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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 AgressiveCPU
4 weeks ago
I’m a 19 black [M] looking for free sex with female/trans. I can’t host and this my first time on here
M
in Chicago, IL
to r/Chicagosissies by Nsfwmind1
11 months ago
19m4a any fems or trans mobile in the west suburbs dm me asap located in Naperville.
M4A
in Chicago, IL
to r/Chicagosissies by PsychologicalTip2245
11 months ago
27 M [M4T] in Rochelle . Looking to host a tran and or sissies. Have pics if you need some
M4T
in Chicago, IL
to r/Chicagosissies by AgressiveCPU
4 weeks ago
I’m 19 black[M] looking for a one night stand I can’t host. I’m in West Chicago
M
in Chicago, IL
to r/Chicagosissies by Big_Situation1664
11 months ago
18m Naperville straight guy M4T looking to get some good sloppy head. Bonus if we can fuck after
M4T
in Chicago, IL
to r/Chicagosissies by hungkink
6 months ago
39 M4T. Hung, heavy cummer. Looking for a handjob. You must host or car play
M4T
in Chicago, IL
to r/Chicagosissies by Gabe______7
7 months ago
21 Daddy [M4T] [M4Fem] Chicago, IL: looking for thicker asses. Anyone Available later tn in Burbank or nearby ?
M
in Thick, TN
to r/Chicagosissies by sunshinetexan
10 months ago
33 (M4T) looking for BJ, rimming, and fun tonight. I can host or travel. Looking near North Chicago area.
M4T
in Chicago, IL
to r/Chicagosissies by Gabe______7
7 months ago
21 Daddy [M4T] [M4Fem] Chicago, IL: looking for thicker asses. Anyone Available later tn in Burbank or nearby ?
M
in Thick, TN
to r/Chicagosissies by dominatior4539
11 months ago
25 M4R crossdressing right now on cam. Need a bud to help out. Whos down to help me as i cam for them.
M4R
in Chicago, IL
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 Cautious_Tiger6859
11 months ago
m19 looking for hung sissy to fuck me. i’m in palatine. 5’8 200 send any pics in dms
M
in Chicago, IL
to r/Chicagosissies by bi_novelty
1 year ago
Preview thumbnail for 26 [M4T] coming to downtown tomorrow for pride weekend. Looking to have fun. Open to anything. Can't host but can travel. image
26 [M4T] coming to downtown tomorrow for pride weekend. Looking to have fun. Open to anything. Can't host but can travel.
M4T
in Chicago, IL
to r/Chicagosissies by RecipeEmbarrassed767
1 year ago
Preview thumbnail for 22 [M4T] Looking for any Sissies that like Black guys In the Frankfort area Mainly looking for a fwb and I can travel image
22 [M4T] Looking for any Sissies that like Black guys In the Frankfort area Mainly looking for a fwb and I can travel
M4T Chicago-south-burbs
in Chicago, IL
to r/Chicagosissies by Odd_Tank_5570
1 year ago
23 [m4tf/fb] #bronzeville - let me give you a nice massage with this 7in BBC
M4TF M4FB Chicago
in Bronzeville
to r/Chicagosissies by RecipeEmbarrassed767
1 year ago
Preview thumbnail for 22 [M4T] Looking for any Sissies that like Black guys In the Frankfort area image
22 [M4T] Looking for any Sissies that like Black guys In the Frankfort area
M4T Chicago-south-burbs
in Chicago, IL
to r/Chicagosissies by chibottom69
1 year ago
Preview thumbnail for 29 [M4MI #Norwood Park -sissy bottom looking for FWB top/tops for daytime fun image
29 [M4MI #Norwood Park -sissy bottom looking for FWB top/tops for daytime fun
M4M
in Norwood
to r/Chicagosissies by Wide_Grab_7197
1 year ago
35m4A Naperville daddy have a hotel so can host looking to use a warm wet mouth. Must be 18+. I'm from st.louis here for business really hoping to have some fun
M4A Chicago-west-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 Broad-Bridge30
8 months ago
Preview thumbnail for 29m4sissie/CD looking for some fun Big cock, few beers and fun wise I’m all ears but a tad picky but that’s why ppl have friends right? 😎😏 image
29m4sissie/CD looking for some fun Big cock, few beers and fun wise I’m all ears but a tad picky but that’s why ppl have friends right? 😎😏
M Chicago
in Chicago, IL
to r/Chicagosissies by kinkiestmale
1 year ago
30 [M4T] Dominant male looking for someone who can host. I prefer femme body types
M4T Chicago
in Chicago, IL
to r/Chicagosissies by dominatior4539
1 year ago
25 M4R starting to explore CD and would love some help. I am around schaumburg. Also interested in mutal jo. Whos down to help out? Got gf’s clothes to wear
M4R
in Chicago, IL
to r/Chicagosissies by kreator1988
1 year ago
Preview thumbnail for 34 [m4t] South suburbs top for petite bottom for carplay or host. Safe play only image
34 [m4t] South suburbs top for petite bottom for carplay or host. Safe play only
M4T
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