r/SissyUpskirt
15,530 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

SissyUpskirt Moderators

Last updated: 04/21/2024
• StrongSuspect4913 added 1 year ago (also mods 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.
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Like what you see? Oops, I forgot panties True upskirt What are you doing down there?
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Preview thumbnail for Tell me Iā€™m beautiful and make me feel loved while you enter me image
in r/SissyUpskirt
Tell me Iā€™m beautiful and make me feel loved while you enter me
Like what you see?
Preview thumbnail for Want to see whatā€™s underneath? image
in r/SissyUpskirt
Want to see whatā€™s underneath?
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Preview thumbnail for Whatā€™s up? šŸ˜ image
in r/SissyUpskirt
Whatā€™s up? šŸ˜
True upskirt
Preview thumbnail for Do you like these epics of my new skirt I sent to a guy on Grindr? image
in r/SissyUpskirt
Do you like these epics of my new skirt I sent to a guy on Grindr?
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Preview thumbnail for Fuck Me Friday image
in r/SissyUpskirt
Fuck Me Friday
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Preview thumbnail for Lick my toes, eat my ass, and FUCK me šŸ«¦ image
in r/SissyUpskirt
Lick my toes, eat my ass, and FUCK me šŸ«¦
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Preview thumbnail for Up the front or the back? image
in r/SissyUpskirt
Up the front or the back?
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Preview thumbnail for [OC]šŸ˜ˆ image
in r/SissyUpskirt
[OC]šŸ˜ˆ
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Preview thumbnail for Super Slutty Sissy Upskirt šŸ’• image
in r/SissyUpskirt
Super Slutty Sissy Upskirt šŸ’•
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Preview thumbnail for Fishnet Fun image
in r/SissyUpskirt
Fishnet Fun
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Preview thumbnail for Freshly Shaved Friday šŸŖ’ image
in r/SissyUpskirt
Freshly Shaved Friday šŸŖ’
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Preview thumbnail for Freshly Shaved Friday šŸŖ’ image
in r/SissyUpskirt
Freshly Shaved Friday šŸŖ’
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Preview thumbnail for Breed Me? image
in r/SissyUpskirt
Breed Me?
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Preview thumbnail for Craving my legs to be spread šŸ„µ image
in r/SissyUpskirt
Craving my legs to be spread šŸ„µ
True upskirt
Preview thumbnail for I love šŸ’™ image
in r/SissyUpskirt
I love šŸ’™
What are you doing down there?
Preview thumbnail for At least itā€™s cute even tho itā€™s useless image
in r/SissyUpskirt
At least itā€™s cute even tho itā€™s useless
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Preview thumbnail for My favorite skirt for easy access! image
in r/SissyUpskirt
My favorite skirt for easy access!
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Preview thumbnail for Only thing that's missing is a throbbing cock balls deep inside my tight ass, filling me up with hot cum šŸ„µšŸ˜ˆ image
in r/SissyUpskirt
Only thing that's missing is a throbbing cock balls deep inside my tight ass, filling me up with hot cum šŸ„µšŸ˜ˆ
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Preview thumbnail for Strawberry sundae šŸ“šŸ˜ image
in r/SissyUpskirt
Strawberry sundae šŸ“šŸ˜
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Preview thumbnail for I hope everyone is having a great Saturday ā˜ŗļø image
in r/SissyUpskirt
I hope everyone is having a great Saturday ā˜ŗļø
True upskirt
Preview thumbnail for How I look? image
in r/SissyUpskirt
How I look?
True upskirt
Preview thumbnail for Aren't these panties just sooo cuuttee! image
in r/SissyUpskirt
Aren't these panties just sooo cuuttee!
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Preview thumbnail for Saw a guy upskirting me on the subway yesterday >< do you think he will enjoy the view? image
in r/SissyUpskirt
Saw a guy upskirting me on the subway yesterday >< do you think he will enjoy the view?
Like what you see?
Preview thumbnail for What are you going to suck first? image
in r/SissyUpskirt
What are you going to suck first?
Oops, I forgot panties
Preview thumbnail for I said take me to a club! image
in r/SissyUpskirt
I said take me to a club!
What are you doing down there?