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
- January 15th, 2026
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 B...- January 14th, 2026
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...
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...
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 ...
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...
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 ...
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 ...
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...
Erotic exotic Asian queen in Boston now (25) Asian Transexual in Boston
Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Longter...
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...
British T-girl Seeking Classy Gentleman in Boston... 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 Boston and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excepti...
Trans Playmate Sex Kitten... Ebony trans woman in Boston 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. I am a...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Boston
Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
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...
Email Boston Shemales 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...
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...
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...
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....
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...
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...
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Boston 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'm sexy...
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...
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...
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 ...
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'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World!
Local Transsexual - TGIRL Sext App 📲
I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...- January 13th, 2026
Tantalizing Tina with a HUGE W33NAH! Boston Trans Woman for Hookup!
Hey gents I'm Tina a trans female hot for all you sexy Boston 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!
About me: 29 ...
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Well Endowed Shemale is beautiful Boston 32 Well Endowed Shemale in Boston
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 @BlancaShemale32 with your recent pic or selfie for my latest pictures and pro...
Trans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Boston
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 hi!&nbs...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Boston! 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 Boston! No strings - just great times, so join my page free for instant access!
Shemale Gia's Boston Sexbook @ShemaleGia27
Photos: 42
Vid...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Boston
I'm queen Delilah a trans woman here in Boston 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 scandalous positions ...
New Body New Me M2F in Boston
Hi, I'm Natasha, newly transitioned, exploring this beautiful new chapter in my life, and ready to date. Gorgeous non-op 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 ...
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...
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, ...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Boston 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 in it's ...
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...
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...
Having fun and Staying Young Young-ish 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 @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
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...
TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Boston Hey lover 😘 I’m a high-femme TS bombshell — curves for days, lips made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet but I transform into a woman who crawls to the bed naked while wearing only a mischievous expression...
Penny for your thoughts? Penny TS in Boston
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 @PennyTSswitch!!
I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and exp...
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 ...- January 12th, 2026
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:...
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...
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...
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/Ebony Transsexual - Your New Addiction – One Taste and You’ll Beg for More 🍑💋 Warning: I’m addictive 😘 View My Ebony TS Profile here -
I possess more than attractive features. I am a complete TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and thick thighs and soft lips and a hidden secret th...
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...
Email Boston 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...