CASUAL ENCOUNTERS Chicago

49 - 60 of 448 listings
Listings
  • freinds with benefits chicago southwest suburbs - m4w - 40 - Chicago IL

    freinds with benefits chicago southwest suburbs - m4w - 40 - Chicago IL

    Men looking for Women Chicago (Illinois) June 1, 2026

    Lets link up for a coffee or a wine, and take it from there

  • 38 AA MALE LOOKING TO HAVE SOME FUN - m4w - 38 - Chicago IL

    38 AA MALE LOOKING TO HAVE SOME FUN - m4w - 38 - Chicago IL

    Men looking for Women Chicago (Illinois) June 1, 2026

    I am a 38 year old african american male looking for some casual fun with a female who is interested in the same. Reach me at (224) 407-5660 for more information.

  • Mrs.- w4w - 41 - Chicago IL

    Mrs.- w4w - 41 - Chicago IL

    Women looking for Women Chicago (Illinois) June 1, 2026

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

  • Innocent Latina - w4m - 19 - Chicago IL

    Innocent Latina - w4m - 19 - Chicago IL

    Women looking for Men Chicago (Illinois) June 1, 2026

    Looking for a man who want to have a good time with me

  • Amazing affair - m4w - 34 - Chicago IL

    Amazing affair - m4w - 34 - Chicago IL

    Men looking for Women Chicago (Illinois) June 1, 2026

    Just like the title says, just looking for an amazing affair. Please don't get it wrong in not looking to change your status or mine for that matter. Just looking to bring back what's no longer there. You know, the surprise, the butterflies, the fun ...

  • 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) June 1, 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) June 1, 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) June 1, 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) June 1, 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) June 1, 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) June 1, 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...

  • ARE YOU A GREAT LOOKING YOUNGER GUY WITH GREAT FEET ? - m4m - 58 - Chicago IL

    ARE YOU A GREAT LOOKING YOUNGER GUY WITH GREAT FEET ? - m4m - 58 - Chicago IL

    Men looking for Men Chicago (Illinois) May 31, 2026

    I am a 58 year old GWM who wants to worship, smell and submit to the bare feet of young, good looking professional men and graduate students who enjoy having their bare feet massaged, smelled and worshiped while they read, work, text, do work at home...