Winston-Salem, North Carolina Shemale Dating Classifieds

Winston-Salem, North Carolina 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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December 13th, 2025

🍫 Dark Chocolate Delight Ready to Melt in Your Arms 😘 💖 Hey, Handsome! I’m a sultry, curvy ebony TS  here in Winston-Salem... 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! 😘 I'm writing th...

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 ...

Flawlessly gorgeous trans bombshell in Winston-Salem Trans MtF for Man in Winston-Salem 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 ...

Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Winston-Salem? 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...

Beautiful Krystale 25 Winston-Salem visiting now Beautiful Shemale Visiting Winston-Salem 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: Winston-Salem Sex: Shemale Seeking: Man ...

F/M seeking love and fun Female to Male Trans Man in Winston-Salem 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 ...

Smoke me out baby! I'm a trans woman 37 years old, 5'9 in Winston-Salem 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 i...

Tainted Love - Beyond Compare! Kinky Trans Woman in Winston-Salem Hi I'm tgirl Trisha to show you boys a different kind of kinky love in Winston-Salem. 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 appre...

Local Crossdresser 😉😇 LET ME PLAY DRESSUP FOR YOU Your Sexy Crossdresser in Winston-Salem View My Personal Pix - 🤫  A sexy Crossdresser from Winston-Salem, 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 d...

Erotic exotic Asian queen in Winston-Salem now (25) Asian Transexual in Winston-Salem 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....

👑 Chocolate Queen with Soft Curves & Naughty Desires 🔥  🔥| 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 ...

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 W...

SECRET CROSSDRESSER? - Meet with Me for Discreet Dressing in Winston-Salem Secret Crossdressing Hookups in Winston-Salem 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 priva...

Brandi 27 tall slim hot trans chick 8.5 inch Pre-op TS, fully functional in Winston-Salem 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...

I LOVE DRESSING AS A SEXY WOMAN.. I want you to see me ( Winston-Salem ) Sexy Crossdresser Elissa Looking for Hot Fun in Winston-Salem💋    Do you like knowing I'm a man in womens clothes.. do I look sexy??    - VEW MY CD PICTURES Are you wanting to satisfy your innermost desires with a sexy shemale such  as myself? My name is Elissa and I ...

Superior Massage by gorgeous T-Girl T-Girl for Dating in Winston-Salem 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: Ga...

Transgender🟢TINA TS😉💋 Ready to play with a TGirl Tonight? Hi babe, I'm Tina 💋 I'm in Winston-Salem 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 no...

I 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 Winston-Salem area. Click here and come see me anytime!...

TS Latina Seductress – Thick, Wet & Ready to Be Used 💋🍑  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...

🖤 Ebony TS Playmate with a Curvy Body & a Wild Side 😘 Winston-Salem 🍑 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,...

New Body New Me M2F post-op in Winston-Salem 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...

Well Endowed Shemale is beautiful Winston-Salem 32 Well Endowed Shemale in Winston-Salem 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 my siz...

Winston, NC🍆TRANSGENDER Sexy Transgender Lady Wantingsex in Raleigh, North Carolina! 💋 WINSTON-SALEM, NC - Trans Messanger  I'm a Transgender lady living in Winston -Salem, North Carolina. I was born a male..however I always known I am a pretty girl.I love meeting for sex in North Carolina Winston - Sa...

Looking for a TS Woman Who Loves to Be Desired 💦🔥 Winston-Salem  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. 💋 I would love to meet a shemale or tra...

TS Latina Goddess – For Men Who Crave Passion, Fire & Pleasure 🔥💋  Hello sweetheart 😘 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...

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 Winston-Salem area and are interested then drop me a line and introduce yourself. Yo...

MALE SEEKING SHEMALE 🍆Winston-Salem Ready to Play and Fuck 💦 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 Winston-Salem  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 he...

Shy Transexual Escort in Winston-Salem 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 ...

Don't Hate Me 'Cause I am Fabu-licious!... Fun and Fabulous T-Girl in Winston-Salem Look no further honey, I'm Franny an Ebony trans woman here in Winston-Salem 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 do...

She-male looking for hot date to please. Asian Shemale in the Winston-Salem Area Hot Asian shemale wants to date and please you in the art of erotic passion. I'm non op, fully functional, lovely and funny. Please to contact me @CarmelShemaleXXX. My name is Carmel. I'm 33 years old. I like to explore your sexual fantasies! Let's make them...

YOUR EBONY SHEMALE - big boobs and a BIG COCK! Winston-Salem Hot Hot Hot! Sinead, a black shemale in Winston-Salem ready to make all of your  wildest fantasies come true! 💋🔥 My Pictures and Profile! -- You want to find a sexy ebony shemale in  Winston-Salemto fulfill all your dreams? Then stop searching because I am ready to make  all o...

Spicy 🌶 Latina Shemale in Winston-Salem Ready to Fill You 😉😉 LATINA SHEMALE SEEKING 🔥🌶  Are you looking for a spicy/hot HISPANIC TS.. absolutely KINKY and ready to do anything?? I'm from Winston-Salem.  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 l...

I'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 Winston-Salem 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 li...

Tiffany Shelle - Your Winston-Salem Tranny Girlfriend! 💞 Tranny Escort - Top/Bottom/GFE in Winston-Salem It’s Tiffany Shelle your perfect tranny girlfriend 🥰 💕 SAFE💕 💯 LEGIT ✨💞 SKILLED, Exotic and Erotic 💦 🥰 I’m available to explore your shemale fantasy and give you pleasures you've only dreamed of!  I'm 100% func...

Don't Worry I Bite! Feisty redhead trans in Winston-Salem 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 con...

Sexy hung and big busted Hung and Busty Shemale in Winston-Salem 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....

Dr 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 Winston-Salem area come see if you measure up! Click here for explicit photos. ...

Having fun and Staying Young Young 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 and message me xoxo, Sherry....

👠 Classy on the Streets, Naughty in the Sheets – Let’s Play 💋  💖 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...

Hot Shemale in Winston-Salem Ready to Fulfill Your Wildest Fantasies 👄💦🍆 I'm TS and Looking to Date in Winston-Salem My name is Shelly and I'm full TS.. Are you looking for a sexy shemale in Winston-Salem 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 peop...

I Need a Sexy Man to Tame Wild Willy! Hung Winston-Salem Trans Woman Are you a snake charmer? A willy whisperer? A swami of salami? I am Desi, a shemale in Winston-Salem 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 Starbuck...

I'll Make You Feel Like a King Baby! Trans Queen Seeks King in Winston-Salem I'm queen Delilah a trans woman here in Winston-Salem 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 scandal...

🍑 Your Secret Ebony Fantasy Is Just One Message Away 😜  👄 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...

British T-girl Seeking Classy Gentleman in Winston-Salem... 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 Winston-Salem and am financially independent and looking for a gentleman who is like-minded, equally solvent and has ...

TS Beauties—Let’s Make Some Memories 💖✨  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...

Seeking a Stunning TS for Passion & Pleasure 😘🔥  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...

!!!HOT - TRANS FUCKBOOK - HOT!!! Hookup With a Hot T-Girl in Winston-Salem Meet sexy shemales ready to have some adult fun with their admirers. Over 1,240 t-girls in Winston-Salem 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 On...

Trans Playmate Sex Kitten... Ebony trans woman in Winston-Salem 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....

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Crystal, 27 New to the area Heyyy!. I'm Crystal and I am 27. I'm new to the Winston-Salem 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 ...