Kentucky Shemale Dating Classifieds

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

March 23rd, 2026

Superior Massage by gorgeous T-Girl T-Girl for Dating in Kentucky 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...

Trans Playmate Sex Kitten... Ebony trans woman in Kentucky 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...

THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! 😉 My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...

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...

Shy Transexual Escort in 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 ...

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'...

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 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...

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

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! ...

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| 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 ...

YOUR 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! 💋🔥 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...

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

March 22nd, 2026

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...

Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Kentucky 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 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...

Penny for your thoughts? Penny TS in Kentucky Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online!! I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting hit...

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Kentucky Look no further honey, I'm Franny an Ebony trans woman here in Kentucky 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...

Well 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...

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 ...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Kentucky Secret Crossdressing Hookups in Kentucky 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 ga...

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

Shemale 4 Men 🍆💦 Kentucky 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...

Flirty, Dirty, and Ready for Some Fun ❤️ Kentucky Shemale Seeking Male Local Shemale Seeks Man For Adventure!  TS Vixen, are you ready to play? Sweet, sultry and a little bit  wild, I am a trans goddess and I do enjoy my men to be as much as a wild  as I am. 😘I don’t want to talk – I want to try something a bit  more exciting. How ab...

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...

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...

F/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...

🍑 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...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Kentucky Hey! Thanks for looking at my ad. This is the first time I've done this so bear with me plz. I am Jared, FtM trans man. I transitioned at age 25 and I just turned 30. Come and meet me!  Check my personal profile @FtMJared29 and say hi!&n...

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...

MALE SEEKING SHEMALE 🍆Kentucky 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 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...

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 Kentucky area. Click here and come see me anytime!...

LOUISVILLE😈TRANNY SEX I'm a Sexy Shemale LIVINGIN Louisville, Kentucky ❤️😉 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 ...

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...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Kentucky Area Hi, my fem name is Gloria. I'm a married crossdresser in the Kentucky 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 ...

💦 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 ...

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

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

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Kentucky  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures 📸 Are you the sort of man who enjoys  just a touch of danger, a touch of excitement, and a lot of passion? I’m the  trans beauty you’ve been dreaming of — sexy...

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....

M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....

👑 TS Ebony Goddess Looking for Her King Tonight 🔥  🍫 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 ...

Flirty & Feminine CD Ready for Some Fun 💕😈  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  💋 💎 Bath g...

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...

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

Sassy CD Looking for a Real Man 😘🔥  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...

👄 Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  👑 I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...

Seeking All TS Beauties in Kentucky  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...

Debonair 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.&...

March 21st, 2026

Beautiful Krystale 25 Kentucky visiting now Beautiful Shemale Visiting Kentucky Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Kentucky Sex: Shemale Seeking: Man ...