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Chicago, IL
r/Chicagosissies
9,342 subscribers
Chicagoland, Northwest Indiana and Southern Wisconsin area Sissy / CD / transfemme personals. Request approval to post ads in our "about" menu.

Chicagosissies Moderators

Last updated: 04/06/2024
• MisterTrapDaddy added 3 years ago (also mods r/FeminizedForDaddy, r/FloridaFeminization)
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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New Top (24hr) Top (Week) Top (Month)
to r/Chicagosissies by Medical_Midnight3693
15 hours ago
[USA] #Chicago #Illinois - 40-Year-Old Dominant Seeking an Ongoing Connection.
Chicago
in USA
to r/Chicagosissies by Famous-Anteater-7934
4 days ago
Preview thumbnail for 24 [CD4M] #PalosHills - CD hosting GH/Anon fun this Saturday and Sunday. Read image
24 [CD4M] #PalosHills - CD hosting GH/Anon fun this Saturday and Sunday. Read
CD4M
in PalosHills
to r/Chicagosissies by MDvirgin
1 day ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop? image
28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by SissyLucyyyyyy
4 days ago
Preview thumbnail for 29 [S4A] #Itasca Sissy Slut Looking to be trained to be the perfect sissy slut and have fun with someone. All are welcome! image
29 [S4A] #Itasca Sissy Slut Looking to be trained to be the perfect sissy slut and have fun with someone. All are welcome!
in Itasca
to r/Chicagosissies by ApricotAdvanced9577
4 days ago
32 Married Alpha Dad seeks sissy for longterm play and feedings Dane county WI
Southern-Wisconsin
in Chicago, IL
to r/Chicagosissies by Pat_Jaminson
1 week ago
Preview thumbnail for 43 [S4A] #Naperville Sissy CD looking for someone discreet to play with my feet and more. image
43 [S4A] #Naperville Sissy CD looking for someone discreet to play with my feet and more.
Chicago-southwest-burbs
in Naperville, IL
to r/Chicagosissies by No_Check_4526
4 days ago
22 [M4T] shore drive desperate for a blow job and dominate me badmouthing , verbal abuse and pegging is also allowed (first time )
M4T Chicago
in Chicago, IL
to r/Chicagosissies by Minute-Cry-6274
1 day ago
Preview thumbnail for 19 [S4A] #Schaumburg 115 lb petite femboy looking for kinky muscular/fit dom to turn me into their personal sissy image
19 [S4A] #Schaumburg 115 lb petite femboy looking for kinky muscular/fit dom to turn me into their personal sissy
Chicago-northwest-burbs
in Schaumburg
to r/Chicagosissies by RVAbruh
1 week ago
Preview thumbnail for 29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun.
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
2 weeks ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop? image
28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by Famous-Anteater-7934
1 week ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun today. looking for masculine/beety wm, mwm, bwc only. READ image
24 #PalosHills - hosting GH/Anon fun today. looking for masculine/beety wm, mwm, bwc only. READ
in PalosHills
to r/Chicagosissies by chiguy0004
2 weeks ago
31 [M4T/Fem] Evanston - Gentleman looking for a fun and flirty transwoman or fem identifying person for a casual relationship with a strong connection.
M4T
in Chicago, IL
to r/Chicagosissies by okgas27
2 weeks ago
Preview thumbnail for 18 asian sissy femboy in Evanston north burbs looking for kinky fun with daddies and other sissies image
18 asian sissy femboy in Evanston north burbs looking for kinky fun with daddies and other sissies
in Chicago, IL
to r/Chicagosissies by Tarheel1524
3 weeks 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 RVAbruh
3 weeks ago
Preview thumbnail for 29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun.
T4M
in Chicago, IL
to r/Chicagosissies by Famous-Anteater-7934
3 weeks ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun Saturday and Sunday. Looking for masculine/beety wm, mwm, bwc. Must be older! READ image
24 #PalosHills - hosting GH/Anon fun Saturday and Sunday. Looking for masculine/beety wm, mwm, bwc. Must be older! READ
in PalosHills
to r/Chicagosissies by Famous-Anteater-7934
1 month ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun Saturday. looking for masculine/beety wm, mwm, bwc. Must be older! image
24 #PalosHills - hosting GH/Anon fun Saturday. looking for masculine/beety wm, mwm, bwc. Must be older!
in PalosHills
to r/Chicagosissies by MDvirgin
1 month ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop? image
28 [T4M] Chicago, Illinois - Want to try topping a sissy like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 month ago
Preview thumbnail for 29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun.
T4M
in Chicago, IL
to r/Chicagosissies by chiguy0004
1 month ago
31 [M4T/Fem] Evanston - Gentleman looking for a fun and flirty transwoman or fem identifying person for a casual relationship with a strong connection.
M4T
in Chicago, IL
to r/Chicagosissies by Famous-Anteater-7934
1 month ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun Saturday. looking for masculine/beety wm, mwm, bwc. Must be older! image
24 #PalosHills - hosting GH/Anon fun Saturday. looking for masculine/beety wm, mwm, bwc. Must be older!
in PalosHills
to r/Chicagosissies by Glass_Inevitable_197
1 month ago
31 [M4T/A] Joliet - White top/verse Dad LF T/Fem for tonight or some night next week ongoing or one time whatever’s clever super serious about making this happen
M4T M4A Chicago-southwest-burbs
in Chicago, IL
to r/Chicagosissies by Minute-Cry-6274
1 day ago
Preview thumbnail for 19 [S4A] #Schaumburg 115 lb petite femboy looking for kinky muscular/fit dom to turn me into their personal sissy bitch image
19 [S4A] #Schaumburg 115 lb petite femboy looking for kinky muscular/fit dom to turn me into their personal sissy bitch
Chicago-northwest-burbs
in Schaumburg
to r/Chicagosissies by Fidletwine
1 month ago
Preview thumbnail for 20 y/o Wisconsin Madison submissive, sissy looking for female owner- irl only image
20 y/o Wisconsin Madison submissive, sissy looking for female owner- irl only
in Madison, WI
to r/Chicagosissies by RVAbruh
1 month ago
Preview thumbnail for 29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
29 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun.
T4M
in Chicago, IL