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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
1 month 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 chicagopantyboi
3 months ago
Preview thumbnail for 49 [CD4M] north burbs CD looking to eagerly suck and bottom for a chubby Daddy image
49 [CD4M] north burbs CD looking to eagerly suck and bottom for a chubby Daddy
CD4M
in Chicago, IL
to r/Chicagosissies by Famous-Anteater-7934
4 months ago
Preview thumbnail for 23 [CD4M] #Willowbrook - Hosting and looking for older masculine man. Masked CD/anon. image
23 [CD4M] #Willowbrook - Hosting and looking for older masculine man. Masked CD/anon.
CD4M
in Willowbrook
to r/Chicagosissies by chicagopantyboi
5 months ago
Preview thumbnail for 49 [CD4M] horny sissy in panties and wanting to be slut trained and opened up by a patient and kind Daddy. Do you have what it takes? Chats open image
49 [CD4M] horny sissy in panties and wanting to be slut trained and opened up by a patient and kind Daddy. Do you have what it takes? Chats open
CD4M
in Chicago, IL
to r/Chicagosissies by ChiGuy7070
9 months ago
30 [CD4M] #WickerPark - Your Secret Friend. So you have a gf or a wife but you need that regular sexual attention.
CD4M
in Chicago, IL
to r/Chicagosissies by ChiGuy7070
10 months ago
30 [CD4M] #WickerPark - Your Secret Friend. So you have a gf or a wife but you need that regular sexual attention.
CD4M
in Chicago, IL
to r/Chicagosissies by ChiGuy7070
10 months ago
30 [CD4M] #WickerPark - Your Secret Friend. So you have a gf or a wife but you need that regular sexual attention.
CD4M
in Chicago, IL
to r/Chicagosissies by StrongConstant6702
10 months ago
Preview thumbnail for 25 [CD4M] Logan Square. Better than your girl. Who wants to play with me? Good vibes only 🍭 image
25 [CD4M] Logan Square. Better than your girl. Who wants to play with me? Good vibes only 🍭
CD4M
in Chicago, IL
to r/Chicagosissies by chicagopantyboi
11 months ago
50 nwburbs [CD4M] Sissy / CD looking to suck dick tonight or tomorrow morning to end the week right
CD4M
in Chicago, IL
to r/Chicagosissies by Here4cum38
11 months ago
Preview thumbnail for 38 [cd4m] #oakbrook - looking for some fun, newbie here looking for men seeking fun image
38 [cd4m] #oakbrook - looking for some fun, newbie here looking for men seeking fun
CD4M
in Oakbrook
to r/Chicagosissies by Sophia_Top_TS
11 months ago
[30] [Bartlett] [CD] - Sexy Sophia hosting today and looking to have some verse fun. Please be clean and respectful.
CD
in CD
to r/Chicagosissies by tgurl30080
1 year ago
Preview thumbnail for 35 [cd4m] #west burns - CD looking tomorrow and Tuesday for cock to service image
35 [cd4m] #west burns - CD looking tomorrow and Tuesday for cock to service
CD4M Chicago-west-burbs
in WEST
to r/Chicagosissies by CharmingTheme236
1 year ago
21 [cd4m] 5'7 130lbs twink looking to crossdress and be your slut (no experience)
CD4M
in Chicago, IL
to r/Chicagosissies by varlap1
1 year ago
Preview thumbnail for 26 [Willowbrook] [CD] Hosting today until tomorrow morning for Big c*ck, the sooner the better 😏 image
26 [Willowbrook] [CD] Hosting today until tomorrow morning for Big c*ck, the sooner the better 😏
CD
in CD
to r/Chicagosissies by varlap1
1 year ago
Preview thumbnail for 26 [Willowbrook] [CD] big booty crossdresser looking for any neglected cocks, for this week. Message me with your info😉 image
26 [Willowbrook] [CD] big booty crossdresser looking for any neglected cocks, for this week. Message me with your info😉
CD
in CD
to r/Chicagosissies by StrongConstant6702
1 year ago
Preview thumbnail for 25 [CD] Petite Latina 💋 Choose your girl 👀 Let me make your toes curl, eyes roll. I’ll keep your secret image
25 [CD] Petite Latina 💋 Choose your girl 👀 Let me make your toes curl, eyes roll. I’ll keep your secret
CD
in CD
to r/Chicagosissies by StrongConstant6702
1 year ago
Preview thumbnail for 25 [CD] Chicago IL - Step Sis-sy needs attention🍒 Kinky and ready to please your needs image
25 [CD] Chicago IL - Step Sis-sy needs attention🍒 Kinky and ready to please your needs
CD
in CD
to r/Chicagosissies by StrongConstant6702
1 year ago
Preview thumbnail for 25 [CD] Chicago IL, Petite Latina looking for straight/ curious man to have fun with. Better than your girl image
25 [CD] Chicago IL, Petite Latina looking for straight/ curious man to have fun with. Better than your girl
CD
in CD
to r/Chicagosissies by tgurl30080
1 year ago
35 [cd4m] #river north - CD looking tomorrow and Tuesday for cock to service
CD4M Chicago
in River
to r/Chicagosissies by CharmingTheme236
1 year ago
21 [cd4m] 5'7 130lbs twink looking to crossdress and your slut (no experience)
CD4M
in Chicago, IL
to r/Chicagosissies by Illtrythat83
1 year ago
31 - [CD4ALL] - sissy looking for another to play together - western suburbs
CD4A
in Chicago, IL