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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August 5th, 2026
💜 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...
HOT SHEMALE GIA will Satisfy Your Tranny Fantasy Winston-Salem! 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 Winston-Salem!  No strings - just great times, so join my page free for instant access! Shemale Gia's Winston-Salem Sexbook @ShemaleGia27 P...
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...
🔥 Sexy Trans Beauty in Winston-Salem – Let’s Play 😘 🔥 I’m a confident, flirty trans woman looking for a naughty, open-minded man who knows how to have a good time. I require someone who lives near me to establish genuine emotional bonds through playful games while they disclose their sexual interests to me 😈. waiting for your message babe!! I...
SHEMALE HOOKUPS! Wanna Have a Great Time? Join Free Now! HOT!  SHEMALE HOOKUPS  "The girl with a naughty little secret in her panties!" SIGNUP FREE: INSTANT ACCESS! Shemale Profiles Black Shemales | Asian Shemales | Crossdressing Friends...
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...
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...
Jasmin T-girl Ready to make friends Want to Meet a T-Girl in Winston-Salem? 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 ...
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'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 bed...
Hookup With Winston-Salem TS Sugar Baby Now! 💌 Want to Hookup and Find Winston-Salem 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're interested in 😉.. Do you want to meet local shemales who want to fuck and have some sexy fun?...
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...
Sexy hung and big busted Hung and Busty Shemale in Winston-Salem 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: Winston-Salem, Nor...
Selena 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 ...
Beautiful Krystale 25 Winston-Salem visiting now Beautiful Preop 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.  Krystale25shemale Username: @Krystale25shemale Age: 25 Location: Winston-Salem, North Carolina Sex: MtF Trans ...
August 4th, 2026
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!...
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...
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...
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 ...
I'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 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...
💎 Confident TS Sugar Baby in Winston-Salem 💎 I enter any space with my confident trans woman presence which immediately makes me the center of attention. I find great happiness when people express their admiration and appreciation for me while they actively provide me with care. I find complete happiness when someone else handles everything be...
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 ...
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...
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...
💗 💫 TS Sugar Baby Ready for Real Dates & Real Vibes in Winston-Salem Hi Winston-Salem 💕Confident. Female. Transgender. Sugar dating means soft evenings, steady talk, space to breathe. Calm hours suit me better than noise. Respect grows where pressure fades. Warm necessary. Polite by choice. Kept with care. Affection follows ease, not effort. Let's Link Up Babe - ...
Free North Carolina Transexuals Guide North Carolina Transexuals Guide The North Carolina 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 North Carolina Transexuals Guide online.  Where to Meet T...
!!!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...
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...
Penny for your thoughts? Penny TS in Winston-Salem 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 ...
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...
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...
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...
Winston-Salem💋 TS Tina – Your Naughty Escape, Anytime, Anywhere 🌎🔥 Hey sexy… Your sweet seductive fully loaded TS dream girl Tina is here to fulfill your deepest desires from anywhere in the world 😘 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...
Cute TS Sugar Baby With a Sweet Personality 🌸💕 Hi I’m a trans girl, looking for a nice and confident guy. I like to look pretty and be the centre of attention, so you would need to be confident and also respect women. I love going out with friends and love to be social and have fun and laugh. I also love to be romantic and to be hugged, ki...
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...
Cute TS Sugar Baby Seeking Male💎Aria Username: @AriaSweet Trans Friendly: Yes Private Meetups: Yes Phone Chat: Yes Pics Available: 18 Message me if you like feminine Transsexual 💬 Hello, I am AriaTS here in Winston-Salem. A very sweet and very feminine trans-girl that loves to be your sugary little sugar-baby, accompanied by a...
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...
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...
August 3rd, 2026
I'm a Horny Shemale 😈💋 Looking For Sex Tonight!! Sexy Shemale💎 Ready to Rock Your World! Local Transsexual - TGIRL Sext App 📲 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...
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...
TS Temptress Ready to Ruin You (In the Best Way) 😈💦 Winston-Salem  Hey lover 😘 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...
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...
Erotic exotic Asian queen in Winston-Salem now (25) Asian Transexual in Winston-Salem 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. ...
Email Winston-Salem Shemales❤️‍🔥 I'm a well hung TGIRL and Want to have some sexy fun tonight.. Let's Fuck Want to meet the Shemale and Transsexual of your dreams? Look no further, this website gives you instant access to real TGIRLS, SHEMALES and TRANSSEXUALS!! The best part is they are online and you get connected...
🔥 TS Yessica – Verified & Ready in Winston-Salem 🔥 TS Yessica shows her confident and playful personality when she meets new people because she shows them her authentic self. 😘 You have discovered your perfect trans escort who will create unforgettable experiences while providing an outstanding encounter. I dedicate my free time to people who gen...
Shy Crossdresser Seeks Friend Where I Can Discreetly Dress Up and Possible Dates. Crossdresser Seeks Friend in Winston-Salem Area Hi, my fem name is Gloria. I'm a married crossdresser in the Winston-Salem 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 cr...
Glamorous TS Sugar Baby Ready to Be Spoiled 💎💋 Hi handsome… I’m a beautiful trans sugar baby that loves the luxuries in life and I’m searching for a confident man who will treat me like the queen I am. I am very soft and feminine with a playful edge and you will always have a smile on your face when we talk. View My TS Sugar B...
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...
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...
TS Tina – Your Seductive Fantasy in Winston-Salem 🔥 Your dream TS girl Tina has arrived to create a hot experience while she will help you discover your most intense sexual fantasies. I create a perfect combination of wild and warm sensations through my soft touch and my playful nature. I find men who understand how to handle a woman with confidence ...
Trans Sugar Baby Energy in Winston-Salem - I'm ready for a night out! Hey there… I’m a sweet, confident, and playful trans beauty in my early 20s who loves good vibes, strong chemistry, and nights that turn into stories you replay later 😘 I enjoy being admired, feeling cared for, and bringing a little sparkle wherever I go. Yes, I can be your “ba...

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