CASUAL ENCOUNTERS Chicago

157 - 168 of 459 listings
Listings
  • COLLEGE GIRL AVAILABLE - w4m - 22 - Chicago IL

    COLLEGE GIRL AVAILABLE - w4m - 22 - Chicago IL

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

    Good to see you guys I,m TAMMY 22 year old Young seXxy College Girl seeking stronger man (age no matter). Must be discreet Let's have a good time:). Available 6pm – 9am. I can host. contact me By email only

  • PnP anyone? - m4m - 36 - Chicago IL

    PnP anyone? - m4m - 36 - Chicago IL

    Men looking for Men Chicago (Illinois) April 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. ...

  • Looking for fun couples to play with - m4mw - 47 - Chicago IL

    Looking for fun couples to play with - m4mw - 47 - Chicago IL

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

    47y/o straight male looking for fun with couples, older than me or interracial are big bonuses. No drugs nor drama. No is no. I've done this before and I'm super discreet.

  • right man - w4m - 24 - Chicago IL

    right man - w4m - 24 - Chicago IL

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

    looking for the right soulmate for a long term relationship

  • Teach me how to ride - w4m - 25 - Chicago IL

    Teach me how to ride - w4m - 25 - Chicago IL

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

    Very high drive. Looking for long and hard time. I wanna feel it bare. Must be ddf. HMU if interested.... Pics get replies

  • Bi curious male - m4m - 55 - Chicago IL

    Bi curious male - m4m - 55 - Chicago IL

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

    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 18, 2026

    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...

  • Looking for fun - w4m - 28 - Chicago IL

    Looking for fun - w4m - 28 - Chicago IL

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

    Hi I am a 28 year old pretty girl and looking for a serious relationship. I am independent, outgoing and funny. Must be a social person.

  • Im a single mother - w4m - 33 - Chicago IL

    Im a single mother - w4m - 33 - Chicago IL

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

    I’m a single mother 33y/o seeking for discreet fun and friends with benefits

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

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

    Women looking for Men Chicago (Illinois) April 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 ;)

  • 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) April 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..

  • 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) April 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