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!

Home / Alternative Sex Ads /

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

December 25th, 2025

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...

Kinky Mistress Teresa Looking for Submissives on FreeSexAds.com I'm Teresa, a kinky mistress from Chicago who loves exploring all sorts of fetishes and kinks. I enjoy BDSM, domination, submission, roleplay, and so much more. Whippings, spankings, and humiliation are just a few of the things that get me excited. I'm always looking to push boundaries and try n...

Sparkling Transgender Beauty Looking for Love Hey there! I'm Lindie, a transgender woman from Chicago who loves exploring the city's diverse neighborhoods and trying out new restaurants. I may not fit into society's traditional gender norms, but that's what makes me unique and proud to be part of the LGBTQ community. I enjoy long walks by L...

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 ...

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 ...

Catherine's Kinky Fetish Adventures in Chicago I'm Catherine, and I'm a kinky girl from Chicago looking for some naughty fun! I have a few fetishes that really get me going, like BDSM, domination, and roleplay. I love being in control and taking charge of my submissives. Whippings, spankings, and humiliation are just a few of the things I enjo...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Amos, a submissive male from Chicago, Illinois, looking for a Dominant Female Mistress or Dominatrix to force me into submission. I crave being dominated and controlled, learning how to please a Mistress properly. You can find me on FreeSexAds.com Alt profiles under username amoschi57990. I e...

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...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Chicago Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&nb...

Kinky Fetish Fun in Chicago! I'm Jeanette, a kinky girl from Chicago looking for some naughty fun! I love exploring all kinds of fetishes and kinks, from BDSM to roleplay to age play. I'm always up for trying new things and pushing boundaries. If you're into whippings, domination, or submission, then I'm the Mistress for yo...

Unleash Your Desires with Aurora from Chicago Looking for an unforgettable adventure that will leave you breathless? Look no further! I'm Aurora, a passionate and open-minded female swinger hailing from the vibrant city of Chicago, Illinois. Together with my husband, we are on a quest to explore the depths of pleasure and indulge in alluring ...

Explore Your Desires with Joaquin Hey there! My name is Joaquin, and I'm a friendly guy from Chicago, Illinois. I wanted to share something unique about myself – I have a fascinating fetish that truly excites me. It's all about the world of tickling! 🤭 There's something incredibly thrilling about being tickled, feeling those...

Kinky Fetish Fun in Chicago! I'm Meredith, 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. Whippings, spankings, and age play are just a few of the things that get me excited. I'm always open to trying new things and...

Kinky Fetish Fun in Chicago! Are you looking for a wild time with a kinky fetish lover? Well, look no further because I'm Andee, and I'm ready to explore all your wildest fantasies right here in Chicago, Illinois! Whether you're into BDSM, domination, or roleplay, I'm your girl. I love whippings and spankings, and I can be...

Submissive Male Seeks Dominatrix for Kinky Fetish Fun I've always been a submissive male at heart, craving the touch of a strong Dominant Female Mistress to guide me into submission. My name is Lorrie and I'm from Chicago, Illinois. I'm on the hunt for a powerful woman who can force me to my knees and show me how to properly please a Mistress. Some...

Young ebony submissive waiting to please the right 'Sir' Submissive Ebony Woman for Sir Call or text me! Contact me for my recent pics and contact info. No drama, no games, these are my own 100% real pics MY GALLERY - @desireeXXsub...

Kinky Chicago Girl Looking for BDSM Adventures My name is Libbey and I'm a kinky girl from Chicago, Illinois who loves exploring all kinds of fetishes. I enjoy being a Dominatrix and taking control in the bedroom, but I also love to switch things up and be a submissive little pet for the right person. Whippings, spankings, and roleplay are som...

Naughty Shemale Looking for a Wild Time in Chicago Hey boys, I'm Jerry and I'm a sexy shemale looking for a local man who can handle all my dirty desires. When it comes to fun in the bedroom, I'm not shy about what I like. I love giving sloppy blowjobs, getting my tight ass pounded hard, and riding a huge throbbing cock until we both explode with or...

'>Step into Marcelle's World of Sensual Delights
Hey there! I'm Marcelle from Chicago, and I have a unique fetish that sets my heart racing. I absolutely love indulging in foot worship. There's something so sensual and intimate about having my feet pampered and adored. The feeling of soft kisses and gentle caresses on my toes sends shivers down ...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I never knew how much I craved being a submissive male until I discovered the world of Elroy. My name is Elroy and I am from Chicago, Illinois. I am seeking a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to please a Mistress properly. You can find me in the Fre...

Kinky 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...

Kinky Fetish Fun in Chicago! I'm Ema, a kinky fetish lover from the Windy City looking for some naughty adventures. I have a passion for BDSM, domination, and roleplay. Whippings, spankings, and humiliation really get me going 😈 I'm always eager to explore new kinks and fetishes with open-minded individuals who share my ...

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'...

December 24th, 2025

Unleash your Desires with Jolynn - Explore the World of Femdom! Hey there, fellow kinksters of Chicago! It's Jolynn here, ready to dive into the wild world of fetishes and fantasies. If you're looking for something unique and exciting, then look no further than yours truly. Now, let me introduce you to my secret passion - I have a thing for tickling! Yes, you...

Explore Your Wildest Desires with Roselyn from Chicago Hey there, I'm Roselyn from Chicago, and I have a unique fetish that I absolutely love! I adore dressing up in latex outfits and dominating my partner. The feeling of power and control gets me so excited! I'm a friendly and open-minded person who loves to explore different kinks and fetishes. I'...

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...

Hot Shemale in Chicago Ready to Play and Fuck Hey boys, I'm a sexy shemale named Odelia looking for a local man in Chicago who can handle all of me. I love getting down and dirty, so if you're into wild sex and fun times, I'm your girl... well, shemale.I'm a versatile babe who loves to top and bottom. I enjoy giving blowjobs, getting my ass pou...

Sexy Transgender in Chicago Looking for Love Hey there! I'm Kathie, a fun-loving transgender woman living in the Windy City. I may not fit society's norms, but that's what makes me unique and fabulous. I embrace my LGBTQ identity and love being part of such a diverse community. I enjoy cozy coffee dates at local cafes like Intelligentsia or...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Robb, a submissive male from Chicago looking for a Dominant Female Mistress or Dominatrix to take control and show me the ways of submission. I crave being forced into my place, learning how to properly please a Mistress, and exploring all sorts of kinky fetishes and roleplay scenarios. I en...

Hot Shemale Vivian Looking for Naughty Fun in Chicago Are you ready for a wild time with a sexy shemale in the Windy City? I'm Vivian, and I'm on the hunt for a local man who can handle all of my filthy desires. I love to get down and dirty, exploring every inch of your body with my throbbing cock and tight ass. I'm a top who loves to take control, ...

Explore Your Wildest Desires with Tessi from Chicago Hey there! I'm Tessi, a fun-loving gal from the Windy City with a unique fetish that will blow your mind. I absolutely adore dressing up in latex and dominating my partner as a fierce Femdom queen. The power and control excite me like nothing else! I'm friendly, open-minded, and always eager to e...

Chicago Femdom Mistress Stormy Seeks Submissive Men for Kinky Fun Are you ready to submit to a powerful and dominant woman? Look no further, I am Mistress Stormy from Chicago, Illinois, and I am here to fulfill all your deepest fantasies. As a seasoned Dominatrix, I thrive on exploring kinks and fetishes with willing submissives. Whether you crave being humiliat...

Tempting Adventures Await with Jacquelin from Chicago Hello there! My name is Jacquelin, 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 believe in living life to the fullest and enjoying new experiences. You can find us on swingers datin...

Explore Kinks and Fetishes with Adrian from Chicago Hey there! I'm Adrian, a female swinger from Chicago, Illinois. My husband and I are friendly, open-minded, and always up for exploring new kinks and fetishes. We love meeting like-minded individuals who share our passion for excitement and adventure in the swinging lifestyle. You can find us in t...

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...

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...

Passionate Swingers Looking for Playmates in Chicago Hey there, I'm Marthe, and my husband and I are on the hunt for some sexy new friends to join us in our wild adventures. We're fun-loving, open-minded, and kink friendly - always up for trying new things and exploring our deepest desires. You can find us on FreeSexAds.com Swingers Lifestyle Prof...

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...

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...

Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Chicago Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very feminine...

Passionate Swingers Seeking Playmates in Chicago Hello there, I'm Doria from the windy city of Chicago. My husband and I are a fun-loving couple who are open-minded and kink friendly. We love exploring our wildest fantasies and meeting like-minded individuals who share our passion for the swinging lifestyle. You can find us on FreeSexAds.com S...

Elegant Transgender Beauty Seeking Connection in Chicago Hey there! I'm Genna, a transgender woman from the Windy City. I may not fit society's narrow definition of beauty, but my unique body type and heritage make me who I am - and that's something special. 💃🏽 I love exploring LGBTQ-friendly spots in Chicago like Roscoe's Tavern or Sidetrack. Le...

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...

Exploring Kinky Desires with Haley in Chicago I've always had a wild side when it comes to exploring fetishes and kinks. My name is Haley, and I'm from Chicago, Illinois. I love diving into the world of BDSM, domination, submission, roleplay, and more. There's nothing that gets me more excited than pushing boundaries and trying new things. O...

Spark Up Your Love Life with Marta! Hey there! I'm Marta, a fun-loving transgender gal from Chicago, Illinois. I may not fit society's mold, but that's what makes me unique and fabulous! 🌈 I enjoy being part of the LGBTQ community because it allows me to express myself freely and authentically. It's all about love and acceptance...

Korie's Kinky Fetish Adventures I've always had a wild side when it comes to exploring fetishes and kinks. From BDSM to domination, I love pushing boundaries and trying new things. My name is Korie, and I'm a fetish enthusiast based in Chicago, Illinois. One of my favorite kinks is roleplay. I enjoy dressing up and getting into...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun
I'm Mac, 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 mac52427. I have always had a craving for whippings, dom...

Kinky Domina Romona Seeks Obedient Submissive for BDSM Fun Hello there, my name is Romona and I am a strict Dominatrix based in Chicago, Illinois. Are you ready to explore your deepest desires and kinks with me? Look no further, as I am here to guide you through a world of domination and submission like never before. I have a passion for whippings, role...

Kelci's Kinky World Hey there! I'm Kelci from Chicago, and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom, where I get to take control and dominate my submissive partner. It's such a thrill for me to be in charge and see them surrender to my every command. I'm a friendly and op...

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 ...