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

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...

Domme looking for male sub who wants to be owned Domme for male sub in Chicago I am Mistress Danielle. FemDom is My lifestyle, not something I do merely for fun. I have an opening in My dungeon for a submissive male. Send your photo along with an explanation of your kinks and fetishes and how you believe you can serve Me.  This is a serious...

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...

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...

Explore Kinks and Fetishes with Luana from Chicago Hey there, I'm Luana 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 embracing our wildest desires. You can find us on swingers dating profiles under the member name lu...

Join me and my husband for some steamy fun! Hey there, I'm Wynny 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 ...

A Sensual Journey of Self-Discovery Hey there, I'm Karrie from Chicago, Illinois. I may not fit society's idea of "normal," but that's what makes me unique and special. Being transgender has allowed me to embrace my true self and connect with others in the LGBTQ community. I love exploring the vibrant nightlife in Boystown, grabbin...

DOMME AVAILABLE for private Femdom and DISCIPLINE Experienced Dominatrix for Chicago Submissive Experienced Dominatrix seeks submissive, ready and willing to learn discipline from a loving but strict Mistress. Contact me @ ChicagoDommeX if you are available and willing to serve my needs. Available For: Discipline  Corporal Punishment Ro...

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 Your Wildest Desires with Britte Hey there! I'm Britte from Chicago, and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom, where I can take control and dominate in the bedroom. It's such a thrilling experience for me! I'm a friendly and open-minded person who loves to try new things and explor...

Shemale Nightclubs Near You in Chicago, Illinois Shemale Nightclubs Near You in Chicago, Illinois Shemale Clubs Near You in Chicago, Illinois is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so. Please contact us if yo...

Kinky Dominatrix seeks puppy to train DOMINATRIX SEEKS PUPPY TO TRAIN  Are you the submissive little puppy I have been looking for? I am A Power Domme looking for the one to meet my needs. I am on this site, because I know too often you seek an escape... with someone you can relinquish your power to. I know there's a lot of pressu...

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...

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...

Explore Your Wildest Desires with Cathleen from Chicago Hey there! I'm Cathleen, and I have a unique fetish that I absolutely love. It's something that sets my heart racing and my mind spinning with excitement. I won't tell you what it is just yet, but trust me, it's something you won't forget. I'm a friendly and open-minded person who loves to explor...

INTERACTIVE MAP: Transexual Tracker in the Chicago Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Chicago area for friendship or sex hookups. View member thumbnails on the interactive map below to meet local members who want to meet local transexuals or admirers. Click any member photo below to get started. Sign up free for i...

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 ...

Kinky Chicago Fetish Seeker I'm Jany, a kinky girl from Chicago who loves exploring all kinds of fetishes and kinks. Whether you're into BDSM, domination, submission, roleplay, spankings, or anything else that gets your heart racing, I'm your girl. I love pushing boundaries and trying new things in the bedroom. One of my ...

Swinging Couple in Chicago, New to the Lifestyle Swinging Couple in Chicago We are a swinging couple in Chicago, Illinois. New to the lifestyle but eager to learn and explore the swingers world! About Him He is Jeff, a former military, larger, fit, age 29. He works out daily, loves trucks, camping, hunting, fishing and all the usual guy things....

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...

Mistress seeks Chicago male sub for BDSM and training Mistress seeking male sub in Chicago I am Mistress Velvet Sky. I use a variety of toys on My boys. You will be My submissive boy toy. I have a contract that We/we will mutually agree to in writing. We/we can hash this out if we decide to enter a Dom/sub relationship. I am not a game player, so plea...

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 ...

Join Alisa from Chicago for an unforgettable swinging experience Hi there! My name is Alisa 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 interests and are always up for a good time. You can find us in the sw...

Hot Shemale in Chicago Looking for a Wild Time! Are you ready to have some naughty fun with a sexy shemale named Joell? I'm looking for a local man who can handle all of my desires and fantasies. I love being both a top and bottom, giving blowjobs, getting my ass licked, sucking dick, and riding cock like there's no tomorrow. I want to make you...

'>Tempting and Thrilling: Explore the World of Bridgett's Unique Fetish!
Hey there, fellow kinksters of Chicago! My name is Bridgett, and I have a secret that I just can't keep to myself any longer. I've got a unique fetish that sets my heart racing and ignites my imagination like nothing else. And guess what? I want to share it with you! Now, before I dive into the d...

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...

Kinky Mistress Seeking Submissives for BDSM Play I'm Marcella, a dominant woman from Chicago who loves to explore all kinds of kinky fetishes. Whether you're into whippings, roleplay, or age play, I'm ready to take control and show you a good time. I enjoy pushing boundaries and testing limits, so don't be afraid to share your deepest desires w...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Chicago AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you! Private Message ...

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...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Chicago Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

A Sensual Journey with Maddy Hey there, I'm Maddy, a fun-loving transgender babe from Chicago. I may not fit society's standards of beauty, but my confidence and charm will sweep you off your feet. 🌈 I love exploring the diverse LGBTQ scene in the city, whether it's dancing the night away at Berlin Nightclub or enjoying a...

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...

Explore Your Deepest Desires with Sarajane Hey there, fellow kinksters of Chicago! My name is Sarajane, and I've got a unique fetish that will make your heart race and your mind wander. Brace yourself for an unforgettable journey into the world of Femdom! Now, let me tell you why I adore my fetish. It's like a thrilling dance of power and...

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...

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 ...

Explore Your Deepest Desires with Erhard - A Submissive Gentleman from Chicago! Hey there! My name is Erhard, and I'm an open-minded guy from the beautiful city of Chicago, Illinois. I wanted to share something unique about myself with you all today. You see, I have this fascinating fetish that brings me so much joy and excitement! I find immense pleasure in being submissive...

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...