Massachusetts Transgender Sex Ads

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

  • August 16th, 2025
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Looking for a hot stud to fulfill all my dirty desires. My name is Mara and I'm a shemale from Worcester / Central MA, Massachusetts. I'm on the hunt for a man who can handle my insatiable appetite for sex. I love getting down and dirty in the bedroom and exploring all kinds of kinky fetishes. ...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you ready for a night of mind-blowing pleasure with a horny shemale named Carolee? I'm looking for a hot stud in Cape Cod / Islands, Massachusetts who can satisfy all my naughty desires. When it comes to sex, I'm into everything from deepthroating your throbbing cock to riding you like a wild ...
  • Elegantly Transcendent: Seeking Connection in Cape CodElegantly Transcendent: Seeking Connection in Cape Cod Hey there! I'm Genna, a proud transgender woman from the beautiful Cape Cod / Islands area of Massachusetts. I have a curvy body and a mix of Italian and Portuguese heritage. You can check out my pics at my personal profile page @gennacape84105. I love being part of the LGBTQ community because it...
  • FtM seeking Princess Bride in MassachusettsFtM seeking Princess Bride in Massachusetts FtM seeking Woman in Massachusetts Hi, I'm Andy, age 33, FtM transgender man living in Massachusetts. Also, you must love that movie! If you don't get the reference you can still message me anyway! I love that movie and I will watch it with you over and again. View my pics and send me a message&nbs...
  • Transgender Beauty Seeking Love and Adventure Hey there! My name is Gwyn, and I'm a transgender person living in the beautiful Cape Cod/Islands area of Massachusetts. 🌈✨ I've always believed that love knows no boundaries, and I'm excited to meet someone who shares my passion for adventure and embracing life to the fullest. 💖 So, wha...
  • Transgender Beauty Looking for Love on Cape CodTransgender Beauty Looking for Love on Cape Cod Hey there! I'm Elvera, a proud transgender woman living on Cape Cod. I love exploring the beaches and quaint towns here, like Provincetown and Martha's Vineyard. If you're looking for a fun date with someone who embraces their LGBTQ identity, then look no further! I enjoy being trans because it a...
  • Raunchy Shemale Seeking Local Man for Hot Fun in Cape CodRaunchy Shemale Seeking Local Man for Hot Fun in Cape Cod I love to get down and dirty with a man who can handle all the kinky things I have in store. My name is Jenifer, and as a shemale, I am always up for a good time. Whether you're into getting your cock sucked or pounding my tight ass, I'm game for it all. I enjoy being both a top and bottom, so w...
  • Looking for Love and Adventure!Looking for Love and Adventure! Hey there! My name is Matty, and I'm a transgender person living in South Coast, Massachusetts. 🌊 I wanted to give this dating thing a try because I believe that love can be found in the most unexpected places. So, why not here? Let me tell you a bit about myself. Physically, I have a unique b...
  • Looking for Love and Adventure! <br>Looking for Love and Adventure!
    Hey there! My name is Moira, and I'm a transgender woman living in beautiful Boston, Massachusetts. 🌆 I wanted to take a moment to tell you a little bit about myself and what I'm looking for. First off, let me start by saying that being part of the LGBTQ+ community has been an incredible journ...
  • Sexy Shemale Carmen Looking for a Wild TimeSexy Shemale Carmen Looking for a Wild Time Are you ready to experience the ultimate pleasure with a hot shemale like me, Carmen? I'm a sultry vixen from South Coast, Massachusetts, seeking a local man who can handle all of my desires. When it comes to sex, I love it all - from giving sloppy blowjobs to riding your throbbing cock until we b...
  • Spark Your Curiosity with LissaSpark Your Curiosity with Lissa Hey there! I'm Lissa, a transgender woman from Boston, Massachusetts. I may not fit society's typical mold, but that's what makes me unique and confident in my own skin. I love embracing my LGBTQ identity and all the beauty that comes with it. If you're looking for someone who is genuine, fun-lovi...
  • Hot Shemale Mallorie Looking for Naughty Fun in BostonHot Shemale Mallorie Looking for Naughty Fun in Boston Are you a man who loves to get down and dirty with a sexy shemale? Well, look no further because I'm Mallorie, your ultimate fantasy come to life! I'm a kinky shemale from Boston, Massachusetts looking for a local man who can handle all my wild desires. I love it all - from being a top or bottom ...
  • Elegantly Transcending BoundariesElegantly Transcending Boundaries Hey there! I'm Rosanne, a proud transgender woman from Western MA, Massachusetts. I may not fit society's narrow beauty standards, but I embrace every part of myself with confidence and pride. I love exploring LGBTQ+ events and spaces in the area like Northampton Pride or The Queer Community Cente...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Hey sexy, I'm a hot shemale named Dorothy looking for a man in Cape Cod / Islands who can handle all my dirty desires. When it comes to sex, I'm into everything naughty and nasty. I love being both a top and bottom, giving blowjobs and getting my ass pounded hard. I enjoy sucking cock, riding it unt...
  • 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...
  • Raunchy Shemale Seeking Local Man for Wild FunRaunchy Shemale Seeking Local Man for Wild Fun Are you ready to explore your wildest fantasies with a sexy shemale in Worcester / Central MA? Look no further, because I'm Mariana and I'm here to fulfill all your desires. From deepthroat blowjobs to hardcore anal play, I love it all. Let's get down and dirty together, baby! 😈💦🍆 I'm a ...
  • Euphoria Awaits with AlysaEuphoria Awaits with Alysa Hey there! I'm Alysa, a transgender woman from Boston, Massachusetts. I may not fit society's mold of what a woman should look like, but that's what makes me unique and beautiful in my own way. I embrace my LGBTQ identity and love connecting with others who appreciate authenticity and diversity. ...
  • Looking for Love and Adventure Hey there! My name is Jeane, and I'm a transgender person living in Worcester, Massachusetts. 💖 I wanted to put myself out there and see if I can find someone special who appreciates me for who I am. So, here's a little bit about me! Physically, I have a curvy body that loves to dance and move...
  • 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...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Massachusetts Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • 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...
  • Looking for Love and Adventure in Western MA!Looking for Love and Adventure in Western MA! Hey there! My name is Lonee, and I'm a transgender person living in Western MA, Massachusetts. I'm excited to put myself out there and meet someone special who appreciates me for who I am. 🌈 I may have a curvy body type, but that doesn't stop me from embracing my unique self. Being trans has t...
  • 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 ...
  • Wild Shemale Looking for a Naughty Man to Play with in Western MAWild Shemale Looking for a Naughty Man to Play with in Western MA I'm Andie, a hot and horny shemale looking for a local man who can handle all the kinky fun I have to offer. I love being both a top and a bottom, giving and receiving blowjobs, getting my tight ass pounded, and sucking on a throbbing cock until it explodes with cum. I'm into all kinds of fetishes...
  • Elegant Enigma Seeking ConnectionElegant Enigma Seeking Connection Hey there! I'm Marylou from Worcester, MA. I'm a curvy, Latina transgender woman who loves embracing my true self and connecting with others in the LGBTQ community. I enjoy exploring new places in Central MA like Elm Park, Bancroft Tower, and the Worcester Art Museum for a fun date. I believe tha...
  • TS M2F Top in MassachusettsTS M2F Top in Massachusetts TS Top Seeking Man in Massachusetts I'm Sandi wants to meet hot guy for fun and hot sex. Age 28 with long blonde hair, smooth skin and a great body.  Non op functional, nice big ladystick for your pleasure! 😈  Love oral sex, anal sex and yummy kinks of all sorts. I love to explore kink...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Massachusetts? 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...
  • 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...
  • Spark Up Some Chemistry with JacklynSpark Up Some Chemistry with Jacklyn Hey there, I'm Jacklyn from South Coast, Massachusetts! I'm a curvy Latina beauty who loves embracing my transgender identity. Being part of the LGBTQ community has brought so much joy and acceptance into my life. I'm looking to meet someone special who appreciates authenticity and loves to have a...
  • 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...
  • Local Shemale Moreen Looking for Hot Fun and Wild TimesLocal Shemale Moreen Looking for Hot Fun and Wild Times Are you ready for a wild time with a hot shemale in Cape Cod / Islands, Massachusetts? Well, look no further because I'm Moreen and I'm here to fulfill all your dirty fantasies. I'm a horny shemale looking for a local man who can handle my insatiable appetite for sex. I love it all - from deepth...
  • Transcend the Norm with GatesTranscend the Norm with Gates Hey there! I'm Gates, a proud transgender individual from South Coast, Massachusetts. I may not fit society's typical mold, but that's what makes me unique and special. 🌈 I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and inspire othe...
  • Transcendental Temptations AwaitTranscendental Temptations Await Hey there, I'm Deeanne from Western MA, Massachusetts. I love exploring my identity as a transgender individual and embracing all aspects of the LGBTQ community. If you're looking for someone who is open-minded, adventurous, and loves to have a good time, then look no further! I enjoy meeting new...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Massachusetts 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 relations...
  • Wild Shemale Seeking Local Man for Hot FunWild Shemale Seeking Local Man for Hot Fun I love getting down and dirty, exploring all kinds of naughty fantasies with a willing partner. My name is Dinny, and I'm a shemale from Western MA looking for a man who can handle my insatiable appetite for pleasure. When it comes to sex, I'm open to just about anything. I enjoy being both a top ...
  • Spark Up Some Chemistry with Lissie in Boston!Spark Up Some Chemistry with Lissie in Boston! Hey there! I'm Lissie, a transgender gal from Boston who loves exploring the city and meeting new people. As a member of the LGBTQ community, I embrace my identity and all the unique experiences that come with it. If you're looking for someone who is open-minded, fun-loving, and down-to-earth, the...
  • Looking for Love in All the Right PlacesLooking for Love in All the Right Places Hey there, lovely people of Worcester and Central MA! My name is Katerina, and I'm here to put a little extra sparkle into your life. 🌟 So, let me tell you a bit about myself. I've got this gorgeous curvy figure that's just made for hugging. And my stunning blue eyes will have you mesmerized f...
  • Raunchy Shemale Seeking Local Man for Hot Fun and Great SexRaunchy Shemale Seeking Local Man for Hot Fun and Great Sex Are you ready to experience the ultimate pleasure with a sexy shemale like me, Gabrielle? I'm looking for a local man who can handle my insatiable appetite for all things naughty. When it comes to sex, I love it all - from giving sloppy blowjobs to taking a huge throbbing cock deep in my tight ass...
  • Elegantly Transgender Seeking Connection in BostonElegantly Transgender Seeking Connection in Boston Hey there! I'm Pippy, a transgender cutie from Boston who loves exploring the city's vibrant LGBTQ+ scene. Whether it's grabbing a coffee at the queer-friendly Diesel Café in Somerville or catching a drag show at Club Cafe in Back Bay, I'm always up for a good time. I embrace my trans identity ...
  • Local Shemale Looking for Hot Fun and Great SexLocal Shemale Looking for Hot Fun and Great Sex Are you a man in Cape Cod / Islands looking for a wild time with a sexy shemale? Well, look no further because I am here to fulfill all your fantasies and desires. My name is Malanie and I am ready to show you a night you won't forget. I love being both top and bottom, giving and receiving blowjo...
  • Hot Shemale in Boston Looking to Ride and SuckHot Shemale in Boston Looking to Ride and Suck Are you looking for a naughty shemale to fulfill all your wildest fantasies? Well, look no further because I'm Danny, a sexy shemale from Boston seeking a local man for some hot and steamy fun. I love getting down and dirty with a man who knows how to handle a tranny like me. I enjoy being both ...
  • LetLet's Explore Boston Together! Hey there! I'm Madelene, a fun-loving transgender woman from Boston, Massachusetts. I may not fit society's standards of beauty, but I embrace my unique body type and ethnicity with pride. I love being part of the LGBTQ community because it allows me to be my true self without any judgment. Whet...
  • Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Massachusetts Hi! I'm Brandi, new TS in the Massachusetts area. I'm MtF preop transexual woman. I pass as female very well so we can go to your business function or out for dinner followed by a night of forbidden fun that only we will know about! I am fully functional, 8" thick hidin...
  • Spark Up Some Chemistry with MelodySpark Up Some Chemistry with Melody Hey there! I'm Melody, a transgender cutie from South Coast, Massachusetts. I may not fit society's norms, but that's what makes me unique and fabulous! I love embracing my true self and connecting with others in the LGBTQ community. I'm looking for someone who is open-minded, fun-loving, and rea...
  • 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 ...
  • Spark the Flame of Passion with Colette from BostonSpark the Flame of Passion with Colette from Boston Hey there! I'm Colette, a fun-loving transgender gal living in Boston, Massachusetts. I may not fit society's standards of beauty, but my confidence and personality shine bright. I embrace my trans identity and love being part of the LGBTQ community. I enjoy cozy nights at local cafes like Think...
  • Transgender Beauty Looking for Love on Cape CodTransgender Beauty Looking for Love on Cape Cod Hey there! I'm Anna, a transgender cutie from Cape Cod / Islands, Massachusetts. I love being part of the LGBTQ community because it's all about acceptance and love. 🏳️‍🌈 I'm looking for someone who is open-minded and ready for a fun adventure. We could grab a coffee at The Daily Brew i...
  • Local Shemale Renelle Seeking Hot EncountersLocal Shemale Renelle Seeking Hot Encounters Are you looking for a wild time with a sexy shemale in Worcester / Central MA? Look no further, because I'm here to fulfill all your dirty desires. My name is Renelle and I'm ready to show you a good time. You can find me in the FreeSexAds.com Shemale Profiles at renelle44889. I love getting down...
  • Sexy Shemale Cat Looking for Hot Fun on Cape CodSexy Shemale Cat Looking for Hot Fun on Cape Cod I'm a horny shemale named Cat, and I'm looking for a local man who can handle all my desires. I love to play both top and bottom, giving and receiving pleasure in every way possible. I want to suck your cock until you're begging for more, then ride you until we both explode in ecstasy. I have a ...
  • Spark a Connection with Kitty in BostonSpark a Connection with Kitty in Boston Hey there, I'm Kitty and I'm a transgender woman living in Boston, Massachusetts. I love exploring the city and trying out new restaurants like Union Oyster House or The Beehive. There's nothing better than good food and great conversation! I enjoy being part of the LGBTQ community because it al...