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Windsor, Ontario

Windsor, Ontario Shemale Dating Classifieds

Windsor, Ontario 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!

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September 18th, 2025

Tiffany Shelle - Your Windsor Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Windsor 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% functionin...

Tainted Love - Beyond Compare! Kinky Trans Woman in Windsor Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Windsor. 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 what ...

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 ...

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 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...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Windsor 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 ...

Sexy hung and big busted Hung and Busty Shemale in Windsor 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....

Trans Playmate Sex Kitten... Ebony trans woman in Windsor 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 ...

🍑 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...

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥 🔥| 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 ...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Windsor 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 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naugh...

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 Windsor 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 ne...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Windsor 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.. Le...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Windsor Secret Crossdressing Hookups in Windsor 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 gar...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Windsor 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: GayleTGi...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Windsor 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 sex...

Spicy and Hot T-Girl from Colombia Latina T-Girl in Windsor 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...

💖 Discreet, Naughty & Waiting for a Man Who Can Handle Me 🔥 I’m an exotic ebony TS bombshell in Windsor 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 neve...

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....

TS Beauties—Let’s Make Some Memories 💖✨ I am a dominant, attractive, and confident man looking for a beautiful transgender woman who enjoys being admired, spoiled, and pleasured. I am down for mutual attraction, passionate flames and unforgettable moments. Whether it is a one time or if it is something on going I a...

Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Windsor 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 ...

Flawlessly gorgeous trans bombshell in Windsor Trans MtF for Man in Windsor 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 r...

British T-girl Seeking Classy Gentleman in Windsor... 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 Windsor and am financially independent and looking for a gentleman who is like-minded, equally solvent and has except...

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...

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 Windsor area and are interested then drop me a line and introduce yourself. You can ...

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 sexy shemale doll visiting Windsor now Shemale Visiting Windsor Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...

Let’s Play a Game—Winner Gets Me 😉 Windsor 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...

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Tantalizing Tina with a HUGE W33NAH! Windsor Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Windsor 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: 2...

Let’s Get a Drink… and See Where It Leads 😘 One Night, No Limits... WindsorShemale 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 sho...

Beautiful Krystale 25 Windsor visiting now Beautiful Shemale Visiting Windsor Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me. Krystale25shemale Age: 25 Location: Windsor Sex: Shemale Seeking: Man ...

F/M seeking love and fun Female to Male Trans Man in Windsor 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 gro...

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Windsor ) Sexy Crossdresser Elissa Looking for Hot Fun in Windsor💋 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 p...

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Windsor Look no further honey, I'm Franny an Ebony trans woman here in Windsor 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 to ...

Hot trans chick with nice boobs Hot trans chick in Windsor. 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...

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...

New Body New Me M2F post-op in Windsor 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 Natasha...

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 Windsor area. Click here and come see me anytime!...

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 Windsor tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than...

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 Windsor area come see if you measure up! Click here for explicit photos. Look f...

Sexy Shemale Windsor 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 Windsor; 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 ...

Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷 You are not the typical girl who lives in the next house… You are the woman who occupies your thoughts when you are with the woman who lives next door. Message me here!! I’m a TS Latina goddess — I have the shape of a coke bottle, the lips of sin, and a t...

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She-male looking for hot date to please. Asian Shemale in the Windsor 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 ...

Spicy 🌶 Latina Shemale in Windsor 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 Windsor. 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 t...

Windsor 😈🍆💦 Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking 🔥Ready to Fulfill Your Wildest Fantasies My Spicy Latina Shemale Pix! -Are you looking for a sexy shemale to play with? I'm a bit of a drama queen. I love dressing pretty and getting my nails done. I will also dress sexy in lingerie for you. Do you want to have a hoo...

Latina TS Firestarter – I Don’t Do “Mild” 🔥👠 I’m your next obsession, papi 😘 View More Pictures of Mine! TS. Latina. Voluptuous. Insatiable. And craving a man who can handle my curves, my tongue, and my need for deep, sweaty pleasure 😈 You’ll taste my perfume before I even touch you… and feel my body long after I lea...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Windsor 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's...

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...

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