CASUAL ENCOUNTERS Chicago

13 - 24 of 457 listings
Listings
  • single and attractive - w4m - 24 - Chicago IL

    single and attractive - w4m - 24 - Chicago IL

    Women looking for Men Chicago (Illinois) May 3, 2026

    I'm single and attractive and haven't let my freak out in a while. I just wanna get my freak on lol. If you love to bury your face in a beautiful clean soft tight pussy. If u are interested text me soon.......I can host if you are serious

  • Bbc seeks fun - m4w - 37 - Chicago IL

    Bbc seeks fun - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) May 3, 2026

    Black male on the north side of the city looking for fun. I can host if needed. No issues with age or race. Please send a pic. Please don't waste time responding if you don't intend to meet.

  • DEVIN AVAIL NOW - m4m - 29 - Chicago IL

    DEVIN AVAIL NOW - m4m - 29 - Chicago IL

    Men looking for Men Chicago (Illinois) May 2, 2026

    Looking for Nice guys to spend some time with Fully verse And Have great Sex Let me be your boyfriend for tonight I am available now I am hosting on the south side I can host only out all if u uber me to your place

  • 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) May 2, 2026

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

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

    Alone and need company - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) May 2, 2026

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

  • Sexy brunette - w4m - 29 - Chicago IL

    Sexy brunette - w4m - 29 - Chicago IL

    Women looking for Men Chicago (Illinois) May 2, 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) May 2, 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!!!

  • 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) May 2, 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

  • Innocent Latina - w4m - Chicago IL

    Innocent Latina - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) May 2, 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) May 2, 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 ...

  • Miss peaches! - w4m - 33 - Chicago IL

    Miss peaches! - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) May 2, 2026

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

  • 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) May 2, 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.