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

December 18th, 2025

Sexy Shemale Looking for Hot Fun in Boston Are you ready to have the time of your life with a horny shemale? I'm Lyndel, and I'm looking for a local man who can handle all of my desires. I love getting down and dirty, so if you're up for some wild fun, then I'm your girl! I love it all - from giving sloppy blowjobs to taking a huge cock d...

Raunchy Shemale Seeking Local Man for Wild Fun Are you ready to have the time of your life with a sexy shemale in Worcester? Well, look no further because Josephina is here to fulfill all your wildest fantasies! I'm a horny shemale looking for a man who can handle me in the bedroom and beyond. When it comes to sex, I love it all. From givin...

Elegant 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...

Raunchy 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 ...

Eager 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...

Wild Shemale Seeking Local Man for Hot Fun and Orgasms Are you looking for a naughty shemale who knows how to have a good time? Well, look no further because I'm Casie from Western MA and I'm ready to show you the time of your life. I love getting down and dirty with a man who can handle all my kinky desires. I'm a top shemale who loves to dominate i...

27 y/o Sexy Hung Crossdresser in Massachusetts Hung Crossdresser for Male in Massachusetts Hey, I go by Selena when I'm cross dressed. I love being feminine and servicing my man!, I'm age 27, well hung and so cute when I'm dressed up!! What more could you want in a gurl?!! View my pics and message me @Selena27femCD so we can talk and meet for a...

Hot 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...

Transgender Temptation in Boston Hey there! I'm Elana, a transgender cutie from Boston who loves exploring the city and meeting new people. I enjoy being part of the LGBTQ community because it allows me to be my authentic self without any judgment. If you're looking for someone fun and adventurous to go on a date with, look no fu...

Sexy Shemale Kathleen Looking for Hot Fun on Cape Cod I love nothing more than getting down and dirty with a man who knows how to handle a shemale like me. My name is Kathleen, and I am looking for a local guy who can satisfy all my desires. Whether you're into giving or receiving, I'm your girl. I enjoy everything from blowjobs to anal play, and I'...

Raunchy 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...

Euphoric 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...

Spark 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...

Hot Shemale in Worcester Looking for a Wild Time I'm a naughty shemale named Nena who loves to get down and dirty with a local man. I'm seeking someone who can handle my insatiable appetite for all things sexual. When it comes to getting down and dirty, I love to be on top, ride you like there's no tomorrow, and make you scream with pleasure. I ...

Transgender 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...

Hot Shemale in South Coast Looking to Fulfill Your Wildest Fantasies 🔥💋 Are you looking for a sexy shemale who can fulfill all your deepest desires? Look no further, because I am here to make your fantasies come true. My name is Elonore and I am a pre-op transgender woman located in South Coast, Massachusetts. You can find my bio at elonoreso21222. I love playing bot...

Hot Shemale Looking for a Naughty Man in Worcester! Hey there, I'm Kandace, a sexy shemale from Worcester looking for a local man to have some wild fun with. I love getting down and dirty, so if you're into that too, we'll definitely hit it off! You can find me on FreeSexAds.com Shemale Profiles at kandace78982.I'm a top who loves to dominate and tak...

Sexy 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 ...

Erotic Temptation: Seeking Connection in Worcester/Central MA Hey there! I'm Paule, a transgender babe from Worcester/Central MA. I love being part of the LGBTQ community because it allows me to express my true self and connect with others who understand and support me. I'm looking for someone special to go on fun dates with around town. We could grab a bi...

Looking for Love and Adventure in Western MA! Hey there, lovely people of Western MA! My name is Phyllys, and I'm a proud transgender individual who's ready to dive into the dating scene. 💖 So, let me tell you a bit about myself. I may not have been blessed with the body type of a supermodel, but my warm smile and infectious laughter more...

Spark 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...

Elegant 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...

Raunchy Shemale Dolora Seeking Local Man for Wild Fun I love getting down and dirty with a hot stud who knows how to handle a kinky shemale like me. My name is Dolora, and I'm on the hunt for a man in South Coast, Massachusetts who can satisfy all my cravings. From deepthroating to anal play, I'm open to exploring all kinds of naughty activities with...

Jasmin 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...

Hot 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...

INTERACTIVE MAP: Transexual Tracker in the Massachusetts Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Massachusetts area for friendship or sex hookups. View member thumbnails on the interactive map below to meet local members who want to meet local transexuals or admirers. Click any member photo below to get started. Sign up free...

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...

Seeking Local Man for Shemale Fun in Cape Cod / Islands, Massachusetts Are you ready to explore your wildest fantasies with a sexy shemale like me? My name is Ann and I'm looking for a hot local man who can handle all that I have to offer. I love getting down and dirty, so if you're into some raunchy fun, then I'm the girl for you. I enjoy everything from deepthroat...

Eager 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...

Local 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...

Wild 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...

Erotic Enchantment Awaits You, Let's Meet! Hey there! I'm Raye, a fun-loving transgender person from Boston, Massachusetts. I may not fit society's typical mold, but that's what makes me unique and exciting. I embrace my LGBTQ identity and love connecting with open-minded individuals who appreciate authenticity. I enjoy exploring the vibr...

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...

Sexy Shemale Seeking Local Man for Hot Fun Looking for a man who can handle a naughty shemale like me, Bridget. I'm all about exploring new things and pushing boundaries in the bedroom. I love being both top and bottom, giving and receiving blowjobs, getting my tight ass pounded, sucking on a throbbing cock until it explodes with cum, and ...

Eager to Explore: Transgender Beauty in Worcester Hey there, I'm Perri! I'm a sassy transgender babe from Worcester, MA, ready to mingle and have some fun. I love being part of the LGBTQ community because it allows me to express my true self without any judgment. I'm looking for someone who is open-minded and ready for an adventure. We could gr...

Sexy Shemale in Boston Looking for Hot Fun Hey boys, I'm Jayme, a hot shemale in Boston looking for a man who can handle all my desires. I love to be on top and dominate, but I also enjoy getting down on my knees and giving sloppy blowjobs. My tight ass is ready to be pounded hard, and I love it when you gag me with your huge throbbing cock....

Superior 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...

Sensual 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...

Elisabeth 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...

Elegant Enigma Seeking Connection Hey there! I'm Audrey from South Coast, Massachusetts. I may not fit into society's narrow definitions of gender, but that's what makes me unique and special. I embrace my transgender identity and love being a part of the LGBTQ community. 💖 I enjoy long walks on the beach, exploring local art ...

Transgender Temptation in Worcester Hey there! I'm Ricki, a fun-loving transgender cutie from Worcester, MA. I may not fit society's norms, but that's what makes me unique and fabulous. I embrace my LGBTQ identity with pride and confidence. If you're looking for someone who is genuine and down-to-earth, then look no further! I enjo...

Local 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...

Transgender Beauty Seeking Love on Cape Cod Hey there! I'm Mona, a transgender beauty from Cape Cod / Islands, Massachusetts. I may not fit society's standards of beauty, but I am confident in my own skin and proud to be part of the LGBTQ community. If you're looking for a unique and exciting date, look no further! I love exploring the loc...

Sexy Shemale in Boston Looking for Hot Fun Are you ready to experience the ultimate pleasure with a hot shemale like me, Arleta? I'm a naughty tranny who loves to play all night long. I'm seeking a local man who can handle my insatiable appetite for sex and fun. I love getting down and dirty with a man who knows how to please me. From pas...

Looking for Love and Adventure in Worcester! Hey there, it's Allison! 😊 I'm a proud transgender woman living in Worcester, Massachusetts. I'm excited to put myself out there and find someone special who appreciates me for who I am. 💕 As for my body type, ethnicity, and nationality, well, those are just details that make me unique. But...

Looking for Love and Adventure in South Coast, Massachusetts! Hey there, it's Ricca! 🌈 Are you ready to join me on an exciting journey through love and life? I'm a proud transgender individual who loves embracing my true self. Being part of the LGBTQ community has taught me the importance of acceptance, compassion, and living authentically. Living in bea...

Elegantly 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...

Raunchy 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...

HMU for Sex in Massachusetts Newly Single and Ready to Mingle in Massachusetts Hi guys, my name is Barbie, age 28. My husband cheated for the last time. Now it's my time to have some fun! If you want to hook up for passion and hot sex in the Massachusetts area then message me @BarbieSingle28.      ...

Seeking Connection and Adventure in Worcester! Hey there, I'm Marla, a fun-loving transgender woman from Worcester. I'm all about embracing my true self and living authentically as part of the LGBTQ community. If you're looking for someone who loves to laugh, explore new places, and have deep conversations, then I might just be your girl! I ...