Winnipeg, Manitoba Shemale Dating Classifieds

Winnipeg, Manitoba shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

Home / Shemale Dating /

Show Ads In: Winnipeg | Brandon

December 18th, 2025

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

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...

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...

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...

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...

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...

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'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...

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...

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 ...

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...

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...

British T-girl Seeking Classy Gentleman in Winnipeg... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Winnipeg and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excep...

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...

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...

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...

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...

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...

December 17th, 2025

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...

🍫 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...

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...

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!...

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...

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 ...

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,...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Winnipeg boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'm se...

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 ...

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....

TS m/f switch 28 new here TS m/f Switch in Winnipeg Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...

I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...

Trans Playmate Sex Kitten... Ebony trans woman in Winnipeg wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups. I am...

Seeking a Stunning TS for Passion & Pleasure 😘🔥  I am a confident, strong and open minded man, who knows what I want from a woman  – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to  explore and enjoy every second of it, whether it is a casual hookup, a fun date or a  deep connect...

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...

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...

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....

TS Latina Bombshell Craving a Real Man to Handle Her 🍑🔥  Hola, papi 😘 You are my TS Latina fantasy because I carry your weight in all  the right places and your softness in all the other places and my body is made for late nights  and louder moans. My skin is golden, my tongue is bilingual, and my hips don’t  lie... especiall...

Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the W...

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...

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...

She-male looking for hot date to please. Asian Shemale in the Winnipeg Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them come...

💦 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 ...

Email Local Shemales Now! 💌 Want to Hookup and Find Local Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you'reinterested in 😉.. Do you want to meet local shemales who want to fuck and have some sex...

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...

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...

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...

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 ...

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 ...

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...