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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October 26th, 2025

Raunchy Shemale Seeking Local Man for Wild Fun Hey sexy studs, I'm Glory, a hot shemale from Chicago looking for a man who can handle all of me. I love it all - from deepthroat blowjobs to getting my tight ass pounded hard. If you're into kinky play and want to explore your wildest fantasies, then I'm the tranny for you. I enjoy being both a to...

Elegant Trans Beauty Seeks Connection Hey there! I'm Garnette, a transgender gal from Chicago who's looking to meet someone special. I may not fit society's standards of beauty, but I embrace my unique body type and ethnicity with pride. Being part of the LGBTQ community has allowed me to explore my true self and connect with others w...

Explore Your Wildest Desires with Harry from Chicago Hey there, I'm Harry from Chicago, and I have a unique fetish that I can't get enough of. I love being tickled! The feeling of helplessness and vulnerability is such a turn on for me. I'm a submissive guy who would love to meet a Dominant woman who enjoys exploring this kink with me. I'm friendly...

Passionate Swingers Seeking Playmates Hello there, I'm Charlotta from Chicago, Illinois. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We are active members of the swinging lifestyle community and can be found on FreeSexAds.com under the username charlot...

Kinky Fetish Fun with Athene in Chicago! Hey there, it's Athene from Chicago! I'm a kinky fetish lover looking to explore all sorts of naughty desires. You can find me on FreeSexAds.com Alt profiles under username athenech54762. I have a passion for BDSM and domination. Whippings, spankings, and roleplay really get me going 🔥 I love b...

Explore Your Desires with Debra from Chicago! Hey there! My name is Debra, and I'm here to tell you about a unique fetish that I absolutely adore. It's called trichophilia, and let me tell you, it really gets my heart racing! 🌟 Trichophilia is all about the sensual pleasure of hair. Whether it's long and silky or short and spiky, I find i...

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...

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...

Passion Seekers in Chicago - Swingers Looking for Playmates Hello there, I'm Debee from the windy city of Chicago, Illinois. My husband and I are fun-loving, open-minded, and kink friendly swingers who are always looking to spice things up in the bedroom. We love exploring new fantasies and indulging in our wildest desires. 💋🔥 If you're looking for ...

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...

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 ...

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......

Explore Your Wildest Desires with Nedi! Hey there, I'm Nedi from Chicago, Illinois! I have a unique fetish that I absolutely adore. It's all about exploring different kinks and fetishes, and I love every minute of it. I'm friendly, open-minded, and always up for trying new things. One thing that really intrigues me is Femdom. The idea ...

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...

Interviewing for new submissive for evenings and/or weekends Domme Woman for sub male in Chicago I need a new male subbie who can come 'do' stuff around My house in exchange for some ass beating and gentle torture. This is not a game, but it is fun. We/we will need something in writing so We/we understand each other's places and we will need to come to a mut...

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 ...

Well Endowed Shemale for Man in Chicago Hung Shemale for Man in Chicago I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncenso...

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...

Join Renelle for a Swinging Adventure in Chicago! Hey there, I'm Renelle, 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're always up for trying new things and meeting like-minded individuals who share our passion for excitement and pleasure. ...

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...

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...

Explore Your Wildest Desires with Coraline from Chicago Hey there! I'm Coraline, a friendly gal from Chicago who has a unique fetish for wearing latex clothing. There's something about the tight, shiny material against my skin that really gets me going. I love the way it makes me feel powerful and sexy. I'm super open-minded and always up for explorin...

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 ...

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 ...

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...

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...

Discover the Sensual World of Ruben: A Submissive Gentleman Awaits Hey there, Chicago! My name is Ruben, and I'm here to share a unique side of myself with you. Allow me to introduce my tantalizing fetish – the art of tickling. Tickling may seem like a simple pleasure, but for me, it's an electrifying experience that awakens all my senses. The gentle caress of...

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...

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 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...

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...

Explore Your Wildest Desires with Arleen from Chicago Hey there! I'm Arleen from Chicago, and I have a unique fetish that I absolutely love. It's something that sets my heart racing and makes me feel alive. I won't reveal what it is here, but trust me, it's something you won't forget. I'm a friendly and open-minded person who loves to explore differ...

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...

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...

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...

Explore Your Wildest Desires with Malinde Hey there! I'm Malinde from Chicago, and I have a unique fetish that I absolutely adore. I love indulging in Femdom, where I get to take control and dominate my submissive partner. It's such a thrilling experience for me! I'm a friendly and open-minded individual who loves to explore different ki...

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...

Passionate Swingers Looking for Fun in Chicago Hello there, I'm Clarisse from the windy city of Chicago. My husband and I are a dynamic duo who love to explore our deepest desires with other like-minded individuals. We are fun-loving, open-minded, and kink friendly - always ready for an adventure in the world of swinging. You can find us on F...

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...

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...

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'...

October 25th, 2025

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...

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...

Passionate Chicago Swingers Seeking Playmates Hey there, I'm Kellia from the windy city of Chicago, Illinois. My husband and I are fun-loving, open-minded, and kink friendly swingers looking to spice things up in the bedroom. We love exploring our fantasies and meeting new like-minded individuals who share our passion for the lifestyle. ...

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 ...

Indulge in Your Wildest Desires with Mureil Hey there! I'm Mureil from Chicago, and I have a unique fetish that sets my heart racing. I absolutely adore role-playing as a dominant woman in Femdom scenarios. The power exchange and control excite me in ways you can't even imagine! I'm a friendly and open-minded individual who loves to explo...

Sultry Transgender Beauty Seeks Connection Hey there! My name is Rayshell and I'm a proud transgender woman from Chicago, Illinois. I may not fit society's typical mold, but that's what makes me unique and special. 💃 I love exploring the vibrant LGBTQ community in Chicago and checking out local spots like Boystown for a fun night out. ...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Chicago? Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...

'>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...