CASUAL ENCOUNTERS Chicago

181 - 192 of 448 listings
Listings
  • Couple looking for fun - 38/36 - Chicago IL

    Couple looking for fun - 38/36 - Chicago IL

    Couples looking for Couples Chicago (Illinois) June 16, 2026

    M/F couple, into almost anything. Just looking to have some fun with others. We're in our 30's and just want to have some more fun. Tell us what you're into and send a pic of both of you. If you're into it, we probably are as well. Looking forward to...

  • Bi curious male - m4m - 55 - Chicago IL

    Bi curious male - m4m - 55 - Chicago IL

    Men looking for Men Chicago (Illinois) June 16, 2026

    55yrs bi curious male 185lbs 511 8in cut average looking medium build ddf versital open-minded tight asshole. Looking to be serviced by the biggest cock out there for my birthday on Monday you must host

  • Fuck my girlfriend - mw4m - 25/24 - Chicago IL

    Fuck my girlfriend - mw4m - 25/24 - Chicago IL

    Couples looking for Men Chicago (Illinois) June 16, 2026

    Hey guys we're a couple looking for a guy to come over for some fun. We are both really into trying different things, some kinky stuff. He has an athletic body and a great looking cock. She loves to dress up and is a real performer You must be very w...

  • Yo - m4w - 36 - Chicago IL

    Yo - m4w - 36 - Chicago IL

    Men looking for Women Chicago (Illinois) June 16, 2026

    What's up I'm a 36 year old single black man. I'm trying to kick and have fun. I like to go out and I like to chill in. I smoke(420) and I'm a casual drinker. I'm looking for my pillow princess. I'm looking for my princess period. hit me up 331-301-0...

  • Single hot female needs your big cock - w4m - 33 - Chicago IL

    Single hot female needs your big cock - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) June 16, 2026

    Hi. Single sexy AA female looking for fwb with single white male. Contact me

  • I WANT REAL HOTY AND HOT DOGGY STYLE - w4m - 26 - Chicago IL

    I WANT REAL HOTY AND HOT DOGGY STYLE - w4m - 26 - Chicago IL

    Women looking for Men Chicago (Illinois) June 16, 2026

    HELLO,,really i am so so alone, but excited because my man out of 69 days.i want a doggy style buddy..

  • Real Woman Ready to Have Fun - w4m - 37 - Chicago IL

    Real Woman Ready to Have Fun - w4m - 37 - Chicago IL

    Women looking for Men Chicago (Illinois) June 16, 2026

    I'm real and horny, open to meet guys, preferably with a big tool. I ASK FOR PICTURE (face & Tool) before we meet in person ..

  • 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) June 16, 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) June 16, 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) June 16, 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) June 16, 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) June 16, 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...