Boston Transgender Classifieds
Browse Boston transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!
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Show Ads In: Boston | Cape Cod / Islands | South Coast | Western MA | Worcester / Central MA
- June 30th, 2026
🔥 Sexy Trans Beauty in Boston – Let’s Play 😘 🔥 I’m a confident, flirty trans woman looking for a naughty, open-minded man who knows how to have a good time. I require someone who lives near me to establish genuine emotional bonds through playful games while they disclose their sexual interests to me 😈. waiting for your message babe!!
I...
Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Boston Area
Hi, my fem name is Gloria. I'm a married crossdresser in the Boston area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but my wife doesn't approve. I REALLY need to let my fem side out to play!
I'm seeking cross dressing f...
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Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight?
Hi babe, I'm Tina 💋 I'm in Boston 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...
I’m a Sexy and Naughty T-Girl Here in Boston. Boston T-Girl 4 NSA
Fabulous Fanny here boys! I'm a trans woman living in the Boston 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 worries and stre...
Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Boston
Look no further honey, I'm Franny an Ebony trans woman here in Boston 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 and they don't have to kn...
Road Head Sally Drivin' Hard in Boston Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Boston. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park ...
Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠 Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here -
As a TS darling I present like a dream while playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a throbbing surprise you’ll love exploring 😘 I need you to undress me gr...
Cute TS Sugar Baby Seeking Male💎Aria Username: @AriaSweet
Trans Friendly: Yes
Private Meetups: Yes
Phone Chat: Yes
Pics Available: 18
Message me if you like feminine Transsexual 💬
Hello, I am AriaTS here in Boston. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a man th...
Road Head Sally Drivin' Hard in Boston Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Boston. Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or park at some of our favorite spots for some intimacy and sexual relief. Come on o...
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....
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Boston?
Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sorts o...
Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice!
Hey boys, my name is LethaWeapon here in Boston 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, ...
Elisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Boston 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 and show you what ...
I Need a Sexy Man to Tame Wild Willy! Hung Boston Trans Woman
Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Boston 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 be...
TS Tina – Your Seductive Fantasy in Boston 🔥 Your dream TS girl Tina has arrived to create a hot experience while she will help you discover your most intense sexual fantasies. I create a perfect combination of wild and warm sensations through my soft touch and my playful nature. I find men who understand how to handle a woman with confidence ...
Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Boston area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3
Username: @Crystal27transLocation: Boston, MassachusettsAge...- June 29th, 2026
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 Boston area and are interested then drop me a line and introduce yourself. You can m...
Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Boston for Man
Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will be pro...
Sexy hung and big busted Hung and Busty Shemale in Boston
Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine.
Username: @Tammy39TLocation: Boston, MassachusettsAge:...
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋 📍 Location: Boston
💖 Seeking: Fun, Exciting, & Discreet Connections
Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I'm ...
Beautiful Krystale 25 Boston visiting now Beautiful Preop Shemale Visiting Boston
Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me @Krystale25shemale.
Krystale25shemale
Username: @Krystale25shemale
Age: 25
Location: Boston, Massachusetts
Sex: MtF Trans
Seeking: Man
...
Hot sexy shemale doll visiting Boston now Shemale Visiting Boston
Very hot sevy and curvy shemale chick with big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1.
Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible long te...
Exotic TS Beauty Seeking a Generous Gentleman 🔥💎 Hello lovely, I’m a beautiful trans girl with lots of curves. I’m a confident woman with a beautiful personality. Here I want to meet with the more successful men. Men who can understand that the beauty is also of the feminine kind. Intelligent men, that can realize that we trans girls 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 Boston tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer than ...
Hookup With Boston TS Sugar Baby Now! 💌 Want to Hookup and Find Boston Shemales? RADE PIX - MESSAGE - BROWSE PROFILES
This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you're interested in 😉.. Do you want to meet local shemales who want to fuck and have some sexy fun? I dare...
💕 Boston Trans Sugar Baby Seeking Connection, Consistency & Care Hey Boston 💋Feminine in feel, confident in who I am - this TS sugar baby moves through days with steady calm. Evenings spent at soft tables in the Back Bay draw me in, where talk flows slow and space feels wide. When dusk arrives, walking paths begin to empty; then the town breathes differently. ...
Luxury Ebony TS Sugar Baby With Style 👠💎 Hello handsome… I am a ebony trans sugar baby, a beautiful, classy and elegant young lady. I look for confident men that are also very kind to women and who like to spoil a gorgeous lady. Fashion, food and especially great chemistry are my top priorities. let's plan our play date.
I love peo...
Hot trans chick with nice boobs Hot trans chick in Boston. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want to ...
Ebony TS Playmate for Men Who Know What They Want 🖤🍆 If you are the type of person who does not want to waste time with games or small talk… we are already off to a good start 😘
I am a sexy, curvy TS babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like a dream and be read...
Strict Shemale Dominatrix in Boston - @DesireeTransDomme Powerful African-Queen Dominatrix in Boston
I am full-time professional Domme Desiree. My Boston area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you will learn to s...
Free Massachusetts Transexuals Guide Massachusetts Transexuals Guide
The Massachusetts Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free Massachusetts Transexuals Guide online.
Where to Meet Tran...
Superb Shemale in Boston... T-Girl for NSA Encounters in Boston
When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Boston. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and do...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Boston! LET'S TAKE CARE OF THAT TRANNY FANTASY!
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Shemale Gia's Boston Sexbook @ShemaleGia27
Photos: 44
Vid...
I'm the Girl Your Mum 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 Boston 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 nea...
Tainted Love - Beyond Compare! Kinky Trans Woman in Boston
Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Boston. 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 ...
Glamorous TS Sugar Baby Ready to Be Spoiled 💎💋 Hi handsome… I’m a beautiful trans sugar baby that loves the luxuries in life and I’m searching for a confident man who will treat me like the queen I am. I am very soft and feminine with a playful edge and you will always have a smile on your face when we talk. View My TS Sugar B...
Transgender Goddess for Late-Night Escapes & Filthy Fun 🌙💋 It’s late. You’re restless. And you’re craving something… different 😏 - View My Transsexual Dating Profile -
As your TS fantasy girl I offer sultry and smooth vibes while delivering experiences beyond what your ex could have imagined. My secret between...
Tiffany Shelle - Your Boston Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Boston
It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!
I'm 100% functioning...
Trans Woman with Superpowers! What's your superpower baby? Show me yours and I'll show you mine. I'm Scarlett a trans woman here in Boston with the power to make your dreams cum true. I'm sweet, sexy, affectionate, with a big surprise and want you to have your way with me tonight. Don't be shy, this is all about our primal insti...
Dr 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 Boston area come see if you measure up! Click here for explicit photos. Look fo...
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...
Boston💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘
I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
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...
Selena 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 @SelenaIsTrans and send me a message to set up a date.
I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...- June 28th, 2026
Boston's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Boston
Hi you sexy man! I'm Toni a trans woman from here in Boston. 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, functional and loves m...
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 ...
Trans Sugar Baby Energy in Boston - I'm ready for a night out! Hey there… I’m a sweet, confident, and playful trans beauty in my early 20s who loves good vibes, strong chemistry, and nights that turn into stories you replay later 😘 I enjoy being admired, feeling cared for, and bringing a little sparkle wherever I go. Yes, I can be your “ba...
💎 Confident TS Sugar Baby in Boston 💎 I enter any space with my confident trans woman presence which immediately makes me the center of attention. I find great happiness when people express their admiration and appreciation for me while they actively provide me with care. I find complete happiness when someone else handles everything be...
🔥 TS Yessica – Verified & Ready in Boston 🔥 TS Yessica shows her confident and playful personality when she meets new people because she shows them her authentic self. 😘 You have discovered your perfect trans escort who will create unforgettable experiences while providing an outstanding encounter. I dedicate my free time to people who gen...