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!

Home / Alternative Sex Ads /

Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL

March 9th, 2025

Explore Your Wildest Desires with Camille Hey there! I'm Camille from Chicago, and I have a unique fetish that I absolutely adore. It's all about feet - the feeling of soft skin under my fingertips and the power it gives me to make someone weak at the knees. I love how it can be both sensual and dominant at the same time. I'm a friendly ...

Explore Your Wildest Desires with Lorena from Chicago Hey there, I'm Lorena and I have a unique fetish that I absolutely adore. It's not something you hear about every day, but it really gets me going. I love exploring different kinks and fetishes, and I'm always open to trying new things. I'm friendly, open-minded, and always up for a good time. On...

Explore Your Deepest Desires with Lindi in Chicago! Hey there, fellow kinksters of Chicago! My name is Lindi, and I'm here to tell you about my unique fetish that will blow your mind. Brace yourself for a tantalizing journey into the world of Femdom! I am a friendly and open-minded woman who loves to explore different kinks and fetishes. There's s...

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-...

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...

Kinky Dominatrix seeks puppy to train DOMINATRIX SEEKS PUPPY TO TRAIN  Are you the submissive little puppy I have been looking for? I am A Power Domme looking for the one to meet my needs. I am on this site, because I know too often you seek an escape... with someone you can relinquish your power to. I know there's a lot of pressu...

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...

Unleash Your Desires with Seline from Chicago! Are you ready to embark on a tantalizing journey of pleasure and exploration? Look no further! My name is Seline, and I'm here to invite you into a world of uninhibited passion and excitement. Located in the vibrant city of Chicago, Illinois, my husband and I are friendly, open-minded individual...

Hot Shemale in Chicago Looking for Wild Fun! I'm a sexy shemale named Drew who is seeking a local man for some hot and steamy action. I love to get down and dirty, so if you're ready for a wild ride, I'm your girl! I enjoy everything from passionate kissing to rough anal play. I love giving and receiving blowjobs, riding a thick cock, and ...

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...

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...

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...

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 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...

Submissive Male Seeks Dominatrix for Kinky Rollins Fetish Fun I'm Rollins from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control. I crave being forced into submission and taught how to properly please a Mistress. I can be found on FreeSexAds.com Alt profiles under username rollinsc80949. I enjo...

Hot Shemale Vivian Looking for Naughty Fun in Chicago Are you ready for a wild time with a sexy shemale in the Windy City? I'm Vivian, and I'm on the hunt for a local man who can handle all of my filthy desires. I love to get down and dirty, exploring every inch of your body with my throbbing cock and tight ass. I'm a top who loves to take control, ...

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 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 ...

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 ...

Explore Your Desires with Eddie from Chicago! Hey there, fellow kinksters! My name is Eddie, and I'm here to tell you about a unique fetish that gets my heart racing. Allow me to introduce you to my passion for tickling! 🤭 There's something incredibly thrilling about the sensation of being tickled. It's like a rollercoaster ride for my s...

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...

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. ...

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 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. ...

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...

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...

A Sensual Journey with Maddy Hey there, I'm Maddy, a fun-loving transgender babe from Chicago. I may not fit society's standards of beauty, but my confidence and charm will sweep you off your feet. 🌈 I love exploring the diverse LGBTQ scene in the city, whether it's dancing the night away at Berlin Nightclub or enjoying a...

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 ...

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...

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...

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 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 ...

Kinky Fetish Fun with Chrissa in Chicago Hey, it's Chrissa here from Chicago! If you're looking for someone to explore your wildest kinks and fetishes with, then look no further. I love diving into the world of BDSM, domination, and submission. Whippings, roleplay, and spankings are just a few of my favorite things. But I'm always open to ...

Join Renell from Chicago for a Sensual Adventure Hello there, I'm Renell from the windy city of Chicago. My husband and I are a friendly and open-minded couple who love to explore all sorts of kinks and fetishes. We believe in embracing our desires and living life to the fullest. You can find us on swingers dating profiles under the member name...

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...

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...

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...

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...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Mendel from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control and force me into submission. I can be found on FreeSexAds.com Alt profiles under username mendelchi94261. I enjoy being dominated in various ways, such as whippings, ...

Sexy Transgender in Chicago Looking for Love Hey there! I'm Kathie, a fun-loving transgender woman living in the Windy City. I may not fit society's norms, but that's what makes me unique and fabulous. I embrace my LGBTQ identity and love being part of such a diverse community. I enjoy cozy coffee dates at local cafes like Intelligentsia or...

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 ...

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...

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...

Explore Your Wildest Desires with Maxie from Chicago Hey there! I'm Maxie, a friendly and open-minded gal from Chicago who loves to explore all kinds of kinks and fetishes. One of my favorite fetishes is foot worship - there's something so sensual and intimate about having my feet pampered and adored. But that's just the tip of the iceberg! I'm alwa...

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 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...

Kinky Fetish Fun in Chicago Hey there, it's Lilia from the windy city of Chicago! I'm a kinky girl who loves to explore all sorts of fetishes and kinks. You can find me on FreeSexAds.com Alt profiles under username liliach99616. I have a thing for BDSM and domination. There's nothing more thrilling than taking control and mak...

'>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 ...

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...

Chicago Strap On Sex Hookups Chicago Strap On Dating Profiles Browse strap-on profiles of women and men who enjoy hot role reversals!   ...