Hilo, Hawaii Shemale Dating Classifieds

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Show Ads In: Hilo | Honolulu

  • September 20th, 2026
  • MALE SEEKING SHEMALE 🍆Hilo Ready to Play and Fuck 💦MALE SEEKING SHEMALE 🍆Hilo 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 Hilo  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 and a...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hilo )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Hilo ) Sexy Crossdresser Elissa Looking for Hot Fun in Hilo💋    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 pre ...
  • I love a confident, seductive TS woman—could you be the one? 💋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,...
  • 👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥👑 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 ...
  • Flawlessly gorgeous trans bombshell in HiloFlawlessly gorgeous trans bombshell in Hilo Trans MtF for Man in Hilo 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 rece...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Hilo 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 als...
  • 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 Hilo area and are interested then drop me a line and introduce yourself. You can mes...
  • Sexy Shemale Hilo I know You Want to Play Sexy Shemale Hilo 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 Hilo; 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 kin...
  • 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 Hilo 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 nearb...
  • Hilo 😈🍆💦 Latina Shemale is Seeking a Real Man!! Hilo 😈🍆💦 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...
  • Transgender🟢TINA TS😉💋 Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Hilo 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.. Let's...
  • 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 Hilo 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 sexy, ...
  • Erotic exotic Asian queen in Hilo now (25)Erotic exotic Asian queen in Hilo now (25) Asian Transexual in Hilo 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....
  • 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  ...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Hilo I'm queen Delilah a trans woman here in Hilo 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 positions we c...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Hilo Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Hilo 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 a beauti...
  • Hilo Addicted to shemales... Male Seeking TSHilo 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 ...
  • Spicy 🌶  Latina Shemale in Hilo Ready to Fill You 😉😉 Spicy 🌶 Latina Shemale in Hilo 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 Hilo.  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 to h...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK 🍆😉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 m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Hilo 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...
  • Spicy and Hot T-Girl from ColombiaSpicy and Hot T-Girl from Colombia Latina T-Girl in Hilo Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
  • British T-girl Seeking Classy Gentleman in Hilo...British T-girl Seeking Classy Gentleman in Hilo... 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 Hilo and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exception...
  • New Body New MeNew Body New Me M2F post-op in Hilo 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 NatashaM2F...
  • 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...
  • 🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilo🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilo 🍑 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,...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Hilo 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 me ...
  • 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 Hilo 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 naughty ...
  • Seeking All TS Beauties in HiloSeeking All TS Beauties in Hilo  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...
  • HiloHilo's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Hilo Hi you sexy man! I'm Toni a trans woman from here in Hilo. 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 loves men. ...
  • 🍑 Your Secret Ebony Fantasy Is Just One Message Away 😜🍑 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...
  • Your Shemale Addiction 😈🥵 Starts NowYour Shemale Addiction 😈🥵 Starts Now Shemale Seeking Male.. Your Fantasy Starts Here 24yr old Transsexual/Shemale in Hilo 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 Pix an...
  • TS Beauties—Let’s Have Some REAL Fun! 😏🔥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...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Hilo 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 grow. ...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! HiloYOUR EBONY SHEMALE - big boobs and a BIG COCK! Hilo Hot Hot Hot! Sinead, a black shemale in Hilo ready to make all of your  wildest fantasies come true! 💋🔥 My Pictures and Profile! -- You want to find a sexy ebony shemale in  Hiloto fulfill all your dreams? Then stop searching because I am ready to make  all of your dreams come...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Hilo 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....
  • FtM seeking Princess Bride in HiloFtM seeking Princess Bride in Hilo FtM seeking Woman in Hilo Hi, I'm Andy, age 33, FtM transgender man living in Hilo. 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 @AndyFtM4Princes...
  • TS Beauties—Let’s Make Some Memories 💖✨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👄Hilo HawaiiTRANSGENDER👄Hilo Hawaii Transgender HOOKUPS IN Hilo Hawaii 🍆❤️😉  Check out My Profile and Pix HereI'm in Hilo Hawaii and I'm a ShemaleI also like to be known as a TGirl. Have you ever hooked up with a Transbefore? If not, I'd love to be your first.  🌈REAL Shemales LOVER 🌈LICKING AND S...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Hilo 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 come tru...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Hilo Look no further honey, I'm Franny an Ebony trans woman here in Hilo 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 to know a...
  • Email Local Shemales Now! 💌Email Local Shemales Now! 💌 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 😉.. Do you want to meet local shemales who want to fuck and have some sex...
  • Let’s Play a Game—Winner Gets Me 😉 Hilo Seeking!!Let’s Play a Game—Winner Gets Me 😉 Hilo Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Hilo 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's ow...
  • Flirty & Feminine CD Ready for Some Fun 💕😈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...
  • 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....
  • Let’s Get a Drink… and See Where It Leads 😘Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  HiloShemale 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 should...
  • Free Hawaii Transexuals GuideFree Hawaii Transexuals Guide Hawaii Transexuals Guide The Hawaii 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 Hawaii Transexuals Guide online.  Where to Meet Transexuals in Hawaii De...
  • 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 Hilo 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, pe...
  • Superb Shemale in Hilo...Superb Shemale in Hilo... T-Girl for NSA Encounters in Hilo When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Hilo. 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 and do all...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Hilo Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Hilo 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!  About me: 29 year...