Cape Cod / Islands, Massachusetts Shemale Dating Classifieds

Cape Cod / Islands, Massachusetts shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!

Home / Shemale Dating /

Show Ads In: Boston | Cape Cod / Islands | South Coast | Western MA | Worcester / Central MA

  • 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 Cape Cod / Islands Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Cape Cod / Islands 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 favorit...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Cape Cod / Islands Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Cape Cod / Islands Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Cape Cod / Islands 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 Cape Cod / Islands 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 w...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Cape Cod / Islands )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Cape Cod / Islands ) Sexy Crossdresser Elissa Looking for Hot Fun in Cape Cod / IslandsπŸ’‹    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 a...
  • Seeking All TS Beauties in Cape Cod / IslandsSeeking All TS Beauties in Cape Cod / Islands  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 Cape Cod / Islands Area!INTERACTIVE MAP: Transexual Tracker in the Cape Cod / Islands Area! Local Transexual Hookups Meet local transexuals in the Cape Cod / Islands 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 Cape Cod / Islands Trans Hookups Map ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Cape Cod / Islands Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Cape Cod / Islands to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enj...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Cape Cod / Islands Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Cape Cod / Islands 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 ...
  • Shy Transexual Escort inΒ Cape Cod / IslandsShy Transexual Escort inΒ Cape Cod / Islands 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...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Cape Cod / IslandsYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Cape Cod / Islands 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 😘 Cape Cod / IslandsπŸ–€ Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Cape Cod / Islands 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 Cape Cod / Islands 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 Cape Cod / Islands 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...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Cape Cod / Islands 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 ...
  • Erotic exotic Asian queen in Cape Cod / Islands now (25)Erotic exotic Asian queen in Cape Cod / Islands now (25) Asian Transexual in Cape Cod / Islands 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,...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Cape Cod / Islands Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Cape Cod / Islands. 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...
  • 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...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Cape Cod / Islands 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 Cape Cod / Islands View My Personal Pix - 🀫  A sexy Crossdresser from Cape Cod / Islands, 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 ...
  • 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 Cape Cod / Islands area and are interested then drop me a line and introduce yoursel...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Cape Cod / Islands Look no further honey, I'm Franny an Ebony trans woman here in Cape Cod / Islands 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 a...
  • 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...
  • Tiffany Shelle - Your Cape Cod / Islands Tranny Girlfriend! πŸ’žTiffany Shelle - Your Cape Cod / Islands Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Cape Cod / Islands 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%...
  • Superb Shemale in Cape Cod / Islands...Superb Shemale in Cape Cod / Islands... T-Girl for NSA Encounters in Cape Cod / Islands When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Cape Cod / Islands. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to fl...
  • TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨  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...
  • 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 ...
  • Well Endowed Shemale is beautiful Cape Cod / Islands 32Well Endowed Shemale is beautiful Cape Cod / Islands 32 Well Endowed Shemale in Cape Cod / Islands 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 m...
  • New Body New MeNew Body New Me M2F post-op in Cape Cod / Islands 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&n...
  • 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....
  • Cape Cod / IslandsCape Cod / Islands's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Cape Cod / Islands Hi you sexy man! I'm Toni a trans woman from here in Cape Cod / Islands. 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...
  • 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 Cape Cod / Islands 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...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Cape Cod / Islands I'm queen Delilah a trans woman here in Cape Cod / Islands 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 a...
  • I’m a Sexy and Naughty T-Girl Here in Cape Cod / Islands.I’m a Sexy and Naughty T-Girl Here in Cape Cod / Islands. Cape Cod / Islands T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Cape Cod / Islands 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 you...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Cape Cod / IslandsSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Cape Cod / Islands Secret Crossdressing Hookups in Cape Cod / Islands 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 ...
  • 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 Cape Cod / Islands 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 n...
  • Shemale 4 Men πŸ†πŸ’¦  Cape Cod / Islands Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Cape Cod / Islands 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...
  • Marina TS πŸ† Visiting and ReadyMarina TS πŸ† Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...
  • British T-girl Seeking Classy Gentleman in Cape Cod / Islands...British T-girl Seeking Classy Gentleman in Cape Cod / Islands... 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 Cape Cod / Islands and am financially independent and looking for a gentleman who is like-minded, equally solvent and...
  • DonDon't Worry I Bite! Feisty redhead trans in Cape Cod / Islands 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 t...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Cape Cod / Islands 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 Usernam...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Cape Cod / Islands 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 gr...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Cape Cod / Islands 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 rela...
  • Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯Seeking a Stunning TS for Passion & Pleasure 😘πŸ”₯  I am a confident, strong and open minded man, who knows what I want from a woman  – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to  explore and enjoy every second of it, whether it is a casual hookup, a fun date or a  deep connect...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Cape Cod / Islands 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...