Kentucky Shemale Dating Classifieds

Kentucky 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: Bowling Green | Huntington-Ashland | Lexington | Louisville | Western KY

May 8th, 2026

🍑 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...

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 ...

Looking for My TS Queen 👑💋 I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. 💕 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,...

Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too. See my pictures and send message for date....

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...

I love a confident, seductive TS woman—could you be the one? 💋  A handsome, intelligent and adventurous man, here looking to meet a gorgeous TS woman to have  excitement, chemistry and wild nights. I just love confident women who know what they want and I’m more  than ready to spoil, explore and indulge in pleasure together.  Handsome,...

I'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...

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 ...

Spicy 🌶 Latina Shemale in Kentucky Ready to Fill You 😉😉 LATINA SHEMALE SEEKING 🔥🌶  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 ...

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...

Flawlessly 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 ...

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....

Superb Shemale in Kentucky... T-Girl for NSA Encounters in Kentucky When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Kentucky. 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...

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  ...

Brandi 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...

BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK 🍆😉 BBC SHEMALE - BLACK TRANS💎 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...

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 💋 I’ll start off sweet, flirty, &nbs...

T-Girl Leah the Pride of Louisville Baby! Hi gents I'm Leah a trans woman in Louisville ready for some hot action. I'm looking for a local man who is interested in maybe a regular hookup if the chemistry is right. I'm functional, passible, hung, uncut, blonde, blue eyes and horny AF baby! I host, or we go out, or your place is also good. I ...

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...

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'...

Local Crossdresser 😉😇 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...

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 ...

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...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Kentucky 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...

Kentucky'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...

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 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!...

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....

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...

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...

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...

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.&...

Sexy hung and big busted Hung and Busty Shemale in Kentucky Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....

Kentucky 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 ...

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...

TS Latina Dream Girl – Ride Me Like a Telenovela 😈📺  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...

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...

🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Kentucky 🍑 Thick thighs, soft lips, and a wild side—what more could you want? I’m a sensual, passionate ebony TS beauty who knows how to make a man feel special, desired, and completely satisfied. Whether we take it slow and intimate or dive into a steamy, no-strings-attached night of passion,...

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...

Latina TS Firestarter – I Don’t Do “Mild” 🔥👠 I’m your next obsession, papi 😘 View More Pictures of Mine! TS. Latina. Voluptuous. Insatiable. And craving a man who can handle my curves, my tongue, and my need for deep, sweaty pleasure 😈 You’ll taste my perfume before I even touch you… and feel my body long after I lea...

Marina TS 🍆 Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...

Your Flirty CD Sweetheart Awaits 💕😘 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. 💋 👠 Feminine, fun and ...

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...

May 7th, 2026

Hot trans chick with nice boobs Hot trans chick in Kentucky. 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...

Your Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Kentucky seeking some fun and campanionship. I would like hookups and I'm also wanting love. I think we should play some plans and see what we can come up with.. I'm open minded and ready!! Take a min to View my Pi...

👑 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 ...

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 ...

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...

👠 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...

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...