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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 RVAbruh
10 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 BasicBang
10 months ago
Preview thumbnail for 29 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
29 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
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
10 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 Dry-Crazy-2646
10 months ago
Preview thumbnail for 31 / CD / SE WI - Looking for other FEMS, CD, SISSIES for fun, play, dressing ! image
31 / CD / SE WI - Looking for other FEMS, CD, SISSIES for fun, play, dressing !
in Wisconsin
to r/Chicagosissies by MDvirgin
10 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 RVAbruh
10 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 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 MDvirgin
11 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 RVAbruh
11 months ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun. image
27 [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 Dry-Crazy-2646
11 months ago
Preview thumbnail for 31 / CD / SOUTH WISCONSIN - MY FIRST IMAGE POST! DMs are open for friends but i am seeking other Fems, CD, Sissy for dressing up together! image
31 / CD / SOUTH WISCONSIN - MY FIRST IMAGE POST! DMs are open for friends but i am seeking other Fems, CD, Sissy for dressing up together!
in Wisconsin
to r/Chicagosissies by RVAbruh
11 months ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by Here4cum38
11 months ago
38T andersonville - looking at 4p at Heart ‘O Chicago hotel for fun while visiting
in Chicago, IL
to r/Chicagosissies by MDvirgin
11 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 RVAbruh
11 months ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
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 MDvirgin
11 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 RVAbruh
11 months ago
Preview thumbnail for 27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop) image
27 [T4M] Chicago, IL - I'm looking to crossdress as a sissy for a guy and have some fun (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
1 year 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 MDvirgin
1 year 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 Ella_thesexdoll
5 months ago
Preview thumbnail for 26 Chicago (Wrigley) TF Sissy - I’m taking volunteers on who can take these off with their teeth. (please send bodypics/stats in your first message.) image
26 Chicago (Wrigley) TF Sissy - I’m taking volunteers on who can take these off with their teeth. (please send bodypics/stats in your first message.)
in Chicago, IL
to r/Chicagosissies by Secretcd123
1 year ago
Preview thumbnail for 30 [sissy for anything] #lincoln square looking for friendship, other sissies, and more! image
30 [sissy for anything] #lincoln square looking for friendship, other sissies, and more!
in sissy for anything
to r/Chicagosissies by Ella_thesexdoll
5 months ago
Preview thumbnail for 23 Chicago (Wrigley) TF Sissy - Who wants to play with the devil? Happy Halloween. image
23 Chicago (Wrigley) TF Sissy - Who wants to play with the devil? Happy Halloween.
in Chicago, IL
to r/Chicagosissies by MDvirgin
1 year 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 MDvirgin
1 year 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