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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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April 18th, 2025

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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...

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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MALE SEEKING SHEMALE 🍆Windsor Ready to Play and Fuck 💦 I have a secret.. 🤫 I've always want to see what it's like to play with a shemale!! Hi I'm John, I'm in Windsor and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a good heart an...

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...

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...

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...

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...

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...

FtM seeking Princess Bride in Windsor FtM seeking Woman in Windsor Hi, I'm Andy, age 33, FtM transgender man living in Windsor. 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 @AndyFtM4P...

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 ...

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 ...

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 ...

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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...

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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 ...

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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...

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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...

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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...

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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...

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...

April 17th, 2025

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...

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 ...

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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...

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! ...

Hot Shemale in Windsor Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Windsor My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Windsor 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 havin...

🍑 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...

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,...

💖 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...

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...

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Seeking All TS Beauties in Windsor 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...

Shemale 4 Men 🍆💦 Windsor Ready Now!! Come Closer, I Don’t Bite, Unless You Do Enjoy It😉 View My Private Pictures - If you’re looking to mess around… I don’t know, maybe in a way that’s a bit spicy for the two of us? I’m a trans beauty with a dirty mind and I love...

💦 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 ...

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...

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