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Chicago, IL

r/Chicagosissies

9,342 subscribers

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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
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 BasicBang
6 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
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 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
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 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 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 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
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 Nvmeinu
8 months ago
40/Looking for a T/F /4 cd or m/⁴ CD to fill a CD. I'm a closet CD love to dress and look sexy you can use me any way you want no pain the bigger the better but anyone is ok with me have great oral skills suck at makeup just looking to dress up someone be real show up and let me drain you in me
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 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