Chicago, Illinois Alternative Sex Ads - BDSM, Trans & Swingers

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May 8th, 2025

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...

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...

Looking for Love and Adventure! Hey there! My name is Karie, and I'm a transgender woman living in the beautiful city of Chicago, Illinois. 🌆 So, let me tell you a bit about myself. I have a unique body type that will make you feel like you're hugging a fluffy cloud ☁️. I come from a diverse ethnic background, which adds...

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...

Explore Your Wildest Desires with Katee Hey there! I'm Katee, a fun-loving gal from Chicago who has a unique fetish that I can't wait to share with you. I absolutely adore role-playing and dressing up in leather outfits. The feeling of power and control it gives me is exhilarating! I love exploring different kinks and fetishes, so don'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 ...

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 Desires with Luci Hey there, Chicago! It's your girl Luci, and I've got something special to share with you. Are you ready to dive into a world of excitement and pleasure? Well, look no further because I'm here to make all your fantasies come true. Let me introduce myself - I'm a friendly and open-minded gal who l...

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...

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...

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....

Explore Kinks and Fetishes with Adella from Chicago Hey there! My name is Adella, and I'm a female swinger from Chicago, Illinois. My husband and I are friendly, open-minded, and always up for exploring new kinks and fetishes. We love meeting like-minded individuals who share our passion for adventure in the bedroom. You can find us in the swingers...

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...

Unleash Your Desires with Vikki from Chicago! Hey there, fellow thrill-seekers! I'm Vikki, a fiery female swinger hailing from the vibrant city of Chicago, Illinois. Together with my loving husband, we're here to take you on an unforgettable journey into the realm of pleasure and exploration. What sets us apart? Well, let me tell you. We are...

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 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...

Unleash Your Desires with Romeo Hey there, Chicago! It's your friendly neighborhood Romeo here, ready to share my unique fetish and explore the world of kinks and desires. Allow me to introduce myself - I'm a laid-back guy from the Windy City, Illinois, seeking an adventure with a Dominant woman who can embrace my submissive sid...

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...

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...

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 ...

New Body New Me M2F post-op in Chicago Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head with slender legs and curvy body. Want to come and join me for a drink? I love sex in my new gender!!! Seeking a local area man who will enjoy sex and passion with me. Message me online Natasha...

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 ...

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...

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 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...

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...

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...

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...

Calling all adventurous souls! Explore the world of Maisie from Chicago Hey there, curious minds of Chicago! My name is Maisie, and I'm here to invite you on a tantalizing journey into the realm of fetishes. Now, before we dive in, let me assure you that I'm friendly, open-minded, and always up for exploring new kinks and fetishes. So, buckle up and let's get started!...

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...

Kinky Chicago Girl Looking for BDSM Adventures My name is Libbey and I'm a kinky girl from Chicago, Illinois who loves exploring all kinds of fetishes. I enjoy being a Dominatrix and taking control in the bedroom, but I also love to switch things up and be a submissive little pet for the right person. Whippings, spankings, and roleplay are som...

Tempting Time with Del: Explore My Unique Fetish! Hey there, Chicago! It's your friendly neighbor Del, ready to share a secret with you. I've got a fetish that sets me apart from the rest, and boy, do I love it! Now, before we dive in, let me tell you a bit about myself. I'm an open-minded guy who loves to explore all sorts of kinks and fetishes...

Join Saundra in Chicago for Some Swinging Fun!
Hey there, I'm Saundra from the Windy City! My husband and I are a friendly and open-minded couple who love to explore all sorts of kinks and fetishes. We're always up for trying new things and meeting like-minded individuals who share our passion for adventure in the bedroom. You can find us on s...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I never knew how much I craved being a submissive male until I discovered the world of Elroy. My name is Elroy and I am from Chicago, Illinois. I am seeking a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to please a Mistress properly. You can find me in the Fre...

Femdom Mistress Shane - Explore Your Kinks with Me Are you ready to submit to a powerful and kinky Domina in Chicago, Illinois? I am Mistress Shane, a strict and sensual Femdom who loves to take control. Whether you crave being dominated, humiliated, or simply exploring your deepest desires, I am here to guide you on your journey of submission. A...

INTERACTIVE MAP: Kink Tracker in the Chicago Area! Chicago Alt & Kink Hookups Meet locals to explore the alternative lifestyles scene in the Chicago area. Meet members for friendship or to begin exploring the tantalizing world of kink! View our interactive map below to meet local Alt members who want to meet locals to explore various kinks and ...

Femdom Mistress Eddi's Kinky Domination Playground Are you ready to submit to a powerful and seductive Dominatrix in the Windy City? Look no further, for I am Mistress Eddi, your ultimate Femdom fantasy come to life. I thrive on exploring a wide range of kinks and fetishes, from strap-ons and pegging to whippings and spankings. I enjoy pushing b...

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...

Join Alisa from Chicago for an unforgettable swinging experience Hi there! My name is Alisa 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 interests and are always up for a good time. You can find us in the sw...

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 ...

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...

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 ...

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...

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...

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...

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 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......

Sparkling Transgender Beauty Looking for Love Hey there! I'm Lindie, a transgender woman from Chicago who loves exploring the city's diverse neighborhoods and trying out new restaurants. I may not fit into society's traditional gender norms, but that's what makes me unique and proud to be part of the LGBTQ community. I enjoy long walks by L...