Pittsburgh, Pennsylvania Shemale Dating Classifieds

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  • December 21st, 2025
  • Elisabeth waiting to be your QueenElisabeth waiting to be your Queen TRANSEXUAL FOR MAN IN THE Pittsburgh 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 Messa...
  • 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 Pittsburgh 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...
  • HOT SHEMALE GIA will Satisfy Your Tranny Fantasy \ Pittsburgh!HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Pittsburgh! 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 Pittsburgh!  No strings - just great times, so join my page free for instant access! Shemale Gia's Pittsburgh Sexbook @ShemaleGia27 Photos:...
  • Free Pennsylvania Transexuals GuideFree Pennsylvania Transexuals Guide Pennsylvania Transexuals Guide The Pennsylvania 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 Pennsylvania Transexuals Guide online.  Where to Meet Transex...
  • Erotic exotic Asian queen in Pittsburgh now (25)Erotic exotic Asian queen in Pittsburgh now (25) Asian Transexual in Pittsburgh Stunning TS - Talia 25. 5' 8" 140lbs, non op, loves sex. Long slender legs to wrap around you. Message me @TaliaAsianQueen for my photos and contact information....
  • 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 P...
  • DonDon't Worry I Bite! Feisty redhead trans in Pittsburgh 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 contro...
  • MALE SEEKING SHEMALE πŸ†Pittsburgh Ready to Play and Fuck πŸ’¦MALE SEEKING SHEMALE πŸ†Pittsburgh 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 Pittsburgh  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 good heart...
  • Beautiful Krystale 25 Pittsburgh visiting nowBeautiful Krystale 25 Pittsburgh visiting now Beautiful Shemale Visiting Pittsburgh 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: Pittsburgh Sex: Shemale Seeking: Man ...
  • Tiffany Shelle - Your Pittsburgh Tranny Girlfriend! πŸ’žTiffany Shelle - Your Pittsburgh Tranny Girlfriend! πŸ’ž Tranny Escort - Top/Bottom/GFE in Pittsburgh It’s Tiffany Shelle your perfect tranny girlfriend πŸ₯° πŸ’• SAFEπŸ’• πŸ’― LEGIT βœ¨πŸ’ž SKILLED, Exotic and Erotic πŸ’¦ πŸ₯° I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% functio...
  • INTERACTIVE MAP: Transexual Tracker in the Pittsburgh Area!INTERACTIVE MAP: Transexual Tracker in the Pittsburgh Area! Local Transexual Hookups Meet local transexuals in the Pittsburgh 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 Pittsburgh Trans Hookups Map ...
  • Sexy Shemale Pittsburgh I know You Want to Play Sexy Shemale Pittsburgh 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 Pittsburgh; 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 a...
  • !!!HOT - TRANS FUCKBOOK - HOT!!!!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Pittsburgh Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Pittsburgh 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 C...
  • 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 Pittsburgh tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longer t...
  • Looking for My TS Queen πŸ‘‘πŸ’‹Looking for My TS Queen πŸ‘‘πŸ’‹ I’m a confident, successful, and open-minded man looking to connect with a beautiful TS woman for fun, passion, and maybe something more. πŸ’• I appreciate a woman who knows her worth and loves to be treated right. Whether it’s a romantic dinner, steamy nights, or spontaneous adventures,...
  • Flawlessly gorgeous trans bombshell in PittsburghFlawlessly gorgeous trans bombshell in Pittsburgh Trans MtF for Man in Pittsburgh I transitioned 6 years ago at the age of 18. I am gorgeous, with long light brown hair, hour glass figure and long shapely legs. I am 5 feet 7 and have deep blue eyes and luscious lips. Check my profile pics @TransFaye24 pics and prepare to be stunned! Send you...
  • PittsburghPittsburgh's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Pittsburgh Hi you sexy man! I'm Toni a trans woman from here in Pittsburgh. 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...
  • December 20th, 2025
  • Let’s Get a Drink… and See Where It Leads 😘Let’s Get a Drink… and See Where It Leads 😘  One Night, No Limits...  PittsburghShemale Seeking Man for sexπŸ’¦ View More of My Pix - βœ… 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 ...
  • 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 ...
  • Crystal, 27 New to the areaCrystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Pittsburgh 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 ...
  • 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...
  • Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Pittsburgh Seeking!!Let’s Play a Gameβ€”Winner Gets Me πŸ˜‰ Pittsburgh 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...
  • 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...
  • Penny for your thoughts?Penny for your thoughts? Penny TS in Pittsburgh 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 h...
  • TS Asian lady ready for upscale action (28)TS Asian lady ready for upscale action (28) Asian Transexual Lady for Man in Pittsburgh Hot and sexy Asian transexual, fully functional and wants to play with you! Message RubyTS4male...
  • Debonair Trans dude, looks like BondDebonair Trans dude, looks like Bond F2M Trans Dude in Pittsburgh 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...
  • Your Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ PittsburghYour Flirty CD Sweetheart Awaits πŸ’•πŸ˜˜ Pittsburgh I am a  hot, cool and confident crossdresser who enjoys the feeling of being wanted, loved and taken care  of like a lady. Whether you are looking for some hot action, a nice relationship or even a  friend with benefits, I am here to make it unforgettable. πŸ’‹ πŸ‘  Feminine, fun and ...
  • TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘TS Latina Bombshell – Your Secret Addiction, Your Midnight Obsession πŸ˜ˆπŸ‘  Hola, mi amor 😘 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...
  • 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 and send message for date....
  • 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! ...
  • SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in PittsburghSECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Pittsburgh Secret Crossdressing Hookups in Pittsburgh 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 ...
  • II'll Make You Feel Like a King Baby! Trans Queen Seeks King in Pittsburgh I'm queen Delilah a trans woman here in Pittsburgh 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 po...
  • 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 Pittsburgh 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 na...
  • 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...
  • 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...
  • TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘TS Latina Seductress – Thick, Wet & Ready to Be Used πŸ’‹πŸ‘  Papi… I’ve been thinking about you 😘 View More Sexy TS PIX - My curvy figure and thick TS  Latina body has caramel skin while my filthy mind and mouth were made for you 😈. I become  submissive only when you want me to submit while I transform into a dominant forc...
  • Superb Shemale in Pittsburgh...Superb Shemale in Pittsburgh... T-Girl for NSA Encounters in Pittsburgh When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Pittsburgh. 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#c...
  • 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 Pittsburgh area come see if you measure up! Click here for explicit photos. Loo...
  • Spicy 🌢  Latina Shemale in Pittsburgh Ready to Fill You πŸ˜‰πŸ˜‰ Spicy 🌢 Latina Shemale in Pittsburgh Ready to Fill You πŸ˜‰πŸ˜‰ LATINA SHEMALE SEEKING πŸ”₯🌢  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Pittsburgh.  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 love...
  • Hot sexy shemale doll visiting Pittsburgh now Hot sexy shemale doll visiting Pittsburgh now Shemale Visiting Pittsburgh 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. ...
  • FtM seeking Princess Bride in PittsburghFtM seeking Princess Bride in Pittsburgh FtM seeking Woman in Pittsburgh Hi, I'm Andy, age 33, FtM transgender man living in Pittsburgh. 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 @And...
  • TS m/f switch 28 new hereTS m/f switch 28 new here TS m/f Switch in Pittsburgh 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...
  • Hot Shemale in Pittsburgh Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ†Hot Shemale in Pittsburgh Ready to Fulfill Your Wildest Fantasies πŸ‘„πŸ’¦πŸ† I'm TS and Looking to Date in Pittsburgh My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Pittsburgh who knows how to have a good time? Look no further, because I'm here to make all your dreams come true. I'm really excited about possibly meeting some like minded people and...
  • πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹πŸ‘  Classy on the Streets, Naughty in the Sheets – Let’s Play πŸ’‹  πŸ’– Just one taste and you’ll be addicted! I am a beautiful, funny TS,  a queen of color with a nice curvy body, beautiful eyes, and a touch that will drive  you crazy. I know what a man needs and how to make him satisfied and craving for more.  I am looking for a confide...
  • One Night, No Rules, Just Pleasure… One Night, No Rules, Just Pleasure… Pittsburgh I'm Having a Night to Myself No Strings, just fun.. TS Seeking...🀫  A man who knows what he wants, but also a man who can be tempted, that’s  what I like.  We should begin with eye contact, a slow touch, and perhaps truth or  dare while drinking cocktail...
  • Local Crossdresser πŸ˜‰πŸ˜‡  LET ME PLAY DRESSUP FOR YOULocal Crossdresser πŸ˜‰πŸ˜‡ LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Pittsburgh View My Personal Pix - 🀫  A sexy Crossdresser from Pittsburgh, here, and her name is  KaralynnCD. I am pre-op but that has not stopped me from enjoying all the benefits that come with being  a Crossdressing Trans woman. If you like dirty g...
  • Trans Playmate Sex Kitten...Trans Playmate Sex Kitten... Ebony trans woman in Pittsburgh 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 ...
  • Superior Massage by gorgeous T-GirlSuperior Massage by gorgeous T-Girl T-Girl for Dating in Pittsburgh 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: Gayle...
  • Shy Transexual Escort inΒ PittsburghShy Transexual Escort inΒ Pittsburgh Shy transexual Camille here to tease you with my long functioning lady stick. Age 24, slim, healthy and physically fit. I love sex! I do top or bottom, special attention to your needs. Kink friendly so let me know what you like. I love it all. Explore your passion for trans women discreetly with an ...
  • Hot trans chick with nice boobsHot trans chick with nice boobs Hot trans chick in Pittsburgh. 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 @HotTransChick...