Hamilton, Ontario Shemale Dating Classifieds

Hamilton, 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!

Home / Shemale Dating /

Show Ads In: Barrie | Brantford | Belleville | Chatham | Cornwall | Guelph | Hamilton | Kingston | Kitchener | London, Ont. | Niagara | Ottawa | Owen Sound | Peterborough | Sarnia | Sault Ste Marie | Sudbury | Thunder Bay | Windsor | Toronto

  • May 19th, 2025
  • Looking for a TS Woman Who Loves to Be Desired ๐Ÿ’ฆ๐Ÿ”ฅ HamiltonLooking for a TS Woman Who Loves to Be Desired ๐Ÿ’ฆ๐Ÿ”ฅ Hamilton  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. ๐Ÿ’‹ I would love to meet a shemale or tra...
  • Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Hamilton Seeking!!Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Hamilton Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. ๐Ÿ˜ 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!Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Hamilton 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...
  • TS Latina Bombshell โ€“ Your Secret Addiction, Your Midnight Obsession ๐Ÿ˜ˆ๐Ÿ‘TS Latina Bombshell โ€“ Your Secret Addiction, Your Midnight Obsession ๐Ÿ˜ˆ๐Ÿ‘  Hola, mi amor ๐Ÿ˜˜ 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! HamiltonYOUR EBONY SHEMALE - big boobs and a BIG COCK! Hamilton Hot Hot Hot! Sinead, a black shemale in Hamilton ready to make all of your  wildest fantasies come true! ๐Ÿ’‹๐Ÿ”ฅ My Pictures and Profile! -- You want to find a sexy ebony shemale in  Hamiltonto fulfill all your dreams? Then stop searching because I am ready to make  all of your dre...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Hamilton? 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...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Hamilton.Iโ€™m a Sexy and Naughty T-Girl Here in Hamilton. Hamilton T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Hamilton 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 ...
  • Flawlessly gorgeous trans bombshell in HamiltonFlawlessly gorgeous trans bombshell in Hamilton Trans MtF for Man in Hamilton 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 ...
  • Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina ๐Ÿ’‹ I'm in Hamilton 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...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Hamilton 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...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Hamilton Look no further honey, I'm Franny an Ebony trans woman here in Hamilton 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...
  • Erotic exotic Asian queen in Hamilton now (25)Erotic exotic Asian queen in Hamilton now (25) Asian Transexual in Hamilton 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-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Hamilton 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: GayleTG...
  • 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 Hamilton area come see if you measure up! Click here for explicit photos. Look ...
  • TS Latina Goddess โ€“ For Men Who Crave Passion, Fire & Pleasure ๐Ÿ”ฅ๐Ÿ’‹TS Latina Goddess โ€“ For Men Who Crave Passion, Fire & Pleasure ๐Ÿ”ฅ๐Ÿ’‹  Hello sweetheart ๐Ÿ˜˜ 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?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 Hamilton tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...
  • Spicy ๐ŸŒถ  Latina Shemale in Hamilton Ready to Fill You ๐Ÿ˜‰๐Ÿ˜‰ Spicy ๐ŸŒถ Latina Shemale in Hamilton Ready to Fill You ๐Ÿ˜‰๐Ÿ˜‰ LATINA SHEMALE SEEKING ๐Ÿ”ฅ๐ŸŒถ  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Hamilton.  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 ...
  • Hi Guys!! I am looking for someone fun!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 Hamilton...Superb Shemale in Hamilton... T-Girl for NSA Encounters in Hamilton When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Hamilton. 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...
  • Shy Transexual Escort inย HamiltonShy Transexual Escort inย Hamilton 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 Hamilton I know You Want to Play Sexy Shemale Hamilton 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 Hamilton; 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...
  • Hamilton Addicted to shemales... Male Seeking TSHamilton 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 ...
  • TS Beautiesโ€”Letโ€™s Make Some Memories ๐Ÿ’–โœจTS Beautiesโ€”Letโ€™s Make Some Memories ๐Ÿ’–โœจ  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...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hamilton )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hamilton ) Sexy Crossdresser Elissa Looking for Hot Fun in Hamilton๐Ÿ’‹    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 ...
  • 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 Hamilton area. Click here and come see me anytime!...
  • Hot sexy shemale doll visiting Hamilton now Hot sexy shemale doll visiting Hamilton now Shemale Visiting Hamilton 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.Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Hamilton Area Hi, my fem name is Gloria. I'm a married crossdresser in the Hamilton 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 ...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Hamilton Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Hamilton. 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...
  • 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  ...
  • Local Crossdresser ๐Ÿ˜‰๐Ÿ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser ๐Ÿ˜‰๐Ÿ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Hamilton View My Personal Pix - ๐Ÿคซ  A sexy Crossdresser from Hamilton, 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...
  • 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 H...
  • Looking for My TS Queen ๐Ÿ‘‘๐Ÿ’‹Looking for My TS Queen ๐Ÿ‘‘๐Ÿ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. ๐Ÿ’• 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 ๐Ÿ†๐Ÿ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK ๐Ÿ†๐Ÿ˜‰ BBC SHEMALE - BLACK TRANS๐Ÿ’Ž 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...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Hamilton I'm queen Delilah a trans woman here in Hamilton 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...
  • British T-girl Seeking Classy Gentleman in Hamilton...British T-girl Seeking Classy Gentleman in Hamilton... 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 Hamilton and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excep...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Hamilton 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)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Hamilton Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • 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....
  • 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 Hamilton 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...
  • II'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 Hamilton 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...
  • Letโ€™s Get a Drinkโ€ฆ and See Where It Leads ๐Ÿ˜˜Letโ€™s Get a Drinkโ€ฆ and See Where It Leads ๐Ÿ˜˜  One Night, No Limits...  HamiltonShemale Seeking Man for sex๐Ÿ’ฆ View More of My Pix - โœ… 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 sh...
  • Ebony Shemale in Hamilton โค๏ธ๐Ÿ˜˜ Seeking Male for Naughty Fun!Ebony Shemale in Hamilton โค๏ธ๐Ÿ˜˜ Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies ๐Ÿ’‹ Are you looking for a hot and kinky black shemale in Hamilton? 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 pl...
  • New Body New MeNew Body New Me M2F post-op in Hamilton 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...
  • HamiltonHamilton's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Hamilton Hi you sexy man! I'm Toni a trans woman from here in Hamilton. 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 lov...
  • DonDon't Worry I Bite! Feisty redhead trans in Hamilton 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 ...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Hamilton 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...
  • ๐Ÿ’ฆ Thick, Juicy & Kinky โ€“ Come Experience the Best ๐Ÿ˜๐Ÿ’ฆ Thick, Juicy & Kinky โ€“ Come Experience the Best ๐Ÿ˜  ๐Ÿ”ฅ| 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 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Hamilton 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 naug...
  • TS Beautiesโ€”Letโ€™s Have Some REAL Fun! ๐Ÿ˜๐Ÿ”ฅTS Beautiesโ€”Letโ€™s Have Some REAL Fun! ๐Ÿ˜๐Ÿ”ฅ  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. ๐Ÿ’‹ Must  have confidence, charm...
  • ๐Ÿ‘‘ TS Ebony Goddess Looking for Her King Tonight ๐Ÿ”ฅ๐Ÿ‘‘ TS Ebony Goddess Looking for Her King Tonight ๐Ÿ”ฅ  ๐Ÿซ Juicy, thick, and so addictive! I am a stunning ebony trans  vixen with the perfect hourglass figure, long legs, and a playful personality. I have a  thing for men who know what they want and are not afraid to go after it. Whether you are  a professional or a newbie to the ...