CASUAL ENCOUNTERS Chicago

1 - 12 of 452 listings
Listings
  • Good Dick Don’t Cum Often…Let Me Make That PUSSY Proud - m4w - 55 - Chicago IL

    Good Dick Don’t Cum Often…Let Me Make That PUSSY Proud - m4w - 55 - Chicago IL

    Men looking for Women Chicago (Illinois) May 27, 2026

    AA Male…9 inch curve DDF & Hygiene approved. Love providing and receiving oral and would love to hit them flapjacks properly til your moaning all that creamy goodness on my stride. Get at me…this squirrel ready to pump all that nut out of you and...

  • Make your wish come true - w4m - 31 - Chicago IL

    Make your wish come true - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) May 26, 2026

    I’m a simple girl, who like to live young wild and free

  • 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) May 26, 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...

  • Latina woman - w4w - 37 - Chicago IL

    Latina woman - w4w - 37 - Chicago IL

    Women looking for Women Chicago (Illinois) May 26, 2026

    Hi there I'm Latina woman from Chicago lookingito explore with another woman.

  • Juicy black clit - w4m - Chicago IL

    Juicy black clit - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) May 26, 2026

    Want some wet black pussy with a big pink clit? Sexy black female with big dark nipples and a big clit

  • Ready for some fun and excitement - w4m - 25 - Chicago IL

    Ready for some fun and excitement - w4m - 25 - Chicago IL

    Women looking for Men Chicago (Illinois) May 26, 2026

    Hey! I’m available for some fun and excitement. I’m super clean and can bare back. I enjoy kissing cuddling and I can also squirt if you play the game well. Let’s meet and have a great time together

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

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

    Couples looking for Group Chicago (Illinois) May 26, 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 ...

  • 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) May 23, 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...

  • Wet black pussy - w4m - 46 - Chicago IL

    Wet black pussy - w4m - 46 - Chicago IL

    Women looking for Men Chicago (Illinois) May 23, 2026

    Big horny clit and full wet pussy lips

  • 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) May 22, 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...

  • Fwb - m4w - 32 - Chicago IL

    Fwb - m4w - 32 - Chicago IL

    Men looking for Women Chicago (Illinois) May 22, 2026

    What's up I'm Jay I'm 32 6 foot and 170 pounds from the south side of Chicago I'm looking for a friend to kick it with smoke drink eat watch a few shows and have some fun I love eating coochie from the back and driving this long hard wood deep in you...

  • Casual encounters - w4m - Chicago IL

    Casual encounters - w4m - Chicago IL

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

    I’m open to anything fun