CASUAL ENCOUNTERS Chicago

445 - 456 of 459 listings
Listings
  • Bi Male looking for hung men for NSA fun - 39 - Chicago IL

    Bi Male looking for hung men for NSA fun - 39 - Chicago IL

    Men looking for Men Chicago (Illinois) November 22, 2025

    Bi white male, 39, 5' 8", medium build, clean cut, well endowed, bubble butt. Masculine, clean & well groomed, STD/HIV negative, D/D free, non smoker, DL, discreet. Educated, sane, down to earth, local, open minded/versatile, fun to be with.

  • Ready for some fun and excitement - w4m - 25 - Chicago IL

    Ready for some fun and excitement - w4m - 25 - Chicago IL

    Women looking for Men Chicago (Illinois) November 21, 2025

    Hey! I’m available for some fun and excitement. I’m super clean and can bare back. I enjoy kissing cuddling and I can also squirt if you play the game well. Let’s meet and have a great time together

  • 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) November 21, 2025

    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'm looking for a dude to meet for sex who will eat my pussy - w4m - 21 - Chicago IL

    I'm looking for a dude to meet for sex who will eat my pussy - w4m - 21 - Chicago IL

    Women looking for Men Chicago (Illinois) November 21, 2025

    I'm looking for a dude to meet for sex who will eat my pussy. I want to find a guy for sexual meetings a couple of times a week, who loves and knows how to eat pussy. I am 21 years old. You must be of age, adequate, clean, and of course, you must lov...

  • ANY HUNG MAN AVAILABLE ? - w4m - 44 - Chicago IL

    ANY HUNG MAN AVAILABLE ? - w4m - 44 - Chicago IL

    Women looking for Men Chicago (Illinois) November 20, 2025

    Hey, I am 44 yrs old very horny & looking for someone to come over eat my pussy and f**k me well. Must be hot and willing to come to and able to make me cum. Interested person contact me

  • Grandpa - w4m - 33 - Chicago IL

    Grandpa - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) November 19, 2025

    33 submissive white female looking for a grandpa that wants to play with and breed his granddaughters tight pussy. Spoil me grandpa and you can do whatever you want to this tight pussy

  • Casual Hotel Fun - m4c - 36 - Chicago IL

    Casual Hotel Fun - m4c - 36 - Chicago IL

    Men looking for Crossdressers Chicago (Illinois) November 19, 2025

    Looking for some occasional fun with a straight married man? Are you in the Chicagoland area? Are you skinny? If so, and you are interested, hit me up with a few pics and hopefully we can get a coffee and figure out what hotel we want to book lol.

  • Sexy CD Bottom White Shaved Ass Sissy is Looking For a Top in South Suburb - c4m -Chicago IL

    Sexy CD Bottom White Shaved Ass Sissy is Looking For a Top in South Suburb - c4m -Chicago IL

    Crossdresser looking for Men Chicago (Illinois) November 19, 2025

    Hi, I am a sexy CD bottom, white, safe, clean, great hygiene, shaved smooth legs and ass, I am looking for a top. Educated, I have a Bachelor of Arts degree in Cockology (major in sucking and licking). I can host with advance notice. I can travel. Op...

  • Casual nsa/fwb - m4w - 37 - Chicago IL

    Casual nsa/fwb - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) November 19, 2025

    Just like the title says. LOL Please send a picture or two if you're interested and please live in the Chicagoland area! I can travel. I don't discriminate on age, race Etc. Please be clean and let's both be respectful! Interested in average to skinn...

  • GWM sks GL Clean-Cut Guy with great feet-Put Your Feet in my Face! - m4m - 62 - Chicago IL

    GWM sks GL Clean-Cut Guy with great feet-Put Your Feet in my Face! - m4m - 62 - Chicago IL

    Men looking for Men Chicago (Illinois) November 19, 2025

    An exceptional opportunity for a clean-cut, professional-type GL man with sexy feet who knows how to use them. Are you a good-looking, intelligent, witty, str8, bi or gay professional/entrepreneur/artist who likes to be the center of attention? Do yo...

  • Looking for some fun. NSA or FWB - w4m - 27 - Chicago IL

    Looking for some fun. NSA or FWB - w4m - 27 - Chicago IL

    Women looking for Men Chicago (Illinois) November 19, 2025

    Looking for some fun. NSA or FWB

  • Local woman looking for hard sex... - w4m - 28 - Chicago IL

    Local woman looking for hard sex... - w4m - 28 - Chicago IL

    Women looking for Men Chicago (Illinois) November 19, 2025

    Local woman looking for hard sex. Love to get dirty with my naughty stockings and red lipstick.