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Chicago, IL

r/Chicagosissies

9,342 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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to r/Chicagosissies by Tarheel1524
1 month ago
Preview thumbnail for 29 #Logan Square - Discreet bubble butt femboy hosting hung/dominant guy today image
29 #Logan Square - Discreet bubble butt femboy hosting hung/dominant guy today
in Logan
to r/Chicagosissies by LittleKali18
2 months ago
Preview thumbnail for 18 - #Berwyn Femboy sissy looking for a consistent older dom that can host nearby and wants to help make videos while we do it, plz send location, pics and age image
18 - #Berwyn Femboy sissy looking for a consistent older dom that can host nearby and wants to help make videos while we do it, plz send location, pics and age
in Berwyn
to r/Chicagosissies by bttmalex420
1 month ago
Preview thumbnail for 18 M Latino looking for Older Daddys who want to breed a femboy hole (SouthWest Chicago) image
18 M Latino looking for Older Daddys who want to breed a femboy hole (SouthWest Chicago)
in Chicago, IL
to r/Chicagosissies by bttmalex420
4 months ago
Preview thumbnail for 18 femboy looking for horny daddys/fwb/older to play with my tight sissy hole image
18 femboy looking for horny daddys/fwb/older to play with my tight sissy hole
in Chicago, IL
to r/Chicagosissies by Neminimi
9 months ago
18 Near North| femboy/transgirl looking for hookups w/ anyone, especially other sissy and trans peeps :3
in Chicago, IL
to r/Chicagosissies by nekomaid2
9 months ago
19 femboy from the burbs closer to Naperville looking for fwb or just friends
in Chicago, IL
to r/Chicagosissies by nekomaid2
9 months ago
Preview thumbnail for M19 Femboy Aurora/Naper wondering if any femboy and or sissy may be able to help me learn a new skill of sucking dick image
M19 Femboy Aurora/Naper wondering if any femboy and or sissy may be able to help me learn a new skill of sucking dick
M
in Chicago, IL
to r/Chicagosissies by chicagofemboy
9 months ago
Preview thumbnail for 24 CD hosting in Pilsen for no strings attached 🤤 let me give you sloppy deepthroat til you bust image
24 CD hosting in Pilsen for no strings attached 🤤 let me give you sloppy deepthroat til you bust
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24 [T4M] - hosting deepthroat in Pilsen 🤤 come fuck my face until you cum down my throat 😈 image
24 [T4M] - hosting deepthroat in Pilsen 🤤 come fuck my face until you cum down my throat 😈
T4M
in Chicago, IL
to r/Chicagosissies by dizzy4miles54
1 year ago
Preview thumbnail for 18M Anyone near berwyn wanna be my hookup tn? Dm me al’s and m pics and i’ll send back ;) image
18M Anyone near berwyn wanna be my hookup tn? Dm me al’s and m pics and i’ll send back ;)
in Chicago, IL
to r/Chicagosissies by Prudent-Breadfruit-2
1 year ago
Preview thumbnail for 23 Sissy/femboy looking for a muscular BWC Daddy Dom and/or other younger Phat Ass white bois/sissies to play with 😚 image
23 Sissy/femboy looking for a muscular BWC Daddy Dom and/or other younger Phat Ass white bois/sissies to play with 😚
in Chicago, IL
to r/Chicagosissies by Prudent-Breadfruit-2
1 year ago
Preview thumbnail for 23 younger bi(discreet) femboy(aspiring sissy) looking for an experienced and mature man to be my Daddy. image
23 younger bi(discreet) femboy(aspiring sissy) looking for an experienced and mature man to be my Daddy.
in Chicago, IL
to r/Chicagosissies by Fbluis131
1 year ago
Preview thumbnail for (20) Femboy. Looking for other femboys mostly but still open to all. I’m In North Chicago near Waukegan. image
(20) Femboy. Looking for other femboys mostly but still open to all. I’m In North Chicago near Waukegan.
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24 yo sissy needs to be used in Pilsen. hosting a NSA gloryhole 😋 come try me out image
24 yo sissy needs to be used in Pilsen. hosting a NSA gloryhole 😋 come try me out
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24 [T4M] - discrete trans Latina looking to deepthroat you in Pilsen tonight 🤤 image
24 [T4M] - discrete trans Latina looking to deepthroat you in Pilsen tonight 🤤
T4M
in Chicago, IL
to r/Chicagosissies by onikamarajstan01
1 year ago
Preview thumbnail for (21) Femboy looking to worship white boy ass and cock or trans in Chicago or north suburbs image
(21) Femboy looking to worship white boy ass and cock or trans in Chicago or north suburbs
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24[T4M] i want a masculine man to submit to me 😇 are you a straight guy curious to get your ass ate? 😈 want to be pegged? let me dominate you in the sheets 🥰 hosting in Pilsen, send a pic for my reply image
24[T4M] i want a masculine man to submit to me 😇 are you a straight guy curious to get your ass ate? 😈 want to be pegged? let me dominate you in the sheets 🥰 hosting in Pilsen, send a pic for my reply
T4M
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24 femboy in the Pilsen neighborhood. Can I suck on you and slide it in? 😈 send a pic for my response image
24 femboy in the Pilsen neighborhood. Can I suck on you and slide it in? 😈 send a pic for my response
in Chicago, IL
to r/Chicagosissies by SexualVoid9
3 months ago
19 West Chicago Femboy looking for somebody to hookup with don’t be scared btw open to anything
in Chicago, IL