CASUAL ENCOUNTERS Chicago

193 - 204 of 450 listings
Listings
  • Looking for females for couple - mw4w - 38/36 - Chicago IL

    Looking for females for couple - mw4w - 38/36 - Chicago IL

    Couples looking for Women Chicago (Illinois) October 13, 2026

    Couple looking for a women for a nice adventure. No guys sorry not intrested. Please reply with a pic. Thanks.

  • 58 yr old male looking for hung males and couples in need of 8in thick cock - m4mw - 58 - Chicago IL

    58 yr old male looking for hung males and couples in need of 8in thick cock - m4mw - 58 - Chicago IL

    Men looking for Couples Chicago (Illinois) October 13, 2026

    58 year old white male slim build 6ft tall 185lbs 8 inches cut and thick very tight asshole looking for hung males or couples open for anything. Sorry can't host but can travel local DDF HIV NEG MALES MUST BE 7+

  • BBC BULL for Couples - m4mw - 28 - Chicago IL

    BBC BULL for Couples - m4mw - 28 - Chicago IL

    Men looking for Couples Chicago (Illinois) October 13, 2026

    I am a tall, attractive and very well endowed BBC BULL looking for a couple interested in BBC. . I am 9.5 inches long and as thick as your wrist. I am real, dependable and available. I love ladies in stockings and heels.

  • Seeking my first encounter with a woman - w4w - 19 - Chicago IL

    Seeking my first encounter with a woman - w4w - 19 - Chicago IL

    Women looking for Women Chicago (Illinois) October 13, 2026

    Hi I'm a young bi curious girl. Looking to be with a woman for the first time. I'd love for you to play with me and then some. Need to keep this a secret. Thanks.

  • I need a pillow princess I can fuck often - w4w - 33 - Chicago IL

    I need a pillow princess I can fuck often - w4w - 33 - Chicago IL

    Women looking for Women Chicago (Illinois) October 13, 2026

    I’m lesbian, so men and couples don't waste time. Looking to meet a lesb/bi girl I can get to know hangout with and sexually please. I love giving oral and making u moan cumm. If u like toys I have vibrators and dildos Looking to meet today No men, w...

  • 50 yo fit visitor looking for hot NSA in my hotel room - m4m - 50 - Chicago IL

    50 yo fit visitor looking for hot NSA in my hotel room - m4m - 50 - Chicago IL

    Men looking for Men Chicago (Illinois) October 13, 2026

    6' 200 lbs muscular and hairy...fit and fucking horny. I get into a lot of stuff mild to wild...no pain for me but I will give it...just looking to get naked with another man around my age or older. Nasty fuckers are cool. No scat. In Sheraton downto...

  • Single open minded submissive white guy - m4w - 32 - Chicago IL

    Single open minded submissive white guy - m4w - 32 - Chicago IL

    Men looking for Women Chicago (Illinois) October 13, 2026

    I’m single, 32, with no kids. I’m open minded and ok with the woman being with other men as well ina relationship

  • Erotic baby doll next door - w4m - 27 - Chicago IL

    Erotic baby doll next door - w4m - 27 - Chicago IL

    Women looking for Men Chicago (Illinois) October 13, 2026

    I am single sexy girl. Any boys want to come over and have some fun, stress relief. No drama, no games,100% real & looking for a real person to have a good time.

  • NSA FWB - Younger seeks older milf - m4w - 27 - Chicago IL

    NSA FWB - Younger seeks older milf - m4w - 27 - Chicago IL

    Men looking for Women Chicago (Illinois) October 13, 2026

    Searching for an older woman. I want you to take control of the bedroom and I’ll give you what you want. I eat pussy and can be as kinky as you want. NSA, FWB, MBA I’m 27, straight, 6’ 7”+ thick. Chicago proper, can’t host

  • Looking for a fun kinky couple - m4mw - 49 - Chicago IL

    Looking for a fun kinky couple - m4mw - 49 - Chicago IL

    Men looking for Couples Chicago (Illinois) October 13, 2026

    Looking for a fun kinky couple couple. I’m a good looking WM 49 yo, 7” and very thick. I really get off to having sex with another’s mans girl with him or him watching I’m looking for a laid back couple that likes to have fun. Your pics will get mine...

  • Female Looking For Male - w4m - 35 - Chicago IL

    Female Looking For Male - w4m - 35 - Chicago IL

    Women looking for Men Chicago (Illinois) October 13, 2026

    35 year old female looking for that someone special. Come see me tonight ill make all your fantasies come true. Im a hot woman 35 year old looking for fun. Hnu

  • open minded - m4mw - 32 - Chicago IL

    open minded - m4mw - 32 - Chicago IL

    Men looking for Couples Chicago (Illinois) October 13, 2026

    Well Educated, respectful, clean, fit and Handsome single male looking to meet like-minded couples. It is my first time and love to meet a down to earth couple. Can host but willing to travel too. No endless emails and send a pic to verify you are re...