Windsor, Ontario Alternative Sex Ads - BDSM, Trans & Swingers

Browse Windsor, Ontario 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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November 11th, 2025

FtM seeking Princess Bride in Windsor FtM seeking Woman in Windsor Hi, I'm Andy, age 33, FtM transgender man living in Windsor. 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...

New Body New Me M2F post-op in Windsor 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...

Passionate Swingers Looking for Playmates Hey there, I'm Adrianne from Windsor, Ontario, and my husband and I are on the hunt for some new friends to join us in our wild adventures. We're a fun-loving couple who are open-minded and kink friendly. We love exploring our sexuality and pushing boundaries in the bedroom. Whether it's wife sw...

Looking for Love and Adventure in Windsor!
Hey there, lovely people of Windsor! My name is Yolanda, and I'm on the lookout for that special someone who's up for some fun, laughter, and maybe even a little bit of romance. 😊 As a proud transgender woman from Windsor, Ontario, I embrace my unique journey and everything that comes with bei...

Local Shemale Looking for Hot and Steamy Fun in Windsor! I'm a hot shemale named JoAnn seeking a local man in Windsor who can handle my insatiable appetite for all things naughty. I love getting down and dirty, exploring every inch of your body with my skilled hands and mouth. Whether you're into passionate kissing, deepthroating blowjobs, or intense an...

Explore Your Wildest Desires with Milly from Windsor Hey there! My name is Milly and I have a unique fetish that I absolutely love. I adore dressing up in leather and dominating my partner. The feeling of power and control is such a turn on for me. But don't worry, I'm also super friendly and open-minded. I love exploring new kinks and fetishes, so ...

Local Shemale Seeking Man for Raunchy Fun Are you ready to explore your wildest fantasies with a sexy shemale like me, Carmine? I'm looking for a local man who can handle all the naughty things I have in mind. When we meet up, get ready for some mind-blowing action. I love being both a top and bottom, so we can switch things up as much as...

Swinging Couple in Windsor, New to the Lifestyle Swinging Couple in Windsor We are a swinging couple in Windsor, Ontario. 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. ...

Danny's Kinky Fetish Adventures I'm Danny, a kinky girl from Windsor, Ontario who loves exploring all sorts of fetishes and kinks. I'm always up for trying new things and pushing boundaries in the bedroom. Whether you're into BDSM, domination, submission, roleplay, spankings, or even age play, I'm your girl! I love being a Mistr...

Want to Fuck My Wife? Let's Swap in Windsor Wife Swaps in Windsor Attractive, adventurous and athletic couple in the Windsor 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 ...

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

Passionate Windsor Swingers Looking for Playmates Hey there, I'm Gray from Windsor, Ontario. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We're always up for new adventures and love meeting new friends in the lifestyle. You can find us on FreeSexAds.com Swingers L...

Raunchy Shemale Seeking Local Man for Wild Fun Hey there, I'm Jewel, a hot and horny shemale from Windsor, Ontario looking for a man who can handle all of me. I love getting down and dirty, exploring all kinds of kinky fantasies. When it comes to sex, I'm open to just about anything - from deepthroating your cock to riding you until we both expl...

Seeking Kinky Fun in Windsor, Ontario! My name is Gracia and I am a fetish enthusiast looking for like-minded individuals to explore our wildest fantasies together. I can be found on FreeSexAds.com Alt profiles under username gracia45460. I have always had a passion for BDSM, particularly enjoying being a Dominatrix and exploring the...

Explore Your Wildest Desires with Luisa from Windsor Hey there! I'm Luisa, and I have a unique fetish that I absolutely adore. It's a little unconventional, but that's what makes it so exciting for me. I love the feeling of silk against my skin, the way it glides and caresses me in all the right places. It's like a luxurious indulgence that never fa...

A World of Pleasure Awaits with Jeremie Hey there, folks! It's your friendly neighbor from Windsor, Ontario, Jeremie here. I've got a unique fetish that I can't wait to share with you. Now, before I spill the beans, let me tell you a little bit about myself. First things first, I'm a submissive guy who loves exploring new kinks and fet...

Join Kathleen for a Wild Ride in Windsor Hey there, I'm Kathleen from Windsor, Ontario. My husband and I are friendly, open-minded, and 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 adventure. You can find us in the swingers dating pro...

Passion Seekers Looking for Playmates in Windsor Hello there, I'm Suzie from Windsor, Ontario. My husband and I are fun-loving, open-minded, and kink friendly swingers who are always up for a good time. We love exploring our desires and sharing our passion with like-minded individuals who are looking to spice things up in the bedroom. You can f...

Explore Your Wildest Fantasies with Jewell from Windsor Hello there! My name is Jewell and I am a female swinger from Windsor, Ontario. 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 respectful environment for everyone involved. If you are looking to spice u...

Kinky Mistress Seeking Submissives for BDSM Fun I'm Mariel, a dominant woman from Windsor, Ontario who loves exploring all kinds of kinks and fetishes. If you're looking to submit to a powerful Mistress who knows how to take control, then I'm the one for you. I enjoy whippings, domination, roleplay, and much more. Whether you're into spankin...

Join Harlie for a Sensual Adventure Hello there! My name is Harlie and I am a female swinger from Windsor, Ontario. 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 and creating unforgettable experiences together. You can find us in the swingers ...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Windsor Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27. I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naughty fan...

Domme looking for male sub who wants to be owned Domme for male sub in Windsor 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...

MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Windsor Dominatrix Message Me Online: MistressKim4subWindsor Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......

Raunchy Shemale Seeking Local Man for Wild Fun Hey there, I'm Kathie, a sexy shemale from Windsor looking for a man who can handle all my dirty desires. I love being both top and bottom, giving sloppy blowjobs, getting my tight ass pounded, and riding a throbbing cock until we both explode with pleasure. I enjoy playing with toys, exploring kink...

Unleash Your Desires with Karia from Windsor! Hey there, lovely people of Windsor! It's me, Karia, and I've got something exciting to share with you. Are you ready to dive into the world of fetishes? Well, buckle up because I've got a unique one that will blow your mind! I'm a friendly and open-minded woman who loves exploring different kink...

Unleash Your Desires with Trey Hey there, Windsor folks! It's your friendly neighbor, Trey, here to share something exciting with you. I've got a unique fetish that keeps me intrigued and oh-so-enchanted. Now, before I spill the beans, let me tell you a little about myself. I'm an open-minded guy who loves exploring new kinks ...

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

Submissive Male Seeks Dominatrix for Kinky BDSM Fun
I'm Mort, a submissive male from Windsor, Ontario, 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 mort74254. I enjoy being spanked 🍑, roleplay �...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun My name is Clarke and I am a submissive male from Windsor, Ontario. 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 clarkew95025. I have alwa...

Kinky Domina Seeking Submissive Men for BDSM Fun in Windsor Hello there, I am Emmalyn, a strict and dominant Mistress from Windsor who loves exploring all kinds of kinky fetishes and fantasies. Are you ready to submit to my every whim and desire? Do you crave the thrill of being under my control? Then look no further, because I am here to make all your sub...

Hot Shemale in Windsor Looking for Wild Fun Are you ready to experience the ultimate pleasure with a sexy shemale? Look no further, because I'm Fallon and I'm here to fulfill all your wildest fantasies. I'm a naughty shemale who loves to get down and dirty with a hot man like you. Let's explore each other's bodies and unleash our deepest de...

Gorgeous, Passable Trans in Windsor 😍 Gorgeous Passable Trans MtF for Man in Windsor 😍 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...

Passionate Swingers Seeking Playmates in Windsor Hello there, I'm Maryanna from Windsor, Ontario. 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 to the ex...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Windsor? 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...

Mistress seeks Windsor male sub for BDSM and training Mistress seeking male sub in Windsor 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...

Unleash Your Wildest Desires with Pammi from Windsor Hey there, naughty souls! It's Pammi here, ready to take you on an unforgettable journey through the realm of pleasure. Brace yourselves, because things are about to get steamy! My husband and I are not your average couple. We're adventurous, open-minded, and always up for exploring new kinks and...

Explore the Sensual World of Otto from Windsor, Ontario Hey there! My name is Otto and I've got a unique fetish that'll blow your mind. I may not be able to tell you what I look like, but trust me, my fetish will leave you wanting more! I'm a submissive guy who loves to spend time with a Dominant woman. There's something incredibly thrilling about giv...

Passionate Swingers Looking for Playmates Hello there, I'm Nelia from Windsor, Ontario. 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 all kinds of pleasures. You can find us on FreeSexAds.com Swingers Life...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Windsor 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...

Mistress Savannah in Windsor // Domme seeking new sub Strict Mistress for sub in Windsor 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...

Join Tamma for a Sensual Adventure Hello there! My name is Tamma and I am a female swinger from Windsor, Ontario. My husband and I are a friendly and open-minded couple who love to explore various kinks and fetishes. We believe in creating a safe and exciting space for like-minded individuals to come together and indulge in their d...

Passion Seekers in Windsor, Ontario Hey there, I'm Brande, a fun-loving and open-minded swinger from Windsor, Ontario. My husband and I are always looking for new adventures and exciting experiences in the lifestyle. We are kink friendly and love to explore our deepest desires with like-minded individuals. You can find us on FreeSe...

DOMME AVAILABLE for private Femdom and DISCIPLINE Experienced Dominatrix for Windsor Submissive Experienced Dominatrix seeks submissive, ready and willing to learn discipline from a loving but strict Mistress. Contact me @ WindsorDommeX if you are available and willing to serve my needs. Available For: Discipline  Corporal Punishment Ro...

Explore the Sensual World of Dyan - A Tempting Journey Awaits! 🌟 Hey there, Windsor! It's your friendly and open-minded girl, Dyan, ready to take you on an exciting adventure into a world of unique desires. Let me introduce you to my irresistible fetish that sets my heart racing with anticipation! Now, let me be clear - I'm not just any ordinary gal. I have a ...

Explore Your Wildest Desires with Casey from Windsor Hey there! I'm Casey, a friendly and open-minded gal from Windsor, Ontario. I have a unique fetish that I absolutely adore - I love dressing up in leather and dominating my partner as a Femdom. There's something so exhilarating about taking control and exploring power dynamics in the bedroom. I'm...

Elegant Transgender Beauty Seeking Connection in Windsor Hey there! I'm Kailey, a transgender woman from Windsor, Ontario. I may not fit society's idea of "normal," but that's what makes me unique and special. 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 is ...

Elegant Transgender Beauty Seeking Connection in Windsor Hey there, I'm Karisa from Windsor, Ontario! I'm a confident and outgoing transgender woman with a curvy body and a mix of Italian and Canadian heritage. I love exploring my identity as part of the LGBTQ community and embracing all the unique experiences that come with it. If you're looking for so...

INTERACTIVE MAP: Transexual Tracker in the Windsor Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Windsor 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...

Hot Shemale Valerye Ready to Play in Windsor Are you looking for a wild time with a sexy shemale? Look no further, because I'm here to fulfill all your fantasies. My name is Valerye and I'm a horny shemale from Windsor, Ontario seeking a local man for some steamy fun. I love getting down and dirty, so if you're into it, I'm game for some ho...