Hilton Head, South Carolina Shemale Dating Classifieds

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July 10th, 2025

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

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hilton Head ) Sexy Crossdresser Elissa Looking for Hot Fun in Hilton Head💋    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...

Tainted Love - Beyond Compare! Kinky Trans Woman in Hilton Head Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Hilton Head. 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 appreciat...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Hilton Head View My Personal Pix - 🤫  A sexy Crossdresser from Hilton Head, 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...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Hilton Head 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 ...

Hilton Head 😈🍆💦 Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking 🔥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...

Shemale 4 Men 🍆💦 Hilton Head 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...

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 Hilton Head tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer ...

Your Flirty CD Sweetheart Awaits 💕😘 Hilton Head 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 ...

New Body New Me M2F post-op in Hilton Head 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 Nat...

She-male looking for hot date to please. Asian Shemale in the Hilton Head Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them c...

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 Hilton Head area and are interested then drop me a line and introduce yourself. You ...

🍑 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...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Hilton Head 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...

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....

I’m a Sexy and Naughty T-Girl Here in Hilton Head. Hilton Head T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Hilton Head 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  worrie...

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...

👠 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...

Ebony Shemale in Hilton Head ❤️😘 Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies 💋 Are you looking for a hot and kinky black shemale in Hilton Head? 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...

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

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...

F/M seeking love and fun Female to Male Trans Man in Hilton Head 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...

Seeking All TS Beauties in Hilton Head  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...

Sexy Shemale Hilton Head 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 Hilton Head; 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 ...

British T-girl Seeking Classy Gentleman in Hilton Head... 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 Hilton Head and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ex...

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One Night, No Rules, Just Pleasure… Hilton Head 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 cocktai...

Flirty, Dirty, and Ready for Some Fun ❤️ Hilton Head 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...

👄 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...

Flawlessly gorgeous trans bombshell in Hilton Head Trans MtF for Man in Hilton Head 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 yo...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Hilton Head 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: Gayl...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Hilton Head AREA Hi baby! I am waiting to meet you. I can host or travel to you. Down to earth preop transexual woman seeking an understanding man who can appreciate my uniqueness. I am a great cook and great fun! Let your hair down and allow me to pamper you! Private Mess...

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

TS Latina Fantasy Girl – Let Me Rock Your World 💋🔥  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...

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

Beautiful Krystale 25 Hilton Head visiting now Beautiful Shemale Visiting Hilton Head 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: Hilton Head Sex: Shemale Seeking: Man ...

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,...

🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilton Head 🍑 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,...

Spicy 🌶 Latina Shemale in Hilton Head 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 Hilton Head.  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 lov...

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...

Erotic exotic Asian queen in Hilton Head now (25) Asian Transexual in Hilton Head 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....

Hot Shemale in Hilton Head Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Hilton Head My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Hilton Head who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some like minded people a...

YOUR EBONY SHEMALE - big boobs and a BIG COCK! Hilton Head Hot Hot Hot! Sinead, a black shemale in Hilton Head ready to make all of your  wildest fantasies come true! 💋🔥 My Pictures and Profile! -- You want to find a sexy ebony shemale in  Hilton Headto fulfill all your dreams? Then stop searching because I am ready to make  all of yo...

Tantalizing Tina with a HUGE W33NAH! Hilton Head Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Hilton Head men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  Abo...

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

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Hot TS Latina with Curves, Sass, and a Thirst for You 😘🍷  You are not the typical girl who lives in the next house… You are the woman who occupies  your thoughts when you are with the woman who lives next door.  Message me here!! I’m a TS Latina goddess —  I have the shape of a coke bottle, the lips of sin, and a t...

Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  Hilton HeadShemale Seeking Man for sex💦 View More of My Pix - ✅ 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...

👑 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 ...