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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
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 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 alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys - more pics in profile
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 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 RVAbruh
8 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
8 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
8 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
8 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 alexistransgurl
6 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys - more pics in profile image
26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
8 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
9 months ago
Preview thumbnail for 26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys this Monday- more pics in profile image
26 [T4M] OldTown - Latina Trans gurl looking to host dom, top guys this Monday- more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
9 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
9 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
9 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
9 months ago
24 [T4M] OldTown - 2 Latina Trans gurls looking to host hot, top guys - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
9 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
9 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
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 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 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 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