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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 RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by sissyaznCDmdwst
1 year ago
28 [T4M] #chicago - Fem passable Asian sissy CDer needs a breeding and creampie
T4M Chicago
in Chicago, IL
to r/Chicagosissies by Over8inchesplease
1 year ago
Preview thumbnail for 25 [T4M] Petite Latin size queen seeking the biggest ( st8 of bi men to the front) image
25 [T4M] Petite Latin size queen seeking the biggest ( st8 of bi men to the front)
T4M Chicago
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sisst looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
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 Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Ok_today2827
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by ATLmwmCD
1 year ago
Preview thumbnail for 38 [t4m] #oak brook - CD looking to serve can travel or host in west burbs with fake tits image
38 [t4m] #oak brook - CD looking to serve can travel or host in west burbs with fake tits
T4M Chicago-west-burbs
in oak
to r/Chicagosissies by EmotionPlastic3411
1 year ago
25 T4M MOUNT PROSPECT long haired, shaved face Mia Khalifa replica. Looking to get my head grabbed and throat fucked by BBC. BBC only. You must be into rough play and must be into a lot of spit because I have a sloppy mouth. BLACK ONLY. dm with a picture and I’ll send a face pic back.
T4M Chicago-northwest-burbs
in Chicago, IL
to r/Chicagosissies by Ok_today2827
1 year ago
23 [T4M] #Portage Park - Sisst looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by MatriarchMel
1 year ago
Preview thumbnail for T4m joliet Sweet submissive sissy looking for hung verbal top to dominate my ass image
T4m joliet Sweet submissive sissy looking for hung verbal top to dominate my ass
T4M
in Chicago, IL
to r/Chicagosissies by Ok_today2827
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by sillygreencup
1 year ago
27 [T4M] #Lakeview - Femboy looking for someone to play with my hole or other femboys
T4M Chicago
in Los Angeles, CA
to r/Chicagosissies by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by EmotionPlastic3411
1 year ago
25 T4M MOUNT PROSPECT long haired, shaved face Mia Khalifa replica. Looking to get my head grabbed and throat fucked by BBC. BBC only. You must be into rough play and must be into a lot of spit because I have a sloppy mouth. BLACK ONLY. dm with a picture and I’ll send a face pic back.
T4M Chicago-northwest-burbs
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by Ok_today2827
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Ok_today2827
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL