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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January 14th, 2026

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...

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...

Unleash Your Dominant Side with Butch from Chicago! Hey there, ladies of Chicago! My name is Butch, and I've got a unique fetish that might just pique your interest. Now, before we dive in, let me tell you a bit about myself. I'm a friendly and open-minded guy who loves to explore all sorts of kinks and fetishes. Life's too short not to try new thi...

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...

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...

Explore Your Wildest Desires with Kaylee from Chicago Hey there! I'm Kaylee, a fun-loving gal from Chicago with a unique fetish that will blow your mind. I have a thing for foot worship 🦶 and let me tell you, it's my ultimate turn-on. There's something about having my feet pampered and worshipped that drives me wild! I'm super friendly and open-...

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 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...

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...

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...

Explore Your Wildest Desires with Katee Hey there! I'm Katee, a fun-loving gal from Chicago who has a unique fetish that I can't wait to share with you. I absolutely adore role-playing and dressing up in leather outfits. The feeling of power and control it gives me is exhilarating! I love exploring different kinks and fetishes, so don't...

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...

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...

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 Candace from Chicago Hey there! I'm Candace, a fun-loving gal from Chicago with a unique fetish that will blow your mind. I have a thing for latex and leather - there's just something about the feel of it against my skin that drives me wild! I love the power and confidence it gives me, and how it can transform a regul...

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...

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 ...

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...

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...

MEET LOCAL FREAKS - BDSM, Fetish, Femdom, & Kinksters [FREE PROFILES] Meet Local Freaks to Work Out Your Kinks! Your guide to the Chicago bondage, femdom and fetish scene We live the kink lifestyle. We love the power, the submission and the kinky pleasures. Come meet local kinksters for friendship or passion.  thebdsmguide.com BDSM Femdom ...

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 ...

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...

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 ...

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...

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 ...

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...

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...

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...

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 ...

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...

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 ...

'>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: 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...

Cecilla's Kinky Fetish Adventures I'm Cecilla from Chicago, and I have some wild fetishes that I love exploring. You can find me on FreeSexAds.com Alt profiles under username cecillach44361. I'm into all things BDSM, from whippings to domination and submission. One of my favorite kinks is roleplay 🎭. I love getting into chara...

Passion Seekers in Chicago Are you ready to spice up your sex life and explore your wildest fantasies? Look no further, because my husband and I are the fun-loving, open-minded swingers you've been searching for. My name is Jo Ann, and I hail from the vibrant city of Chicago, Illinois. We are a couple who thrives on adven...

Explore Your Desires with Kynthia Hey there, Chicago! My name is Kynthia, and I have a unique fetish that I can't wait to share with you. Now, I won't tell you what it is just yet, but trust me, it's something special that will make your heart race and your imagination run wild. First things first, let me tell you a bit about mys...

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 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...

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...

Discover the Magic of Love with Keelia! 💖 Hey there! My name is Keelia, and I'm here to find that special someone who's ready to embark on an incredible journey filled with love, laughter, and endless adventures. 🌈 So, let me tell you a bit about myself. I'm a fun-loving transgender woman from Chicago, Illinois. With my radiant smile ...

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...

Join Augustine for an Unforgettable Swinging Experience Hello there! My name is Augustine 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 creating a safe and exciting environment for like-minded individuals to come together and in...

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 ...

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...

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 ...

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 ...

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...

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 ...

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...