CASUAL ENCOUNTERS Chicago

181 - 192 of 452 listings
Listings
  • AA Woman Looking for FWB - w4m - 42 - Chicago IL

    AA Woman Looking for FWB - w4m - 42 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 2026

    Hello, I am an ebony 42 year old women and looking for friends to hangout with. If we happen to click, I may even consider taking our relation up a notch ;)

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

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

    Couples looking for Women Chicago (Illinois) May 18, 2026

    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 ...

  • pull your pants down and let me enjoy it - w4m - 25 - Chicago IL

    pull your pants down and let me enjoy it - w4m - 25 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 2026

    I am 25yrs old horny & need to feel it real bad.. Let me suck ur cock until u cum. i will make u cum like u never have before. can travel or host u.. no strings attached so don't worry if u have a gf or married or whatever..

  • Discrete clean man seeking an exciting female - m4w - Chicago IL

    Discrete clean man seeking an exciting female - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) May 18, 2026

    Mature white male looking to develop a relationship with a wf for a regular long term relationship. I have a lot to offer and I know how to take care of all the needs a woman may have.

  • Young bbc looking for women/wives - m4mw - 21 - Chicago IL

    Young bbc looking for women/wives - m4mw - 21 - Chicago IL

    Men looking for Couples Chicago (Illinois) May 18, 2026

    sup, I'm young black guy looking for women/wives who want a great time. I'm 21, skinny, 6'3, clean, straight, and 8in long. If any women are interested hit me up and let's have fun ;) Yes I'm real unlike these other ads

  • Looking 4 Someone To Eat Me Out - w4m - 22 - Chicago IL

    Looking 4 Someone To Eat Me Out - w4m - 22 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 2026

    Looking for either Female or Male to eat me out and give a good fuck. Looking for someone in the AV area. Fun only, nothing else. **MUST BE DISCREET && CLEAN**

  • Unhappy_older_Woman - w4m - 35 - Chicago IL

    Unhappy_older_Woman - w4m - 35 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 2026

    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) May 18, 2026

    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...

  • 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) May 18, 2026

    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) May 18, 2026

    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

  • PnP anyone? - m4m - 36 - Chicago IL

    PnP anyone? - m4m - 36 - Chicago IL

    Men looking for Men Chicago (Illinois) May 18, 2026

    Anybody down to pnp and get super spn while teaching a straight masculine whiteboy a lil less masculine? Show me what it’s like to not be in charge? I’m Looking for a FWB to party with and have dirty fun with on the super dL. Must be super discreet. ...

  • 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) May 18, 2026

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