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 4th, 2025

Kinky Fetish Fun in Chicago My name is Lorilyn and I'm a kinky girl from Chicago looking for some naughty fun. I love exploring all kinds of fetishes and kinks, from BDSM to roleplay to domination and submission. There's nothing I enjoy more than taking control and giving out some well-deserved spankings. 🍑 I have a wild...

Elegantly Transcending Boundaries Hey there! I'm Jennine, a transgender woman from Chicago, Illinois. I love exploring the diverse neighborhoods of the city like Wicker Park, Lakeview, and Pilsen. If you're looking for someone who enjoys being their authentic self and embraces the LGBTQ community, then look no further! I find bea...

Exploring Kinky Fetishes with Paulette from Chicago I love to indulge in all sorts of fetishes and kinks, and I'm always looking for new experiences to explore. My name is Paulette, and I hail from the windy city of Chicago, Illinois. Whether you're into BDSM, domination, submission, roleplay, spankings, or any other naughty activities, I'm your gi...

Calling 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!...

Explore Your Wildest Desires with Katherine! Hey there, I'm Katherine from Chicago, and I have a unique fetish that I absolutely love! I am really into foot worship and find it incredibly sensual and exciting. There's just something about having my feet pampered and adored that drives me wild! I'm a friendly and open-minded person who love...

Discover Lynnelle: A World of Fetishes and Exploration Hey there! My name is Lynnelle, and I'm from the vibrant city of Chicago, Illinois. I wanted to take a moment to share something unique about myself - I have this intriguing fetish that adds a little spice to my life. Now, before you get all curious, let me tell you that it's called "Sensation Pla...

Male sub looking for Mistress in Chicago Male sub seeking Mistress in Chicago I am new in town. My name is Jon-boy. I had to leave my old Dominatrix behind and while I miss Her guidance and affection, I would love to find a new Mistress I can serve. If you are looking for a new sub or another sub to add to your list I would love to be con...

Looking for Love and Adventure! Hey there! My name is Karie, and I'm a transgender woman living in the beautiful city of Chicago, Illinois. 🌆 So, let me tell you a bit about myself. I have a unique body type that will make you feel like you're hugging a fluffy cloud ☁️. I come from a diverse ethnic background, which adds...

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...

Kinky Dominatrix Seeking Submissives for BDSM Fun I'm Valentia from Chicago, Illinois, and I have a passion for exploring all things kinky and taboo. If you're looking to delve into the world of domination and submission, then look no further because I'm your Mistress. From whippings to roleplay, I love pushing boundaries and testing limits. Whe...

Explore Kinks and Fetishes with Sondra in Chicago Hey there, I'm Sondra from Chicago! My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. Whether you're new to the scene or a seasoned pro, we're always up for trying something new and exciting. You can find us in the swingers dating profiles...

Passionate Swingers Seeking Playmates in Chicago Hello there, I'm Priscella from the windy city of Chicago. My husband and I are a dynamic duo ready to spice things up with some like-minded individuals who share our love for the swingers lifestyle. We're fun-loving, open-minded, and always up for a good time. You can find us on FreeSexAds.com ...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun My name is Herbert and I'm 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 in the FreeSexAds.com Alt profiles under username herbertchic49301. I have always had...

Hot Shemale Juliann Seeking Local Man for Wild Fun Looking for a man who can handle a tranny like me? Look no further! I'm Juliann, a sexy shemale from Chicago, Illinois, ready to show you a good time. I love getting down and dirty with a guy who knows how to please me in all the right ways. Whether you're into sucking my throbbing cock or lettin...

Debonair Trans dude, looks like Bond F2M Trans Dude in Chicago Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relationship.&n...

New Body New Me M2F post-op in Chicago Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Natasha...

Kinky Fetish Fun in Chicago Hey there, it's Lilia from the windy city of Chicago! I'm a kinky girl who loves to explore all sorts of fetishes and kinks. You can find me on FreeSexAds.com Alt profiles under username liliach99616. I have a thing for BDSM and domination. There's nothing more thrilling than taking control and mak...

Submissive Male Seeks Dominatrix for Kinky Fun Hey, I'm Roscoe from Chicago, Illinois. I'm a submissive male looking for a Dominant Female Mistress to take control and show me the ways of proper submission. You can find me on FreeSexAds.com Alt profiles under username roscoechic42046. I enjoy kinks like whippings, roleplay, and age play, but I'...

Sexy Transgender in Chicago Looking for Love Hey there, I'm Jessy, a sassy transgender babe living in the Windy City. I love exploring all the amazing LGBTQ-friendly spots in Chicago, like Boystown and Andersonville. I'm always down for a cozy coffee date at Intelligentsia or a fun night out dancing at Berlin. Being trans has allowed me to ...

Sultry Transgender Beauty Looking for Love in Chicago Hey there! I'm Lora, a confident and sassy transgender woman living in the Windy City. I may not fit society's standards of beauty, but I rock my curves with pride. Being transgender has opened my eyes to a whole new world of self-discovery and acceptance, and I wouldn't have it any other way. I...

Kinky Mistress Seeking Submissives for BDSM Fun Hey there, I'm Vickie from Chicago, and I have some naughty desires that need fulfilling. I love exploring all things kinky and taboo, from whippings to roleplay to age play. There's nothing too wild or out there for me! 🖤 I'm looking for open-minded individuals who are willing to submit to my...

Mistress has opening for a male submissive training in Chicago area Mistress Seeks submissive male in Chicago Mistress seeks submissive male for training in Chicago. Are you a sub and available evenings or weekends? Some weekdays are available upon request. Our first few meetings will decide if we can work together and we will come to a written agreement after disc...

Join Joell for a Sensual Adventure in Chicago! Hey there, I'm Joell from Chicago, Illinois. My husband and I are friendly, open-minded, and we love to explore kinks and fetishes. We're always up for trying new things and meeting like-minded individuals who share our passion for excitement and pleasure. You can find us in the swingers dating pr...

Explore Your Wildest Desires with Kelsy from Chicago Hey there! I'm Kelsy, and I have a unique fetish that I absolutely love exploring. I won't give too much away, but let's just say it involves some playful domination and submission 😉. I'm always up for trying new things and pushing boundaries, so if you're open-minded like me, we'll definitely ...

Sexy 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. �...

Femdom 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...

Passionate Swingers Looking for Playmates in Chicago Hello there, I'm Marylou from Chicago, Illinois. My husband and I are a fun-loving, open-minded couple who love exploring our kinks and fantasies with like-minded individuals. We believe that life is too short to not indulge in the pleasures of the flesh, and we are always looking for new adventur...

Explore Kinks and Fetishes with Hally from Chicago! Hey there! I'm Hally, 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. Whether you're new to the scene or a seasoned pro, we're always up for trying something new and exciting. You can find us in th...

Submissive Male Seeks Dominatrix for Kinky Fun Hey there, my name is Murray and I'm a submissive male from Chicago, Illinois looking for a Dominant Female Mistress or Dominatrix to show me the ropes. I crave being forced into submission and taught how to properly please a Mistress. I enjoy exploring various kinks such as BDSM, roleplay, spanki...

Mistress Leila, Mature Mistress for sub in Chicago Mistress Leila Chicago Female Domination Mistress Leila is a strict and sensual FemDom with a decided taste for the extreme! I am accepting submissive male and female applicants. I enjoy foot worship, slave training, strap-ons and total control. See all the possibilities and lots more pics on my pe...

Spark Up Some Chemistry with Cassandra! Hey there, I'm Cassandra from Chicago, Illinois. I'm a curvy, Latina transgender woman who loves exploring the city and trying out new restaurants. I'm proud to be part of the LGBTQ community and enjoy connecting with others who share similar experiences. I'm looking for someone who is open-minde...

Join Bianca for an Unforgettable Swinging Experience in Chicago! Hey there, I'm Bianca 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're always up for trying new things and meeting like-minded individuals who share our passion for excitement and adventure. You can find us in...

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...

Passion Seekers in Chicago Are you ready to spice up your sex life and explore your wildest fantasies? Look no further, because my husband and I are the fun-loving, open-minded swingers you've been searching for. My name is Jo Ann, and I hail from the vibrant city of Chicago, Illinois. We are a couple who thrives on adven...

Transgender Beauty Looking for Love in Chicago Hey there! I'm Carolina, a proud transgender woman from the Windy City. I may not fit society's traditional mold, but that's what makes me unique and beautiful. I love being part of the LGBTQ community because it's full of love, acceptance, and diversity. I'm looking for someone who can apprecia...

Explore Your Desires with Evan from Chicago Hey there, I'm Evan from Chicago, and I have a unique fetish that I love to indulge in. I am really into foot worship 🦶and find it incredibly satisfying to submit to a Dominant woman who enjoys having her feet pampered and adored. I love the feeling of being controlled and dominated in this way...

Sweet and Sensual Transgender Beauty Looking for Love Hey there, I'm Beverlee from Chicago, Illinois. I may not fit society's typical mold, but that's what makes me unique and special. I love being part of the LGBTQ community because it allows me to express myself authentically and embrace who I truly am. I enjoy long walks by Lake Michigan, explor...

Tantalizing Evy from Chicago Seeks Submissive Male for Femdom Fun Hey there, I'm Evy and I have a unique fetish that I absolutely adore. It's something that brings me so much excitement and pleasure. I'm always open to exploring new kinks and fetishes with others who share my interests. I'm friendly, open-minded, and always up for a good time. One of the things...

Femdom Mistress Shane - Explore Your Kinks with Me Are you ready to submit to a powerful and kinky Domina in Chicago, Illinois? I am Mistress Shane, a strict and sensual Femdom who loves to take control. Whether you crave being dominated, humiliated, or simply exploring your deepest desires, I am here to guide you on your journey of submission. A...

Hot Shemale in Chicago Looking for Wild Fun Are you ready to experience the ultimate pleasure with a sexy shemale? Lucky here, and I'm on the hunt for a local man who can handle all of my dirty desires. I love getting down and dirty, so if you're into some raunchy fun, then I'm your girl. I'm a top shemale who loves to dominate in the bedr...

Join Harli for a Sensual Adventure in Chicago Hey there, I'm Harli from Chicago! My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We're always up for trying new things and meeting like-minded individuals who share our passion for excitement in the bedroom. You can find us on swingers ...

Unleash 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...

Welcome to our World of Sensual Exploration! Hey there! I'm Conny, a friendly and adventurous woman from the beautiful city of Chicago, Illinois. Together with my amazing husband, let's embark on a thrilling journey filled with passion and excitement. His name is Mark, by the way! Let me tell you a bit about myself. I have mesmerizing hazel...

Discover the Magic of Love with Rhianon!
Hey there, lovely people of Chicago! My name is Rhianon and I'm thrilled to be part of this amazing LGBTQ community. 💖 Being transgender has allowed me to embrace my true self and experience life from a unique perspective. It's been quite a journey, but I wouldn't change it for the world! I'm ...

Explore Your Desires with Luci Hey there, Chicago! It's your girl Luci, and I've got something special to share with you. Are you ready to dive into a world of excitement and pleasure? Well, look no further because I'm here to make all your fantasies come true. Let me introduce myself - I'm a friendly and open-minded gal who l...

Looking 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 ...

Kinky Fetish Fun in Chicago! I'm Tammie, a naughty girl from Chicago looking for some kinky fun. I love exploring all sorts of fetishes and kinks, from BDSM to roleplay to age play. I enjoy being a Dominatrix and taking control, but I also love being submissive and letting someone else take the lead. Spankings, whippings, and...

Looking for Love and Adventure in the Windy City! 🌈 Hey there, lovely people of Chicago! My name is Muriel, and I'm a proud transgender individual ready to embrace life's incredible journey. 💖 Living in this vibrant city has allowed me to fully express my authentic self, and I couldn't be happier. Being part of the LGBTQ community has taught me...

FtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago Hi, I'm Andy, age 33, FtM transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message @AndyFtM4P...

Raunchy Shemale Seeking Local Man for Wild Fun I'm a naughty shemale looking for a hot man in Chicago who can handle all my dirty desires. My name is Stormie and I want to show you a good time. I love getting down and dirty, so if you're into that, hit me up! I enjoy being both a top and bottom, giving blowjobs, getting my tight ass fucked ha...