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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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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 MatriarchMel
1 year ago
Preview thumbnail for T4M 28 joliet sissy looking for hung daddy to put me in my place. Love verbal tops that take control. image
T4M 28 joliet sissy looking for hung daddy to put me in my place. Love verbal tops that take control.
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 MatriarchMel
1 year ago
Preview thumbnail for 28 [T4M] Joliet Illinois looking for daddy dick. I'm a submissive sissy bottom looking to be put in her place. I can host as well as travel. I'm slutty and obedient all the way. image
28 [T4M] Joliet Illinois looking for daddy dick. I'm a submissive sissy bottom looking to be put in her place. I can host as well as travel. I'm slutty and obedient all the way.
T4M
in Joliet, IL
to r/Chicagosissies by Chi-HeadQueen
1 year ago
25 [T4M] #LincolnSquare - Sexy fem Latina seeking h u n g guys… any morning wood?
T4M Chicago
in LincolnSquare
to r/Chicagosissies by amandathroats
1 year ago
Preview thumbnail for 31 [T4M] Southwest Burbs - Orally talented CD cutie with a booty looking to worship image
31 [T4M] Southwest Burbs - Orally talented CD cutie with a booty looking to worship
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 MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by BasicBang
1 year ago
28 [T4M] Chicago, Illinois - Do you want to pound a cross-dresser in 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 Chi-HeadQueen
1 year ago
25 [T4M] #Rogers Park - Feminine, discreet and clean seeking a manly man to please
T4M Chicago-north-burbs
in Rogers
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 MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by BasicBang
1 year ago
28 [T4M] Chicago, Illinois - Do you want to pound a cross-dresser in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24 [T4M] - discrete trans Latina looking to deepthroat you in Pilsen tonight 🤤 image
24 [T4M] - discrete trans Latina looking to deepthroat you in Pilsen tonight 🤤
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 MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in 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 MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by No_Worldliness2570
1 year ago
Preview thumbnail for 32 [T4M] Mundelein. I’m bottom verse seeking top verse. Love to party and get freaky. Hun with pics and we’ll take it from there. image
32 [T4M] Mundelein. I’m bottom verse seeking top verse. Love to party and get freaky. Hun with pics and we’ll take it from there.
T4M Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by RVAbruh
1 year ago
Preview thumbnail for 27 [T4M] Chicago, Illinois - Roses are red. Violets are blue. I'm a crossdresser. Want to pound me, too? (West Loop) image
27 [T4M] Chicago, Illinois - Roses are red. Violets are blue. I'm a crossdresser. Want to pound me, too? (West Loop)
T4M
in Chicago, IL
to r/Chicagosissies by MDvirgin
1 year ago
Preview thumbnail for 26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop? image
26 [T4M] Chicago, Illinois - Want to try topping a cross-dresser like me in West Loop?
T4M
in Chicago, IL
to r/Chicagosissies by Mysterious_Radish_57
1 year ago
Preview thumbnail for 26 [t4m] any hairy guys?? Love uncut too I really want to find a fwb, who's serious. One time is also fine: discreet only! NO PIC NO CHAT. I love to service, and show off my oral skills. Kinky is always fun too. Ask any questions you want! image
26 [t4m] any hairy guys?? Love uncut too I really want to find a fwb, who's serious. One time is also fine: discreet only! NO PIC NO CHAT. I love to service, and show off my oral skills. Kinky is always fun too. Ask any questions you want!
T4M Chicago
in Chicago, IL
to r/Chicagosissies by Necessary-End-8112
1 year ago
35 [t4m] #oak brook looking for anon fun - a regular would be best so I can find cum every week
T4M
in oak
to r/Chicagosissies by chicagofemboy
1 year ago
Preview thumbnail for 24[T4M] i want a masculine man to submit to me 😇 are you a straight guy curious to get your ass ate? 😈 want to be pegged? let me dominate you in the sheets 🥰 hosting in Pilsen, send a pic for my reply image
24[T4M] i want a masculine man to submit to me 😇 are you a straight guy curious to get your ass ate? 😈 want to be pegged? let me dominate you in the sheets 🥰 hosting in Pilsen, send a pic for my reply
T4M
in Chicago, IL
to r/Chicagosissies by Necessary-End-8112
1 year ago
35 [t4m] sissy in oak brook looking for anon fun during the week and sometimes during the day
T4M
in Chicago, IL