossposts

This is just a phase right?

u/sissys3ut_77 — 9 hours ago

▲ 299 r/sissydressing+5 crossposts

My drag/crossdressing makeup - any tips?

Hi everyone

I'm really quite shy about showing my face, but i'm trying to be braver (lol). I've been crossdressing a long time, and I'm pretty happy with my makeup, but any tips would be nice

(p.s theres a good chance i'll freak out later and delete this..sorry in advance!

u/sissyjennyx2025 — 24 hours ago

▲ 164 r/sissydressing+21 crossposts

fertile and breedable btw :3

u/LovelyLitten — 19 hours ago

▲ 38 r/sissydressing+3 crossposts

Felt kinda cute ….

is pick my colour? Padded bra working overtime!

u/Sammid_12 — 18 hours ago

▲ 102 r/sissydressing+4 crossposts

Hey, I'm new here so please be nice:)

u/pathetic_whiteboiii — 23 hours ago