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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 chiguy0004
1 month ago
31 [M4T/Fem] Evanston - Gentleman looking for a fun and flirty transwoman or fem identifying person for a casual relationship with a strong connection.
M4T
in Chicago, IL
to r/Chicagosissies by chiguy0004
2 months ago
31 [M4T/Fem] Evanston - Gentleman looking for a fun and flirty transwoman or fem identifying person for a casual relationship with a strong connection.
M4T
in Chicago, IL
to r/Chicagosissies by LigmaPenguiin
6 months ago
36 daddy looking for a sissy for next weekend to take care of me while my woman watches
in Chicago, IL
to r/Chicagosissies by slipperycock2
8 months ago
27 [M4T] #Lakeview - Looking for a trans woman, sissy, or smooth bottom to breed
M4T
in Lake View, Chicago
to r/Chicagosissies by slipperycock2
9 months ago
27 [M4T] #Lakeview - Straight, tall, handsome guy looking for trans woman, sissy, cross dresser, or femboy on the north side
M4T
in Lake View, Chicago
to r/Chicagosissies by Glad_Insurance4486
1 month ago
Daddy (South Burbs, 27) seeks sissy. host only cant travel. Tested and clean.
in Chicago, IL
to r/Chicagosissies by LigmaPenguiin
6 months ago
36m bicurious looking for a trans, sissy or somewhat passable cd to get nasty with the weekend of the 10th in the western burbs, I will be hosting
in Chicago, IL
to r/Chicagosissies by slipperycock2
10 months ago
27 [M4T] #Lakeview - Straight, tall, handsome guy looking for trans woman, sissy, cross dresser, or femboy to breed all weekend long
M4T
in Lake View, Chicago
to r/Chicagosissies by LigmaPenguiin
6 months ago
36 daddy (western burbs area) looking for some fun the weekend of the 13th, might have a third join in.
in Chicago, IL
to r/Chicagosissies by chiburbsguy4sissy
10 months ago
32 Daddy Seeking a sexy sissy, cd or trans. North Burbs Gurnee Area or Southern Wisconsin
in Wisconsin
to r/Chicagosissies by slipperycock2
10 months ago
27 [M4T] #Lakeview - Straight, tall, handsome guy looking for trans woman, sissy, cross dresser, or femboy on the north side
M4T
in Lake View, Chicago
to r/Chicagosissies by slipperycock2
10 months ago
27M Tall and large straight guy looking to bully your hole and climax inside you tonight, Northside
in Chicago, IL
to r/Chicagosissies by thornystick69
2 months ago
24m daddy looking for a bottom to experiment with. Looking to see what’s out there and I Ive been questioning my sexual preferences a lot recently and finally want to do something about it.
in Chicago, IL
to r/Chicagosissies by Wild_Lime5062
10 months ago
[33 Daddy] NEEDING!! to Experience it at least once and may be only chance —Naperville
in Chicago, IL
to r/Chicagosissies by slipperycock2
10 months ago
27 M, Straight and strapping European guy looking for a sissy side piece on Chicago’s North Side
in Chicago, IL
to r/Chicagosissies by urfeetonmyface
11 months ago
[42][Chicago][Daddy] Horny daddy Looking for Cute kinky smooth sissy host!!
in daddy
to r/Chicagosissies by clonly101
11 months ago
[33]- [Oak Brook]- Asian [Daddy] Top looking for sissy bottom discreet NSA ongoing FWB
in daddy
to r/Chicagosissies by FrostyAnimator8188
11 months ago
Preview thumbnail for 23M Plainfield - Looking for someone to explore kinks + if you have pretty feet image
23M Plainfield - Looking for someone to explore kinks + if you have pretty feet
in Chicago, IL
to r/Chicagosissies by FrostyAnimator8188
11 months ago
Preview thumbnail for [23] [Plainfield] [Daddy] - looking to meet new people and explore kinks, dm me if your interested in meeting up image
[23] [Plainfield] [Daddy] - looking to meet new people and explore kinks, dm me if your interested in meeting up
in daddy
to r/Chicagosissies by chiburbsguy4sissy
10 months ago
32 Looking for a sexy sissy, cd or trans. North Burbs Gurnee Area or Southern Wisconsin
in Wisconsin
to r/Chicagosissies by Gabe______7
7 months ago
22 Chicago daddy: looking for sissy near the oak lawn/midway area. Please be able to host
in Chicago, IL
to r/Chicagosissies by AutomaticSwing9621
1 year ago
30 daddy looking for a sissy to train! DMs are open! Tell me your kinks, all are welcome ;)
in Chicago, IL
to r/Chicagosissies by Gabe______7
7 months ago
Preview thumbnail for 21 [Daddy4A] Chicago, IL: looking for thicker asses. Anyone Available later tn in Burbank or nearby ? Message a pic of you and location if interested. Please be clean and tested! Please be clean !! image
21 [Daddy4A] Chicago, IL: looking for thicker asses. Anyone Available later tn in Burbank or nearby ? Message a pic of you and location if interested. Please be clean and tested! Please be clean !!
in Thick, TN
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 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