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

April 3rd, 2025

TS m/f switch 28 new here TS m/f Switch in Massachusetts 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...

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...

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...

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 ...

I 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 Massachusetts area. Click here and come see me anytime!...

TS Latina Seductress – Thick, Wet & Ready to Be Used 💋🍑  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...

TS Latina Fantasy Girl – Let Me Rock Your World 💋🔥  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...

Funky Worcester Chick With a Big... Hi boys I'm FunkyChick here in Worcester bout ta take ya to funky town tonight. Let's get funked up honey and let me show you what's up in FunkyChick's world. Sure, I'm a little wild and crazy, but common, I know you have a crazy kinky side too? Am I right? Let's join forces and see how funked up we...

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...

April 2nd, 2025

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...

FtM seeking Princess Bride in Massachusetts FtM seeking Woman in Massachusetts Hi, I'm Andy, age 33, FtM transgender man living in Massachusetts. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message&nbs...

Email Massachusetts Shemales❤️‍🔥 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...

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...

Your Flirty CD Sweetheart Awaits 💕😘 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. 💋 👠 Feminine, fun and ...

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...

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....

TS Beauties—Let’s Have Some REAL Fun! 😏🔥  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. 💋 Must  have confidence, charm...

Upscale T-Girl in Boston Seeking Gentlemen of Taste for Fun... Hello gentlemen, I'm Aspen a t-girl for discerning men who need refined feminine company in public and wild sexual encounters in private. As you might expect I am all you need to satisfy your trans fantasy and make it come true. Whether it's your first time or not I'll make you comfortable and move ...

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...

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 Massachusetts tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longe...

Beautiful Krystale 25 Massachusetts visiting now Beautiful Shemale Visiting Massachusetts Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.  Krystale25shemale Age: 25 Location: Massachusetts Sex: Shemale Seeking: Man ...

Sassy CD Looking for a Real Man 😘🔥  A sweet, sexy and a little naughty crossdresser here, I like to play and  flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing  up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me  and y...

Well Endowed Shemale is beautiful Massachusetts 32 Well Endowed Shemale in Massachusetts 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 siz...

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 ...

HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Massachusetts! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Massachusetts!  No strings - just great times, so join my page free for instant access! Shemale Gia's Massachusetts Sexbook @ShemaleGia27 P...

TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession 😈🍑  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...

Sexy Shemale Massachusetts 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 Massachusetts; 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 ho...

Black Boston Trans Hottie Wants to Freak You Tonight!... Hey boys I'm Dotty a black trans women in Boston and at large again after a short time away. I missed y'all, my batteries are recharged and it's good to be back! Who's up for some hot action? As always I'm up for whatever you want and need. Discreet, hung, friendly and passionate. Message Dotty...

!!!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...

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...

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...

Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Massachusetts 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 Me...

THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! 😉 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...

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 ...

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....

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...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 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...

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...

TS Bombshell Looking for a Man Who Can Keep Up! 💋 Massachusetts  Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun! View More of My Pictures 📸 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! 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!  ...

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...

Spicy 🌶 Latina Shemale in Massachusetts Ready to Fill You 😉😉 LATINA SHEMALE SEEKING 🔥🌶  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...

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...

👄 Dark-Skinned TS Beauty Looking for Fun, Passion & Pleasure  👑 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...

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...

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...

💦 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 ...

TRANSGENDER LADY❤️sexy hookups Transgender HOOKUPSin BOSTON MASSACHUSETTS   Direct Message MeI'm in the Boston Massachusetts.. area. I'm willing to travel. As longas you love TRANSSEXUALS.. I want toshow you my Tranny peepee and I wantto see yours. What would you do with my cock right this second babe? I know...

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...