Winnipeg, Manitoba Shemale Dating Classifieds

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Show Ads In: Winnipeg | Brandon

October 18th, 2025

Shemale 4 Men 🍆💦 Winnipeg Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy It😉   View My Private Pictures -  If you’re looking  to mess around… I don’t know, maybe in a way that’s a bit spicy for the  two of us? I’m a trans beauty with a dirty mind and I love...

I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Winnipeg I'm queen Delilah a trans woman here in Winnipeg searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous positi...

Hot trans chick with nice boobs Hot trans chick in Winnipeg. Sheila wants to meet you. Hey all, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, top or bottom, love oral sex. Want to explore kinks? Me too!! Want to meet me? Send me a message @HotTransChick...

Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  WinnipegShemale Seeking Man for sex💦 View More of My Pix - ✅ Some nights are for breaking rules, for letting go, and  for indulging in pure pleasure.  I am a trans goddess with a wild side, and I  am looking for a man who wants to play. We sh...

Winnipeg Addicted to shemales... Male Seeking TS  A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible  moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you  are looking for a casual meet or if we can make this a more regular thing, I ...

Let’s Play a Game—Winner Gets Me 😉 Winnipeg Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...

October 17th, 2025

HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Winnipeg! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Winnipeg!  No strings - just great times, so join my page free for instant access! Shemale Gia's Winnipeg Sexbook @ShemaleGia27 Photos: 42 ...

Erotic exotic Asian queen in Winnipeg now (25) Asian Transexual in Winnipeg Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....

Seeking All TS Beauties in Winnipeg  I am a masculine, dominant, and very passionate man, and I am looking for a sensual  and seductive TS woman to explore our deepest desires together. No matter whether you like to be the  boss or to be taken care of, I am all about creating electric chemistry and unforgettable moments...

Penny for your thoughts? Penny TS in Winnipeg Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online!! I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting hit...

MALE SEEKING SHEMALE 🍆Winnipeg Ready to Play and Fuck 💦 I have a secret.. 🤫 I've always want to see what it's like to play with a shemale!!  Hi I'm John, I'm in Winnipeg  and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a good heart a...

💦 Thick, Juicy & Kinky – Come Experience the Best 😏  🔥| Do you feel that you want something new and exciting and that you want to  remember for a long time? I am a hot, all natural ebony TS with all the right amount  of curves and a naughty and adventurous spirit. I don’t just know how to tease, please and  make you want ...

Looking for a TS Woman Who Loves to Be Desired 💦🔥 Winnipeg  Male Seeking Transsexual for fun and whatever else!! I am a charming, confident and masculine guy and I have a special interest in beautiful TS  women. I would be happy to meet anyone who wants to have fun, enjoy and indulge in the  process. 💋 I would love to meet a shemale or tra...

I Need a Sexy Man to Tame Wild Willy! Hung Winnipeg Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Winnipeg with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see ...

INTERACTIVE MAP: Transexual Tracker in the Winnipeg Area! Local Transexual Hookups Meet local transexuals in the Winnipeg area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Winnipeg Trans Hookups Map ...

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...

Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too. See my pictures and send message for date....

BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK 🍆😉 BBC SHEMALE - BLACK TRANS💎 let's play with each others cocks! Hey there boo thang, I know you're going to like what you see. Shiit, I have something for you baby. I love being feminine and sexy. I do still have my penis and I love to use it. I want to see your mouth on it infact.. Would you...

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Winnipeg  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures 📸 Are you the sort of man who enjoys  just a touch of danger, a touch of excitement, and a lot of passion? I’m the  trans beauty you’ve been dreaming of — sexy...

Email Winnipeg Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...

TS Latina Dream Girl – Ride Me Like a Telenovela 😈📺  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Winnipeg Secret Crossdressing Hookups in Winnipeg Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a private ga...

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Winnipeg ) Sexy Crossdresser Elissa Looking for Hot Fun in Winnipeg💋    Do you like knowing I'm a man in womens clothes.. do I look sexy??    - VEW MY CD PICTURES Are you wanting to satisfy your innermost desires with a sexy shemale such  as myself? My name is Elissa and I am a ...

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...

TS Beauties—Let’s Have Some REAL Fun! 😏🔥  I am a tall, fit, and successful man and I have a taste for gorgeous TS women  who love to be adored, desired and pleasured. Whether you are looking for a wild  night, a passionate escape or something ongoing, I know how to treat a woman right. 💋 Must  have confidence, charm...

TS Latina Fantasy Girl – Let Me Rock Your World 💋🔥  Mira, papi… I’m not just sexy — I’m dangerous 😘 ( View My Dating Pictures Here ) My  TS Latina body features silky skin and long hair and full lips and a tight and juicy physique. I  dress to kill. My moans produce musical sounds. My movements flow throug...

Having fun and Staying Young Young trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile and message me xoxo, Sherry....

I'm the Girl Mother Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Winnipeg for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man who lives n...

Shy Transexual Escort in Winnipeg Shy transexual Camille here to tease you with my long functioning lady stick. Age 24, slim, healthy and physically fit. I love sex! I do top or bottom, special attention to your needs. Kink friendly so let me know what you like. I love it all. Explore your passion for trans women discreetly with an ...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Winnipeg who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it'...

Flawlessly gorgeous trans bombshell in Winnipeg Trans MtF for Man in Winnipeg I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send your ...

🍑 Your Secret Ebony Fantasy Is Just One Message Away 😜  👄 I am going to make your wildest dreams come true. I am a classy  yet freaky ebony trans beauty that loves to explore deep desires and steamy fantasies. If you are  a man that appreciates soft skin, full lips and a body made for pleasure then we need to  talk. If you are loo...

Looking for My TS Queen 👑💋 I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. 💕 I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...

One Night, No Rules, Just Pleasure… Winnipeg I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🤫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktails....

Sexy hung and big busted Hung and Busty Shemale in Winnipeg Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....

Spicy 🌶 Latina Shemale in Winnipeg Ready to Fill You 😉😉 LATINA SHEMALE SEEKING 🔥🌶  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Winnipeg.  Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woman who loves ...

M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....

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...

Flirty & Feminine CD Ready for Some Fun 💕😈  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  💋 💎 Bath g...

🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 💖 Hey, Handsome! I’m a sultry, curvy ebony TS  here in Winnipeg... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! 😘 I'm writing this to...

Marina TS 🍆 Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...

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...

Sassy CD Looking for a Real Man 😘🔥  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...

Ebony Shemale in Winnipeg ❤️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies 💋 Are you looking for a hot and kinky black shemale in Winnipeg? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale..  I am a stunning transgender woman who loves to pl...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Winnipeg Area Hi, my fem name is Gloria. I'm a married crossdresser in the Winnipeg area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing ...

Flirty, Dirty, and Ready for Some Fun ❤️ Winnipeg Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...

👄 Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  👑 I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...

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...

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.&...

Your Flirty CD Sweetheart Awaits 💕😘 Winnipeg I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. 💋 👠 Feminine, fun and ...