CASUAL ENCOUNTERS Chicago

121 - 132 of 448 listings
Listings
  • Married couple in 40’s looking for couple for fun - mw4mw - 44/42 - Chicago IL

    Married couple in 40’s looking for couple for fun - mw4mw - 44/42 - Chicago IL

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

    We are a married couple in our 40’s looking for couple for fun times in and out of the bedroom. Experienced here. Clean, discreet, D/D Free!! She is shy at first but warms up quickly. We enjoy playing together as well as alone separate rooms can be g...

  • Looking for a toy - mw4m - 35/32 - Chicago IL

    Looking for a toy - mw4m - 35/32 - Chicago IL

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

    My man and I want a well endowed male to meet us for some fun. We are looking for a good long fat cock not over 45.

  • Hot Sexy Girl For Your Dick - w4m - 31 - Chicago IL

    Hot Sexy Girl For Your Dick - w4m - 31 - Chicago IL

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

    I'm a 31 years old sexy girl bored and alone. I'm ready for everything. I love having fun need someone to come play with & Hookup. I am so horny and need sex. I can host. I'm 5'6" and 150 lbs. I have 34D size b00bs. You can play with my b00bs for...

  • Fuck me Hardly without condom !!!! - w4m - 28 - Chicago IL

    Fuck me Hardly without condom !!!! - w4m - 28 - Chicago IL

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

    Looking for a guy who likes to eat pussy and maybe fu…ck. Must be discreet must reply with age, description and location. Must be into my body and like to make me cUUUUm. text me

  • Looking for a freak! - mw4w - 29/27 - Chicago IL

    Looking for a freak! - mw4w - 29/27 - Chicago IL

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

    Married african american couple looking for a freak to join us in 3some. I wanna share my man and his big dick. I wanna play with your pussy too. Any race/age is welcome.

  • BBC Fun.... - mw4m - 31/31 - Chicago IL

    BBC Fun.... - mw4m - 31/31 - Chicago IL

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

    30 somethings white couple here, my GF has wanted to experiment with showing off in public and having BBC surround her. Anyone know a hidden spot she can find some action at to get her started.... Cant miss her pale white skin Strawberry Blonde hair ...

  • Black & White Couple - mw4w - 36/34 - Chicago IL

    Black & White Couple - mw4w - 36/34 - Chicago IL

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

    Sexy interracial couple, 36 black male and 34 white female looking for a female 3rd for some bedroom fun. Both open minded but know what we want. He's slim and packin 8+ she's bi and really sexy. Hit us up for fun. We host.

  • Female FWB - w4w - 41 - Chicago IL

    Female FWB - w4w - 41 - Chicago IL

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

    I'm married and mom looking for a DISCREET friendsip with a woman over 30. NO MEN NO COUPLES NO MEN NO COUPLES NO MEN NO COUPLES

  • Midnight looking for a clean and sexy girl - w4w - 24 - Chicago IL

    Midnight looking for a clean and sexy girl - w4w - 24 - Chicago IL

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

    I am looking for casual friend, no age range . I'm 24 and attractive ;) I'm clean and safe, trying new things. and expect the same. If u are interested, Te-xt me n-ow. I a-m wa-it--ing f-or y-ou.

  • Hungry Divorced MOM Looking- For A GOOD SEX- PARTNER - w4m - 33 - Chicago IL

    Hungry Divorced MOM Looking- For A GOOD SEX- PARTNER - w4m - 33 - Chicago IL

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

    Hey I am 33yrs old lonely, bored, horny, divorced mom. Looking for someone to sex with me. I am ****and need to get off. If this is you then hit me. Age no problem….

  • no strings - w4m - 32 - Chicago IL

    no strings - w4m - 32 - Chicago IL

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

    Married, attractive female looking to give a discreet, no strings blowjob I'm ready for any and everything,

  • Single Sexy Young Girl Soft Tight Pussy Wanna Fuck - w4m - 24 - Chicago IL

    Single Sexy Young Girl Soft Tight Pussy Wanna Fuck - w4m - 24 - Chicago IL

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

    I am looking for an older guy between 28-45 to be a low key fwb. I'm 24, 5'3 and pretty. Please reply with a pic!