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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 TS_Justicex
10 months ago
Preview thumbnail for 20 [T4M] #Rogers Park, 9 inch bbc and a bubblebutt lookin for tops and bottom image
20 [T4M] #Rogers Park, 9 inch bbc and a bubblebutt lookin for tops and bottom
T4M
in Rogers
to r/Chicagosissies by alexistransgurl
10 months ago
Preview thumbnail for 24 [T4M] OldTown - 2 Trans gurls looking to host hot, top studs - more pics in profile image
24 [T4M] OldTown - 2 Trans gurls looking to host hot, top studs - more pics in profile
T4M
in Chicago, IL
to r/Chicagosissies by TS_Justicex
10 months ago
Preview thumbnail for 20 [T4M] #Rogers Park, 9 inch bbc and a bubblebutt lookin for tops and bottom image
20 [T4M] #Rogers Park, 9 inch bbc and a bubblebutt lookin for tops and bottom
T4M
in Rogers
to r/Chicagosissies by alexistransgurl
10 months ago
Preview thumbnail for 26 [T4M] OldTown - 2 Trans gurls looking to host hot, hung top studs - pics in profile image
26 [T4M] OldTown - 2 Trans gurls looking to host hot, hung top studs - pics in profile
T4M
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 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 alexistransgurl
11 months ago
Preview thumbnail for 26 [T4M] OldTown - Trans Latina gurl looking to host hot, hung top studs - pics in profile image
26 [T4M] OldTown - Trans Latina gurl looking to host hot, hung top studs - pics in profile
T4M
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
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 alexistransgurl
11 months ago
Preview thumbnail for 26 [T4M] OldTown - Trans Latina gurl looking to host top studs - pics in profile image
26 [T4M] OldTown - Trans Latina gurl looking to host top studs - pics in profile
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 alexistransgurl
11 months ago
Preview thumbnail for 26 [T4M] OldTown - Trans Latina gurl looking to host top studs - pics in profile image
26 [T4M] OldTown - Trans Latina gurl looking to host top studs - pics in profile
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 alexistransgurl
11 months ago
Preview thumbnail for 26 [T4M] Old Town - Latina trans gurl looking to host top/vers studs at my place image
26 [T4M] Old Town - Latina trans gurl looking to host top/vers studs at my place
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 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 Here4cum38
11 months ago
Preview thumbnail for 38 [t4m] looking for some fun with local guys. Here for work this week. Here until Friday. image
38 [t4m] looking for some fun with local guys. Here for work this week. Here until Friday.
T4M
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year 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 RVAbruh
1 year 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 ATLmwmCD
1 year ago
Preview thumbnail for 38 [t4m] #rivernorth - here for work again and looking for a good time with discreet guy image
38 [t4m] #rivernorth - here for work again and looking for a good time with discreet guy
T4M Chicago
in RiverNorth
to r/Chicagosissies by RVAbruh
1 year 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 RVAbruh
1 year 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