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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 Famous-Anteater-7934
2 days ago
Preview thumbnail for 24 #PalosHills - Hosting GH/Anon fun this weekend. Looking for masc, wm, mwm, bwc, READ. image
24 #PalosHills - Hosting GH/Anon fun this weekend. Looking for masc, wm, mwm, bwc, READ.
in PalosHills
to r/Chicagosissies by Famous-Anteater-7934
2 weeks 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 Famous-Anteater-7934
2 weeks 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 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 Famous-Anteater-7934
1 month 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 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
2 months 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
2 months 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
2 months 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 RVAbruh
2 months 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
2 months ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun Today (Tuesday) and upcoming Saturday, looking for masculine/beefy wm, mwm, bwc. Must be older! image
24 #PalosHills - hosting GH/Anon fun Today (Tuesday) and upcoming Saturday, looking for masculine/beefy wm, mwm, bwc. Must be older!
in PalosHills
to r/Chicagosissies by RVAbruh
2 months 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 RVAbruh
3 months 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 months ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun tomorrow/ Sat/ 08/17, looking for masculine/beefy wm, mwm, bwc. Must be older! image
24 #PalosHills - hosting GH/Anon fun tomorrow/ Sat/ 08/17, looking for masculine/beefy wm, mwm, bwc. Must be older!
in PalosHills
to r/Chicagosissies by RVAbruh
3 months 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 drdntoo
3 months ago
Preview thumbnail for Non-pass 26m CD looking for other CD/trans/fem to play & explore with. In chicago can travel image
Non-pass 26m CD looking for other CD/trans/fem to play & explore with. In chicago can travel
in Chicago, IL
to r/Chicagosissies by RVAbruh
3 months 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 months ago
Preview thumbnail for 24 #PalosHills - hosting GH/Anon fun tonorrow/Sunday, looking masculine/beefy for wm, mwm, bwc. Must be older! image
24 #PalosHills - hosting GH/Anon fun tonorrow/Sunday, looking masculine/beefy for wm, mwm, bwc. Must be older!
in PalosHills
to r/Chicagosissies by RVAbruh
4 months 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 RVAbruh
4 months ago
Preview thumbnail for 28 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
28 [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
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 RVAbruh
4 months ago
Preview thumbnail for 28 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
28 [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 RVAbruh
5 months ago
Preview thumbnail for 28 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
28 [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 RVAbruh
5 months ago
Preview thumbnail for 28 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
28 [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
5 months 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