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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 Medical_Midnight3693
3 weeks ago
[USA] #Chicago #Illinois #IL 40-Year-Old Dominant Male Seeking Ongoing Dynamic M4T / M4CD / M4Femboy
Chicago
in USA
to r/Chicagosissies by Medical_Midnight3693
4 weeks ago
[USA] #Chicago #Illinois - 40-Year-Old Dominant Seeking an Ongoing Connection.
Chicago
in USA
to r/Chicagosissies by No_Check_4526
1 month ago
22 [M4T] shore drive desperate for a blow job and dominate me badmouthing , verbal abuse and pegging is also allowed (first time )
M4T Chicago
in Chicago, IL
to r/Chicagosissies by LynnWyatt
4 months ago
Preview thumbnail for 40 [tf4m] #rivernorth - relocating and looking for connections while relocating and maybe long term FWB image
40 [tf4m] #rivernorth - relocating and looking for connections while relocating and maybe long term FWB
TF4M Chicago
in RiverNorth
to r/Chicagosissies by Chibmc1999_on_sc
3 months ago
I need head please help me 25 years old Mexican can host in the morning by Cicero and Belmont
Chicago
in Chicago, IL
to r/Chicagosissies by Old_Abbreviations524
10 months ago
35 [mf4m] #loop - looking to host a gangbang tonight. Girls and gurls welcome too
MF4M Chicago
in Loop
to r/Chicagosissies by kinkiestmale
11 months ago
30 [M4S] #Online or #Illinois - Experienced daddy looking for a femme passable sissy
M Chicago
in Illinois
to r/Chicagosissies by Ella_thesexdoll
1 year ago
Preview thumbnail for 26 Chicago(Wrigley) CD/T - Looking for some fun with straight/curious men who can toss me and my big booty around. Ps, I’m back. 😉. image
26 Chicago(Wrigley) CD/T - Looking for some fun with straight/curious men who can toss me and my big booty around. Ps, I’m back. 😉.
Chicago
in Chicago, IL
to r/Chicagosissies by Jumpy-Isopod-2443
1 year ago
25yr straight daddy looking for a cute sissy/fem located by midway and Chicago area! Mobile as well
Chicago
in Chicago, IL
to r/Chicagosissies by AcceptableTreat195
1 year ago
18 Bi curious virgin looking to get my first blowjob curious virgin looking for his first blown job
Chicago
in Chicago, IL
to r/Chicagosissies by ATLmwmCD
1 year ago
Preview thumbnail for 38 [t4m] #rivernorth - here for work again and looking for a good time with discreet guy image
38 [t4m] #rivernorth - here for work again and looking for a good time with discreet guy
T4M Chicago
in RiverNorth
to r/Chicagosissies by daddyerotic
1 year ago
[50s] Daddy Seeking A Sexy Hookup For Chicago Fan Expo, August 11th or 12th
Chicago
in Chicago, IL
to r/Chicagosissies by Lgs0903
1 year ago
21 curious college student with a tiny cock probably smallest you'll ever see also a wannabe sissy
Chicago
in Chicago, IL
to r/Chicagosissies by sissyaznCDmdwst
1 year ago
28 [T4M] #chicago - Fem passable Asian sissy CDer needs a breeding and creampie
T4M Chicago
in Chicago, IL
to r/Chicagosissies by Over8inchesplease
1 year ago
Preview thumbnail for 25 [T4M] Petite Latin size queen seeking the biggest ( st8 of bi men to the front) image
25 [T4M] Petite Latin size queen seeking the biggest ( st8 of bi men to the front)
T4M Chicago
in Chicago, IL
to r/Chicagosissies by ConfusedPartnerAITA
1 year ago
22m #loop dom-type looking for cd/sissy/passable submissive for kink-forward fun
Chicago
in Loop
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 Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sisst looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by Maxlevel23
1 year ago
24M. Any fem bottoms looking for a relationship with a black chub? I'm a strict top
Chicago
in Chicago, IL
to r/Chicagosissies by Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
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 Accurate-Gap-4518
1 year ago
23 [T4M] #Portage Park - Sissy looking for a possible hook up. Check profile for pics.
T4M Chicago
in Portage
to r/Chicagosissies by kiksarefun
1 year ago
32 year old former sissy with wife out of town looking for someone to play with. north side neighborhood, can host
Chicago
in Chicago, IL