CASUAL ENCOUNTERS Chicago

49 - 60 of 449 listings
Listings
  • Group Fun - m4g - Chicago IL

    Group Fun - m4g - Chicago IL

    Men looking for Group Chicago (Illinois) June 19, 2026

    Looking for any interested guys and a female for a fun casual hotel sex fun evening. No guy on guy. Needs to be discrete, safe, healthy but fun. May even look into an escort. HMU if anyone interested. Age, looks, size don’t matter; just need to be a ...

  • Virgin guy looking for anything - m4w - 20 - Chicago IL

    Virgin guy looking for anything - m4w - 20 - Chicago IL

    Men looking for Women Chicago (Illinois) June 19, 2026

    20 year old virgin. Down for whatever you want. Cannot host, but willing to meet up. Contact me at (312) 919-9345

  • Horny Girl Wanna Oral Love - w4m - 23 - Chicago IL

    Horny Girl Wanna Oral Love - w4m - 23 - Chicago IL

    Women looking for Men Chicago (Illinois) June 19, 2026

    Hey guys I m a single sexy female just trying to have somefun tonight and fulfill your fantasy SEXT me. text me >

  • Key - m4w - 32 - Chicago IL

    Key - m4w - 32 - Chicago IL

    Men looking for Women Chicago (Illinois) June 19, 2026

    Looking for casual encounter

  • Chocolate creme filled 37yr old female - w4m - 37 - Chicago IL

    Chocolate creme filled 37yr old female - w4m - 37 - Chicago IL

    Women looking for Men Chicago (Illinois) June 19, 2026

    Hot sexy chocolate creme filled lusciously built willing and able brown skinned woman wide open now excepting loads!

  • Bbc seeks fun - m4w - 37 - Chicago IL

    Bbc seeks fun - m4w - 37 - Chicago IL

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

    Black male on the north side of the city looking for fun. I can host if needed. No issues with age or race. Please send a pic. Please don't waste time responding if you don't intend to meet.

  • Woman - w4m - Chicago IL

    Woman - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) June 17, 2026

    I love sex I love giving blow jobs My favorite is having sex with two or 3 guys at the same time… or even having sex and giving blowjobs while someone else watches! HMU let’s have some fun.

  • ANON RAW CUM DUMP searching for tops - m4m - 49 - Chicago IL

    ANON RAW CUM DUMP searching for tops - m4m - 49 - Chicago IL

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

    Horny, age 49, GWM bttm, 6'2", 235, is looking to host a raw top ANON into my northside apartment. My door unlocked. You find me on all fours, face down, ass up and spread. Fuck me till you cum in my hot tight ass, then take off. No small talk. Just ...

  • I am a gay male Looking to pay a straight man to do gay things - m4m - Chicago IL

    I am a gay male Looking to pay a straight man to do gay things - m4m - Chicago IL

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

    I am a man not s women Pics upfront either show me what ya look like or I'll delete the chat. I host I need a straight guy, age between 21 and 50. No gay men, no transsexuals just straight men. I want to have you watch me jerk off naked with my ass i...

  • Looking for guys who cum huge loads - m4m - 34 - Chicago IL

    Looking for guys who cum huge loads - m4m - 34 - Chicago IL

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

    Looking to meet men in Illinois who cum a lot to meet me in public get their dick sucked and cum a massive load on my fave and leave. I have pics so just text me do bot blind call me

  • Wild and horny - m4w - 36 - Chicago IL

    Wild and horny - m4w - 36 - Chicago IL

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

    Hello hot sexy womans and girls. I love sex and womans if someone wants pleasure and wild ride HMU at: blackwildharley@gmail.com Snapchat: wildsteve

  • I can take pictures or video - m4mw - Chicago IL

    I can take pictures or video - m4mw - Chicago IL

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

    Hello I would love to watch a couple have sex and if interested I can record both of you in your best scene for your collection. Im open to participate also.