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...

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...

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...

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...

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...

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...

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 ...

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 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...

Cybil's Kinky Desires I'm Cybil, a sultry vixen from the windy city of Chicago, Illinois. I have a passion for exploring all things taboo and indulging in the world of kinks and fetishes. If you're looking to dive into a world of pleasure and pain, then look no further because I'm your girl. I thrive on BDSM play, whe...

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 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 ...

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...

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......

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 ...

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 ...

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...

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 ...

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 ...

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...

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...

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...

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...

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....

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...

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 ...

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...

Unleash Your Desires with Rose from Chicago! Hey there, curious souls of Chicago! It's your friendly neighborhood fetish enthusiast, Rose. I'm here to share a little secret with you - I have a unique fetish that sets my heart racing and ignites my imagination. Brace yourselves, because things are about to get interesting! Now, let me start ...

Meet Illinois Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans Clubs Meet Illinois Transexuals Online!  Meet Illinois transexuals online at AmericanTransexuals.com. Our web development team includes transexual women and male trans admirers, so we have a unique understanding of transgender attraction. We have created an online community where you can meet Illino...

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...

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...

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...

Explore Your Wildest Desires with Leelah Hey there, I'm Leelah from Chicago, Illinois! I have a unique fetish that I absolutely adore - I love dressing up in latex and dominating my partner. It's such a thrill to take control and explore different power dynamics. I'm friendly, open-minded, and always up for trying new things. I'm intri...

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...

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...

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 ...

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...

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 ...

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-...

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...