Cape Cod / Islands, Massachusetts Shemale Dating Classifieds

Cape Cod / Islands, 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!

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  • July 14th, 2025
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Cape Cod / Islands Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Cape Cod / Islands Seeking!! Seduction Starts with One Look…Once I have your attention, baby, I don’t let go. 😏 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...
  • Email Local Shemales Now! πŸ’ŒEmail Local Shemales Now! πŸ’Œ 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 πŸ˜‰.. Do you want to meet local shemales who want to fuck and have some sex...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Cape Cod / Islands 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 ...
  • TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯TS Beautiesβ€”Let’s Have Some REAL Fun! 😏πŸ”₯  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. πŸ’‹ Must  have confidence, charm...
  • πŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle MeπŸ’– Discreet, Naughty & Waiting for a Man Who Can Handle Me  πŸ”₯ I’m an exotic ebony TS bombshell in Cape Cod / Islands 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&rs...
  • Transgender🟒TINA TSπŸ˜‰πŸ’‹ Transgender🟒TINA TSπŸ˜‰πŸ’‹ Ready to play with a TGirl Tonight? Hi babe, I'm Tina πŸ’‹ I'm in Cape Cod / Islands 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 messa...
  • A monster in the sheets, but a lady in the streets...A monster in the sheets, but a lady in the streets... Hello men, I'm Lilith a 27 year old sexy femme, fully functional, passible, sexy and hot to trot trans. I can be a bit racy and dirty when it's appropriate, but always maintain my poise in public. If you live in the Cape Cod / Islands area and are interested then drop me a line and introduce yoursel...
  • I want to be a whoreI want to be a whore I am a transexual very hot. Good with my mouth and my ass. Comment on my photos. I would appreciate it if you downloaded my photos and share me with other men in the Cape Cod / Islands area. Click here and come see me anytime!...
  • πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best πŸ˜πŸ’¦ Thick, Juicy & Kinky – Come Experience the Best 😏  πŸ”₯| Do you feel that you want something new and exciting and that you want to  remember for a long time? I am a hot, all natural ebony TS with all the right amount  of curves and a naughty and adventurous spirit. I don’t just know how to tease, please and  make you want ...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Cape Cod / Islands 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 gr...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Cape Cod / Islands. Sheila wants to meet you. Hey all, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, top or bottom, love oral sex. Want to explore kinks? Me too!! Want to meet me? Send me a message @HotTransChi...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Cape Cod / Islands Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Cape Cod / Islands. 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...
  • Cape Cod / Islands πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Cape Cod / Islands πŸ˜ˆπŸ†πŸ’¦ Latina Shemale is Seeking a Real Man!! Real Latina TS Seeking πŸ”₯Ready to Fulfill Your Wildest Fantasies  My Spicy Latina Shemale Pix! -Are you looking for a sexy shemale to play with? I'm a bit of a drama queen. I love dressing pretty and getting my nails done. I will also dress sexy in lingerie for you. Do you want to have a hoo...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Cape Cod / Islands Sandi wants to meet hot guy for fun and hot sex. Age 28, nice build, 7.5". Non op functional. Love oral sex, anal sex and kinks of all sorts. View my profile and message me here @SandiSwitchTS...
  • July 13th, 2025
  • Hot sexy shemale doll visiting Cape Cod / Islands now Hot sexy shemale doll visiting Cape Cod / Islands now Shemale Visiting Cape Cod / Islands Very hot sevy and curvy shemale chick with 8 inch lady stick. Message me on my profile page @TaylaShemale1. Seeking kind gentleman for romance and fun. Possible long term with the right man. ...
  • TS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“ΊTS Latina Dream Girl – Ride Me Like a Telenovela πŸ˜ˆπŸ“Ί  Have you ever imagined a sensual Latina woman with large thighs and a narrow waist and a hidden sexual  secret? That’s me, papi 😘 I’m your spicy TS novela — dramatic,  passionate, and unforgettable in the bedroom. Message me here babe - I want your hands on my h...
  • YOUR EBONY SHEMALE - big boobs and a BIG COCK! Cape Cod / IslandsYOUR EBONY SHEMALE - big boobs and a BIG COCK! Cape Cod / Islands Hot Hot Hot! Sinead, a black shemale in Cape Cod / Islands ready to make all of your  wildest fantasies come true! πŸ’‹πŸ”₯ My Pictures and Profile! -- You want to find a sexy ebony shemale in  Cape Cod / Islandsto fulfill all your dreams? Then stop searching because I am ready to make &...
  • Do you know the difference between a dick and a bucket of popcorn?Do you know the difference between a dick and a bucket of popcorn? You don't know? Well then take me to the movies baby! Mmmm think of all that creamy, buttery, salty goodness! Talk about a double feature. lol Hope you have the munchies for this hot Cape Cod / Islands tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and ...
  • TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯TS Latina Fantasy Girl – Let Me Rock Your World πŸ’‹πŸ”₯  Mira, papi… I’m not just sexy — I’m dangerous 😘 ( View My Dating Pictures Here ) My  TS Latina body features silky skin and long hair and full lips and a tight and juicy physique. I  dress to kill. My moans produce musical sounds. My movements flow throug...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Cape Cod / Islands Tammy, 39, 38DD, 9" and so cute!! What more could you want in a gurl?!! How about you message me @Tammy38DD and we can talk and meet! Send your recent pic for mine....
  • New Body New MeNew Body New Me M2F post-op in Cape Cod / Islands 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&n...
  • F/M seeking love and funF/M seeking love and fun Female to Male Trans Man in Cape Cod / Islands 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...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Cape Cod / Islands Look no further honey, I'm Franny an Ebony trans woman here in Cape Cod / Islands to fulfill your wildest fantasies. Dreams really do come true when you are with Fabulous Franny. I'm all about the frills and the thrills baby! We can freak it a...
  • TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨TS Beautiesβ€”Let’s Make Some Memories πŸ’–βœ¨  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...
  • FtM seeking Princess Bride in Cape Cod / IslandsFtM seeking Princess Bride in Cape Cod / Islands FtM seeking Woman in Cape Cod / Islands Hi, I'm Andy, age 33, FtM transgender man living in Cape Cod / Islands. 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 m...
  • DonDon't Worry I Bite! Feisty redhead trans in Cape Cod / Islands full of fun and loves it rough on the bottom. I'm 5'9, 170 pounds, 32 years old, well endowed, fully functional, passible and hot to trot. You can take me anywhere, but I can't promise to always behave. I have a dirty mind and when the urge hits it's hard t...
  • Well Endowed Shemale is beautiful Cape Cod / Islands 32Well Endowed Shemale is beautiful Cape Cod / Islands 32 Well Endowed Shemale in Cape Cod / Islands I am Blanca. I am ready to eat your manhood now. Top or bottom. Bareback if you're clean. Come say hello. I'm friendly, sexy as hell and always satisfy my partner. Give me a try. Message me at BlancaShemale32 for my latest pictures and proof of m...
  • Shemale 4 Men πŸ†πŸ’¦  Cape Cod / Islands Ready Now!! Shemale 4 Men πŸ†πŸ’¦ Cape Cod / Islands Ready Now!!  Come Closer, I Don’t Bite, Unless You Do Enjoy ItπŸ˜‰   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...
  • BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰BIG BOOBS, BIG LIPS, THICK THIGHS... BIG COCK πŸ†πŸ˜‰ BBC SHEMALE - BLACK TRANSπŸ’Ž 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...
  • INTERACTIVE MAP: Transexual Tracker in the Cape Cod / Islands Area!INTERACTIVE MAP: Transexual Tracker in the Cape Cod / Islands Area! Local Transexual Hookups Meet local transexuals in the Cape Cod / Islands area. View our interactive map below to meet local trans hookup members who are seeking dating or sex hook ups. Click any thumbnail below to begin your search. Interactive Cape Cod / Islands Trans Hookups Map ...
  • MALE SEEKING SHEMALE πŸ†Cape Cod / Islands Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Cape Cod / Islands Ready to Play and Fuck πŸ’¦ I have a secret.. 🀫 I've always want to see what it's like to play with a shemale!!  Hi I'm John, I'm in Cape Cod / Islands  and I love to be free and have fun.. Are you looking for a man who really knows how to treat you?? I really want to show you what I got sweetie. I have a go...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Cape Cod / IslandsSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Cape Cod / Islands Secret Crossdressing Hookups in Cape Cod / Islands 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 ...
  • THE RIGHT GUY FOR THE JOB!!!THE RIGHT GUY FOR THE JOB!!! IF YOU'RE TS/SHEMALE.. I'm The Guy for you!! πŸ˜‰ 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...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Cape Cod / Islands 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 inter...
  • Dr FreakinDr Freakin'furter - Mine's Bigger Than Yours! White T-girl here and I'd bet mine is bigger than yours. We'll just let it be our little intimate surprise when the time comes. No one needs to know our business, Let's just keep it discreet. If you live in the Cape Cod / Islands area come see if you measure up! Click here for explicit photos.&...
  • I Need a STEAM ROLLER Baby!!!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 ...
  • Cape Cod / IslandsCape Cod / Islands's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Cape Cod / Islands Hi you sexy man! I'm Toni a trans woman from here in Cape Cod / Islands. Looking forward to a fun, sexy evening with you tonight. Let's make some memories that we'll never forget! I'm a 28 year old redhead tgirl who's passionate, warm, funny, hung...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Cape Cod / Islands I'm queen Delilah a trans woman here in Cape Cod / Islands 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 a...
  • Looking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ Cape Cod / IslandsLooking for a TS Woman Who Loves to Be Desired πŸ’¦πŸ”₯ Cape Cod / Islands  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. πŸ’‹ I would love to meet a shemale or tra...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Cape Cod / Islands Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Cape Cod / Islands to heat up your love life tonight! Join free for instant access to their sexy profiles and chat. View: Explicit Shemale Photos Enj...
  • British T-girl Seeking Classy Gentleman in Cape Cod / Islands...British T-girl Seeking Classy Gentleman in Cape Cod / Islands... 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 Cape Cod / Islands and am financially independent and looking for a gentleman who is like-minded, equally solvent and...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Cape Cod / Islands area and want to make some new friends! I am a masseur, hot body and hung. If you want to get together, Send me a private message Crystal27trans <3 ...
  • πŸ‘ Your Secret Ebony Fantasy Is Just One Message Away πŸ˜œπŸ‘ Your Secret Ebony Fantasy Is Just One Message Away 😜  πŸ‘„ I am going to make your wildest dreams come true. I am a classy  yet freaky ebony trans beauty that loves to explore deep desires and steamy fantasies. If you are  a man that appreciates soft skin, full lips and a body made for pleasure then we need to  talk. If you are loo...
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Cape Cod / Islands 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...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Cape Cod / Islands Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Cape Cod / Islands 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 favorit...
  • Hi Guys!! I am looking for someone fun!Hi Guys!! I am looking for someone fun! This is Lara and I am 41 and transitioned when I was 24. I pass exceptionally well and you will be surprised at my hidden skills. Call me! ...
  • II'm the Girl Mother Never Warned You About!... But then, how could your mother have known? I'm Dirty Diana corrupting good decent honest men like yourself here in Cape Cod / Islands for many moons. I got a big secret and it's show and tell time baby! It's easier to show you than to tell you. I'm fully functional and passible. I need a sexy man w...
  • TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹TS Latina Snack – Sweet Like Sugar, Dirty Like Tequila 😘🍹  You can find me at the bar where I serve drinks and flirt with customers while enjoying the  atmosphere. I’m your sexy little TS Latina snack — soft lips, juicy thighs, and a tongue that  doesn’t stop until you beg me to πŸ’‹ I’ll start off sweet, flirty, &nbs...
  • Superb Shemale in Cape Cod / Islands...Superb Shemale in Cape Cod / Islands... T-Girl for NSA Encounters in Cape Cod / Islands When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Cape Cod / Islands. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to fl...
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