Winnipeg Transgender Sex Ads

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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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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 ...

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...

New Body New Me M2F post-op in Winnipeg 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 Natash...

Transgender Beauty Looking for Love in Winnipeg! Hey there, lovely people of Winnipeg! My name is Gabriela, and I'm a proud transgender woman ready to find that special someone who appreciates me for who I am. 💕 I may have a curvy body that'll make you weak in the knees, but it's what's on the inside that truly counts. As a member of the LGB...

August 16th, 2025

Hot Shemale Debby Looking for Wild Fun Are you ready to experience the ultimate pleasure with a sexy shemale like me, Debby? I'm a naughty tranny who loves to play dirty and fulfill all your wildest fantasies. From top to bottom, I know how to please a man in every way possible. I enjoy everything from giving sloppy blowjobs to gettin...

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

Well Endowed Shemale for Man in Winnipeg Hung Shemale for Man in Winnipeg I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncens...

Sexy Shemale Looking for Hot Fun in Winnipeg Hey there, I'm a naughty shemale named Hayley who's on the hunt for a local man to satisfy all my wildest desires. I love getting down and dirty, exploring every inch of your body and making you scream with pleasure. If you're into a kinky shemale who knows how to have a good time, then look no furt...

Elegantly Transcending Boundaries Hey there! I'm Paloma, a proud transgender woman from Winnipeg, Manitoba. I may not fit society's standards of beauty, but I embrace every part of myself with confidence and grace. Being part of the LGBTQ community has taught me the importance of self-love and acceptance, and I wouldn't have it an...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Winnipeg Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

Spark a Connection with Hanni Hey there! I'm Hanni, a fun-loving transgender cutie from Winnipeg, Manitoba. I may not fit society's mold, but that's what makes me unique and fabulous. Being part of the LGBTQ community has given me a sense of belonging and empowerment that I cherish every day. If you're looking for someone who ...

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...

TS M2F Top in Winnipeg TS Top Seeking Man in Winnipeg I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body.  Non op functional, nice big ladystick for your pleasure! 😈  Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kinks and...

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...

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...

Hot Shemale Nadia Looking for Wild Fun in Winnipeg Are you ready to experience the ultimate pleasure with a sexy shemale like me? My name is Nadia and I am a naughty tranny who loves to play dirty. I am on the hunt for a local man who can handle my insatiable desires and give me the satisfaction I crave. When it comes to sex, I am open-minded and...

Debonair Trans dude, looks like Bond F2M Trans Dude in Winnipeg Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relationship.&...

Sweet and Sensual Transgender Beauty Seeks Connection Hey there, I'm Cicily from Winnipeg, Manitoba. I'm a curvy Filipina trans woman who loves embracing my true self and connecting with others in the LGBTQ community. Whether we grab a coffee at Fools & Horses or take a stroll through The Forks, I'm all about creating meaningful connections and havin...

Raunchy Shemale Looking for Hot Fun in Winnipeg I'm a sexy shemale named Shari looking for a local man who can handle all my desires. When it comes to sex, I'm open-minded and love trying new things. From deepthroat blowjobs to rough anal play, I'm down for it all. I enjoy being both top and bottom, so let's explore every position together. My ...

Hot Shemale Anjela Looking for Local Man to Fuck and Suck Are you looking for a raunchy shemale who knows how to have a good time in the bedroom? Look no further because I'm Anjela, a sexy shemale from Winnipeg, Manitoba, seeking a local man for some wild fun. I love getting down and dirty with a man who can handle my huge throbbing cock. I enjoy being...

Spicy Hot 🌶 Tranny Girl from Colombia Latina Tranny Girl in Winnipeg Hey guys, I am Gabriella and I am looking for a longterm relationship with a gentleman who love sex as much as I do! I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery except breasts. I am smooth and clean, very feminin...

Transgender Temptation in Winnipeg Hey there, I'm Ellene from Winnipeg, Manitoba. I'm a curvy, Filipino transgender woman who loves embracing my true self and being part of the LGBTQ community. If you're looking for someone who is confident, fun-loving, and open-minded, then look no further! I enjoy exploring local spots like The ...

Sexy Shemale in Winnipeg Looking for Hot Fun Are you ready to explore your wildest fantasies with a sexy shemale? Look no further, because I'm here to make all your dreams come true. My name is Tierney and I'm a naughty tranny looking for a local man who can handle all of me. I love getting down and dirty, so if you're into some raunchy fun...

Explore Love and Adventure with Zena Hey there, I'm Zena, a fun-loving transgender gal from Winnipeg, Manitoba. I love exploring new places in the city like The Forks or Assiniboine Park. Let's grab a coffee at Fools & Horses or go for a stroll along the river at St. Vital Park. I enjoy being part of the LGBTQ community because it a...

Sexy Shemale Vivian Looking for Hot Fun in Winnipeg Are you ready for a wild time with a naughty shemale like me? My name is Vivian and I am seeking a local man in Winnipeg who can handle all my dirty desires. I love to play both top and bottom, giving and receiving pleasure in every way possible. From blowjobs to anal play, I am up for anything th...

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August 15th, 2025

Spark up some Winnipeg Magic with Bev! Hey there, I'm Bev, a fun-loving transgender babe from Winnipeg, Manitoba. I may not fit society's norms, but that's what makes me unique and fabulous! I love embracing my true self and being a part of the LGBTQ community. It's all about love and acceptance, right? 😊 I'm looking for someone wh...

Hot Shemale in Winnipeg Looking for a Wild Time Are you ready to have the time of your life with a sexy shemale like me? My name is Selina and I am on the hunt for a local man who can handle all of my naughty desires. I love getting down and dirty, exploring every inch of your body and making you scream with pleasure. From top to bottom, I know...

Hot Shemale in Winnipeg Looking for a Wild Time Are you ready to have some naughty fun with a sexy shemale named Silva? I'm on the hunt for a local man who can handle all of my desires and fantasies. When it comes to sex, I love it all - from giving blowjobs to getting my tight ass pounded. I'm a top, bottom, and everything in between. I enjoy ...

Looking for Love in All the Right Places Hey there! My name is Lorne, and I'm a transgender individual from Winnipeg, Manitoba. 🌈 I wanted to put myself out there and see if I can find someone special who appreciates me for who I am. So, here's a little bit about me: Physically, I have a curvy body type that matches my vibrant person...

Naughty Shemale Kia Seeking Local Man for Wild Fun! Looking for a hot man in Winnipeg who can handle a wild shemale like me, Kia. I love getting down and dirty, so if you're into some raunchy fun, I'm your girl... err, shemale! I enjoy being both a top and a bottom, giving blowjobs, getting my ass pounded, sucking cock, and making sure we both have...

Exploring Love and Adventure - Transgender Dating with Elvera Hey there! 👋 My name is Elvera, and I'm on the lookout for someone special to share some amazing experiences with. As a transgender individual, I embrace my unique journey and celebrate being part of the LGBTQ community. 🌈 Physically, I have a body that's curvy in all the right places, maki...

Hot Shemale Dani Seeking Local Man for Wild Fun Are you looking for a sexy shemale to fulfill all your wildest fantasies? Look no further, because I'm here to satisfy all your desires. My name is Dani and I am a naughty shemale from Winnipeg, Manitoba, seeking a local man for some mind-blowing sex and fun. I love getting down and dirty with a ...

Looking for Love in All the Right Places Hey there, lovely people of Winnipeg! My name is Winona and I'm putting myself out there in the big wide world of dating. 🌍✨ Being transgender has taught me so much about love, acceptance, and embracing who I truly am. 🌈❤️ I may not fit into society's cookie-cutter mold, but that's wh...

Looking for Love and Adventure! Hey there! My name is Dorthy, and I'm a transgender woman living in the beautiful city of Winnipeg, Manitoba. 🌸 So, let me tell you a bit about myself. I have a unique body type that's curvy in all the right places, making me feel confident and comfortable in my own skin. 💃 As for my ethnic...

Euphoric Trans Beauty Seeking Connection in Winnipeg Hey there, I'm Dorie from Winnipeg, Manitoba. I'm a proud transgender woman with a bubbly personality and a passion for life. I love being part of the LGBTQ community and embracing my true self every day. If you're looking for someone who is genuine, caring, and loves to laugh, then look no further!...

Raunchy Shemale Seeking Local Man for Hot Encounters Are you looking for a wild time with a sexy shemale in Winnipeg? Well, look no further because I'm here to fulfill all your dirty desires. My name is Cassie and I'm a top shemale who loves to dominate in the bedroom. I enjoy giving sloppy blowjobs, getting my tight ass pounded, and making you cum...