Winnipeg Transgender Classifieds

Browse Winnipeg transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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Show Ads In: Winnipeg | Brandon

  • April 9th, 2025
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!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  ...
  • Trans Playmate Sex Kitten...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...
  • April 8th, 2025
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Winnipeg Look no further honey, I'm Franny an Ebony trans woman here in Winnipeg to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it and they don't have t...
  • Well Endowed Shemale is beautiful Winnipeg 32Well 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...
  • Debonair Trans dude, looks like BondDebonair 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.&...
  • Transgender🟒TINA TSπŸ˜‰πŸ’‹ Transgender🟒TINA TSπŸ˜‰πŸ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina πŸ’‹ 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...
  • Crystal, 27 New to the areaCrystal, 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 ...
  • She-male looking for hot date to please. 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...
  • Having fun and Staying YoungHaving 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....
  • New Body New MeNew 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...
  • Erotic exotic Asian queen in Winnipeg now (25)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....
  • TS Asian lady ready for upscale action (28)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...
  • Flawlessly gorgeous trans bombshell in WinnipegFlawlessly 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 short and cute and I have bedroom eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send...
  • I want to be a whoreI 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!...
  • Hot trans chick with nice boobsHot 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...
  • II'm the Girl Your Mum 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...
  • 🍁 TS Treat in Winnipeg, Manitoba πŸ‡¨πŸ‡¦ – Prairie Heat with a Wild Side 😘🌾🍁 TS Treat in Winnipeg, Manitoba πŸ‡¨πŸ‡¦ – Prairie Heat with a Wild Side 😘🌾  Hey cutie πŸ’‹ As a confident trans girl from Winnipeg I will bring you hot unforgettable fun  during your cold nights. My name is 33 and I have a caramel complexion with juicy thighs and  a playful personality that understands when to behave and when not to behave 😈. View My Tran...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Winnipeg Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Winnipeg men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About me:...
  • M-F trans woman wants a dateM-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....
  • Elisabeth waiting to be your QueenElisabeth 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...
  • FtM seeking Princess Bride in WinnipegFtM 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...
  • Dr FreakinDr 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 ...
  • Brandi 27 tall slim hot trans chick fully functionalBrandi 27 tall slim hot trans chick fully functional 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 big functioning ladyclit for top or bottom. I love oral sex!! Kink friendly, have toys to explore all y...
  • Transgender Goddess for Late-Night Escapes & Filthy Fun πŸŒ™πŸ’‹Transgender Goddess for Late-Night Escapes & Filthy Fun πŸŒ™πŸ’‹  It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile - As  your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have  imagined. My secret between...
  • Tiffany Shelle - Your Winnipeg Tranny Girlfriend! πŸ’žTiffany Shelle - Your Winnipeg Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Winnipeg It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functioni...
  • Letha Aims to Fill YOU With Her Love Gun!!!Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Winnipeg and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertion...
  • April 7th, 2025
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Winnipeg? Hey, I am Jasmin, 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...
  • Do you know the difference between a dick and a bucket of popcorn?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...
  • Hi Guys!! 32 y/o Trans looking for someone fun!Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Winnipeg for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be p...
  • British T-girl Seeking Classy Gentleman in Winnipeg...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...
  • Partners in crime, or?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...
  • DonDon'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 ...
  • Email Winnipeg Shemales❀️‍πŸ”₯Email Winnipeg Shemales❀️‍πŸ”₯ 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...
  • Superb Shemale in Winnipeg...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...
  • Email Winnipeg Shemales Now! πŸ’ŒEmail Winnipeg Shemales Now! πŸ’Œ Want to Hookup and Find Winnipeg 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're interested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sexy fun? I da...
  • II'm a Horny Shemale πŸ˜ˆπŸ’‹ Looking For Sex Tonight!! Sexy ShemaleπŸ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App πŸ“² 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...
  • Strict Shemale Dominatrix in Winnipeg - @DesireeTransDommeStrict Shemale Dominatrix in Winnipeg - @DesireeTransDomme Powerful African-Queen Dominatrix in Winnipeg I am full-time professional Domme Desiree. My Winnipeg area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn ...
  • Twisted Sister - Loves to Ride.... and be Ridden!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...
  • Tainted Love - Beyond Compare!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...
  • Penny for your thoughts?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...
  • I’m a Sexy and Naughty T-Girl Here in Winnipeg.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 ...
  • April 6th, 2025
  • F/M seeking love and funF/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...
  • The Trevor Project Saves Young LGBTQ+ LivesThe Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Winnipeg Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexua...
  • TS Temptress Ready to Ruin You (In the Best Way) πŸ˜ˆπŸ’¦ WinnipegTS Temptress Ready to Ruin You (In the Best Way) πŸ˜ˆπŸ’¦ Winnipeg  Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • Smoke me out baby!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'...
  • πŸ†πŸ’¦ Canada Shemale I Need to Date a Sexy ManπŸ†πŸ’¦ πŸ†πŸ’¦ Canada Shemale I Need to Date a Sexy ManπŸ†πŸ’¦ Canada Shemale ReadyNeeding sex here in Canada Canada πŸ“²  Transsexual Dating App  I'm new to Canada from America, but I need a sexy man to date and have some sexy fun..  I'm a transsexual or sometimes reffered to as a Shemale and I have a nice big cock for you.. Would you like to ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!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 ...
  • Sexy hung and big bustedSexy 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....
  • INTERACTIVE MAP: Transexual Tracker in the Winnipeg Area!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 ...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy  Winnipeg!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 ...