Hilo, Hawaii Shemale Dating Classifieds

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Show Ads In: Hilo | Honolulu

  • November 1st, 2025
  • I want to be a whoreI 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 Hilo area. Click here and come see me anytime!...
  • 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....
  • 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...
  • Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Hilo Seeking!!Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Hilo Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. ๐Ÿ˜ 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...
  • ๐Ÿ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me๐Ÿ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me  ๐Ÿ”ฅ I’m an exotic ebony TS bombshell in Hilo 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 d...
  • Hilo ๐Ÿ˜ˆ๐Ÿ†๐Ÿ’ฆ Latina Shemale is Seeking a Real Man!! Hilo ๐Ÿ˜ˆ๐Ÿ†๐Ÿ’ฆ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking ๐Ÿ”ฅReady 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...
  • Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina ๐Ÿ’‹ 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...
  • Shy Transexual Escort inย HiloShy Transexual Escort inย Hilo 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 ...
  • Looking for My TS Queen ๐Ÿ‘‘๐Ÿ’‹Looking for My TS Queen ๐Ÿ‘‘๐Ÿ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. ๐Ÿ’• 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,...
  • TS Beautiesโ€”Letโ€™s Make Some Memories ๐Ÿ’–โœจTS Beautiesโ€”Letโ€™s Make Some Memories ๐Ÿ’–โœจ  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...
  • ๐Ÿ‘‘ Chocolate Queen with Soft Curves & Naughty Desires ๐Ÿ”ฅ๐Ÿ‘‘ Chocolate Queen with Soft Curves & Naughty Desires ๐Ÿ”ฅ  ๐Ÿ”ฅ| 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 ...
  • 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...
  • INTERACTIVE MAP: Transexual Tracker in the Hilo Area!INTERACTIVE MAP: Transexual Tracker in the Hilo Area! Local Transexual Hookups Meet local transexuals in the Hilo 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 Hilo Trans Hookups Map ...
  • ๐Ÿ–ค Ebony TS Playmate with a Curvy Body & a Wild Side ๐Ÿ˜˜ Hilo๐Ÿ–ค Ebony TS Playmate with a Curvy Body & a Wild Side ๐Ÿ˜˜ Hilo ๐Ÿ‘ 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,...
  • Shemale 4 Men ๐Ÿ†๐Ÿ’ฆ  Hilo Ready Now!! Shemale 4 Men ๐Ÿ†๐Ÿ’ฆ Hilo Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy It๐Ÿ˜‰   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...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Hilo Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Hilo. 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 brin...
  • 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...
  • 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....
  • Well Endowed Shemale is beautiful Hilo 32Well Endowed Shemale is beautiful Hilo 32 Well Endowed Shemale in Hilo 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!  ...
  • 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...
  • ๐Ÿ’ฆ Thick, Juicy & Kinky โ€“ Come Experience the Best ๐Ÿ˜๐Ÿ’ฆ Thick, Juicy & Kinky โ€“ Come Experience the Best ๐Ÿ˜  ๐Ÿ”ฅ| 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 ...
  • 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. ...
  • 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...
  • TS Latina Seductress โ€“ Thick, Wet & Ready to Be Used ๐Ÿ’‹๐Ÿ‘TS Latina Seductress โ€“ Thick, Wet & Ready to Be Used ๐Ÿ’‹๐Ÿ‘  Papi… I’ve been thinking about you ๐Ÿ˜˜ 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 ๐Ÿ˜ˆ. I become  submissive only when you want me to submit while I transform into a dominant forc...
  • 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...
  • 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! ๐Ÿ’‹๐Ÿ”ฅ 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...
  • 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...
  • I Need a STEAM ROLLER Baby!!!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 ...
  • TRANSGENDER๐Ÿ‘„Hilo HawaiiTRANSGENDER๐Ÿ‘„Hilo Hawaii Transgender HOOKUPS IN Hilo Hawaii ๐Ÿ†โค๏ธ๐Ÿ˜‰  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.  ๐ŸŒˆREAL Shemales LOVER ๐ŸŒˆLICKING AND S...
  • ๐Ÿ‘ Your Secret Ebony Fantasy Is Just One Message Away ๐Ÿ˜œ๐Ÿ‘ Your Secret Ebony Fantasy Is Just One Message Away ๐Ÿ˜œ  ๐Ÿ‘„ 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...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Hilo? Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Hilo.Iโ€™m a Sexy and Naughty T-Girl Here in Hilo. Hilo T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Hilo 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 stress o...
  • Hot Shemale in Hilo Ready to Fulfill Your Wildest Fantasies ๐Ÿ‘„๐Ÿ’ฆ๐Ÿ†Hot Shemale in Hilo Ready to Fulfill Your Wildest Fantasies ๐Ÿ‘„๐Ÿ’ฆ๐Ÿ† I'm TS and Looking to Date in Hilo My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Hilo 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 fun....
  • Dr FreakinDr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Hilo area come see if you measure up! Click here for explicit photos. Look for ...
  • 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. ...
  • Tiffany Shelle - Your Hilo Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Hilo Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Hilo It’s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGIT โœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functioning s...
  • 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...
  • 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...
  • TS Latina Bombshell โ€“ Your Secret Addiction, Your Midnight Obsession ๐Ÿ˜ˆ๐Ÿ‘TS Latina Bombshell โ€“ Your Secret Addiction, Your Midnight Obsession ๐Ÿ˜ˆ๐Ÿ‘  Hola, mi amor ๐Ÿ˜˜ 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...
  • 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, ...
  • October 31st, 2025
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in HiloSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Hilo Secret Crossdressing Hookups in Hilo 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 garage...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Hilo 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 Message @El...
  • 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...
  • 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...
  • 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 Hilo๐Ÿ’‹    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 ...
  • 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....
  • One Night, No Rules, Just Pleasureโ€ฆ One Night, No Rules, Just Pleasureโ€ฆ Hilo I'm Having a Night to Myself No Strings, just fun.. TS Seeking...๐Ÿคซ  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 cocktails. I t...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK ๐Ÿ†๐Ÿ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK ๐Ÿ†๐Ÿ˜‰ BBC SHEMALE - BLACK TRANS๐Ÿ’Ž 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...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! ๐Ÿ˜‰ 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...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Hilo 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: GayleTGirl ...