Hawaii Shemale Dating Classifieds

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Show Ads In: Hilo | Honolulu

September 21st, 2026

Email Hawaii Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...

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,...

Shemale 4 Men 🍆💦 Hawaii 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...

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Hawaii  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...

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

INTERACTIVE MAP: Transexual Tracker in the Hawaii Area! Local Transexual Hookups Meet local transexuals in the Hawaii 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 Hawaii Trans Hookups Map ...

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....

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...

Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Hawaii 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, ...

👑 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 ...

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! ...

Tantalizing Tina with a HUGE W33NAH! Hawaii Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Hawaii 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 ...

💖 Discreet, Naughty & Waiting for a Man Who Can Handle Me  🔥 I’m an exotic ebony TS bombshell in Hawaii 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 never...

Well Endowed Shemale is beautiful Hawaii 32 Well Endowed Shemale in Hawaii 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! ...

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

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

Latina TS Playmate – Sweet Accent, Dirty Thoughts 💃💋  You want flavor? Spice? A woman who can dance for you, then ride you like she  owns you? That’s me, papi 😘 I’m a curvy, high-femme  TS Latina with a pretty face, wild hips, and a very naughty surprise underneath. View My Latina TS Pictures - I love to  tease, fl...

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...

September 20th, 2026

MALE SEEKING SHEMALE 🍆Hawaii 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 Hawaii  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...

Hot Shemale in Hawaii Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Hawaii My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Hawaii 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 and having ...

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

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 🔥  🔥| 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 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 Hawaii area. Click here and come see me anytime!...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Hawaii Secret Crossdressing Hookups in Hawaii 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 gara...

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

Flawlessly gorgeous trans bombshell in Hawaii Trans MtF for Man in Hawaii 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 re...

Trans Playmate Sex Kitten... Ebony trans woman in Hawaii 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 a...

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 Hawaii area and are interested then drop me a line and introduce yourself. You can m...

Sexy Shemale Hawaii 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 Hawaii; 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 k...

TIFFANY TGIRL - Hawaii I'm a TGirl Living in Honolulu Hawaii ❤️😉  My Profile and Pix HereI'm in Honolulu Hawaii and I'm a TGirlI also like to be known as a Transgender. Have you ever hooked up with a Transbefore? If not, I'd love to be your first. You will love how feminine I am, even while hav...

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 Hawaii 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 nea...

Hawaii 😈🍆💦 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😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Hawaii 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...

Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Hawaii 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 Hawaii now (25) Asian Transexual in Hawaii 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....

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

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

I Need a Sexy Man to Tame Wild Willy! Hung Hawaii Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Hawaii 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 be...

Hawaii 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 Hawaii 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 Hawaii.  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...

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 here TS m/f Switch in Hawaii 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 Colombia Latina T-Girl in Hawaii 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 Hawaii... 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 Hawaii and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excepti...

New Body New Me M2F post-op in Hawaii 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 NatashaM...

TS Latina Seductress – Thick, Wet & Ready to Be Used 💋🍑  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...

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 😘 Hawaii 🍑 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,...