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!

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

February 14th, 2026

Flirty & Feminine CD Ready for Some Fun 💕😈  I’m a sexy, smooth, and playful crossdresser who enjoys the attention, desiring  to be treated like a lady. Seeking for a man who can appreciate a well dressed CD for a  casual fun night or even something ongoing. I am a pleaser and I want to be pleased.  💋 💎 Bath g...

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 ...

💖 Discreet, Naughty & Waiting for a Man Who Can Handle Me  🔥 I’m an exotic ebony TS bombshell in Massachusetts 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’v...

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  ...

She-male looking for hot date to please. Asian Shemale in the Massachusetts 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...

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!  ...

I'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...

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...

Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Massachusetts Area Hi, my fem name is Gloria. I'm a married crossdresser in the Massachusetts area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross...

Black 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...

Seeking All TS Beauties in Massachusetts  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...

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...

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...

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...

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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 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...

Shy Transexual Escort in 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 ...

Flawlessly gorgeous trans bombshell in Massachusetts Trans MtF for Man in Massachusetts 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 ...

Shemale 4 Men 🍆💦 Massachusetts 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...

💦 Thick, Juicy & Kinky – Come Experience the Best 😏  🔥| 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 ...

Looking for a TS Woman Who Loves to Be Desired 💦🔥 Massachusetts  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. 💋 I would love to meet a shemale or tra...

🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Massachusetts 🍑 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,...

Don't Worry I Bite! Feisty redhead trans in Massachusetts 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 con...

YOUR 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! 💋🔥 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...

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! ...

One Night, No Rules, Just Pleasure… Massachusetts 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 cockt...

New Body New Me M2F post-op in Massachusetts 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...

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

Massachusetts'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 - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Massachusetts Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Massachusetts 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 On...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Massachusetts 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: Ga...

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 ...

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

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...

TS Beauties—Let’s Make Some Memories 💖✨  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...

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

Trans Playmate Sex Kitten... Ebony trans woman in Massachusetts 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....

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...

Hot Shemale in Massachusetts Ready to Fulfill Your Wildest Fantasies 👄💦🍆 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...

Massachusetts 😈🍆💦 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...

Sexy 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....

I’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...

Crystal, 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 ...

South Korean Shemale in Boston... Hi men, I am Ye-jun a sexy petite Asian shemale from Korea trained in the oriental art of seduction and pleasure. I am 24 years old, 5'4, 140 pounds, bottom. Pleasing you is number one responsibility. Treat me right and I will make you very happy and you will be back for more of Ye-jun company....

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...

Debonair 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...

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

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...

Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Massachusetts 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 say ...

MALE SEEKING SHEMALE 🍆Massachusetts 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 Massachusetts  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 he...