Massachusetts Shemale Dating Classifieds

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

  • November 12th, 2026
  • Superb Shemale in Massachusetts...Superb Shemale in Massachusetts... T-Girl for NSA Encounters in Massachusetts When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Massachusetts. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondl...
  • 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  ...
  • 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 Massachusetts 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...
  • Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina ๐Ÿ’‹ I'm in Massachusetts 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 no...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Massachusetts 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....
  • 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...
  • 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...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Massachusetts 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 ...
  • Latina TS Firestarter โ€“ I Donโ€™t Do โ€œMildโ€ ๐Ÿ”ฅ๐Ÿ‘ Latina TS Firestarter โ€“ I Donโ€™t Do โ€œMildโ€ ๐Ÿ”ฅ๐Ÿ‘  I’m your next obsession, papi ๐Ÿ˜˜ View More Pictures of Mine! TS. Latina. Voluptuous. Insatiable. And craving a man who can handle my curves, my tongue, and my need for deep, sweaty pleasure ๐Ÿ˜ˆ You’ll taste my perfume before I even touch you… and feel my body long after I lea...
  • TS Bombshell Looking for a Man Who Can Keep Up! ๐Ÿ’‹ MassachusettsTS Bombshell Looking for a Man Who Can Keep Up! ๐Ÿ’‹ Massachusetts  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures ๐Ÿ“ธ 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...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Massachusetts Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Massachusetts 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!  ...
  • 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 Massachusetts 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...
  • ๐Ÿ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure๐Ÿ‘„ Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  ๐Ÿ‘‘ I am the Queen of Your Fantasies – Come Worship Me! I am  a gorgeous, confident, ebony TS, with a body built for pleasure and a mind full of naughty  ideas. If you are looking for high class experience, filled with deep pleasure, seductive touches and  sensual moments...
  • Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Massachusetts Seeking!!Letโ€™s Play a Gameโ€”Winner Gets Me ๐Ÿ˜‰ Massachusetts 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...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Massachusetts.Iโ€™m a Sexy and Naughty T-Girl Here in Massachusetts. Massachusetts T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Massachusetts 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  wo...
  • TS Beautiesโ€”Letโ€™s Have Some REAL Fun! ๐Ÿ˜๐Ÿ”ฅTS Beautiesโ€”Letโ€™s Have Some REAL Fun! ๐Ÿ˜๐Ÿ”ฅ  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. ๐Ÿ’‹ Must  have confidence, charm...
  • TS Latina Fantasy Girl โ€“ Let Me Rock Your World ๐Ÿ’‹๐Ÿ”ฅTS Latina Fantasy Girl โ€“ Let Me Rock Your World ๐Ÿ’‹๐Ÿ”ฅ  Mira, papi… I’m not just sexy — I’m dangerous ๐Ÿ˜˜ ( 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...
  • 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 M...
  • 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....
  • MassachusettsMassachusetts's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Massachusetts Hi you sexy man! I'm Toni a trans woman from here in Massachusetts. 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, function...
  • Hot Shemale in Massachusetts Ready to Fulfill Your Wildest Fantasies ๐Ÿ‘„๐Ÿ’ฆ๐Ÿ†Hot Shemale in Massachusetts Ready to Fulfill Your Wildest Fantasies ๐Ÿ‘„๐Ÿ’ฆ๐Ÿ† I'm TS and Looking to Date in Massachusetts My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Massachusetts 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 peop...
  • Your Flirty CD Sweetheart Awaits ๐Ÿ’•๐Ÿ˜˜ MassachusettsYour Flirty CD Sweetheart Awaits ๐Ÿ’•๐Ÿ˜˜ Massachusetts 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. ๐Ÿ’‹ ๐Ÿ‘  Feminine, fun and ...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! MassachusettsYOUR EBONY SHEMALE - big boobs and a BIG COCK! Massachusetts Hot Hot Hot! Sinead, a black shemale in Massachusetts 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  Massachusettsto fulfill all your dreams? Then stop searching because I am ready to make  all o...
  • 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 Massachusetts 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 li...
  • Massachusetts ๐Ÿ˜ˆ๐Ÿ†๐Ÿ’ฆ Latina Shemale is Seeking a Real Man!! Massachusetts 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...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Massachusetts 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 ...
  • Marina TS ๐Ÿ† Visiting and ReadyMarina TS ๐Ÿ† 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...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Massachusetts 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 relations...
  • Shy Transexual Escort inย MassachusettsShy Transexual Escort inย Massachusetts 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 ...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in MassachusettsSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Massachusetts Secret Crossdressing Hookups in Massachusetts 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 priva...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Massachusetts I'm queen Delilah a trans woman here in Massachusetts 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 scandal...
  • Spicy ๐ŸŒถ  Latina Shemale in Massachusetts Ready to Fill You ๐Ÿ˜‰๐Ÿ˜‰ Spicy ๐ŸŒถ Latina Shemale in Massachusetts Ready to Fill You ๐Ÿ˜‰๐Ÿ˜‰ LATINA SHEMALE SEEKING ๐Ÿ”ฅ๐ŸŒถ  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Massachusetts.  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 l...
  • November 11th, 2026
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Massachusetts 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 i...
  • 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 ...
  • 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 ...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Massachusetts Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Massachusetts. 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 appre...
  • 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! ...
  • I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Massachusetts )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Massachusetts ) Sexy Crossdresser Elissa Looking for Hot Fun in Massachusetts๐Ÿ’‹    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 ...
  • Shemale 4 Men ๐Ÿ†๐Ÿ’ฆ  Massachusetts Ready Now!! Shemale 4 Men ๐Ÿ†๐Ÿ’ฆ Massachusetts 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...
  • British T-girl Seeking Classy Gentleman in Massachusetts...British T-girl Seeking Classy Gentleman in Massachusetts... 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 Massachusetts and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ...
  • 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 Massachusetts area and are interested then drop me a line and introduce yourself. Yo...
  • Hot sexy shemale doll visiting Massachusetts now Hot sexy shemale doll visiting Massachusetts now Shemale Visiting Massachusetts Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
  • Email Massachusetts Shemalesโค๏ธโ€๐Ÿ”ฅEmail Massachusetts Shemalesโค๏ธโ€๐Ÿ”ฅ 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...
  • TS Latina Snack โ€“ Sweet Like Sugar, Dirty Like Tequila ๐Ÿ˜˜๐ŸนTS Latina Snack โ€“ Sweet Like Sugar, Dirty Like Tequila ๐Ÿ˜˜๐Ÿน  You can find me at the bar where I serve drinks and flirt with customers while enjoying the  atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that  doesn’t stop until you beg me to ๐Ÿ’‹ I’ll start off sweet, flirty, &nbs...
  • 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....
  • Black BambiBlack Bambi's Got a BIG Love Gun and it's Loaded Baby! I shoot to thrill! Hey boys your gonna get more bang for your dating buck with BlackBambi in Boston! Don't go off half-cocked with those other trans women out there and be left wanting for more. I'm smokin' hot top or bottom. Love parties, events, traveling and the sexy choice for my horny boos ou...
  • ๐Ÿ–ค Ebony TS Playmate with a Curvy Body & a Wild Side ๐Ÿ˜˜ Massachusetts๐Ÿ–ค Ebony TS Playmate with a Curvy Body & a Wild Side ๐Ÿ˜˜ Massachusetts 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,...
  • One Night, No Rules, Just Pleasureโ€ฆ One Night, No Rules, Just Pleasureโ€ฆ Massachusetts 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 cockt...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Massachusetts 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 interestin...
  • Naughty boys check me out - Good thing I love naughty boys!Naughty boys check me out - Good thing I love naughty boys! Tiara here, I live to make your fantasies come true in Boston! I have a bubbly personality, enjoy intimate dinners, shopping, and I always give more than I receive. Fully passable, I dress to impress, STD free, classy, and ready to satisfy your needs and fetishes on short notice. I’m known for...