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 5th, 2025

Domme looking for male sub who wants to be owned Domme for male sub in Chicago I am Mistress Danielle. FemDom is My lifestyle, not something I do merely for fun. I have an opening in My dungeon for a submissive male. Send your photo along with an explanation of your kinks and fetishes and how you believe you can serve Me.  This is a serious...

Kinky Fetish Fun in Chicago My name is Audie, and I'm a kinky fetish lover from Chicago, Illinois. I have a passion for exploring all kinds of naughty desires and pushing boundaries in the bedroom. You can find me on FreeSexAds.com Alt profiles under the username audiechic42222. I have a few kinks that really get me going, ...

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 ...

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...

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...

Kelci's Kinky World Hey there! I'm Kelci from Chicago, and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom, where I get to take control and dominate my submissive partner. It's such a thrill for me to be in charge and see them surrender to my every command. I'm a friendly and op...

TS M2F Top in Chicago TS Top Seeking Man in Chicago I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body.  Non op functional, nice big ladystick for your pleasure! 😈  Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kinks and ...

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......

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...

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...

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. ...

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...

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...

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 ...

Hot Shemale Seeking Local Man for Wild Fun in Chicago Hey there, I'm a sexy shemale named Cammy looking for a man who can handle all my dirty desires. I love being on top and taking control, but I also enjoy getting down on my knees and giving sloppy blowjobs. Let's explore each other's bodies and make each other cum over and over again. I'm into ever...

Kinky Chicago Fetish Seeker Looking for Playmates I'm Lyda, a kinky gal from the Windy City looking to explore all sorts of naughty fun with like-minded individuals. I love indulging in BDSM, domination, and submission play. There's nothing quite like the thrill of being in control or surrendering to someone else's desires. I have a particular ...

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...

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...

Chicago Femdom Mistress Stormy Seeks Submissive Men for Kinky Fun Are you ready to submit to a powerful and dominant woman? Look no further, I am Mistress Stormy from Chicago, Illinois, and I am here to fulfill all your deepest fantasies. As a seasoned Dominatrix, I thrive on exploring kinks and fetishes with willing submissives. Whether you crave being humiliat...

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 ...

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...

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...

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 ...

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...

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...

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...

Hot Shemale Looking for Local Man to Play With Hey sexy, I'm Merrill and I'm a naughty shemale from Chicago looking for a man who can handle all that I have to offer. I love getting down and dirty, so if you're into some wild fun, then I'm your girl...err, shemale!When it comes to sex, I'm open to just about anything. I love giving and receiving...

Glory's Kinky Desires Hey there, my name is Glory and I'm a kinky girl from Chicago, Illinois. I love exploring all kinds of fetishes and kinks, from BDSM to roleplay to age play. I can be your Mistress or your submissive, whatever you desire. I enjoy whippings, domination, submission, spankings, and so much more. There'...

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 ...

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....

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 ...

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...

Explore Your Desires with Hollie from Chicago! Hey there! My name is Hollie, and I'm a friendly and open-minded woman from the beautiful city of Chicago, Illinois. I wanted to share something unique about myself - I have a fascinating fetish that truly ignites my passions! Now, before I tell you what it is, let me just say that exploring dif...

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...

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...

Kinky Fetish Fun in Chicago My name is Lorilyn and I'm 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. There's nothing I enjoy more than taking control and giving out some well-deserved spankings. 🍑 I have a wild...

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...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun My name is Kurt and I'm a submissive male from Chicago, Illinois looking for a Dominant Female Mistress or Dominatrix to force me into submission. I can be found on FreeSexAds.com Alt profiles under username kurtc73936. I love being dominated and controlled by a powerful woman who knows how to p...

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...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Robb, a submissive male from Chicago looking for a Dominant Female Mistress or Dominatrix to take control and show me the ways of submission. I crave being forced into my place, learning how to properly please a Mistress, and exploring all sorts of kinky fetishes and roleplay scenarios. I en...

Explore Your Wildest Desires with Roselyn from Chicago Hey there, I'm Roselyn from Chicago, and I have a unique fetish that I absolutely love! I adore dressing up in latex outfits and dominating my partner. The feeling of power and control gets me so excited! I'm a friendly and open-minded person who loves to explore different kinks and fetishes. I'...

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...

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 ...

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...

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...

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...

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...