Winston-Salem Transgender Classifieds

Browse Winston-Salem 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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June 1st, 2026
TS Sugar Baby💎 Your Perfect Trans Fantasy – Let’s Make It a Reality 💋  📍 Location: Winston-Salem 💖 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 a...
Petite TS Doll Looking for a Fun Sugar Daddy 🍬💋 Hi babe... I'm a tiny trans girl, very sexy and feminine. I love to have fun and I'm a very loving girl, I have a lovely sweet smile. I love to be worshiped and pampered by a dominant confident man, who always takes care of his girl, and knows how to please her. HMU HERE BABE!! I am pretty affectio...
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 masseuse, hot body, in great shape, and well hung. If you want to get together, Send me a private message Crystal27trans <3  Username: @Crystal27transLocation: Winston-Salem, No...
Luxury Ebony TS Sugar Baby With Style 👠💎 Hello handsome… I am a ebony trans sugar baby, a beautiful, classy and elegant young lady. I look for confident men that are also very kind to women and who like to spoil a gorgeous lady. Fashion, food and especially great chemistry are my top priorities. let's plan our play date. I love peo...
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...
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...
💜 Cute TS Girl Looking for the Right Guy 😘 Just moved to Winston-Salem😊 Gorgeous, very sweet and easy to get to know. I am a trans girl seeking to meet men that are confident and know what they are looking for, yet are also looking for some friendship with a new person. I enjoy going out for cocktails and having a good time, flirting with...
I’m a Sexy and Naughty T-Girl Here in Winston-Salem. Winston-Salem T-Girl 4 NSA Fabulous Fanny here boys! I'm a trans woman living in the Winston-Salem 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  wo...
Low-Key TS Sugar Baby 🌙 Soft Vibes, Selective Energy in Winston-Salem I’m a TS sugar baby who keeps things calm, classy, and intentional. Evenings without noise, talks that flow naturally - these mean something to me. Confidence shows in stillness, not noise. Soft in manner, sharp in choices. Comfortable standing out, never trying too hard. 😌💄Let's Link Up...
Spicy and Hot T-Girl from Colombia Latina T-Girl in Winston-Salem Hey guys, I am Colleen and I am looking for a long term relationship. I am open to FWB but would like something more serious eventually. I am 33 and have not had surgery. Nice surpise waiting for you! Send me a private message! ColleenLatinaT...
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 Winston-Salem tranny tonight. Save your appetite boy! Me: trans, 30yrs, 5'10, functional, thick, uncut and longe...
May 31st, 2026
Hot trans chick with nice boobs Hot trans chick in Winston-Salem. 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!! W...
Strict Shemale Dominatrix in Winston-Salem - @DesireeTransDomme Powerful African-Queen Dominatrix in Winston-Salem I am full-time professional Domme Desiree. My Winston-Salem area dungeon is well equipped. This is My life, not a hobby. I am a strong-willed shemale who will take charge and maintain total control. Your obedience is required at all times and you w...
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...
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 @BlancaShemale32 with your recent pic or selfie for my latest pictures ...
Latina TS Dirty Girl Looking for a Gentleman's Dark Side 🔥👠  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 😘 I need you to undress me gr...
Tantalizing Tina with a HUGE W33NAH! Winston-Salem Trans Woman for Hookup! Hey gents I'm Tina a trans female hot for all you sexy Winston-Salem 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!  ...
Superb Shemale in Winston-Salem... T-Girl for NSA Encounters in Winston-Salem When you decide to take a walk on the wild side it's always best to take me, Nicky, a superb shemale in Winston-Salem. I've got everything you need and then some. Fully functional, petite, passible and extra large for extra fun! I love to flirt, fondl...
Having 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...
Hi Guys!! 32 y/o Trans looking for someone fun! Lara 32 y/o Transexual in Winston-Salem for Man Hello, thanks for looking at my ad! I'm Lara. I am 32 years old and transitioned when I was 24 but no surgery other than breast augmentation and some minor body touchups. I pass exceptionally well, fully functional. I'm feminine and classy so you will...
Twisted Sister - Loves to Ride.... and be Ridden! So, you wanna ROCK?! Fully function and extra large (10inch) surprise for all my Winston-Salem 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...
The Trevor Project Saves Young LGBTQ+ Lives BonePage Supports The Trevor Project Proudly sponsored by Winston-Salem 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, bi...
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 ...
May 30th, 2026
Winston-Salem's Transtastic Toni... I LIKE to do the Wild Thing! T-Girl Toni for NSA in Winston-Salem Hi you sexy man! I'm Toni a trans woman from here in Winston-Salem. 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, function...
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!...

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