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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June 4th, 2025

Submissive Male Seeks Dominatrix for Kinky Fun I'm Tobin from Chicago, Illinois, and I am a submissive male looking for a Dominant Female Mistress or Dominatrix to take control of me. I crave being forced into submission and taught how to properly please a Mistress. Some of my favorite submissive kinks include roleplay, spankings, and age p...

MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Chicago Dominatrix Message Me Online: MistressKim4subChicago Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......

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...

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...

Kinky Mistress Seeking Submissives for BDSM Fun! I'm Tessi from Chicago, and I have some wild kinks that I love exploring. If you're into BDSM, domination, submission, roleplay, spankings, or even age play, then we might just be a perfect match! I enjoy pushing boundaries and exploring new fetishes, so don't be shy to share your fantasies with m...

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...

Mistress Savannah in Chicago // Domme seeking new sub Strict Mistress for sub in Chicago I am a strict Mistress, currently accepting applications for subs. My time is precious to Me and I won't waste it on people who are not serious about this. I am tall, slender and have long silky hair. My calm demeanor doesn't give away My desire to strongly punish...

Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Chicago Hi! I'm Brandi, new TS in the Chicago area. I'm MtF preop transexual woman. I pass as female very well so we can go to your business function or out for dinner followed by a night of forbidden fun that only we will know about! I am fully functional, 8" thick hiding in my pant...

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. �...

Explore the Sensual World of Davin Hey there, Chicago! My name is Davin and I have a unique fetish that sets me apart from the crowd. Allow me to introduce myself and share what makes me tick. I'm a friendly guy who loves to embrace his submissive side. There's something exhilarating about surrendering control and letting a domina...

Passionate Swingers Looking for Playmates Hello there, I'm Brooke from Chicago, Illinois. My husband and I are fun-loving, open-minded, and kink friendly. We love exploring the world of swinging and meeting new like-minded individuals who share our passion for the lifestyle. You can find us in the FreeSexAds.com Swingers Lifestyle Profile...

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 ...

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 ...

F/M seeking love and fun Female to Male Trans Man in Chicago My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let it gro...

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...

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 ...

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 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...

Exploring Love and Connection as a Transgender Beauty Hey there, I'm Vicky from Chicago, Illinois. I may not fit into society's typical mold, but that's what makes me unique and beautiful. I embrace my transgender identity and love being part of the LGBTQ community. I enjoy spending time at local coffee shops like Intelligentsia or exploring the ar...

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...

Seeking Playful Partners in Chicago Hey there, I'm Josepha from the windy city of Chicago! My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We believe in creating a safe and exciting space for like-minded individuals to come together and have some fun. You can find us on sw...

Hot Shemale Myrna in Chicago Ready to Play Hey there, I'm a sexy shemale named Myrna looking for a local man in Chicago who can handle all my naughty desires. I love being both a top and bottom, giving and receiving blowjobs, getting my tight ass pounded, and riding a throbbing cock until we both explode with pleasure. I'm into all kinds of ...

Unleash Your Wildest Fantasies with Myrle from Chicago Hey there, I'm Myrle, a female swinger from the Windy City. 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. You can find us i...

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...

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...

Unleash Your Wildest Desires with Bernie from Chicago! Hey there, naughty neighbors of the Windy City! My name is Bernie, and I'm here to tell you about an adventure you won't want to miss. Together with my husband, let's dive into a world of pleasure and explore all the kinks and fetishes that make us feel alive.🔥 Now, let me paint a picture for ...

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 ...

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...

Passionate Chicago Swingers Seeking Playmates Hello there, I'm Felicity, a sultry vixen from the Windy City looking to add some spice to my already steamy life. My husband and I are fun-loving, open-minded, and kink friendly. We love exploring our deepest desires and pushing boundaries in the world of swinging. You can find us on FreeSexAds...

Kinky Fetish Fun with Brigid in Chicago! Hey there! My name is Brigid and I'm a kinky girl from Chicago who loves exploring all sorts of fetishes. You can find me on FreeSexAds.com Alt profiles under username brigidchic63963. I have a passion for BDSM, domination, and submission. I love being a Mistress and taking control, but I also enjo...

Explore Your Wildest Desires with Christa from Chicago Hey there! I'm Christa, a friendly and open-minded woman from Chicago who loves to explore all kinds of kinks and fetishes. One of my favorite fetishes is wearing latex clothing. There's something so empowering about slipping into tight, shiny latex that makes me feel confident and sexy. I love th...

Rosanne the Raunchy Shemale Ready to Play in Chicago I love nothing more than getting down and dirty with a man who knows how to handle a hot shemale like me. My name is Rosanne, and I'm on the hunt for a local guy who can satisfy all my cravings. From deepthroating blowjobs to rough anal play, I'm up for anything that will leave us both moaning in ...

Exploring Kinky Fetishes with Molli I'm Molli, a kinky fetish enthusiast from Chicago, Illinois. I love diving into the world of BDSM, domination, and submission. Whippings, roleplay, and spankings are just a few of my favorite kinks to explore. But I'm always looking to push boundaries and try new things. If you're into age play o...

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...

Transgender Beauty Looking for Love Hey there! My name is Mandi and I'm a transgender woman living in Chicago, Illinois. I have a curvy body and I love embracing my Latina heritage. You can check out my pics at my personal profile page @mandic21518. I'm proud to be part of the LGBTQ community and I enjoy being able to express my tr...

Join Nicolle for an Unforgettable Swinging Experience in Chicago! Hey there, I'm Nicolle 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 a seasoned swinger or just curious about the lifestyle, we welcome you to join us for some steamy fun! You can find us on swing...

Submissive Male Seeks Dominatrix for Kinky Fun I'm Romain, 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 romainch21685. I enjoy a variety of submissive kinks ...

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...

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...

Submissive Male Seeks Dominatrix for Kinky Fetishes and BDSM Fun I'm Lockwood from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control of me. I crave being forced into submission and taught how to properly please a Mistress. Some of the submissive kinks I enjoy include roleplay 🎭, spankings 👋...

Kinky Mistress Issy from Chicago Seeks Submissives for BDSM Fun I'm Issy, a dominant woman from Chicago looking for submissives who are ready to explore their wildest fantasies with me. I love all things kinky and taboo, from whippings to roleplay to age play. Nothing is off-limits when you're with me. If you're into domination and submission, then I'm the Mi...

Explore Your Wildest Desires with Gennifer from Chicago Hey there! I'm Gennifer, and I have a unique fetish that I absolutely love. It's not something you hear about every day, but it really gets me going. I'm friendly, open-minded, and always up for exploring new kinks and fetishes. One thing that really intrigues me is Femdom - the idea of taking co...

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...

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...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Kraig from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control and show me the ways of proper submission. I can be found on FreeSexAds.com Alt profiles under username kraigchic26575. I enjoy being tied up and spanked 🍑, roleplay...

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...

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...

HMU for Sex in Chicago Newly Single and Ready to Mingle in Chicago Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Chicago, Illinois area then message me @BarbieSingle28.      ...

Discover the Enchanting World of Paulie from Chicago! Hey there! It's Paulie, your friendly fetish explorer from the Windy City. I'm here to share a little secret with you - I have a unique and exciting fetish that sets my heart racing and ignites my imagination. Now, let me tell you what I love about it. This fetish of mine takes me on thrilling a...

Hot Shemale in Chicago Looking for Some Naughty Fun Are you ready to have the time of your life with a sexy shemale like me, Bernadette? I'm on the hunt for a local man who can handle all the kinky and wild things I have in store. When it comes to sex, I'm not shy about what I like. From deepthroating your cock to riding you hard and fast, I want ...