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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  • September 12th, 2025
  • 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 Valentia for an Unforgettable Swinging ExperienceJoin Valentia for an Unforgettable Swinging Experience Hello there! My name is Valentia, and I am a female swinger from Chicago, Illinois. My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We enjoy meeting new people who share our adventurous spirit. You can find us in the swingers dating prof...
  • Passion-Seeking Swingers in Chicago!Passion-Seeking Swingers in Chicago! Hello there, I'm Arlena from Chicago, and my husband and I are on the hunt for some steamy adult fun. We're a couple who loves to play, explore, and indulge in all things naughty. Our open-mindedness knows no bounds, and we're always up for trying new things in the swinging lifestyle. You can fin...
  • Submissive Male Seeks Dominatrix for Kinky BDSM FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Marshall, a submissive male from Chicago, Illinois. I'm 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 marshall38483. I enjoy kinky fetishes like whi...
  • 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...
  • September 11th, 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!...
  • 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...
  • 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...
  • 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...
  • 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 ...