Chicago, Illinois Alternative Sex Ads - BDSM, Trans & Swingers

Browse Chicago, Illinois alternative sex ads to meet kinky locals looking for BDSM, domination & fetish, transgender sex, or swingers & threesomes hookups near you. It's free to search these alternative classifieds, or post your own ad!

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  • July 17th, 2025
  • Calling all adventurous souls! Explore the world of Maisie from ChicagoCalling all adventurous souls! Explore the world of Maisie from Chicago Hey there, curious minds of Chicago! My name is Maisie, and I'm here to invite you on a tantalizing journey into the realm of fetishes. Now, before we dive in, let me assure you that I'm friendly, open-minded, and always up for exploring new kinks and fetishes. So, buckle up and let's get started!...
  • Kinky Fetish Fun with Elicia from ChicagoKinky Fetish Fun with Elicia from Chicago I'm Elicia, a kinky fetish lover from the Windy City! I have a passion for exploring all kinds of naughty desires and indulging in taboo pleasures. Whether you're into BDSM, domination, submission, roleplay, or anything else that gets your heart racing, I'm your girl! I love to indulge in whippi...
  • Unleash Your Desires with RomeoUnleash Your Desires with Romeo Hey there, Chicago! It's your friendly neighborhood Romeo here, ready to share my unique fetish and explore the world of kinks and desires. Allow me to introduce myself - I'm a laid-back guy from the Windy City, Illinois, seeking an adventure with a Dominant woman who can embrace my submissive sid...
  • Femdom Mistress EddiFemdom Mistress Eddi's Kinky Domination Playground Are you ready to submit to a powerful and seductive Dominatrix in the Windy City? Look no further, for I am Mistress Eddi, your ultimate Femdom fantasy come to life. I thrive on exploring a wide range of kinks and fetishes, from strap-ons and pegging to whippings and spankings. I enjoy pushing b...
  • CecillaCecilla's Kinky Fetish Adventures I'm Cecilla from Chicago, and I have some wild fetishes that I love exploring. You can find me on FreeSexAds.com Alt profiles under username cecillach44361. I'm into all things BDSM, from whippings to domination and submission. One of my favorite kinks is roleplay 🎭. I love getting into chara...
  • Join Saundra in Chicago for Some Swinging Fun!<br>Join Saundra in Chicago for Some Swinging Fun!
    Hey there, I'm Saundra from the Windy City! My husband and I are a friendly and open-minded couple who love to explore all sorts of kinks and fetishes. We're always up for trying new things and meeting like-minded individuals who share our passion for adventure in the bedroom. You can find us on s...
  • Passionate Swingers Seeking Playmates in ChicagoPassionate Swingers Seeking Playmates in Chicago Hello there, I'm Leeanne, a sultry swinger from the windy city of Chicago. My husband and I are a dynamic duo who love to explore the depths of our desires and fantasies with like-minded individuals. We are fun-loving, open-minded, and kink-friendly, always up for a good time in the swinging lifes...
  • July 16th, 2025
  • Kinky Fetish Fun with Rosalia in ChicagoKinky Fetish Fun with Rosalia in Chicago I love exploring all kinds of kinks and fetishes, from mild to wild! My name is Rosalia, and I'm a naughty girl from Chicago who can't get enough of the BDSM scene. Whether you're into domination or submission, I'm your girl. I enjoy roleplay, spankings, and even some light whippings. But that's...
  • Sexy Transgender Beauty Looking for Love in ChicagoSexy Transgender Beauty Looking for Love in Chicago Hey there! I'm Lorianna, a fun and flirty transgender girl living in the Windy City. I may not be your typical girl, but that's what makes me special! I love embracing my trans identity and being a part of the LGBTQ community. It's all about being true to myself and spreading love wherever I go. ð...
  • Submissive Male Seeks Dominatrix for Kinky BDSM Fun<br>Submissive Male Seeks Dominatrix for Kinky BDSM Fun
    I'm Edwin, a submissive male from Chicago, Illinois, looking for a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to please a Mistress properly. I can be found on FreeSexAds.com Alt profiles under username edwin56831. I enjoy being spanked and whipped, as well...