Kentucky Shemale Dating Classifieds

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Show Ads In: Bowling Green | Huntington-Ashland | Lexington | Louisville | Western KY

  • June 23rd, 2026
  • New Body New MeNew Body New Me M2F post-op in Kentucky 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...
  • MALE SEEKING SHEMALE πŸ†Kentucky Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Kentucky Ready to Play and Fuck πŸ’¦ 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 Kentucky  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 a...
  • Lexington Thoroughbred T-Girl Filly in Season Baby!Lexington Thoroughbred T-Girl Filly in Season Baby! Fancy Filly t-girl in season here in Lexington wanting a man to take her to the Derby for a few laps. Ride me baby, ride me rough and hard and get me to the finish line. Don't worry I will bring lots of Kentucky's favorite jelly - KY! Enough of the puns, sorry I cant resist. This is a serious person...
  • Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯  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...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! KentuckyYOUR EBONY SHEMALE - big boobs and a BIG COCK! Kentucky Hot Hot Hot! Sinead, a black shemale in Kentucky ready to make all of your  wildest fantasies come true! πŸ’‹πŸ”₯ My Pictures and Profile! -- You want to find a sexy ebony shemale in  Kentuckyto fulfill all your dreams? Then stop searching because I am ready to make  all of your dre...
  • A monster in the sheets, but a lady in the streets...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 Kentucky area and are interested then drop me a line and introduce yourself. You can...
  • One Night, No Rules, Just Pleasure… One Night, No Rules, Just Pleasure… Kentucky I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🀫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktails....
  • 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 K...
  • TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨  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...
  • 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 Kentucky area come see if you measure up! Click here for explicit photos. Look ...
  • πŸ‘ Your Secret Ebony Fantasy Is Just One Message Away πŸ˜œπŸ‘ Your Secret Ebony Fantasy Is Just One Message Away 😜  πŸ‘„ 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...
  • 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 Kentucky tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer tha...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Kentucky Looking for someone a little different from the average guy? Hey, I'm Barry, age 31, fit and healthy. I have a square jaw, sparkling eyes and short dark hair. I like to dress sharp. I am currently looking for a fun lady to spend time with. Possible longterm relationship.&...
  • TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯  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...
  • Ebony Shemale in Kentucky ❀️😘 Seeking Male for Naughty Fun!Ebony Shemale in Kentucky ❀️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies πŸ’‹ Are you looking for a hot and kinky black shemale in Kentucky? 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...
  • KentuckyKentucky's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Kentucky Hi you sexy man! I'm Toni a trans woman from here in Kentucky. 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...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Kentucky 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'...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ KentuckyYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Kentucky I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. πŸ’‹ πŸ‘  Feminine, fun and ...
  • I Need a STEAM ROLLER Baby!!!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 ...
  • Shy Transexual Escort inΒ KentuckyShy Transexual Escort inΒ Kentucky 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 ...
  • Spicy 🌢  Latina Shemale in Kentucky Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Kentucky Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Kentucky.  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 ...
  • Sexy Shemale Kentucky I know You Want to Play Sexy Shemale Kentucky 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 Kentucky; 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...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰ BBC SHEMALE - BLACK TRANSπŸ’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...
  • Kentucky πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Kentucky πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯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...
  • Email Kentucky Shemales❀️‍πŸ”₯Email Kentucky Shemales❀️‍πŸ”₯ I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
  • 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 Kentucky 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 Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Kentucky Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Kentucky with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see ...
  • 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 Kentucky 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...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Kentucky )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Kentucky ) Sexy Crossdresser Elissa Looking for Hot Fun in KentuckyπŸ’‹    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 ...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Kentucky Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Kentucky Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Kentucky to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat ...
  • Email Local Shemales Now! πŸ’ŒEmail Local Shemales Now! πŸ’Œ Want to Hookup and Find Local Shemales? RADE PIX - MESSAGE - BROWSE PROFILES This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you'reinterested in πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • Well Endowed Shemale is beautiful Kentucky 32Well Endowed Shemale is beautiful Kentucky 32 Well Endowed Shemale in Kentucky I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me at BlancaShemale32 for my latest pictures and proof of my size!&nb...
  • πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯πŸ‘‘ TS Ebony Goddess Looking for Her King Tonight πŸ”₯  πŸ« 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 ...
  • British T-girl Seeking Classy Gentleman in Kentucky...British T-girl Seeking Classy Gentleman in Kentucky... 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 Kentucky and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excep...
  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  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...
  • June 22nd, 2026
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  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...
  • TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹  You can find me at the bar where I serve drinks and flirt with customers while enjoying the  atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that  doesn’t stop until you beg me to πŸ’‹ I’ll start off sweet, flirty, &nbs...
  • 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  ...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Kentucky 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 gr...
  • 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 Kentucky area. Click here and come see me anytime!...
  • LOUISVILLE😈TRANNY SEXLOUISVILLE😈TRANNY SEX I'm a Sexy Shemale LIVINGIN Louisville, Kentucky β€οΈπŸ˜‰ Message Me Now For a Sexy TGIRL Date I'm a post opp Transsexual with a big cock.I also have some nice big boobies you canplay with and suck on.. I'm in Lousville, Kentucky and I love to get out and have fun.You fancy a nice big cock ...
  • 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 Kentucky 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...
  • Fuck a TGIRL Tonight ❀️😘Fuck a TGIRL Tonight ❀️😘 Hi babe, Amber Lynn, I'm a TGirl and I'm ready to meetup and hookup in KY 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. Send me a message now.. Let's make it happen! βœ… ☎️ Tex...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Kentucky View My Personal Pix - 🀫  A sexy Crossdresser from Kentucky, 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...
  • Flawlessly gorgeous trans bombshell in KentuckyFlawlessly gorgeous trans bombshell in Kentucky Trans MtF for Man in Kentucky 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 ...
  • I’m a Sexy and Naughty T-Girl Here in Kentucky.I’m a Sexy and Naughty T-Girl Here in Kentucky. Kentucky T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Kentucky 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 ...
  • Tiffany Shelle - Your Kentucky Tranny Girlfriend! πŸ’žTiffany Shelle - Your Kentucky Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Kentucky It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functioni...
  • 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 Kentucky 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...
  • Kentucky Addicted to shemales... Male Seeking TSKentucky 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 ...