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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August 13th, 2025
Explore Your Desires with Frederik from Chicago!
Hey there! My name is Frederik, and I've got a unique fetish that I can't wait to share with you. I'm from the vibrant city of Chicago, Illinois, and I'm looking for a special someone to join me on this exciting journey.
Now, let's talk about my fetish. It's something that really gets my heart ra...
Seeking a Local Man for Hot Shemale Fun in Chicago
Are you looking for a wild time with a sexy shemale? Well, look no further because I'm here to fulfill all your naughty desires. My name is Carlynne and I'm a hot tranny ready to play with you.
I love getting down and dirty, so if you're into some kinky fun, I'm your girl. I enjoy giving blowjobs...
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 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 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...
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 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...
Join Meggi for an Unforgettable Swinging Experience in Chicago!
Hey there, I'm Meggi 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 new adventures and meeting like-minded individuals who share our passion for excitement and pleasure. You can find us on swin...
Transgender Beauty Looking for Love in the Windy City
Hey there, lovely people of Chicago! My name is Dory, and I'm a proud transgender woman who's ready to dive into the dating scene. 💃🌈
As a true Chicagoan, I embrace the city's diverse culture and vibrant energy. Whether it's exploring art at the Art Institute or catching a Cubs game at Wrig...
Submissive Male Seeks Dominatrix for Kinky BDSM Fun
I'm Russ 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 and fetishes that I enjoy include roleplay ðŸŽ, ...
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...
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, ...
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...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...
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, ...
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Browse strap-on profiles of women and men who enjoy hot role reversals!
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Submissive Male Seeks Dominatrix for Kinky Fun
I'm Flint 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 submission. I can be found on FreeSexAds.com Alt profiles under username flintchic71595.
I enjoy being dominated in various ways, such as whipp...
Discover the Magic of Love with Rhianon!
Hey there, lovely people of Chicago! My name is Rhianon and I'm thrilled to be part of this amazing LGBTQ community. 💖 Being transgender has allowed me to embrace my true self and experience life from a unique perspective. It's been quite a journey, but I wouldn't change it for the world!
I'm ...
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...
Explore Kinks and Fetishes with Sondra in Chicago
Hey there, I'm Sondra from Chicago! My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. Whether you're new to the scene or a seasoned pro, we're always up for trying something new and exciting.
You can find us in the swingers dating profiles...August 12th, 2025
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...
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...
Transgender Beauty Looking for Love
Hey there! My name is Mandi and I'm a transgender woman living in Chicago, Illinois. I have a curvy body and I love embracing my Latina heritage. You can check out my pics at my personal profile page @mandic21518.
I'm proud to be part of the LGBTQ community and I enjoy being able to express my tr...
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 ...
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.
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Passionate Swingers Seeking Playmates in Chicago
Hey there, I'm Kellsie from the Windy City, and my husband and I are on the lookout for some sexy new friends to join us in our wild adventures. We're a fun-loving couple who thrive on exploring our deepest desires and fantasies with like-minded individuals. Our open-mindedness knows no bounds, an...
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...
Elegantly Transcending Boundaries
Hey there! I'm Jennine, a transgender woman from Chicago, Illinois. I love exploring the diverse neighborhoods of the city like Wicker Park, Lakeview, and Pilsen. If you're looking for someone who enjoys being their authentic self and embraces the LGBTQ community, then look no further!
I find bea...
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...
Elegant and Enchanting Trans Beauty Looking for Love
Hey there! I'm Liza, a stunning transgender woman living in the bustling city of Chicago, Illinois. My body is curvy and my nationality is Mexican-American. I love being part of the LGBTQ community because it allows me to express my true self without fear or judgment.
I'm looking for someone who ...
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...
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...
Unleash Your Wildest Fantasies with Myrle from Chicago
Hey there, I'm Myrle, a female swinger from the Windy City. 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.
You can find us i...
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 ...
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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! ðŸ¤
There's something incredibly thrilling about being tickled, feeling those...
Explore Your Wildest Desires with Cassey from Chicago
Hey there! I'm Cassey, a friendly and open-minded gal from Chicago who has a unique fetish that I absolutely adore. I have a thing for wearing latex clothing and exploring the world of latex fetishism. The feeling of the tight material against my skin just drives me wild!
I love to explore diffe...
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 ...
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...
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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 ...
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...
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 ...
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...
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...
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.
...
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 ...
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, ...
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...