Boston Trans and Crossdressers Classifieds

Boston trans and crossdressers classifieds - meet local trans women for dating, sex hookups or friendship. Browse transgender and crossdresser classifieds or post your own ad. Meet local TS/CD hotties to live your wildest fantasies!

Home / Shemale Dating / Trans And Crossdressers

Show Ads In: Boston | Cape Cod / Islands | South Coast | Western MA | Worcester / Central MA

  • July 13th, 2025
  • Well Endowed Shemale is beautiful Boston 32Well 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 at BlancaShemale32 for my latest pictures and proof of my size! ...
  • TRANSGENDER LADYโค๏ธsexy hookupsTRANSGENDER LADYโค๏ธ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...
  • INTERACTIVE MAP: Transexual Tracker in the Boston Area!INTERACTIVE MAP: Transexual Tracker in the Boston Area! Local Transexual Hookups Meet local transexuals in the Boston 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 Boston Trans Hookups Map ...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in BostonSECRET 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...
  • Dr FreakinDr 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 Need a STEAM ROLLER Baby!!!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 ...
  • II'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 ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!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...
  • British T-girl Seeking Classy Gentleman in Boston...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...
  • Crystal, 27 New to the areaCrystal, 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 masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...
  • Hi Guys!! I am looking for someone fun!Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...
  • SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now!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 Shemale Profiles  ...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Boston!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...
  • Let me be your sexy superhero tonight baby!...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...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Boston 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: GayleTGir...
  • Flawlessly gorgeous trans bombshell in BostonFlawlessly gorgeous trans bombshell in Boston Trans MtF for Man in Boston I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send your re...
  • Twisted Sister - Loves to Ride.... and be Ridden!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 LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Boston )I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Boston ) Sexy Crossdresser Elissa Looking for Hot Fun in Boston๐Ÿ’‹    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 am a pr...
  • Tantalizing Tina with a HUGE W33NAH!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 ...
  • Marina TS ๐Ÿ† Visiting and ReadyMarina TS ๐Ÿ† Visiting and Ready Visitng Houston, Texas - Your TGirl Escort Hi guys Marina TS visiting your city …. We can start a sexy friendship, but if you are generous, it would not be bad. Please call me and text me when you are ready....MESSAGE ME HERE. Sexy, latina, femenine and beatiful TS woman here. English/e...
  • Brandi 27 tall slim hot trans chick 8.5 inchBrandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Boston Beautiful Brandi. If you're attracted to the female form then you will want to message me @ BrandiTS27.  I'm pre-op, tall, slim and beautiful with 8.5 inches for top or bottom. I love oral sex!! Kink friendly, have toys to explore all your naught...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Boston 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 relationship.&nb...
  • Elisabeth waiting to be your QueenElisabeth 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! Private Message @...
  • Black Boston Trans Hottie Wants to Freak You Tonight!...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...
  • Letha Aims to Fill YOU With Her Love Gun!!!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, ...
  • A monster in the sheets, but a lady in the streets...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...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Boston 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...
  • Tiffany Shelle - Your Boston Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Boston Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Boston It’s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGIT โœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functioning...
  • Trans Playmate Sex Kitten...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...
  • Email Local Shemales Now! ๐Ÿ’ŒEmail Local Shemales Now! ๐Ÿ’Œ Want to Hookup and Find Local 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'reinterested in ๐Ÿ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • Smoke me out baby!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 ...
  • July 12th, 2025
  • I want to be a whoreI 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!...
  • She-male looking for hot date to please. She-male looking for hot date to please. Asian Shemale in the Boston Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them come t...
  • Selena Trans girl cute looking for loveSelena 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 and send message for date....
  • M-F trans woman wants a dateM-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....
  • Your Flirty CD Sweetheart Awaits ๐Ÿ’•๐Ÿ˜˜ BostonYour Flirty CD Sweetheart Awaits ๐Ÿ’•๐Ÿ˜˜ Boston 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. ๐Ÿ’‹ ๐Ÿ‘  Feminine, fun and ...
  • DonDon't Worry I Bite! Feisty redhead trans in Boston full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard to control my...
  • Local Crossdresser ๐Ÿ˜‰๐Ÿ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser ๐Ÿ˜‰๐Ÿ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Boston View My Personal Pix - ๐Ÿคซ  A sexy Crossdresser from Boston, 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 dirty games and...
  • Upscale T-Girl in Boston Seeking Gentlemen of Taste for Fun...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 ...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.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 wife doesn't approve. I really need to let my fem side out to play! I'm seeking cross dressing frie...
  • Sassy CD Looking for a Real Man ๐Ÿ˜˜๐Ÿ”ฅSassy CD Looking for a Real Man ๐Ÿ˜˜๐Ÿ”ฅ  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...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Boston 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....
  • Superb Shemale in Boston...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...
  • BostonBoston'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...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Boston? Hey, I am Jasmin, 8" with a great body and busty. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for hot dates and see where it goes!  Hit me up @SweetJasminT...
  • DonDon'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...
  • Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Transgender๐ŸŸขTINA TS๐Ÿ˜‰๐Ÿ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina ๐Ÿ’‹ 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...
  • Erotic exotic Asian queen in Boston now (25)Erotic exotic Asian queen in Boston now (25) Asian Transexual in Boston Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....
  • New Body New MeNew Body New Me M2F post-op in Boston Hi, I'm Natasha, newly transitioned and ready to date. Gorgeous red head 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 me. Message me online NatashaM...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Boston Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...