CASUAL ENCOUNTERS Chicago

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  • Looking for a playmate - mw4w - 54/52 - Chicago IL

    Looking for a playmate - mw4w - 54/52 - Chicago IL

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

    Looking for a female to have a night of fun and uninhibited pleasure. My wife is 52 very bi and hot. I'm 54 but look very young for my age. We can host in our home. Must be clean and open to trying new things. Can be more then a one night deal if the...

  • 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) April 18, 2026

    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.

  • Erotic Discreet Ready for Ice Cream - w4m - 26 - Chicago IL

    Erotic Discreet Ready for Ice Cream - w4m - 26 - Chicago IL

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

    Party friendly social drinker love to explore. If you're my type, we'll enjoy every moment.

  • looking for a discreet third - mw4m - 54/52 - Chicago IL

    looking for a discreet third - mw4m - 54/52 - Chicago IL

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

    Couple looking to add a discreet third. Someone laid back and chilled. We are free tonight and looking to possibly hang out maybe here at the house, that way if things head in that direction we can get right to it. Anyway, looking for someone who lov...

  • BBC for fun tonight - m4w - Chicago IL

    BBC for fun tonight - m4w - Chicago IL

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

    Black male on the north side of the city looking for a woman to have fun with today. Open to all races. Please send a pic. Please respond if you’re serious about meeting.Thanks. onlyj85 k I k

  • 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) April 17, 2026

    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...

  • IF YOU R A YOUNG VGL PROF GUY/GRADUATE STUDENT-MAKE ME WORSHIP - m4m - 58 - Chicago IL

    IF YOU R A YOUNG VGL PROF GUY/GRADUATE STUDENT-MAKE ME WORSHIP - m4m - 58 - Chicago IL

    Men looking for Men Chicago (Illinois) April 17, 2026

    I am a 58 year old GWM who wants to worship, smell and submit to the bare feet of young, good looking professional men and graduate students who enjoy having their bare feet massaged, smelled and worshiped while they read, work, text, do work at home...

  • GWM would like to massage the bare feet of Young Men - m4m - Chicago IL

    GWM would like to massage the bare feet of Young Men - m4m - Chicago IL

    Men looking for Men Chicago (Illinois) April 17, 2026

    GWM ISO young, professional Caucasian men/Grad Students who want their bare feet massaged and cared for. I prefer a guy who likes having his feet massaged smelled, licked and worshiped by a mature guy. Do you enjoy a man taking care of your bare feet...

  • AA Female to Male Trans Seeking Chubby SWM with SWC for face fucking - t4m - Chicago IL

    AA Female to Male Trans Seeking Chubby SWM with SWC for face fucking - t4m - Chicago IL

    Trans looking for Men Chicago (Illinois) April 17, 2026

    Looking for a single white male older than 40 please. I mean creepy like "Motel in the middle of the night" Type creep. Not looking for Sensual or compassionate. I'm located in Edgewater, Chicago, Illinois. I DO NOT HOST. DONT ASK. My apartment was v...

  • Bbc seeks fun - m4w - 37 - Chicago IL

    Bbc seeks fun - m4w - 37 - Chicago IL

    Men looking for Women Chicago (Illinois) April 17, 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.

  • Please let me masturbate for you while we videochat asap - m4w - 30 - Chicago IL

    Please let me masturbate for you while we videochat asap - m4w - 30 - Chicago IL

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

    Im attr thin clean polite very horny ready to videochat anf il masturbate naked for you while we videochat. Can be teams or whatsapp or cell. Female only for fun only can be reg basis please hurry im ready asap my email is all lower case and is paper...

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

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

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

    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