Coming soon - Get a detailed view of why an account is flagged as spam!
view details
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.

Browse by flair

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 MDvirgin
3 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
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 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 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 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 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
5 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
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 RVAbruh
6 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 alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
6 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 alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hotty looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by EnjoyLonelySkies
6 months ago
Preview thumbnail for 34 [T4R] - Transfemme Sub on the Northside Looking for Some Company This Weekend image
34 [T4R] - Transfemme Sub on the Northside Looking for Some Company This Weekend
T4R
in Chicago, IL
to r/Chicagosissies by alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hottie looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hottie looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
6 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
6 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 alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hotties looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hotties looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans hottie looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans hottie looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
7 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
7 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
7 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 MDvirgin
7 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
7 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