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!
Show Ads In: Bloomington-Normal | Carbondale | Champaign-Urbana | Chicago | Decatur | Peoria | Quad Cities, IA/IL | Rockford | Springfield, IL
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 ...
Discover Lynnelle: A World of Fetishes and Exploration
Hey there! My name is Lynnelle, and I'm from the vibrant city of Chicago, Illinois. I wanted to take a moment to share something unique about myself - I have this intriguing fetish that adds a little spice to my life. Now, before you get all curious, let me tell you that it's called "Sensation Pla...
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...
Explore Your Desires with Manuel - A Submissive Gentleman from Chicago
Hey there! 👋 My name is Manuel, and I'm a friendly guy hailing from the vibrant city of Chicago, Illinois. Today, I want to share something unique about myself – my random fetish. 🌟
You see, I have this exhilarating fascination with role-playing as a naughty schoolboy. It's an innocent ye...
FtM seeking Princess Bride in Chicago FtM seeking Woman in Chicago
Hi, I'm Andy, age 33, FtM transgender man living in Chicago. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message @AndyFtM4P...
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!
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...
Submissive Male Seeks Dominatrix for Kinky BDSM Fun
My name is Herbert and I'm 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 in the FreeSexAds.com Alt profiles under username herbertchic49301.
I have always had...
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...
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...
Kinky Chicago Fetish Seeker
My name is Vikky and I'm a naughty little vixen from the Windy City looking for some kinky fun! I love exploring all kinds of fetishes and kinks, from BDSM to roleplay, spankings to crossdressing. I'm always up for trying new things and pushing boundaries.
You can find me on FreeSexAds.com Alt p...
Male sub looking for Mistress in Chicago Male sub seeking Mistress in Chicago
I am new in town. My name is Jon-boy. I had to leave my old Dominatrix behind and while I miss Her guidance and affection, I would love to find a new Mistress I can serve. If you are looking for a new sub or another sub to add to your list I would love to be con...
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...
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...
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...
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...
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 ...
SHEMALE HOOKUPS! Wanna Have a Great Time in Chicago, Illinois? HOT! SHEMALE HOOKUPS
"The girl with a naughty little secret in her panties!"
SIGNUP FREE: INSTANT ACCESS! Shemale Profiles
Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up!
Join free for Instant Access to the Chic...
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...
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...
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...
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...
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...
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...
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...
Discover the Enchanting World of Paulie from Chicago!
Hey there! It's Paulie, your friendly fetish explorer from the Windy City. I'm here to share a little secret with you - I have a unique and exciting fetish that sets my heart racing and ignites my imagination.
Now, let me tell you what I love about it. This fetish of mine takes me on thrilling a...
Sultry Transgender Beauty Looking for Love in Chicago
Hey there! I'm Lora, a confident and sassy transgender woman living in the Windy City. I may not fit society's standards of beauty, but I rock my curves with pride. Being transgender has opened my eyes to a whole new world of self-discovery and acceptance, and I wouldn't have it any other way.
I...
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'...
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...
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...
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 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...
Discover the Sensual World of Ruben: A Submissive Gentleman Awaits
Hey there, Chicago! My name is Ruben, and I'm here to share a unique side of myself with you. Allow me to introduce my tantalizing fetish – the art of tickling.
Tickling may seem like a simple pleasure, but for me, it's an electrifying experience that awakens all my senses. The gentle caress of...
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....
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 ...
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
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...
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...
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 Kinks and Fetishes with Nancee from Chicago
Hey there, I'm Nancee from Chicago, Illinois. My husband and I are friendly, open-minded swingers who love to explore all kinds of kinks and fetishes. Whether you're a seasoned pro or just dipping your toes into the lifestyle, we welcome you with open arms (and maybe a few other things 😉). You ...
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...
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...
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...
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...
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...
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.
...
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...
Kinky Chicago Fetish Seeker
I'm Jany, a kinky girl from Chicago who loves exploring all kinds of fetishes and kinks. Whether you're into BDSM, domination, submission, roleplay, spankings, or anything else that gets your heart racing, I'm your girl. I love pushing boundaries and trying new things in the bedroom.
One of my ...
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 ...