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Chicago, IL

r/Chicagor4rxxx

11,855 subscribers
New Top (24hr) Top (Week) Top (Month)
to r/Chicagor4rxxx by tamalane773
1 year ago
34 [T4M] #Ravenswood - Pretty, passable girl seeks hot guy to service
T4M
in Ravenswood
to r/Chicagor4rxxx 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/Chicagor4rxxx by BasicBang
1 year 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/Chicagor4rxxx by MDvirgin
1 year ago
Preview thumbnail for 28 [T4M] #WestLoop - Want to try topping a cross-dresser like me? image
28 [T4M] #WestLoop - Want to try topping a cross-dresser like me?
T4M
in westloop
to r/Chicagor4rxxx by tgirlchick
1 year ago
Preview thumbnail for 31 [t4m] #Antioch - post op trans chick seeking a few dudes to tag team me with my bf image
31 [t4m] #Antioch - post op trans chick seeking a few dudes to tag team me with my bf
T4M
in Antioch
to r/Chicagor4rxxx by tamalane773
1 year ago
34 [T4M] #Ravenswood - Pretty, passable girl seeks hot guy to service
T4M
in Ravenswood
to r/Chicagor4rxxx 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/Chicagor4rxxx by BasicBang
1 year 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/Chicagor4rxxx by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] #WestLoop - Want to try topping a cross-dresser like me? image
26 [T4M] #WestLoop - Want to try topping a cross-dresser like me?
T4M
in westloop
to r/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL
to r/Chicagor4rxxx by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] #WestLoop - Want to try topping a cross-dresser like me? image
26 [T4M] #WestLoop - Want to try topping a cross-dresser like me?
T4M
in westloop
to r/Chicagor4rxxx 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/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL
to r/Chicagor4rxxx 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/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL
to r/Chicagor4rxxx by tgirlchick
1 year ago
Preview thumbnail for 35 [t4m] #nwburbs - eat my 🐱 till I 💦 on your face! image
35 [t4m] #nwburbs - eat my 🐱 till I 💦 on your face!
T4M
in NWBurbs
to r/Chicagor4rxxx by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] #WestLoop - Want to try topping a cross-dresser like me? image
26 [T4M] #WestLoop - Want to try topping a cross-dresser like me?
T4M
in westloop
to r/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL
to r/Chicagor4rxxx by Playtimetvgurl
1 year ago
26 [T4M] #Lakeview - Young Latina trans Gurl hosting dom top studs
T4M
in Los Angeles, CA
to r/Chicagor4rxxx by xXweedslut420Xx
1 year ago
32 [T4A] #Humboldt Park - Deliriously horny and need someone to fuck me until i scream
T4A
in Humboldt
to r/Chicagor4rxxx 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/Chicagor4rxxx by Playtimetvgurl
1 year ago
26 [T4M] #Lakeview - Sexy Latina Trans looking to host fit, dom top/vers guys (pics in profile)
T4M
in Los Angeles, CA
to r/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL
to r/Chicagor4rxxx 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/Chicagor4rxxx by BasicBang
1 year ago
Preview thumbnail for 28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop. image
28 [T4M] Chicago, Illinois - Cross-dressing sissy looking to get naughty in West Loop.
T4M
in Chicago, IL