Windsor, Ontario Shemale Sex Service Providers

Windsor, Ontario shemale sex service providers. Find local crossdressers, transexuals and shemale sex providers including shemale escorts, body rubs, strippers, dom & fetish and more. Select your location below to find shemale sex providers near you. It's free to search or post your own ad!

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  • October 17th, 2025
  • 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 Windsor boos out there. I'm an independent trans escort serving the Windsor area. 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 sexy, hung and fun. You c...
  • Tiffany Shelle - Your Windsor Tranny Girlfriend! 💞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% functioning shema...
  • INTERACTIVE MAP: Transexual Tracker in the Windsor Area!INTERACTIVE MAP: Transexual Tracker in the Windsor Area! Local Trans Hookups Meet local transexuals in the Windsor area for friendship or sex hookups. View our interactive map below to meet local trans members who want to meet local transexuals or admirers. Click a thumbnail to get started now! Interactive Windsor Trans Hookups Map ...
  • Hey Windsor - IHey Windsor - I'm Nastina With the BIG Weena!... Windsor Trans Escort 4 Hire Nastina here a fully passable in social situations, fully functional in bed and packin' a BIG surprise for ya! I'm the best trans escort in the Windsor area so don't even mess with the rest big boy. Discreet, top or bottom, incall, outcall, events ok, women ok. No h...
  • TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!!TATTOOED TRANSSEXUAL 🔥💥 HERE FOR SEX AND FUN!! LOCAL SHEMALE ESCORT LISTINGI reside in {City} and I'm always ready! I have photos, with feedback from satisfied customers .. I will always satisfy and make you feel like the AMAZING MAN you are!! I also have been verified through P411 ✅💍 and you can also find me on OF, Want to see more pictur...
  • Welcome to the Land of Neons and Nylons Baby!Welcome to the Land of Neons and Nylons Baby! Big City Kitty here to share the glamour that is Windsor with a sexy man tonight. You can take me anywhere, I'm a fully passable t-girl, functional and always in the mood for some hot sexy fun. Incall, outcall, travel, events, parties or anything you have in mind. I like it flashy and trashy! If you...
  • Your Trans Fantasy Starts Here – Let’s Cam First 💦Your Trans Fantasy Starts Here – Let’s Cam First 💦  Looking for a sexy, open-minded transgender woman in Windsor? That’s me! I  love connecting on cam—it’s the perfect way to get to know each other before possibly meeting up.  She/Her, sensual, spontaneous, and ready to play. Click the link, view my  profile, an...
  • S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱S Beauty for Cam, Chemistry & Midnight Conversations 🌙📱  Hey handsome 😘 You will find me attractive because I am a trans woman who combines sweetness with  sensuality and playful nature. During my transition I use She/Her pronouns because I seek authentic  connections between two people. View My Profile and Message  Me – I&rs...
  • Vietnamese Trans Escort Serving the Windsor Area...Vietnamese Trans Escort Serving the Windsor Area... kawaiiTranX is back on demand in Windsor for all loyal admirers. I a fully passible and functional trans female escort who can take care of you like no body else can. I make you wonder how you ever got along without kawaiiTranX before. Incall, outcall OK, no women, underage or police! Come see ...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Escort in Windsor Hi I'm trans escort Trisha here 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. This is for a kinky open minded man sort of man who appreciates w...
  • Your TS Cam Crush is Ready to Connect – Come Play 💦💋Your TS Cam Crush is Ready to Connect – Come Play 💦💋  Seeking a smart trans girl who can turn you on with her smile and voice? Look no  further 😘 I’m a TS woman with soft curves, a curious heart, and a dirty  little secret. I use She/Her pronouns and I love sharing raw, real moments on cam  — the kind that make your...
  • Windsor Come See a Local Ebony Tranny Dance on The PholeWindsor Come See a Local Ebony Tranny Dance on The Phole  Ebony TS Goddess Seeks a VIP Date! 💵💰💎  Hey boys, I'm an Ebony Transsexual in Windsor and I'm dancing tonight. Come hang out.. Let's have a few shows and maybe a dance. If you say you found me from this ad, I'll give you a SPECIAL DANCE!!! 👸💦 You like curves, confiden...
  • EBONY🍆TS - incall and outcall💦EBONY🍆TS - incall and outcall💦 Ebony Shemale With BBC🍭do you like pretty black TS? My Personal Profile - View Here Name: PARIS EBONY TS 🍆 Ethnicity: Black - Ebony Age: 23 years old Height: 5'5"  Weight: 134lbs Location: Local, Willing to travel Op: Pre-Op 🐈 ( Still have my Cock) Services: B...
  • Road Head Sally DrivinRoad Head Sally Drivin' Hard in Windsor Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Windsor. 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 park at s...
  • Gloria Windsor trans escort has a secret in her panties!! 🍭Gloria Windsor trans escort has a secret in her panties!! 🍭 Gloria, Trans Escort in Windsor 💋 NO BLOCKED NUMBERS - Please message me @GloriaTransXual. I'm Gloria and I have a big secret hiding in my panties. I'm completely passable so you can take me out to a business dinner or a fancy restaurant. Only you and I will know the secret that awaits you ...
  • Seductive Roselia is excited to make your wildest dreams 💦 true WindsorSeductive Roselia is excited to make your wildest dreams 💦 true Windsor SHEMALE BODY RUBS AND MASSAGE Located in Windsor - Stop on in! 👄😻    Looking for a Sexy and Sensual Massage from a TS/Shemale, in Windsor? Well search more! I'm Roselia ( SHE/HER ). I'm here to make sure you have a time with me ✨  As a transgender woman I love what I do...
  • Come Play with BRITx – a TS Beauty in Windsor 💃Come Play with BRITx – a TS Beauty in Windsor 💃 BackRoom with BRITX – TS Beauty in Windsor 💃 My Stripper Pix - Profile✅  Hello there! I'm Laryssa. I enjoy embracing fun and excitement in life while cherishing the moments of joy and fulfillment with others, around me too. Tonight you can find me at the club having a time dancing ...
  • Windsor Transsexual Body Rubs 💋 Kiss & Slide SessionWindsor Transsexual Body Rubs 💋 Kiss & Slide Session  Do you crave closeness? I’m the TS goddess who gives more than just a massage—I  give connection, fantasy, and deep release. I will touch you with warm oil and soft skin while  my body is pressed against yours from chest to chest with our mouths together and our hips and...
  • Independent Shemale Escort Top or Bottom in WindsorIndependent Shemale Escort Top or Bottom in Windsor Top or Bottom Shemale Escort in Windsor Hey guys. I'm Maya Grace (@MayaGrace31). I am a sexy and sweet, but also naughty shemale in the Windsor area. I'm friendly and outgoing, a total flirt and a tease. I will definitely make you feel proud to be with me. I will leave you happy & relaxed every...
  • 24 y/o Crossdresser 🍭 seeks Man for Dates in Windsor24 y/o Crossdresser 🍭 seeks Man for Dates in Windsor Crossdresser Escort in Windsor Girly crossdresser Ashley here for to service a men and I do know what you like! I'm always fun and flirty and clean and very feminine. No drama or rudeness ever. Incall/outcalls available. Contact me for same day appointment. I have a clean, safe place or you name th...
  • Cam Now, Hookup Later? Trans Girl in Windsor 🖤Cam Now, Hookup Later? Trans Girl in Windsor 🖤  Let’s have some real fun. I’m a naughty trans girl who’s up for cam play  and possibly more. Let’s chat, get each other going, and see if we vibe enough to  meet. I’m flirty, freaky, and love being watched. Hit me up, view  my page, and let’s ...
  • Black 🍆 CrossdresserBlack 🍆 Crossdresser  EBONY/BLACK CROSSDRESSER  WITH NICE HUGE, HARD COCK🍭 - VIEW MY CROSSDRESSER PROFILE HERE - ❤️BLACK CROSSDRESSER❤️WILLING TO TRAVEL❤️SEX AND BLOWJOB👅 I WANT TO DRESS UP SUPER CUTE AND SEXY THEN I WANT US TO EXPLORE OUR WILDEST AND NAUGHTIEST FANTASI...
  • Let’s Get Wild Online First – Trans Beauty in Windsor 👠Let’s Get Wild Online First – Trans Beauty in Windsor 👠  As a trans girl I have a passion for cam sessions which I describe as naughty, raw and  real. I am located in Windsor and I am open to meetups if the vibe  is hot. I identify as She/Her, enjoy exploring and I am willing to try anything that  feels good. I want to flirt, tease an...
  • Black BambiBlack Bambi's Got a BIG Love Gun and it's Loaded Baby! Windsor Trans Escort Black Bambi I shoot to thrill! Hey boys your gonna get more bang for your buck with BlackBambi in Windsor! Don't go off half-cocked with those other trans escorts out there and be left wanting for more. I'm smokin' hot top or bottom incall, outcall, parties, events, discreet, p...
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  • She/Her TS Babe Wants Late Night Chats & Real Chemistry 😘She/Her TS Babe Wants Late Night Chats & Real Chemistry 😘  Do you want to experience genuine conversation together with a trans woman who understands how to maintain playful and  exciting relationships? 😘💋 Check out My Profile then Send Me a Message because I want to  ignite this connection. As a transsexual girl I possess both a larg...
  • SHEMALE INTO KINK 🔥 I WILL DOMINATE YOUSHEMALE INTO KINK 🔥 I WILL DOMINATE YOU Sexy Shemale DOMINATRIX Maryjo let's explore our kinks together!😈 My Name in Maryjo and I'm located in Windsor.. I'm a very Kinky and horny shemale to play with your body and mind!💦  I want to own you and make you cry out in pleasure and pain. I will do unspeakable things to you and...
  • OnebitchinOnebitchin' Babe in Windsor Im a Funloving Person... You must live in the Windsor area I am a Trans escort and will sex you up hard because I'm ALL the woman you need tonight baby! Tell me how you want it, you must be honest 100% No Bullsh#t. No games. No cops, no minors or lowballers PLEASE!! Sex isn't mandatory but, you must please be clean, respect...
  • SHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE WITH 8 INCHESSHEMALE TOP LOOKING FOR BOTTOMS, VERSATILE WITH 8 INCHES Shemale Top for Bottom in Windsor Hello Gentlemen!!!  I'm the girl your momma warned you about.  I am Ginger, mixed race, age 28. I am a stunning temptress w/ lovely personality very friendly confident & discreet... Have your very best experience with me.. TOP & BOTTOM!! Don...
  • II'll be your sexy superhero tonight baby!... Yeah baby it's super tranny to the rescue in Windsor. Freaky as hell and I always rise while others fall. If you need a sexual superhero tonight then I'm your girl. I got 9 inches uncut that wants you to have your way. Oral, hand, anal or? Anything you want this ebony trans escort is good with. Goin...
  • LetLet's Meet on Cam Then Meet up Windsor📱🎥 Let's Chat ONLINE 🟢  and Then Meet Exciting Transsexual, in Windsor  wanting to get to know each other and then possibly meet up.. See what we can make of things😇💫✨ Are you, in search of a transgender woman who can fulfill all your wishes and needs? No need to loo...
  • 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? Windsor T-Girl Escort You don't know the difference? 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 escort tonight. Save your appetite boy! Me: trans, 30yrs, 5...
  • Trashy Tranny Trisha...Trashy Tranny Trisha... Trashy Windsor Trans Escort Hey I'm Trisha here in Windsor, and one man's trash is another man's treasure! Sure I'm nasty, I'm dirty minded, I'm horny AF and a little wild but that's a win-win for the both of us baby! I'm 5'8, medium build with a big hard uncut package, 160 pounds, top or bottom an...
  • Hung Black Shemale Top or Bottom for Windsor Gentleman 🌟Hung Black Shemale Top or Bottom for Windsor Gentleman 🌟 Hung Black Shemale for Windsor Gentleman Hi there! My name is Lady Velvet. I am the perfect package to explore all your hidden shemale fantasies.✨🍭 I guarantee you’ll come back running for more! 💋 I am a real shemale with a full, thick 100% operational🍆 , can service you top or bot...
  • Hot Natural Tgirl in WindsorHot Natural Tgirl in Windsor Hot Natural TGirl Companion I'm a 33 y.o shemale/trans girl looking to provide a great time for a fun, good man. I am versatile, very sensual and full of fun. I like to kiss as well...;) Feel free to inquire on further details. 420 friendly You will like what you see. Clean and safe play Visit me...
  • Online Now 🟢 Ready to Play and Possibly Meet IRLOnline Now 🟢 Ready to Play and Possibly Meet IRL  A transsexual woman from Windsor seeks someone to chat and flirt with potentially leading to  relationship formation. Your search for a passionate trans encounter ends here. I am currently transitioning and use  She/Her pronouns while enjoying hot moments especially when I am on came...
  • Windsor 😍 Yessica TS Escort 🍆 Use meWindsor 😍 Yessica TS Escort 🍆 Use me TS Escort Ready and Available - Do Whatever You Want! TS Yessica ( Real Shemale Escort )  come have some fun 😍 I'm ready for watever ! Throat goat 👅 foreal baby looking to have a good time and please you daddy so if your looking for a good time call me plz be serious when contacting me d...
  • NURU MASSAGE WITH SHEMALE - 🌺 Slow, Wet, & IntimateNURU MASSAGE WITH SHEMALE - 🌺 Slow, Wet, & Intimate  You deserve intimacy. You deserve indulgence. You should lie down so I can explore your entire  body with erotic purpose. View My Profile - My nuru body rubs are wet, slow, and wildly erotic. I  will move my body against yours while sharing dirty dreams through whispers and allowing...
  • Dr FreakinDr Freakin'Furter - Mine's Bigger Than Yours! White, 32 year old T-girl escort Freakin'Furter here in Windsor, 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 ...
  • WindsorWindsor's Own Trans Escort FABULOUS FRANCIS - I'm a Born Diva Honey!... T-Girl Escort in Windsor I'm Fabulous Francis a trans escort here in Windsor serving all you sexy guys with my sexy womanly wiles. I'm all the F-words baby! Fabulous, fun, fantastic, functional, friendly, flambouyant and very f#ckable! I do top or bottom and am extra large=well equipped. Let's make...
  • ON STAGE TONIGHT!!  Shemale Laryssa 💋 Windsor ON STAGE TONIGHT!! Shemale Laryssa 💋 Windsor Sexy Shemale Laryssa Ready to Fulfill Your Wildest Fantasies 💋 Hey there, handsome! I'll be at the club tonight.. I will treat you extra special in the back room, if you know what I mean 💦👄 Are you looking for a sexy shemale in Windsor  who knows how to have a good time? Look no furth...
  • Trans Goddess Seeking VIP Companion!💎💎Windsor💎💎 Hispanic Tranny Dancing TonightTrans Goddess Seeking VIP Companion!💎💎Windsor💎💎 Hispanic Tranny Dancing Tonight Spicy, Sultry & Down to Mingle!Hispanic and Spicy Latina TS 👗🔥 I don’t just dance, I seduce. 😏 If you love an exotic, trans beauty who knows how to tease, I’m waiting at the club and I'm bored.. Ughh, please come save me and let's have some fun. I want to take a few shots w...
  • Looking for THE hottest drag queen in Windsor?Looking for THE hottest drag queen in Windsor? Drag Queen Escort Ready to go to the real drag races sexy? Of course you are! Why else would you be scopin' out my Windsor trans escort listing? I'll take you to the races tonight and we'll run a few laps and get you to the finishing line for the BIG WIN BABY!!! The checkered flags are up and ...
  • Windsor - 🔥 TS Temptation TouchWindsor - 🔥 TS Temptation Touch  You will find me different from other body rub babes because I am the trans temptation which has been  on your mind. My expert hands and full lips and soft curves will provide you body massage experiences you  never had before. view my sexy trans profile here - The nuru gel serves ...
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  • 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 Black Sh...
  • 🖤 Touch Me, Tease Me, Take Me Windsor Shemale Rubs🖤 Touch Me, Tease Me, Take Me Windsor Shemale Rubs  Are you aching for real connection? Come touch me. Our bodies will merge as I position  myself above you to share my fantasies while our skin dissolves into each other. View My Profile and Pictures - I’m a TS  goddess who loves kissing, sucking, licking, teasing, and intense ...
  • Online Cam Fun? Then Maybe Hookup? 👄💻Online Cam Fun? Then Maybe Hookup? 👄💻  I am a trans woman living in Windsor and I am open-minded and always ready  to explore. What do you want to know about me? Let’s chat first—cam to  cam—and see if there is a connection. 🔥 She/Her, and all about making fantasies come  true. Let’s get wi...
  • First timer, or simply curious, youFirst timer, or simply curious, you'll feel completely comfortable with me. I'm very discrete I am 25 year old fully-functional TS girl.  Let's get the physical stuff out the way first - I'm completely passable transexual (and then some). I have an amazingly sensuous model's body - toned and smooth, educated and classy. My measurements are 36D-29-34. I have a 9.5 inch thick, 100% fully...
  • Hot Chocolate Encounters of the Trans Kind Tonight in Windsor Baby!Hot Chocolate Encounters of the Trans Kind Tonight in Windsor Baby! Ebony Tgirl Escort in Windsor Dark chocolate t-girl escort here to rock your world in Windsor. I'll make you feel alright with my big goodbar tonight. I'm an animal baby just doin' what comes natural. I am discreet and welcome incalls and outcalls women, couples, gay men, groups and just about...