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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.

Moderators

Updated Apr 6, 2024
u/MisterTrapDaddy Active
Added 3 years ago
Also moderates: 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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Chicago Northwest-Indiana Chicago-north-burbs Daddy Chicago-west-burbs Sissy Chicago-northwest-burbs Crossdresser Femboy Dom Chicago-southwest-burbs Male Femme Chicago-south-burbs Southern-Wisconsin Couple Bull Trans Seeking Feminization Genderfluid
New Top (24hr) Top (Week) Top (Month)
to r/Chicagosissies by Famous-Anteater-7934
12 hours ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun SAT-SUN looking for masculine/beety wm, mwm, bwc preferred. READ image
24 #PalosHills - hosting GH/Anon fun SAT-SUN looking for masculine/beety wm, mwm, bwc preferred. READ
in PalosHills
to r/Chicagosissies by omega300m
3 days ago
30 Schaumburg - Bicurious seeking to explore with a cute twink, fem, or sissy
in Chicago, IL
to r/Chicagosissies by SissyKiya
2 days ago
35 - Lombard - Sub Sissy looking for ongoing relationship/friendship with a Dom Daddy
in Chicago, IL
to r/Chicagosissies by Famous-Anteater-7934
5 days ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun Today. looking for masculine/beety wm, mwm, bwc preferred image
24 #PalosHills - hosting GH/Anon fun Today. looking for masculine/beety wm, mwm, bwc preferred
in PalosHills
to r/Chicagosissies by Connect-Air-3950
5 days ago
Preview thumbnail for 26 ~ Logan Square ~ Latin sissy looking to host a str8/curious guy that can toss me around tonight 😘 image
26 ~ Logan Square ~ Latin sissy looking to host a str8/curious guy that can toss me around tonight 😘
in Chicago, IL
to r/Chicagosissies by Connect-Air-3950
1 week ago
Preview thumbnail for (26) slutty & submissive big booty latin sissy hosting this weekend! Into dominant, masculine men 😘 image
(26) slutty & submissive big booty latin sissy hosting this weekend! Into dominant, masculine men 😘
in Chicago, IL
to r/Chicagosissies by Unique-Floor-1985
1 week ago
Preview thumbnail for 30yo femboy cd sub in search of gentle fem domme to worship and take my virgin ass image
30yo femboy cd sub in search of gentle fem domme to worship and take my virgin ass
in Chicago, IL
to r/Chicagosissies by Medical_Midnight3693
1 week ago
[USA] #Chicago #Illinois #IL 40-Year-Old Dominant Male Seeking Ongoing Dynamic M4T / M4CD / M4Femboy
Chicago
in USA
to r/Chicagosissies by Medical_Midnight3693
2 weeks ago
[USA] #Chicago #Illinois - 40-Year-Old Dominant Seeking an Ongoing Connection.
Chicago
in USA
to r/Chicagosissies by Famous-Anteater-7934
3 weeks 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 SissyLucyyyyyy
3 weeks 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
3 weeks 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
3 weeks 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
3 weeks 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
2 weeks 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 Famous-Anteater-7934
4 weeks 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
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 okgas27
1 month 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
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 Famous-Anteater-7934
1 month 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 NickytheQueen
5 days ago
Preview thumbnail for My name is Nicky and this is my first post here. Who wants to keep me company? (28T) image
My name is Nicky and this is my first post here. Who wants to keep me company? (28T)
Chicago-southwest-burbs
in Chicago, IL
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 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