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r/ChicagoCrossdressers

1,263 subscribers
Chicagoland, Northwest Indiana and Southern Wisconsin crossdresser personals. Please read the rules before posting!

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 Chicago-north-burbs Southern Wisconsin Chicago-northwest-burbs Chicago-southwest-burbs Chicago-west-burbs Chicago-south-burbs
New Top (24hr) Top (Week) Top (Month)
to r/ChicagoCrossdressers by Boredbro00
1 month ago
30 m looking for fun
to r/ChicagoCrossdressers by roxierose1993
2 months ago
Preview thumbnail for Hey there🌹 image
Hey there🌹
to r/ChicagoCrossdressers by Playful-Radish3599
3 months ago
34M4A
M4A Chicago-south-burbs
to r/ChicagoCrossdressers by roxierose1993
2 months ago
Preview thumbnail for South suburbs looking for another cd image
South suburbs looking for another cd
to r/ChicagoCrossdressers by markymark4692
3 months ago
Anyone into a cute plus-size sissy with a big belly and a little.....52 WM
to r/ChicagoCrossdressers by mc_mac2
4 months ago
29m top for a sissy crossdresser
to r/ChicagoCrossdressers by Fit_Ability7908
4 months ago
M4m Looking for a cross dresser
M4M
to r/ChicagoCrossdressers by Mandabear88
4 months ago
36/cd looking for chat :)
Chicago-west-burbs
to r/ChicagoCrossdressers by CardGroundbreaking28
4 months ago
37M, I want to go down on a crossdresser so bad
to r/ChicagoCrossdressers by SissyPlace4u
5 months ago
47m Looking for a secret crossdresser
to r/ChicagoCrossdressers by FeelThe_Kavorka
5 months ago
Discreet Black 30M seeking crossdresser for FWB
to r/ChicagoCrossdressers by CardGroundbreaking28
6 months ago
37M on my knees, looking for a crossdresser
to r/ChicagoCrossdressers by SissyCD4Roleplay
7 months ago
Preview thumbnail for 35 SW Burb sissy 4 hung Alpha. Who's up late and wants to walk me around like a cute little trophy pet image
35 SW Burb sissy 4 hung Alpha. Who's up late and wants to walk me around like a cute little trophy pet
Chicago-southwest-burbs
to r/ChicagoCrossdressers by rawdub
5 months ago
43, south side burbs, sissy, can't host. looking for my fellow sissies, trans, cd
to r/ChicagoCrossdressers by highdepths25
7 months ago
25M. Seeking a long term relationship with a fem bottom
to r/ChicagoCrossdressers by roxierose1993
2 months ago
Preview thumbnail for New here image
New here
to r/ChicagoCrossdressers by AdLiMKE
11 months ago
Saturday Night
Southern Wisconsin
to r/ChicagoCrossdressers by KristaCDOP
11 months ago
Preview thumbnail for Hiya! 54 sissy/ cd in Chicago area image
Hiya! 54 sissy/ cd in Chicago area
to r/ChicagoCrossdressers by KristaCDOP
11 months ago
Hiya!!
to r/ChicagoCrossdressers by CardGroundbreaking28
11 months ago
37M looking for crossdressing dominatrix in Chicago.
in Chicago, IL
to r/ChicagoCrossdressers by CardGroundbreaking28
11 months ago
37M looking for a dominatrix crossdresser in Illinois
in Illinois
to r/ChicagoCrossdressers by daddyerotic
1 year ago
[50s] [M4A] Daddy Seeking A Hookup For Chicago Fan Expo
M4A
in Chicago, IL
to r/ChicagoCrossdressers by LoosieGoosi
1 year ago
36 [M4M] Chubby Crossdresser looking for a Top.
M4M
to r/ChicagoCrossdressers by LoosieGoosi
1 year ago
[36yo] [M4M] Chubby Crossdresser looking for a Top.
M4M
to r/ChicagoCrossdressers by Maxlevel23
1 year ago
24 [M4M] Chicago/Anywhere - Any fem bottoms looking for a relationship?
M4M Chicago
in Chicago, IL