CASUAL ENCOUNTERS Chicago

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  • Bear Looking To Pound and More - m4m - 36 - Chicago IL

    Bear Looking To Pound and More - m4m - 36 - Chicago IL

    Men looking for Men Chicago (Illinois) September 26, 2026

    Bear male in Chicago looking in city or Surrounding for oral, anal, spanking, eating ass, shower play or more. Cannot host but can come. 5’10” 240 black hair dark brown eyes can be your daddy or big bro love roleplay and mild to wild

  • Miss peaches! - w4m - 33 - Chicago IL

    Miss peaches! - w4m - 33 - Chicago IL

    Women looking for Men Chicago (Illinois) September 26, 2026

    Gorgeous blonde staying downtown for a few weeks. Email me for further info. I look forward to hearing from you. Xoxo

  • Black pussy for cum dumping - w4m - 45 - Chicago IL

    Black pussy for cum dumping - w4m - 45 - Chicago IL

    Women looking for Men Chicago (Illinois) September 25, 2026

    Who wants to suck and fuck some sexy black pussy, tongue fuck my wet pink hole and suck on my big chocolate areolas . Beat my black pussy up

  • Single mom need discreet Hook - w4m - 37 - Chicago IL

    Single mom need discreet Hook - w4m - 37 - Chicago IL

    Women looking for Men Chicago (Illinois) September 24, 2026

    I am looking for a man between25-46 to have very discreet sexy time with. I am bored at work and looking for a toy to play with when I go home for lunch. I Can host. Not looking for drama and not looking to cause drama. Just want some action. Text me

  • Treat me like a princess - w4m - 27 - Chicago IL

    Treat me like a princess - w4m - 27 - Chicago IL

    Women looking for Men Chicago (Illinois) September 24, 2026

    Open doors for me. Use words like please and thank you. Tell me I look beautiful. Thats pretty much all I ask for in return for a night that you wont soon forget. I am not here to be used and thrown away, I am here for a night of passion and pleasure...

  • 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, 2026

    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

  • Pleasure to meet you - m4w - Chicago IL

    Pleasure to meet you - m4w - Chicago IL

    Men looking for Women Chicago (Illinois) September 24, 2026

    I want to pleasure your mind. Lick you pussy. Massage your body. Listen to you speak. And fuck till we drop

  • YOUNG PROF MEN/GRAD STUDENTS- YOUR FEET ARE YOUR BEST ASSET - m4m - 58 - Chicago IL

    YOUNG PROF MEN/GRAD STUDENTS- YOUR FEET ARE YOUR BEST ASSET - m4m - 58 - Chicago IL

    Men looking for Men Chicago (Illinois) September 24, 2026

    I am a 58 year old GWM who wants to worship, smell and submit to the bare feet of a young, good looking professional Caucasian man or graduate student who enjoys having his bare feet massaged, smelled and worshiped while he reads, works, texts, does ...

  • Latina woman - w4w - 37 - Chicago IL

    Latina woman - w4w - 37 - Chicago IL

    Women looking for Women Chicago (Illinois) September 22, 2026

    Hi there I'm Latina woman from Chicago lookingito explore with another woman.

  • Juicy black clit - w4m - Chicago IL

    Juicy black clit - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) September 22, 2026

    Want some wet black pussy with a big pink clit? Sexy black female with big dark nipples and a big clit

  • Good Dick Don’t Cum Often…Let Me Make That PUSSY Proud - m4w - 55 - Chicago IL

    Good Dick Don’t Cum Often…Let Me Make That PUSSY Proud - m4w - 55 - Chicago IL

    Men looking for Women Chicago (Illinois) September 22, 2026

    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...

  • Make your wish come true - w4m - 31 - Chicago IL

    Make your wish come true - w4m - 31 - Chicago IL

    Women looking for Men Chicago (Illinois) September 22, 2026

    I’m a simple girl, who like to live young wild and free