CASUAL ENCOUNTERS Chicago

397 - 408 of 457 listings
Listings
  • I really really really really love to eat pussy! - m4w - 52 - Chicago IL

    I really really really really love to eat pussy! - m4w - 52 - Chicago IL

    Men looking for Women Chicago (Illinois) September 24, 2025

    I really really really really love to eat pussy call me at seven seven three four zero three four one three eight!!!

  • HUNG HANDSUM BLK MAN FOR FUN LADY - m4w - 31 - Chicago IL

    HUNG HANDSUM BLK MAN FOR FUN LADY - m4w - 31 - Chicago IL

    Men looking for Women Chicago (Illinois) September 24, 2025

    Hello yea Im a REAL person best believe, I'm in search of a fun kool clean lady race n size dont matter looks n personality does FWB if we get along. Bout myself im clean n health hung blk man 31 single with no kids. NO MEN NO ESCORTS PLEASE.

  • 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) September 24, 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.

  • Snicker with lots of nut…wanna take a bite??? - m4w - 54 - Chicago IL

    Snicker with lots of nut…wanna take a bite??? - m4w - 54 - Chicago IL

    Men looking for Women Chicago (Illinois) September 24, 2025

    AA Male…9 inch curve DDF & Hygiene approved. Love providing and receiving oral and would love to hit them flapjacks properly til your moaning all that creamy goodness on my stride. Get at me…this squirrel ready to pump all that nut out of you and...

  • 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) September 24, 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) September 23, 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 ...

  • 37 yr older genuine woman ready for fun - w4m - 37 - Chicago IL

    37 yr older genuine woman ready for fun - w4m - 37 - Chicago IL

    Women looking for Men Chicago (Illinois) September 22, 2025

    Hello sexy Guys...... I'm online now.. Hi, I'm 37 years old woman ,but I, still wants to have a sex life. I need someone who can suck my kitty and fuck me hard. I am just looking for sex, Don’t Need Money . You can come to my place. I just hate faker...

  • 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) September 22, 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...

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

    Casual nsa/fwb - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) September 21, 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) September 21, 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...

  • Grandpa - w4m - 33 - Chicago IL

    Grandpa - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) September 21, 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

  • 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) September 21, 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...