Chicago

445 - 456 of 482 listings
Listings
  • 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...

  • 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

  • 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) April 16, 2026

    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 Hotel Fun - m4c - 36 - Chicago IL

    Casual Hotel Fun - m4c - 36 - Chicago IL

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

    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.

  • 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) April 16, 2026

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

  • 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) April 16, 2026

    Looking for some fun. NSA or FWB

  • Grandpa - w4m - 33 - Chicago IL

    Grandpa - w4m - 33 - Chicago IL

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

    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 nsa/fwb - m4w - 37 - Chicago IL

    Casual nsa/fwb - m4w - 37 - Chicago IL

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

    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...

  • Young Married Unhappy At Home - w4m - 28 - Chicago IL

    Young Married Unhappy At Home - w4m - 28 - Chicago IL

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

    I am not getting what I need at home.I'm looking to have an ongoing affair with a discreet man. No feelings, just fun. I have no intentions of leaving my husband. Shoot me Interested? Then contact me here. Serious inquiries only!

  • Big clit fun - w4m - Chicago IL

    Big clit fun - w4m - Chicago IL

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

    Come pull, slap, suck, and jerk my big clit

  • Big black clit - w4m - 46 - Chicago IL

    Big black clit - w4m - 46 - Chicago IL

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

    Ebony female with full wet pussy lips and big clit. Suck my big dark areolas