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Chicago, IL

r/Chicagosissies

9,342 subscribers
Chicagoland, Northwest Indiana and Southern Wisconsin area Sissy / CD / transfemme personals. Request approval to post ads in our "about" menu.

Moderators

Updated Apr 6, 2024
u/MisterTrapDaddy Active
Added 3 years ago
Also moderates: r/FeminizedForDaddy, r/FloridaFeminization

Notice: This subreddit is not actively monitored, so the posts here are only a small subset of what exists on reddit.

Browse by flair

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
New Top (24hr) Top (Week) Top (Month)
to r/Chicagosissies by No_Check_4526
4 weeks 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 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
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 Glass_Inevitable_197
2 months ago
31 [M4T/A] Joliet - White top/verse Dad LF T/Fem for tonight or some night next week ongoing or one time whatever’s clever super serious about making this happen
M4T M4A Chicago-southwest-burbs
in Chicago, IL
to r/Chicagosissies by Glass_Inevitable_197
2 months ago
31 [M4T/A] Joliet - White top/verse Dad LF T/Fem for tonight or some night next week ongoing or one time whatever’s clever super serious about making this happen
M4T M4A Chicago-southwest-burbs
in Chicago, IL
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 WiscoLicker
4 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 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 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 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 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 slipperycock2
9 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 urdreamwife
10 months ago
27 M4MM #Lakeview Sissy Fantasy request! Two anonymous cocks covering my face with cum
M4MM
in Lake View, Chicago
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 Common-Prize-9148
10 months ago
20 [M4T] #naperville - Any girl particularly gassy who would want to fart on my lap?
M4T
in Naperville, IL
to r/Chicagosissies by nekomaid2
9 months ago
Preview thumbnail for M19 Femboy Aurora/Naper wondering if any femboy and or sissy may be able to help me learn a new skill of sucking dick image
M19 Femboy Aurora/Naper wondering if any femboy and or sissy may be able to help me learn a new skill of sucking dick
M
in Chicago, IL
to r/Chicagosissies by Lonely-Reaction5215
11 months ago
25/M4S/Chicago willing to travel Is anyone on here not a bot or not selling of M25open minded5”9 willing to send pictures
M Chicago-south-burbs
in Chicago, IL
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