Massachusetts Transgender Sex Ads

Browse Massachusetts transgender sex ads to meet local transexuals, crossdressers and shemales for sex, dating or friendship. It's free to search the trans sex 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

  • November 3rd, 2025
  • EveleenEveleen's Sensual Journey in Boston Hey there! I'm Eveleen, a transgender beauty from Boston, Massachusetts. I love exploring the city and trying out new restaurants like The Beehive or Toro. I also enjoy taking long walks in the Public Garden or catching a show at the Wang Theatre. Being part of the LGBTQ community has brought so...
  • Raunchy Shemale Marysa Seeking Local Man for Wild FunRaunchy Shemale Marysa Seeking Local Man for Wild Fun Hey boys, I'm a hot and horny shemale named Marysa from South Coast, Massachusetts looking for a man who can handle all of me. I love getting down and dirty, so if you're into some kinky fun, I'm your girl. When it comes to sex, I'm not shy about what I like. I enjoy giving and receiving blowjobs, ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey boys, looking for a hot shemale to fulfill all your wildest fantasies? Look no further because Lynnette is here to make all your dreams come true. I'm a horny shemale from Boston, Massachusetts, ready to show you a good time. I love getting down and dirty with a man who knows how to handle a tr...
  • Looking for Love and Adventure! <br>Looking for Love and Adventure!
    Hey there, lovely people of Cape Cod and the Islands! It's Cornelia here, your friendly transgender soul on a quest for love. 💖 I may not have the body type of a supermodel or the ethnicity and nationality you might expect, but hey, who needs labels when we're all just looking for that special...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Massachusetts 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: Ga...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey boys, I'm Gianina, a hot shemale from Worcester / Central MA looking for a man who can handle all my dirty desires. I love getting down and dirty, so if you're into some kinky fun, I'm your girl... err, shemale! I'm a top who loves to dominate and take control in the bedroom. I'll make you beg f...
  • Raunchy Shemale Seeking Hot and Horny Man for Wild FunRaunchy Shemale Seeking Hot and Horny Man for Wild Fun Hey sexy, I'm Karoline from Worcester / Central MA, Massachusetts. I'm a naughty shemale looking for a local man who can handle all my desires. I love to be on top, riding you like there's no tomorrow. My tight ass is always hungry for a throbbing cock, ready to be filled up with your cum. I'll give...
  • Elegant Trans Beauty Seeking Connection in Western MAElegant Trans Beauty Seeking Connection in Western MA Hey there, I'm JoAnn from Western MA, Massachusetts. I'm a curvy Latina beauty who loves exploring the vibrant LGBTQ community here. Whether it's grabbing a coffee at Esselon Cafe or enjoying a hike at Mount Tom State Reservation, I'm always up for an adventure. I embrace my trans identity and l...
  • Elegant Transgender Beauty Seeking ConnectionElegant Transgender Beauty Seeking Connection Hey there, I'm Shayla from Worcester / Central MA, Massachusetts. I'm a curvy and confident transgender woman with a mix of Latina and European heritage. I love exploring my identity as part of the LGBTQ community, and I embrace every aspect of who I am. If you're looking for someone who is genuin...
  • Looking for Love and Adventure on Cape Cod!Looking for Love and Adventure on Cape Cod! Hey there! My name is Della, and I'm a transgender woman living here on beautiful Cape Cod. 💕 I wanted to reach out and see if there might be a special someone out there who's interested in going on an amazing journey with me. As a member of the LGBTQ+ community, I embrace my identity and love...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Massachusetts 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 ...
  • Looking for Love and Adventure on Cape Cod!Looking for Love and Adventure on Cape Cod! Hey there, lovely people of Cape Cod! My name is Dina, and I'm a transgender woman who's excited to dive into the dating scene. 💃🌈 Living in this beautiful part of Massachusetts has its perks, but finding that special someone can be a challenge. So here I am, putting myself out there, hopin...
  • Raunchy Shemale Looking for Local Man to Play WithRaunchy Shemale Looking for Local Man to Play With Are you ready to have some naughty fun with a sexy shemale named Loren? I'm a hot and horny tranny from Cape Cod / Islands, Massachusetts, seeking a man who can handle all my dirty desires. I love getting down and dirty in the bedroom, so if you're up for some wild adventures, then I'm the girl fo...
  • Elegantly Transgender in Worcester - LetElegantly Transgender in Worcester - Let's Meet Up! Hey there! I'm Adeline, a transgender woman living in Worcester, MA. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and connect with others who appreciate me for who I am. I'm looking for someone who is open-minded, kind-hearted, and up...
  • Hot Shemale Looking for Local Man to Fuck My Tight Ass and Throbbing CockHot Shemale Looking for Local Man to Fuck My Tight Ass and Throbbing Cock I'm Amie, a sexy shemale from Cape Cod / Islands, Massachusetts, seeking a man who can handle all of my naughty desires. I love being both a top and a bottom, giving blowjobs, getting my ass pounded, and sucking on a throbbing cock until it explodes with cum. I'm into all kinds of kinky play, from...
  • Seeking Connection and Adventure on Cape Cod! Hey there! My name is Delphina, and I'm a transgender woman living in the beautiful Cape Cod/Islands area of Massachusetts. 🌊🏖️ I'm here to share a little about myself and hopefully catch your attention! While I believe that true connections go beyond appearances, it's always nice to have...
  • Sexy Shemale Seeking Local Man for Wild FunSexy Shemale Seeking Local Man for Wild Fun I love getting down and dirty with a hot guy who knows how to please a shemale like me. My name is Kristyn and I'm looking for someone in South Coast, Massachusetts who can handle all my naughty desires. I enjoy being both a top and a bottom, so we can switch things up and have the best of both w...
  • Gorgeous, Passable Trans in Massachusetts 😍Gorgeous, Passable Trans in Massachusetts 😍 Gorgeous Passable Trans MtF for Man in Massachusetts 😍 I transitioned 6 years ago at age 18. I am pretty, with long light brown hair, a nice figure and long shapely legs. I have brown puppy dog eyes and kissable lips. Check my profile @TransFaye24 for pics and prepare to be stunned!  ...
  • Transgender Beauty looking for Love on Cape CodTransgender Beauty looking for Love on Cape Cod Hey there! My name is Karry and I'm a transgender woman living in the beautiful area of Cape Cod / Islands, Massachusetts. I have a curvy body type and I love embracing my femininity every day. I'm looking for someone who is open-minded and accepting of the LGBTQ community. I enjoy going to local...
  • Raunchy Shemale in Western MA Looking to PlayRaunchy Shemale in Western MA Looking to Play Are you looking for a hot shemale to fulfill all your wildest fantasies? Well, look no further because I'm Jayme, a sexy shemale from Western MA ready to show you a good time. I'm seeking a local man who can handle my insatiable appetite for great sex and fun. When it comes to the bedroom, I lo...
  • Exploring Love and Connection as a Transgender IndividualExploring Love and Connection as a Transgender Individual Hey there! It's Laura, a proud transgender woman from Worcester/Central MA, Massachusetts. I'm excited to dive into the world of dating and find that special someone who appreciates me for who I am. 💖 Being trans has brought so much joy and growth into my life. The LGBTQ community has become m...
  • Spark up Some Magic with ViviaSpark up Some Magic with Vivia Hey there, I'm Vivia from Boston, Massachusetts. I'm a curvy, Latina transgender woman who loves exploring the city and trying new things. 🏙️ When it comes to dating, I enjoy connecting with open-minded individuals who appreciate the beauty of the LGBTQ community. 🌈 If you're looking for ...
  • Eager to Meet Someone SpecialEager to Meet Someone Special Hey there! I'm Paulie, a transgender guy from Western MA, Massachusetts. I may not fit into society's typical mold, but that's what makes me unique and special. I love being part of the LGBTQ community because it allows me to be my authentic self without any judgment. If you're looking for someone...
  • Tempting Transgender Beauty Looking for LoveTempting Transgender Beauty Looking for Love Hey there, I'm Sherie from South Coast, Massachusetts. I'm a curvy, Latina transgender woman who loves embracing my true self and being part of the LGBTQ community. I enjoy exploring new places and trying different cuisines, so why not meet up for a date at the cozy cafe downtown or take a stroll ...
  • Transgender Beauty Looking for Love in Worcester!Transgender Beauty Looking for Love in Worcester! Hey there! I'm Gillan, a proud transgender woman from Worcester, MA. I may not fit society's definition of "normal," but that's what makes me unique and beautiful. I embrace my LGBTQ identity and love being part of such a diverse community. I'm looking for someone who can appreciate me for who I ...
  • Sexy Shemale in Worcester Looking for Hot FunSexy Shemale in Worcester Looking for Hot Fun Are you a man who loves to get down and dirty with a sexy shemale? Well, look no further because I'm Josephine, and I'm here to fulfill all your wildest fantasies. I'm a horny shemale seeking a local man for some mind-blowing sex and fun. I love being both top and bottom, so whether you want me ...
  • Euphoric Trans Beauty Looking for ConnectionEuphoric Trans Beauty Looking for Connection Hey there! I'm Leiah, a proud transgender woman from Worcester, MA. I love exploring my identity and embracing all the unique experiences that come with being LGBTQ. 💃 I'm looking to meet someone special who appreciates me for who I am. Let's grab a cup of coffee at Acoustic Java or take a str...
  • Elegantly Unique Transgender Beauty Looking for LoveElegantly Unique Transgender Beauty Looking for Love Hey there! I'm Gabriela, a transgender woman from South Coast, Massachusetts. I love being part of the LGBTQ community because it's where I feel most accepted and free to be myself. 🏳️‍🌈 I'm looking for someone who appreciates my uniqueness and is open-minded. Let's grab a coffee at The...
  • Elegant Transgender Beauty Seeking Connection in Worcester!Elegant Transgender Beauty Seeking Connection in Worcester! Hey there! I'm Chloe, a transgender woman from Worcester, MA. I may have a curvy body, but my heart is full of love and adventure. Being part of the LGBTQ community brings me so much joy and freedom to express myself authentically. I'm looking for someone special to share laughs and good times wi...
  • Sparkling Sea Breeze Seeks ConnectionSparkling Sea Breeze Seeks Connection Hey there! I'm Livia, a transgender woman from Cape Cod / Islands, Massachusetts. I have a curvy body and a mix of Italian and Portuguese heritage that gives me a unique look. I love exploring the local beaches, trying out new seafood restaurants, and taking long walks along the shore. I enjoy be...
  • Elegantly Transcendent Seeking ConnectionElegantly Transcendent Seeking Connection Hey there, I'm Joly from Worcester in Central MA. I'm a voluptuous Latina beauty who loves embracing my transgender identity. Being part of the LGBTQ community brings me so much joy and freedom to be myself. I enjoy exploring new places, trying different cuisines, and having deep conversations about...
  • Hot Shemale Angela Looking for Local Man for Wild FunHot Shemale Angela Looking for Local Man for Wild Fun I'm Angela, a sexy shemale from Cape Cod / Islands, Massachusetts, looking for a man who can handle all my desires. I love to be on top and take control, but I also enjoy getting down on my knees and giving sloppy blowjobs. I have a tight ass that loves to be pounded hard, and a huge throbbing coc...
  • Transgender Cutie Seeking ConnectionTransgender Cutie Seeking Connection Hey there! I'm Scotty, a transgender guy from South Coast, Massachusetts. I love exploring the local beaches and grabbing a bite to eat at cozy cafes in town. If you're into art, we could check out the galleries together or catch a movie at the indie theater downtown. I enjoy being part of the LG...
  • AngelAngel's Sensual Transgender Dating Ad Hey there! I'm Angel, a transgender cutie from South Coast, Massachusetts. I may not fit society's typical mold, but that's what makes me unique and special. Being part of the LGBTQ community has brought so much color and vibrancy into my life 🏳️‍🌈. I love exploring new places and tryin...
  • Looking for Love and Adventure on Cape Cod! Hey there, lovely people of Cape Cod! My name is Ruby, and I'm a transgender woman who's ready to dive into the dating scene. 💃✨ So, let me tell you a little about myself. I have a curvy figure that embraces my femininity, and my warm smile will surely brighten your day. As for my background...
  • Raunchy Shemale Seeking Local Man for Hot FunRaunchy Shemale Seeking Local Man for Hot Fun Hey boys, it's me, Courtney! I'm a sexy shemale from South Coast, Massachusetts looking for a man who can handle all my naughty desires. I love to get down and dirty in the bedroom, so if you're up for some wild fun, hit me up! When it comes to sex, I'm into everything from sloppy blowjobs to deep ...
  • Sensual Transgender Seeking ConnectionSensual Transgender Seeking Connection Hey there, I'm Daryl from South Coast, Massachusetts. I'm a tall, curvy trans woman with a mix of Brazilian and Irish roots. I love exploring my identity and being part of the LGBTQ community. It's empowering to be true to myself and connect with others who appreciate authenticity. I'm looking fo...
  • LetLet's Explore Love and Adventure Together! 🌈 Hey there, lovely people of Boston! My name is Malory, and I'm excited to dive into the world of dating as a proud transgender individual. 💖 I believe that love knows no boundaries, and I'm eager to meet someone who shares my enthusiasm for life. Whether you identify as LGBTQ or simply appreci...
  • Eager to Explore Love and ConnectionEager to Explore Love and Connection Hey there, I'm Jonie from Boston, Massachusetts. I'm a curvy Latina beauty who loves embracing my transgender identity. Being part of the LGBTQ community brings me so much joy and fulfillment. I'm looking for someone who can appreciate me for who I truly am. I enjoy exploring new restaurants in t...
  • Hot Shemale Looking for a Man to Play WithHot Shemale Looking for a Man to Play With Hey guys, I'm Morena and I'm a sexy shemale from Worcester / Central MA looking for a local man who can handle my insatiable appetite for wild sex. I love getting down and dirty, so if you're into some kinky fun, I'm your girl!When it comes to the bedroom, I'm all about exploring new things and push...
  • 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 Massachusetts 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 naugh...
  • Local Shemale Wendi Looking to Play and Ride Your Huge CockLocal Shemale Wendi Looking to Play and Ride Your Huge Cock Are you ready for a wild night of passion with a sexy shemale like me, Wendi? I'm on the hunt for a local man who can handle all my desires and give me the pleasure I crave. When it comes to sex, I'm into everything from sloppy blowjobs to deep anal play. I love being both a top and bottom, so we ...
  • Looking for Love and Adventure on Cape Cod!Looking for Love and Adventure on Cape Cod! Hey there! My name is Zara and I'm a transgender woman living in beautiful Cape Cod. 💃🏻 I'm here to find someone special who can appreciate me for the unique person I am. So, let me tell you a bit about myself! Physically, I have a curvy figure that'll make your heart skip a beat. 😍 My h...
  • Transgender Beauty Seeking Love and Adventure on Cape CodTransgender Beauty Seeking Love and Adventure on Cape Cod Hey there! I'm Celisse, a stunning transgender beauty hailing from the breathtaking shores of Cape Cod. 💃🏻✨ If you're looking for someone unique, open-minded, and ready to embrace life's adventures, then you've come to the right place. So, what do I look like? Well, picture this: a radian...
  • Seeking Local Man for Shemale Fun and Great SexSeeking Local Man for Shemale Fun and Great Sex I'm Ally, a sexy shemale from South Coast, Massachusetts, looking for a man who can handle me in the bedroom. I love getting down and dirty with a guy who knows how to please a tranny like me. If you're into wild, raunchy sex, then I'm your girl! I enjoy all kinds of naughty activities, including...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Massachusetts 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 Me...
  • Seeking Connection and AdventureSeeking Connection and Adventure Hey there! My name is Felecia, and I'm a transgender woman from Western MA, Massachusetts. I have a curvy body type and my heritage is Italian-American. I love exploring new places and meeting new people, especially those who appreciate the LGBTQ community like I do. I enjoy grabbing a cup of co...
  • Hot Shemale in Worcester Looking for a Wild TimeHot Shemale in Worcester Looking for a Wild Time Hey there, I'm Karine, a sexy shemale from Worcester looking for a local man to have some naughty fun with. I love getting down and dirty, so if you're into that too, we'll get along just fine. I'm always up for a good time and I have plenty of tricks up my sleeve to keep you satisfied.When it comes...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Massachusetts My name is Karl and I am a F2M trans dude. I was born female but transitioned to male a few years ago. I love my new body. I like dressing sharp with nice suits and taking good care of my hair and my beard. Sometimes it is just scruff and other times I let ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey there, I'm a sexy shemale named Heath from Cape Cod / Islands, Massachusetts, looking for a man who can handle my insatiable appetite for all things naughty. When it comes to sex, I'm open to just about anything - from giving mind-blowing blowjobs to taking you deep in my tight ass. I love to ri...