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r/SissyUpskirt

16,170 subscribers
A place for sissies, traps, crossdressers and trans girls to share their beautiful upskirts

Note: ABSOLUTELY NO MISTRESS POSTS, ANY WILL BE REMOVED AND THE POSTER BANNED!

Subreddit icon by u/Sissy_in_denial795

Moderators

Updated Apr 21, 2024
u/StrongSuspect4913 Active
Added 2 years ago
Also moderates: r/Sissies, r/FapDeciders, r/Sissy, r/ProlapseVille, r/Sissytasks, and 1 more...

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

Browse by flair

True upskirt Like what you see? Oops, I forgot panties What are you doing down there?
New Top (24hr) Top (Week) Top (Month)
to r/SissyUpskirt by BJBambi
1 hour ago
Preview thumbnail for My little clitty image
My little clitty
Like what you see?
to r/SissyUpskirt by Kaleidoscope117
4 hours ago
Preview thumbnail for hehe mwah image
hehe mwah
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
4 days ago
Preview thumbnail for Hiii image
Hiii
Oops, I forgot panties
to r/SissyUpskirt by BiFunInTheSun
4 days ago
Preview thumbnail for Peek a boo 👻 image
Peek a boo 👻
True upskirt
to r/SissyUpskirt by sebincognitoxxx
2 weeks ago
Preview thumbnail for Why don't u kiss it? image
Why don't u kiss it?
What are you doing down there?
to r/SissyUpskirt by BiFunInTheSun
4 days ago
Preview thumbnail for I can’t help but slowly tease you a little before you get the full show 😘 image
I can’t help but slowly tease you a little before you get the full show 😘
Like what you see?
to r/SissyUpskirt by Goon2theMoon2
3 weeks ago
Preview thumbnail for New Sissy image
New Sissy
Like what you see?
to r/SissyUpskirt by Switch_us
2 weeks ago
Preview thumbnail for I think my panties are in the way image
I think my panties are in the way
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
4 weeks ago
Preview thumbnail for Something so sexy about being a sissy image
Something so sexy about being a sissy
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Inch by inch until you’re up my skirt 🤭 image
Inch by inch until you’re up my skirt 🤭
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Sexy, Soft, Shaved Legs in Lingerie and Sultry Stilletos image
Sexy, Soft, Shaved Legs in Lingerie and Sultry Stilletos
Like what you see?
to r/SissyUpskirt by Sad_Secretary6366
1 month ago
Preview thumbnail for Sir, does my bum look big in this? image
Sir, does my bum look big in this?
Oops, I forgot panties
to r/SissyUpskirt by sossysissyy
1 month ago
Preview thumbnail for Nothing up my skirt.....oh wait image
Nothing up my skirt.....oh wait
Oops, I forgot panties
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for I love dresses and skirts image
I love dresses and skirts
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Tell me I’m beautiful and make me feel loved while you enter me image
Tell me I’m beautiful and make me feel loved while you enter me
Like what you see?
to r/SissyUpskirt by AprilRose2342
1 month ago
Preview thumbnail for Want to see what’s underneath? image
Want to see what’s underneath?
Like what you see?
to r/SissyUpskirt by cosmicframework
3 weeks ago
Preview thumbnail for Oooo you're making me twitch down there 😋🍆 image
Oooo you're making me twitch down there 😋🍆
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for What’s up? 😏 image
What’s up? 😏
True upskirt
to r/SissyUpskirt by cosmicframework
3 weeks ago
Preview thumbnail for Is that you down there making me twitch? 😳🍆 image
Is that you down there making me twitch? 😳🍆
Like what you see?
to r/SissyUpskirt by cosmicframework
3 weeks ago
Preview thumbnail for Does this count as an upskirt? Well while you are down there .... 🤭 image
Does this count as an upskirt? Well while you are down there .... 🤭
What are you doing down there?
to r/SissyUpskirt by sub_thick_cock
1 month ago
Preview thumbnail for Do you like these epics of my new skirt I sent to a guy on Grindr? image
Do you like these epics of my new skirt I sent to a guy on Grindr?
Like what you see?
to r/SissyUpskirt by Quicksilver188
1 month ago
Preview thumbnail for POV you ask me to sit on your face image
POV you ask me to sit on your face
True upskirt
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Fuck Me Friday image
Fuck Me Friday
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Lick my toes, eat my ass, and FUCK me 🫦 image
Lick my toes, eat my ass, and FUCK me 🫦
Like what you see?
to r/SissyUpskirt by BiFunInTheSun
1 month ago
Preview thumbnail for Up the front or the back? image
Up the front or the back?
Like what you see?