Coming soon - Get a detailed view of why an account is flagged as spam!
view details
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.

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
Showing posts with Daddy
remove filter
Sort by: New Top
to r/Chicagosissies by RudeArm7089
1 year ago
36 bear daddy coming to Chicago for a few hours on Friday I’m going to get a room near ohare
in Chicago, IL
to r/Chicagosissies by davealpha13
1 year ago
28 [M4T] Chicago - Hung Last two weeks in Chicago, let's have some nsa fun hmu
M4T
in Chicago, IL
to r/Chicagosissies by davealpha13
1 year ago
28 [M4T] Chicago - Last two weeks hung jock is in Chicago, let's have some nsa fun
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4s] Top married sensual Dom seeking regular LTR for monthly get togethers
M
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] Hosting in McHenry county starting the afternoon of Monday the 15th until Thursday evening.
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd/T/fem] Dom Bear looking for feminine bottom for fun today in McHenry
M4CD M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] Looking in the Chicago NW burbs. Specifically McHenry/Lake Counties.
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 [m4t] [m4cd] - Looking for a petite fem sissy for this Friday 4/7 that can host in the NW Burbs
M4CD
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
38 Top Male looking for a fem sissy in McHenry lake county for tonight. Seeking a host
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 Chub Daddy seeking sissy or cd who wants to take care of my body - Able to host in western burbs at a hotel
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 Oakbrook Daddy looking for sissy who lets me do as I desire - Can host at a hotel
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 Oakbrook - WM, Bi, Married, Vers looking for a spooning and cuddle buddy to watch some porn
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 Oakbrook Vers looking for Vers/sissy / CD to fulfill my desires and allow me to recip
in Chicago, IL
to r/Chicagosissies by KGChicago801
1 year ago
40 [m4t] Daddy, looking for fantasy trap for mutual oral, cum, and anal play, located NW Burbs but can travel to you
M4T
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 Naperville Two WM looking for sissy / CD to please the both of us while you play dress up
in Chicago, IL
to r/Chicagosissies by Physical-Bathroom729
1 year ago
31 WM - Chub - Looking for CD or Sissy to worship my body and let me explore theirs…in Schaumburg and can host
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4t] Hosting petite CD/Trans tonight in McHenry lets get together and have some fun!
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd] Hosting and Looking for smooth, fem CD/fem for Thursday 1/12 night fun in McHenry
M4CD
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 male hosting today at noon looking for a young cd/femboy/trans girl for sensual play In McHenry
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4t] Hosting a petite lingerie loving trans/CD today in the NW Burbs (McHenry) for right now!
M4T
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 m4t hosting in McHenry tomorrow morning 9am! Looking for young sexy sissy for some fun
M4T
in Chicago, IL
to r/Chicagosissies by EricG435
2 months ago
56 Daddy visiting Chicago looking for sissies, transfemmes and fembois to pamper and spoil
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 [m4cd]Dom Top traveling seeking petite younger bottom in McHenry county.
M4CD
in Chicago, IL
to r/Chicagosissies by VersBear1985
1 year ago
37m dom dad hosting young sissy, fem, cd or trans this morning to early afternoon in McHenry Illinois
in McHenry, IL
to r/Chicagosissies by VersBear1985
1 year ago
37 Dom Daddy House sitting tonight in Wonder Lake Illinois, slip through the back door and lets fuck in someone else’s bed.
in Wonder Lake, IL