Winnipeg, Manitoba Shemale Dating Classifieds

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Show Ads In: Winnipeg | Brandon

September 20th, 2026

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 ...

A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Winnipeg area and are interested then drop me a line and introduce yourself. You can...

Sexy Shemale Winnipeg I know You Want to Play FEMININE AND SECURE SHEMALE  Hot and kinky shemale seeking a hot and fun guy who isn't scared of a beautiful and secure Trans Woman.. I'm located in Winnipeg; I am AlaneTS and  I am here to fulfill all your desires. If you are in the area or planning to be. and  looking for a hot and...

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 ...

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 ...

Spicy and Hot T-Girl from Colombia Latina T-Girl in Winnipeg Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...

YOUR EBONY SHEMALE - big boobs and a BIG COCK! Winnipeg Hot Hot Hot! Sinead, a black shemale in Winnipeg ready to make all of your  wildest fantasies come true! 💋🔥 My Pictures and Profile! -- You want to find a sexy ebony shemale in  Winnipegto fulfill all your dreams? Then stop searching because I am ready to make  all of your dre...

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....

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...

Superb Shemale in Winnipeg... T-Girl for NSA Encounters in Winnipeg When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Winnipeg. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck an...

September 19th, 2026

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...

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 ...

Tainted Love - Beyond Compare! Kinky Trans Woman in Winnipeg Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Winnipeg. What kind of kink? You'll have to contact me to find out. I'm open to all sorts of fetish play if you are. I need a hookup with an open minded man. The sort of man who appreciates wha...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Winnipeg View My Personal Pix - 🤫  A sexy Crossdresser from Winnipeg, here, and her name is  KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being  a Crossdressing Trans woman. If you like dirty games...

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...

TS Latina Seductress – Thick, Wet & Ready to Be Used 💋🍑  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...

Dr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Winnipeg area come see if you measure up! Click here for explicit photos. Look ...

TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession 😈🍑  Hola, mi amor 😘 The fiery, curvaceous TS Latina body I possess was  made for lust while my soul demands intense passionate nights. Your dream woman has arrived because I possess caramel  skin and thick thighs and long hair and soft lips and a throbbing surprise between my legs th...

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...

Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Winnipeg area and want to make some new friends! I am a masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...

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...

I’m a Sexy and Naughty T-Girl Here in Winnipeg. Winnipeg T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Winnipeg area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries and ...

Latina TS Playmate – Sweet Accent, Dirty Thoughts 💃💋  You want flavor? Spice? A woman who can dance for you, then ride you like she  owns you? That’s me, papi 😘 I’m a curvy, high-femme  TS Latina with a pretty face, wild hips, and a very naughty surprise underneath. View My Latina TS Pictures - I love to  tease, fl...

Hot Shemale in Winnipeg Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Winnipeg My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Winnipeg who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some like minded people and hav...

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...

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 ...

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 ...

Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Winnipeg tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...

!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Winnipeg Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Winnipeg to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat ...

Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...

💖 Discreet, Naughty & Waiting for a Man Who Can Handle Me  🔥 I’m an exotic ebony TS bombshell in Winnipeg with a love for steamy nights,  deep connections and uninhibited pleasure, keep it hot and wild and unforgettable! Whether you are looking for  an exciting adventure, a sensual night of passion or just something you’ve nev...

Don't Worry I Bite! Feisty redhead trans in Winnipeg full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control ...

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...

👄 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...

THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! 😉 My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...

I want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Winnipeg area. Click here and come see me anytime!...

💦 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 ...

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...

Well Endowed Shemale is beautiful Winnipeg 32 Well Endowed Shemale in Winnipeg I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me at BlancaShemale32 for my latest pictures and proof of my size!&nb...

I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Winnipeg and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message now.. L...

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...

🍑 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...

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...

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...

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...

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 ...

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 Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋  Hello sweetheart 😘 The TS Latina bombshell body type defines me through my soft lips and thick  thighs and my hidden surprise under red lace. Your pleasure stands as my life purpose because I want to  satisfy your desires and make your body experience intense pleasure through my s...

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