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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  • January 22nd, 2026
  • Unleash Your Desires with Vikki from Chicago!Unleash Your Desires with Vikki from Chicago! Hey there, fellow thrill-seekers! I'm Vikki, a fiery female swinger hailing from the vibrant city of Chicago, Illinois. Together with my loving husband, we're here to take you on an unforgettable journey into the realm of pleasure and exploration. What sets us apart? Well, let me tell you. We are...
  • Explore Your Desires with Ray from Chicago!Explore Your Desires with Ray from Chicago! Hey there! My name is Ray, and I'm here to tell you about a unique fetish that I absolutely love. It's called "Tickle Torture"! 🤭 There's something exhilarating about being tickled relentlessly, feeling those uncontrollable giggles burst out of me. It's like a rollercoaster ride for my senses!...
  • 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...
  • Submissive Male Seeks Dominatrix for Kinky BDSM FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Mendel from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control and force me into submission. I can be found on FreeSexAds.com Alt profiles under username mendelchi94261. I enjoy being dominated in various ways, such as whippings, ...
  • Explore Your Wildest Desires with CamilleExplore Your Wildest Desires with Camille Hey there! I'm Camille from Chicago, and I have a unique fetish that I absolutely adore. It's all about feet - the feeling of soft skin under my fingertips and the power it gives me to make someone weak at the knees. I love how it can be both sensual and dominant at the same time. I'm a friendly ...
  • Looking for Love and AdventureLooking for Love and Adventure Hey there! My name is Nathalie and I'm a transgender woman living in the beautiful city of Chicago, Illinois. 💃🌆 I wanted to take a moment to tell you a bit about myself and what I'm looking for. First things first, let's talk about what I enjoy about being part of the LGBTQ community. The ...
  • 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 FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Fowler from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress to take control. I crave being forced into submission and taught how to properly please a Mistress. Whippings, domination, roleplay, and humiliation are some of the kinks I enjoy, but I'm also eage...
  • January 21st, 2026
  • 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...
  • Kinky Fetish Seeker Ready to Explore New AdventuresKinky Fetish Seeker Ready to Explore New Adventures My name is Saudra and I am a Chicago-based fetish enthusiast looking for like-minded individuals to share my passions with. From BDSM to roleplay, I enjoy exploring a wide range of kinks and fetishes that push boundaries and ignite my senses. Whether it's whippings, domination, submission, or age...