Hilo, Hawaii Shemale Dating Classifieds

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Show Ads In: Hilo | Honolulu

  • May 7th, 2026
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Hilo. 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...
  • 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...
  • Transgender🟒TINA TSπŸ˜‰πŸ’‹ Transgender🟒TINA TSπŸ˜‰πŸ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina πŸ’‹ 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...
  • One Night, No Rules, Just Pleasure… One Night, No Rules, Just Pleasure… Hilo 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 cocktails. I t...
  • 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! πŸ’‹πŸ”₯ 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 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!...
  • 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...
  • Hilo πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Hilo πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯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...
  • 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...
  • 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...
  • 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 ...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰ BBC SHEMALE - BLACK TRANSπŸ’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...
  • 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...
  • Looking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ HiloLooking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ Hilo  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...
  • 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...
  • Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹Latina TS Playmate – Sweet Accent, Dirty Thoughts πŸ’ƒπŸ’‹  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...
  • 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...
  • 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. ...
  • πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best πŸ˜πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best 😏  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 ...
  • Do you know the difference between a dick and a bucket of popcorn?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 Hilo tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than a ...
  • 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 ...
  • May 6th, 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....
  • 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...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Hilo Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Hilo Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ 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...
  • 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...
  • 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...
  • 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 HiloπŸ’‹    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 ...
  • 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...
  • 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 ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Hilo Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Hilo to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enjoy 24/7 Online Chat Make Se...
  • 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...
  • TRANSGENDERπŸ‘„Hilo HawaiiTRANSGENDERπŸ‘„Hilo Hawaii Transgender HOOKUPS IN Hilo Hawaii πŸ†β€οΈπŸ˜‰  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...
  • Shy Transexual Escort inΒ HiloShy Transexual Escort inΒ 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 ...
  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  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...
  • 🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 πŸ’– Hey, Handsome! I’m a sultry, curvy ebony TS  here in Hilo... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! 😘 I'm writing this to see...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ HiloYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Hilo 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 ...
  • πŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 HiloπŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Hilo 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 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...
  • 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...
  • 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...
  • 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....
  • Looking for My TS Queen πŸ‘‘πŸ’‹Looking for My TS Queen πŸ‘‘πŸ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. πŸ’• 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 Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“ΊTS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“Ί  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...
  • 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...
  • Hi Guys!! I am looking for someone fun!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! ...
  • πŸ‘ Your Secret Ebony Fantasy Is Just One Message Away πŸ˜œπŸ‘ Your Secret Ebony Fantasy Is Just One Message Away 😜  πŸ‘„ 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...
  • Spicy 🌢  Latina Shemale in Hilo Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Hilo Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  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...
  • 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....
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Hilo View My Personal Pix - 🀫  A sexy Crossdresser from Hilo, 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 lot...