CASUAL ENCOUNTERS Chicago

229 - 240 of 449 listings
Listings
  • Bi curious male - m4m - 55 - Chicago IL

    Bi curious male - m4m - 55 - Chicago IL

    Men looking for Men Chicago (Illinois) April 29, 2025

    55yrs bi curious male 185lbs 511 8in cut average looking medium build ddf versital open-minded tight asshole. Looking to be serviced by the biggest cock out there for my birthday on Monday you must host

  • Yo - m4w - 36 - Chicago IL

    Yo - m4w - 36 - Chicago IL

    Men looking for Women Chicago (Illinois) April 29, 2025

    What's up I'm a 36 year old single black man. I'm trying to kick and have fun. I like to go out and I like to chill in. I smoke(420) and I'm a casual drinker. I'm looking for my pillow princess. I'm looking for my princess period. hit me up 331-301-0...

  • Unhappy_older_Woman - w4m - 35 - Chicago IL

    Unhappy_older_Woman - w4m - 35 - Chicago IL

    Women looking for Men Chicago (Illinois) April 29, 2025

    I am unhappy and lonely fun sexy horny milf looking to get off.. Pic swap.. And maybe meet if the vibe is right.Shaved, wet and ready. I just want someone who can make me happy

  • Couple looking for a male to join - mw4m - 38/37 - Chicago IL

    Couple looking for a male to join - mw4m - 38/37 - Chicago IL

    Couples looking for Men Chicago (Illinois) April 29, 2025

    We are a married couple looking to spice things up. Looking for an attractive, tall strong male between 30-45. (Hung would be nice too). Meetups mostly would be late night on weekends. Love to find the right person for a regular meet up. Message me i...

  • I WANT REAL HOTY AND HOT DOGGY STYLE - w4m - 26 - Chicago IL

    I WANT REAL HOTY AND HOT DOGGY STYLE - w4m - 26 - Chicago IL

    Women looking for Men Chicago (Illinois) April 29, 2025

    HELLO,,really i am so so alone, but excited because my man out of 69 days.i want a doggy style buddy..

  • Need to taste me some pussy - m4w - 33 - Chicago IL

    Need to taste me some pussy - m4w - 33 - Chicago IL

    Men looking for Women Chicago (Illinois) April 29, 2025

    Looking for a sweet tight wet pussy to eat and get this dick wet let me show you what this tongue do boo, let me lick it for you

  • Looking for some fun. NSA or FWB - w4m - 27 - Chicago IL

    Looking for some fun. NSA or FWB - w4m - 27 - Chicago IL

    Women looking for Men Chicago (Illinois) April 29, 2025

    Looking for some fun. NSA or FWB

  • Looking to host couple in downtown Hotel - m4mw - 54 - Chicago IL

    Looking to host couple in downtown Hotel - m4mw - 54 - Chicago IL

    Men looking for Couples Chicago (Illinois) April 29, 2025

    I am 54, attractive old man staying in Downtown at a nice hotel and would love to host a couple tonight. I am bisexual and love to please both sexes. I open minded and happy to play any role that would make you happy.

  • Fun filled guy - m4w - 33 - Chicago IL

    Fun filled guy - m4w - 33 - Chicago IL

    Men looking for Women Chicago (Illinois) April 29, 2025

    Looking for beautiful ladies in the area to get together with and have a good time satisfy both are sexual needs. Love eating a sweet little psssy before this dick gets wet, if you thing I should get a taste of that pussy shoot me a message

  • Black couple looking for another couple - mw4mw - 26/25 - Chicago IL

    Black couple looking for another couple - mw4mw - 26/25 - Chicago IL

    Couples looking for Couples Chicago (Illinois) April 29, 2025

    We're a fun outgoing AA couple and we want to try something new. we're interested in 3some ff games and couples swap.

  • Couple for female - mw4w - 34/32 - Chicago IL

    Couple for female - mw4w - 34/32 - Chicago IL

    Couples looking for Women Chicago (Illinois) April 29, 2025

    Hi, Discreet couple looking for one female to play with both of us. The female may/may not reciprocate, depending on the mood. He is white, 34, average size, very clean and loves to please. She is 32, sexy, bi and shaved. Responses with pics will be ...

  • Looking for a Handsome hung young guy - mw4m - 29/27 - Chicago IL

    Looking for a Handsome hung young guy - mw4m - 29/27 - Chicago IL

    Couples looking for Men Chicago (Illinois) April 29, 2025

    Going out this friday and gonna see if we click. Please send a pic and description of yourself.