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

July 1st, 2025

Elegant Enigma Seeking Connection Hey there! I'm Daisie, a transgender woman from the South Coast of Massachusetts. I may not fit society's standards, but I embrace my uniqueness and love being part of the LGBTQ community. 💖 I enjoy long walks on the beach, cozy coffee dates at local cafes like The Green Bean or Tia Maria's Eu...

Sexy Transgender Seeks Fun and Connection Hey there, I'm Enya from South Coast, Massachusetts. I'm a curvy, mixed-race beauty who loves embracing my transgender identity. Being part of the LGBTQ community brings me so much joy and freedom to express myself authentically. I'm looking for someone who is open-minded, adventurous, and ready ...

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...

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...

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...

Raunchy 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...

Spark Up Some Magic with Shellie Hey there! I'm Shellie from Western MA, Massachusetts. I'm a curvy and confident transgender woman who loves embracing my true self. Being part of the LGBTQ community brings me so much joy and freedom! 💖 I'm looking for someone special to share laughs, adventures, and maybe even some romance w...

Seeking Connection and Adventure Hey there! I'm Meggan, a fun-loving transgender woman from South Coast, Massachusetts. I'm all about embracing who I am and living authentically in the LGBTQ community. If you're looking for someone who is genuine, caring, and loves to explore new places, then I might just be the one for you. I e...

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...

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...

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...

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...

Searching for Love and Adventure! Hey there! My name is Clari, and I'm a proud transgender woman living in South Coast, Massachusetts. 💃🌈 I wanted to write this ad to let you know that I'm looking for someone special who appreciates the unique journey I've been on. Being transgender has given me a whole new perspective on l...

Raunchy 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, ...

June 30th, 2025

Looking for Love and Adventure in South Coast, Massachusetts! Hey there! My name is Mella, and I'm a transgender individual living in the beautiful South Coast of Massachusetts. 🌊❤️ I may not fit into society's typical mold, but that's what makes me special! Being transgender has allowed me to embrace my true self and appreciate the diversity within ...

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...

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...

Spark 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...

Sexy Transgender in South Coast Looking for Love! Hey there, I'm Pauli and I'm a proud transgender person living in South Coast, Massachusetts. I love being part of the LGBTQ community because it allows me to be my true self and connect with amazing people like you! I'm looking for someone who's open-minded, adventurous, and ready to have some ...

Sexy Transgender Seeks Connection in South Coast, Massachusetts Hey there, I'm Robbyn and I'm a proud transgender woman living in South Coast, Massachusetts. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and I wouldn't have it any other way! 💃 I'm looking for someone who is open-minded, kind-hear...

Elegant Enigma Seeking Connection 🌈 Hey there, I'm Brina from Western MA, Massachusetts. I may not fit society's mold, but that's what makes me unique! As a transgender individual, I love the freedom to express my true self and embrace my LGBTQ community with open arms. If you're looking for someone who is genuine and loves to explo...

Sexy Shemale Looking for Hot Fun in South Coast Are you ready to play with a naughty shemale like me, Nora? I'm seeking a local man who can handle all the kinky fun I have in store. From deepthroat blowjobs to rough anal play, I love it all. Let's explore each other's bodies and reach mind-blowing orgasms together. Whether you want me to be you...

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 ...

Seeking Connection and Adventure Hey there! I'm Roanne, a transgender woman living in Boston, Massachusetts. I may not fit society's mold of what a woman should look like, but that doesn't stop me from embracing my true self and living authentically. You can check out my pics at my personal profile page @roanneb12275. I love exp...

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...

TS 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...

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...

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 ...

Hot Shemale in Worcester Looking for Some Naughty Fun I'm Toni, a sexy shemale in Central MA looking for a local man to have some wild and kinky fun with. I love getting down and dirty, exploring all kinds of naughty fantasies. I'm a top who loves to dominate, but I can also be your submissive bottom if that's what you're into. Let's play together a...

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...

Naughty Shemale Looking for Hot Fun in Boston Hey there boys, it's Vivie here, your favorite sexy shemale from Boston. I'm on the hunt for a local man who can handle all that I have to offer. When it comes to sex, I'm into everything naughty and kinky. I love being both a top and a bottom, giving blowjobs and getting my tight ass pounded. I enj...

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...

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...

Euphoria 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. ...

Erotic Transgender Temptation in Worcester Hey there, I'm Chelsae from Worcester, MA. I'm a curvy transgender woman who loves embracing my LGBTQ identity. If you're looking for a fun and adventurous date, then look no further! I enjoy exploring new places around Central MA like the Worcester Art Museum or grabbing a bite to eat at Armsby A...

Hot 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 ...

Sexy 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...

Sexy Shemale Seeking Local Man for Wild Fun in Boston Are you ready to explore your wildest fantasies with a hot and horny shemale? Look no further, because I'm here to make all your dreams come true. My name is Bernadene and I'm a sexy shemale looking for a man who can handle all that I have to offer. When it comes to sex, I love it all – from d...

Elegantly Transcendent: Seeking Connection in South Coast, MA Hey there! I'm Rayshell, a transgender beauty from South Coast, Massachusetts. I love embracing my true self and connecting with others who appreciate the LGBTQ community. If you're looking for someone unique and open-minded, then look no further! I enjoy exploring local spots like the scenic be...

Elegantly Transformed: Seeking Connection in Western MA Hey there! I'm Cristina, a proud transgender woman from Western MA. I may not fit society's mold, but that's what makes me unique and beautiful. I love exploring my identity and connecting with others in the LGBTQ community. It's empowering to be true to myself and embrace who I am. If you're open...

Looking for Love and Adventure! Hey there! I'm Harrietta, a fun-loving transgender gal from Boston, Massachusetts. If you're into exciting dates and genuine connections, then keep reading! So, what do I look like? Well, picture this: I have a curvy body that'll make you weak in the knees. My luscious hair frames my face perfect...

Sparkling 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...

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...

Sexy Shemale Sherry Ready to Fulfill Your Wildest Fantasies 💋🍆💦 Are you looking for a kinky and adventurous shemale to play with in Western MA, Massachusetts? Look no further, because I'm here to make all your dreams come true. My name is Sherry and I am a pre-op trans woman who loves to have a good time in the bedroom. You can find my bio at sherry90667. I e...

Seeking Connection and Adventure Hey there! I'm Jeannette, a transgender woman from Worcester/Central MA, Massachusetts. I'm excited to put myself out there and meet someone special who sees me for who I truly am. 🌈 So, let me tell you a bit about myself. While it's hard to describe my unique body type in words, I can assure ...

Transgender Temptation in Worcester Hey there! My name is Dido and I'm a transgender beauty from Worcester, Massachusetts. I love embracing my true self and being part of the LGBTQ community. It's empowering to live authentically and be surrounded by love and support. I'm looking for someone special to share fun times with. We coul...

Local Shemale Looking for Hot Fun Are you ready to have the time of your life with a sexy shemale in Cape Cod / Islands, Massachusetts? Look no further because I'm here to fulfill all your wildest fantasies. My name is Noelyn and I'm a horny shemale seeking a local man for some steamy encounters. I love getting down and dirty, so...

Raunchy Shemale Looking for Hot Fun in Western MA Hey boys, I'm Ida, a naughty shemale from Western MA looking for a local man who can handle all of me. I love getting down and dirty, so if you're into wild and kinky fun, I'm your girl... err... shemale! I enjoy being both a top and a bottom, giving and receiving blowjobs, getting my tight ass p...

Wild 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 ...

Raunchy 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 ...