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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
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to r/Chicagosissies by omega300m
2 weeks ago
30 Schaumburg - Bicurious seeking to explore with a cute twink, fem, or sissy
in Chicago, IL
to r/Chicagosissies by AirlineTimely4777
3 months ago
#Chicago 25 Hung and Fit BWC college guy seeking ts or sissy for ongoing fun
in Chicago, IL
to r/Chicagosissies by Delekina
3 months ago
30 M Lake County - Looking for a sissy/crossdresser/trans to have some fun with
in Chicago, IL
to r/Chicagosissies by SissyPlace4u
4 months ago
47m #DesPlaines - I’d love to give a younger crossdresser my cock to practice oral on
in DesPlaines
to r/Chicagosissies by Infinite_Cress954
4 months ago
31 [M4T] #Joliet - I really really really want to make love to a trans woman
M4T
in Joliet
to r/Chicagosissies by SissyPlace4u
4 months ago
47 [M4CD] #DesPlaines - Looking for a crossdresser that needs a secret place to dress
M4CD
in DesPlaines
to r/Chicagosissies by Infinite_Cress954
4 months ago
31[M4T] #Joliet - I want to meet a trans-woman so bad - dad/dadbod can host and or travel - much lover / BIG affection
M4T
in Joliet
to r/Chicagosissies by Infinite_Cress954
4 months ago
31[M4T] #Joliet - My strongest desire.. white tatted dadbod and not really hung.. but hella horny and eager to try new things..
M4T
in Joliet
to r/Chicagosissies by SissyPlace4u
4 months ago
47 [M4CD] #DesPlaines - Looking for a crossdresser that needs a secret place to dress up
M4CD
in DesPlaines
to r/Chicagosissies by Delekina
3 months ago
31 Male M4T or M4Femboy between Mundelein & Grayslake area seeking someone to have some fun with
M4T
in Chicago, IL
to r/Chicagosissies by Fluid-Elephant-6264
5 months ago
25[M4F/T] looking for nasty fun now near east chicago. I’m 9 inches, 6’2, athletic build and attractive biracial. Daddy Looking for fem
M4F M4T
in Chicago, IL
to r/Chicagosissies by omega300m
6 months ago
29 Asian straight top looking for sissy for cuddles, new experiences, and maybe more in the NW Suburbs
in Chicago, IL
to r/Chicagosissies by WiscoLicker
5 months ago
18 Male [M4T] Kenosha Area, WI. Sub looking to be a bottom for a trans/sissy.
M4T
in Kenosha, WI
to r/Chicagosissies by bobfrfun
3 weeks ago
39 WM(Daddy) in Gold Coast Hotel 4/10-4/12 and looking to host a hot bottom Sissie:) Flexible Schedule
in Chicago, IL
to r/Chicagosissies by AirlineTimely4777
7 months ago
25M chicago area hung college top looking for sissy or ts to dominate and own
in Chicago, IL
to r/Chicagosissies by soultakerte
7 months ago
35 [M4T] looking for some fun in my area I'm in Chicago heights , looking for a chub if possible
M4T
in Chicago, IL
to r/Chicagosissies by Yellowsubmarine-2
7 months ago
Bicurious 21 m4t bull Joliet area for meetups looking for a sissy to experiment with
M4T
in Chicago, IL
to r/Chicagosissies by Rrrrr2323
3 months ago
Preview thumbnail for 58 yr old Looking for fun. Straight M looking 4 TS/CD. I’m in W Burbs. into sissy image
58 yr old Looking for fun. Straight M looking 4 TS/CD. I’m in W Burbs. into sissy
in Chicago, IL
to r/Chicagosissies by omega300m
8 months ago
29 #Schaumburg/NW Suburbs - Looking for cute sissy to snuggle with and more
in Schaumburg/NW
to r/Chicagosissies by omega300m
8 months ago
29 #Schaumburg/NW Suburbs - Looking for cute sissy to snuggle with and more
in Schaumburg/NW
to r/Chicagosissies by burbs4funn
8 months ago
35 M4S hosting at McCormick for fun. Prefer younger bottoms 👀👀👀 looking all weekend
M
in Chicago, IL
to r/Chicagosissies by burbs4funn
10 months ago
35 year old guy hosting at mcormick center weekend of 2/23. Looking for younger sissy.
in Chicago, IL
to r/Chicagosissies by omega300m
10 months ago
29M #Schaumburg - Inexperienced Asian looking to have fun with twinks, sissies, or fem
in Schaumburg
to r/Chicagosissies by burbs4funn
10 months ago
35 yr old guy in Chicago on 02/22. Looking for a young sissy that weekend. Can host in hotel.
in Chicago, IL
to r/Chicagosissies by idkpoof
10 months ago
21 bbc #bolingbrook top looking for the perfect sissy to make my wife hmu if it sound perfect to you:)
in Bolingbrook