Boston Transgender Sex Ads

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  • February 21st, 2025
  • 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 ...
  • 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 ...
  • 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...
  • Erotic Enchantment Awaits You, LetErotic 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...
  • Sexy Shemale in Boston Looking for Hot FunSexy 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...
  • A Symphony of SensualityA Symphony of Sensuality Hey there! I'm Melodie, a transgender woman from Boston, Massachusetts. I may have a curvy body, but my heart is even bigger. I love exploring the city and checking out local spots like Fenway Park or the Museum of Fine Arts. Let's grab a coffee at Thinking Cup or go for a stroll in the Public Gar...
  • Looking for Love and Adventure! 🌈Looking for Love and Adventure! 🌈 Hey there! My name is Louisa, and I'm a transgender woman living in beautiful Boston, Massachusetts. 💖 I wanted to take a moment to share a little about myself and what I'm looking for in the dating world. First things first, let's talk about what I love about being part of the LGBTQ+ communit...
  • Meet Massachusetts Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans ClubsMeet Massachusetts Transexuals Online: Live Chat, Member Profiles, Photo Swaps & Local Trans Clubs Meet Massachusetts Transexuals Online!  Meet Massachusetts transexuals online at AmericanTransexuals.com. Our web development team includes transexual women and male trans admirers, so we have a unique understanding of transgender attraction. We have created an online community where you can m...
  • Sexy Shemale in Boston Looking for Hot FunSexy 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....
  • Seeking Connection and AdventureSeeking 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...
  • Sexy Shemale Looking for Hot Fun in BostonSexy 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...
  • 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...
  • 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...
  • 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...
  • 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...
  • Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖Sexy M2F Preop Trans, Lovely Surprise Waiting in my Panties 💖💖 Preop Trans in Boston Hi! I'm Brandi, new TS in the Boston 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 hiding in my pantie...
  • Well Endowed Shemale for Man in BostonWell Endowed Shemale for Man in Boston Hung Shemale for Man in Boston I am Blanca. I can provide top or bottom service. Bareback if you're clean. Love oral sex both giving and receiving. Say hello cause I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me privately at BlancaShemale32 for my latest uncensor...
  • 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...
  • Gorgeous, Passable Trans in Boston 😍Gorgeous, Passable Trans in Boston 😍 Gorgeous Passable Trans MtF for Man in Boston 😍 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!  I'm kin...
  • 27 y/o Sexy Hung Crossdresser in Boston27 y/o Sexy Hung Crossdresser in Boston Hung Crossdresser for Male in Boston 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 r...
  • Elegant Enigma Seeking ConnectionElegant Enigma Seeking Connection Hey there, I'm Karlee from Boston, Massachusetts. I may not fit society's typical mold, but that's what makes me unique! As a transgender individual, I embrace my journey and love being part of the LGBTQ community. I enjoy exploring new places in Boston like the Public Garden or catching a show ...
  • 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 @...
  • A Sensual Journey of Self-DiscoveryA Sensual Journey of Self-Discovery Hey there, I'm Gaby from Boston, Massachusetts. I'm a curvy Latina beauty with a passion for exploring the world as a proud transgender woman. I love embracing my true self and connecting with others who appreciate authenticity and diversity. I enjoy cozy coffee dates at local cafes like Thinkin...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Boston 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 hi!&nbs...
  • 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...
  • 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...
  • SHEMALE HOOKUPS! Wanna Have a Great Time in Boston, Massachusetts? SHEMALE HOOKUPS! Wanna Have a Great Time in Boston, Massachusetts? HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS!  Shemale Profiles Browse Uncensored Photos, Swap Your Pics, Join Live Web Cams, Swap Private Messages, Sext & Hook Up! Join free for Instant Access to the Bost...
  • Transgender Beauty Looking for LoveTransgender Beauty Looking for Love Hey there! My name is Billi and I'm a transgender woman living in Boston, Massachusetts. I love exploring the city and trying new restaurants like The Beehive or Toro. I also enjoy taking long walks along the Charles River Esplanade or catching a movie at the Coolidge Corner Theatre. I'm proud to...
  • Shemale Nightclubs Near You in Boston, MassachusettsShemale Nightclubs Near You in Boston, Massachusetts Shemale Nightclubs Near You in Boston, Massachusetts Shemale Clubs Near You in Boston, Massachusetts is a directory of trans-friendly nightclubs and bars. LGBTQ+ clubs come and go. We strive to keep this transgender clubs directory complete and rely on your input to help us do so. Please contact ...
  • Embrace the Magic of Trans Love with FawnEmbrace the Magic of Trans Love with Fawn Hey there! I'm Fawn, a proud transgender babe from Boston, Massachusetts. I may have a curvy body, but my spirit is as free as a bird 🌈. Being part of the LGBTQ community fills my heart with so much joy and love ❤️. If you're looking for a unique and magical connection, then look no further...
  • 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 naughty fant...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Boston 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 it grow...
  • 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. ...
  • 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...
  • INTERACTIVE MAP: Transexual Tracker in the Boston Area!INTERACTIVE MAP: Transexual Tracker in the Boston Area! Local Trans Hookups Interactive Mapping Meet Local transexuals in the Boston 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 for in...
  • February 20th, 2025
  • Naughty Shemale Looking for Hot Fun in BostonNaughty 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...
  • Exploring Love and Connection as a Transgender BeautyExploring Love and Connection as a Transgender Beauty Hey there, I'm Matti from Boston, Massachusetts. I'm a proud transgender woman who loves embracing my true self and connecting with others in the LGBTQ community. If you're looking for someone who is authentic, compassionate, and full of love, then look no further! I enjoy exploring new places in...
  • 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...
  • 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...
  • HMU for Sex in BostonHMU for Sex in Boston Newly Single and Ready to Mingle in Boston 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 Boston, Massachusetts area then message me @BarbieSingle28.      ...
  • Sexy Shemale Looking for Hot Fun in BostonSexy Shemale Looking for Hot Fun in Boston I'm Charmane, a sultry shemale looking for a local man who can handle all of me. I love getting down and dirty, exploring every inch of your body with my throbbing cock. From blowjobs to anal play, I'm ready to fulfill all your wildest fantasies. I enjoy being both a top and a bottom, switching t...
  • 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 ...
  • 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...
  • FtM seeking Princess Bride in BostonFtM seeking Princess Bride in Boston FtM seeking Woman in Boston Hi, I'm Andy, age 33, FtM transgender man living in Boston. 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 @AndyFtM4Pri...
  • Hot Shemale in Boston Looking for Some Naughty FunHot Shemale in Boston Looking for Some Naughty Fun Are you ready to explore your wildest fantasies with a sexy shemale like me? My name is Dyna and I'm looking for a local man who can handle all the kinky fun I have to offer. I love being both top and bottom, giving and receiving blowjobs, getting my tight ass pounded, and making sure you have mul...
  • Hot Shemale in Boston Looking for FunHot Shemale in Boston Looking for Fun Hey there, I'm Mandie, a sexy shemale from Boston 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. When it comes to sex, I'm versatile and enjoy both giving and receiving. Whether you want me to be your top o...
  • Spark Some Magic with Gabbie from Boston!Spark Some Magic with Gabbie from Boston! Hey there, I'm Gabbie, a fun-loving transgender woman from Boston, Massachusetts. I may not fit society's norms, but I embrace every part of who I am with pride. Being part of the LGBTQ community has taught me the importance of self-love and acceptance. I enjoy exploring new places in the city li...
  • 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 ...
  • Raunchy Shemale Moira Ready to Play in BostonRaunchy Shemale Moira Ready to Play in Boston Are you a man looking for a wild time with a hot shemale? Look no further, because I'm here to fulfill all your dirty fantasies. My name is Moira and I'm a sexy shemale from Boston, Massachusetts seeking a local man for some mind-blowing sex and fun. I love getting down and dirty in the bedroom,...
  • Looking for Love and Adventure in Boston! 💖Looking for Love and Adventure in Boston! 💖 Hey there, lovely people of Boston! My name is Tamra, and I'm a fun-loving transgender individual ready to embark on an incredible dating journey. 🌈 So, let me tell you a little bit about myself. I have a curvaceous body that's perfect for cuddling up with on those chilly New England nights. A...