Winnipeg, Manitoba Alternative Sex Ads - BDSM, Trans & Swingers

Browse Winnipeg, Manitoba 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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Show Ads In: Winnipeg | Brandon

August 17th, 2025

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Winnipeg 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!&n...

INTERACTIVE MAP: Kink Tracker in the Winnipeg Area! Winnipeg Alt & Kink Hookups Meet locals to explore the alternative lifestyles scene in the Winnipeg 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 an...

Raunchy Shemale Marta Looking for Hot Fun in Winnipeg Hey boys, I'm Marta, a sexy shemale in Winnipeg looking for a local man who can handle all my dirty desires. I love being both top and bottom, giving sloppy blowjobs and getting my tight ass pounded hard. I want to play with your cock, ride you until we both cum, and gag on your throbbing dick. Let'...

Hot Shemale in Winnipeg Ready to Play and Fuck I'm a sexy shemale named Terri looking for a local man who can handle all my desires. I love being both a top and bottom, giving blowjobs, getting my ass pounded, sucking cock, and making you cum hard. I enjoy sloppy gagging sessions and riding your throbbing dick until we both reach explosive or...

Kinky Fetish Fun in Winnipeg, Manitoba My name is Roxana and I am a woman who loves to explore all things kinky and taboo. I have always had a wild side and I am looking for someone who can keep up with me. I enjoy BDSM, roleplay, domination, submission, and so much more. I love the feeling of being in control as a Dominatrix, but I...

Explore Your Wildest Desires with Allyn Hey there, I'm Allyn from Winnipeg, Manitoba! I have a unique fetish that drives me wild - I absolutely love incorporating food into my intimate moments. There's something so sensual and exciting about exploring different tastes and textures in the bedroom. I'm a friendly and open-minded person ...

Passion Seekers in Winnipeg Hello there, I'm Abbey, and my husband and I are fun-loving, open-minded, and kink friendly swingers from Winnipeg, Manitoba. We love to explore our sexuality and connect with like-minded individuals who share our passion for the swinging lifestyle. You can find us in the FreeSexAds.com Swingers L...

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

Experienced Femdom Mistress Chere in Winnipeg, Manitoba Are you ready to submit to a powerful and demanding Dominatrix? Look no further, for I am Mistress Chere, a skilled Femdom with a passion for exploring all things kinky and taboo. 🖤 I take pleasure in a wide range of fetishes, including strap-ons, pegging, whippings, spankings, crossdressing, ...

Explore Your Desires with Derrek Hey there, I'm Derrek from Winnipeg, Manitoba. I have a unique fetish that I absolutely love - I enjoy being tickled! It's such a fun and playful experience for me. I'm a submissive guy who would love to spend time with a Dominant woman who enjoys exploring this kink with me. I'm friendly, open-m...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Winnipeg 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 fa...

Explore the World of Ileana: A Tempting Journey into Fetish Delight Hey there, fellow kink enthusiasts of Winnipeg and beyond! I'm Ileana, your friendly and open-minded fetish explorer from beautiful Manitoba. Today, I want to introduce you to a unique world where desires and fantasies come alive – my world. Now, let me tell you a little secret: I have this int...

Unleash Your Desires with Martainn from Winnipeg Hey there! 👋 Are you ready to dive into the world of excitement and exploration? Look no further, because I'm here to introduce you to a fetish like no other! My name is Martainn, and I hail from the beautiful city of Winnipeg, Manitoba. Let me tell you about my unique passion – it's called...

Winnipeg Strap On Sex Hookups Winnipeg Strap On Dating Profiles Browse strap-on profiles of women and men who enjoy hot role reversals!   ...

Unleash Your Wildest Desires with Ursa from Winnipeg! Hey there, fellow adventurers! I'm Ursa, and together with my incredible hubby, we're here to make your wildest dreams come true. We're a friendly and open-minded couple hailing from the heart of Manitoba - Winnipeg! Allow me to introduce us properly. My husband, let's call him Jake (because why ...

Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Winnipeg Hi! I'm Brandi, new TS in the Winnipeg 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 pa...

Explore Your Wildest Desires with Arlie Hey there! My name is Arlie and I have a unique fetish that I absolutely love. I am from Winnipeg, Manitoba and I enjoy exploring all kinds of kinks and fetishes. I am friendly, open-minded, and always up for trying new things. My fetish involves Femdom, where I take control and dominate my partn...

A Sensual Journey: Seeking Connection in Winnipeg Hey there, I'm Delinda, a free-spirited transgender woman from Winnipeg, Manitoba. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and share my journey with others. I'm looking for someone who appreciates authenticity and enjoys deep conv...

Passionate Swingers Seeking Playmates in Winnipeg Hey there, I'm Celle, and my husband and I are on the lookout for some sexy playmates to join us in our wild adventures. We're a fun-loving couple from Winnipeg, Manitoba who are open-minded, kink-friendly, and always up for some naughty fun. 💋 You can find us on FreeSexAds.com Swingers Lifest...

Submissive Male Seeks Dominatrix for Kinky BDSM Fun I've always been a submissive male at heart, craving the touch of a strong Dominant Female Mistress to guide me into submission. My name is Stanton, and I'm from Winnipeg, Manitoba. I'm on the lookout for a powerful woman who can force me into my rightful place and teach me how to properly please ...

Gorgeous, Passable Trans in Winnipeg 😍 Gorgeous Passable Trans MtF for Man in Winnipeg 😍 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 k...

Passionate Swingers Looking for Playmates Hello there, I'm Julia from Winnipeg, Manitoba. My husband and I are fun-loving, open-minded, and kink friendly individuals who enjoy exploring the exciting world of swinging. We are always on the lookout for like-minded couples or singles to join us in our steamy adventures. You can find us on F...

Tantalizing Temptress Seeks Submissive Souls Hey there, I'm Sande from Winnipeg, Manitoba! I have a unique fetish that I absolutely adore - I love playing with food in the bedroom. There's something so sensual and naughty about using whipped cream, chocolate sauce, and strawberries to explore each other's bodies. I'm a friendly and open-min...

Submissive Male Seeks Dominatrix for Kinky Fetishes and BDSM I never knew how much I craved being a submissive male until I discovered the world of kinks and fetishes. My name is Kenyon, and I am from Winnipeg, Manitoba. I am on the hunt for a Dominant Female Mistress or Dominatrix who can force me into submission and show me how to properly please a Mistre...

Hot Shemale in Winnipeg Looking for Fun Are you looking for a wild time with a sexy shemale? Look no further, because I'm Cara and I'm ready to fulfill all your dirty fantasies. I'm seeking a local man who can handle my insatiable appetite for pleasure and fun. Whether you want me to be your top or bottom, I'm down for anything that get...

Explore Your Wildest Desires with Valerye Hey there, I'm Valerye from Winnipeg, Manitoba! I have a unique fetish that really gets me going. I love indulging in foot worship 🦶 and being adored from head to toe. There's something so sensual and intimate about it that just drives me wild. I'm a friendly and open-minded person who loves ...

MISTRESS KIM IS HERE TO DOMINATE YOU.... Seeking new worthy, generous submissive Mistress Kim Winnipeg Dominatrix Message Me Online: MistressKim4subWinnipeg Flogging...prostate...nipple play...force by... paddling...dress up play..humiliate... strap on...must obedience......

Mistress Savannah in Winnipeg // Domme seeking new sub Strict Mistress for sub in Winnipeg 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 punis...

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

Superior Massage by gorgeous T-Girl T-Girl for Dating in Winnipeg 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: GayleTG...

Sexy Shemale in Winnipeg Looking for Hot Fun I'm a horny shemale named Erinn looking for a local man who can handle my insatiable appetite for sex. I love getting down and dirty with a guy who knows how to please me in all the right ways. Whether you're into giving or receiving, I'm game for it all. I enjoy being both a top and bottom, so w...

Explore Your Wildest Desires with Lorraine from Winnipeg Hey there! I'm Lorraine, a friendly and open-minded woman from Winnipeg who loves to explore all kinds of kinks and fetishes. One of my favorite fetishes is feet worship. There's something so sensual and intimate about having my feet pampered and adored. I'm always up for trying new things and p...

A Night of Magic Awaits You Hey there, I'm Kacie from Winnipeg, Manitoba. I'm a curvy transgender woman who loves exploring the vibrant LGBTQ community in our city. Whether it's grabbing a coffee at Fools & Horses or dancing the night away at Club 200, I always have a great time embracing who I am with my fellow queer friend...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Winnipeg 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...

Sexy Shemale in Winnipeg Looking for Hot Fun Are you ready to have the time of your life with a horny shemale? I'm Lorita, and I'm on the hunt for a local man who can handle all of my desires. When it comes to sex, I love it all - from passionate kissing to rough anal play. I want to be your top or bottom, give you mind-blowing blowjobs, and...

Join Maggie for a Wild Ride in Winnipeg! Hey there, I'm Maggie from Winnipeg, Manitoba. 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 prof...

Male sub looking for Mistress in Winnipeg Male sub seeking Mistress in Winnipeg 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 co...

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

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

Passionate Swingers Couple Ready for Playtime in Winnipeg Hello there, I'm Kath from Winnipeg, Manitoba. My husband and I are a fun-loving, open-minded couple who enjoy exploring our kinks and fantasies with like-minded individuals. We are always up for new adventures and love to meet new people who share our passion for the swinging lifestyle. You can ...

Explore Your Wildest Desires with Rosetta Hey there! I'm Rosetta from Winnipeg, Manitoba, and I have a unique fetish that I absolutely adore. I love indulging in foot worship 🦶🏼 and finding someone who appreciates my cute little toes as much as I do. It's such a turn on for me! I'm a friendly and open-minded person who loves to exp...

Sexy Shemale in Winnipeg Looking for Hot Fun Are you ready to get down and dirty with a horny shemale like me? My name is Kaylee and I'm looking for a local man who can handle all of my naughty desires. I love being both a top and bottom, so you better be ready for some intense action. Whether you want me to give you a sloppy blowjob or rid...

Join Luanna for a Sensual Adventure in Winnipeg Hello there! My name is Luanna and I am a female swinger from Winnipeg, Manitoba. 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 passion for excitement and adventure. You can find us on swingers...

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

Join Andee for an Unforgettable Swinging Experience Hey there, I'm Andee from Winnipeg, Manitoba. 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 adventure. You can find us in the swingers ...

Explore Your Wildest Fantasies with Jenn from Winnipeg! Hey there, I'm Jenn, a fun-loving female swinger from Winnipeg, Manitoba. My husband and I are friendly, open-minded, and always up for exploring new kinks and fetishes. Whether you're a seasoned swinger or just curious about the lifestyle, we'd love to meet you! You can find us on swingers datin...

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

F/M seeking love and fun Female to Male Trans Man in Winnipeg 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 gr...

Janet's Kinky Desires I'm Janet, a kinky girl from Winnipeg, Manitoba looking for someone to explore my wildest fantasies with. I love all things BDSM, especially domination and submission. Whippings, spankings, and roleplay really get me going. But I'm also curious about trying out age play and crossdressing. If you...

Tantalizing Temptress Elyssa Hey there! I'm Elyssa from Winnipeg, Manitoba, and I have a unique fetish that I absolutely adore. I love exploring the world of Femdom - being in control and dominating a willing submissive is such a thrilling experience for me. I'm friendly, open-minded, and always up for trying new things. I ...