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!
Home / Dating / Transgender
Show Ads In: Winnipeg | Brandon
- June 15th, 2026
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 @PennyTSswitch!!
I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and e...
Black/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋 Warning: I’m addictive 😘 View My Ebony TS Profile here -
I possess more than attractive features. I am a complete TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and thick thighs and soft lips and a hidden secret th...
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...
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 @SelenaIsTrans and send me a message to set up a date.
I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...- June 14th, 2026
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...
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...
Cute TS Sugar Baby Seeking Male💎Aria Username: @AriaSweet
Trans Friendly: Yes
Private Meetups: Yes
Phone Chat: Yes
Pics Available: 18
Message me if you like feminine Transsexual 💬
Hello, I am AriaTS here in Winnipeg. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a man ...
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...
💜 Cute TS Girl Looking for the Right Guy 😘 Just moved to Winnipeg😊 Gorgeous, very sweet and easy to get to know. I am a trans girl seeking to meet men that are confident and know what they are looking for, yet are also looking for some friendship with a new person. I enjoy going out for cocktails and having a good time, flirting with the ...
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...
Road Head Sally Drivin' Hard in Winnipeg Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Winnipeg. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or par...
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!...
Flawlessly gorgeous trans bombshell in Winnipeg Trans MtF for Man in Winnipeg
I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom ...
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋 📍 Location: Winnipeg
💖 Seeking: Fun, Exciting, & Discreet Connections
Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I'...- June 13th, 2026
TS Sugar Baby 💎 Femme, Flirty & Looking for the Right Man in Winnipeg I’m a transgender sugar baby who loves femininity, attention, and being appreciated by a confident man who knows exactly what he wants.. Confidence speaks louder than words. Gentle touches matter more than grand gestures ever could. Let's Link Up Babe -
Fond of the sugar dynamic. Getting pamp...
Hot trans chick with nice boobs Hot trans chick in Winnipeg. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want t...
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'...
Tiffany Shelle - Your Winnipeg Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Winnipeg
It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!
I'm 100% functioni...
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 @BlancaShemale32 with your recent pic or selfie for my latest pictures and p...
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 ...- June 12th, 2026
TS Temptress Ready to Ruin You (In the Best Way) 😈💦 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...
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...
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...
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 ...