Hilton Head, South Carolina Shemale Dating Classifieds

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  • February 3rd, 2026
  • Having fun and Staying YoungHaving 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....
  • πŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilton HeadπŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilton Head πŸ‘ 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,...
  • 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...
  • 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 Hilton Head 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 live...
  • πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯πŸ‘‘ Chocolate Queen with Soft Curves & Naughty Desires πŸ”₯  πŸ”₯| 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 ...
  • 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 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...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Hilton Head. 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...
  • Shemale 4 Men πŸ†πŸ’¦  Hilton Head Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Hilton Head Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy ItπŸ˜‰   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...
  • Erotic exotic Asian queen in Hilton Head now (25)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....
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Hilton HeadYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ 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. πŸ’‹ πŸ‘  Feminine, fun and ...
  • 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 Hilton Head 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 insert...
  • 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  ...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Hilton Head 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 ...
  • Tantalizing Tina with a HUGE W33NAH!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 LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hilton Head )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hilton Head ) Sexy Crossdresser Elissa Looking for Hot Fun in Hilton HeadπŸ’‹    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 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 Hilton Head area and are interested then drop me a line and introduce yourself. You ...
  • πŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle MeπŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me  πŸ”₯ I’m an exotic ebony TS bombshell in Hilton Head with a love for steamy nights,  deep connections and uninhibited pleasure, keep it hot and wild and unforgettable! Whether you are looking for  an exciting adventure, a sensual night of passion or just something you’ve ...
  • INTERACTIVE MAP: Transexual Tracker in the Hilton Head Area!INTERACTIVE MAP: Transexual Tracker in the Hilton Head Area! Local Transexual Hookups Meet local transexuals in the Hilton Head area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Hilton Head Trans Hookups Map ...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Hilton Head 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....
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! Hilton HeadYOUR 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! πŸ’‹πŸ”₯ 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...
  • Selena Trans girl cute looking for loveSelena 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....
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Hilton HeadSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Hilton Head Secret Crossdressing Hookups in Hilton Head 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...
  • Sexy Shemale Hilton Head I know You Want to Play 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 ...
  • 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 H...
  • Tiffany Shelle - Your Hilton Head Tranny Girlfriend! πŸ’žTiffany Shelle - Your Hilton Head Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Hilton Head 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% functi...
  • TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘  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...
  • Flawlessly gorgeous trans bombshell in Hilton HeadFlawlessly 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...
  • Hot Shemale in Hilton Head Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ†Hot Shemale in Hilton Head Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ† 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...
  • British T-girl Seeking Classy Gentleman in Hilton Head...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...
  • New Body New MeNew 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...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! πŸ˜‰ 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 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...
  • Shy Transexual Escort inΒ Hilton HeadShy Transexual Escort inΒ Hilton Head 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 ...
  • MALE SEEKING SHEMALE πŸ†Hilton Head Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Hilton Head 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 Hilton Head  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 hear...
  • TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯  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. πŸ’‹ Must  have confidence, charm...
  • February 2nd, 2026
  • FtM seeking Princess Bride in Hilton HeadFtM seeking Princess Bride in Hilton Head FtM seeking Woman in Hilton Head Hi, I'm Andy, age 33, FtM transgender man living in Hilton Head. 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 @A...
  • πŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & PleasureπŸ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  πŸ‘‘ 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 Hilton HeadSeeking 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...
  • πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹  πŸ’– 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...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Hilton Head Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • M-F trans woman wants a dateM-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....
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.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...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Hilton Head 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 ...
  • Free South Carolina Transexuals GuideFree South Carolina Transexuals Guide South Carolina Transexuals Guide The South Carolina Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free South Carolina Transexuals Guide online.  Where to Meet T...
  • Hilton Head - TGIRL LOOKING FOR SEXHilton Head - TGIRL LOOKING FOR SEX Hilton Head, South CarolinaM-F Transgender Sex Tonight. Hilton Head, South Carolina - Tranny Sexting App  I'm a Transgender Mistress from Hilton Head, SC I've been here for years and I have a lot of sexy transgender friends here that want sex from men!!I think we should hookup ...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Hilton Head 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 relationshi...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Hilton Head 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...
  • Flirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆFlirty & Feminine CD Ready for Some Fun πŸ’•πŸ˜ˆ  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.  πŸ’‹ πŸ’Ž Bath g...
  • Looking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ Hilton HeadLooking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ 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. πŸ’‹ I would love to meet a shemale or tra...
  • One Night, No Rules, Just Pleasure… 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...