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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 MerryNewYear_
1 year ago
20 [M4T] Evanston- straight curious. Any fems/sissies wanna cum over tonight and fulfill my fantasies?
M4T Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by AnonymousAsian312
1 year ago
32 m4cd Elmhurst Asian male looking for a sissy. Can’t host. Must be discreet.
M4CD
in Chicago, IL
to r/Chicagosissies by Ok_today2827
1 year ago
23 [M4T] Portage Park sissy looking for a possible hook up later tonight. Check profile for pics.
M4T Chicago
in Chicago, IL
to r/Chicagosissies by davealpha13
1 year ago
28 [M4T] Chicago - Hung Last two weeks in Chicago, let's have some nsa fun hmu
M4T
in Chicago, IL
to r/Chicagosissies by davealpha13
1 year ago
28 [M4T] Chicago - Last two weeks hung jock is in Chicago, let's have some nsa fun
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4s] Top married sensual Dom seeking regular LTR for monthly get togethers
M
in Chicago, IL
to r/Chicagosissies by Effective_Text8282
1 year ago
23 [M4T] naperville straight guy here looking for first time experience. Dm me
M4T Chicago-south-burbs
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] Hosting in McHenry county starting the afternoon of Monday the 15th until Thursday evening.
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd/T/fem] Dom Bear looking for feminine bottom for fun today in McHenry
M4CD M4T
in Chicago, IL
to r/Chicagosissies by travelingthrow1
1 year ago
37 [M4T] #Downtown - business traveler looking for discreet fun. Maybe a bit of exploring
M4T Chicago
in Downtown
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] Looking in the Chicago NW burbs. Specifically McHenry/Lake Counties.
M4T
in Chicago, IL
to r/Chicagosissies by CardGroundbreaking28
1 year ago
35M4T/S Chicago looking for fun near Midway or Naperville. Huge pantyhose fetishist. Looking for my first time. Please dominate me.
M4T Chicago
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] [m4cd] - Looking for a petite fem sissy for this Friday 4/7 that can host in the NW Burbs
M4CD
in Chicago, IL
to r/Chicagosissies by Megus-O13
1 year ago
37[M4CD] Laid-back bro lookin for certain kinds of fem or passive cuties in North burbs..twinks, short, shy+++
M4CD Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by KGChicago801
1 year ago
40 [m4t] Daddy, looking for fantasy trap for mutual oral, cum, and anal play, located NW Burbs but can travel to you
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4t] Hosting petite CD/Trans tonight in McHenry lets get together and have some fun!
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd] Hosting and Looking for smooth, fem CD/fem for Thursday 1/12 night fun in McHenry
M4CD
in Chicago, IL
to r/Chicagosissies by looklikeleap
1 year ago
29 [M4T] want to go to Te Jays adult bookstore tonight and get blown. I’m so horny and want to start the year off strong
M4T Chicago
in Chicago, IL
to r/Chicagosissies by bi_novelty
1 year ago
Preview thumbnail for 25 [m4t] Chicago Loop, looking for sissies to have fun this weekend. Can host or travel. image
25 [m4t] Chicago Loop, looking for sissies to have fun this weekend. Can host or travel.
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4t] Hosting a petite lingerie loving trans/CD today in the NW Burbs (McHenry) for right now!
M4T
in Chicago, IL
to r/Chicagosissies by tireddawg
1 year ago
27 [M4T] I like big toys, hbu? tall, handsome, BWC Just shoot me a DM and Lets see where it goes
M4T Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 m4t hosting in McHenry tomorrow morning 9am! Looking for young sexy sissy for some fun
M4T
in Chicago, IL
to r/Chicagosissies by urdreamwife
1 year ago
Preview thumbnail for 27 [M] #chicago #boystown Looking for someone with friends to take turn 6'1, 150 pound, sissy white boy who wants to bend over and have his asshole used and abused until I'm filled with cum and it's leaking out of every hole. image
27 [M] #chicago #boystown Looking for someone with friends to take turn 6'1, 150 pound, sissy white boy who wants to bend over and have his asshole used and abused until I'm filled with cum and it's leaking out of every hole.
M
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd]Dom Top traveling seeking petite younger bottom in McHenry county.
M4CD
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd] Dom daddy Hosting tonight 10/14 after 9pm for an hour or 2 in WONDER LAKE
M4CD
in Chicago, IL