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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December 25th, 2025

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...

Seeking Kinky Fun in Chicago! Are you ready to explore your deepest desires with a kinky girl named Corie? I'm from Chicago, Illinois, and I love all things fetish-related. Whether you're into BDSM, domination, submission, roleplay, or any other kinks, I'm your girl! You can find me on FreeSexAds.com Alt profiles under userna...

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...

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...

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 ...

Passionate Swingers Looking for Playmates in Chicago Hello there, I'm Eveline from the windy city of Chicago. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We believe that life is too short not to indulge in all the pleasures it has to offer, especially when it comes t...

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...

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...

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...

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...

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...

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......

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...

Looking for Love and Adventure in the Windy City! 🌈 Hey there, lovely people of Chicago! My name is Opaline, and I'm a proud transgender person who's ready to embrace life, love, and everything in between. 💖 So, let me tell you a bit about myself. I have a unique body type that will make you want to give me endless bear hugs. 🐻 My ethnicity ...

Gorgeous, Passable Trans in Chicago 😍 Gorgeous Passable Trans MtF for Man in Chicago 😍 I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!  I'm ki...

27 y/o Sexy Hung Crossdresser in Chicago Hung Crossdresser for Male in Chicago Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a sexy ...

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...

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...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Chicago I will help you unwind and create a cozy environment for you! I am 36DD, 7" and can give you so much pleasure. View my Transgender World profile and message me for my pics! @GayleTGirl Gayle <3    Transgender World Profile Username: GayleTGi...

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...

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...

Raunchy Shemale Seeking Local Man for Wild Fun Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm Kailey and I'm ready to show you a good time. I'm a sexy shemale from Chicago, Illinois, seeking a local man who can handle my insatiable appetite for pleasure. When it comes to sex, I love it a...

Lon - Explore Your Deepest Desires with Me! Hey there, Chicago! My name is Lon, and I've got a unique fetish that will make your heart race and your mind wander. You won't find anyone quite like me, so buckle up for an unforgettable adventure! I have this incredible fascination with feathers. Yes, you read that right – feathers! There's ...

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...

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...

'>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...

INTERACTIVE MAP: Kink Tracker in the Chicago Area! Chicago Alt & Kink Hookups Meet locals to explore the alternative lifestyles scene in the Chicago area. Meet members for friendship or to begin exploring the tantalizing world of kink! View our interactive map below to meet local Alt members who want to meet locals to explore various kinks and ...

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...

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...

Want to Fuck My Wife? Let's Swap in Chicago Wife Swaps in Chicago Attractive, adventurous and athletic couple in the Chicago area seeks swinger hookups for social activities and the explore the local swinging lifestyle. He is Thomas, age 29, a self-employed graphic artist. Fit and trim, loves sex!  She is Heather, age 27, employed as ...

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...

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...

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 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 👋...

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'...

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...

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...

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...

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 ...