CASUAL ENCOUNTERS Chicago

25 - 36 of 457 listings
Listings
  • sissy CD for hot guys - c4m - Chicago IL

    sissy CD for hot guys - c4m - Chicago IL

    Crossdresser looking for Men Chicago (Illinois) August 15, 2025

    horny sissy for hung guys, love to give long bj and get kisses, slaps and licks.

  • BBC for fun tonight - m4w - Chicago IL

    BBC for fun tonight - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) August 12, 2025

    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

  • Miss peaches! - w4m - 33 - Chicago IL

    Miss peaches! - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) August 12, 2025

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

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

    Alone and need company - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) August 12, 2025

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

  • 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) August 12, 2025

    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!!!

  • Jus a young man tryna have fun - m4w - 20 - Chicago IL

    Jus a young man tryna have fun - m4w - 20 - Chicago IL

    Men looking for Women Chicago (Illinois) August 12, 2025

    Jus tryna make friends go out n have a lil extra fun

  • 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) August 11, 2025

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

  • Garrett - m4w - Chicago IL

    Garrett - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) August 11, 2025

    Easygoing guy with a sincere heart and a good sense of humor looking for independent, fun, sexually attentive female for nsa casual relationship. I am 6' , 215 lbs and enjoy intense foreplay with mutual oral pleasure. I would love to make it worth yo...

  • 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) August 11, 2025

    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.

  • Innocent Latina - w4m - Chicago IL

    Innocent Latina - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) August 11, 2025

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

  • Mrs.- w4w - 41 - Chicago IL

    Mrs.- w4w - 41 - Chicago IL

    Women looking for Women Chicago (Illinois) August 11, 2025

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

  • Amazing affair - m4w - 34 - Chicago IL

    Amazing affair - m4w - 34 - Chicago IL

    Men looking for Women Chicago (Illinois) August 11, 2025

    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 ...