Boston, Massachusetts Shemale Dating Classifieds
Boston, Massachusetts shemale dating classifieds. Meet local crossdressers, transexuals and shemales for romance, sex or just make new transgender friends. escorts, body rubs & sex service listings. Select your location below to find shemales near you. It's free to search or post your own ad!
Home / Shemale Dating /
Show Ads In: Boston | Cape Cod / Islands | South Coast | Western MA | Worcester / Central MA
April 4th, 2025
M-F trans woman wants a date I want someone understanding and kind. Please check out my profile and rate me. I am 36, 5 feet 6 and elegant! My name is Lyssa....
Seeking All TS Beauties in Boston I am a masculine, dominant, and very passionate man, and I am looking for a sensual and seductive TS woman to explore our deepest desires together. No matter whether you like to be the boss or to be taken care of, I am all about creating electric chemistry and unforgettable moments...
TS Latina Goddess β For Men Who Crave Passion, Fire & Pleasure π₯π Hello sweetheart π The TS Latina bombshell body type defines me through my soft lips and thick thighs and my hidden surprise under red lace. Your pleasure stands as my life purpose because I want to satisfy your desires and make your body experience intense pleasure through my s...
TS Latina Bombshell β Your Secret Addiction, Your Midnight Obsession ππ Hola, mi amor π
The fiery, curvaceous TS Latina body I possess was made for lust while my soul demands intense passionate nights. Your dream woman has arrived because I possess caramel skin and thick thighs and long hair and soft lips and a throbbing surprise between my legs th...
TS Bombshell Looking for a Man Who Can Keep Up! π Boston Naughty, Nice and Looking for a Thrill!Transsexual Seeking Man for Sexy Fun!
View More of My Pictures πΈ
Are you the sort of man who enjoys just a touch of danger, a touch of excitement, and a lot of passion? I’m the trans beauty you’ve been dreaming of — sexy...
Tainted Love - Beyond Compare! Kinky Trans Woman in Boston
Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Boston. What kind of kink? You'll have to contact me to find out. I'm open to all sorts of fetish play if you are. I need a hookup with an open minded man. The sort of man who appreciates what I ...
Elisabeth 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 @...
TS BeautiesβLetβs Have Some REAL Fun! ππ₯ I am a tall, fit, and successful man and I have a taste for gorgeous TS women who love to be adored, desired and pleasured. Whether you are looking for a wild night, a passionate escape or something ongoing, I know how to treat a woman right.
π Must have confidence, charm...
Transgenderπ’TINA TSππ Ready to play with a TGirl Tonight?
Hi babe, I'm Tina π I'm in Boston and ready to meeup and hookup in LA tonight.. Let's hang out and have some super sexy fun!! I really need to get out and have some fun. Come check out MY PROFILE, browse my pix, videos and send me a message now.. Let...
Brandi 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 naught...
Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice!
Hey boys, my name is LethaWeapon here in Boston and I got a BIG love gun to whip and pound you with until you scream! I'm def top and alpha and don't take no shit! Imma make you suck me first just for foreplay then I'll throw you back for some hard insertion, ...
Letβs Play a GameβWinner Gets Me π Boston Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. π I’m the trans woman you’ve been dreaming about—sexy, confident, and oh-so-willing to turn up the heat. Let’s start slow… a few drinks, a little teasing, some whispers abo...
I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Boston
I'm queen Delilah a trans woman here in Boston searching for her king. You'll get the royal treatment when you're with me honey! Just grab hold of my magic scepter and his majesty can have anything he desires. Imagine the intrigue and scandalous positions ...
Email Boston Shemalesβ€οΈβπ₯ I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck
Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
Sassy CD Looking for a Real Man ππ₯ A sweet, sexy and a little naughty crossdresser here, I like to play and flirt, and I need a strong man who knows what he wants. I enjoy the process of dressing up, teasing and bringing fantasies to life. If you are into sensual encounters and passionate fun then let me and y...
I Need a STEAM ROLLER Baby!!! I want you to inject my soul with that sweet lover's pole till there ain't much of me left behind. I'm your whore so just F my brains out tonight. I'm a naughty trans looking for a top big boy to have his way with me. So it's heels and ass up and earth moving sex the hard way. That's the way I like ...
Email Local Shemales Now! π Want to Hookup and Find Local Shemales? RADE PIX - MESSAGE - BROWSE PROFILES
This Website Helps you find local shemales and TGirls meet local men. It's the perfect place to find what you'reinterested in π.. Do you want to meet local shemales who want to fuck and have some sex...
Seeking a Stunning TS for Passion & Pleasure ππ₯ I am a confident, strong and open minded man, who knows what I want from a woman – a sexy, elegant and fun loving TS woman to share unforgettable moments with. I am here to explore and enjoy every second of it, whether it is a casual hookup, a fun date or a deep connect...
Selena Trans girl cute looking for love Hello boys. I am looking for love. You want meet me? I want meet you too. See my pictures and send message for date....
I Need a Sexy Man to Tame Wild Willy! Hung Boston Trans Woman
Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Boston with a big wild willy that always seems act out in inappropriate ways at the worst times. For instance I'll be relaxed, minding my own business at my favorite Starbucks and see a be...
Letβs Get a Drinkβ¦ and See Where It Leads π One Night, No Limits... BostonShemale Seeking Man for sexπ¦
View More of My Pix - β
Some nights are for breaking rules, for letting go, and for indulging in pure pleasure. I am a trans goddess with a wild side, and I am looking for a man who wants to play. We shou...
Tiffany Shelle - Your Boston Tranny Girlfriend! π Tranny Escort - Top/Bottom/GFE in Boston
It’s Tiffany Shelle your perfect tranny girlfriend π₯° π SAFEπ π― LEGIT β¨π SKILLED, Exotic and Erotic π¦ π₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!
I'm 100% functioning...
Penny for your thoughts? Penny TS in Boston
Hey, I am Penny! I am recently new here and I am non op switch with a pretty nice pair, both top and bottom! Send me a message online!!
I'm looking for a nice man who will enjoy being with me. Let's enjoy hot dates and explore sexuality together. If that sounds interesting hit m...
Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Boston who doesn't smoke, but has a thing for sexy men smoking cigarettes. Call it a fetish or a kink if you will, but I love it. If done right it is soo sexy and inviting to my senses and gets my motor running every time. Truth is that it's erotic all in it's ...
Looking for a TS Woman Who Loves to Be Desired π¦π₯ Boston Male Seeking Transsexual for fun and whatever else!! I am a charming, confident and masculine guy and I have a special interest in beautiful TS women. I would be happy to meet anyone who wants to have fun, enjoy and indulge in the process. π I would love to meet a shemale or tra...
Beautiful Krystale 25 Boston visiting now Beautiful Shemale Visiting Boston
Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me.
Krystale25shemale
Age: 25
Location: Boston
Sex: Shemale
Seeking: Man
...
!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Boston
Meet sexy shemales ready to have some adult fun with their admirers.
Over 1,240 t-girls in Boston to heat up your love life tonight!
Join free for instant access to their sexy profiles and chat.
View: Explicit Shemale Photos
Enjoy 24/7 Online Chat
Mak...
New 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...
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Boston boos out there. I'm a sexy trans woman currently living in large and lovin' every second of it. Hit me up cause I Wanna ROCK too! I'll show you what a real woman can do and everything you don't know now. I'm sexy...
Spicy πΆ Latina Shemale in Boston Ready to Fill You ππ LATINA SHEMALE SEEKING π₯πΆ
Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Boston. Don't look any further, because I'm here to make all your wet dreams come true. My name is MARIA TS and I am a pre-op transgender woman who loves to...
Shemale 4 Men ππ¦ Boston Ready Now!! Come Closer, I Don’t Bite, Unless You Do Enjoy Itπ
View My Private Pictures -
If you’re looking to mess around… I don’t know, maybe in a way that’s a bit spicy for the two of us? I’m a trans beauty with a dirty mind and I love...
SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT! SHEMALE HOOKUPS
"The girl with a naughty little secret in her panties!"
SIGNUP FREE: INSTANT ACCESS! Shemale Profiles
Uncensored Photos
Swap Your Pics
Live Web Cams
Private Messages
Sext & Hook Up!
Join free for Instant Access to the Shemale Profiles
...
British T-girl Seeking Classy Gentleman in Boston... I am Lacy, a white, blonde haired, trans woman, 30 years old, 5'9, 160 pounds, from Manchester, England and need a man who is educated, refined and handsome. I have just relocated to Boston and am financially independent and looking for a gentleman who is like-minded, equally solvent and has excepti...
TS BeautiesβLetβs Make Some Memories πβ¨ I am a dominant, attractive, and confident man looking for a beautiful transgender woman who enjoys being admired, spoiled, and pleasured. I am down for mutual attraction, passionate flames and unforgettable moments. Whether it is a one time or if it is something on going I a...
Superb Shemale in Boston... T-Girl for NSA Encounters in Boston
When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Boston. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondle, f#ck and do...
Trans Playmate Sex Kitten... Ebony trans woman in Boston wants to be your sex kitten and playmate so let's make a playdate! I love all men so any race or body type or political side is fine with me. I can get along with anyone and we're gonna have a great time. I do all men, gay, bisexual, bicurious, swingers and groups. I am a...
π Discreet, Naughty & Waiting for a Man Who Can Handle Me π₯ I’m an exotic ebony TS bombshell in Boston with a love for steamy nights, deep connections and uninhibited pleasure, keep it hot and wild and unforgettable! Whether you are looking for an exciting adventure, a sensual night of passion or just something you’ve never...
π€ Ebony TS Playmate with a Curvy Body & a Wild Side π Boston π Thick thighs, soft lips, and a wild side—what more could you want? I’m a sensual, passionate ebony TS beauty who knows how to make a man feel special, desired, and completely satisfied. Whether we take it slow and intimate or dive into a steamy, no-strings-attached night of passion,...
π« Dark Chocolate Delight Ready to Melt in Your Arms π π Hey, Handsome! I’m a sultry, curvy ebony TS here in Boston... I'm Pre Op, ready to play, with a body made for pleasure and a heart full of passion. Discreet, sensual, and looking for a man who knows how to handle me. Let’s make tonight unforgettable! π I'm writing this to s...
TS Latina Dream Girl β Ride Me Like a Telenovela ππΊ Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual secret? That’s me, papi π I’m your spicy TS novela — dramatic, passionate, and unforgettable in the bedroom. Message me here babe -
I want your hands on my h...
BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK ππ BBC SHEMALE - BLACK TRANSπ let's play with each others cocks!
Hey there boo thang, I know you're going to like what you see. Shiit, I have something for you baby. I love being feminine and sexy. I do still have my penis and I love to use it. I want to see your mouth on it infact.. Would you...
SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Boston Secret Crossdressing Hookups in Boston
Hey there. I'm Sam (Samantha when dressed up). If you're reading this ad you may be a crossdresser who needs to let your feminine side out to play. Me too! If you're in the closet or married, it's no problem. I live alone, have a nice, home with a private gara...
TRANSGENDER LADYβ€οΈsexy hookups Transgender HOOKUPSin BOSTON MASSACHUSETTS
Direct Message MeI'm in the Boston Massachusetts.. area. I'm willing to travel. As longas you love TRANSSEXUALS.. I want toshow you my Tranny peepee and I wantto see yours. What would you do with my cock right this second babe? I know...
THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! π
My name is Frank and I'm here to see if I can find any transgender ladies who wants a real man to treat them right.. I'm living in xxxx but I'm willing to travel. I have a great house we can have some fun in as well. I have a HOTTUB, arcade, th...
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...
Ebony Shemale in Boston β€οΈπ Seeking Male for Naughty Fun! Ebony Shemale Stefanie Ready to Fulfill Your Wildest Fantasies π
Are you looking for a hot and kinky black shemale in Boston? Look no further because I am here to satisfy all your desires. My name is StefanieBBC and I'm an Ebony Shemale.. I am a stunning transgender woman who loves to play...
Sexy Shemale Boston I know You Want to Play FEMININE AND SECURE SHEMALE
Hot and kinky shemale seeking a hot and fun guy who isn't scared of a beautiful and secure Trans Woman.. I'm located in Boston; I am AlaneTS and I am here to fulfill all your desires. If you are in the area or planning to be. and looking for a hot and k...
Boston Addicted to shemales... Male Seeking TS A handsome, fit and confident man, seeking a stunning TS girl to spend exciting nights and incredible moments with. I have a thing for flirty conversations, passionate chemistry and playful antics- if you are looking for a casual meet or if we can make this a more regular thing, I ...
I'm a Horny Shemale ππ Looking For Sex Tonight!! Sexy Shemaleπ Ready to Rock Your World!
Local Transsexual - TGIRL Sext App π²
I'm a Transgender and I'm looking for a naughty man with a nice cock here in near me.. Who is wanting to share some sexy fun with me. I've been really horny and hard!! I love taking cock and giving it, what are...
TS Latina Bombshell Craving a Real Man to Handle Her ππ₯ Hola, papi π You are my TS Latina fantasy because I carry your weight in all the right places and your softness in all the other places and my body is made for late nights and louder moans. My skin is golden, my tongue is bilingual, and my hips don’t lie... especiall...