Catskills Transgender Classifieds

Browse Catskills transgender classifieds to meet local transexuals, crossdressers and shemales for sex, dating or friendship. Contact any of these trans advertisers to swap pics and contact info. Chat online or text and arrange real-time sex hookups if you feel a connection. It's free to search all trans classifieds, or post your own adult ad!

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  • July 7th, 2025
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Catskills 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 a...
  • Twisted Sister - Loves to Ride.... and be Ridden!Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Catskills 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 s...
  • Erotic exotic Asian queen in Catskills now (25)Erotic exotic Asian queen in Catskills now (25) Asian Transexual in Catskills Stunning TS - Talia 25. Asian mixed race, non op, loves sex. Nice build with long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information. Classy in public but trashy in the bedroom. Versatile and attentive to your needs. Long...
  • July 6th, 2025
  • Trans Man waiting for right date with hot beautyTrans Man waiting for right date with hot beauty Handsome Trans Man for Dating in Catskills 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!&...
  • Letha Aims to Fill YOU With Her Love Gun!!!Letha Aims to Fill YOU With Her Love Gun!!! Trans Woman Needs U 4 Target Practice! Hey boys, my name is LethaWeapon here in Catskills 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 insertio...
  • Hot sexy shemale doll visiting Catskills now Hot sexy shemale doll visiting Catskills now Shemale Visiting Catskills Very hot sevy and curvy shemale chick with big delicious lady stick, fully functions for top or bottom. Message me on my profile page @TaylaShemale1. Seeking a kind gentleman for romance and fun. I adore introducing men who are new to shemale sex. HMU! Possible long...
  • Smoke me out baby!Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Catskills 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...
  • TGIRL๐ŸฅตCatskill, NYTGIRL๐ŸฅตCatskill, NY I'm a Pre-Op Transgender Lady Who is in need of some sex tonight in Catskill New York TGIRL Messanger๐Ÿ“ฒ in Catskill, NY I'm a Transgender lady living in New York,Catskill to be exact. I was born a man I lovebeing feminine and dressing all pretty. Do you want to meet a TG...
  • Latina TS Dirty Girl Looking for a GentlemanLatina TS Dirty Girl Looking for a Gentleman's Dark Side ๐Ÿ”ฅ๐Ÿ‘   Sweet on the surface. Filthy underneath. View My Trassexual Dating Profile Here - As a TS darling I present like a dream while  playing like a fantasy. Stockings. Heels. A tight dress. Soft skin. And a  throbbing surprise you’ll love exploring ๐Ÿ˜˜ I need you to undress me gr...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Catskills area and want to make some new friends! I am a masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Catskills, New YorkAg...
  • TS Temptress Ready to Ruin You (In the Best Way) ๐Ÿ˜ˆ๐Ÿ’ฆ CatskillsTS Temptress Ready to Ruin You (In the Best Way) ๐Ÿ˜ˆ๐Ÿ’ฆ Catskills  Hey lover ๐Ÿ˜˜ I’m a high-femme TS bombshell — curves for days, lips  made for kissing (and more), and a hunger that doesn’t quit. After dinner I appear sweet  but I transform into a woman who crawls to the bed naked while wearing only a mischievous  expression...
  • 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 ...
  • Tantalizing Tina with a HUGE W33NAH!Tantalizing Tina with a HUGE W33NAH! Catskills Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Catskills men and wnat to show you a time you'll never forget! Do you like them thick, long and uncut? Then I'm the girl for you. Look no further for a passible and functional t girl - HERE I AM!  About m...
  • Road Head Sally DrivinRoad Head Sally Drivin' Hard in Catskills Tonight! I'm Road Head Sally a horny t-girl for you busy guys on the go in Catskills. Hey, what's the best time for road head? When there's gas in the tank baby! Let's go for a wild ride your car or mine and let me treat you to Sally's specialty. I drive or you drive which ever you prefer. We can drive or pa...
  • Iโ€™m a Sexy and Naughty T-Girl Here in Catskills.Iโ€™m a Sexy and Naughty T-Girl Here in Catskills. Catskills T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Catskills area. Sweet, sexy, friendly and outgoing. I will definitely make you feel happy/sexy vibes and relaxed. I have an amazing body boys. I'm a pretty t-girl with a big present! So forget all your  worries an...
  • Ebony TS Playmate for Men Who Know What They Want ๐Ÿ–ค๐Ÿ†Ebony TS Playmate for Men Who Know What They Want ๐Ÿ–ค๐Ÿ†  If you are the type of person who does not want to waste time with games or small  talk… we are already off to a good start ๐Ÿ˜˜ I am a sexy, curvy TS  babe who loves attention, loves giving pleasure, and lives to be desired. I will come looking like  a dream and be read...
  • 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 Catskills tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer th...
  • Tainted Love - Beyond Compare!Tainted Love - Beyond Compare! Kinky Trans Woman in Catskills Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Catskills. 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 w...
  • Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates.Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Catskills Area Hi, my fem name is Gloria. I'm a married crossdresser in the Catskills area. I'm 28 years old, clean and disease free. I am passable in appearance and voice but my wife doesn't approve. I REALLY need to let my fem side out to play! I'm seeking cross dres...
  • July 5th, 2025
  • 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 Catskills area. Click here and come see me anytime!...
  • Beautiful Krystale 25 Catskills visiting nowBeautiful Krystale 25 Catskills visiting now Beautiful Preop Shemale Visiting Catskills Come and join me for a drink. I am lonely here in this new place. Dark olive skin, really beauty. Message me @Krystale25shemale.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Catskills, New York Sex: MtF Trans Seeking: Man ...
  • Black/Ebony Transsexual - Your New  Addiction โ€“ One Taste and Youโ€™ll Beg for More ๐Ÿ‘๐Ÿ’‹Black/Ebony Transsexual - Your New Addiction โ€“ One Taste and Youโ€™ll Beg for More ๐Ÿ‘๐Ÿ’‹  Warning: I’m addictive ๐Ÿ˜˜ View My Ebony TS Profile here - I possess more than attractive features. I am a complete  TS woman who enjoys teasing and pleasing while taking control of your dreams. My body features long legs and  thick thighs and soft lips and a hidden secret th...
  • I Need a Sexy Man to Tame Wild Willy!I Need a Sexy Man to Tame Wild Willy! Hung Catskills Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Catskills 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 se...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in CatskillsSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Catskills Secret Crossdressing Hookups in Catskills 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 g...
  • Selena Trans girl cute looking for loveSelena 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 @SelenaIsTrans and send me a message to set up a date. I like going out for food or drinks, having a great time and I especially like great sex! I am preop and can do top or bottom though I kind of prefer top ...
  • Superb Shemale in Catskills...Superb Shemale in Catskills... T-Girl for NSA Encounters in Catskills When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Catskills. 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 ...
  • II'm a Horny Shemale ๐Ÿ˜ˆ๐Ÿ’‹ Looking For Sex Tonight!! Sexy Shemale๐Ÿ’Ž Ready to Rock Your World! Local Transsexual - TGIRL Sext App ๐Ÿ“ฒ 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...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Catskills 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 @PennyTSswitch!! I'm a mixed race sweetheart, looking for a nice man who will enjoy being with me. Let's enjoy having some fun, hot dates and ...
  • II'm the Girl Your Mum 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 Catskills 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 who lives ...
  • Partners in crime, or?Partners in crime, or? Sexy, Slytherin, Aries, ISTP and more, if that gives you a hint about my personality traits. So, I’m a sexy, sensual, tender, animal loving, bookworm. I am a bit of a flirty whore, who loves mystical magical movies and stories, so let’s get that out in the open. If you live in the C...
  • Catskills๐Ÿ’‹ TS Tina โ€“ Your Naughty Escape, Anytime, Anywhere ๐ŸŒŽ๐Ÿ”ฅCatskills๐Ÿ’‹ TS Tina โ€“ Your Naughty Escape, Anytime, Anywhere ๐ŸŒŽ๐Ÿ”ฅ Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world ๐Ÿ˜˜ I possess the right amount of softness while maintaining the perfect playful demeanor and I always welcome men who understand how to treat a genuine wild wom...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy  Catskills!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Catskills! LET'S TAKE CARE OF THAT TRANNY FANTASY! "Experience your secret tranny desires in real life!"  Hot shemale Gia wants to hook up with you in Catskills!  No strings - just great times, so join my page free for instant access! Shemale Gia's Catskills Sexbook @ShemaleGia27 Photos: 4...
  • Having fun and Staying YoungHaving fun and Staying Young Young-ish trans fem looking for nice date with lady. I am kind and thoughtful and you will have a very good evening if I take you out. Let me know what you want to do or where you want to go. View profile @SherryTransFem33 and message me. Send your pics for mine. I'm hoping to find real chemistry an...
  • Tiffany Shelle - Your Catskills Tranny Girlfriend! ๐Ÿ’žTiffany Shelle - Your Catskills Tranny Girlfriend! ๐Ÿ’ž Tranny Escort - Top/Bottom/GFE in Catskills It’s Tiffany Shelle your perfect tranny girlfriend ๐Ÿฅฐ ๐Ÿ’• SAFE๐Ÿ’• ๐Ÿ’ฏ LEGIT โœจ๐Ÿ’ž SKILLED, Exotic and Erotic ๐Ÿ’ฆ ๐Ÿฅฐ I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% function...
  • TS Sugar Baby๐Ÿ’Ž Your Perfect Trans Fantasy โ€“ Letโ€™s Make It a Reality ๐Ÿ’‹TS Sugar Baby๐Ÿ’Ž Your Perfect Trans Fantasy โ€“ Letโ€™s Make It a Reality ๐Ÿ’‹  ๐Ÿ“ Location: Catskills ๐Ÿ’– Seeking: Fun, Exciting, &  Discreet Connections Some about me.. Trans SugarBaby: Hey there! I belive I'm a stunning, sweet, and playful trans beauty who loves good  vibes, great chemistry, and unforgettable nights.. I'm in my early 20's and I...
  • British T-girl Seeking Classy Gentleman in Catskills...British T-girl Seeking Classy Gentleman in Catskills... 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 Catskills and am financially independent and looking for a gentleman who is like-minded, equally solvent and has exce...
  • Well Endowed Shemale is beautiful Catskills 32Well Endowed Shemale is beautiful Catskills 32 Well Endowed Shemale in Catskills 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 @BlancaShemale32 with your recent pic or selfie for my latest pictures and ...
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Catskills 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 and show you wh...
  • July 4th, 2025
  • Flawlessly gorgeous trans bombshell in CatskillsFlawlessly gorgeous trans bombshell in Catskills Trans MtF for Man in Catskills I transitioned 6 years ago at the age of 18. I'm still fully functional but live 24/7 as a female. I pass flawlessly so let's go out on the town! I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am short and cute and I have bedroom...
  • DonDon't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Catskills Look no further honey, I'm Franny an Ebony trans woman here in Catskills 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 and they don't have...
  • 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 Catskills area and are interested then drop me a line and introduce yourself. You ca...
  • The Trevor Project Saves Young LGBTQ+ LivesThe Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Catskills Lesbian, Gay, Bisexual & Trans Dating Community The Trevor Project Donations, by Megan Morrison BonePage.com proudly supports The Trevor Project, an organization dedicated to suicide prevention among lesbian, gay, bisexu...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Catskills I'm queen Delilah a trans woman here in Catskills 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 posi...
  • DonDon't Worry I Bite! Feisty redhead trans in Catskills 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 to control...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Catskills. Sheila wants to meet you. Hey guys, I am Sheila and I am ready for a date! Blonde hair, nice boobs, good curves and very kissable lips. I'm pre-op, well endowed and functional, top or bottom. I love oral sex giving, receiving or 69. Want to explore kinks? Me too!! Want ...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Catskills Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Catskills 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 Cha...
  • CatskillsCatskills's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Catskills Hi you sexy man! I'm Toni a trans woman from here in Catskills. 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, functional and l...
  • Jasmin T-girl Ready to make friendsJasmin T-girl Ready to make friends Want to Meet a T-Girl in Catskills? Hey, I am Jasmin, with a great body and busty. Hit me up @SweetJasminT. I love tatts and I'm 420 friendly, down to party! Lets swap some pics and then meet up for a fun date and see where it goes! I'm preop and functional, very sex positive and love all sort...
  • Sexy hung and big bustedSexy hung and big busted Hung and Busty Shemale in Catskills Tammy, 39, big tits!! Well hung, everything works, clean and so cute!! What more could you want in a gurl?!! How about you message me @Tammy39T and we can talk and meet! Send your recent pic for mine. Username: @Tammy39TLocation: Catskills, New YorkAge...
  • Free New York Transexuals GuideFree New York Transexuals Guide New York Transexuals Guide The New York Transexuals Guide was prepared by our trans experts at AmericanTransexuals.com. We bring trans women and admirers together for friendship, dating and sex hookups. View our free New York Transexuals Guide online.  Where to Meet Transexuals in New ...