CASUAL ENCOUNTERS Chicago

37 - 48 of 455 listings
Listings
  • 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) October 25, 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.

  • Sexy brunette - w4m - 29 - Chicago IL

    Sexy brunette - w4m - 29 - Chicago IL

    Women looking for Men Chicago (Illinois) October 25, 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...

  • 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) October 25, 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!!!

  • Innocent Latina - w4m - 19 - Chicago IL

    Innocent Latina - w4m - 19 - Chicago IL

    Women looking for Men Chicago (Illinois) October 25, 2026

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

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

    Alone and need company - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) October 25, 2026

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

  • Amazing affair - m4w - 34 - Chicago IL

    Amazing affair - m4w - 34 - Chicago IL

    Men looking for Women Chicago (Illinois) October 25, 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 ...

  • 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) October 25, 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

  • 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) October 25, 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.

  • Miss peaches! - w4m - 33 - Chicago IL

    Miss peaches! - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) October 25, 2026

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

  • Mrs.- w4w - 41 - Chicago IL

    Mrs.- w4w - 41 - Chicago IL

    Women looking for Women Chicago (Illinois) October 25, 2026

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

  • Black Magic - m4w - 35 - Chicago IL

    Black Magic - m4w - 35 - Chicago IL

    Men looking for Women Chicago (Illinois) October 25, 2026

    Lets have some fun!

  • BBC for fun tonight - m4w - Chicago IL

    BBC for fun tonight - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) October 24, 2026

    Black male on the north side of the city looking for a woman to have fun with today. Open to all races. Please send a pic. Please respond if you’re serious about meeting.Thanks. onlyj85 k I k