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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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May 19th, 2025

Looking for a TS Woman Who Loves to Be Desired 💦🔥 Windsor 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...

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...

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...

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...

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

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Windsor? Hey, I am Jasmin, 8" 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...

I’m a Sexy and Naughty T-Girl Here in Windsor. Windsor T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Windsor 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 st...

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...

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...

TS m/f switch 28 new here TS m/f Switch in Windsor 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...

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 ...

Erotic exotic Asian queen in Windsor now (25) Asian Transexual in Windsor 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....

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...

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...

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...

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...

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...

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! ...

Superb Shemale in Windsor... T-Girl for NSA Encounters in Windsor When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Windsor. 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 and ...

Shy Transexual Escort in Windsor 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 ...

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 ...

Windsor 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 ...

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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...

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 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...

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!...

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. ...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Windsor Area Hi, my fem name is Gloria. I'm a married crossdresser in the Windsor area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing fr...

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 ...

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Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Windsor View My Personal Pix - 🤫 A sexy Crossdresser from Windsor, 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 a...

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...

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,...

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...

I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Windsor I'm queen Delilah a trans woman here in Windsor 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 position...

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...

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 ...

TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Windsor Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...

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....

Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Windsor 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,...

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...

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...

Ebony Shemale in Windsor ❤️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies 💋 Are you looking for a hot and kinky black shemale in Windsor? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale.. I am a stunning transgender woman who loves to pla...

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...

🍑 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...

Windsor's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Windsor Hi you sexy man! I'm Toni a trans woman from here in Windsor. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung, functional and loves...

Don't Worry I Bite! Feisty redhead trans in Windsor 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 m...

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 ...

💦 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 ...

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