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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  • November 29th, 2025
  • 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 Trans Profiles  &...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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 ...
  • 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 ...
  • 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...
  • 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...
  • 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 ...
  • November 28th, 2025
  • 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 ...
  • 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...
  • 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...
  • 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...
  • 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...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Boston Secret Crossdressing Hookups in Boston 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 private gara...
  • 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:...
  • Flawlessly gorgeous trans bombshell in Boston Trans MtF for Man in Boston I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom ey...
  • 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, ...
  • 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 ...
  • 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...
  • 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'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...
  • 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 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...
  • 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 ...
  • 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 ...
  • 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...
  • 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...
  • 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...
  • November 27th, 2025
  • The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Boston Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexual,...
  • 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....
  • 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...
  • 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 ...
  • 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...
  • 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 Boston area. Click here and come see me anytime!...
  • 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...
  • 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 ...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • 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 ...