CASUAL ENCOUNTERS Chicago

229 - 240 of 452 listings
Listings
  • 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) May 18, 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) May 18, 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) May 18, 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) May 18, 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) May 18, 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

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

    Female Looking For Male - w4m - 35 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 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

  • Hot bi couple looking for the same - 37/35 - Chicago IL

    Hot bi couple looking for the same - 37/35 - Chicago IL

    Couples looking for Couples Chicago (Illinois) May 18, 2026

    Looking for kinky couples. We've both done this before in previous relationships, but its our first time doing so together. He is bi and has a thick 7' cock and great stamina. She is bi, not timid at all, and knows how to give pleasure. Send us some ...

  • Young couple looking fun - mw4mw - 22/20 - Chicago IL

    Young couple looking fun - mw4mw - 22/20 - Chicago IL

    Couples looking for Couples Chicago (Illinois) May 18, 2026

    Looking for fun for me and my gf so looking for another couple or a single female. NO SINGLE MEN

  • New experiences - m4mw - 37 - Chicago IL

    New experiences - m4mw - 37 - Chicago IL

    Men looking for Couples Chicago (Illinois) May 18, 2026

    Looking to try something new and get a experience of a life time that I wont ever forget. So hit me uo please

  • Looking for the right ones - w4m - 46 - Chicago IL

    Looking for the right ones - w4m - 46 - Chicago IL

    Women looking for Men Chicago (Illinois) May 18, 2026

    I'm a black SSBBW. Female 46, 500lbs looking for a shy white male for relationship. No smokers & drinkers between 35 to 45 years old. Must like dominate woman. Bi sexual is ok, but Im really looking for that shy male who wants a strong woman for ...

  • Married and bored! - w4w - 38 - Chicago IL

    Married and bored! - w4w - 38 - Chicago IL

    Women looking for Women Chicago (Illinois) May 18, 2026

    My husband is a over the road truck driver so I'm left lonely at times when I'm not working. Yearning for the taste of a woman! I love curious women. They are the freakiest. Lol. I'm very oral....and experienced. Enjoy traveling and enjoying life. Sh...

  • Married couple looking for another couple - mw4mw - 50/48 - Chicago IL

    Married couple looking for another couple - mw4mw - 50/48 - Chicago IL

    Couples looking for Couples Chicago (Illinois) May 18, 2026

    We're fun outgoing I have lots of tattoos and we want to try something new we want to try a couples swap