Winnipeg Transgender Sex Ads

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Show Ads In: Winnipeg | Brandon

October 3rd, 2025

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...

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...

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...

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...

Raunchy Shemale Seeking Local Man for Wild Encounters Are you ready to explore your deepest desires with a sexy shemale named Carlynne? I'm looking for a man in Winnipeg, Manitoba who can handle all the naughty fun I have in store. From passionate kissing to mind-blowing blowjobs, I love it all. Let's play together and make each other cum over and over...

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...

SHEMALE HOOKUPS! Wanna Have a Great Time in Winnipeg, Manitoba? HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS!  Shemale Profiles Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up! Join free for Instant Access to the Winn...

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.&...

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...

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...

Raunchy Shemale Seeking Local Man for Wild Fun Are you ready to experience the ultimate pleasure with a hot shemale like me, Harriett? I'm looking for a man in Winnipeg, Manitoba 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 ecstasy. From top to bottom, I k...

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...

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...

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...

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...

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!...

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...

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...

October 2nd, 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...

Spark the Flame: Seeking Connection in Winnipeg Hey there, I'm Marja, a proud transgender woman from Winnipeg, Manitoba. I may not fit society's mold of what a woman should look like, but my unique journey has given me a deep appreciation for authenticity and self-love. Being part of the LGBTQ community has allowed me to embrace my true self an...

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...

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...

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 ...

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...

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...

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 ...

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...

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 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...

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...

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...

Elegantly Transformed: Seeking Connection in Winnipeg Hey there, I'm Kassey from Winnipeg, Manitoba! I'm a curvy transgender woman who loves embracing my true self and connecting with others in the LGBTQ community. Whether it's exploring The Forks for a romantic stroll, grabbing a coffee at Little Sister Coffee Maker, or enjoying a night out at Club ...

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...

Seeking Local Man for Raunchy Shemale Fun in Winnipeg Are you looking for a hot shemale to fulfill all your wildest fantasies? Look no further, because I'm Else and I'm ready to show you a good time. I'm a horny shemale seeking a local man for some steamy encounters that will leave you begging for more. I love getting down and dirty, so if you're in...

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...

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...

Looking for Love and Adventure in Winnipeg! Hey there, fellow Winnipeggers! My name is Madel, and I'm excited to put myself out there in the dating world. As a transgender person, I've learned so much about self-acceptance and embracing my true identity. Being part of the LGBTQ community has brought me closer to amazing individuals who shar...

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, 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...

October 1st, 2025

Hot Shemale Issie Ready to Play in Winnipeg Hey sexy guys, I'm Issie, a naughty shemale looking for a local man who can handle all of my desires. I love getting down and dirty, exploring every inch of your body with my eager lips and tight ass.When we meet up, I want to give you the best blowjob of your life. I'll deepthroat your throbbing co...

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 ...

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...

Hot Shemale in Winnipeg Looking for a Wild Time I'm Josey, a sexy shemale in Winnipeg looking for a local man who can handle all my desires. I love to get down and dirty, exploring every inch of your body with my throbbing cock. Whether you're into blowjobs, anal play, or just some good old-fashioned fucking, I'm your girl. I want to gag on y...

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...

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...

Looking for Love and Adventure! Hey there, lovely people of Winnipeg! My name is Mariellen, and I'm a proud transgender woman who's ready to embrace life and find someone special to share it with. 💕 So, let me tell you a bit about myself. I have a curvy body that loves dancing to the beat of my favorite tunes. 🎵 With my r...

Transgender Beauty Looking for Love in Winnipeg Hey there, I'm Karolina, a fun-loving transgender woman living in Winnipeg, Manitoba. I may not be your typical girl next door, but that's what makes me unique! I embrace my trans identity and love being part of the LGBTQ community. I enjoy exploring the local art scene at the Winnipeg Art Galle...

Embrace Your True Self with Alyda Hey there! I'm Alyda, a transgender woman from Winnipeg, Manitoba. 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. It's all about authenticity and self-love, right? 😊 I'm looking for som...