CASUAL ENCOUNTERS Chicago

61 - 72 of 452 listings
Listings
  • Mrs.- w4w - 41 - Chicago IL

    Mrs.- w4w - 41 - Chicago IL

    Women looking for Women Chicago (Illinois) July 29, 2026

    41 years old f looking for female/couples to have fun in Chicago area

  • Woman touch - w4w - Chicago IL

    Woman touch - w4w - Chicago IL

    Women looking for Women Chicago (Illinois) July 29, 2026

    Latina woman looking to have some good time with another woman.

  • Looking for guys to cream on these(46ddd tits - m4m - 42 - Chicago IL

    Looking for guys to cream on these(46ddd tits - m4m - 42 - Chicago IL

    Men looking for Men Chicago (Illinois) July 29, 2026

    I'm a male looking for guys and transgenders and crossdressers to cream on these big boobs.love hot white cream.send me a message soon.Love all size cocks.

  • Unhappy horny mom looking for roommm - w4m - 28 - Chicago IL

    Unhappy horny mom looking for roommm - w4m - 28 - Chicago IL

    Women looking for Men Chicago (Illinois) July 29, 2026

    Hey..!I'm emily.28years women looking free & good minded man,wanttofull sex without condom. fun, lets talk and see what we think. Please serious inquiries only!!!

  • Alone and need company - w4m - 31 - Chicago IL

    Alone and need company - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) July 29, 2026

    Hey guys! If you want to come over and have some fun. You must be clean and respectful. Text Me

  • Bear Looking To Pound and More - m4m - 36 - Chicago IL

    Bear Looking To Pound and More - m4m - 36 - Chicago IL

    Men looking for Men Chicago (Illinois) July 29, 2026

    Bear male in Chicago looking in city or Surrounding for oral, anal, spanking, eating ass, shower play or more. Cannot host but can come. 5’10” 240 black hair dark brown eyes can be your daddy or big bro love roleplay and mild to wild

  • Miss peaches! - w4m - 33 - Chicago IL

    Miss peaches! - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) July 29, 2026

    Gorgeous blonde staying downtown for a few weeks. Email me for further info. I look forward to hearing from you. Xoxo

  • Sexy brunette - w4m - 29 - Chicago IL

    Sexy brunette - w4m - 29 - Chicago IL

    Women looking for Men Chicago (Illinois) July 29, 2026

    Hey guys, I'm Ashly brown 29 years old brunette girl looking to have some fun with a hot guy, maybe multiple. I'm super horny right now. I'm 5'7 and 135 lbs skinny. Pretty big tits too. Send me a and i'll send one back ;) thanks! Let's get this going...

  • Down for anything - m4w - Chicago IL

    Down for anything - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) July 28, 2026

    Looking for women who don’t charge for sex lets b real honest. I am 37 white/hispanic male who is down for anything sexually as long as your clean. I love women of all shapes sizes and colors. I love to eat pussy and ass even from the back. Willing t...

  • 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) July 27, 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

  • Single mom need discreet Hook - w4m - 37 - Chicago IL

    Single mom need discreet Hook - w4m - 37 - Chicago IL

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

    I am looking for a man between25-46 to have very discreet sexy time with. I am bored at work and looking for a toy to play with when I go home for lunch. I Can host. Not looking for drama and not looking to cause drama. Just want some action. Text me

  • Treat me like a princess - w4m - 27 - Chicago IL

    Treat me like a princess - w4m - 27 - Chicago IL

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

    Open doors for me. Use words like please and thank you. Tell me I look beautiful. Thats pretty much all I ask for in return for a night that you wont soon forget. I am not here to be used and thrown away, I am here for a night of passion and pleasure...