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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June 14th, 2025

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...

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 ...

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...

Kinky Fetish Fun in Chicago! I'm Gracia, and I'm a wild and adventurous fetish enthusiast from the Windy City! I love exploring all things kinky and taboo, pushing boundaries and indulging in my deepest desires. Whether it's BDSM, domination, submission, roleplay, or age play, I'm always up for trying something new and exciti...

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...

Unleash Your Wildest Fantasies with Rosene from Chicago Hey there! My name is Rosene and I have a unique fetish that I absolutely adore. I love the feeling of silk against my skin, it sends shivers down my spine and makes me feel so alive. The way it glides over my body is just so sensual and exciting. I'm a friendly and open-minded person who loves t...

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...

Elegant Transgender Beauty Seeking Connection in Chicago Hey there! I'm Genna, a transgender woman from the Windy City. I may not fit society's narrow definition of beauty, but my unique body type and heritage make me who I am - and that's something special. 💃🏽 I love exploring LGBTQ-friendly spots in Chicago like Roscoe's Tavern or Sidetrack. Le...

Explore Kinks and Fetishes with Corry from Chicago Hey there, I'm Corry from Chicago! My husband and I are friendly, open-minded swingers who love to explore all kinds of kinks and fetishes. Whether you're new to the scene or a seasoned pro, we guarantee a good time filled with excitement and pleasure. You can find us in the swingers dating profil...

HMU for Sex in Chicago Newly Single and Ready to Mingle in Chicago Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Chicago, Illinois area then message me @BarbieSingle28.      ...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Fowler from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress to take control. I crave being forced into submission and taught how to properly please a Mistress. Whippings, domination, roleplay, and humiliation are some of the kinks I enjoy, but I'm also eage...

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...

Passionate Swingers Looking for Playmates in Chicago Hey there, I'm Marthe, and my husband and I are on the hunt for some sexy new friends to join us in our wild adventures. We're fun-loving, open-minded, and kink friendly - always up for trying new things and exploring our deepest desires. You can find us on FreeSexAds.com Swingers Lifestyle Prof...

Explore Your Wildest Desires with Britte Hey there! I'm Britte from Chicago, and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom, where I can take control and dominate in the bedroom. It's such a thrilling experience for me! I'm a friendly and open-minded person who loves to try new things and explor...

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...

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...

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......

Join Valentia for an Unforgettable Swinging Experience Hello there! My name is Valentia, 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 adventurous spirit. You can find us in the swingers dating prof...

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...

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...

Submissive Male Seeks Dominatrix for Kinky Fetish Fun I'm Dewitt, a submissive male from Chicago, Illinois, looking for a Dominant Female Mistress or Dominatrix to take control and show me the ropes. I crave being forced into submission and taught how to properly please a Mistress. Some of my favorite submissive kinks include roleplay, spankings, a...

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...

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 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...

Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Chicago Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very feminine...

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...

Sweet and Sensual Transgender Beauty Looking for Love Hey there, I'm Beverlee from Chicago, Illinois. I may not fit society's typical mold, but that's what makes me unique and special. I love being part of the LGBTQ community because it allows me to express myself authentically and embrace who I truly am. I enjoy long walks by Lake Michigan, explor...

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...

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...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Kraig from Chicago, Illinois, and I'm a submissive male looking for a Dominant Female Mistress or Dominatrix to take control and show me the ways of proper submission. I can be found on FreeSexAds.com Alt profiles under username kraigchic26575. I enjoy being tied up and spanked 🍑, roleplay...

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...

Exploring Kinky Fetishes with Molli I'm Molli, a kinky fetish enthusiast from Chicago, Illinois. I love diving into the world of BDSM, domination, and submission. Whippings, roleplay, and spankings are just a few of my favorite kinks to explore. But I'm always looking to push boundaries and try new things. If you're into age play o...

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 Lambert, a submissive male from Chicago, Illinois, looking for a Dominant Female Mistress to take control and force me into submission. I can be found on FreeSexAds.com Alt profiles under username lambertch13684. I crave the feeling of being dominated and controlled by a powerful woman who kn...

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...

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...

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 ...

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 👋...

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...

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...

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 ...

June 13th, 2025

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 ...

Join me for a night of exploration and pleasure Hello there, I'm Dawn from Chicago, Illinois. My husband and I are friendly, open-minded individuals who love to explore kinks and fetishes. We enjoy meeting new people who share our interests in the swinging lifestyle. You can find us in the swingers dating profiles under the member name dawnc401...

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, ...

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...

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

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...

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...

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...