CASUAL ENCOUNTERS Chicago

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Listings
  • Sexy bottom looking for Dom hung tops! BBC A+ - m4m - 39 - Chicago IL

    Sexy bottom looking for Dom hung tops! BBC A+ - m4m - 39 - Chicago IL

    Men looking for Men Chicago (Illinois) September 22, 2026

    Sexy bottom, 5 9, 200, totally smooth, oral talented, love deepthroating! Big smooth WAP with strong squeeze muscles!!!!!! Like to xdressing too! Love very TALL dom hung masculine tops! Str8 and bi doms A+ BBC/BWC, very tall, muscle, furry daddies, h...

  • couple in pearl district - mw4g - 48/42 - Chicago IL

    couple in pearl district - mw4g - 48/42 - Chicago IL

    Couples looking for Group Chicago (Illinois) September 22, 2026

    mixed couple in the downtown area looking for sexual fun with men, women and couples. he is black ,straight and in athletic shape well hung very oral, she is white, bi and very oral loves toy play, multiple positions , eating pussy giving head. . we ...

  • Mskittycat69 - w4m - 27 - Chicago IL

    Mskittycat69 - w4m - 27 - Chicago IL

    Women looking for Men Chicago (Illonis ) September 22, 2026

    27 single sexy kinky hot young chocolate sugar babie on here to meet / hookups I'm available let's talk hit me up

  • Dominant - w4m - Chicago IL

    Dominant - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) September 21, 2026

    I’m Mistress Mary, a confident and experienced Dom seeking a genuine, long-term connection with a devoted submissive who values honesty, trust, respect, and authentic communication. I believe the strongest dynamics are built on mutual understanding, ...

  • Goddess seeking serious submissive male for long or short time relationship - w4m - 29 - Chicago IL

    Goddess seeking serious submissive male for long or short time relationship - w4m - 29 - Chicago IL

    Women looking for Men Chicago (Illinois) September 21, 2026

    I am looking for a loyal and caring man who prides himself on his dedication to serve a woman for a long term relationship caring for her needs and desires. You will find a dominant woman who will cherish you and your service to her. Hopefully you ar...

  • Wet black pussy - w4m - 46 - Chicago IL

    Wet black pussy - w4m - 46 - Chicago IL

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

    Big horny clit and full wet pussy lips

  • Straight looking to get rimmed slowly - m4m - 39 - Chicago IL

    Straight looking to get rimmed slowly - m4m - 39 - Chicago IL

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

    Would like to find a regular older experienced guy who likes to rim. 39 years old here. Smooth and clean everywhere. Very discreet. If you’re older, experienced and can host, hit me up. I come over, bend over and you can take your time. Maybe play so...

  • Orgy - mw4t - 37/39 - Chicago IL

    Orgy - mw4t - 37/39 - Chicago IL

    Couples looking for Trans Chicago (Illinois) September 16, 2026

    My wife and I are looking for 8 or more well endowed black and Latina transgender women who are top only to come and spend from a few days to a couple of weeks DOMINATING us from both ends at all angles

  • Group Fun - m4g - Chicago IL

    Group Fun - m4g - Chicago IL

    Men looking for Group Chicago (Illinois) September 16, 2026

    Looking for any interested guys and a female for a fun casual hotel sex fun evening. No guy on guy. Needs to be discrete, safe, healthy but fun. May even look into an escort. HMU if anyone interested. Age, looks, size don’t matter; just need to be a ...

  • Virgin guy looking for anything - m4w - 20 - Chicago IL

    Virgin guy looking for anything - m4w - 20 - Chicago IL

    Men looking for Women Chicago (Illinois) September 16, 2026

    20 year old virgin. Down for whatever you want. Cannot host, but willing to meet up. Contact me at (312) 919-9345

  • 42/y lonely women - w4m - 42 - Chicago IL

    42/y lonely women - w4m - 42 - Chicago IL

    Women looking for Men Chicago (Illinois) September 16, 2026

    My husband will have no part in this and he will NOT know.I am looking for someone. I am open-minded.

  • Key - m4w - 32 - Chicago IL

    Key - m4w - 32 - Chicago IL

    Men looking for Women Chicago (Illinois) September 16, 2026

    Looking for casual encounter