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!

Home / Alternative Sex Ads /

Show Ads In: Appleton / Oshkosh | Duluth / Superior | Eau Claire | Green Bay | Janesville | Kenosha-Racine | La Crosse | Madison | Milwaukee | Sheboygan | Wausau

December 5th, 2025

New 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...

Mistress has opening for a male submissive training in Madison area Mistress Seeks submissive male in Madison Mistress seeks submissive male for training in Madison. 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...

Kinky 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...

27 y/o Sexy Hung Crossdresser in Madison Hung Crossdresser for Male in Madison 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 ...

Passionate Swingers Seeking Playmates in Madison Hey there, I'm Winne from Madison, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly swingers looking to spice things up in the bedroom. We love exploring new fantasies and indulging in our wildest desires. You can find us on FreeSexAds.com Swingers Lifestyle Profiles und...

Passion Seekers in Madison, WI Hello there, I'm Helli from Madison, Wisconsin, and my husband and I are on the hunt for some steamy adventures with like-minded individuals. We're a fun-loving couple who are open-minded, kink-friendly, and always up for trying new things in the bedroom. If you're looking to add some spice to y...

Interviewing for new submissive for evenings and/or weekends Domme Woman for sub male in Madison 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...

Raunchy 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...

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...

Explore Your Desires with Davin from Madison! Hey there! My name is Davin, and I've got a unique fetish that I can't wait to share with you. Let's dive right in! I'm all about the world of submission, and being a submissive guy has its perks. There's something thrilling about giving up control and letting a Dominant woman take charge. It's l...

MISTRESS 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......

Sexy Transgender Beauty Looking for Love in Madison Hey there! I'm Katrina, a fun-loving transgender woman from Madison, Wisconsin. I may not fit society's idea of "normal," but that's what makes me unique and fabulous! 🌈 I love exploring my city and checking out local spots like the Memorial Union Terrace or Olbrich Botanical Gardens. Let's gr...

Tempting Temptress Seeks Submissive Souls Hey there, Madison! It's your friendly neighborhood fetish enthusiast, Sacha. 👋 I'm here to tell you about my oh-so-unique and tantalizing fetish. Brace yourself for an adventure like no other! Now, let me start by saying that I'm a lady who loves to explore the wild side of life. 🌟 I'm ope...

Join Jeanine for an unforgettable swinging experience in Madison! Hey there! My name is Jeanine 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 in creating a safe and exciting environment for everyone involved. You can find us in the swinger...

Unleash Your Desires with Kendal Hey there, Madison! It's Kendal, your friendly neighborhood fetish enthusiast. I wanted to share something exciting with you - my unique passion that sets my heart racing and ignites my imagination. Brace yourself for an adventure into the world of submission! You see, I've discovered an incredib...

Femdom Mistress Olivia in Madison, Wisconsin "Are you ready to submit to me and explore your deepest desires?" Domina Olivia here, ready to take control and dominate you in ways you've only dreamed of. From strap-ons and pegging to whippings and spankings, I will push your limits and bring you to your knees. Let me guide you through the wor...

Femdom Mistress Roxi in Madison I never settle for anything less than complete submission. Are you ready to bow down before me, Dominatrix Roxi? I am an experienced Femdom who knows exactly how to push your boundaries and fulfill your deepest desires. From strap-ons and pegging to whippings and spankings, I will take you on a j...

Local Shemale Looking for Hot Fun in Madison Hey sexy, I'm Michele and I'm a naughty shemale looking for a man who can handle all of me. I love to be on top, bottom, give blowjobs, get my ass played with, suck a big cock, ride until we both cum hard, and so much more. Let's explore our wildest fantasies together! You can find me in the FreeSex...

Looking for a Submissive Partner to Explore My Intriguing Fetish! Hey there, Madison! It's your friendly and open-minded girl, Maryjane, writing to you from the heart of Wisconsin. I wanted to share something unique about myself that I absolutely adore - my fetish. Now, before we dive in, let me tell you that I'm all about exploring other kinks and fetishes too....

Spark My Flame 🔥 Hey there, I'm Mandy from Madison, Wisconsin. I'm a curvy, Latina transgender woman who loves embracing my true self and being part of the LGBTQ community. I enjoy exploring new places in Madison like the Olbrich Botanical Gardens or grabbing a cup of coffee at Colectivo Coffee. If you're up for s...

Kinky Fetish Seeker in Madison! I've always had a wild side when it comes to exploring different kinks and fetishes. My name is Lani, and I'm from Madison, Wisconsin. I love the thrill of trying new things and pushing boundaries in the bedroom. Whether it's BDSM, domination, submission, roleplay, or age play, I'm always up for ...

Eclectic Transgender Beauty Looking for Love in Madison Hey there, I'm Yevette from Madison, Wisconsin. I'm a curvy Latina beauty who loves exploring my LGBTQ identity. I embrace my uniqueness and am looking for someone who appreciates it too. I enjoy long walks by Lake Monona, trying out new dishes at Graze, and catching live music at the High Noon ...

Passionate Swingers Looking for Playmates in Madison Hey there, I'm Melania from Madison, Wisconsin. My husband and I are fun-loving, open-minded, and kink friendly. We're always up for exploring new experiences and meeting like-minded individuals who share our passion for the swinging lifestyle. You can find us on FreeSexAds.com Swingers Lifestyle ...

Raunchy 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...

Submissive Male Seeks Dominatrix for Kinky Harvard Fetish I'm Harvard, a submissive male from Madison, Wisconsin looking for a Dominant Female Mistress or Dominatrix to take control and force me into submission. I want to learn how to properly please a Mistress and explore all kinds of kinky fetishes and roleplay scenarios. I enjoy whippings, spankings...

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...

Unleash Your Desires with Conan from Madison, Wisconsin! Hey there! My name is Conan and I've got a secret to share. I have this amazing fetish that makes me feel alive and adventurous! It's like an exhilarating rollercoaster ride for my senses. Curious to know what it is? Well, let me tell you! I am absolutely fascinated by the world of submission. Th...

Mistress Leila, Mature Mistress for sub in Madison Mistress Leila Madison 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...

Sparkle with Nicolina: Seeking Connection in Madison Hey there! I'm Nicolina, a proud transgender woman from Madison, Wisconsin. I may not fit society's norms, but I embrace my uniqueness and love spreading positivity wherever I go. 🌈 I enjoy the freedom of expressing my true self and being part of the LGBTQ community. It's empowering to live au...

Kinky Fetish Fun in Madison, Wisconsin Hey there! My name is Adella and I'm a kinky fetish lover from Madison, Wisconsin. I have a passion for exploring all things taboo and pushing boundaries. You can find me on FreeSexAds.com Alt profiles under username adellamad82583. I enjoy indulging in BDSM play, especially as a Dominatrix. Whippi...

Sensual Transgender Beauty Looking for Love in Madison Hey there! I'm Nance, a transgender woman from Madison, Wisconsin. I may not fit society's idea of "normal," but that's what makes me unique and special. I love embracing my true self and being part of the LGBTQ community. I'm looking for someone who can appreciate me for who I am, inside and out...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I've always been drawn to the world of submission, and my name is Bo. I'm a submissive male from Madison, Wisconsin, looking for a Dominant Female Mistress or Dominatrix to force me into submission and teach me how to properly please a Mistress. I can be found in the Alt profiles under username b...

Explore Your Wildest Desires with Minna from Madison Hey there! I'm Minna, a friendly and open-minded gal from Madison, Wisconsin. I have a unique fetish that I absolutely adore - I love exploring the world of Femdom. There's something so empowering about taking control and dominating a submissive male. It's thrilling to see them surrender to my eve...

December 4th, 2025

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Milt, a submissive male from Madison, Wisconsin, looking for 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 FreeSexAds.com Alt profiles under username milt21689. I have always been drawn to the world ...

Explore the Depths of Pleasure with Vale Hey there, folks of Madison! My name is Vale, and I'm here to share something unique about myself. Brace yourselves, because I have a fetish that's sure to ignite your curiosity. Picture this: a world where pleasure knows no bounds, where desires are embraced without judgment. That's what my fet...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I am Clancy, a submissive male from Madison, Wisconsin, looking for a Dominant Female Mistress to take control and show me the ways of submission. I can be found on FreeSexAds.com Alt profiles under username clancym12613. I crave being forced into submission, experiencing whippings, domination, and...

Raunchy Shemale Seeking Local Man for Wild Fun I love to play rough and dirty with a man who can handle my insatiable appetite for pleasure. My name is Marilin, a sexy shemale from Madison, Wisconsin, looking for someone who can keep up with me in the bedroom. I can be your naughty little secret, fulfilling all your wildest fantasies. You can ...

Sparkle with Lizabeth: Seeking Connection in Madison Hey there, I'm Lizabeth from Madison, Wisconsin. I'm a curvy, Latina transgender woman who loves exploring the LGBTQ community and embracing my true self. I find joy in connecting with others who appreciate authenticity and diversity. I enjoy spending time at local spots like the Chazen Museum of...

Kinky Fetish Seeker in Madison, WI I'm Sofie, and I have a wild side that craves exploration. I love all things kinky and am always looking for new experiences to satisfy my desires. Whether it's BDSM, domination, submission, roleplay, or anything in between, I'm up for it all. I enjoy whippings, spankings, and age play. The fee...

Elegantly Transcendent Seeking Connection Hey there! I'm Dawna, a transgender woman from Madison, Wisconsin. I may not fit society's norms, but I embrace my unique self with confidence and pride. Being part of the LGBTQ community has brought so much joy and acceptance into my life. I love exploring local spots like the Olbrich Botanical...

Explore Your Wildest Desires with Jo from Madison Hey there, I'm Jo from Madison, Wisconsin and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom and taking control in the bedroom. It's exhilarating to see a submissive male worship at my feet and fulfill my every desire. I may be friendly and open-minded, but ...

Explore Your Wildest Desires with Ellie from Madison Hey there, I'm Ellie from Madison, Wisconsin! I have a unique fetish that I absolutely adore. It's all about feet - the shape, the smell, the feel. There's something so intriguing and exciting about exploring this kink. I'm a friendly and open-minded person who loves to dive into different fetish...

Explore Your Wildest Desires with Jammie from Madison Hey there! My name is Jammie and I have a unique fetish that I absolutely love exploring. I am friendly, open-minded, and always up for trying new things. My fetish involves wearing latex clothing and indulging in some playful domination. I find it incredibly empowering and thrilling to take contr...

HMU for Sex in Madison Newly Single and Ready to Mingle in Madison 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 Madison, Wisconsin area then message me @BarbieSingle28.      ...

Submissive 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...

Spark Up Some Chemistry with Lissa Hey there! I'm Lissa, a transgender cutie from Madison, Wisconsin. I may not fit into society's narrow idea of beauty, but my confidence and charm are off the charts. You can check out my pics at my personal profile page @lissama48869. I love being part of the LGBTQ community because it allows me...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I'm Zack, a submissive male from Madison, Wisconsin, looking for a Dominant Female Mistress to take control and force me into submission. I want to learn how to properly please a Mistress and explore all kinds of kinky fetishes and fantasies together. I enjoy being spanked, roleplaying scenarios...

Raunchy 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 ...

Unleash Your Wildest Desires with Alena from Madison Hey there, fellow pleasure-seekers! I'm Alena, a vivacious female swinger hailing from the vibrant city of Madison, Wisconsin. If you're ready to embark on an unforgettable journey into the realm of passion and exploration, then look no further! Together with my equally open-minded husband, we're...

Passionate Swingers Looking for Playmates in Madison Hey there, I'm Adrianne from Madison, Wisconsin. My husband and I are a fun-loving, open-minded couple who love exploring our kinks and fantasies with like-minded individuals. We're always up for new adventures and are looking to spice things up in the bedroom with some sexy playmates. You ca...