Madison, Wisconsin Alternative Sex Ads - BDSM, Trans & Swingers

Browse Madison, Wisconsin 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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  • October 16th, 2025
  • Transgender Beauty Seeking Connection in MadisonTransgender Beauty Seeking Connection in Madison Hey there! My name is Ventura, and I'm a transgender individual living in the beautiful city of Madison, Wisconsin. 🌈 I'm here to find someone special who appreciates all the unique qualities that being trans brings to my life. Being part of the LGBTQ community has taught me so much about acce...
  • Ready for an Adventure? LetReady for an Adventure? Let's Connect! 🌈 Hey there! My name is Mollee and I'm a transgender woman living in the beautiful city of Madison, Wisconsin. I'm excited to put myself out there and see who's ready to join me on this journey called life. So, let me tell you a bit about myself! Physically, I have a curvy body that embraces my fem...
  • Explore Kinks and Fetishes with Tallie from MadisonExplore Kinks and Fetishes with Tallie from Madison Hello there! My name is Tallie, and I am a female swinger from Madison, Wisconsin. My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. We believe that life is too short to not indulge in our deepest desires. If you're looking for a fun and a...
  • Sexy Shemale Looking for a Hot Stud to Play WithSexy Shemale Looking for a Hot Stud to Play With Are you ready for some wild and kinky fun with a naughty shemale in Madison, Wisconsin? My name is Lyndsie and I'm on the hunt for a local man who can handle all my dirty desires. I love getting down and dirty, exploring every inch of your body and fulfilling all your wildest fantasies. From top t...
  • INTERACTIVE MAP: Transexual Tracker in the Madison Area!INTERACTIVE MAP: Transexual Tracker in the Madison Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Madison 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...
  • Passionate Swingers Looking for PlaymatesPassionate Swingers Looking for Playmates Hello there, I'm Anetta from Madison, Wisconsin. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We are active members on FreeSexAds.com Swingers Lifestyle Profiles under the username anetta11923, where you can find us...
  • Transcend into Love with SusannTranscend into Love with Susann Hey there! I'm Susann, a transgender woman from Madison, Wisconsin. I may not fit society's mold of what a woman should look like, but I embrace my unique body type and ethnicity with pride. Being part of the LGBTQ community has allowed me to connect with others who understand and accept me for wh...
  • Explore Your Wildest Desires with Margaret from MadisonExplore Your Wildest Desires with Margaret from Madison Hey there, I'm Margaret from Madison, and I have a unique fetish that will blow your mind. I absolutely adore wearing latex clothing and exploring the world of latex fetishism. The feeling of the tight material against my skin sends shivers down my spine and makes me feel powerful and sexy. I'm ...
  • Passionate Swingers Looking for Playmates in Madison, WIPassionate Swingers Looking for Playmates in Madison, WI Hey there, I'm Korrie from Madison, Wisconsin. My husband and I are a fun-loving couple who are open-minded and kink-friendly. We love exploring our sexuality and meeting new like-minded individuals who share our passion for the swinging lifestyle. You can find us on FreeSexAds.com Swingers Life...
  • Raunchy Shemale Meagan Looking for Hot Fun in MadisonRaunchy Shemale Meagan Looking for Hot Fun in Madison Are you ready to have some wild and kinky fun with a sexy shemale like me? My name is Meagan, and I'm a hot tranny looking for a local man in Madison who can handle all of my desires. I love getting down and dirty, so if you're into that too, then we'll be a perfect match. I'm a top shemale who l...
  • LetLet's Embrace Our True Selves Together Hey there, I'm Paule from Madison, Wisconsin. I identify as a transgender woman and I love everything about being part of the LGBTQ community. I enjoy exploring new places in Madison like the Olbrich Botanical Gardens or grabbing a bite to eat at The Old Fashioned. If you're looking for someone wh...
  • Join Adella from Madison for Some Swinging Fun!Join Adella from Madison for Some Swinging Fun! Hey there, I'm Adella from Madison, Wisconsin. 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 new people who share our interests. You can find us in the swingers dating profiles under th...
  • Looking for Love as a Transgender: LetLooking for Love as a Transgender: Let's Explore Madison Together! Hey there! 👋 My name is Michaella, and I'm a proud transgender woman living in the beautiful city of Madison, Wisconsin. 🌆 I wanted to take a moment to tell you a little bit about myself and why I think we could be a great match. Physically, I have an hourglass figure with curves in all the...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Madison 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 ...
  • Kinky Fetish Fun with Brittany from MadisonKinky Fetish Fun with Brittany from Madison I'm Brittany, a kinky girl from Madison who loves exploring all kinds of fetishes and kinks. I have a passion for BDSM, domination, submission, and roleplay. Whippings, spankings, and humiliation get me excited like nothing else. I love being a Mistress and taking control, but I also enjoy being a...
  • Mistress seeks Madison male sub for BDSM and trainingMistress seeks Madison male sub for BDSM and training Mistress seeking male sub in Madison 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...
  • Submissive Male Seeks Dominatrix for Kinky FunSubmissive Male Seeks Dominatrix for Kinky Fun I'm Zachery from Madison, Wisconsin, and I am 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. Some of my favorite submissive kinks include roleplay, spankings, and age play....
  • Seeking Local Man for Shemale Fun in MadisonSeeking Local Man for Shemale Fun in Madison Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm Shay, a sexy and insatiable shemale from Madison, Wisconsin, seeking a local man for some steamy encounters. I love getting down and dirty with a man who knows how to please me in every way possib...
  • Explore Kinks and Fetishes with Celine from MadisonExplore Kinks and Fetishes with Celine from Madison Hey there! I'm Celine, a female swinger from Madison, Wisconsin. My husband and I are a friendly and open-minded couple who love to explore all kinds of kinks and fetishes. Whether you're into BDSM, role-playing, or something else entirely, we're always up for trying new things. You can find us i...
  • Explore Your Wildest Desires with Neila!Explore Your Wildest Desires with Neila! Hey there! My name is Neila and I have a unique fetish that I absolutely love - tickling! There's something about the sensation of being tickled that just drives me wild. It's like a mix of pleasure and excitement that I can't get enough of. I'm a friendly and open-minded person who loves to expl...
  • New Body New MeNew Body New Me M2F post-op in Madison 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...
  • Raunchy Shemale Dyana Seeking Local Man for Wild FunRaunchy Shemale Dyana Seeking Local Man for Wild Fun Looking for a hot guy in Madison who can handle a naughty shemale like me? I'm Dyana, and I'm ready to show you a good time. Let's get down and dirty together for some mind-blowing action. I love being both top and bottom, so we can switch things up and explore all our desires. From deepthroati...
  • Unleash Your Desires with Aurel in Madison!Unleash Your Desires with Aurel in Madison! Hey there! Are you ready to dive into a world of pleasure and explore your deepest desires? Look no further, because I'm here to introduce you to the enchanting world of Aurel. 😍 I'm a friendly and open-minded woman from Madison, Wisconsin, who loves to embrace her unique fetishes. And let me ...
  • Shemale Nightclubs Near You in Madison, WisconsinShemale Nightclubs Near You in Madison, Wisconsin Shemale Nightclubs Near You in Madison, Wisconsin Shemale Clubs Near You in Madison, Wisconsin 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 ...
  • Submissive Male Seeks Dominatrix for Kinky BDSM FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun Are you a Dominant Female Mistress or Dominatrix looking for a submissive male to play with? Look no further, because I am Edward from Madison, Wisconsin, and I am ready to submit to your every command. I can be found on FreeSexAds.com Alt profiles under username edwardma52357. I have always had ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun I'm Pandora, a sexy shemale from Madison looking for a man who can handle all of me. I love getting down and dirty, exploring every inch of each other's bodies. When it comes to sex, I'm open to trying anything and everything. From passionate kissing and deepthroating to rough anal play and intens...
  • Submissive Male Seeks Dominatrix for Kinky BDSM FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Leigh, a submissive male from Madison, Wisconsin looking for a Dominant Female Mistress or Dominatrix to force me into submission. I want to be taught how to properly please a Mistress and explore all kinds of kinky fetishes and roleplay scenarios. I enjoy being spanked, whipped, and humiliat...
  • Kinky Fetish Fun in MadisonKinky Fetish Fun in Madison Hey there, it's Cherin from Madison, Wisconsin. I'm a kinky girl looking for some like-minded individuals to explore all sorts of fetishes with. You can find me on FreeSexAds.com Alt profiles under username cherinmad60417. I have a passion for BDSM, domination, and submission. I love whippings, r...
  • Domme looking for male sub who wants to be ownedDomme looking for male sub who wants to be owned Domme for male sub in Madison 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...
  • Kinky Dominatrix seeks puppy to train 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...
  • Kinky Fetish Fun in Madison!Kinky Fetish Fun in Madison! I'm Aleen, and I'm a kinky little minx from Madison, Wisconsin. I love exploring all sorts of fetishes and kinks, from BDSM to roleplay to age play. I get a thrill out of dominating my submissives and giving them a good spanking when they misbehave. But I also enjoy being a submissive myself, let...
  • Want to Fuck My Wife? LetWant to Fuck My Wife? Let's Swap in Madison Wife Swaps in Madison Attractive, adventurous and athletic couple in the Madison 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 ...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Madison Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Submissive Male Seeks Dominatrix for Kinky BDSM Fun<br>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 BDSM. My name is Marlin, and I am from Madison, Wisconsin. I am on the hunt for a Dominant Female Mistress or Dominatrix who can force me into submission and teach me how to properly please a Mistress. Some of ...
  • Spark Up Some Magic with Lita!Spark Up Some Magic with Lita! Hey there! I'm Lita, a transgender cutie from Madison, Wisconsin. I may have a curvy body, but my personality shines brighter than the sun! 🌟 I love exploring new places in Madison like the Olbrich Botanical Gardens or grabbing a cup of coffee at Colectivo Coffee. Being part of the LGBTQ comm...
  • Explore Your Desires with MerielExplore Your Desires with Meriel Hey there, Madison! My name is Meriel and I have a secret that I can't wait to share with you. Are you ready for a tantalizing adventure? Well, buckle up because here we go! I have this unique fetish that makes me feel alive and excited. It's like an electrifying current running through my veins,...
  • Passionate Swingers Looking for Playmates in MadisonPassionate Swingers Looking for Playmates in Madison Hey there, I'm Pearla, a fun-loving and open-minded swinger from Madison, Wisconsin. My husband and I are always up for exploring new adventures in the lifestyle, and we're looking for like-minded individuals or couples to join us for some steamy fun. We're both kink-friendly and love to indulge ...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Madison? 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...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Looking for a hot stud to fulfill all my dirty desires. I'm Danica, a sexy shemale from Madison, Wisconsin. I love getting down and dirty with a man who can handle me in the bedroom. You can find me in the FreeSexAds.com Shemale Profiles at danicama22701. I'm a top who loves to dominate and take ...
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  • FtM seeking Princess Bride in MadisonFtM seeking Princess Bride in Madison FtM seeking Woman in Madison Hi, I'm Andy, age 33, FtM transgender man living in Madison. 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...
  • Submissive Male Seeks Dominatrix for Kinky BDSM FunSubmissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Rhett, a submissive male from Madison, Wisconsin, looking for a Dominant Female Mistress or Dominatrix to take control and guide me into the world of submission. I crave being forced into my place and taught how to properly please a Mistress. I enjoy kinks such as whippings, roleplay, and hu...
  • Kinky Fetish Fun with Tricia in Madison!Kinky Fetish Fun with Tricia in Madison! I'm Tricia, and I'm a kinky little vixen from Madison looking for some naughty fun. I have a wild side that craves all kinds of fetishes and kinks. From BDSM to roleplay, I love exploring new experiences. I enjoy being a Dominatrix, taking control and giving out whippings to my willing submissive...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Madison 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...
  • MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissiveMISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Madison Dominatrix Message Me Online: MistressKim4subMadison Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......
  • October 15th, 2025
  • Spark Up Some Chemistry with Marleen from Madison!Spark Up Some Chemistry with Marleen from Madison! Hey there! I'm Marleen, a fun-loving transgender gal from Madison, Wisconsin. I may not fit society's mold, but that's what makes me unique and special. 💃🏽 I love exploring the LGBTQ community in Madison and checking out cool spots like Shamrock Bar & Grille or The Ohio Tavern for a fun nig...
  • Passionate Swingers Looking for Playmates in MadisonPassionate Swingers Looking for Playmates in Madison Hey there, I'm Karyn, a fun-loving and open-minded swinger from Madison, Wisconsin. My husband and I are always up for new adventures and exploring our kinks with like-minded individuals. We believe that life is too short to not indulge in all the pleasures it has to offer. You can find us on Fre...
  • Submissive Male Seeks Dominatrix for Kinky AdventuresSubmissive Male Seeks Dominatrix for Kinky Adventures My name is Jordan and I am a submissive male from Madison, Wisconsin. I am on the hunt for a Dominant Female Mistress or Dominatrix who can force me into submission and teach me how to properly please a Mistress. I can be found on FreeSexAds.com Alt profiles under username jordanm97858. I have al...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Madison 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...
  • Swinging Couple in Madison, New to the LifestyleSwinging Couple in Madison, New to the Lifestyle Swinging Couple in Madison We are a swinging couple in Madison, Wisconsin. 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...