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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June 21st, 2025

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...

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...

Let me be your sexy superhero tonight baby!... Yeah baby it's super tranny to the rescue in Boston. Freaky as hell, fully functional ebony t-girl and I always rise while others fall. If you need a sexual superhero tonight then I'm your choice tonight. I got 9 inches uncut that wants you to have your way. Oral, hand, anal or? Anything you want 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...

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...

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...

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...

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 ...

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...

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...

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...

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...

!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Boston Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Boston 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 Online Chat Mak...

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 ...

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 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...

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...

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...

June 20th, 2025

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:...

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 ...

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 ...

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...

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...

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 ...

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...

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 ...

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 ...

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 ...

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 ...

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...

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...

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...

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...

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...

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...

June 19th, 2025

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...

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!...

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...

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...

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...

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...

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....

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 ...

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...

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...

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 ...

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 ...

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...