Chicago

49 - 60 of 475 listings
Listings
  • Goddess seeking serious submissive male for long or short time relationship - w4m - 29 - Chicago IL

    Goddess seeking serious submissive male for long or short time relationship - w4m - 29 - Chicago IL

    Women looking for Men Chicago (Illinois) June 21, 2026

    I am looking for a loyal and caring man who prides himself on his dedication to serve a woman for a long term relationship caring for her needs and desires. You will find a dominant woman who will cherish you and your service to her. Hopefully you ar...

  • Straight looking to get rimmed slowly - m4m - 39 - Chicago IL

    Straight looking to get rimmed slowly - m4m - 39 - Chicago IL

    Men looking for Men Chicago (Illinois) June 21, 2026

    Would like to find a regular older experienced guy who likes to rim. 39 years old here. Smooth and clean everywhere. Very discreet. If you’re older, experienced and can host, hit me up. I come over, bend over and you can take your time. Maybe play so...

  • Wet black pussy - w4m - 46 - Chicago IL

    Wet black pussy - w4m - 46 - Chicago IL

    Women looking for Men Chicago (Illinois) June 21, 2026

    Big horny clit and full wet pussy lips

  • Fwb - m4w - 32 - Chicago IL

    Fwb - m4w - 32 - Chicago IL

    Men looking for Women Chicago (Illinois) June 20, 2026

    What's up I'm Jay I'm 32 6 foot and 170 pounds from the south side of Chicago I'm looking for a friend to kick it with smoke drink eat watch a few shows and have some fun I love eating coochie from the back and driving this long hard wood deep in you...

  • Are You a VGL PROFESSIONAL GUY/GRAD STUDENT WITH GREAT FEET? - m4m - 58 - Chicago IL

    Are You a VGL PROFESSIONAL GUY/GRAD STUDENT WITH GREAT FEET? - m4m - 58 - Chicago IL

    Men looking for Men Chicago (Illinois) June 20, 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 man or graduate student who enjoys having his bare feet massaged, smelled and worshiped while he reads, works, texts, does work at ho...

  • Hosting in South Shore - m4w - 33 - Chicago IL

    Hosting in South Shore - m4w - 33 - Chicago IL

    Men looking for Women Chicago (Illinois) June 19, 2026

    Light skinned mixed with tattoos and big thick ???? contact me if interested serious inquiries only nothing is free. 312-802-8358

  • 42/y lonely women - w4m - 42 - Chicago IL

    42/y lonely women - w4m - 42 - Chicago IL

    Women looking for Men Chicago (Illinois) June 19, 2026

    My husband will have no part in this and he will NOT know.I am looking for someone. I am open-minded.

  • Seeking a friend, companion and lover, long or short term - m4w - 68 - Chicago IL

    Seeking a friend, companion and lover, long or short term - m4w - 68 - Chicago IL

    Men looking for Women Chicago (Illinois) June 19, 2026

    I am a 68 year old gentleman seeking a friend, companion and lover, long or short term. Age and race are non-important. I just want to make a lady happy again. No "hookups" or website referrals, please!

  • Casual encounters - w4m - Chicago IL

    Casual encounters - w4m - Chicago IL

    Women looking for Men Chicago (Illinois) June 19, 2026

    I’m open to anything fun

  • Orgy - mw4t - 37/39 - Chicago IL

    Orgy - mw4t - 37/39 - Chicago IL

    Couples looking for Trans Chicago (Illinois) June 19, 2026

    My wife and I are looking for 8 or more well endowed black and Latina transgender women who are top only to come and spend from a few days to a couple of weeks DOMINATING us from both ends at all angles

  • Group Fun - m4g - Chicago IL

    Group Fun - m4g - Chicago IL

    Men looking for Group Chicago (Illinois) June 19, 2026

    Looking for any interested guys and a female for a fun casual hotel sex fun evening. No guy on guy. Needs to be discrete, safe, healthy but fun. May even look into an escort. HMU if anyone interested. Age, looks, size don’t matter; just need to be a ...

  • Virgin guy looking for anything - m4w - 20 - Chicago IL

    Virgin guy looking for anything - m4w - 20 - Chicago IL

    Men looking for Women Chicago (Illinois) June 19, 2026

    20 year old virgin. Down for whatever you want. Cannot host, but willing to meet up. Contact me at (312) 919-9345