CASUAL ENCOUNTERS Chicago

253 - 264 of 459 listings
Listings
  • W/F looking for sex no kinky things - w4m - 57 - Chicago IL

    W/F looking for sex no kinky things - w4m - 57 - Chicago IL

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

    Like to touch play with the oils like to kiss lick ride and like oral sex an actual penetration sex nothing kinky but open-minded to something I don't butt f*** so don't ask me

  • Feeling the need to get naughty - mw4mw 55/54 - Chicago IL

    Feeling the need to get naughty - mw4mw 55/54 - Chicago IL

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

    We are looking for a like minded couple that wants to have some wild, and kinky fun. No hang-ups, just fun. Single, strait guys need not reply. You would be wasting your time, and ours.

  • Real female 48 look younger - w4m - 48 - Chicago IL

    Real female 48 look younger - w4m - 48 - Chicago IL

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

    Seeking sensual experiences with safe sane sexy intelligent male. 420 a nice idea, social drinking ok. Cigarettes a no go. I’m curvy, attractive, hot and open minded

  • Hot couple looking for oral fun now - mw4m - 36/35 - Chicago IL

    Hot couple looking for oral fun now - mw4m - 36/35 - Chicago IL

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

    Hot couple looking for oral fun now... Hit us back, were ready now Seeking single men and other hot couples

  • May 4th - Early 40’s Couple Looking for Straight Guy - mw4m - 47/43 - Chicago IL

    May 4th - Early 40’s Couple Looking for Straight Guy - mw4m - 47/43 - Chicago IL

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

    Long time married, good looking, professional, straight, white couple in our early 40’s that will be in Chicago the night of Saturday, May 4th. We are looking to have some threesome fun with a well hung straight guy. My wife is a very good looking bl...

  • 2 females looking for one guy - g4m - Chicago IL

    2 females looking for one guy - g4m - Chicago IL

    Group looking for Men Chicago (Illinois) April 18, 2026

    we are two female here we are looking for a playmate that who can fuck long time. We have large breasts and large ass. Please be ddf as we are and reply with a picture can be g rated

  • College guy looking for top - m4m - 24 - Chicago IL

    College guy looking for top - m4m - 24 - Chicago IL

    Men looking for Men Chicago (Illinois) April 18, 2026

    Pretty new being a bottom but I love it, I'm a bit tight but that just makes it feel better when your rough. Come bend me over and fuck this white boys ass.

  • Hot couple - mw4m - 24/22 - Chicago IL

    Hot couple - mw4m - 24/22 - Chicago IL

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

    We are joung coup open minded Open for everything Send us a massage

  • Looking for a open mind guy for a threesome - mw4m - 33/31 - Chicago IL

    Looking for a open mind guy for a threesome - mw4m - 33/31 - Chicago IL

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

    Hey there we are a couple looking for a open mind guy who wants to have fun with my girl and me we try to make a threesome for more info contact me if you are interested let me know

  • Looking for big tits - m4w - 51 - San Antonio TX

    Looking for big tits - m4w - 51 - San Antonio TX

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

    Any women like having their big tits sucked, licked, nipples played with and possibly fucked with a thick load on them? Just want something like that today, doesn’t have to be more.

  • Couple for girl - mw4w - 32/30 - Chicago IL

    Couple for girl - mw4w - 32/30 - Chicago IL

    Couples looking for Women Chicago (Illinois) April 18, 2026

    PLEASE READ AD BEFORE REPLYING We are a Latin couple F-30 5'2 M-32 5'7 looking for a girl/female/woman. Someone who has a vagina between their legs not a dick. We are ok with one time or ongoing if we all click. Bi++++. If your not bi it's not a deal...

  • Spring break fun - w4m - 22 - Chicago IL

    Spring break fun - w4m - 22 - Chicago IL

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

    Hey, I'm here in town for spring break. I am 22 years young, tall (5'11) slim, and mixed with freckled. Im looking to meet some very respectable men or Daddies. I have a suite in downtown Chicago and will be hosting. I'm open to a partying while in t...