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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 WorkerPlayful2295
10 months ago
Preview thumbnail for 21 #Highland Park looking for a hot dom to fill me Chastity+ Bondage+ Fit+++ image
21 #Highland Park looking for a hot dom to fill me Chastity+ Bondage+ Fit+++
Chicago-north-burbs
in highland
to r/Chicagosissies by Suspicious_Elk_5559
1 year ago
45 [m4t] #chicago (suburbs) looking for a submissive, feminine sissy looking to be respectfully owned
M4T Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by iiHypeRugs
1 year ago
23M4M #brookfield. looking for someone to deepthroat my cock to put me to bed
M4M Chicago-north-burbs
in brookfield
to r/Chicagosissies by iiHypeRugs
1 year ago
23M4M #brookfield. hosting home alone! someone come throat my cock to start my morning right!
M4M Chicago-north-burbs
in brookfield
to r/Chicagosissies by Goddess-Rose69
1 year ago
Preview thumbnail for 23 year old sissy in North Chicago suburbs, 6ft tall and a slim 150 pounds, looking for some fun 💗 image
23 year old sissy in North Chicago suburbs, 6ft tall and a slim 150 pounds, looking for some fun 💗
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by TaytaySin
1 year ago
Preview thumbnail for 40 year old Daddy in Evanston looking for Fem sissy to hang with. I'm bored and ready for fun. image
40 year old Daddy in Evanston looking for Fem sissy to hang with. I'm bored and ready for fun.
Chicago-north-burbs
in Chicago, IL
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 max777783
1 year ago
Preview thumbnail for 45 Sissy Libertyville I like to wear i am a virgin i would like to have a real Daddy to take care of me image
45 Sissy Libertyville I like to wear i am a virgin i would like to have a real Daddy to take care of me
Chicago-north-burbs
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 Fun_Ad_6817
1 year ago
Preview thumbnail for 25 virgin bottom Chicago burbs looking to get pounded hard by older. cannot host image
25 virgin bottom Chicago burbs looking to get pounded hard by older. cannot host
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by harpy146
1 year ago
26 M north side - in search of a cute sissie to have fun with this nice Sunday
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by p0rng00n3r
1 year ago
21m in Crystal lake/Mchenry top looking for femboy/sissy to hook up with tonight
Chicago-north-burbs
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 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 ChicagoNoodle
1 year ago
21 year old bull looking for cute femboy bottom in lakeview area. bonus if you can bring another fem friend!
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by Prizes4389
1 year ago
Bear daddy 36 looking for Sunday. North side or in Niles/ des plaines area between 10-4
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by ramjay1988
11 months ago
26 m latino straight looking to get worship and rim , Andersonville edgewater area
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by Lost_To_The_Zone
3 months ago
26 year old chaste bottom in northern suburbs looking for a sissy to suck off and possibly more.
Chicago-north-burbs
in Chicago, IL
to r/Chicagosissies by No-Face-No-Case90
1 year ago
DL DL DL M32 looking to have my very 1st experience.!!!!!!!!!!!!!!!!!!!!!!!!!
Chicago-north-burbs
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 tireddawg
1 year ago
27 [M4T] I like big toys, hbu? tall, handsome, hung and ready for fun. poppers?
M4T Chicago-north-burbs
in Chicago, IL