CASUAL ENCOUNTERS Chicago

133 - 144 of 452 listings
Listings
  • Quality over quantity.- w4m - 64 - Chicago IL

    Quality over quantity.- w4m - 64 - Chicago IL

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

    Does the sheer white shirt make me look cold? I promise you, it'll be steaming hot once we get started. I'm a real lady but not to be assumed to be snobby or full of myself. Let's go get a drink, let me show you what these hands are made of, and let'...

  • Seeking a man who’s into kissing, breastplay, and passionate foreplay - w4m - 26 - Chicago IL

    Seeking a man who’s into kissing, breastplay, and passionate foreplay - w4m - 26 - Chicago IL

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

    Sexy, slender, free-spirited blonde is seeking a romantic man who shares my passion for long, slow, steamy foreplay leading up to the main event. Open to all ages and races, but no married guys please. And please tell me a little bit about yourself a...

  • Wife wants to suck a stranger - w4m - 30 - Chicago IL

    Wife wants to suck a stranger - w4m - 30 - Chicago IL

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

    I'm married and need to be discreet. I've had a fantasy for a while now to suck off a complete stranger and take his load in my mouth. I don't want to have sex with you so don't ask please. Just suck you, take it in my mouth and even swallow please b...

  • Horny need sex!! - w4m - 26 - Chicago IL

    Horny need sex!! - w4m - 26 - Chicago IL

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

    I'm not ugly nor dumb but I'm lonely. Looking for average guy to spend some quality time with. I promise you won't be disappointed in becoming friends with me. For quick response. Contact me

  • Man Seeking Couples And Women - m4mw - 41 - Chicago IL

    Man Seeking Couples And Women - m4mw - 41 - Chicago IL

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

    Fun and easy going male seeks couples and women for fun times. Love pampering females, give great erotic massages with special attention to those sensitive area.

  • Married couple in 40’s looking for couple for fun - mw4mw - 44/42 - Chicago IL

    Married couple in 40’s looking for couple for fun - mw4mw - 44/42 - Chicago IL

    Couples looking for Couples Chicago (Illinois) May 18, 2026

    We are a married couple in our 40’s looking for couple for fun times in and out of the bedroom. Experienced here. Clean, discreet, D/D Free!! She is shy at first but warms up quickly. We enjoy playing together as well as alone separate rooms can be g...

  • Looking for a toy - mw4m - 35/32 - Chicago IL

    Looking for a toy - mw4m - 35/32 - Chicago IL

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

    My man and I want a well endowed male to meet us for some fun. We are looking for a good long fat cock not over 45.

  • Enjoy long time - w4m - 32 - Chicago IL

    Enjoy long time - w4m - 32 - Chicago IL

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

    Hey, I am 32 years old but very sexy and hot. I like oral pressure & love to suck. I can host. Contact me with a pic. Thanks

  • 31 y/r old woman looking 4 s_ex minded men.! - w4m - 31 - Chicago IL

    31 y/r old woman looking 4 s_ex minded men.! - w4m - 31 - Chicago IL

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

    31 year old lady seeks a man for friendship and s_ex minded men. Your age is not important to me.

  • I Am Always Available And Ready To Have Fun - w4m - 33 - Chicago IL

    I Am Always Available And Ready To Have Fun - w4m - 33 - Chicago IL

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

    I’ve got the kinks to make sure you’re satisfied sexually and i’ll make sure you feel real pleasure and the limitless enthusiasm you’ve always wanted, with my tricks, you’ll spit your cum several times, you can’t wait to fuck this real pussy,,, Catch...

  • Looking for Female Sub - m4w - Chicago IL

    Looking for Female Sub - m4w - Chicago IL

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

    Looking for sub female to call mine. Someone who loves to please and wants some attention. A nice sub who knows how to take orders and will do anything to please her Master. Serious inquires only!

  • Wanna suck a stranger - w4m - 27 - Chicago IL

    Wanna suck a stranger - w4m - 27 - Chicago IL

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

    I'm not single and need to be discreet. I've had a fantasy for a while now to suck off a complete stranger and take his load in my mouth. I don't want to have sex with you so don't ask please. Just suck you, take it in my mouth and maybe swallow plea...